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Phenolic compounds in Cistus incanus herbal infusions — Antioxidant capacity and thermal stability during the brewing process

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Abstract

Currently numerous manufacturers offer herbal infusions or dietary supplements based on the plant Cistus incanus. These products are especially promoted as offering a high content of phenolic substances together with an associated strong antioxidant activity. For the customers it is of interest, if the advertised phenolic contents are valid, plant material is authentic and if the suggested effects can be obtained through ingestion. As it is known from the literature, phenolic compounds can undergo severe changes resulting from cooking. Therefore, it is important to consider processing parameters such as brewing water, brewing temperature, and brewing duration for the preparation of C. incanus herbal infusions. The aims of this study were to analyze the phenolic compounds of C. incanus herbal infusions, to estimate the antioxidant capacity of the individual phenolic substances, as well as to investigate the influence of the brewing process on the phenolic compound profile. By the use of LC–DAD/ESI–MS/MS thirty-two phenolic compounds (e.g. phenolic acids, flavan-3-ol monomers and -dimers as well as flavonol glycosides) were identified. Additionally, specific antioxidant capacities were attributed to corresponding substances by using the LC–onlineTEAC (Trolox Equivalent Antioxidant Capacity) methodology. Moreover, the selection of brewing water, boiling time as well as boiling temperature had a significant influence on the content of the phenolic compounds in C. incanus infusions. On the basis of these results, it can be concluded, that an incorrect choice of brewing process parameters could result in a decreased amount of phenolic substances in the final C. incanus beverages accompanied with a reduced antioxidant activity.

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... Przypuszcza się, że obecność flawonoli w rodzaju Cistus jest uwarunkowana klimatem śródziemnomorskim, w którym występuje intensywne nasłonecznienie. Związki te, absorbując znaczne ilości promieniowania UV, chronią roślinę przed jego szkodliwym działaniem [29][30][31][32]. ...
... Do najczęściej identyfikowanych glikozydów mirycetyny zalicza się: 3-O-glukozyd mirycetyny [29][30][31], 3-O-ramnozyd mirycetyny (mirycytryna) [30], 3-O-galaktozyd mirycetyny [31,33] oraz bliżej niezidentyfikowane: ksylozyd mirycetyny [31] i ramnozylo-heksozyd mirycetyny [33]. Wśród glikozydów kwercetyny wyróżnia się: 3-O-glukozyd kwercetyny (izokwercytryna) [30], 3-O-ramnozyd kwercetyny (kwercytryna), 3-O-galaktozyd kwercetyny (hiperozyd), 3-O-ksylozyd kwercetyny, 3-O-arabinozyd kwercetyny [30,33], 3-O-rutynozyd kwercetyny (rutozyd, rutyna) oraz 7-O-heksozydo-3-O-rutynozyd kwercetyny [34]. ...
... Do najczęściej identyfikowanych glikozydów mirycetyny zalicza się: 3-O-glukozyd mirycetyny [29][30][31], 3-O-ramnozyd mirycetyny (mirycytryna) [30], 3-O-galaktozyd mirycetyny [31,33] oraz bliżej niezidentyfikowane: ksylozyd mirycetyny [31] i ramnozylo-heksozyd mirycetyny [33]. Wśród glikozydów kwercetyny wyróżnia się: 3-O-glukozyd kwercetyny (izokwercytryna) [30], 3-O-ramnozyd kwercetyny (kwercytryna), 3-O-galaktozyd kwercetyny (hiperozyd), 3-O-ksylozyd kwercetyny, 3-O-arabinozyd kwercetyny [30,33], 3-O-rutynozyd kwercetyny (rutozyd, rutyna) oraz 7-O-heksozydo-3-O-rutynozyd kwercetyny [34]. ...
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One of the modern nutritional trends is to enthusiastically look for natural products that can be considered functional food and be a source of ingredients with a health-promoting effect. Today, many food manufacturers offer Cistus × incanus leaves to prepare common self-preparations (e.g., infusions) or as ready-to-use dietary supplements. Cistus × incanus (rock rose, pink rock-rose, hoary rock-rose), belonging to the family Cistaceae, is widespread in Mediterranean countries. For many years, cistus extracts and its aromatic resin have been used in traditional Middle East medicine to treat, among others, colds, fever, stomach problems, and skin wounds. In past years, this plant was rediscovered by the public. Due to the growing popularity of Cistus products, the most recent scientific literature on this subject is reviewed here. This article aims to present the latest research results on the phytochemical composition of Cistus × incanus and the impact of its consumption on human health. Particular emphasis is put on antioxidant, anti-inflammatory, antibacterial, antiviral, and antiproliferative activities and support of digestive system functions. Studies have shown that the main active ingredients of Cistus × incanus are flavonoid compounds, including flavonol glycosides (myricetin, quercetin, kaempferol), flavan-3-ols, and tannins. It was demonstrated that the presence of these compounds determines the therapeutic and health-promoting properties of cistus leaves and its products. That applies primarily to a strong antioxidant effect, which may reduce the risk of noncommunicable diseases, including cardiovascular diseases, neurodegenerative diseases, and cancer. Cistus preparations are also recommended as immunostimulants, supporting the treatment of bacterial and viral infections. Labdanum oleoresin and essential oil are a valuable source of substances with strong antibacterial and anti-inflammatory properties, which can be used in the future in the production of pharmaceutical and cosmetic preparations, and also serve as a natural food preservative.
... There is only little information available on the bioactive compounds such as catechins and alkaloids of this wild plant infusion determined by LC-MS/MS. Usually, the characterization of flavonoid compounds in methanol extract has been reported but without their quantification (Riehle et al., 2013). ...
... and 63°C, respectively. These data are in agreement with Riehle et al. (2013) who have shown that for the selection of water as a medium, brewing time and temperature had a significant influence on the content of the phenolic compounds in Cistus incanus infusions. At higher temperature (even 95°C) of brewing the 33% increase in total peak area of all 24 phenolic compounds of the methanolic SPE eluate was found, especially for catechin. ...
... The results of the identification of flavan-3-ols for Cistus incanus were previously reported by Barrajón-Catalán et al. (2011);Petereit et al. (1991) and Riehle et al. (2013) but only for gallocatechin, catechin and epicatechin. The authors have also found dimers or/and isomers of gallocatechin and procyanidins B 1 and B 3 but they have not determined these compounds. ...
Article
Cistus incanus is called a medicine herbal plant due to its antimicrobial, anti-inflammatory, cytotoxic and antiulcerogenic properties. Considering these unique properties, quantification of the bioactive compounds of its infusion by liquid chromatography-tandem mass spectrometry is very important because of the rising consumption of this beverage. In this study the content of 28 phenolic compounds and theirs derivatives, alkaloids and vitamin B of water extract of Cistus incanus tea was examined and the results were compared with the results from other types of popular in the market teas. The Cistus incanus infusions were tested for content of flavanols, flavonols, organic acids, vitamin B and alkaloids and were compared with Camellia sinensis, Hoan Ngoc herbal tea and Rooibos infusions. Camellia sinensis infusions generally contained more catechins (1.56–82.65 mg/g) than Cistus incanus (1.02–2.73 mg/g) but there was no catechin-3-gallate in any Camellia sinensis infusions. Caffeine, theobromine and theophylline were found practically only in Camellia sinensis (6.22–14.19 mg/g) and Vietnamese herbal tea (2.97 mg/g) while trigonelline was found at higher concentrations in both Cistus incanus (6.29–14.34 μg/g) and Rooibos infusions (10.54–14.29 μg/g) than in Camellia sinensis infusions (0.30–2.88 μg/g). Principal component analysis revealed both similarities and differences among the infusions.
... There is only little information available on the bioactive compounds such as catechins and alkaloids of this wild plant infusion determined by LC-MS/MS. Usually, the characterization of flavonoid compounds in methanol extract has been reported but without their quantification (Riehle et al., 2013). ...
... and 63°C, respectively. These data are in agreement with Riehle et al. (2013) who have shown that for the selection of water as a medium, brewing time and temperature had a significant influence on the content of the phenolic compounds in Cistus incanus infusions. At higher temperature (even 95°C) of brewing the 33% increase in total peak area of all 24 phenolic compounds of the methanolic SPE eluate was found, especially for catechin. ...
... The results of the identification of flavan-3-ols for Cistus incanus were previously reported by Barrajón-Catalán et al. (2011);Petereit et al. (1991) and Riehle et al. (2013) but only for gallocatechin, catechin and epicatechin. The authors have also found dimers or/and isomers of gallocatechin and procyanidins B 1 and B 3 but they have not determined these compounds. ...
Article
The Publisher regrets that this article is an accidental duplication of an article that has already been published, https://doi.org/10.1016/j.jfca.2019.01.021. The duplicate article has therefore been withdrawn. The full Elsevier Policy on Article Withdrawal can be found at https://www.elsevier.com/about/our-business/policies/article-withdrawal
... In general, increase in the infusion time results in an accelerated extraction of bioactive compounds. The present approach is based on the experimental design established by Riehle et al. [31]. ...
... When tap water would be used for brewing, a lower content on bioactive compounds would be the result. A possible explanation is the so called 'tea cream' formation [31], which corresponds with the mineral content in water and forms because of high phenolic content, caffeine and theaflavins, thearubigins, and mineral content of the water. However, optimized brewing conditions of pu'er tea infusions are very important. ...
... However, optimized brewing conditions of pu'er tea infusions are very important. Here, pu'er tea infusions were prepared according to Riehle et al. [31]. In the present study, 0.4 g whole tea leaves material were weighed into a 50 mL centrifuge vessel and brewed that vessel in 40 mL of distilled boiling water. ...
Article
Full-text available
Pu'er tea produced from Camellia sinensis var. assamica is a widely appreciated and consumed beverage that can be divided into two kinds of tea depending on the different fermentation processed used, the special sensory characteristics, and their chemical composition. However, authentication seems to be very important for such teas, as they are traded to comparatively high prices, especially in Europe. The results for selected biochemical markers showed that aged raw pu'er tea contained 210.2 mg GAE/g polyphenols, of which 2.2 mg/g were gallic acid, 16.1 mg/g theogallin, 35.1 mg/g (−)-epigallocatechin gallate, and 40.1 mg/g (−)-epicatechin gallate, on average. Young ripened pu'er tea contained about 104.6 mg GAE/g polyphenols, of which 5.5 mg/g gallic acid, 0.9 mg/g theogallin, 0.7 mg/g (−)-epigallocatechin gallate, and 1.8 mg/g (−)-epicatechin gallate, on average. An additional objective of the present study was to unravel the best brewing conditions for optimal extraction of the bioactive compounds. Infusions of nineteen commercial teas (from pu'er cakes) were obtained at different time-temperature ratios for studying the content of bioactive compounds (flavan-3-ols, flavonols, caffeoylquinic acids, methylxanthines). Brewing at 90 • C for 5 min was the best condition to obtain a high content of total polyphenols in ripened pu'er tea. Principal component analysis and hierarchical cluster analysis showed, that young ripened and aged raw pu'er tea can be successfully differentiated by the analyzed chemical compounds. Principal component analysis results indicated that young ripened pu'er tea has higher contents of gallic acid, quercetin, and kaempferol than aged raw pu'er tea.
... HPLC retention times (Rt) of the 13 evaluated peaks, mass data (base ions at negative mode ([M-H] -), main fragment ions (MS/MS)), peak identification (M = myricetin, Q = quercetin) and relevance of compounds within aqueous extracts of C. creticus (range of relative area percentages at 354 nm). 1) Highlights compounds that were identified via reference compounds; 2 highlights peaks that were shown to be double peaks in a part of the accessions (characteristics of the overlain peak are indicated below the respective line). Identification literature [11][12][13]26,31,[36][37][38]. [11][12][13]26,31,37,38] 0-35% ...
... Identification literature [11][12][13]26,31,[36][37][38]. [11][12][13]26,31,37,38] 0-35% ...
... In particular, the weak or lacking statistical correlation between antioxidative activity and myricetin or quercetin glycosides was rather surprising. Myricetin, quercetin and some of their glycosides, especially their rhamnosides, were described to be powerful antioxidants, with an antioxidant activity similar to or slightly weaker than that of vitamin E [37,46]. However, when comparing the plots of total, myricetin, quercetin and punicalagin derivative contents of the different species with the plot visualizing their antioxidative capacity, the patterns are obviously not congruent. ...
Article
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This investigation focused on the qualitative and quantitative composition of polyphe-nolic compounds of Mediterranean northern shore Cistus creticus and six further, partly sympatric Cistus species (C. albidus, C. crispus, C. ladanifer, C. monspeliensis, C. parviflorus, C. salviifolius). Aque-ous extracts of 1153 individual plants from 13 countries were analyzed via high performance liquid chromatography (HPLC). The extracts of C. creticus were primarily composed of two ellagitannins (punicalagin and punicalagin gallate) and nine flavonol glycosides (myricetin and quercetin glyco-sides, with m-3-O-rhamnoside as the dominant main compound). Differences in the proportions of punicalagin derivatives and flavonol glycosides allowed the classification into two chemovariants. Plants containing punicalagin derivatives and flavonol glycosides were especially abundant in the western and central Mediterranean areas and in Cyprus. From Albania eastwards, punicalagin and punicalagin gallate were of much lesser importance and the predominant chemovariant there was a nearly pure flavonol type. With its two chemovariants, C. creticus takes a central position between the flavonol-rich, purple-flowered clade (besides C. creticus, here represented by C. albidus and C. crispus) and the more ellagitannin-rich, white-or whitish-pink-flowered clade (here represented by C. ladanifer, C. monspeliensis, C. parviflorus and C. salviifolius). The median antioxidative capacity of C. creticus plant material was, with 166 mg Trolox equivalents/g dry wt, about half of the antioxida-tive capacity of C. ladanifer (301 mg te/g dry wt), the species with the highest antioxidative potential.
... Attaguile et al. [2] investigated the effects of the aqueous extracts of CI and Cistus monspeliensis on DNA cleavage, and their free-radical scavenging capacity was also analyzed. The impact of the extracts on lipid peroxidation in rat liver microsomes was also evaluated [11]. These products are characterized by a high content of phenolic substances and strong antioxidant activity [11,12]. ...
... The impact of the extracts on lipid peroxidation in rat liver microsomes was also evaluated [11]. These products are characterized by a high content of phenolic substances and strong antioxidant activity [11,12]. Gori et al.'s study [3] aimed to characterize the major polyphenolic compounds present in a crude ethanolic leaf extract of CI. ...
... Phenolic compounds can undergo severe changes when exposed to various processing techniques [11]. Therefore, standardizing the processing parameters is of the most importance. ...
Article
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Cistus incanus L. (CI) has been proposed as an innovative functional supplement of food products, and hence the present study aimed to evaluate the effect of the addition of dried CI on the properties of bread. Bread was prepared from white wheat flour supplemented with the addition of 1%, 2%, 3%, 4%, and 5% of ground CI. After the completion of baking process, various characteristics of the obtained bread product, such as yield, volume, porosity, acidity, color, and texture, were evaluated. In addition, total phenolic content (TPC), ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) radical scavenging activity, chelating power (CHEL), and ability to quench OH∙ radicals were measured. The results showed that the addition of CI to bread caused a reduction in the volume of bread, but texture of the crumbs was acceptable. Acidity and moisture content of bread were found to be increased following CI enrichment. Significant changes in the ash content and the color of bread crumbs were also observed. Bread incorporated with CI was characterized by significantly higher TPC and much higher antioxidant activity, as measured by ABTS, CHEL, and OH∙ radicals, compared to control bread. Supplementation of bread with 3% CI produced a product with desirable characteristics which was also favored by consumers.
... Recently, different biological activities have been demonstrated for the leaf extracts of this species and have provided scientific evidence to their traditional utilizations. In particular, antioxidant [5][6][7], antiviral [8] and antimicrobial properties [9] have been described in experimental models. ...
... Currently, C. incanus is considered a medicinal plant and the dried leaves are used as herbal infusions ("Cistus tea") [5,10] and dietary supplements [11]. In addition, the herbal extract CYSTUS052 ® (Dr. ...
Article
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Cistus x incanus L. is a Mediterranean evergreen shrub used in folk medicine for the treatment of inflammatory disorders but the underlying mechanisms are not fully understood. We therefore investigated the anti-inflammatory effects of an ethyl acetate fraction (EAF) from C. x incanus L. leaves on lipopolysaccharide (LPS) activated RAW 264.7 macrophages. HPLC analysis revealed myricetin and quercetin derivatives to be the major compounds in EAF; EAF up to 1 µM of total phenolic content, was not cytotoxic and inhibited the mRNA expression of interleukin-6 (IL-6) and cyclooxygenase-2 (COX-2) (p < 0.05) and the production of prostaglandins E2 (PGE2) (p < 0.05). Meanwhile, EAF triggered the mRNA expression of interleukin-10 (IL-10) and elicited the nuclear translocation of nuclear factor erythroid 2-related factor 2 (Nrf2), as well as the expression of its main target gene, heme oxygenase-1 (HO-1) (p < 0.05). These data indicate that EAF attenuates experimental inflammation via the inhibition of proinflammatory mediators and at least in part, by the activation of Nrf2/HO-1 pathway. These effects are likely due to myricetin and quercetin derivatives but the role of other, less abundant components cannot be excluded. Further studies to confirm the relevance of our findings in animal models and to highlight the relative contribution of each component to the anti-inflammatory activity of EAF should be conducted.
... The variation may be due to a different manner of extract preparation or the various sites of origin and time of harvest. It was previously observed that the chemical composition of rock rose infusions are affected by different brewing temperature and time [20], different particle size, and the amounts of individual plant parts (leaves, stems) in the dried raw plant material [47]. A larger amount of polyphenols was recorded in dried methanol and water-methanol extracts, 269.3-347.3 ...
... Apart from flavonols, the presence of ellagic acid and ellagitannins-punicalin, punicalagin, terflavin A and cistusin-was also detected. The results obtained support previous reports on the phytochemical composition of C. incanus leaves [18,20,23,[50][51][52][53][54]. DPPH, ABTS, and FRAP are frequently used spectrophotometric methods to measure antioxidant action. ...
Article
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Reactive oxygen and carbonyl species promote oxidative and carbonyl stress, and the development of diabetes, metabolic syndrome, cardiovascular diseases, and others. The traditional herb Cistus × incanus is known for its antioxidant properties; therefore, the current study aimed to assess how the chemical composition of a C. incanus water infusion corresponds with its antioxidative and antiglycative effects in vitro. The composition of infusions prepared from commercial products was analyzed with UHPLC-ESI-qTOF-MS. Total phenolics, flavonoids, and non-flavonoid polyphenols were determined. Antioxidant activity of infusions and selected polyphenols was investigated using DPPH, ABTS, and FRAP. Fluorometric measurements and methylglyoxal capture were performed to investigate the antiglycation activity. PCA and PLS-DA models were applied to explore the correlation between chemical and antioxidant results. The principal flavonoids in C. incanus were flavonols. In vitro tests revealed that a stronger antioxidant effect was demonstrated by plant material from Turkey rich in flavonoids, followed by Albania and Greece. Flavonols and ellagic acid displayed stronger antiradical and reducing power than EA-derived urolithins. Hyperoside was the most potent inhibitor of glycation. The results indicate that flavonoids are primarily responsible for rock rose antioxidant and antiglycation properties. PLS-DA modeling can be used to identify the origin of plant material with sensitivity and specificity exceeding 86%.
... In addition to chemical content, the biological activity of the extracted substances was change by changing of method of drying herbal material; As well as the essential oil of Mentha longifolia L. Hudson dried in shade has exhibited the highest antioxidant activity and dried samples in laboratory in the oven has the lowest antioxidant property (Riehle et al., 2013) that similar results was obtained in our study. It was showed that most oil content in savory was in temperature of 45 ºC oven, shade and sun drying methods, respectively (Rocha and Melo, 2011); this results is disagree with the results of our study that the most oil content was in shade, sun and 70 ºC oven, respectively. ...
... The essential oil content of sage and thyme (Thymus vulgaris) dried in oven at 60 ºC were reduced in higher temperature (Sefidkon et al., 2006). Furthermore, similarly results with our results was reported (Riehle et al., 2013;Sellami et al., 2015) that the extracts of herbs dried in the laboratory oven (1.13 ± 0.11 m/mol Fe2+/mg of the dry extract and EC50 = 0.033 ± 0.001 mg/mL) has shown the lowest antioxidant capacity. Such results reveals value of methods that plant is dried prior of preparation. ...
Article
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Abstract : Mentha longifolia has the widest natural geographic distribution of any menthe species, from Western Europe to central Asia and in southern Africa. The current study was conducted to determine the antioxidant capacity of extracts and essential oil taken from aerial portions of M. longifolia L. The plant materials were dried by three different techniques (shade, sun and oven drying). Collected horsemint shoots were grinded then for evaluating effect of different extraction methods (maceration by aqueous, ethanolic and hydroalcoholic solvents, soxhlet and essential oil by Clevenger) and drying technique (shade drying, sun drying and oven drying) were used. Total phenol content (TPC) and total flavonoid content (TFC) of the samples were measured. Furthermore, total antioxidant capacity (TAC) was evaluated by both phosphomolybdenum and DPPH% assays. Soxhlet extraction of shade drying had highest TPC and TFC among other extracts a drying methods. In terms of antioxidant activity, essential oil obtained from Clevenger displayed high antioxidant capacity, resulting in a higher radical scavenging ability, which can be attributed to the lower temperatures in shade dried plant material and the higher stability of the extracted compounds. But by exposure the shoots to sun or high temperature (oven) decreasing of bioactive compounds amounts present in plant material were observed. There was a significantly positive correlation (P0.7) between TPC and TFC in all drying techniques. Also a significant correlation was observed between TAC and %inhibition (P0.8) in sun drying extracts. Extraction and drying the herbal material influences the bioactive compounds and antioxidant properties. Keywords: Mentha longifolia L., extraction, antioxidant capacity, drying, total phenol content
... Cistus incanus infusions and products containing extracts are notable examples for such polyphenolrich food supplements because many research studies have demonstrated that the main biologically active components of the wild herb refer to polyphenolic compounds such as gallic acid, rutin, quercetin, kaempferol, glycoside compounds belonging to the fl avonol family, fl avan-3-ols as well as catechin, epicatechin [7], gallocatechin and gallocate chin-3gallate [8]. Traditional Mediterranean folk medicine has used Cistus species for anti-infl ammatory, antiulcerogenic, wound healing, antimicrobial, cytotoxic and vasodilator remedies [9]. of monomers such as gallic acid, epigallocatechin, catechin, and epicatechin [10]. ...
... In Cistus, incanus growing in Italy was found gallic acid, catechin, and rutin received from an infusion of powdered plant leaves and analyzed with HPLC-MS[32]. By HPLC-MS analyses of Greek Cistus incanus infusions were identifi ed phenolic acids, fl avan-3-of monomers, and dimers as well as fl avonol glycosides[9].Roots and aerial parts of Cistaceae have been used since ancient times in the Mediterranean cultures for its medicinal properties. No previous HPLC reports have been found in the composition of the hard-coated seeds of the Cistus incanus. ...
... An infusion is obtained by adding hot water to a specific amount of plant material and leaving the mix to brew, similar to the preparation of tea (Martins et al., 2015;Rodrigues et al., 2017). The different extraction methods have a direct impact on the composition of the final extract and, thus, on its bioactivity (Guimarães et al., 2013;Quesille-Villalobos, Saavedra, & Gálvez, 2013;Riehle, Vollmer, & Rohn, 2013). ...
... For Turkish black tea, Kelebek (2016) reports the greatest extraction of compounds with an antioxidant activity after 10 min brewing; however, the extraction speed was highest at 3 min, where it was double that seen at 6 min. Similar results have been obtained by Jovanović et al. (2017) in T. serpyllum, and by Riehle et al. (2013) in Cistus incanus; in both of these studies, the polyphenol content increased with extraction times, and extraction speed was higher at shorter extraction times. Extraction efficiency seems to be the highest at a brewing time of 5 min, in accordance with the recommendations of the manufacturers of commercially available infusions. ...
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Brewing conditions influence the composition and properties of herbal infusions. Acantholippia deserticola (Phil.) (RR) is a native and medicinal, Chilean Altiplano herb. This study assessed the effect of the section plant used, mass:water ratio and brewing time, on the infusions RR characteristics. RR leaves had higher total polyphenols (TPP) and antioxidant capacity (A.C.) than the stem. Polyphenol, chlorophyll and pheophytin extraction was maximized after 5 min brewing. Infusion prepared with 1 g has lower extraction ratio, per herb mass used, than those with 0.5 g. The infusion contained 10.1 µmol/L TPP, 5.5 µg/mL chlorophyll and 4.3 µg/mL pheophytins. Its A.C. was 69.2 µmol Trolox eq./L (FRAP), its IC50 was µg/mL 337 (DPPH) and 438 µg/ml (ABTS), and a dose of 300 mg/kg had an anti-inflammatory effect. The section of the plant, the herb : water ratio and the brewing time affect the characteristics of the RR infusions.
... C. incanus is a thermophilic plant which requires much light and for this reason it's growing in warm and temperate places (Gori et al., 2016). Studies showed that the extract of C. incanus has antifungal, antibacterial and antiviral properties, because of its constituents which includes tannins, flavonoids and other bioactive compounds (Attaguille et al., 2000;Riehle et al., 2013;Roidaki et al., 2016) In traditional medicine, C. incanus has been used in anti-inflammatory, anti-allergic, antiulcerogenic, wound healing, antimicrobial, cytotoxic and vasodilator remedies (Riehle et al., 2013). ...
... C. incanus is a thermophilic plant which requires much light and for this reason it's growing in warm and temperate places (Gori et al., 2016). Studies showed that the extract of C. incanus has antifungal, antibacterial and antiviral properties, because of its constituents which includes tannins, flavonoids and other bioactive compounds (Attaguille et al., 2000;Riehle et al., 2013;Roidaki et al., 2016) In traditional medicine, C. incanus has been used in anti-inflammatory, anti-allergic, antiulcerogenic, wound healing, antimicrobial, cytotoxic and vasodilator remedies (Riehle et al., 2013). ...
Article
Aflatoxins are secondary metabolites, with aflatoxin B1 being the most common, reported as carcinogenic, teratogenic and genotoxic. This study investigates the antiaflatoxigenic efficacy of the herbaceous plant Cistus incanus L. against Aspergillus parasiticus in two substrates, yeast extract sucrose medium and macadamia nuts. The methanolic extract of Cistus incanus showed pronounced antiaflatoxigenic ability, inhibiting aflatoxin B1 production in both substrates. AFB1 production was decreased significantly in a percentage of 87.1–90.1% after Cistus incanus extract addition in YES medium. The extract effectiveness was also observed in macadamia nuts, where the AFB1 production by Aspergillus parasiticus was reduced in a percentage of 72.5–85.9%. Moreover, the risk assessment was estimated taking into account the maximum amounts of AFB1 produced in inoculated samples with and without Cistus incanus addition. It was revealed that Cistus incanus presence leads to a lesser exposure of AFB1 to consumers.
... The presence of flavonols such as glycosides of myricetin, quercetin and kaempferol; monomeric flavan-3-ols, proanthocyanidins, hydrolyzable tannins and other polyphenolics including simple phenolic acids (e.g. gallic, ellagic, gentisinic) was described as typical for Cistus plants ( Gaweł-Bęben et al., 2020;Gori et al., 2016;Jeszka-Skowron et al., 2018;Móricz et al., 2018;Petereit et al., 1991;Riehle et al., 2013Riehle et al., , 2014Wittpahl et al., 2015). Additionally, leaves and stems of all Cistus species contain essential oils (monoterpenes and sesquiterpenes) and brown resin, which mostly consists of labdane-type diterpenes (Gori et al., 2016;Mansoor et al., 2016;Szeremeta et al., 2017). ...
... Preparations of Cistus × incanus L. leaves, e.g., infusions, hydromethanolic and hydroacetonic extracts, can be characterized by a high concentration of water-soluble polyphenolics ( Figs. 1 and S4), including glycosides of flavonols, monomeric and oligomeric flavan-3-ols, as well as ellagitannins (Barrajón-Catalán et al., 2011;Gürbüz et al., 2018;Petereit et al., 1991). Using the LC-MS n method, more than thirty compounds have been identified in pink rock-rose by some authors (Gaweł-Bęben et al., 2020;Gori et al., 2016;Riehle et al., 2013Riehle et al., , 2014Wittpahl et al., 2015). Previously, several ellagitannins, except hexahydroxydiphenoyl-glucose (HHDP-glucose) isomers, were tentatively identified in C.incanus by Wittpahl et al. (2015). ...
Article
The leaves of Cistus × incanus L. (pink rock-rose) are used as plant material rich in antioxidants by the pharmaceutical and food industry. The main components which occur in pink rock-rose are polyphenols, especially flavonoids (glycosides of flavonols) and tannins (proanthocyanidins and ellagitannins). Derivatives of flavonols and flavan-3-ols as bioactive compounds of this species were identified previously. However, the full composition of ellagitannins has not been characterized yet. In this context, the study aimed to characterize the chemical composition of pink rock-rose ellagitannins and to identify and elucidate structures of major compounds from this group. In conclusion, the new ellagitannin cistusin together with well-known terflavin A and punicalagin from C. incanus leaves were isolated. Their structures, including the gallagyl, flavogallonyl, valoneoyl, and hexahydroxydiphenoyl acyl groups, were revealed by spectroscopic evidence (HR-ESI-MS, 1D and 2D-NMR).
... These products are especially promoted for a high content and a diverse profile of phenolic compounds (including flavonol glycosides or tannins) with an associated strong antioxidant activity or other potential health-promoting effects (i.e., antitumor or anti-inflammatory effects exhibited through reduction of free radicals and oxidative stress markers) (6,7). Moreover, for the consumer it is of interest which product yields the highest concentrations of bioactive phenolic compounds (9,10). ...
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The members of Cystus genus are perenial shrubs with a well-established use in traditional medicine. Among these, C. creticus is the most popular, herbal preparations obtained from its aerial parts being recognized as antimicrobial, antitumor and anti-inflammatory agents. The present study aimed to evaluate phytochemical profile and bioactive potential of aqueous and hydroethanolic extracts of C. creticus aerial parts harvested from two different areas of Rhodes island. LC-DAD-ESI/MSn analysis revealed the presence of myricetin and quercetin glycosides as main compounds, especially in aqueous extracts, being probably responsible for their enhanced antioxidant and antimicrobial potential. On the other side, hydroethanolic preparations exerted a strong anti-inflammatory and anti-biofilm activity. Our findings suggest that the use of solvents with intermediate polarity can assure the best recovery of bioactive compounds from C. creticus, increasing the extraction yield for other non-phenolic compounds which can enhance therapeutic potential of the extract through a synergistic action.
... These changes are the result of heat treatment (baking process). Riehle, Vollmer, and Rohn (2013) reported that when preparing C. incanus beverages, decreased amounts of phenolic substances and reduced antioxidant activity are observed if an incorrect selection of brewing process parameters (brewing water, temperature, and duration) is made. Spontaneous changes in polyphenols can occur at elevated temperatures. ...
Article
The aim of the study was to use cistus extract for the production of wheat bread and determine its impact on selected physicochemical, microbiological, and organoleptic characteristics, the color of the crumb, changes in the crumb texture, polyphenol profile and the total polyphenol content. Breads with 5 and 7.5% cistus extract were characterized by lower average scores for taste and smell, compared to wheat bread. During storage (up to 5 days) the largest increase of crumb hardness was observed for wheat bread, as much as 72.89%, compared to the first day of storage, in contrast to bread with 5% cistus extract (29.03%). The replacement of water by cistus extract influenced the color of the crumb by increasing its browning index from 30.92 (standard bread) to 66.47 (7.5% cistus extract). The cistus extract contributed to an improvement of the microbiological quality of the bread. The addition of the cistus extract influenced the polyphenol content by increasing it from 8.88 (wheat bread) to 78.71 mg/100 g (breads with 7.5% cistus extract) and the total polyphenol content from 62.81 to 105.81 mg GAE per 100 g of product, compared to the wheat bread.
... Kaempferol, quercetin derivatives, myricitrin and isorhamnetin were also found in other members of the Cistus subgenus. Several authors (Barrajón-Catalán et al., 2011;Riehle et al., 2013;Tomas-Menor et al., 2013;Barros et al., 2013) reported the presence of kaempferol methylether in C. ladanifer and C. salviifolius leaf extracts. On the other hand, Orhan et al. (2013) identified naringenin and quercetin-3-O-rhamnoside in C. laurifolius extracts. ...
... It has already been described in the literature that different phenolic compounds contribute differently to the total AOA. Riehle et al. determined the AOA of the individual phenolic compounds in Cistus incanus herbal tea infusions while using HPLC-onlineTEAC and found that the individual phenolic compounds had different AOA and different proportions of the total AOA of the samples [71]. Zietz et al. and Fiol et al. analyzed kale (Brassica oleraceae var. ...
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Biofortified apples seem to be a suitable produce. In this study, different selenium forms and application levels were applied to the two apple varieties 'Golden Delicious' and 'Jonagold', grown in the years 2017 and 2018 in order to increase the selenium uptake within a typical Western diet. It was shown that the biofortification, which was performed as a foliar application implemented in usual calcium fertilization, led to significantly increased selenium contents in the fruits. Furthermore, biofortification affected the total phenolic content (TPC), the polyphenol oxidase activity (PPO), as well as the antioxidant activity (AOA), the latter measured with the two well-known assays Trolox Equivalent Antioxidant Capacity Assay (TEAC) and Oxygen Radical Absorbance Capacity Assays (ORAC). The varying selenium forms and application levels showed a differing influence on the parameters mentioned before. Higher fertilizer levels resulted in higher selenium accumulation. It was found that PPO activity fluctuates less in biofortified apples. With regard to TPC, selenate led to higher amounts when compared to the untreated controls and selenite resulted in lower TPC. AOA analysis showed no clear tendencies as a result of the selenium biofortification. In the case of 'Jonagold', a higher AOA was generally measured when being biofortified, whereas, in the case of 'Golden Delicious', only one form of application led to higher AOA. Additionally, differences in the amount of major phenolic compounds, measured with High Performance Liquid Chromatography Mass Spectrometry (HPLC-DAD-ESI-MSn), were observed, depending on the conditions of the biofortification and the variety.
... Several studies have attempted to elucidate the phenolic composition of Cistus incanus [34][35][36][37]. Viapiana et al. [20] in their earlier work assessed the phenolic profile and antioxidant capacity of aqueous extract of 15 commercially available samples of Cistus incanus, and showed that the place of the origin was the main factor in differentiating the Cistus incanus samples. ...
Article
Background: Oxidative stress and dyslipidemia play a critical role in the development of cardiovascular disease (CVD). Regular intake of polyphenol-rich diets is associated with a reduced risk of CVDs. Methods: The present study was a pilot study with 24 healthy volunteers and was designed to determine if a 12-week administration of Cistus incanus herbal tea, containing phenolic acids and flavonoids, reduces cardiovascular risk factors including oxidative stress and dyslipidemia in healthy adults. Phenolic compounds profile and antibacterial activity of Cistus incanus infusion were also measured. Results: Herbal infusion led to improvement in lipid profile by increase (D4%, p = 0.033) high-density lipoprotein cholesterol concentration and decrease triglyceride (D14%, p = 0.013) concentrations. In addition, the Cistus incanus diet was associated with decreased serum concentrations of malondialdehyde (D16%, p < 0.01) and advanced oxidation protein products (D18%, p < 0.001). Conclusions: Cistus incanus administration decreases cardiovascular risk factors including oxidative stress and dyslipidemia and this action supports the idea of using Cistus incanus tea on a daily basis as an effective dietary component for prevention of atherosclerotic CVD.
... Several studies have attempted to elucidate the phenolic composition of Cistus incanus [34][35][36][37]. Viapiana and Wesolowski [20] in their earlier work assessed the phenolic profile and antioxidant capacity of aqueous extract of 15 commercially available samples of Cistus incanus, and showed that the place of the origin was the main factor in differentiating the Cistus incanus samples. ...
... Currently, numerous manufacturers offer some Cistus herbal infusions (as "Cistus tea") in the market as useful anti-oxidant supplements to prevent chronic diseases [9]. ...
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Background: Cistus genus is widespread in the Mediterranean regions with several species and is traditionally known as a natural remedy, but few previous phytochemical researches have been conducted on Cistus species growing in Sardinia. The aim of this study is to characterize the phenolic composition and to evaluate antimicrobial activities of the extracts of C. creticus subspecies growing in Sardinia. Methods: The fresh aerial parts of the plants were extracted using acidified methanol. HPLC-DAD-ESI-MS was employed to identify the polyphenols in the obtained extracts. Antimicrobial activity was determined as Minimum Inhibitory Concentration by using an agar macrodilution method. Results: The obtained results allowed the detection of 52 phenolic compounds including phenolic acids, monomeric and dimeric flavan-3-ols, flavonol glycosides. The phenolic profiles of the three subspecies were observed to be similar, even if the relative percentages were quite different. The extracts did not exhibit any pronounced differences in their antimicrobial activities; however, it was revealed that Gram-positive bacteria are more sensitive to the Cistus extracts than Gram-negative bacteria. None of the extracts showed any noticeable action against Candida species Conclusion: We can affirm that some differences are evident between the chemical profile of polyphenols in the C. creticus subsp. creticus and the other two subspecies; however, it appears to be clear that the secondary metabolites are similar. The present study permits us to obtain preliminary information on the antibacterial and antifungal activity of methanol extracts of Cistus creticus subspecies from Sardinia.
... The relationship between polyphenol-rich food consumption and reduced possibility of being affected by some diseases has attracted increasing interest from consumers, food manufacturers and nutritional scientists [3]. In the human diet, phenolic compounds, primarily flavonoїds, phenolic acids and isoflavones are the most abundant antioxidants [4]. The estimated daily total dietary intake is thought to reach from 20 mg to 1 g [5,6]. ...
Article
Osyris alba L. (Santalaceae) is a shrub that grows wildly in southern Europe, North Africa and South-west Asia. In Algeria, the decoction of the root bark of this plant has been used since ancient times in folk medicine by the local population in the region of the mountains of Béni- Snousse (South west of Tlemcen), as a fortifying, antianaemic and as an anti-inflammatory agent. The aim of this work was to evaluate the antioxidant activity of the phenolic compounds of the root by using DPPH, FRAP, TAC methods. Determination of the phenolic profile of the root extract was assessed using HPLC-DAD technique (High Performance Liquid Chromatography-Diode Array Detection). While the determination of total fatty acid composition of the root oil was performed using Gas Chromatography (GC-FID). From the results, the total poly-phenol extract of the root bark has shown the highest antioxidant power which exceeds the standard, namely, ascorbic acid and Trolox. The chromatographic analysis of the total poly-phenol extract has found that the Gallic acid and Quercetin are the major compounds. These results demonstrate that the phenolic compounds of Osyris alba root bark have a great potential as sources for natural health products. Gaseous Chromatography Assay of the oil has revealed the presence of two groups of fatty acids: arachidic acid (C20:0) and linoleic acid (C18: 9.12) known for its pro-inflammatory effect against oleic acid C18:1, linolénic acid C18: 9.12.15, and eicosatrienoic acid (ETA) C20:3 which are known for their pro-anti-inflammatory effect. For this reason, we need to test the effect of this oil on inflammatory models.
... Ten compounds (1 -10) were isolated from the PE and EtOAc extracts of the whole plant of E. atlantica with the aid of various chromatographic techniques, namely, vacuum liquid chromatography (VLC), column chromatography (CC), and thin layer chromatography (TLC). These compounds were identified using 1D and 2D NMR and ESI-MS analysis and by comparison with literature data as follows: 3b-hydroxycycloart-25-en-24-hydroperoxyde (1) [18], 24-methylenecycloartanol (2) [3], cycloeucalenol (3) and obtusifoliol (4) [6], b-sitosterol (5) [19], daucosterol (6) [20], quercetin-3-O-L-rhamnoside (7) [21], (-)-epicatechin (8) [22], methyl gallate (9) [23] and phloroacetophenone-4-O-b-D-glucopyranoside (10) [24]. Figure 1 shows the chemical structures of compounds 1-10. ...
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A phytochemical study of crude extracts obtained from Euphorbia atlantica Coss. led to the isolation and structure identification of ten known compounds by spectroscopic analysis including 1D and 2D NMR techniques (¹H, ¹³C, DEPT, COSY, HSQC, HMBC and NOESY), mass spectrometry (ESI-MS), measurements of optical rotation [α]D, and by comparison with the literature data. The total phenolic content was estimated and the antioxidant activities of the petroleum ether and ethyl acetate extracts were evaluated using seven different methods, namely scavenging of the free radicals (ABTS and DPPH), ferric reducing antioxidant power (FRAP), total antioxidant capacity by phosphomolybdate assay (PPM), cupric reducing antioxidant capacity (CUPRAC), and metal chelate and ferrous ion chelating activities. The antibacterial activity of extracts was estimated by the agar disk diffusion assay against four bacterial strains including Staphylococcus albus, Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 35218 and Enterobacter sp.
... *Different letters in superscripts in the same column indicate that the mean difference is significant at the level of 0.05 per LSD (mean ± SD, n = 4). In a brewing process, several physicochemical changes may or may not favor the appearance of antioxidant substances derived from more abundant polymeric compounds such as higher molecular weight polyphenols (36). The content of antioxidant metabolites is presented in table 3, where the total polyphenols decreased significantly in MIX and CAL. ...
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Vaccinium meridionale produces fruits with a high content of anthocyanins and polyphenols with great antioxidant capacity. Objective: produce vinegar from V. meridionale alcoholic beverages and to determine the content of bioactive antioxidant compounds, antioxidant capacity, and cytotoxic activity on colorectal cancer cells. Methods: Wine and vinegar samples were obtained by fermentation of V. meridionale berries juice, using three extractive processes: mechanical maceration (MAC), preheating to 80 °C (CAL) and a combination of both (MIX). During acetic fermentation, titratable acidity and acetic acid content were evaluated. Fermentation progress was recorded and compared by measuring the antioxidant potential by DPPH, FRAP, and ORAC. Polyphenols, anthocyanins and hydroxycinnamic acids were quantified. Finally, the antiproliferative activity of vinegar was evaluated in SW480 colon cancer cells. Results: In acetic fermentation, yield and productivity were independent of extraction, indicating that they do not affect the biotransformation of alcohol into vinegar. The alcoholic beverages showed the highest antioxidant activity; after acetic fermentation, a decrease in antioxidant potential was observed in all three extractive processes valuated. The different vinegar obtained by CAL and MIX, showed the highest values of antioxidant activity, polyphenols, and anthocyanins. The inhibition of the antiproliferative activity of vinegar was dose-dependent and showed an IC50 of 536 μg/mL. Conclusions: The vinegar prepared from V. meridionale berries presented an outstanding antioxidant and antiproliferative activity. The reason is the contents of bioactive compounds and their antioxidant power, which may contribute to chemoprevention in secondary cancer prevention.
... Cistus creticus L. [16]), which belongs to the Cistaceae family and is well recognized for its therapeutic activity. This medicinal plant is very popular in its natural habitats: eastern parts of the Mediterranean basin (including Greek Islands) and the Middle East [17], and it has been traditionally used as an anti-inflammatory, anti-allergic, antiulcerogenic, wound-healing, antimicrobial and cytotoxic agent [18]. Antimicrobial potential of the non-polar organic [19][20][21], methanolic [22] and the aqueous methanolic [23,24] extracts as well as essential oil [19,25,26] derived from C. incanus leaves and flowers had been investigated in a number of studies carried out against the Gram positive and Gram negative bacterial strains. ...
... Free radicals may contribute to the development of serious diseases such as cancer [4]. Cistus infusions are rich in phenolic acids and flavonoids (rosmarinic acid, quercetin, catechins, gallic acid) as a result of which they produce strong antioxidant effects [5]. During the Covid-19 epidemic, new antiviral drugs are being sought. ...
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This study investigates the effects of various drying methods applied to leaves of Cistus creticus L. on the contents of polyphenols and the composition of the volatile fraction. The following four drying methods were used: convection drying at a temperature of 40 °C (CD 40 °C), 50 °C (CD 50 °C), and 60 °C (CD 60 °C); vacuum-microwave (VMD 240 W); combined drying, involving convection pre-drying (50 °C) and vacuum-microwave (240 W) finish drying (CPD-VMFD) as well as freeze-drying (FD). Polyphenols in the dried leaves were determined using chromatography-photodiode detector-quadrupole/time of flight-mass spectrometry (UPLC-PDA-Q/TOF-MS). The contents of odoriferous substances in the dry material were determined by means of head space-solid phase microextraction (HS-SPME) with the use of a gas chromatograph (GC). Thirty-seven polyphenol components including 21 flavonols, eight flavan-3-ols, and eight hydrolyzed tannins in dry Pink Rock Rose material were found for the first time. The highest contents of polyphenols, totaling 2.8 g/100 g-1 dry matter (d.m.), were found in the samples subjected to the CPD/VMFD drying method. Pink Rock Rose subjected to this drying method was characterized by large quantities of odoriferous compounds, mainly eugenol, thymol, and carvacrol, which contribute to its antiseptic properties. By using CPD/VMFD methods, it is possible to obtain fine quality dry material from the leaves of C. creticus.
... Cistus creticus L. [16]), which belongs to the Cistaceae family and is well recognized for its therapeutic activity. This medicinal plant is very popular in its natural habitats: eastern parts of the Mediterranean basin (including Greek Islands) and the Middle East [17], and it has been traditionally used as an anti-inflammatory, anti-allergic, antiulcerogenic, wound-healing, antimicrobial and cytotoxic agent [18]. Antimicrobial potential of the non-polar organic [19][20][21], methanolic [22] and the aqueous methanolic [23,24] extracts as well as essential oil [19,25,26] derived from C. incanus leaves and flowers had been investigated in a number of studies carried out against the Gram positive and Gram negative bacterial strains. ...
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The main aim of this study was to detect and identify antibacterial components of fraction I derived from eleven commercial C. incanus herbal teas. Fraction I obtained by a well-established phytochemical protocol of a multi-step extraction was expected to contain flavonoid aglycons alone. Antibacterial profile of fraction I was demonstrated by means of thin-layer chromatography - direct bioautography (TLC-DB) using a Gram positive B. subtilis and a Gram negative A. fischeri strain. Six chromatographic zones of fraction I exhibited a well pronounced antibacterial potential. In qualitative terms, a good agreement was observed among chromatographic fingerprints and the corresponding bioautograms of the eleven samples. The compounds isolated from the six zones were analyzed by HPLC- diode array detector (DAD)-electrospray ionization (ESI)-MS. High numerical m/z values valid for certain constituents of these isolates suggested that some selected antibacterial components are, unexpectedly, flavonoid glycosides. In order to confirm this suggestion, three independent HPTLC methods (multi-development on amino phase and two two-dimensional developments on silica gel phase) were devised to in situ hydrolyze flavonoid glycosides and then separate and visualize the liberated glucose and some other building blocks of the zones' components. Additionally, the sensitivity of glucose detection with p-aminobenzoic acid reagent was enhanced by paraffin. In that way, the presence of the kaempferol glycosides (and not only the aglycones alone) in fraction I was confirmed. Beside kaempferol, p-coumaric acid as a building block unit was shown by HPLC-DAD-MS analysis of the hydrolyzed isolates. Results proved apigenin, kaempferide and acylated kaempferol glycosides (cis- and trans-tiliroside and their conjugates with p-coumaric acid) to be antibacterial components of fraction I. Because isomers of the coumaric acid conjugated tiliroside were detected only in fraction I and not in the crude C. incanus extract, they are regarded as artifacts produced through fractionation.
... Phytochemical profile of different Cistus species aqueous extracts reveals their polyphenolic profile, having flavonoids, phenolic acids, and ellagitanins as their main constituents [2,3,6,8,10,15,23,26,31,32,[35][36][37][38][39][40][41][42][43][44]. ...
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Aqueous extracts of two Cistus species wild growing in Croatia—Cistus creticus (CC) and Cistus salviifolius (CS)—have been assessed with UPLC-MS/MS, showing 43 different phytochemicals, with flavonol glycosides: myricetin-3-hexoside and myricetin-rhamnoside, predominate ones in CC and myricetin-3-hexoside in CS. Antioxidant potential tested with the FRAP method showed no difference between CS and CC aqueous extracts, while higher phenolic content of CC comparing to CS, determined with a Folin–Cicolateu reagent correlated to its higher antioxidant capacity observed by the DPPH method. Both extracts were assessed for antimicrobial activity, using disc-diffusion and broth microdilution assays, targeting the opportunistic pathogens, associated with food poisoning, urinary, respiratory tract, blood stream and wound infections in humans. Antimicrobial assays revealed that fungi were in general more sensitive to both Cistus aqueous extracts, comparing to the bacteria where two extracts showed very similar activity. The most potent activity was observed against A. baumannii for both extracts. The extracts were tested on human lung cancer (A549) cell line using the MTT assay, showing very similar antiproliferative activity. After 72 h treatment with CC and CS aqueous extracts in concentration of 0.5 g/L, the viability of the cells were 37% and 50% respectively, compared to non-treated cells.
... Decoction is preferred method for brewing herbal tea from the tougher, denser herb materials such as roots, bark, and berries. Using water with a high degree of total hardness results in lower content of phenolic compounds, which is also associated with significant decreased antioxidant capacities [31]. Other conventional domestic extraction methods include maceration, where powdered crude herb material is mixed with solvent (usually water-ethanol mixture) and digestionmacerated herb with solvent is gently heated. ...
... The system was controlled by ClarityChrom 3.0 software (Knauer GmbH, Berlin, Germany). A binary gradient system based on Riehle et al. (2013) with eluent (A) 0.1% formic acid in water, eluent (B) 0.1% formic acid in acetonitrile was conducted on a Luna® 5 μm C18 100 Å (150 × 3.00 mm) column equipped with a C18 security guard (4 × 3.00 mm), both from Phenomenex Inc. (Aschaffenburg, Germany). Gradient elution was used for methanolic SPE eluates: 5% B isocratic (0-2 min), 5-10% B (2-6 min), 10-30% B (6-45 min), 30-95% B (45-55 min), 95% B isocratic (55-60 min), 95-5% B (60-65 min), and 5% isocratic (65-75 min). ...
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Mycorrhizal symbiosis is known to be the most prevalent form of fungal symbiosis with plants. Although some studies focus on the importance of mycorrhizal symbiosis for enhanced flavonoids in the host plants, a comprehensive understanding of the relationship still is lacking. Therefore, we studied the effects of mycorrhizal inoculation of onions (Allium cepa L.) regarding flavonol concentration and the genes involved in flavonol biosynthesis when different forms of nitrogen were supplied. We hypothesized that mycorrhizal inoculation can act as a biotic stress and might lead to an increase in flavonols and expression of related genes. The three main quercetin compounds [quercetin-3,4′-di-O-β-d-glucoside (QDG), quercetin-4′-O-β-d-glucoside (QMG), and isorhamnetin-4′-O-β-d-glucoside (IMG)] of onion bulbs were identified and analyzed after inoculating with increasing amounts of mycorrhizal inocula at two time points and supplying either predominantly NO3⁻ or NH4⁺ nitrogen. We also quantified plant dry mass, nutrient element uptake, chalcone synthase (CHS), flavonol synthase (FLS), and phenyl alanine lyase (PAL) gene expression as key enzymes for flavonol biosynthesis. Inoculation with arbuscular mycorrhizal fungi (highest amount) and colonization at late development stages (bulb growth) increased QDG and QMG concentrations if plants were additionally supplied with predominantly NH4⁺. No differences were observed in the IMG content. RNA accumulation of CHS, FLS, and PAL was affected by the stage of the mycorrhizal symbiosis and the nitrogen form. Accumulation of flavonols was not correlated, however, with either the percentage of myorrhization or the abundance of transcripts of flavonoid biosynthesis genes. We found that in plants at late developmental stages, RNA accumulation as a reflection of a current physiological situation does not necessarily correspond with the content of metabolites that accumulate over a long period. Our findings suggest that nitrogen form can be an important factor determining mycorrhizal development and that both nitrogen form and mycorrhizas interact to influence flavonol biosynthesis.
... The content of 5 was the highest in flowers (S0), with a concentration of ∼40 µg/100 mg −1 DW, and it decreased, during fruit development, down to ∼1.9 µg/100 mg −1 DW in S3 phase (Supplementary Figure 4). F3Os EC, C, EGC, and GC have been previously reported for C. incanus (Riehle et al., 2013). ...
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Cistus creticus L. subsp. creticus (rockrose) is a shrub widespread in Greece and the Mediterranean basin and has been used in traditional medicine as herb tea for colds, for healing and digestive hitches, for the treatment of maladies, as perfumes, and for other purposes. Compounds from its flavonoid fraction have recently drawn attention due to antiviral action against influenza virus and HIV. Although several bioactive metabolites belonging to this group have been chemically characterized in the leaves, the genes involved in their biosynthesis in Cistus remain largely unknown. Flavonoid metabolism during C. creticus fruit development was studied by adopting comparative metabolomic and transcriptomic approaches. The present study highlights the fruit of C. creticus subsp. c reticus as a rich source of flavonols, flavan-3-ols, and proanthocyanidins, all of which displayed a decreasing trend during fruit development. The majority of proanthocyanidins recorded in Cistus fruit are B-type procyanidins and prodelphinidins, while gallocatechin and catechin are the dominant flavan-3-ols. The expression patterns of biosynthetic genes and transcription factors were analyzed in flowers and throughout three fruit development stages. Flavonoid biosynthetic genes were developmentally regulated, showing a decrease in transcript levels during fruit maturation. A high degree of positive correlations between the content of targeted metabolites and the expression of biosynthetic genes indicated the transcriptional regulation of flavonoid biosynthesis during C. creticus fruit development. This is further supported by the high degree of significant positive correlations between the expression of biosynthetic genes and transcription factors. The results suggest that leucoanthocyanidin reductase predominates the biosynthetic pathway in the control of flavan-3-ol formation, which results in catechin and gallocatechin as two of the major building blocks for Cistus proanthocyanidins. Additionally, there is a decline in ethylene production rates during non-climacteric Cistus fruit maturation, which coincides with the downregulation of the majority of flavonoid- and ethylene-related biosynthetic genes and corresponding transcription factors as well as with the decline in flavonoid content. Finally, functional characterization of a Cistus flavonoid hydroxylase (F3′5′H) was performed for the first time.
... Aqueous extracts of the aerial parts of these plants have been demonstrated to exert intense antioxidant capacities that can be attributed to their high polyphenol contents. [21][22][23] ...
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The Cistaceae family is well represented in Sardinia, and the Cistus genus is widely used in traditional medicine. Nowadays only few studies have been performed on this genus vegetating in Sardinia in spite of its ethnobotanical importance. Moreover, in the past there have been conflicting opinions among botanists for the exact assignment of the species growing in Sardinia. We started several years ago to carried out studies on this genus and in the present study was to evaluate the in vitro activity of several samples of Cistus salvifolius L., Cistus monspeliensis L., and Cistus albidus L. collected in Sardinia as antimicrobial agents against Escherichia coli , Staphylococcus aureus , and four Candida species and their antioxidant activity using DPPH, ABTS, and FRAP assays. Furthermore, the phenolic content and composition of the extracts were first evaluated. Using statistical multivariate analysis on the complete metabolomics profile of all Cistus species growing wild in Sardinia, we confirmed the botanical classification, and we observed an interesting correlation between metabolomics profile and antioxidant activity.
... Riehle has proven a significant decrease of different groups of phenolic compounds and flavonoids when brewing the commercially available C. incanus infusions with different water used at various conditions [76]. The profile of phenolic compounds from C. incanus pollen was different between nonhydrolyzed and hydrolyzed. ...
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Resistance to drugs is reaching alarming levels and is placing human health at risk. With the lack of new antimicrobials drugs, infectious diseases are becoming harder to treat. Hence, there is an increasing awareness of active phytochemicals with therapeutic functions. The tremendous research interest on the Cistus L. genus includes numerous plants used in traditional medicine by people living around the Mediterranean Sea, also resulted in some interesting discoveries and written literature. This review aimed at gathering scientific literature about Cistus species, describing phytochemical profiles and the various pharmacological activities. We also extensively reviewed the antimicrobial activities, including antiviral, antiparasitic, antifungal, and antibacterial potentials of Essential Oils (EO), raw extracts as well as isolated compounds. Mechanisms of action along with methods used are also investigated in this review. Considering the findings of the Cistus species extracts, this genus offers an adequate reserve of active phytochemicals since many have been used to create drugs. Therefore, this review work can serve society by providing a global view on Cistus L. sp. regarding pharmacological potentials and their chemical profiles.
... The extract contained the following procyanidins: gallocatechin, gallic acid, gallocatechin trimer, gallocatechin-(4α-8)-catechin, epicatechin-3-gallate, catechin and epicatechin. Barrajón-Catalán et al. [32] and Riehle et al. [33] identified flavan-3-ols in C. incanus extracts, and found various flavanols, especially the compounds myricetin, quercetin, and kaempferol. Wittpahl et al. [19] also identified tannins: punicalin isomers, punicalagin isomers, and cornusin B. ...
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This study evaluates the effects of polyphenolic extract of Cistus incanus, lycopene dye from tomatoes, and betanin dye from red beet on selected parameters of model meat products with reduced nitrate contents. The polyphenolic composition and activity of the C. incanus extract was analyzed, revealing the presence of elagotannins, flavanols, and glycosylated flavanols. We studied the effects of the extract and dyes as well as of mixtures of the extract and dyes on the growth of bacteria characteristic of the meat environment: E. coli, S. enterica, P. fragi, L. monocytogenes, B. thermosphacta, and L. sakei. We studied the effects of the extract and dyes on the lipid oxidation, color, and microbiological quality of pork sausages with reduced nitrate content over 28 days of storage. During storage, the amounts of malon dialdehyde reduced, which indicates that the extract and dyes exhibited antioxidant activity and slowed lipid oxidation in the sausages. An increase in red color was also observed in the sausages with natural additives, despite their decreased nitrate content. It was found that the C. incanus extract combined with coloring agents positively influenced the selected parameters of the analyzed pork sausages.
... Cistus incanus and other species of Cistaceae family are used in the Mediterranean folk medicine since hundreds of years as a general remedy for treatment various diseases [1]: skin diseases, rheumatism, fever and diarrhea. The small evergreen shrub is widespread in Strandja Mountain, Bulgaria [2], but it has not been used as a natural remedy neither in the past nor now. ...
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Present study investigates the effect of storage (at room temperature and at a frozen state) of Cistus incanus leaves and its hard-coated seeds on the total polyphenol content and the antioxidant capacity in view of the extraction carried out in 50 % ethanol-in water solution. A correlation between the polyphenol content and the antioxidant activity of the leaves stored at room temperature is elucidated. The frozen stored material generates better extraction efficiency and keeps a very high antioxidant activity. This investigation demonstrates that Cistus incanus from Strandja Mountain, Bulgaria is an important source of polyphenols and antioxidant activity. The latter is present in leaves stored for a couple of years. The results from this study contribute to better understanding the extraction process of this non-traditional Bulgarian herb.
... Therefore, 5.56 times increase in TWSS content in the treated samples indicates that stir-fry processing is more effectual technique for phytochemicals extraction from A. nitida leaf in daily tea model. Consequently, stirfry, cooking or grinding processing cause cell wall degeneration and morphological changes, which make phytochemicals more accessible (Lemmens et al., 2013;Riehle et al., 2013). ...
Article
Adinandra nitida tea (Shiyacha) is a well-known resource of functional foods with many healthful features. Effect of stir frying on phenolics, aromatic compounds, cellular antioxidant and antiproliferative activities in A. nitida tea was investigated. Stir-fried samples depicted a significant increase in total water-soluble solid, phenolics and flavonoids contents, respectively. In stir-fried treated samples, main compounds were higher than in corresponding untreated samples. Similar trend was observed in aromatic compounds. Hydrophilic peroxyl radical scavenging capacity and oxygen radical absorbance capacity were enhanced immensely in the treated samples. Furthermore, cellular antioxidant activities of treated samples were higher than those of untreated samples. Stir-fried samples exhibited higher antiproliferative activity on HepG2 cells, whereas an lack in untreated samples. These findings suggest that stir frying could be an effective technique to improve A. nitida tea quality, and support that A. nitida tea could act as a potential functional food against intracellular oxidative stress and inhibitor of liver cancer.
... In addition to above mentioned terpenoids, phenolic compounds are also constituents of C. creticus resin and leaves extracts ( Table 2). As is already indicated by numerous studies, plants belonging to the genus Cistus are good source of polyphenols, mainly flavonoids and tannins (Güvenç et al., 2005;Barrajón-Catalán et al., 2010, 2011Riehle et al., 2012;Barros et al., 2013;Tomás-Menor et al., 2013;Wittpahl et al., 2015;Gori et al., 2016;Viapiana et al., 2017;Zalegh et al., 2021). Variable gallic acid-derived hydrolysable ellagitannins were previously identified in leaves of some Cistus species, including C. albidus, C. clusii, C. crispus, C. creticus, C. ladanifer, C. laurifolius, C. monspeliensis, C. populifolius, and C. salviifolius (Santagati et al., 2008;Barrajón-Catalán et al., 2011). ...
Article
Cistus creticus subsp. creticus is a shrubby Mediterranean plant used since ancient times in folk medicine for the treatment of different diseases. C. creticus extracts and resin contain different types of secondary metabolites, such as terpenoids (predominantly labdane type diterpenoids), and phenylpropanoids. Growth conditions seem to influence the content of labdane-type diterpenes and flavan-3-ols in leaves of C. creticus subsp. creticus. Histochemical staining of leaves’ trichomes and comprehensive phytochemical characterization of resin, leaves and their exudates, indicated that long-stalked capitate trichomes of C. creticus subsp. creticus, grown both in vitro (IV) and in greenhouse (GH), are capable of producing bioactive oleoresin-related terpenoids and phenylpropanoids compounds. Bioactivity-guided approach was implemented in search for the major antibacterial compound in C. creticus resin against two Gram-negative (Escherichia coli and Pseudomonas aeruginosa) and two Gram-positive bacteria (Bacillus cereus and Micrococcus flavus). Bioautographic assay on TLC plates with separated components of Cistus resin extract, revealed a pronounced zone of microbial growth inhibition, corresponded to a highly active compound with Rf values of 0.45, structurally characterized and identified as ent-3β-acetoxy-13-epi-manoyl oxide. This finding opens the route for focusing on isolation and functional characterization of genes involved in the biosynthesis of ent-3β-acetoxy-13-epi-manoyl oxide and its precursor ent-3β-hydroxy-13-epi-manoyl oxide, with the aim to establish sustainable in vitro biotechnological protocols for its large-scale production in homologous and heterologous plant and microbial hosts.
... Okuda., et al. have mentioned that rosmarinic acid was degraded when it is dried under direct sunlight, and in the oven at 60 and 80 o C and Mueller-Harvey has reported that some phenolic compounds decompose rapidly in direct sunlight [33,34]. Recent works also demonstrated that the temperature affects the stability of phenolic compounds in herbal infusions [35]. ...
Article
This study was carried out to evaluate the antioxidant properties of Greek endemic Cistus creticus L. (rock rose) bee pollen and define its phenolic compounds. In the framework of our scientific studies on Greek bee keeping products, we report herein our research on three Greek bee pollen samples from Cistus. Their pollinic spectra were obtained by Louveaux's quantitative microscopical analysis and it showed that one of them had Cistus sp. (Cistaceae) as abundant pollen (together with low percentage of Brassica sp. (Cruciferae). Throughout the chemical analysis of the extracts, several secondary metabolites of flavonoid structure have been identified as major components. Specifically, quercetin-7-rhamnoside (1), quercetin-3-neohesperidoside (2), kaempferol-3- neohesperidoside (3), myricetin-3-neohesperidoside (4), kaempferol-3-glucoside (5) and quercetin-3-glucoside (6) have been isolated and their structures were elucidated on the basis of spectral evidence. Moreover, the total phenolic and flavonoid content was estimated and the free radical scavenging activity was determined by DPPH and ABTS assays. The antimicrobial activity of the extracts was tested against six Gram-positive and -negative bacteria and three pathogenic fungi, and the butanol extract showed a very interesting broad antimicrobial profile (MIC 1.98·10⁻³ - 2.98·10⁻³ mg/ml) against all the assayed microorganisms.
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Considering the potential of applying grape skin extract (GSE) as functional ingredients in products that must be thermally processed, the aim of this study was to evaluate the stability of individual polyphenols in grape skin extracts submitted to heating at different temperatures. Polyphenolic compounds were extracted by applying 20% aqueous ethanol containing 1% acetic acid for 1 h at 50 °C on a magnetic stirrer. The obtained extract was divided into aliquots and submitted to heating at different temperatures for a various time. The content of individual phenolic compounds in all incubated extract was determined by the HPLC method. All studied compounds were very stable during heating at 40 °C. Among analyzed anthocyanins, diglucosides were more stable than corresponding monoglucosides. Gallocatechin and procyanidins B1 and B2 contents were decreased, while catechin and epicatechin contents were increased during thermal treatments. At both incubation temperature contents of caftaric and coutaric acid were decreased, while in the same time contents of caffeic and coumaric acids were raised which could be due to hydrolysis. A significant increase of gallic, protocatechuic, vanillic, and syringic acid contents was due to thermal degradation of delphinidin-3-O-glucoside, cyanidin-3-O-glucoside, peonidin-3-O-glucoside, and malvidin-3-O-glucoside, respectively. trans-Piceid showed high stability toward thermal treatments.
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We describe the application of Cistus incanus extract as a source of reducing, structure-directing and stabilizing agents in the fabrication of gold nanoparticles (GNPs) from tetrachloroauric acid solution. The synthesis resulted in the formation of nanostructures with highly extended surface area, resembling the shape of popcorn. Various ratios of plant extract volume to chloroauric acid volume were investigated in order to obtain nanoparticles with desired shapes having the narrowest size distribution. The synthesized nanoparticles were characterized using UV–Vis absorption spectroscopy, transmission electron microscopy (TEM) and atomic force microscopy (AFM). Multiphoton-excited luminescence (MPL) properties of plant extract synthesized popcorn-shaped gold nanoparticles were examined in comparison with gold nanostars synthesized chemically. The obtained results suggest that the GNPs synthesized using cistus extract may be useful imaging agents for multiphoton microscopy.
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Cistus incanus L. (CI) has been proposed as an innovative functional supplement of food products, and hence the present study aimed to evaluate the effect of the addition of dried CI on the properties of bread. Bread was prepared from white wheat flour supplemented with the addition of 1%, 2%, 3%, 4%, and 5% of ground CI. After the completion of baking process, various characteristics of the obtained bread product, such as yield, volume, porosity, acidity, color, and texture, were evaluated. In addition, total phenolic content (TPC), ABTS radical scavenging activity, CHEL chelating power, and ability to quench OH∙ radicals were measured. The results showed that the addition of CI to bread caused a reduction in the volume of bread, but texture of the crumbs was acceptable. Acidity and moisture content of bread were found to be increased following CI enrichment. Significant changes in the ash content and the color of bread crumbs were also observed. Bread incorporated with CI was characterized by significantly higher TPC and much higher antioxidant activity, as measured by ABTS, CHEL, and OH∙ radicals, compared to control bread. Supplementation of bread with 3% CI produced a product with desirable characteristics which was also favored by consumers.
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Scientific observations state that stingless bee honey (Meliponinae) contains a high moisture content (>20% w/w), which contributes to the accelerated fermentation and degradation of this honey. As a strategy to minimize this problem, the use of a thermal treatment may be an option. Therefore, the present study aimed to apply in Tetragonisca angustula honey, temperatures between 52 and 71 °C, with times varying from 0.24 to 470 min and to observe the effect of thermal processing in the parameters: moisture, free acidity, pH, diastase activity, soluble solids, conductivity fructose, glucose, sucrose, 5-hydroxymethylfurfural, individual phenolic compounds, and antioxidant capacity. The results showed that the physicochemical profile of honey was minimally altered after thermal processing, highlighting 5-hydroxymethylfurfural, which was not detected in the samples after heating. In the investigation of individual phenolic compounds, 14 compounds were found in fresh honey. This profile was altered after thermal processing, showing an increase in the concentration and emergence of new compounds (isoquercetin and rutin). Such results suggest the conversion of glycosides to aglycones, which may have positively reflected the increase in antioxidant capacity. Thus, it is possible that the thermal processing is applied to the Tetragonisca angustula honey without causing major damage to its quality.
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Epidemiological studies have related berry intake to healthiness, which has been mainly associated with the polyphenolic content and the antioxidative properties of raw fruits. However, the digestion process can affect antioxidant release (bioaccessibility) and absorption (bioavailability) from fruit food matrices (i.e., digestibility), which also depend on their dietary fiber content, which together determine the potential health benefits of berry species. In this study, digestibility of strawberry, raspberry and blueberry phenolic compounds, was evaluated after in vitro digestion and compared to antioxidant content and capacity of their raw fruits for a more reliable assessment of their potential healthful effects. These berry species also differed in their fruit dietary fiber content. The polyphenolic profiles of fruits were quantified using spectrophotometry and HPLC. Results showed no consistency between antioxidant content and capacity of raw and digested fruits in the three berries. Blueberry showed the highest antioxidant capacity (AC) associated with higher total phenolic content in raw fruits whereas, after digestion, strawberry (with a lower dietary fiber content), showed the highest total phenolic content and AC in the bioavailable fractions (‘AC-bioavailable’). These results suggested that ‘AC-bioavailable’ may be an useful index to select for wholesomeness genotypes within berry breeding programs.
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The genus Scorzonera contains important plants as traditional drugs and foods. In this sense, the aim of the present study was to determine the chemical composition, antioxidant activity and enzyme inhibitory effects of the root and aerial part of Scorzonera hispanica L. (S. hispanica) extracts. The antioxidant activities were evaluated using ferric reducing antioxidant power (FRAP), cupric reducing antioxidant capacity (CUPRAC), 1,1-diphenyl-2-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid (ABTS), metal chelating and phosphomolybdenum assays and the enzyme inhibitory properties were assessed against acetyl- (AChE) and butyryl-cholinesterase (BChE), tyrosinase, α-amylase and α-glucosidase. The results showed that the methanolic and ethyl acetate extracts possessed the highest phenol and flavonoid contents. The methanolic aerial part extract represented the highest antioxidant properties (FRAP: 58.41±1.55; CUPRAC: 126.18±0.94; DPPH: 47.92±0.07; ABTS: 71.69±0.03 mg Trolox equivalent (TE)/g) compared to the root extracts. The root extract significantly depressed AChE (2.64±0.02 mg galantamine equivalent (GALAE)/g), BChE (5.36±0.45 mg galantamine equivalent (GALAE)/g), tyrosinase (60.36±0.23 mg kojic acid equivalent (KAE)/g), α-amylase (0.61±0.01 mmol acarbose equivalent (ACAE)/g) and α-glucosidase (0.82±0.01 mmol acarbose equivalent (ACAE)/g) enzymes. Liquid chromatography hyphenated with photodiode-array detection and tandem electrospray ionization mass spectrometry (LC-DAD-MSⁿ) analysis revealed phytochemical fingerprint of the two part of the plant and the most abundant constituents were rutin and orientin for aerial parts, 3,5 and 4,5-dicaffeoyl quinic acids for roots respectively. This is the first report gathering scientific data on antioxidant, enzyme inhibitory activities and phytochemical composition of S. hispanica. Thus, this research can be used as one methodological starting point for further investigation on this plant.
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The Inga genus comprises approximately 300 species that can be found from Mexico to northern Argentina. In folk medicine, Inga species are used to treat various diseases. The species Inga laurina is widely found in the Brazilian flora; however, there are few studies about its biological activity and chemical composition. The main purpose of this study was to identify and isolate the chemical constituents of Inga laurina barks and to evaluate the antifungal and cytotoxic activities. The total content of phenolics, proanthocyanidins, and flavonoids from the barks of Inga laurina were performed by spectrophotometric methods and the ethyl acetate (EAF) and n-butanol (BF) fractions showed the best results. Eleven compounds were identified in EAF by HPLC-ESI(−)-MS/MS, which showed good antifungal activity with MIC values of 23.4 and 46.8 μg mL⁻¹, evaluated by broth microdilution method. Five new compounds of the genus Inga were isolated for the first time. Three of these compounds were isolated and reported on the literature for the first time: a proanthocyanidin B-type, gallocatechin-(4α→8)-4’-O-methylgallocatechin (XI) and two proanthocyanidins A-type, gallocatechin-(2→O→7,4→8)-4’-O-methylgallocatechin (XII) and gallocatechin-3-O-galloyl-(2→O→7,4→8)-4’-O-methylgallocatechin (XIII). The chemical study of the plant bark showed that this species is rich in phenolic compounds and it has great potential for the discovery of new bioactive compounds.
Thesis
Cistaceae family is widespread in the Mediterranean regions with several species and istraditionally known as a natural remedy. Cistus genus is present in Sardinia with populations of C.monspeliensis, C. salvifolius, C. albidus and C. creticus subspecies : C. creticus subsp. creticus, C.creticus subsp. corsicus and C. creticus subsp. eriocephalus, but few previous phytochemicalresearches have been reported on Cistus species growing in Sardinia.The aim of this research is to characterize the secondarymetabolites in extracts of differentspecies of Cistus in Sardinia and to evaluate antimicrobial and antioxydant activities. The freshaerial parts of the plants were extracted by using hydro distillation for essential oils and severaltraditional solvent s for the phenolic compounds.The chemical characterization of extracts has beenrealized by means of different chromatographic techniques such as GC/MS, HPLC DAD ESI MSand CL UHP SM/SM. Antimicrobial activity was determined as Minimum Inhibitory Concentra tionby using an agar macrodilution method. Antioxidant activity has been measured by using DPPHassay and it has been verified with EPR.A comparative analysis on the composition of essential oils showed the existence of six differentprofiles. C. cretic us subsp. eriocephalus showed a high amount of manoyl oxide and its isomer. C.salvifolius has pointed out the group of labdans; another consistent percentage is made ofperfumed molecules as ionone and its derivate. Several linear hydrocarbons were produc ed by C.monspeliensis, and the heneicosane was the most represented element. In C. albidus no labdanetype diterpenes were identified. Analysis of C. creticus subsp creticus revealed several oxygenatedsesquiterpenes and labdane type diterpenes, especiall y manoyl oxide. C. creticus subsp. corsicuswas qualitatively very similar to C. creticus subsp. creticus, notably concerning the labdane typecompounds. The analysis of the seven essential oils of Cistus creticus subsp. eriocephalus showinteresting chara cteristics and they would appear divided in two groups with different metabolicprofiles. Among solvent extracts the obtained results allowed the detection of several phenoliccompounds including phenolic acids, monomeric and dimeric flavan 3 ols, flavonolglycosides.They are characterized by a hight percentage of rosmarinic acid and derivatives and ofquercitin and derivatives. C. salvifolius is quantitatively most rich of phenolic compounds. Theextracts exhibited any pronounced differences in their anti microbial activities and revealed thatGram positive bacteria are more sensitive to the Cistus extracts than Gram negative bacteria.None of the extracts showed any noticeable action against Candida species. The extracts showedthat Cistus plants of Sardin ian origin have a greater antioxidant activity.
Chapter
Z surowców ekologicznych, tj. szynki wieprzowej i słoniny, przygotowano sześć wariantów kiełbas: dwie próby kontrolne (Kd50 i Kd100) o zróżnicowanym dodatku NaNO2 (odpowiednio 50 i 100 mg/kg) oraz cztery próby badawcze: Kd50-O1 i Kd50-O2 (zawierające po 50 mg NaNO2/kg i 1 g lub 2 g liofilizatu z ostropestu plamistego/kg farszu) oraz Kd100-O1 i Kd100-O2 (zawierające po 100 mg NaNO2/kg i 1 g lub 2 g liofilizatu z ostropestu plamistego/kg farszu). Kiełbasy badano przez 12 tygodni, tj. po zakończeniu dojrzewania produkcyjnego (w 15°C przez 3 tygodnie) oraz po zakończeniu dojrzewania poprodukcyjnego w opakowaniach próżniowych (w 4°C, przez kolejne 9 tygodni). Określano wartość pH, aktywność wody, stabilność oksydacyjną (TBARS), trwałość barwy oraz jakość mikrobiologiczną wyrobów. Stwierdzono dodatnią korelację pomiędzy wyższym dodatkiem azotanu(III) sodu a trwałością oksydacyjną kiełbas, zarówno po dojrzewaniu produkcyjnym, jak i po kilkutygodniowym dojrzewaniu poprodukcyjnym. Dodatek liofilizowanego ostropestu, w obu stężeniach, dodatkowo obniżył stężenie wtórnych produktów oksydacji tłuszczu (wskaźnik TBARS) w kiełbasach. Zarówno aktywność wody, jak i wartość pH kiełbas dojrzewających były typowe dla tego typu produktów mięsnych, niezależnie od zastosowanego stężenia dodatku liofilizatu. Dodatek ostropestu nie wpłynął na trwałość barwy, której stabilność zależała wyłącznie od stężenia peklosoli. Stwierdzono, że dodatek roślinny nie ograniczał rozwoju bakterii kwaszących typu mlekowego w produkcie. Po zakończeniu dojrzewania wszystkie warianty charakteryzowały się wysoką liczbą LAB (> 8,2 log jtk/g), przy jednocześnie niskiej liczbie bakterii tlenowych (< 7,1 log jtk/g). Uzyskane wyniki wskazują, że możliwe jest wykorzystanie liofilizowanego ostropestu plamistego jako skutecznego przeciwutleniacza w technologii ekologicznych kiełbas dojrzewających o obniżonym dodatku NaNO2 (< 100 mg/kg)
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Herb plant organs are aboundant in phytochemicals and possess multiple bioactivities. Investigation in the phytochemicals of herb plants organs and associated functionalities essential to explore the potential and deepened the understanding of herb plants. In this study, phytochemicals, antioxidant activity, and α-glucosidase inhibitory activity of leaf, flower, peel, root and seed herb plant organ extracts were investigated. A combination of colorimetric assays and high performance liquid chromatography were applied, and the cellular antioxidant activity was evaluated in the HepG2 model. Results show that leaf and flower organs had the highest total phenolics, flavonoids, flavonols and proanthocyanidins contents. Flower organ possessed the highest 2,2-diphenyl-1-picrylhydrazyl, 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical scavenging activity, cellular antioxidant activity and α-glucosidase inhibitory activity. Leaf organ had the strongest oxygen radical absorbance capacity and glucose consumption. Ferulic acid, salicylic acid, chlorogenic acid and epigallocatechin gallate were the common phytochemical compounds in plant organs. Phytochemical contents showed significant positive correlations (p < 0.05) with antioxidant and hypoglycemic effects. Results revealed that compared with other plant organs in this study, flower organ possessed excellent antioxidant and glucose regulating activities and could provide basis for the development of related health food and products for the diabetes patients.
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The content of phenolic acids in strawberries was determined before and after gamma-irradiation in the dose range 1 to 10 kGy. Fresh whole strawberries were irradiated, acid-base-hydrolyzed, and purified on polyamide columns. The compounds were analyzed by reversed-phase chromatography and detected with a diode-array detector. Dose/concentration relationships were obtained for gallic acid, 4-hydroxybenzoic acid, cinnamic acid, p-coumaric acid, and caffeic acid. Whereas radiolysis of the individual acids in aqueous solutions led to their efficient degradation and to a notable hydroxylation, in the complex matrix of food no hydroxylation products were formed and only the amount of 4-hydroxybenzoic acid was affected by irradiation (build up: 0.68 ± 0.04 mg kg−1kGy−1).
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A rapid and inexpensive HPLC method has been developed for simultaneous separation of the three main classes of polyphenol in the leaves of Cistus salvifolius L. Time devoted to extraction of polyphenols, which was performed using small volume of solvent, did not exceed 120 min. We identified three ellagitannins (punicalagin and related compounds), a total of ten glycosyl derivatives of quercetin and myricetin, and two coumaroyl glucosyl kaempferols by use of both diode-array detection (DAD) and mass spectrometry. The polyphenol composition of C. salvifolius leaves, which may contribute to the metabolic plasticity of the species, may explain its distribution in infertile soils of the Mediterranean area, and may also indicate this shrub is an important source of metabolites of potential use in human health care.
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There is much epidemiological evidence that diets rich in fruit and vegetables can reduce the incidence of non-communicable diseases such as cardiovascular diseases, diabetes, cancer and stroke. These protective effects are attributed, in part, to phenolic secondary metabolites. This review summarizes the chemistry, biosynthesis and occurrence of the compounds involved, namely the C6-C3-C6 flavonoids-anthocyanins, dihydrochalcones, flavan-3-ols, flavanones, flavones, flavonols and isoflavones. It also includes tannins, phenolic acids, hydroxycinnamates and stilbenes and the transformation of plant phenols associated with food processing (for example, production of black tea, roasted coffee and matured wines), these latter often being the major dietary sources. Events that occur following ingestion are discussed, in particular, the deglycosylation, glucuronidation, sulfation and methylation steps that occur at various points during passage through the wall of the small intestine into the circulatory system and subsequent transport to the liver in the portal vein.We also summarise the fate of compounds that are not absorbed in the small intestine, but which pass into the large intestine where they are degraded by the colonic microflora to phenolic acids, which can be absorbed into the circulatory system and subjected to phase II metabolism prior to excretion. Initially, the protective effect of dietary phenolics was thought to be due to their antioxidant properties which resulted in a lowering of the levels of free radicals within the body.However, there is now emerging evidence that themetabolites of dietary phenolics,which appear in the circulatory systemin nmol/L to low mmol/L concentrations, exertmodulatory effects in cells through selective actions on different components of the intracellular signalling cascades vital for cellular functions such as growth, proliferation and apoptosis. In addition, the intracellular concentrations required to affect cell signalling pathways are considerably lower than those required to impact on antioxidant capacity. The mechanisms underlying these processes are discussed.
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Polyphenols are the most abundant antioxidants in the diet and are widespread constituents of fruits, vegetables, cereals, dry legumes, chocolate, and beverages, such as tea, coffee, or wine. Experimental studies on animals or cultured human cell lines support a role of polyphenols in the prevention of cardiovascular diseases, cancers, neurodegenerative diseases, diabetes, or osteoporosis. However, it is very difficult to predict from these results the effects of polyphenol intake on disease prevention in humans. One of the reasons is that these studies have often been conducted at doses or concentrations far beyond those documented in humans. The few clinical studies on biomarkers of oxidative stress, cardiovascular disease risk factors, and tumor or bone resorption biomarkers have often led to contradictory results. Epidemiological studies have repeatedly shown an inverse association between the risk of myocardial infarction and the consumption of tea and wine or the intake level of some particular flavonoids, but no clear associations have been found between cancer risk and polyphenol consumption. More human studies are needed to provide clear evidence of their health protective effects and to better evaluate the risks possibly resulting from too high a polyphenol consumption.
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A simple high-performance liquid chromatography method using a diode array detector (DAD) is developed for the simultaneous analysis of five major catechins: (+)-catechin (C), (-)-epicatechin (EC), (-)-gallocatechin (GCT), (-)-epigallocatechin (EGC), (-)-epigallocatechin gallate (EGCG), and the phenolic plant metabolites gallic acid (GA) and rutin (RT) in lyophilized extracts of Cistus species. The optimal analytical conditions are investigated to obtain the best resolution and the highest UV sensitivity for the quantitative detection of catechins. The optimized conditions (acetonitrile-phosphate buffer 50 mM, pH 2.5, gradient elution system on a C18 reversed-phase column with a flow rate of 1 mL/min and UV absorbance at 210 nm) allowed a specific and repeatable separation of the studied analytes to be achieved. All compounds are successfully separated within 32 min. Calibration curves are linear in the 2-50 microg/mL range for GCT, C, and EGCG and in the 5-50 microg/mL range for GA, EGC, EC, and RT. The limit of detection values ranged from 0.24 to 0.74 microg/mL. The limit of quantitation limit values ranged from 0.77 to 1.94 microg/mL. The validated method is applied to the determination of the specific phytochemical markers GA, GCT, C, and RT in Cistus incanus and Cistus monspeliensis lyophilised extracts. The recovery values ranged between 78.7% and 98.2%. The described HPLC method appears suitable for the differentiation and determination of the most common catechins together with the glycoside rutin and the phenolic compound gallic acid and can be considered an effective and alternative procedure for the analyses of this important class of natural compounds.
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The formation of cream in Paochung tea, a popular semifermented tea, which undergoes a lesser degree of enzymic oxidation during manufacture, was investigated at various extraction temperatures, extraction times, pHs and leaf/water ratios. The primary components of Paochung tea cream were catechins (30%), caffeine (20%) and protein (16%). (-)-Epigallocatechin gallate and (-)-epicatechin gallate were the major catechins precipitated during creaming, constituting 19% and 5% of the tea cream respectively. The amount of tea cream produced and its composition were influenced by extraction temperature and pH. The tea leaf/water ratio determined the amount of tea cream formed but did not affect the cream composition. Catechins were considered to be the key component in tea cream. They interacted with caffeine and protein to induce tea cream formation.
We report on the effect of decaffeination and pH on the kinetics and thermodynamics of tea cream formation using turbidimetry and time-resolved (static and dynamic) light scattering. Decaffeination enhances the solubility of tea solids (polyphenols) in black tea infusions, resulting in a shift of the location of the phase diagram to lower temperatures in comparison to “standard” black tea material. The phase diagrams for the studied tea samples displays similar trends to those of (classical) simple mixtures which dissolve at higher temperatures but separate into immiscible phases below the (upper) critical solution temperature. In the case of decaffeinated tea it did prove possible to access the metastable region of the miscibility gap with nucleation and growth being the important mechanism in the dilute part of the phase diagram. More often than not, however, the mechanism responsible for the formation of tea cream is governed by demixing through spinodal decomposition caused by the increased insolubility of polyphenols. On lowering the pH, the location of the phase diagram is shifted to higher temperatures and larger particles of associated (polyphenol and polyphenol/caffeine) structures are identified, reflecting the decrease in solubility of tea solids in black tea infusions as a result of decreased electrostatic interactions. At natural pH of 4.8 the electrostatic repulsion between the charged droplet surfaces protects the droplets from coagulation, whereas at pH=2.0 close to the iso-electric point coagulation of tea cream particles takes place resulting in a rapid settling out of tea solids, as observed previously by Harbron. Results at pH=3.0 and c=0.3 wt%, however, do not indicate aggregation/coagulation between different particles, which means that under these conditions there is apparently enough electrostatic repulsion preventing cream particles from coagulation.
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Phenolic compounds were extracted from pomegranate (Punica granatum L.) peel, mesocarp and arils. Extracts and juices were characterised by HPLC-DAD-ESI/MS(n). In total, 48 compounds were detected, among which 9 anthocyanins, 2 gallotannins, 22 ellagitannins, 2 gallagyl esters, 4 hydroxybenzoic acids, 7 hydroxycinnamic acids and 1 dihydroflavonol were identified based on their UV spectra and fragmentation patterns in collision-induced dissociation experiments. To the best of our knowledge, cyanidin-pentoside-hexoside, valoneic acid bilactone, brevifolin carboxylic acid, vanillic acid 4-glucoside and dihydrokaempferol-hexoside are reported for the first time in pomegranate fruits. Furthermore, punicalagin and pedunculagin I were isolated by preparative HPLC and used for quantification purposes. The ellagitannins were found to be the predominant phenolics in all samples investigated, among them punicalagin ranging from 11 to 20g per kilogram dry matter of mesocarp and peel as well as 4-565mg/L in the juices. The isolated compounds, extracts and juices were also assessed by the TEAC, FRAP and Folin-Ciocalteu assays revealing high correlation (R(2)=0.9995) of the TEAC and FRAP values, but also with total phenolic contents as determined by the Folin-Ciocalteu assay and by HPLC. Selection of raw materials, i.e. co-extraction of arils and peel, and pressure, respectively, markedly affected the profiles and contents of phenolics in the pomegranate juices, underlining the necessity to optimise these parameters for obtaining products with well-defined functional properties.
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Quantitative estimates of conjugated flavonoid content were obtained by using HPLC to analyze the level of free flavonoids present in acid-hydrolyzed extracts from commercial fruits and vegetables. Cherry tomatoes contained 17−203 μg of quercetin g-1 fresh weight compared to 2.2−11 μg g-1 detected in normal-sized Scottish, Spanish, and Dutch beef tomatoes. The quercetin levels in onions ranged from 185 to 634 μg of quercetin g-1 fresh weight. “Round” lettuce contained 11 μg of quercetin g-1 fresh weight compared to 911 μg g-1 in the outer leaves and 450 mg g-1 in the inner leaves of “Lollo Rosso” lettuce. The conjugated flavonoid content of celery was very variable, ranging from undetectable to 40 μg of luteolin and 191 μg of apigenin g-1 fresh weight. Cooking lowered the quercetin content of both tomatoes and onions with greater reductions being detected following microwaving and boiling than after frying. Keywords: HPLC; quantitative analysis; flavonoids; tomatoes; onions; lettuce; celery; diet
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The formation of a deposit, known in the tea trade as tea ‘cream’, when a black tea infusion ‘creams down’ on cooling is used by professional tea tasters as an indication of strength and briskness in the infusion. This ‘cream’ is essentially a complex of caffeine with theaflavins and thearubigins (polyphenol oxidation products that have been identified in soluble constituents of black tea). The amount and composition of the ‘cream’ formed depends on the composition of the tea and the strength of the infusion. A precipitate containing the same constituents as tea ‘cream’ is formed when 1% by volume of conc, sulphuric acid is added to a tea infusion, and the amount of polyphenolic material in this precipitate—estimated by titration with alkaline permanganate (‘cream index’)—provides a measure of the ability of a tea infusion to cream down. Support has been obtained for the view that ‘briskness’ in a tea infusion, which is negatively correlated with the ‘cream index’, is due to a caffeine theaflavin complex. The colour of the cream, which may vary from orange to brown, is determined by the ratio of thearubigins to theaflavins. A visual assessment of the amount and colour of the cream formed in a tea infusion by a tea taster is therefore in effect a judgment of the amounts and relative proportions of theaflavins, thearubigins and caffeine in the tea, as an indication of the qualities of the tea.
Article
Intensity of astringency and bitterness of seven flavonoid compounds was evaluated by a time-intensity (TI) procedure. Eighteen trained judges rated intensity continuously from ingestion, through expectoration at 10 s until extinction of the sensation. The seven stimuli included two flavan-3-ol monomers, (+)-catechin and (−)-epicatechin, three dimers and two trimers synthesised from catechin or epicatechin by condensation with (+)-dihydroquercitin. As the degree of polymerisation increased, maximum bitterness intensity (Imax) and total duration (Ttot) decreased whereas astringency Imax increased. The monomers were significantly higher in bitterness at Imax than the dimers, which were significantly higher than the trimers. Astringency Imax of the monomers was lower than the dimers or trimers, although no significant difference was found in Ttot among the polymer classes. The bond linking the monomeric units had an influence on both sensory properties. The catechin-catechin dimer linked by a 4→6 bond was more bitter than both catechin-(4→8)-catechin and catechin-(4→8)-epicatechin. Astringency was affected by both the specific linkage and the identity of the monomeric units with the dimer, catechin-(4→8)-catechin, being lower in astringency than either catechin-(4→6)-catechin or catechin-(4→8)-epicatechin. © 1999 Society of Chemical Industry
Article
Caffeine complexation by chlorogenic acid (3-caffeoylquinic acid, CAS Number [327-97-9]) in aqueous solution as well as caffeine–chlorogenate complex in freshly prepared coffee brews have been investigated by high-resolution 1H-NMR. Caffeine and chlorogenic acid self-associations have also been studied and self-association constants have been determined resorting to both classical isodesmic model and a recently introduced method of data analysis able to provide also the critical aggregation concentration (cac). Furthermore, caffeine–chlorogenate association constant was measured. For the caffeine, the average value of the self-association constant determined by isodesmic model (K i = 7.6 ± 0.5 M−1) is in good agreement with the average value (K a = 10 ± 1.8 M−1) determined with the method which permits the determination of the cac (8.43 ± 0.05 mM). Chlorogenic acid shows a slight decreased tendency to aggregation with a lower average value of association constants (K i = 2.8 ± 0.6 M−1; K a = 3.4 ± 0.6 M−1) and a critical concentration equal to 24 ± 1 mM. The value of the association constant of the caffeine–chlorogenate complex (30 ± 4 M−1) is compatible with previous studies and within the typical range of reported association constants for other caffeine–polyphenol complexes. Structural features of the complex have also been investigated, and the complex conformation has been rediscussed. Caffeine chemical shifts comparison (monomeric, complexed, coffee brews) clearly indicates a significant amount of caffeine is complexed in beverage real system, being chlorogenate ions the main complexing agents.
Article
Four monomeric and seven oligomeric flavanoids have been identified from a Cistus incanus subspecies traditionally used for treatment of skin diseases in northern parts of Greece and identified as subsp. tauricus. Flavan-3-ols are (+)-catechin, (+)-gallocatechin, the novel (+)-gallocatechin 3-gallate and the rarely occurring (+)-catechin 3-O-α-β-rhamnoside; proanthocyanidins are procyanidins B1 and B3, gallocatechin-(4α → 8)-gallocatechin, its novel (4α → 6)-regioisomer, gallocatechin-(4α → 8)-catechin, the tentatively identified novel catechin-(4α → 8)-gallocatechin and the trimer gallocatechin-(4α → 8)-gallocatechin-(4α → 8)-catechin. The uncommon flavanone 2R,3R-dihydromyricetin was also obtained.
Article
Black tea infusions of Camellia sinensis leaves were studied for the influence of water composition, especially calcium content, on the amount of extracted organic matter and on the interactions between caffeine and polyphenols. The higher the calcium content, the lower the extraction of caffeine and polyphenols in acidic media. In alkaline media, besides the calcium effect, polyphenols are oxidized. Caffeine NMR chemical shifts varied depending on the water used showing modified interactions. Using model solutions, polyphenols seem to be responsible for these changes in the case of ultra pure water, but in the case of alkaline solutions, the data in model solutions are different from tea infusions implying that other compounds should interact. Moreover, epigallocatechin gallate (EGCg) and epigallocatechin are the polyphenols interacting most strongly with caffeine in infusions and not EGCg and epicatechin gallate as thought before.
Article
Cistaceae is a large family of shrubs widely spread over the Mediterranean area. It includes Helianthemum, Halimium and Cistus genus. Cistus genus contains approximately 20 species distributed in three subgenus. The essential oil of Cistus species has been thoroughly studied, but the polyphenolic composition of the aerial parts of the different Cistus species needs further characterisation. To perform a comparative analysis of the qualitative and quantitative polyphenolic composition of the aerial parts of the most commonly distributed Spanish Cistus species in order to find a relationship between chemotype and subgenus. Thirteen aqueous extracts derived from 10 different Cistus species were analysed by using HPLC with diode array-detection coupled to electrospray ion trap mass spectrometry technique (HPLC-DAD-ESI-MS/MS). Their major compounds were identified and ellagitannins were quantified. Principal component analysis (PCA) was performed on the most relevant compounds to find out the statistical association between chemotype and variety. Three main groups of compounds were found, i.e. ellagitannins, flavonoids and phenolic acids derivatives. The polyphenolic profile was specific for each species, although the abundance of some compounds also varied depending on the soil type. Whereas C. ladanifer, C. salviifolius, C. populifolius and C. libanotis were specially rich in ellagitannins, C. clusii, C. laurifolius and C. monspeliensis contained significant amounts of flavonoids and much less ellagitannins. In contrast, C. crispus, C. incanus and C. albidus showed a polyphenolic profile mostly based on flavonoids. PCA analysis showed a strong relationship between Cistus subgenus and its chemotype based on the most relevant water-soluble polyphenolic compounds. Chemical composition of the leaves' aqueous extracts from plants belonging to the Cistus genus is strongly related to their subgenus, in agreement to previous taxonomical and phylogenetic divisions. In contrast, soil and climate are less influencing factors. Leucocistus and Halimioides subgenus showed a higher content in ellagitannins. However, Cistus subgenus had higher flavonoid content.
Article
The influence of genotype and climatic factors, e.g. mean temperature and mean global radiation level, on the antioxidant activity of kale was investigated. Therefore, eight kale cultivars, hybrid and traditional, old cultivars, were grown in a field experiment and harvested at four different times. In addition to the investigation of the total phenolic content, the overall antioxidant activity was determined by TEAC assay and electron spin resonance spectrometry. A special aim was to characterize the contribution of single flavonoids to the overall antioxidant activity using an HPLC-online TEAC approach. The antioxidant activity and the total phenolic content were influenced by the genotype and the eco-physiological factors. The HPLC-online TEAC results showed that not all flavonol glycosides contribute to the overall antioxidant activity in the same manner. Taking the results of the structural analysis obtained by HPLC-ESI-MS(n) into account, distinct structure-antioxidant relationships have been observed.
Article
Cistus ladanifer is an aromatic shrub that is widespread in the Mediterranean region. The labdanum exudate is used in the fragrance industry and has been characterised. However, there is not enough information about the phenolic content of the raw plant, the aerial part of it being a very rich source of bioactive compounds. Characterisation of the bioactive compounds of the raw plant and its aerial parts. High-performance liquid chromatography with diode array and electrospray ionisation mass spectrometric detection was used to carry out the comprehensive characterisation of a Cistus ladanifer shrub aqueous extract. Two different MS techniques were coupled to HPLC: time-of-flight mass spectrometry and tandem mass spectrometry. Many well-known compounds present in Cistus ladanifer were characterised, such as flavonoids, phenolic acids, ellagitanins, hexahydroxydiphenoyl and derivatives, and other compounds. The method described simultaneously separated a wide range of phenolic compounds and the proposed characterisation of the major compounds of this extract was carried out. It is important to highlight that, to our knowledge, this is the first time that a Cistus ladanifer aqueous extract from the raw plant has been characterised.
Article
Polyphenols are antibacterial and anti-oxidative natural agents. The present in situ study aimed to investigate the effect of different polyphenolic beverages on initial bacterial adherence to enamel in the oral cavity. Initial biofilm formation was performed on bovine enamel specimens mounted buccally on individual upper jaw splints and carried by six subjects. After 1 min of pellicle formation, oral rinses with black tea, green tea, grape juice, Cistus tea or red wine were performed for 10 min. Afterwards the slabs were carried for another 19 or 109 min, respectively. Samples exposed to the oral fluids for 30 and 120 min served as controls. Following intraoral exposure, the slabs were rinsed with saline solution. The amount of adherent bacteria was determined with DAPI-staining (4',6-diamidino-2-phenylindole) and with fluorescence-in situ hybridization (FISH) of eubacteria and streptococci. Rinses with all beverages reduced the amount of detectable bacteria. Lowest number of adherent bacteria was found following rinses with red wine, Cistus tea and black tea as measured with DAPI (up to 66% reduction of adherent bacteria vs. controls). Also FISH revealed significant impact of most tested beverages. Rinses with certain polyphenolic beverages as well as consumption of these foodstuffs may contribute to prevention of biofilm induced diseases in the oral cavity.
Article
Flavonoids are a large family of plant secondary metabolites, principally recognized for their health-promoting properties in human diets. Most flavonoids outperform well-known antioxidants, such as ascorbate (vitamin C) and alpha-tocopherol (vitamin E), in in vitro antioxidant assays because of their strong capacity to donate electrons or hydrogen atoms. However, experimental evidence for an antioxidant function in plants is limited to a few individual flavonoids under very specific experimental and developmental conditions. As we discuss here, although flavonoids have been demonstrated to accumulate with oxidative stress during abiotic and biotic environmental assaults, a convincing spatio-temporal correlation with the flavonoid oxidation products is not yet available. Thereby, the widely accepted antioxidant function of flavonoids in plants is still a matter of debate.
Article
A wide variety of oxygen free radicals and other reactive oxygen species can be formed in the human body and in food systems. Transition metal ions accelerate free-radical damage. Antioxidant defenses, both enzymic and nonenzymic, protect the body against oxidative damage, but they are not 100% efficient, and so free-radical damage must be constantly repaired. Nonenzymatic antioxidants are frequently added to foods to prevent lipid peroxidation. Several lipid antioxidants can exert prooxidant effects toward other molecules under certain circumstances, and so antioxidants for food and therapeutic use must be characterized carefully. Methods of measuring oxidative damage and trapping free radicals in vivo are briefly discussed. Such methods are essential in checking proposals that increased intake of food-derived antioxidants (such as antioxidant vitamins) would be beneficial to humans.
Article
The recent explosion of interest in the bioactivity of the flavonoids of higher plants is due, at least in part, to the potential health benefits of these polyphenolic components of major dietary constituents. This review article discusses the biological properties of the flavonoids and focuses on the relationship between their antioxidant activity, as hydrogen donating free radical scavengers, and their chemical structures. This culminates in a proposed hierarchy of antioxidant activity in the aqueous phase. The cumulative findings concerning structure-antioxidant activity relationships in the lipophilic phase derive from studies on fatty acids, liposomes, and low-density lipoproteins; the factors underlying the influence of the different classes of polyphenols in enhancing their resistance to oxidation are discussed and support the contention that the partition coefficients of the flavonoids as well as their rates of reaction with the relevant radicals define the antioxidant activities in the lipophilic phase.
Article
The genus Cistus includes many typical species of Mediterranean flora; Cistus species are used as antidiarrhetics, as general remedies for treatment of various skin diseases in folk medicine and as anti-inflammatory agents. These species contain flavonoids that are considered to be chain-breaking antioxidants. In this work, we have investigated the effects of crude aqueous extracts from Cistus incanus and Cistus monspeliensis on DNA cleavage and their free-radical scavenging capacity. In addition, their effect on lipid peroxidation in rat liver microsomes was evaluated. These extracts showed a protective effect on DNA cleavage and a dose-dependent free-radical scavenging capacity; Cistus monspeliensis was more active than Cistus incanus; these results were confirmed by a significant inhibition of lipid peroxidation in rat liver microsomes. The experimental evidence, therefore, suggests that because of their antioxidant activity these extracts may offer excellent photoprotection for skin and may be useful in the treatment of human diseases where oxidative stress plays a key role.
Article
The radical cation 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonate), (ABTS*+) was utilized in an on-line HPLC method for the detection of radical scavengers in complex matrixes. The HPLC-separated analytes react postcolumn with the preformed ABTS*+, and the induced bleaching is detected as a negative peak by an absorbance detector at 734 nm. An optimized instrumental and experimental setup is presented. The method is suitable for both isocratic and gradient HPLC runs using mobile phases containing 100% organic solvent or its solution in water, weak acids, or buffers (pH 3-7.4). The method is sensitive, selective, relatively simple, applicable to compounds of different chemical natures; uses common instruments and inexpensive reagents; and has a time-saving, nonlaborious experimental protocol. It can also be used for quantitative analysis. The method was applied to several pure natural antioxidants and plant extracts. The minimum detectable concentration varied from 0.02 to 0.13 microg/mL, depending on the compound tested. The method can be applied to perform kinetic studies, which is illustrated by determination of Trolox equivalent antioxidant capacities (TEAC) of several known antioxidants in flow injection mode.
Article
A microemulsion electrokinetic chromatographic (MEEKC) method was developed for the separation of six catechins, specific marker phytochemicals of Cistus species. The MEEKC method involved the use of sodium dodecyl sulfate (SDS) as surfactant, heptane as organic solvent and butan-1-ol as co-solvent. In order to have a better stability of the studied catechins, the separation was performed under acidic conditions (pH 2.5 phosphate buffer). The effects of SDS concentration and of the amount of organic solvent and co-solvent on the analyte resolution were evaluated. The optimized conditions (heptane 1.36% (w/v), SDS 2.31% (w/v), butan-1-ol 9.72% (w/v) and 50 mM sodium phosphate buffer (pH 2.5) 86.61% (w/v)) allowed a useful and reproducible separation of the studied analytes to be achieved. These conditions provided a different separation profile compared to that obtained under conventional micellar electrokinetic chromatography (MECK) using SDS. The method was validated and applied to the determination of catechin and gallocatechin in lyophilized extracts of Cistus incanus and Cistus monspeliensis.
Article
Pine (Pinus pinaster) bark is a rich source of procyanidin oligomers. From a total polyphenolic extract, we have generated fractions of different procyanidin composition. The mixtures, devoid of gallate esters, were active as free radical scavengers against ABTS(*+), DPPH, and HNTTM. Pine bark fractions were tested for antioxidant activity in solution (hydrogen donation and electron transfer) and emulsion (inhibition of lipid peroxidation) and compared with their galloylated counterparts from grape origin. While galloylation clearly influenced the free radical scavenging efficiency in solution, it did not seem to play a determinant role in protection against lipid peroxidation in emulsion. The fractions were very mild inhibitors of cell proliferation. Because gallate esters appear to interfere with crucial cell functions, gallate free pine procyanidins may be the innocuous chemopreventative agents of choice for many applications in food and skin protection.