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Cornflower (Centaurea cyanus L.) honey quality parameters: Chromatographic fingerprints, chemical biomarkers, antioxidant capacity and others
Abstract
The samples of cornflower (Centaurea cyanus L.) honey from Poland were subjected to ultrasonic solvent extraction applying the mixture of pentane and diethyl ether 1:2v/v (solvent A) as well as dichloromethane (solvent B). The major compounds of the extracts (analysed by GC-MS/GC-FID) were C13 and C9 norisoprenoids. Among them, (E)-3-oxo-retro-α-ionol (2.4-23.9% (solvent A); 3.9-14.4% (solvent B)) and (Z)-3-oxo-retro-α-ionol (3.7-29.9% (solvent A); 8.4-20.4% (solvent B)) were found to be useful as chemical biomarkers of this honey. Other abundant compounds were: methyl syringate (0.0-31.4% (solvent A); 0.0-25.4% (solvent B)) and 3-hydroxy-4-phenylbutan-2-one (1.6-15.8% (solvent A); 5.1-15.1% (solvent B)). HPLC-DAD analysis of the samples revealed lumichrome (4.7-10.0mg/kg), riboflavin (1.9-2.7mg/kg) and phenyllactic acid (112.1-250.5mg/kg) as typical compounds for this honey type. Antioxidant and antiradical properties as well as total phenolic content of the samples were found to be rather moderate by FRAP (ferric reducing antioxidant power), DPPH (1,1-diphenyl-2-picrylhydrazyl radical) and Folin-Ciocalteu assays, respectively. Additionally, CIE L(∗)a(∗)b(∗)C(∗)h chromatic coordinates were evaluated. Colour attributes of cornflower honey were characterised by elevated values of L(∗) and particularly high values of b(∗) and h coordinates, which correspond to medium bright honey with intense yellow colour.
... 9.1% and 14.4%) and phacelia (av. 5.4% and 9.4%) honey [20,21] were also identified in those obtained by DHLLE (7.6%, 9.4% and 1.8%, 2.4%, respectively). 3-Oxo-α-ionol and 3-oxo-α-ionone, typical for cornflower (3.0% and 14.1%, respectively) and eucalyptus honey [20,22] determined in extracts obtained by USE, were also found in DHLLE extracts (4.5%, 1.9% and 2.5%, 14.2%, respectively). ...
... 5.4% and 9.4%) honey [20,21] were also identified in those obtained by DHLLE (7.6%, 9.4% and 1.8%, 2.4%, respectively). 3-Oxo-α-ionol and 3-oxo-α-ionone, typical for cornflower (3.0% and 14.1%, respectively) and eucalyptus honey [20,22] determined in extracts obtained by USE, were also found in DHLLE extracts (4.5%, 1.9% and 2.5%, 14.2%, respectively). Interestingly, the DHLLE method also enabled the detection of 3,4-dihydro-3-oxoedulan (1.4%), which is proposed as a specific marker of cornflower honey and was previously detected as a dominant compound of its headspace by headspace solid-phase microextraction (HS-SPME, up to 45.0%) [23]. ...
... This allows more costefficient and environmentally friendly screenings focused on relevant marker compounds, which are valid for a wide range of honey varieties. As an example, DHLLE allowed the extraction and detection of (E)-3-oxo-retro-α-ionol (7.6%) and (Z)-3-oxo-retro-α-ionol (9.4%), 3,4-dihydro-3-oxoedulan (1.4%), 3-hydroxy-4-phenylbutan-2-one (2.1%), as well as phenyllactic acid (9.4%), from cornflower honey-all compounds have previously been reported as characteristic, and they are typical compounds for this honey type [20,23,28]. Compared to other available methods, this was achieved without the use of expensive consumables such as SPE cartridges or SPME fibers, as well as with up to a 60-fold reduction in the use of dichloromethane. ...
Recently, we proposed a new sample preparation method involving reduced solvent and sample usage, based on dehydration homogeneous liquid–liquid extraction (DHLLE) for the screening of volatiles and semi-volatiles from honey. In the present research, the method was applied to a wide range of honeys (21 different representative unifloral samples) to determine its suitability for detecting characteristic honey compounds from different chemical classes. GC-FID/MS disclosed 130 compounds from different structural and chemical groups. The DHLLE method allowed the extraction and identification of a wide range of previously reported specific and nonspecific marker compounds belonging to different chemical groups (including monoterpenes, norisoprenoids, benzene derivatives, or nitrogen compounds). For example, DHLLE allowed the detection of cornflower honey chemical markers: 3-oxo-retro-α-ionols, 3,4-dihydro-3-oxoedulan, phenyllactic acid; coffee honey markers: theobromine and caffeine; linden honey markers: 4-isopropenylcyclohexa-1,3-diene-1-carboxylic acid and 4-(2-hydroxy-2-propanyl)cyclohexa-1,3-diene-1-carboxylic acid, as well as furan derivatives from buckwheat honey. The obtained results were comparable with the previously reported data on markers of various honey varieties. Considering the application of much lower volumes of very common reagents, DHLLE may provide economical and ecological advantages as an alternative sample preparation method for routine purposes.
... In general, honey consists of sugar, water, and other substances such as proteins (enzymes), phenolic compounds, organic acids, pigments, vitamins, minerals, various volatile compounds, and solid particles (Pereira et al., 2008;Alqarni et al., 2014;da Silva et al., 2016). The different properties of honey are associated with the various compounds derived from honey bees and plant sources, such as enzymes and phenolic compounds (Lachman et al., 2010;Kuś et al., 2014). Some of the properties of honey can confirm the quality and authenticity of honey and find similar characteristics in different types of honey using requirements such as purity, maturity, and deterioration (Silva et al, 2016). ...
... Results of the FRAP assay of IWH showed that Bangka Belitung and Sulawesi honey had a higher yield than honey collected from other regions. The values of the potential antioxidants obtained in the FRAP test positively correlated with the total phenolic and flavonoid contents, thereby indicating that the antioxidant potential was primarily due to phenolic compounds, in this case the flavonoids, which was in accordance with the results of other studies (Lachman et al., 2010;Kuś et al., 2014). Correlation with color demonstrated that the antioxidant activity of dark honey was higher than that of light honey (Socha et al., 2011). ...
Honey is a natural food derived from flowers nectar that has many health benefits. This reason made honey become one of category food product that has a risk to be adulterated because of economically motivation. This study was conducted for characterization and authentication of Indonesia wild honey (IWH) collected from seven geographical regions (Sumatra, Bangka Belitung, Java, Kalimantan, Sulawesi, West Nusa Tenggara, and East Nusa Tenggara) and harvested during 2016–2018 based on physicochemical parameters, sugar content, minerals, and antioxidant components. The study showed that the result differs widely among the type of honey. IWH has a moisture content between 16.52- 33.41%, a pH value between 3.00 to 4.65 and color characteristic ranged from pale yellow to dark brown. All samples contain the highest amount in potassium, but several minerals found in the specific region. Evaluation of authenticity from sugar content data set by principal component analysis (PCA) and Linear Discriminant Analysis (LDA) revealed that the authentic and adulterated honey samples could be differentiated with a 95.5% accuracy. The honey samples were classified on their botanical and geographical origin using the antioxidant properties, and results of PCA and LDA demonstrated that the antioxidant parameters can provide adequate information to allow classification of the various types of IWH samples collected from different geographical regions with accuracy 80-100% for Bangka Belitung, Sulawesi, Kalimantan, West Nusa Tenggara, East Nusa Tenggara and Java island
... Total antioxidant activity was determined spectrophotometrically by the FRAP assay [30]. The method is based on the variation of absorbance which takes place at 593 nm when the ferric complex of TPTZ is reduced to Fe 2+ -TPTZ in presence of antioxidant compounds. ...
... Determination of radical scavenging activity was performed spectrophotometrically, with some modifications, by the DPPH assay [30]. The method is based on the decrease of absorbance at 517 nm of a methanolic solution of the DPPH radical, which takes place when the latter is mixed with an aqueous honey solution. ...
In this work, nonspecific physico-chemical parameters were determined in 160 honey samples belonging to the four main botanical categories present in Sardinia Island, Italy (strawberry tree, thistle, asphodel and eucalyptus) in order to develop a discriminant method for determining the botanical origin of honey. All the possible combinations of the seven physico-chemical parameters (pH, free acidity, electrical conductivity, color, total phenolic compounds, FRAP activity, and DPPH activity) measured in the honey samples were evaluated by Linear Discriminant Analysis (LDA). LDA models led to the prediction of each botanical origin with a very low level of misclassification (typically less than 5%). Since very high levels of correct prediction in cross validation (98.3%) and external validation (100%) were obtained considering only four parameters (i.e. pH, acidity, conductivity and DPPH), these results might allow a fast and easy control of the botanical origin of honeys.
... It is clear that almost all the scientific efforts made in this direction have been successful when devoted towards the quantification of one (or more) molecule rather than the presence/absence of a specific chemical marker. This is the case of methyl syringate, proposed as a marker of asphodel honey [56], but afterwards found in a number of different unifloral honeys [53,[76][77][78][79], even if not in the same concentration levels. The research group of Tuberoso proposed additional chemical markers for the strawberry tree honey [69], Jerković and coworkers found useful chemical markers for unifloral honey by Coffea spp. ...
... Less frequently, in these studies additional characterizations like a chromatographic phenolic profile, a melissopalynological analysis and a mineral composition of major and trace elements are present. In the last ten years, many unifloral honeys from New Zealand [23], Burkina Faso [26], Morocco [102], Italy [48,66,92,93,95,[103][104][105][106][107], India [49,64], Brazil [50], United Arabian Emirates, Oman, Yemen, Pakistan, Australia [64], Japan [65], Croatia [67,79], Poland [76,78], Turkey [108,109], Portugal [110], Romania [111], Slovenia [112], Cuba [113][114][115][116], Greece [117] and Serbia [117] have been evaluated for their antimicrobial, antioxidants and radical scavenging properties evidencing their dependence on the presence of specific phenolic compounds like homogentisic acid, as well as on the botanical and geographical origin [93] and the climatic conditions [64]. Table 2 reports a selection of antioxidant and antiradical properties of the unifloral honeys described in last ten years. ...
Honey is one of the most renowned natural foods. Its composition is extremely variable, depending on its botanical and geographical origins, and the abundant presence of functional compounds has contributed to the increased worldwide interest is this foodstuff. In particular, great attention has been paid by the scientific community towards classes of compounds like phenolic compounds, due to their capability to act as markers of unifloral honey origin. In this contribution the most recent progress in the assessment of new analytical procedures aimed at the definition of the qualitative and quantitative profile of phenolic compounds of honey have been highlighted. A special emphasis has been placed on the innovative aspects concerning the extraction procedures, along with the most recent strategies proposed for the analysis of phenolic compounds. Moreover, the centrality of validation procedures has been claimed and extensively discussed in order to ensure the fitness-for-purpose of the proposed analytical methods. In addition, the exploitation of the phenolic profile as a tool for the classification of the botanical and geographical origin has been described, pointing out the usefulness of chemometrics in the interpretation of data sets originating from the analysis of polyphenols. Finally, recent results in concerning the evaluation of the antioxidant properties of unifloral honeys and the development of new analytical approaches aimed at measuring this parameter have been reviewed.
... The chemical constituents of Peppermint honey revealed that the most common compounds are p-coumaric acid and kaempferol, as well as a high abundance of methyl syringate, vomifoliol, 3,7-dimethylocta-1,5-dien-3,7-diol (terpendiol I) and hotrienol. Furthemore, the major honey headspace compounds were hotrienol, cis-and trans-linalool oxides, linalool and neroloxide [86]. ...
Background: vegetative diversity is based on different climate and geographical origins. In terms of beekeeping, herbal diversity is strongly correlated to the production of a wide variety of honey. Therefore, based on the existing plant diversity in each country, multiple honey varieties are produced with different health characteristics. While beekeeping potential and consumption preferences are reflected in products’ variety, this leads to an increase in the region’s economy and extensive export. In the last years, monofloral honey has gained interest from consumers and especially in the medicinal field due to the presence of phytochemicals which are directly linked to health benefits, wound healing, antioxidant, anticancer and anti-inflammatory activities. Scope and approach: this review aims to highlight the physicochemical properties, mineral profiles and antioxidant activities of selected monofloral honeys based on their botanical and geographical origin. Moreover, this review focuses on the intercorrelation between monofloral honey’s antioxidant compounds and in vitro and in vivo activities, focusing on the apoptosis and cell proliferation inhibition in various cell lines, with a final usage of honey as a potential therapeutic product in the fight towards reducing tumor growth. Key findings and conclusions: multiple studies have demonstrated that monofloral honeys have different physicochemical structures and bioactive compounds. Useful chemical markers to distinguish between monofloral honeys were evidenced, such as: 2-methoxybenzoic acid and trimethoxybenzoic acid are distinctive to Manuka honey while 4-methoxyphenylacetic acid is characteristic to Kanuka honey. Furthermore, resveratrol, epigallocatechin and pinostrobin are markers distinct to Sage honey, whereas carvacrol and thymol are found in Ziziphus honey. Due to their polyphenolic profile, monofloral honeys have significant antioxidant activity, as well as antidiabetic, antimicrobial and anticancer activities. It was demonstrated that Pine honey decreased the MDA and TBARS levels in liver, kidney, heart and brain tissues, whereas Malicia honey reduced the low-density lipoprotein level. Consumption of Clover, Acacia and Gelam honeys reduced the weight and adiposity, as well as trygliceride levels. Furthermore, the antiproliferative effect of chrysin, a natural flavone in Acacia honey, was demonstrated in human (A375) and murine (B16-F1) melanoma cell lines, whereas caffeic acid, a phenolic compound found in Kelulut honey, proves to be significant candidate in the chemoprevention of colon cancer. Based on these features, the use of hiney in the medicinal field (apitherapy), and the widespread usage of natural product consumption, is gaining interest by each year.
... The extracts of edible cornflower parts (petal and honey) and non-edible parts (receptacle and involucre) are rich in compounds with antioxidant, anti-inflammatory and antibacterial properties. These include tocopherols, organic acids, flavonoids and polysaccharides that are used in traditional medicine (Garbacki et al., 1999;Oelschlaegel et al., 2012;Kuś et al., 2014;Escher et al., 2018;Lockowandt et al., 2019). Previous cornflower studies mostly focused on physiological and phytochemical analyses, and few have explored the molecular mechanisms controlling plant traits. ...
Virus-induced gene silencing (VIGS) is a genetic tool used to assess gene function. Tobacco rattle virus (TRV) is a VIGS vector commonly used to induce endogenous gene silencing in plants. However, there is no VIGS system established for Centaurea spp. We evaluated the effectiveness of a TRV-based VIGS system using phytoene desaturase (PDS) as a reporter gene in Centaurea cyanus. Three methods including pressure-, vacuum- and apical meristem-infiltration were tested to infect C. cyanus seedlings. Photobleached leaves were only obtained using apical meristem-infiltration after a 14 d treatment. The CcPDS transcripts in photobleached leaves were significantly reduced compared with that in green leaves treated with empty TRV. Four C. cyanus cultivars were tested to detect their VIGS responses, and ‘Dwarf Tom Pouce Blue’ was the most sensitive. The agro-infiltration condition was optimized by screening for the optimal seedling stage as well as the optimum Agrobacterium density for efficient silencing. Seedlings with four true leaves and infiltration with an Agrobacterium density of OD600 0.5 were optimal conditions to obtain more photobleached leaves and more intense photobleached phenotype. The results demonstrated the feasibility of TRV-based VIGS for functional analysis of genes in C. cyanus.
... Chromatographic fingerprints have been successfully applied to the quality control of herbal drugs. 37,38 As a nontarget evaluation model, HPLC fingerprints have also been used in the authenticity assessment and botanical sources of honeys, 39,40 via the comparison of sample chromatograms with standard fingerprints. ...
Honey fraud has an extensive global magnitude, and impacts both honey price and beekeeper viability. This study aimed to investigate the characteristic phytochemicals of rape, acacia, and linden honey to verify honey authenticity. We discovered methyl syringate, phaseic acid and lindenin (4-(2-hydroxypropan-2-yl) cyclohexa-1,3-diene-1-carboxylic acid) as particular or unique phytochemicals of rape, acacia, and linden honey. Methyl syringate and lindenin were the most abundant component in rape and linden honey; moreover, the average contents reached up to 10.44 and 21.25 mg/kg, respectively. The average content of phaseic acid was 0.63 mg/kg in acacia honey. To our knowledge, the presence of phaseic acid in honey is a novel finding. Furthermore, we established the HPLC fingerprints of three monofloral honeys. We offered assessment criteria and combined characteristic components with standard fingerprints to evaluate the authenticity of commercial rape, acacia, and linden honeys. For uncertain commercial honey samples, genuine pure honeys constituted nearly 70%. We differentiate the adulteration of acacia and linden honeys with low-price rape honey. Our results reveal that 10% of commercial honeys were pure syrups. Overall, we seem to propose a novel and reliable solution to assess the authenticity of monofloral honey.
... Sarı & Ayyıldız (2012) demonstrated that total phenolics of fifty sunflower honey were in between 6.896-23.201mg GAE/100 g. Results for six cornflower honey samples was determined by Kuś et al. (2014) as 260.0 mg GAE/100 g. However, it has been determined that astragalus honey has more total phenolic content and antioxidant activity than sunflower-cornflower honey. ...
In this study, effect of heat treatments (liquefaction at 55 °C for 12 h and pasteurisation at 90 °C 15 sec) on total phenolic content, antioxidant activity and phenolic compounds of astragalus and sunflower-cornflower honeys was investigated. Total phenol content and antioxidant activity of honeys were assessed by Folin-Ciocalteu and ABTS methods, respectively. Phenolic profile was determined by HPLC-DAD system. Only pasteurisation process had a significant impact on sunflower-cornflower honey with regard to total phenolic content and antioxidant activity. Protocatechuic, 4-hydroxybenzoic, caffeic, p-coumaric, and ferulic acids, rutin, kaempferol were detected in astragalus honey, while 2,5-dihydroxybenzoic, chlorogenic, caffeic, p-coumaric, and ferulic acids, apigenin, rutin, kaempferol-3-glucoside, isorhamnetin-3-glucoside, quercetin, luteolin, kaempferol were detected in sunflower-cornflower honey. Pasteurisation significantly decreased caffeic acid in astragalus honey and other detected phenolics showed no significant difference after heat treatments. The impact of liquefaction process is lower than the pasteurisation process in terms of quantitatively phenolic compounds changes.
... Most species of Centaurea are used as folk medicine in Turkey for asthma, chill, antipyretic, antidiaretic, appetitive and menstrual regulator (Baytop, 1984, Tuzlacı and Tolon, 2000, Koçyiğit and Özhatay, 2006. This genus is also a good source for honeybees as the honey plant (Kuś et al., 2014(Kuś et al., , Özler 2018). On the other hand some species are used in landscaping because of large and showy flowers of some members in the genus. ...
In this study, pollen morphology of 5 Centaurea (C. antitauri, C. coronopifolia, C. iberica, C. patula, and C. pterocaula) and 3 Psephellus (P. hypoleucus, P. pulcherrimus, and P. simplicicaulis) species distributed in Turkey have been examined based on the exine structure and sculpturing. Previous papers drew attention to great value of pollen morphology in the taxonomy of Centaurea and divided genus from Centaurea as Rhaponticoides, Psephellus and Cyanus. Pollen grain characters of 8 species were investigated by light microscope (LM). For morphological analysis, pollen grains were prepared according to Wodehouse (1935). Voucher specimens are deposited in the ISTE (Herbarium of Faculty of Pharmacy, Istanbul University). Types of pollen grains are tricolporate, isopolar and tectum complete of all specimens studied. The largest pollen in Psephellus hypoleucus whereas the smallest pollen in Centaurea iberica. The exine sculptures in the rest of the examined specimens are scabrate, microechinate or reticulate. The polar axis (P) ranges from 32.78±1.805 μm to 40.42±1.976 μm in studied Centaurea species and 36.76±0.8109 μm to 40.5±1.3092 μm in studied Psephellus species. The equatorial axis ranges from 30.77±1.43 μm to 39.20±0.632 μm in studied Centaurea species and 37.4878±2.1313 μm to 40.5789±1.7566 μm in studied Psephellus species. All of the morphological parameters investigated are given in detailed. Pollen shape of 8 species, which are we have been studied, is the same shape but their sizes are different. And there are some differences on the exine surface (sculpture). In the taxonomy pollen type gives an idea for these genera and it is also better to combine it with morphological, karyological and molecular data.
... Chromatographic fingerprinting is an efficient and widely used method for determining the content of polyphenols or antioxidant compounds (Zhao, et al., 2016;Sun et al., 2014;Kuś, et al., 2014). Solid-phase extraction techniques have been successfully applied,followed by the identification of the compounds by capillary electrophoresis (CE), gas chromatography, or high-performance liquid chromatography (HPLC).The use ofdiode array detector (DAD) and mass spectrometry (MS) demonstrated greater effectiveness, especially withHPLC in cases of flavonoids and with GC in cases of phenolic acids (Alvarez-Suarez, et al., 2009). ...
Several wild honey samples collected from seven different regions in Indonesia were investigated to determine their total phenolic content, flavonoid content, and free radical scavenging activity by analyzing the 1,1-diphenyl-2-picrylhydrazyl (DDPH) radical and phenolic profile. Rutin, (+)-catechin, ferulic acid, and galangin were found to be the major phenolic compounds of Indonesia wild honey. The total phenolic content significantly correlated with the total flavonoid content (p=0.000) and the percentage of DPPH radical scavenging activity (p=0.000). Results indicated that there are different polyphenol profiles among the different regions.
... Chromatographic fingerprinting is an efficient and widely used method for determining the content of polyphenols or antioxidant compounds (Zhao, et al., 2016;Sun et al., 2014;Kuś, et al., 2014). Solid-phase extraction techniques have been successfully applied,followed by the identification of the compounds by capillary electrophoresis (CE), gas chromatography, or high-performance liquid chromatography (HPLC).The use ofdiode array detector (DAD) and mass spectrometry (MS) demonstrated greater effectiveness, especially withHPLC in cases of flavonoids and with GC in cases of phenolic acids (Alvarez-Suarez, et al., 2009). ...
Several wild honey samples collected from seven different regions in Indonesia were investigated to determine their total phenolic content, flavonoid content, and free radical scavenging activity by analyzing the 1,1-diphenyl-2-picrylhydrazyl (DDPH) radical and phenolic profile. Rutin, (+)-catechin, ferulic acid, and galangin were found to be the major phenolic compounds of Indonesia wild honey. The total phenolic content significantly correlated with the total flavonoid content (p=0.000) and the percentage of DPPH radical scavenging activity (p=0.000). Results indicated that there are different polyphenol profiles among the different regions.
... The antioxidant activity of honey has been revealed in various occasions [46,47,48]. Above and beyond, it was suggested to be a useful marker for determining the variety of honey (i.e., botanical origin of honey) [34]. ...
Testosterone is an anabolic steroid and the principal sex hormone in males. Maintaining adequate levels of
testosterone throughout the life span of male is very desirable, especially it is now well-known that low levels of
testosterone is associated with various aging diseases/disorders. Therefore, still, so many research studies have
focused on enhancing serum levels of testosterone in males. Here, we intended to systematically discuss and
present the impact of honey on serum levels of testosterone in males. This was conducted by searching PubMed,
Scopus, and Embase electronic databases for research articles from May 1993 through April 2019 using the
keywords “honey” and “honeybee” versus “testosterone”. Moreover, references from relevant published articles
were also reviewed and cited to frame an integral discussion, conclusion, and future research needs. In conclusion,
the collective evidence, which is mainly based on in vivo system studies, reveals that oral administration of honey
increases serum testosterone level in males. Mechanistically, honey may increase serum level of testosterone by
increasing the production of luteinizing hormone, enhancing the viability of Leydig cells, reducing oxidative
damage in Leydig cells, enhancing StAR gene expression, and inhibiting aromatase activity in the testes. However,
further research studies on humans, mainly clinical trials, in this specific research approach are still needed to
confirm the effect of honey on testosterone.
... Pure honey DPPH (12.2 ± 0.2 mg Trx 100 g −1 solids) and CUPRAC antioxidant activity (154.7 ± 3.3 μmol Trx 100 g −1 solids) was in a range typical for monofloral honeys, i.e., cornflower (Kuś et al. 2014a) and heather honey from Poland (Kuś et al. 2014b), acacia honey from Marocco (Petretto et al. 2016). As in the case of TPC, varied results related to the effect of heat treatment on AOA of food products were presented in the literature; both the increase and the decrease were noted. ...
The influence of low-temperature spray drying (inlet/outlet air, 75/50 °C) with the use of dehumidified air on rapeseed honey
phenolics, antioxidant activity, and aroma compounds was investigated. Maltodextrin and NUTRIOSE® were used as carriers.
Additionally, skimmed milk was tested as water substitute for feed solution preparation. Honey powders obtained by this method
were characterized by high antioxidant activity and rich aroma. Changes in aroma profile during drying at low temperature were
recognized as favorable and creating desirable fragrance of the product. In the case of 80% honey powders (20% of carrier), the
investigated properties were not deteriorated comparing to pure honey before drying. Thus, this level of carrier addition can be
treated as optimal from the point of view of bioactive properties retention during low-temperature spray drying. Such low carrier
addition was not presented before in case of honey spray drying, and is favorable due to the perception of such product as natural.
If used as food component, the dose of such honey-rich powder can be reduced comparing to traditional products containing
higher amount of carrier (usually not lower than 50%).
... chlorogenic and isochlorogenic acids), apigenine derivates (e.g. apigenine aglicone and apigenin-7-glucoside), coumarin derivates and para-coumaric acid [125][126][127]. Some of these compounds are displayed in Fig. 6 ...
The present study aims to evaluate the inhibitive effect of three synthesized Gemini surfactants and extracts of three plants on the corrosion of carbon steel in formation water using weight loss, potentiodynamic polarization and EIS measurements. All tested materials have served as effective mixed-type corrosion inhibitors. The adsorption behavior of these inhibitors on carbon steel surface was well described via Langmuir adsorption isotherm. The activation parameters for the dissolution of carbon steel in formation water solutions in the absence and presence of these inhibitors were calculated and discussed. The effect of immersion time was studied using weight loss method to evaluate the stability and durability of protective films adsorbed on the carbon steel surface. The morphology of carbon steel surface in inhibited and uninhibited solutions was investigated via SEM, EDX and FT-IR analyses.
... Despite being a simple, fast and low cost procedure, the assay is one of the less reliable methods to assess antioxidant activity, due to the interference of such compounds as carotenoids (Noruma, Kikuchi, & Kawakami, 1997), the steric inaccessibility of some antioxidant substances, and the high possibility of inaccurate interpretations of antioxidant activity, among other important drawbacks . Nevertheless, due to its simplicity, DPPH assay has been the most used method to measure honey's antioxidant activity (Aljadi & Kamaruddin, 2004;Beretta, Granata, Ferrero, Orioli, & Facino, 2005;Escuredo, Míguez, Fernández-González, & Seijo, 2013;Ferreira et al., 2009;Gašić et al., 2014;Isla et al., 2011;Jerković & Marijanovic, 2010;Kuś, Jerković, Tuberoso, Marijanović, & Congiu, 2014;Liu, Ye, Lin, Wang, & Peng, 2013;Noor, Sarfraz, Ali, & Shahid, 2014;Rodríguez-Flores et al., 2015;Saxena, Gautam, & Sharma, 2010;Serem & Bester, 2012;Silici, Sagdic, & Ekici, 2010;Silva, Dos Santos, et al., 2013;Socha, Juszczak, Pietrzyk, & Fortuna, 2009). predicted DPPH by NIR. ...
A thorough updated review of both standardized and the most used and novel analytical methods for the analysis of honey is presented. The methodologies applied to honey in the analysis of the physical parameters (electrical conductivity, rheological properties, specific rotation, color and water activity), the analysis of the properties and the most important components of honey (moisture, sugars, enzymes, HMF, types of acidity and pH, formol index, insoluble solids, organic acids, proteins, amino acids, vitamins, minerals, volatile and semi-volatile compounds and polyphenols), and the antioxidant and antimicrobial activities are described. Finally, the most applied methods for multicomponent analysis and/or for honey authenticity verification (both the botanical and/or geographical origin honey classification and the detection of honey adulteration) are provided.
... chlorogenic and isochlorogenic acids), apigenine (e.g. apigenine aglicone and apigenin-7-glucoside), coumarin and para-coumaric acid [23,24]. Some of these compounds are displayed in Fig. 1. ...
The paper aimed to investigate and evaluate the performance of natural aqueous cornflower (Centaurea cyanus)
extract (CFE) to mitigate carbon steel corrosion in harsh saline formation water. Weight loss measurements,
electrochemical impedance spectroscopy (EIS) and potentiodynamic polarization techniques were all used for
this assessment. The polarization results showed that CFE could act as a mixed-type inhibitor with a reasonable
protection efficiency of ~69% at very low extract addition of 10 ppm. CFE retained its inhibitive effect even at
elevated temperatures where it showed an inhibition efficiency of 63.95% at 313 K. The adsorption behavior of
the main CFE constituents on carbon steel surface was well described following Langmuir adsorption isotherm.
Thermodynamic activation parameters that govern carbon steel corrosion in blank and extract-containing saline
formation water were calculated from the temperature dependence and then discussed. The effect of immersion
time on the weight loss rate indicated that CFE not only keeps its inhibitive activity for carbon steel in saline
water, but also improves its effectiveness over the long term immersion due to synergistic influence of the
corrosion products which offer an additional protection. Structural characterization by using SEM-EDX images
and FT-IR analysis further supported the obtained chemical and electrochemical results.
... 28 Some more examples have been reported: methyl syringate and lumichrome 29 present in manuka honey, considered as biomarkers, are also present in cornflower, thistle, Satureja subspicata Vis., and sage honeys. [30][31][32][33] Therefore, other chemical parameters have been used for helping with the identification of the botanical and/or geographical origins of monofloral honeys: metal ions, carbohydrates, amino acids, or volatile compounds. 9,[34][35][36][37] Beyond the identification of the honey's floral origin, some authors have also reported that phenols may also be useful for determining its geographic origin. ...
The beneficial effects of honey on human health have long been recognized. Today, many of those positive effects have been studied to elucidate its mode of action. This review briefly summarizes the best studied features of honey, highlighting it as an appealing alternative medicine. In these reports, the health benefits of honey range from antioxidant, immunomodulatory, and anti-inflammatory activity to anticancer action, metabolic and cardiovascular benefits, prebiotic properties, human pathogen control, and antiviral activity. These studies also support that the honey’s biological activity is mainly dependent on its floral or geographic origin. In addition, some promising synergies between honey and antibiotics have been found, as well as some antiviral properties that require further investigation. Altogether, these studies show that honey is effectively a nutraceutical foodstuff.
... Eucayptus spp., Hedysarum coronarium L., Salvia officinalis L., and Satureja spp.). It appears that, for honeys that contain lumichrome, the concentration of phenylacetic acid is higher than the normally observed in honey samples [17,19] with one exception-in Dalmatian sage honey, authors have demonstrated the presence of lumichrome, while phenylacetic acid was not found in the tested samples [17]. We have confirmed that lumichrome is present in Polish sweet yellow clover honey (Melilotus officinalis) and that it is accompanied by an enhanced concentration of phenylacetic acid. ...
A case study of Polish Melilotus officinalis honey was presented for the first time. Gas chromatography-mass spectrometry (GC-MS) (after steam distillation, Soxhlet extraction, ultrasonic solvent extraction, and solid phase extraction (SPE)) and targeted high performance liquid chromatography with a photodiode array detector (HPLC-PAD) were applied to determine the characteristic components of honey. While ubiquitous in most honeys, carbohydrates, terpene derivatives, and phenylacetic acid dominated in the Soxhlet extracts (25.54%) and in the application of SPE (13.04%). In addition, lumichrome (1.85%) was found, and may be considered as a marker of this honey. Due to the presence of these compounds, Polish yellow sweet clover honey is similar to French lavender honeys. The major compounds determined in the methanolic extract were (+)-catechine (39.7%) and gallic acid (up to 30%), which can be regarded as specific chemical markers of the botanical origin of melilot honey. With respect to total phenolic and flavonoid contents, 1,1-diphenyl-2-picrylhydrazyl (DPPH) assays were determined spectrophotometrically. The honey exhibited a moderate antioxidant activity, typical for light honeys, which correlates well with its phenolic and flavonoid composition.
... Thus, quality assessment of plant-derived raw materials and end products is an important issue, yet a screening of the literature data reveals that there is still a deficiency of reliable methods for quality consistency evaluation of plant-derived food products. However, in recent years the chromatographic fingerprint in combination with chemometrics has been used as a rational and practical analytical strategy to assess the authenticity, quality consistency and stability of Hawk-tea [19], kiwi and pomelo fruits [20], Korla pear [21], and cornflower honey [22]. With this in mind, the aim of this work was to develop a reliable HPLC procedure for quality consistency evaluation of raw elderberry materials obtained from herbal manufacturers in Poland and used for culinary purposes. ...
Sambucus nigra L. berries have been traditionally used as culinary and medicinal ingredients. To ensure the highest quality of elderberry plant products for consumers, the objective of this study was to develop a HPLC fingerprint procedure for quality consistency evaluation of S. nigra berries obtained from various herbal manufacturers in Poland. The HPLC profiles of thirteen batches of elderberries showed more than sixty peaks in each chromatogram, including fourteen well-resolved common peaks. Four of these were assigned to caffeic acid, syringic acid, myricetin and quercetin. Based on the chromatographic profiles of all the samples, the reference HPLC fingerprint and similarity values were calculated by Matlab 9.1 software. Quantitation of phenolic compounds (flavonols and phenolic acids) revealed that the S. nigra samples with the highest quantity differ to a small extent with regard to the mean content of phenolic compounds. On the other hand, in batches of elderberries with lower similarity values, higher differences in the mean phenolic compound content were observed. The results of hierarchical cluster and principal component analyses showed that samples classified into one group are associated with a similar chemical composition, reflected in fourteen common HPLC peaks and similarity values. Chromatographic fingerprint combined with quantitation of plant bioactive compounds and unsupervised data analysis techniques can be a useful and efficient strategy for monitoring the quality consistency of elderberry fruits.
... MSYR was also detected in manuka honey [16] at higher levels (45 mg/kg). Lower MSYR levels (0.093 to 5.044 mg/kg) were found and dosed in the honeys and honeydews derived from other botanical sources, such as willow [17], cornflower [18], robinia, rape, chestnut, clover, linden blossom, dandelion, sunflower, and fir [19]. Besides leptosin, MSYR was identified as the active compound from manuka honey to which its myeloperoxidase (MPO)-activity inhibition is ascribed [20]. ...
The samples of Satureja subspicata Vis. honey were confirmed to be unifloral by melissopalynological analysis with the characteristic pollen share from 36% to 71%. Bioprospecting of the samples was performed by HPLC-DAD, GC-FID/MS, and UV/VIS. Prephenate derivatives were shown to be dominant by the HPLC-DAD analysis, particularly phenylalanine (167.8 mg/kg) and methyl syringate (MSYR, 114.1 mg/kg), followed by tyrosine and benzoic acid. Higher amounts of MSYR (3-4 times) can be pointed out for distinguishing S. subspicata Vis. honey from other Satureja spp. honey types. GC-FID/MS analysis of ultrasonic solvent extracts of the samples revealed MSYR (46.68%, solvent pentane/Et₂O 1:2 (v/v); 52.98%, solvent CH₂Cl₂) and minor abundance of other volatile prephenate derivatives, as well as higher aliphatic compounds characteristic of the comb environment. Two combined extracts (according to the solvents) of all samples were evaluated for their antioxidant properties by FRAP and DPPH assay; the combined extracts demonstrated higher activity (at lower concentrations) in comparison with the average honey sample. UV/VIS analysis of the samples was applied for determination of CIE Lab colour coordinates, total phenolics (425.38 mg GAE/kg), and antioxidant properties (4.26 mmol Fe(2+)/kg (FRAP assay) and 0.8 mmol TEAC/kg (DDPH assay)).
... In spite of this, gas chromatography is most often chosen for the analysis of volatile and semi-volatile compounds. To investigate the fingerprint of honey from the cornflower Centaurea cyanus L., both of these chromatographic techniques were applied to identify the chemical biomarkers of the honey [68]. Cornflower honey shows higher antibacterial properties than other honeys because of its heightened peroxide activity, which results from its large inhibin concentration [69,70]. ...
Natural products have been used throughout human history for many applications. The matrices of natural products show a myriad of biological activities that can result from a specific compound or from the synergistic effect of several or even hundreds of different components. Moreover, because natural products are derived from living organisms and hence are affected by biotic and abiotic factors during their production, it is extremely difficult to ensure a constant level of activity for these substances among different batches. In order to overcome such obstacles and improve the quality control of these products, which is necessary to obtain reproducible biological activities and approve new commercial uses, the development and application of analytical methods are fundamental. The development of applicable analytical methods along with the qualitative and quantitative characterization of active ingredients and possible interferents need to be extensively studied. However, guidelines or general protocols that can be applied to all samples do not exist, and there is no simple analytical validation method. Every matrix has specific demands and different markers, and quality control laboratories possess different instrumental configurations. Considering these technical difficulties, this review article presents examples, experimental strategies, and arguments demonstrating the importance of qualitative and quantitative knowledge of natural products, analytical validation, and the influence of these matrices over biological results. The major criteria that should be addressed in the development of analytical methods are also discussed. Among several validation parameters, the study of extraction efficiency is highlighted.
Nowadays, phytotherapy is considered by many scientists as the ancestor and the basis of the actual medicine. This old discipline rely in the pharmacological properties of plants to treat various diseases and conditions and supported human beings in all aspect throughout their evolution which allowed several civilizations to develop several remedies, for example to treat wounds, problems related to gastrointestinal transit and even poison. The different plant species that compose Asteraceae family contribute in several sectors, especially in gastronomy, cosmetics and medicine. Indeed, Centaurea is considered an important genus in this family and several phytocompounds contained in Centaurea species are considered nowadays a reference for pharmaceutical industries to develop new drugs with fewer side effects. However, several mechanisms remain ambiguous for scientific community to clearly explain the pharmacological properties of secondary metabolites of plants in order to fully exploit this natural resource. The objective of this book is to summarize and valorize the phytochemical and pharmacological properties of some Centaurea species previously studied.
The "medicinal" benefits of honey have been known for thousands of years, being used as an antiseptic, fortifier, soother, healer, laxative, among others. But in addition to its use as a therapeutic, there is evidence that since ancient Rome honey has been used as a food preservative. Currently, the food industry faces several challenges, among which are maintaining the quality and safety characteristics of their products with the minimum addition of artificial ingredients and additives due to the worldwide increase in demand for natural products and functional properties, as well as helping to reduce food loss and thus its ecological footprint. Currently, honey produced by stingless bees has been the subject of research, due to its nutritional value and its bioactive properties of great utility, both in the pharmaceutical industry and in food production. Therefore, a review of published articles describing the potential uses of the bioactive properties of honey, mainly that produced by stingless bees, in the food industry was carried out.
Honey represents a valuable food commodity, known since ancient times for its delicate taste and health benefits due to its specific compositional characteristics, mainly the phenolic compound content. “Anama” honey is a monofloral honey produced from the nectar of Erica manipuliflora plant, a heather bush of the Greek island of Ikaria, one of the Mediterranean’s longevity regions. “Anama” is characterized by a unique aroma and taste, with a growing demand for consumption and the potential to be included in the list of products with a protected designation of origin. The aim of this study was to determine the chemical and botanical profile of authentic Anama honey samples and find similarities and differences with honey samples of a different botanical origin from the same geographical area. Untargeted Ultrahigh-Performance Liquid Chromatography-Hybrid Quadrupole-Orbitrap High-Resolution Mass Spectrometry (UHPLC-HRMS) metabolomics study was conducted on authentic heather, pine, and thyme honey samples from Ikaria and neighboring islands. The Principal Component Analysis (PCA), Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA), and differential analysis were performed using the entire metabolic profile of the samples and allowed the identification of chemical markers for sample discrimination. Thirty-two characteristic secondary metabolites (cinnamic acids, phenolic acids, flavonoids, terpenes) and other bioactive phenolic compounds, some of them not previously reported in a heather honey (aucubin, catalpol, domesticoside, leonuriside A, picein among others), emerged as potential chemical indicators of Anama honey. Melissopalynological analysis was also carried out to decipher the botanical and geographical origin of Anama honey. The relative frequency of the pollen of dominant plants of the Ericaceae family and a multitude of nectariferous and nectarless plants contributing to the botanical profile of Anama was evaluated. The identification of the pollen sources enabled a potential correlation of differentially increased secondary metabolites and chemicals with their botanical origin. The physicochemical profile of Anama was also determined, including the parameters of pH, color, electrical conductivity, diastase, moisture, as well as sugars, supporting the high quality of this heather honey.
According to legislation, unifloral honeys are characterized by their organoleptic, physicochemical, and microscopic properties. Melissopalynology is the established method for identifying the pollen taken up with the floral nectar by forager bees and is used for authentication of the nectar sources in honey. For cornflower honey (Centaurea cyanus), the pollen input does not correlate with the nectar input, because the nectar is produced both in floral and in extrafloral nectaries. The well-known cornflower marker lumichrome has now also been detected in the extrafloral nectar. Therefore, lumichrome is a suitable marker substance for cornflower honey. Four different methods for the sole analysis of lumichrome in honey were validated and compared. Studies over nine years have shown that unifloral cornflower honey should contain approximately 35 mg/kg lumichrome. For a further differentiated cornflower honey specific verification, other nonvolatile compounds like 7-carboxylumichrome and volatiles, such as 3,4-dihydro-3-oxoedulan I and 3,4-dihydro-3-oxoedulan II, should be analyzed. This enables a more specific accuracy for the classification of unifloral cornflower honey.
Chinese wolfberry is a widely used traditional medicine‐food homology plant with diverse functions. However, as Chinese wolfberry contains abundant monosaccharides, it cannot be consumed by diabetics and obese people, which reduces its health and commercial value. To remove monosaccharide, raw Chinese wolfberry juice was fermented by Komagataeibacter xylinus. Glucose was exhausted after 10 days, and maximum 3.145g/L bacterial cellulose was obtained. The total organic acid and amino acid concentration increased from 2974.32 mg/100 mL and 409.19 mg/100 mL to 4217.7 mg/100 mL and 655.1 mg/100 mL, respectively. Fermentation promoted the generation of esters, volatile acids, aldehydes and ketones, but no observed change in polysaccharide concentration was detected. Fermentation enhanced the contents of flavonoid and polyphenol, and antioxidant ability was also increased.
Non-centrifugal cane sugar (NCS) samples obtained by traditional moulding and granulation, and also via a novel spray-drying powdering process without additives, were assessed to characterise their sugar and phenolic profiles, flavonoid content, as well as colour parameters. As expected, sucrose was the predominant sugar (91.9 – 95.5%), followed by glucose (2.9-4.6%), and fructose (1.6-3.7%). Total phenolic content was between 0.4-0.6% and total flavonoid content into the range of 0.2-0.4%. Six phenolic acids were found in all NCS samples: protocatechuic acid (0.36-0.94 µg/100 g), vanillic acid (0.70-1.45 µg/100 g), chlorogenic acid (2.08-3.82 µg/100 g), syringic acid (1.08-2.80 µg/100 g), p-coumaric acid (0.69-1.35 µg/100 g), and ferulic acid (0.50-0.95 µg/100 g). The thermal treatment under high temperatures required in the production of granulated products was related with darker colours and changes in phenol and flavonoid contents. In contrast, spray drying generates clearer products, but with slightly less phenol and flavonoid contents.
La calidad de la miel es uno de los aspectos que menos se han investigado en Colombia. La revisión bibliográfica de este artículo identificó las características fisicoquímicas de la miel necesarias para establecer su calidad, y se encontró que los parámetros de acidez, pH, hidroximetilfurfural (HMF), cenizas, conductividad eléctrica, azúcares y humedad, entre otros, son los más usados. Para esta revisión se seleccionaron 60 artículos por criterios como procedencia geográfica, publicación reciente y relevancia con el tema de la investigación. Al final del texto, se exponen algunas posibles aplicaciones no tradicionales de la miel que a su vez surgen como nuevos espacios de investigación.
This paper presents the biosynthesis of silver nanoparticles (AgNPs) and gold nanoparticles (AuNPs) from three different plants with numerous pharmacological benefits: Elderflower (Sambucus nigra L.), Acacia (Robinia pseudacacia L.) and Cornflower (Centaurea cyanus) and also describes the chemical synthesis of two phthalocyanine derivatives: tetracarboxamido-zinc phthalocyanine ZnPc(CONH2)4 and octacarboxamido–zinc phthalocyanine ZnPc(CONH2)8, their physical – chemical characterization (e.g.: UV-Vis, FTIR) and the quantum yield of singlet oxygen generation. All the aqueous extracts are characterized by means of qualitative (e.g.: saponins, steroids, terpenoids, antraquinones, cardiac and anthraquinone glycosides, etc.) and quantitative (e.g.: total content of flavonoids, total content of terpenoids, total content of polyphenols, etc.) phytochemical screening using standard analytical methods and the
results clearly show the presence of different bioactive compounds that play a key role in the reduction of metal ions to nanoparticles. Antioxidant activity of both aqueous extracts and metalic nanoparticles is measured and the formation of both metalic nanoparticles is confirmed by optical microscopy (OM) images. The easiest way to observe the formation of AgNPs and AuNPs is the visual change in color of the plant extract solutions which is then confirmed by recording the UV-Vis spectra. Biosynthesized silver and gold nanoparticles are compared to those obtained by classic chemical synthesis. AgNPs and AuNPs further react, for 96 hours and under constant stirring at room temperature, with the two Pcs to obtain complex nanoaggregate materials whose potential formation is analyzed by means of spectroscopic investigations (e.g.: UV-Vis, FTIR, DLS).
Phacelia tanacetifolia Benth. honey (14 samples) collected in Poland was characterized by melissopalynological analysis, color determination (CIE L*a*b*Cab*hab° coordinates) and volatiles (VOCs) composition. VOCs were isolated by headspace solid-phase microextraction (HS-SPME, two fibers) and ultrasound-assisted solvent extraction (USE, two solvents) and analyzed by GC–MS. Principal component analysis (PCA) and hierarchical-tree clustering (HTC) were applied to show trends and form groups and to indicate the most representative unifloral samples. Six samples were pointed out with average pollen 74.9% and color parameters (L = 85.1; a* = − 0.8; b* = 27.9; Cab* = 27.9; hab* = 91.9) that were significantly correlated. High abundance of trans-linalool oxide (27.3–45.9%) that was significantly correlated with the pollen percentages, hexan-1-ol (4.4–5.7%) and lavender lactone (0.8% - 1.5%) were characteristic for their headspace. C13-norisoprenoids, mainly (E)-/(Z)-3-oxo-retro-α-ionol (4.7–5.4%; 6.9–9.4%) and vomifoliol (9.0–13.0%) dominated in their USE extracts.
The edible flowers are widely used, but there is still a lot to be done in relation to its bioactive potential and its correlation with the presence of phenolic compounds. The aim of this study was determined the individual phenolic profile in the hydromethanolic extracts and infusion preparations of four different flower samples (Dahlia mignon, Rosa damascena ‘Alexandria’ and R. gallica ‘Francesa’ draft in R. canina, Calendula officinalis L., and Centaurea cyanus L.) and their bioactive potential (antioxidant, antiproliferative, and antibacterial capacity). All the studied flowers presented different profiles regarding their phenolic composition and revealed biological potential. The bioactive potential of the studied flowers was moderate, the hydromethanolic extracts of rose petals showed the best results for antioxidant and antibacterial assays, while the antiproliferative properties were only present in some of the tested cell lines, for the hydromethanolic extracts, in which dahlia and rose showed the best results. These results demonstrate that edible flowers can be used as a source of phenolic compounds with bioactive potential, which can be applied in the food sector, as foods and as sources natural ingredients.
3-Phenyllactic acid (PLA) is a natural product with broad and effective antimicrobial activity that is often used as a preservative in the food industry and as feed additive to replace antibiotics in livestock feeds. In this study, a two-step biocatalytic process for production of PLA from l-phenylalanine was developed and investigated. In the first step, l-phenylalanine was converted to phenylpyruvic acid (PPA) by recombinant Escherichia coli cells expressing membrane-bound l-amino acid deaminase from Proteus vulgaris. In the second step, unpurified PPA was directly converted to PLA by recombinant E. coli cells co-expressing d-2-hydroxyisocaproate dehydrogenase from Lactobacillus delbrueckii subsp. bulgaricus and formate dehydrogenase from Mycobacterium vaccae N10. Through two-step cascade reactions, 121. mM PLA was produced from 150. mM l-phenylalanine with a yield of 81.3%. Thus, this process showed great production efficiency and is a promising method for industrial production of PLA.
Background: Centaurea cyanus is an endemic and well-known herbal medicine in Iran, is an annual flowering plant in the family of Asteraceae. The flowers are the part used in modern herbal medicine and are considered to have tonic, stimulant and emmenagogue properties, with action similar to that of blessed thistle. The aim this study was to investigate the phytochemical constituents of C. cyanus extract, its antioxidant, anti-tumor and anti-bacterial activities.
Methods: This experimental study was conducted from June to January of 2015 in Islamic Azad University of Varamin, Iran. At first, the phytochemical components of C. cyanus extract was analyzed using gas chromatography–mass spectrometry (GC-MS) method. Subsequently, the antibacterial potential of the extract was evaluated against 4 pathogenic bacteria including Staphylococcus aureus, Streptococcus pyogenes, Psedomonas aeroginosa and Klebsiella pnemoniae via minimum inhibitory concentration (MIC) mathod. Moreover, the anti-oxidant and anti-tumor activities of extract on colon cancer cell line (HT29) were investigate using DPPH and MTT colorimetric methods, respectively. Finally, the Bax and Bcl2 apoptosis gene expression level was analyzed by quantitative Real-time PCR technique.
Results: GC-MS analysis of C. cyanus extract was shown 19 major components and the most frequent component was belonged to n-Hexadecanoic acid (36.4%) and Linoleic acid (19.3%). The maximum antibacterial activity of extract was observed on S. aureus and P. aeroginosa isolates. The antioxidant activity of the extract was 0.109±0.07 mg/ml. Moreover, the MTT results show that extract had IC50= 26.04±0.45 on HT29 cell line. The Real-time PCR results showed the expression level of Bax and Bcl2 was significantly increased and decreased respectively in colon cancer cell line (2.63±0.54 (P< 0.05), 0.38±0.72 (P< 0.05)).
Conclusion: The results of this study show that the extract had significant anti-bacterial and anti-cancer effects and it appear that the extract has potential uses for pharmaceutical industries.
Syringic acid is one of the key skeletal structures of plant-derived chemicals. The derivatives of syringic acid have certain biological functions. In this study, monoclonal antibody to syringic acid-based phytochemicals was prepared and characterized. The obtained antibody reacted with methyl syringate, syringic acid, and leonurine. Methyl syringate is a characteristic compound found in manuka honey, other honey varieties, and plants. Manuka honey was fractionated using HPLC, and reactivity of the fractions with the antibody was examined. The antibody reacted with the fraction in which methyl syringate was eluted. The amount of methyl syringate in honeys as estimated by ELISA using the antibody had a good linearity compared with that estimated by HPLC. These results suggest that the antibody is applicable for the immunochemical detection of syringic acid-derivatives in plants and foods.
Introduction: Nowadays, the treatments of infectious disease are regarded difficult due to increasing antibiotic resistance among pathogenic bacteria, which the reason may be placing of microorganisms in a structure named biofilm. Biofilms are complex structures consisting of surface-attached bacteria. Therefore, it is essential to find new compounds in order to remove and inhibit biofilms. This study aimed to examine the antibacterial activities of alcoholic extracts of Centaurea cyanus on the biofilm structures and planktonic form of six pathogen bacteria(Staphylococcusaureus, Bacilluscereus, Streptococcuspneumoniae, Pseudomonasaeruginosa, Escherichiacoli and Klebsiellapneumonia).
Methods: Antimicrobial activities of the alcoholic plant extracts against the planktonic form of bacteria were assessed via using the disc diffusion method. MIC and MBC values were determined by a macrobroth dilution technique and anti-biofilm effects were scrutinized by microtiter plate method.
Results: The results of this study confirmed high ability of C.cyanus extracts against the biofilm of the tested bacteria as well as their free-living forms. To inhibit bacterial growth, ethanolic extracts proved to be more effective than methanolic extracts. Anti-biofilm effects of plant extracts were associated with the solvent type and extract concentration. C.cyanus extracts were reported to be most efficient to inhibit biofilm formation of E. coli (84/26%) and S. pneumoniae(83/14%). The greatest eradication of biofilm structures were observed on S. pneumonia biofilm (75.66%), and the highest decrease in metabolic activity was reported in S.aureus biofilms (71/85%).
Conclusion: In this study the high capacity of C. cyanus extracts to encounter with whit biofilm was emphasized. Moreover, it was demonstrate
The identification of three light-coloured unifloral honeys was accomplished in this work. Chromatographic fingerprints were obtained through high performance liquid chromatography-electrochemical detection (HPLC-ECD). From the established chromatographic fingerprints, 17 common peaks with relatively high responses were selected as variables for classification. All 40 honey samples (including linden, Vicia villosa Roth and rape honeys) were correctly classified according to their botanical origin using a chemometric method. Additionally, several physicochemical parameters and the content of phenolic acids in the samples were determined. Using physicochemical parameters and phenolic profiles as variables, the overall correct classification rate reached 97.5% and 100%, respectively. The results indicated that the information obtained from the chromatographic ECD fingerprints was useful for the identification of the floral origin of the three light-coloured honeys.
Honey is a very complex matrix to be investigated. Several chemical classes of compounds are present in a very large range of concentration. Large number of research groups worldwide focus their attention and studies to improve the knowledge of honey characterization; it appears clear that new developments of technological improvements would help in putting lights on this complex problem. In the meantime, it is also clear that the officially recognized methodologies are no more sufficient to answer to the more demanding questions concerning honey authenticity. Complicated and time demanding samples preparation, requirement of specialized persons in pollen analysis significantly slow down analysis response, becoming nowadays non more affordable. The emerging new techniques are opening new frontiers in honey characterization and the more promising approach seems to be the multidisciplinary one, focused on the detection of multiple components, with the aid of chemometrics. In the present review the recent findings in the honey characterization by using advanced analytical techniques such as NMR and Raman spectroscopy, mass spectrometry (MS) also coupled with chromatographic techniques, and other methods are presented covering the period between 2010 and 2015.
Phenyllactic acid, a phenolic acid phytochemical with the antimicrobial activity, was rarely reported in food besides honey and sourdough. This study evidenced a new food source of phenyllactic acid and elucidated its metabolic mechanism. Phenyllactic acid naturally occurred in Chinese pickles with concentrations ranged from 0.02 to 0.30mM in 23 pickle samples including homemade and commercial ones. Then, lactic acid bacteria capable of metabolizing phenyllactic acid were screened from each homemade pickle and a promising strain was characterized as Lactobacillus plantarum. Moreover, the investigation of the metabolic mechanism of phenyllactic acid in pickles suggested that the yield of phenyllactic acid was positively related to the content of phenylalanine in food, and the addition of phenylalanine as precursor substance could significantly promote the production of phenyllactic acid. This investigation could provide some insights into the accumulation of phenyllactic acid in pickle for long storage life.
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The major developments and concepts in the study of terpenes (mainly monoterpenes) as well as C9-, C10-, C13-, C14- and C15- norisoprenoids in honey are summarized. Their occurrence and biosynthetic correlations (terpene transformations, particularly the generation of linalool derivatives as well as carotenoid degradation and the corresponding variety of norisoprenoids) are discussed considering the plant/nectar/bee-stomach composition and hive conditions (e.g. warm and acidic conditions that can lead to oxidative degradation of compounds). Terpenes up to C15 have been found as major compounds of the essential oils, but honeys from the same plant sources exhibit only partial similarity to the oil composition (e.g. lavender, sage or citrus essential oils/honeys). The formation of heat-derived or prolonged storage artefacts in honey (mainly the products of Maillard reactions and Strecker degradation reactions) influence the honey composition, and hotrienol is particularly labile among the chemical groups discussed. Stimulated by the challenges of fingerprinting methods and structure identification, exploratory studies (including our published results) on terpenes and norisoprenoids are summarized with emphasis on identifying specific or nonspecific chemical markers of the botanical origin of honey. In general, nonspecific biomarkers dominate in different honey types (e.g. monoterpenes: linalool, linalool oxide isomers or lilac alcohol/aldehyde isomers; norisoprenoids: isophorone and vomifoliol derivatives) while only a few specific biomarkers are found (e.g. anhydrolinalool oxide isomers, 3,4-dihydro-3-oxoedulan isomers, 3-oxo-retro-α-ionol isomers, kamahine A-C or meliracemoic acid).
In the present study, pollen-identical pure manuka and kanuka honeys and an Australian jelly bush honey were analyzed for the non-volatiles by UHPLC-PDA-MS/MS and for the volatiles by HS-SPME-GC/MS. A chromatographic profile matchup by means of characteristic marker compounds achieved a clear discrimination between manuka, kanuka, and jelly bush honey. UHPLC-PDA profiles of manuka honey show leptosin, acetyl-2-hydroxy-4-(2-methoxyphenyl)-4-oxobutanat, 3-hydroxy-1-(2-methoxyphenyl)-penta-1,4-dion, kojic acid, 5-methyl-3-furancarboxylic acid, and two unknown compounds as prominent, kanuka honey was characterized by 4-methoxyphenyllactic acid, methyl syringate, p-anisic acid, and lumichrome. 2-methylbenzofuran, 2'-hydroxyacetophenone, and 2'-methoxyacetophenone were markant volatiles for manuka honey, kanuka honey was characterized by 2,6,6-trimethyl-2-cyclohexene-1,4-dione, phenethyl alcohol, p-anisaldehyde, and an unknown compound in HS-SPME-GC/MS. The jelly bush honey differed from the manuka honey by higher contents of 2-methoxybenzoic acid and an individual unknown substance in the PDA profile and by lower intensities of 2'-methoxyacetophenone and higher concentrations of cis-linalool oxide and 3,4,5-trimethylphenol in the HS-SPME-GC/MS profile.
A new method combining QuEChERS with ultrahigh-performance liquid chromatography and electrospray ionization quadrupole Orbitrap high-resolution mass spectrometry (UHPLC/ESI Q-Orbitrap) was developed for the highly accurate and sensitive screening of 43 antioxidants, preservatives and synthetic sweeteners in dairy products. Response surface methodology was employed to optimize a quick, easy, cheap, effective, rugged, and safe (QuEChERS) sample preparation method for the determination of 42 different analytes in dairy products for the first time. After optimization, the maximum predicted recovery was 99.33% rate for aspartame under the optimized conditions of 10 mL acetionitrile, 1.52 g sodium acetate, 410 mg PSA and 404 mg C18. For the matrices studied, the recovery rates of the other 42 compounds ranged from 89.4% to 108.2%, with coefficient of variation < 6.4%. UHPLC/ESI Q-Orbitrap Mass full scan mode acquired full MS data was used to identify and quantify additives, and data-dependent scan mode obtained fragment ion spectra for confirmation. The mass accuracy typically obtained is routinely better than 1.5 ppm, and only need to calibrate once a week. The 43 compounds behave dynamic range in the 0.001-1000 μg kg−1 concentration, with correlation coefficient > 0.999. The limits of detection for the analytes are in the range 0.0001-3.6 μg kg−1. This method has been successfully applied on screening of antioxidants, preservatives and synthetic sweeteners in commercial dairy product samples, and it is very useful for fast screening of different food additives.
The aim of this study was the obtaining and characterization of two selective vegetal extracts based on polysaccharides and, respectively, polyphenols fraction isolated from Centaurea cyanus L. raw material in order to design one new, natural gastroprotective product. Qualitative studies (HPTLC method) performed on the tinctures and some crude aqueous, ethanol and acetone extracts obtained from Centaurea cyanus raw material (flower head and aerial part) revealed the superiority of crude extracts and, respectively, of acetone solution as concerning polyphenols extraction; have been revealed the occurrence of quercetin, apigenin and caffeic acid derivates, known for the beneficial effect on different type of gastric injuries. More, HPTLC studies made on polysaccharides fractions isolated by the processing of crude aqueous extract revealed elevated levels of polysaccharides and minerals (over 60%, w) aside modest quantities of caffeic and quercetin derivates (less than 1%, w). Differently, polyphenols fraction isolated by the processing of crude acetone extract shown high contents of all gastroprotective compounds (over 10%, w). Accordingly, one final vegetal product based on these two selective extracts, polysaccharides and, respectively, polyphenols fraction, was designed. Further, due to the fact that one of the most important features of a gastroprotective product is the capacity to protect gastric mucous tissue against acidic attack, pharmacological studies made on rats with stress-induced ulcer (this method assure the elevation of gastric acid synthesis) pointed out strong protective effect of this vegetal product based on Centaurea cyanus selective extracts.
Sinorhizobium meliloti bacteria produce a signal molecule that enhances root respiration in alfalfa (Medicago sativa L.) and also triggers a compensatory increase in whole-plant net carbon assimilation. Nuclear magnetic resonance, mass spectrometry,
and ultraviolet–visible absorption identify the enhancer as lumichrome, a common breakdown product of riboflavin. Treating
alfalfa roots with 3 nM lumichrome increased root respiration 21% (P < 0.05) within 48 h. A closely linked increase in net carbon assimilation by the shoot compensated for the enhanced root
respiration. For example, applying 5 nM lumichrome to young alfalfa roots increased plant growth by 8% (P < 0.05) after 12 days. Soaking alfalfa seeds in 5 nM lumichrome before germination increased growth by 18% (P < 0.01) over the same period. In both cases, significant growth enhancement (P < 0.05) was evident only in the shoot. S. meliloti requires exogenous CO2 for growth and may benefit directly from the enhanced root respiration that is triggered by lumichrome. Thus Sinorhizobium–alfalfa associations, which ultimately form symbiotic N2-reducing root nodules, may be favored at an early developmental stage by lumichrome, a previously unrecognized mutualistic
signal. The rapid degradation of riboflavin to lumichrome under many physiological conditions and the prevalence of riboflavin
release by rhizosphere bacteria suggest that events demonstrated here in the S. meliloti–alfalfa association may be widely important across many plant–microbe interactions.
Essential oils obtained by microdistillation from seven endemic Centaurea species [C. hierapolitana Boiss., C. cadmea Boiss., C. calolepis Boiss., C. cariensis Boiss. subsp. maculiceps (O. Schwarz) Wagenitz, C. cariensis Boiss. subsp. microlepis (Boiss.) Wagenitz, C. ensiformis P.H. Davis and C. reuterana Boiss. var. reuterana] and three widespread (C. cyanus L., C. depressa Bieb. and C. urvillei DC. subsp. urvillei) Centaurea L. (Asteraceae) taxa from Turkey were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS) techniques. A total of 158 different compounds were identified. Significant and quantitative differences were observed among the species. Hexadecanoic acid (19.5–33.4%) was the main constituent of C. hierapolitana, C. cadmea, C. calolepis, C. reuterana var. reuterana, C. depressa and C. urvillei subsp. urvillei oils, while carvacrol (13.0–28.4%) was the major compound in, C. cariensis subsp. microlepis, C. cariensis subsp. maculiceps, C. ensiformis and C. cyanus oils.
Free and glycoconjugated volatile composition of three bananas from cultivars of Musa sp. grown in the French West Indies (FWI): Cavendish, Frayssinette and Plantain were investigated. They were extracted from the pulp of bananas thanks to an accelerated solvent extraction method for the free volatile compounds. Glycosides were isolated from aqueous extracts then aglycons were obtained after enzymatic hydrolysis of glycosidic extracts. Free volatile compounds and aglycons were analysed by GC-MS. The main volatile compounds found in Cavendish banana were (E)-2-hexenal and acetoin, in Plantain: (E)-2-hexenal and hexanal, and in Frayssinette: 2,3-butanediol and two diastereomer solerols. The most abundant of aglycons were 3-methyl-butanol, 3-methyl-butanoic acid, solerol (two disatereoisomers) and acetovanillone. This compound, rarely identified in fruits, is detected for the first time in glycoconjugated volatile compounds of fruits. The abundance of these two isomers in the extracts of Frayssinette seemed to be characteristic of this variety of banana. (C) 2011 Elsevier Ltd. All rights reserved.
The HPLC phenolic profiles of 52 selected unifloral honey samples produced in Europe were analysed to detect possible markers for the floral origin of the different honeys. Lime-tree (five markers), chestnut (five markers), rapeseed (one marker), eucalyptus (six markers) and heather (three markers) honeys had specific markers with characteristic UV spectra. In addition, the flavanone hesperetin was confirmed as a marker for citrus honey, as well as kaempferol for rosemary honey and quercetin for sunflower honey. Abscisic acid, which had been reported to be a possible marker for heather honey, was also detected in rapeseed, lime-tree and acacia honeys. Ellagic acid in heather honey and the hydroxycinnamates caffeic, p-coumaric and ferulic acids in chestnut, sunflower, lavender and acacia honeys were also detected. The characteristic propolis-derived flavonoids pinocembrin, pinobanksin and chrysin were present in most samples in variable amounts.© 2001 Society of Chemical Industry
Aroma is an important quality factor in foods. The aroma of bee honey depends on volatile fraction composition, which is influenced by nectar composition and floral origin. Honey of unifloral origin usually commands higher commercial value, thus the floral determination and certification of unifloral honey plays an important role in quality control. This review concerns investigations made on the volatile fraction of bee honey by gas chromatography/mass spectrometry. Recent advances in extraction methods, results achieved, and comparisons of alternative dependable methods for determining floral origin of bee honey are discussed. We emphasize solid phase micro-extraction gas chromatography (SPME/GC) methodology and present some of the results obtained to date, plus the advantages and drawbacks of SPME/GS in comparison with other methods.
Perhaps the single most important event in the history of humankind has been the domestication of the land. The rise and fall of civilizations has hinged on control and success of agricultural production. Feeding the populace has meant adding new land to the area devoted to crop production and technological advances have steered modes of production. Large units of production, fields and farms, worked by large machinery tailored to use of agrochemicals have dominated the development of agriculture in the last 50 years. No human activity has so changed the look of the landscape as has agriculture.
This chapter gives an introduction to the field of carotenoid-derived aroma compounds and illustrates the importance of short-chain carotenoid metabolites as flavor and fragrance substances. Although carotenoid-derived aroma compounds (so-called norterpenoids or norisoprenoids) are ubiquitous constituents in plant derived aromas, very little is known about their biogeneration. Hence, possibilities for an efficient biotechnological production are still limited. After a brief summary of the historical development of norisoprenoid chemistry, this introductory chapter reviews the present knowledge about the occurrence and formation of carotenoid-derived aroma compounds in natural tissues and discusses possibilities for a biotechnological production.
Among the many species of the genus Quercus, only a few are of major technological interest for cooperage. In this work, the main structural and physical-chemical characteristics likely to affect the watertightness of the barrels and the quality of wines stored in oak wood were investigated for three different species in the Erythrobalanus section: American white oak (Quercus alba), sessile oak (Quercus petraea), and pedunculate oak (Quercus robur). Scanning electron microscope images showed that the fact that it is possible to saw-cut American white oak staves, without risking loss of watertightness, is principally due to the special structure of the thyllae in the heart wood of this species. On the other hand, European oak must always be split to avoid rupturing the vessels, as the thyllae of these species do not provide an adequate barrier against liquid seepage. Whereas European pedunculate oak has high quantities of extractable ellagic tannins, sessile oak releases much smaller quantities of polyphenols, and white oak even less. The American species have a greater aromatic potential than European oak due to their high content of cis/trans isomers of β-methyl-γ-octalactone. American white oak is easily identified by the low quantity of extractable polyphenols, the high methyl-octalactone content and the presence of two isomers of 3-oxo-retro-α-ionol. European sessile oak and American white oak are perfectly suitable for aging fine wine. Pedunculate oak, with its low aromatic potential and high ellagitannin content, is best suited to aging spirits. The quantity of extractable methyl-octalactones in American white oak is sometimes excessive and would be likely to have a negative influence on the wine's aroma. Proper control of toasting operations in barrel-making could facilitate the use of this type of oak, by modeling the release of volatile and odorous substances from the wood.
Enantioselective syntheses of two stereoisomers of 3-hydroxy-4-phenyl-2-butanone were investigated via Shi's asymmetric epoxidation or Sharpless asymmetric dihydroxylation of silyl enol ether. (R)-3-Hydroxy-4-phenyl-2-butanone was obtained in 73% enantiomeric excess (ee) by Shi's catalyst/oxone and 80% ee by AD-mix-β, while the (S)-isomer was prepared in 62% ee by AD-mix-α. The characteristic odour of the optically active products was analysed by gas chromatography–olfactometry. The (R)-isomer had a relatively weak fruity and green odour, while the (S)-isomer had a strong caramel, sweet and floral aroma. Additionally, the (S)-isomer presented a stronger odour intensity than did the (R)-isomer. Copyright © 2011 John Wiley & Sons, Ltd.
Habitat management is an important element in sustainable agriculture and can be used to maximize a range of ecosystem services that support crop production. An important example of such ecosystem services is biological control of pests which can be enhanced by providing arthropod natural enemies with suitable floral resources. The potential risk of this approach, however, is that flowering plants may enhance the fitness of the targeted pests as well. We conducted experiments to identify selective plant species that would improve the longevity and parasitization rate of the parasitoid wasp Microplitis mediator without benefiting its host pest, the cabbage moth Mamestra brassicae. Effects on longevity were also assessed for Diadegma fenestrale, a generalist parasitoid wasp attacking Lepidopteran pests. Additionally, we compared the effects of floral and extrafloral nectar, the latter being formed in some plant species and can significantly prolong the duration of nectar availability for natural enemies. Longevity of M. mediator and D. fenestrale as well as parasitization rates of M. mediator was significantly increased by the presence of Fagopyrum esculentum (floral nectar), Centaurea cyanus (floral and extrafloral nectar) and non-flowering Vicia sativa (extrafloral nectar). M. mediator parasitized 202.3±29.7 M. brassicae larvae during its lifetime when presented F. esculentum, compared to 14.4±3.4 larvae in the absence of floral resources. Extrafloral nectar of C. cyanus and V. sativa was as suitable for M. mediator as floral nectar and significantly increased longevity and parasitization rates. Longevity and fecundity of M. brassicae were not supported by the plant species tested. These results stress the importance of plant screening to achieve plant selectivity and to maximize biological control. F. esculentum, C. cyanus and V. sativa are recommended as selective plant species to enhance parasitoids of M. brassicae.
(±)-3-Hydroxy-4-phenyl-2-butanone (1) and (+)-8-hydroxylinalool (2) were isolated from Greek honey samples and their structures were determined by spectroscopic and mass spectrometry methods. The enantiomeric ratio of 1 and 2 was determined using chiral GC–MS. Compound 1 has recently been proposed as a possible chemical marker of thyme honey, but although 1, in our hands, was identified only in monofloral thyme honey amongst the honey samples, it was not found in all studied thyme honey samples and additionally its origin was not directly associated with thyme, proving that compound 1 should not be considered as an unambiguous marker of thyme honey. Compound 2 was isolated and identified as the (+)-6S isomer only in monofloral citrus honey. The combination of (+)-8-hydroxylinalool with methyl anthranilate and caffeine could be proposed as a fingerprint marker for the description of citrus honey. All studied honey extracts and the isolated compounds were also tested for their antimicrobial activity.
Ultrasound-assisted extraction was employed to investigate the composition of extractable compounds from unifloral chestnut and eucalyptus honeys. 1-phenylethanol and 2′-aminoacetophenone are the most powerful botanical markers of chestnut honey. Additionally, cis-cinnamyl alcohol, and p-hydroxyacetophenone were found exclusively in chestnut honey. Organic extractives from whole chestnut flowers were predominated by 1-phenylethanol, nonanal, benzyl alcohol, and nonanoic acid. Of the 16 compounds found in the flower extract, 13 were present in honey as well. Some of them are transferred directly to honey, while in other cases modification reactions take place. Eucalyptus honey is characterized by 2-hydroxy-5-methyl-3-hexanone and 3-hydroxy-5-methyl-3-hexanone, as well as exo-2-hydroxycineole and an unknown norisoprenoid. Aside from, acetoin, nonanal, methyl nonanoate, and dehydrovomifoliol were present in higher concentrations. In eucalyptus flower extracts, norisoprenoids were the most abundant compounds, all of which were also present in the honey samples. 3-Oxo-α-ionone comprised half of the total amount, followed by eucalyptol.
The Pherobase is a freely accessible database of pheromones and semiochemicals. It comprises several databases to provide comprehensive information about pheromones and semiochemicals. Currently, the Pherobase contains pheromones and semiochemicals of more than 7500 species and 6500 semiochemical compounds. The Pherobase lists the occurrence of these semiochemicals within the various animal taxa. Information such as mass spectrometry, kovats retention index, NMR, synthesis, chemical formula, 2D and 3D chemical structures of most of these semiochemicals are given. A kovats retention index database for more than 20000 organic compounds in 35,000 records with literature references are listed. A floral compound database of about 2000 floral compounds and their occurrence in 1700 plant species is also listed. Another database of over 100,000 abstracts related to the Pherobase records is also included, you can browse the references by journal, author, year. A database on the application of semiochemicals in pest management is also included and can be browsed by approach, region, country, host.
Cornflower (Centaurea cyanus) honey can be characterized by a greenish-yellow color and an intensive flavor with a bitter aftertaste. Since cornflower honey contains only a limited amount of pollen for the verification of its floral origin, one objective was the characterization of its polyphenol and norisoprenoid content to assign floral markers. Here, lumichrome (18.8 - 43.5 mg/kg), 7-carboxylumichrome, (Z/E)-3-oxo-retro-α-ionol, and 3-oxo-α-ionol appeared to be quite suitable for distinguishing cornflower honey from other unifloral honeys. Additionally, due to its comparably high hydrogen peroxide content (0.5 - 0.9 mM/h) and the associated antibacterial activity, cornflower honey was used as an alternative treatment of digital dermatitis on an organic dairy farm. Cows affected by this hoof disease often show severe lameness, and a subsequent decline in milk yield and a loss of body condition. The cows' hoofs treated with cornflower honey showed significantly faster healing than the control group without any treatment.
Riboflavin (vitamin B(2)) and its metabolite lumichrome were quantified in 117 samples from 11 unifloral honeys types (Arbutus unedo L., Asphodelus microcarpus Salzm. et Viv., Citrus spp., Eucalyptus spp., Hedysarum coronarium L., Castanea sativa L. honeydew, Mentha spp., Paliurus spina-christi., Salix spp., Salvia officinalis L., Satureja spp.). The quantification of these two compounds was performed by LC-DAD method which does not require sample purification. The proposed method in our study has low limits of detection and quantification, very good linearity in a large concentration range and very good precision. It allows simultaneous determination of 5-hydroxymethylfurfural (HMF) and known chemical biomarkers of unifloral honeys such as abscisic acid diastereomers, homogentisic acid, methyl syringate and kynurenic acid. No statistical correlation was observed between riboflavin and lumichrome content. Although, the concentration of vitamin B(2) in honey may be too low (<6.1mg/kg) to generate interest in the field of nutrition, the presence of its main metabolite lumichrome may be useful to determine the botanical origin of certain unifloral honeys. In fact, the analysis of 11 unifloral honey types showed that Dalmatian sage (S. officinalis L.) honey is characterised by unusual high levels of lumichrome (20.2±2.6mg/kg). The botanical origin of lumichrome from sage flower was assessed by analysing bee-stomach extracts. Other analytical parameters, such as total phenols, antioxidant and antiradical activities, HMF and diastase activity were studied in Dalmatian sage honey.
The volatile components of a Merlot and a Cabernet Sauvignon juice, as well as the volatile compounds released by acid- or glycosidase enzyme hydrolysis of C18 reverse phase isolates of the juices, have been analysed. The categories of constituents (i.e. monoterpenes, benzenoid compounds, norisoprenoids, aliphatic and miscellaneous compounds) and the components observed within these categories were broadly similar to those previously reported for other varieties. The potent flavour compound, damascenone, was a major component of the acid hydrolysates of both juice samples. The damascenone precursor trans-megastigma-6,7-diene-3,5,9-triol was identified as a hydrolysis product of grape-derived C18 reverse phase isolates for the first time.
The character of Merlot wines after the treatments of micro-oxygenation and subsequent chips addition, as regards the colour-related phenolics, volatile composition and sensory characteristics, was studied. An increase in the degree of polymerisation of red pigments and a decrease in the value of the red component of the colour (a*) and the degree of co-pigmentation were observed. The concentrations of monomeric anthocyanins and anthocyanin-derived pigments, such as hydroxyphenyl-pyranoanthocyanins and anthocyanin-ethyl-flavan-3-ol adducts, significantly decreased. With regard to the wine aroma, the micro-oxygenation produced a decrease of some esters, alcohols and benzenic compounds and increased some terpenes and C13-norisoprenoids. With regard to sensorial analysis, micro-oxygenation treatment resulted in higher scores for the red fruit and spicy attributes and caused the presence of new attributes (nutty and sweet fruit). This technique produces a lower level of the typical oak chip aromas (vanilla and woody) in Merlot wines.
In view of the expanding global market, authentication and characterization of botanical and geographic origins of honey has become a more important task than ever. Many studies have been performed with the aim of evaluating the possibilities to characterize honey samples of various origins by using specific chemical marker compounds. These have been identified and quantified for numerous honey samples. This article is aimed at summarizing the studies carried out during the last 2 decades. An attempt is made to find useful chemical markers for unifloral honey, based on the analysis of the compositional data of honey volatile compounds, phenolic acids, flavonoids, carbohydrates, amino acids, and some other constituents. This review demonstrates that currently it is rather difficult to find reliable chemical markers for the discrimination of honey collected from different floral sources because the chemical composition of honey also depends on several other factors, such as geographic origin, collection season, mode of storage, bee species, and even interactions between chemical compounds and enzymes in the honey. Therefore, some publications from the reviewed period have reported different floral markers for honey of the same floral origin. In addition, the results of chemical analyses of honey constituents may also depend on sample preparation and analysis techniques. Consequently, a more reliable characterization of honey requires the determination of more than a single class of compounds, preferably in combination with modern data management of the results, for example, principal component analysis or cluster analysis.
SummaryA miniaturised pressurised liquid technique has been applied to the extraction of volatile compounds present in oak wood samples used in making wine. The solvent extraction performed at high pressure and temperature has allowed the detection of a large number of compounds some of which present sensory and antioxidant properties. The effect of the main process variables on the efficiency of extraction has been studied: the composition of the extracted fraction depended mainly on the polarity of the solvent and the extraction temperature had a high influence on the extracted amount, while the effect of static extraction time and pressure were almost negligible. The highest recoveries were obtained for dichloromethane, for two static 10-min extraction cycles at 60 °C. Among the solvent extraction techniques, miniaturised pressurised liquid extraction presents several advantages, such as the use of reduced amounts of both sample and solvent and high extraction efficiency.
Rare unifloral willow (Salix spp.) honeys obtained from nectar or honeydew were investigated by direct RP-HPLC-DAD method in order to identify and quantify compounds that can be used as possible markers of their origin. Antioxidant and antiradical activities of willow honeys were evaluated using FRAP (=ferric reducing antioxidant assay) and DPPH (=1,1-diphenyl-2-picrylhydrazyl radical) tests, respectively. Also HMF (=5-(hydroxymethyl)furfural), diastase activity, and CIE L*a*b*C*h* chromatic coordinates were evaluated. Abscisic acids (ABA) are typical of willow nectar honey, with a predominance of (Z,E)-ABA on (E,E)-ABA (98.2 and 31.7 mg/kg, resp.). Kinurenic acid and salicylic acid are useful to mark willow honeydew honey. The proposed HPLC-DAD method proved to be easy and reliable to identify the two different Salix spp. honeys, being not affected from any sample preparation artifact. Total antioxidant activity measured with the FRAP assay ranged from 3.2 to 12.6 mmol Fe(2+) /kg, and the antiradical activity measured with the DPPH assay ranged from 0.6 to 3.0 mmol TEAC (=Trolox equivalent antioxidant capacity)/kg in nectar and honeydew honeys, respectively. Salix spp. nectar and honeydew honeys proved to be two completely different honeys, because, besides color attributes, they show different antioxidant properties and specific compounds.
Chemical analysis of Asphodelus microcarpus Salzm. et Viv. honey is of great importance, since melissopalynology does not allow the unambiguous determination of its botanical origin. Therefore, the volatile compounds of eight unifloral asphodel honeys have been investigated for the first time. The honey extracts were obtained by headspace solid-phase microextraction (HS-SPME) and ultrasonicsolvent extraction (USE) and analyzed by GC and GC/MS. In the honey headspace, 31 volatile compounds were identified with high percentages of 2-phenylacetaldehyde (2; 14.8–34.7%), followed by somewhat lower percentages of methyl syringate (1; 10.5–11.5%). Compound 2 is not a specific marker of the botanical origin of the honey, but its high percentage can be emphasized as headspace characteristic of asphodel honey. The extraction solvent for all the samples was selected after extracting a representative sample with pentane, Et(2)O, pentane/Et(2)O 1:2 (v/v), and CH(2)Cl(2) . Compound 1 was the major constituent of all the USE extracts (46.8–87.0%). According to these preliminary results, all the honey samples were extracted by USE with the solvent pentane/Et(2)O 1:2. A total of 60 volatile compounds were identified with 1 as predominant compound (69.4–87.0%), pointing out 1 as Asphodelus honey volatile marker.
HPLC-DAD-MS/MS chromatograms of thistle (Galactites tomentosa Moench) unifloral honeys, previously selected by sensory evaluation and melissopalynological analysis, showed high levels of two compounds. One was characterized as phenyllactic acid, a common acid found in honeys, but the other compound was very unusual for honeys. This compound was extracted from honey with ethyl acetate and purified by SPE using C(18), SiOH, and NH(2) phases. Its structure was elucidated on the basis of extensive 1D and 2D NMR experiments as well as HPLC-MS/MS and Q-TOF analysis, and it was identified as lumichrome (7,8-dimethylalloxazine). Lumichrome is known to be the main product of degradation obtained in acid medium from riboflavin (vitamin B(2)), and this is the first report of the presence of lumichrome in honeys. Analysis of the G. tomentosa raw honey and flowers extracts confirmed the floral origin of this compound. The average amount of lumichrome in thistle honey was 29.4 ± 14.9 mg/kg, while phenyllactic acid was 418.6 ± 168.9 mg/kg. Lumichrome, along with the unusual high level of phenyllactic acid, could be used as a marker for the botanical classification of unifloral thistle (G. tomentosa) honey.
During the liquid chromatographic study of the phenolic fraction of monofloral honeys was detected in the asphodel honey ( Asphodelus microcarpus Salzm. et Viv.) chromatogram a distinctive peak not detected in other monofloral honeys such as Arbutus unedo L., Hedysarum coronarium , Eucalyptus spp., and Galactites tomentosa . After thin layer chromatography (TLC) purification and characterization by NMR and LC-MS/MS, the compound was identified as methyl syringate (MSYR) and confirmed against an original standard. Levels of MSYR were measured in honeys of 2005, 2006, and 2007 by HPLC-DAD analysis. Level determination of MSYR was repeated in 2008 for 2006 and 2007 honeys to evaluate chemical stability of this phenolic compound. Levels of MSYR measured 1 year after the sampling did not show significant statistical differences (p < 0.05). The stability of MSYR was also confirmed by 12 asphodel honey samples collected in 2005 that showed amounts of methyl syringate comparable with those found in fresh honey. For the evaluation of MSYR origin, samples of nectars were collected from flowers and the content of MSYR was measured. Levels of MSYR in honeys are originated from the nectar with an average contribution of the nectar to the honey of 80%. Melissopalinological analysis did not allow the attribution of the honey monofloral origin because levels of asphodel pollen were <6% for all analyzed samples. Previously reported levels of MSYR for robinia, rape, chestnut, clover, linden blossom, dandelion, sunflower, thyme, manuka, and fir honeys were <5 mg/kg. For this reason, a minimum level of 122.6 mg/kg for MSYR in asphodel honeys can be considered as a chemical marker and, unlike the melissopalynological analysis, can be used for the origin attribution and to evaluate the percent of asphodel nectar in the honey.
Geotrichum candidum excretes D-3-phenyllactic acid, which inhibits the growth of Listeria monocytogenes. It was found to inhibit a range of gram-positive bacteria found in humans and foodstuffs, such as Staphylococcus aureus and Enterococcus faecalis, and gram-negative bacteria from humans, such as Providencia stuartii and Klebsiella oxytoca. Scanning electron microscope studies on the effect of D-3-phenyllactic acid on L. monocytogenes showed that it caused changes in bacterial behavior and structure. The bacteria formed aggregates and secreted polysaccharides; their cell walls lost their rigidity, causing the cells to swell. Finally the bacteria broke down completely and the cells disintegrate.
Norisoprenoids appear as promising compounds for authenticating unifloral honeys. So far, however, no method has been optimized for their isolation from a matrix so rich in sugars. In this framework, an original extraction procedure based on the use of Amberlite XAD-16 was developed. Recovery factors were determined and compared with those obtained with another resin (XAD-2). This was done for different model media and various norisoprenoids. In aqueous or alcoholic solutions, the efficiency of both resins proved very high. As expected, addition of honey decreased the adsorption of nonpolar compounds. This effect was much more pronounced with the lower-porosity XAD-2 support. Sugar addition markedly improved the recovery factors obtained with the XAD-16 resin in the case of more polar norisoprenoids.
The stimulatory role of lumichrome, a rhizosphere metabolite, was assessed on the growth of legume and cereal seedlings. At a very low nanomolar concentration (5 nm), lumichrome elicited growth promotion in cowpea, soybean, sorghum, millet and maize, but not in common bean, Bambara groundnut and Sudan grass. In soybean and cowpea only, 5 nm lumichrome caused early initiation of trifoliate leaf development, expansion in unifoliate and trifoliate leaves, increased stem elongation and, as a result, an increase in shoot and plant total biomass relative to control. Lumichrome (5 nm) also increased leaf area in maize and sorghum, and thus raised shoot and total biomass but there was no effect on the leaf area of the other cereals. Root growth was also stimulated in sorghum and millet by the supply of 5 nm lumichrome. By contrast, the application of a higher dose of lumichrome (50 nm) depressed development of unifoliate leaves in soybean, the second trifoliate leaf in cowpea, and shoot biomass in soybean. The 50 nm concentration also consistently decreased root development in cowpea and millet, but had no effect on the other species. These data show that lumichrome is a rhizosphere signal molecule that affects seedling development in both monocots and dicots.
Carotenoids are important precursors of a variety of compounds: the C(20)-retinoids, the C(15)-phytohormones, and the C(9)- to C(13)-aromas. Among the last type, C(13)-carotenoid-derived compounds (norterpenoids/norisoprenoids) such as ionones and damascones, constitute an essential aroma note in tea, grapes, roses, tobacco, and wine. Extraction of carotenoid-derived aroma compounds from plant sources is not economically realistic or considerably expensive. The biotechnological production of aroma compounds represents a feasible alternative and offers the production of enantiomerically pure molecules which can be labeled as "natural." To date, research in the production of ionones or the C(10)-compound, safranal, has mainly been focused on plant dioxygenases that cleave carotenoids in the positions between carbons 9 and 10 (9'-10') or 7 and 8 (7'-8'), respectively. Although relatively little is known about the microbial conversion of carotenoids into compounds with aroma due to the well known advantages of manipulating microorganisms, the aim of this work is to review the current state of the research in microbial production of norisoprenoids and other aroma compounds derived from carotenoid cleavage.
The foliar application of Nod factor [Nod Bj V (C(18:1), MeFuc)] enhanced (P<0.05) the photosynthetic rate of corn; the increases were 36%, 23% and 12% for 10(-6), 10(-8) and 10(-10)M treated plants, respectively. Similarly, lumichrome at 10(-5) and 10(-6)M stimulated the photosynthetic rate of corn plants 1 and 2 days after application. Lumichrome (10(-5) and 10(-6)M) also increased the photosynthetic rates of soybean plants 3 days after treatment. Foliar applications of LCO (10(-6)M) to corn and soybean and of lumichrome (10(-5)M) to soybean increased leaf area, shoot dry mass and total dry mass relative to control plants. However, lumichrome treatments did not affect any growth variable of corn. Results of this study indicate that this signal compound can enhance the photosynthetic rate and growth of plants.
Centaurea solstitialis, commonly known as yellow starthistle, is an invasive plant listed as a noxious weed in the western areas of North America and is the target of classical biological control, which involves release of herbivores known to be specific to this plant. These insects often choose their host plant on the basis of the volatile organic compounds (VOCs) emitted. Accordingly, volatile analysis of host plants can provide insight into VOCs that may attract and/or repel the insect. To this end, solid-phase microextraction (SPME) and a customized collection bag were utilized to perform in situ volatile collection on intact and mechanically damaged leaves of Centaurea solstitialis, Centaurea cyanus, and Centaurea cineraria. Volatile identification was performed by GC-MS, and the VOC differences were determined. The plants C. solstitialis and C. cyanus have been reported to attract the weevil, Ceratapion basicorne, a candidate for biological control, whereas C. cineraria does not attract the weevil. Major VOCs unique to C. cineraria include the sesquiterpenes cyclosativene, alpha-ylangene, and trans-alpha-bergamotene. The compound trans-beta-farnesene was unique to C. solstitialis and C. cyanus.
Fiori e Api, La flora visitata dalle Api e dagli altri Apoidei in Europa
- G R D'albore
- F Intoppa
D'Albore, G. R., & Intoppa, F. (2000). Fiori e Api, La flora visitata dalle Api e dagli altri
Apoidei in Europa. Bologna: Calderini Edagricole [p. 50].
Identification of lumichrome as a Sinorhizobium enhancer of alfalfa root respiration and shoot growth
- D A Phillips
- C M Joseph
- G.-P Yang
- E Martínez-Romero
- J R Sanborn
- H Volpin
Phillips, D. A., Joseph, C. M., Yang, G.-P., Martínez-Romero, E., Sanborn, J. R., &
Volpin, H. (1999). Identification of lumichrome as a Sinorhizobium enhancer of
alfalfa root respiration and shoot growth. Proceedings of the National Academy of
Sciences of the United States of America, 96, 12275-12280.
Blooming and pollen production of several representatives of the genus Centaurea L
- Denisow