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Antioxidative caffeoylquinic acid derivatives in the roots of Burdock (Arctium lappa L.)
Abstract
Five antioxidative caffeoylquinic acid derivatives were isolated from the roots of burdock (Arctium lappa L.), an edible plant in Japan. Their structures were established as 1-O-,5-O-dicaffeoylquinic acid (1), 1-O-,5-O-dicaffeoyl-3-O-succinylquinic acid (2), 1-O-,5-O-dicaffeoyl-4-O-succinylquinic acid (3), 1-O-,5-O-dicaffeoyl-3-O-,4-O-disuccinylquinic acid (4), and 1-O-,3-O-,5-O-tricaffeoyl-4-O-succinylquinic acid (5) on the basis of chemical and spectral (NMR, MS) evidence. The antioxidant activities were measured in a hexane/2-propanol solution of methyl linoleate in the presence of a radical initiator. The antioxidant efficiency increased in the order of α-tocopherol < chlorogenic acid < caffeic acid < (1) = (2) = (3) = (4) < (5).
... Three new sesquiterpenoids (1-3) (Fig. 1) and known compounds were isolated from the extracts of dried A. sieversiana areolas via HP-20 column chromatography and HPLC. The known compounds were identified as costuslactone B (4) [8], artabsinolide A (5) [9], absinthin (6) [10], anabsinthin (7) [11], absinthin A (8) [11], chrysoeriol (9) [12], tricin (10) [13], chrysosplenetin (11) [14], spinacetin 3-O-rutinoside (12) [15,16], epiyangambin (13) [17], de-O-methylepimagnolin A (14) [18], yangambin (15) [19], diayangambin (16) [20], sesamin (17) [21], epiaschantin (18) [22], spinacetin 3-O-β-D-glucopyranoside [15], kaempferol 3-O-β-D-glucopyranoside [23], chlorogenic acid [24], 1,5-dicaffeoylquininic acid [25], and 1,5-dicaffeoylquininic acid methyl ester [25]. The structural determination of new terpenoids and activities of the isolated compounds is discussed herein. ...
... Three new sesquiterpenoids (1-3) (Fig. 1) and known compounds were isolated from the extracts of dried A. sieversiana areolas via HP-20 column chromatography and HPLC. The known compounds were identified as costuslactone B (4) [8], artabsinolide A (5) [9], absinthin (6) [10], anabsinthin (7) [11], absinthin A (8) [11], chrysoeriol (9) [12], tricin (10) [13], chrysosplenetin (11) [14], spinacetin 3-O-rutinoside (12) [15,16], epiyangambin (13) [17], de-O-methylepimagnolin A (14) [18], yangambin (15) [19], diayangambin (16) [20], sesamin (17) [21], epiaschantin (18) [22], spinacetin 3-O-β-D-glucopyranoside [15], kaempferol 3-O-β-D-glucopyranoside [23], chlorogenic acid [24], 1,5-dicaffeoylquininic acid [25], and 1,5-dicaffeoylquininic acid methyl ester [25]. The structural determination of new terpenoids and activities of the isolated compounds is discussed herein. ...
... We also know mixed diesters of caffeic and ferulic acids, i.e., caffeoyl-feruloylquinic acids (CFQAs), which are characteristic of robusta coffee (Coffea canephora, Rubiaceae) or caffeic and sinapic acids, i.e., caffeoylsinapoylquinic acids (CSiQAs), as found in Gardenia jasminoides (Rubiaceae) (Nishizawa et al. 1987), Broccoli sprouts (Moreira-Rodríguez et al. 2017), or Ilex paraguariensis (Jaiswal et al. 2010). Mixed esters involving various combinations of one to three residues of caffeic acid with one or two residues of a dibasic aliphatic acid like glutaric, oxalic, or succinic are also known, especially in the Asteraceae family (Clifford et al. 2008;Maruta et al. 1995). Galloyl conjugates of quinic acids and cinnamoyl conjugates of quinic acid derivatives such as shikimic acid methyl or butyl quinate, and 4-deoxyquinic acid also occur in certain plant species. ...
... Surprisingly, there are rather few reports on CQAs' presence in gymnosperms, including Ginkgo biloba and juniper, and also in berries which are edible and used as spice (Fierascu et al. 2018). Selected examples of plant foods (spices, vegetables, fruits and nuts, beverages) containing CQAs are listed in Table 4, based on Clifford (2017) and some more recent publications (Dillenburg Meinhardt et al. 2019, Jaiswal et al. 2010, Kahle et al. 2005, Maruta et al. 1995, Sytar et al. 2018). Among flowering plants, the monocots seem to be less abundant in CQAs, and their occurrence is rather sporadic. ...
Caffeoylquinic acids (CQAs) are a large family of phenylpropanoids (chemically
esters) found in large amounts in coffee beans but typically occur in many other
edible plants, and as such, they belong to the most widespread polyphenols in
plant kingdom. They are also associated with significant health benefits resulting
from the consumption of beverages such as coffee and yerba maté as well as somepopular vegetables such as globe artichoke or endive. Also, many medicinal herbs
owe their properties to their CQA content. Here, we focused on the importance of
these compounds for functional properties of healthy foodstuff, summarizing
such well-studied aspects as bioavailability, in vitro and in vivo pharmacological
effects, and potential for lifestyle disease prevention and management. The
chemical diversity and analytical approaches are also outlined.
From the literature review, it is concluded that CQAs count as the most
essential healthy constituents of various foods and beverages and should be
included in characterization of edible consumer products. At the same time, one
should remember that caution is necessary in claiming unfounded properties to
cure diseases. Therefore, more research is necessary, especially on human subjects,
as well as further development of affordable and reliable analytical methods
in an ultimate goal to understand their distribution, diversity, and function.
... Organic acids, including citric, malic, fumaric, succinic, chlorogenic, caffeic, quinic, pyroglutamic, and gluconic are widely distributed throughout the plant and can rapidly regulate cellular metabolism (Maruta et al. 1995;Ping and Rong 2006). In the present study, the concentration of citric, succinic, fumaric, and malic acid (TCA cycle intermediates) varied in the coffee trees, depending on the [CO 2 ] treatment. ...
... At the pinhead and fruit expansion phases, low concentrations of chlorogenic acid were detected in the leaves, and a gradual increase in the concentration of this acid was detected during the fruit ripening and senescence phases, which was especially apparent in plants grown under ambient [CO 2 ]. Chlorogenic acids are abundant in coffee trees and are known to possess antioxidant and antibiotic activities and play a role in numerous biological functions, including pest and disease resistance (Maruta et al. 1995;Matsuda et al. 2003). However, most of the available information about these compounds in coffee trees are related to the beans and not the plants themselves. ...
Increasing atmospheric CO2 concentrations ([CO2]) are unequivocal, widespread, and responsible for increased mean global temperatures and altered precipitation patterns. In this context, among the topics that need to be better understood are the changes in the water-related processes and gas exchange properties of plants grown under these conditions. Notably, the effects of climate change on coffee (Coffea spp.) production are particularly concerning given the importance of this commodity. Especially, it has been reported that coffee trees exhibit better photosynthetic efficiency when grown at higher [CO2] levels. In order to elucidate the mechanisms involved with this response, the seasonality of water-related processes, gas exchange, and carbohydrate metabolism were investigated using C. arabica var. Red Catuaí grown at ambient and high [CO2] under field conditions, at a free-air CO2 enrichment (FACE) facility for coffee, in Brazil. The trees were evaluated fortnightly, from November to February (hot and rainy—summer) and from June to September (cold and dry—winter). It was found that C. arabica trees grown under high [CO2] conditions exhibited increased photosynthetic rates (averaging 121% higher in summer and 45% higher in winter) in both seasons, without displaying any significant changes in the seasonal photosynthesis pattern. Additionally, there was a tendency for the coffee trees grown at high [CO2] to exhibit increased levels of soluble carbohydrates, organic acids, and amino acids in the leaves. Our findings suggest that coffee trees adapt to increased [CO2] through increased photosynthetic rates, enhanced stomatal conductance regulation, and augmented carbohydrate and organic acid synthesis. It is plausible that these features could help mitigate the effects caused by climate change.
... Caffeoylquinic acids are the major bioactive phenolic compounds of Arctium species and impart superior antioxidant properties to the plant. The roots of A. lappa were reported to contain caffeoylquinic acid derivatives such as 1-0-,5-O-dicaffeoylquinic acid, 1-0-,5-O-dicaffeoyl-3-Osuccinylquinic acid, 1-0,-5-O-dicaffeoyl-4-O-succinylquinic acid, 1-0-,5-O-dicaffeoyl-3-O-,4-O-disuccinylquic acid and 1-0-,3-0-,5-O-tricaffeoyl-4-O-succinylquinic acid (Maruta et al., 1995). Chlorogenic acid content is much higher than the caffeic acid and both occur mainly in the skin of A. lappa roots (Chen et al., 2004). ...
... It is believed that lignans and caffeoylquinic acids from A. lappa are of value because of their antioxidant capacity (Maruta et al., 1995;Mkrtchian et al., 1998;Jaiswal and Kuhnert, 2011) by which they can scavenge free radicals that are thought to play an important role in many diseases. ...
Arctium species are known for a variety of pharmacological effects due to their diverse volatile and non-volatile secondary metabolites. Representatives of Arctium species contain non-volatile compounds including lignans, fatty acids, acetylenic compounds, phytosterols, polysaccharides, caffeoylquinic acid derivatives, flavonoids, terpenes/terpenoids and volatile compounds such as hydrocarbons, aldehydes, methoxypyrazines, carboxylic and fatty acids, monoterpenes and sesquiterpenes. Arctium species also possess bioactive properties such as anti-cancer, anti-diabetic, anti-oxidant, hepatoprotective, gastroprotective, antibacterial, antiviral, antimicrobial, anti-allergic, and anti-inflammatory effects. This review aims to provide a complete overview of the chemistry and biological activities of the secondary metabolites found in therapeutically used Arctium species. Summary of pharmacopeias and monographs contents indicating the relevant phytochemicals and therapeutic effects are also discussed, along with possible safety considerations.
... Burdock (Arctium lappa L.) belongs to the genus of Arctium in the family Asteraceae. It has long been cultivated in Eastern Asian countries, particularly in China, Japan, and Korea (1). It has been used as a root vegetable or a traditional medicinal plant for centuries and remains popular today. ...
... Many studies also suggest that burdock roots possess antioxidative, anti-inflammatory, and anti-cancer activities (8)(9)(10). These biological activities are attributed to the presence of polyphenols as well as dietary fiber such as inulin and lignan in burdock roots (1,3). ...
The major trend in the antioxidant market is the growing consumer demand for natural antioxidants. Tea, one of the most widely consumed beverages in the world, is an easy way to obtain antioxidant components from a natural source. Our objective was to develop burdock root tea (BRT) with potent antioxidant activity and good color quality. In order to obtain maximum antioxidant activity and quality, the effect of roasting was determined. The antioxidant capacities and total phenolic contents of BRT increased as roasting increased. The color of BRT became darker with increased roasting, extraction time, and amount of burdock roots. Color of BRT was also positively correlated with total antioxidant capacity. Roasting significantly enhanced the total antioxidant activities and color quality of BRT. These results suggest that roasting BRT increases beneficial antioxidant components from burdock roots.
... It is widely used in popular medicine all over the world for its well-known therapeutic applications. It has anti-bacterial, antifungal (12), diuretic (13), anti-oxidant (14) anxiolytic (15), anti-platelet aggregating (16) and HIV-inhibitory properties (17). Bacterial resistant to antibiotics is increasing, requiring introduction of new and safe antibacterial substances. ...
Introduction: Arctium lappa (Great burduck) and Artemesia absinthium are medicinal plants that
some of their antibacterial and antivirus properties have been suggested in nutritional industries.
The objective of this research was to study the effects of A. lappa and A. absinthium on some
microorganisms including Pseudomonads aeraginosa, Haemophilus influenza, Bacillus subtilis,
Bacillus cereus, Klebsiella pneumonia and Staphylococcus aureus.
Methods: Extracts were prepared by maceration method and tested on Mueller Hinton agar medium
based on disc diffusion method. The minimum inhibitory concentration (MIC) and minimum
bactericidal concentration (MBC) were determined by micro-dilution method. Antibiotic disks used
for controlling and standardizing the examination.
Results: The extracts of A. lappa and A. absinthium had significant effect on S. aureus. The MIC and
MBC concentrations of the extract of A. lappa on B. subtilis were respectively 600 and 750 mg/ml.
Also, these values were 230 and 540 mg/ml for H. influenza. Extract of A. absinthium showed more
inhibitory effect on B. subtilis. All extracts showed inhibitory effect on B. cereus. The extracts of A.
lappa and A. absinthium had inhibitory effects on H. influenza and P. aeraginosa. Among antibiotics,
only Ofloxacin and Ciprofloxacin had effects on H. influenza. Extract of A. lappa showed flimsy effect
on K. pneumonia, while extract of A. absinthium had no effect on this bacterium.
Conclusion: Due to the effects of A. lappa and A. absinthium on some bacteria, they might be good
substitutes for synthetic substances.
... Onopordopicrin 7 (PubChem CID: 6440861) is a sesquiterpene lactone isolated from A. lappa leaves, and it was found to exert antioxidant activity via activation of the Nrf2/HO-1 signaling pathway in a primary human muscle cell model exposed to H 2 O 2 oxidative stress [88]. Maruta [89]. The antioxidant effects of A. lappa extract and its bioactive metabolites are illustrated in Table 1. ...
Arctium lappa L. is a medicinal edible homologous plant, commonly known as burdock or bardana, which belongs to the Asteraceae family. It is widely distributed throughout Northern Asia, Europe, and North America and has been utilized for hundreds of years. The roots, fruits, seeds, and leaves of A. lappa have been extensively used in traditional Chinese Medicine (TCM). A. lappa has attracted a great deal of attention due to its possession of highly recognized bioactive metabolites with significant therapeutic potential. Numerous pharmacological effects have been demonstrated in vitro and in vivo by A. lappa and its bioactive metabolites, including antimicrobial, anti-obesity, antioxidant, anticancer, anti-inflammatory, anti-diabetic, anti-allergic, antiviral, gastroprotective, hepatoprotective, and neuroprotective activities. Additionally, A. lappa has demonstrated considerable clinical efficacies and valuable applications in nanomedicine. Collectively, this review covers the properties of A. lappa and its bioactive metabolites, ethnopharmacology aspects, pharmacological effects, clinical trials, and applications in the field of nanomedicine. Hence, a significant attention should be paid to clinical trials and industrial applications of this plant with particular emphasis, on drug discovery and nanotechnology.
... The plant is also a rich source of lignans, sesquiterpene lactones, polyynes, sulfur derivatives, caffeic acid derivatives, polysaccharides, mucilage's, triterpenes, phytosterols and their esters, tannins, and lignans. Burdock leaves, fruits, and seeds have been found to contain various important principles like arctigenin, arctiin, trachelogenin, lappaol F, diarctigenin, terpenoids, polyphenols, beta-eudesmol, caffeic and chlorogenic acid, tannins, inulin and sterols, amino acids, metal elements, vitamins, particularly vitamin C, A, B1, and B2), crude fiber, phosphorus, carotene, sulfur-containing acetylenic compounds (Angerhofer 2002;Chan et al. 2011;Fleming 2000;Jeelani and Khuroo 2012;Kato and Watanabe 1993;Kemper 2010;Maruta et al. 1995;Matsumoto et al. 2006;Park et al. 2007;Schulte 1967;Wang and Yang 1993;Washino et al. 1986. The plant also contains a good amount of total phenolic content (Predes et al. 2011). ...
Gurez is situated along the Kishanganga river in Kashmir valley. It is remotely located but the most beautiful valley. Owing to connectivity problems, this valley has largely remained unexplored and thereby its various features have generally gone unnoticed. This beautiful valley harbors a diversity of the medicinal plants. These medicinal plants are not only used in traditional health care system for the treatment of various diseases but also provide an edge for socio-economic upliftment for households. The socio-economic profile of the people of this remote area depicts that these people live in underprivileged conditions. The medicinal plants indigenous to Gurez, like Bunium persicum, Achillea Millefolium, and Carum carvi besides others, have high commercial value and can be utilized as a source of income. These phytochemically rich plant species can contribute to the development of various formulations of herbal therapies. However, overexploitation of these plant species has caused a decline in the frequency of these species in the past few years. Planned cultivation, proper exploitation, and the commercialization of these medicinal plants can serve as a primary source of income to the people of this downtrodden community of Gurez, particularly marginalized farmers and landless poor people. These plants have the potential to broaden livelihood opportunities of these people by framing proper policy that can give topmost priority to proper exploration of these plants.
... It is regarded for its healing effects. In traditional medicine, the roots of Articum lappa were found to be antioxidant and antibacterial (Holetz et al., 2002;Maruta et al., 1995). ...
Intracanal medicaments are recommended to supplement chemomechanical preparation to enhance disinfection. Calcium hydroxide is the most widely used intracanal medicament for this purpose. However, innovation in material sciences has led to exponential growth in the field of endodontics. Many of these newly developed formulations, including specific new synthetic and herbal medicaments, have shown promising results. Few of them have already been commercialized. However, for the majority of them to be commercialized and used on a regular basis, large sample clinical trials with extended follow-up are required.
Furthermore, the exact dose, treatment time, form of dispensation, and ideal vehicle for delivery are yet to be experimented and patented. On the other hand, currently, there are highly developed medicaments available that are being widely used and serve the purpose well. This chapter highlights the conventional, new, and developing intracanal medicaments and their methods of placement and removal.
... In our previous chemical constituent study of M. chamomilla, except chlorogenic acid, five other caffeoylquinic acids (neochlorogenic acid, cryptochlorogenic acid, and isochlorogenic acid A, B, and C) were identified from M. chamomilla for the first time ( Figure 1). e CAs represent a class of interesting natural products with wide pharmacological activities including antioxidant [14], anti-inflammatory [15,16], antimicrobial [17], enzyme inhibition [18], hepatocyte protection [19], platelet aggregation inhibition [20], antihepatic fibrosis [21], and anti-SARS [22]. According to these previous reports, the pharmacological activities of CAs were consistent with the efficacy of CMC and WHMC, and thus, the CAs should be the active ingredients. ...
A simple and effective method for the simultaneous quantitative analysis of six caffeoylquinic acids (CAs) in Matricaria chamomilla L. (M. chamomilla) using high-performance liquid chromatography (HPLC) with diode-array detection (DAD) was established. The chromatographic separation was performed on a Waters XBridge Shield RP C18 column (4.6 mm × 250 mm, 5 μm) with the mobile phase of acetonitrile (0.5% phosphoric acid) and water (0.5% phosphoric acid) using a gradient elution at a flow rate of 1.0 mL/min and UV detection at 327 nm. The correlation coefficients of all analytes were 0.999, and the results showed excellent linearity. The lower limits of detection (LLOD) and quantification (LLOQ) of all analytes fall within the range of 0.014∼0.017 μg/mL and 0.068∼0.086 μg/mL, respectively. The extraction recoveries of all analytes fall within the range of 100.74%∼101.55%, with relative standard deviation not exceeding 2.83%. The intraday and interday precisions fall within the range of 0.03%∼0.65% and 0.02%∼0.09%, respectively. This validated method was successfully applied to the investigation of 34 samples of M. chamomilla collected from different geographical areas. The results showed that the established method is appropriate for the analysis of the six CAs in M. chamomilla and helpful for quality assessment of capitula of M. chamomilla (CMC), whole herb of M. chamomilla (WHMC), and related herbal formulas.
... Although radical scavenging plays an important role in disease prevention by phenolics, this is not their only mechanism of action. The main phenolic compounds of the Burdock roots are caffeoylquinic acid derivatives (Ferracane, Graziani, Gallo, Fogliano, & Ritieni, 2010;Jaiswal & Kuhnert, 2011;Lin & Harnly, 2008;Maruta, Kawabata, & Niki, 1995;Wang et al., 2019). Chlorogenic acid known as 5-O-caffeoylquinic acid (5-CQA) as per guidelines of IUPAC (1976) and caffeic acid are also the main phenolic compounds present in Burdock roots though the former is present in greater quantity (Jaiswal & Kuhnert, 2011). ...
The current study aimed to evaluate how the harvest time affects the phenolic composition in Burdock root flours (BRF) and how these phenolics are influenced by the gastro-intestinal digestive environment. Burdock roots were harvested in 2020 in Jiangsu Province in June (B1), July (B2) and August (B3). The main phenolic, 5-O-caffeoylquinic acid (5-CQA) decreased after in vitro digestion from 1.14 to 0.22 mg/g (B1 < B2 < B3). Total phenolic content of BRF was 61 % lower after in vitro digestion whereas 5-CQA bioaccessibility remained at about 60 %. Twelve other phenolic compounds were tentatively identified after in vitro digestion. An average reduction in antioxidant capacity of 27% and 10% was observed for DPPH and ABTS, respectively. In conclusion, data demonstrated that phenolic composition, bioaccessibility and antioxidant capacity of Burdock roots harvested at different times were subject to the influence of in vitro gastrointestinal digestion.
... Due to the antioxidant properties of these compounds, there is a growing interest in using them for disease prevention (Elijah et al., 2014). We found higher TPCs and TFCs in whole BF sprouts (83.37 GAE mg/g and 46.21 QE mg/g) than in BRs (22.33 GAE mg/g and 2.06 QE mg/g) ( Another study suggested that the free radical scavenging activity of Arctium lappa could be attributed to caffeoylquinic acid derivatives (Maruta, Kawabata, & Niki, 1995). Arctium lappa, commonly known as burdock, is used for its root and has long been cultivated for food and folk medicine, similar to BFs (Predes, Ruiz, Carvalho, Foglio, & Dolder, 2011). ...
The balloon flower (BF) is a potent natural source of phytochemical compounds and is associated with our health. The sprouting process is accompanied by significant changes in phytochemical compounds in comparison with their original plants. Even though many studies are conducted with BF, there are not yet reports of BF sprouts. In the present study, we determined the chemical composition and biological activity of BF sprouts that had been cultivated for 50 days. Kaempferol‐3‐O‐galactoside and 1‐O‐caffeoylquinic acid were identified as major components of whole BF sprouts. The leaves/stems of the sprouts had higher total phenolic and flavonoid contents and lower IC50 values in DPPH• and ABTS•+ scavenging assays than whole sprouts or roots. The roots of the sprouts had the highest polygalacin D content (1.44 mg/g). We also determined the effects of different parts of BF sprouts on RAW 264.7 macrophage cells. When these cells were stimulated with lipopolysaccharide (LPS), their nitrite and pro‐inflammatory cytokine production increased. BF sprouts suppressed the LPS‐induced production of nitrite, tumor necrosis factor‐α, and interleukin‐6 in a concentration‐dependent manner without causing any cytotoxic effects. Nitrite and pro‐inflammatory cytokine production were significantly inhibited by the roots and leaves/stems, respectively. The inhibitory effects of BF sprouts on LPS‐stimulated inflammatory responses in RAW 264.7 macrophage cells were associated with suppressed NF‐κB activation. These findings suggest that BF sprouts could be a valuable source of bioactive compounds and exert anti‐inflammatory effects due to their polygalacin D, deapi‐platycodin D3, and polyphenol content. Balloon flower sprouts could be a valuable source of bioactive compounds and exert anti‐inflammatory effects via suppression of NF‐kB activation due to their polygalacin D and polyphenol content.
... Furthermore, another component was identified as 4-CQA by comparing the retention time with that of the corresponding standard substance, as well as the results of ultra-performance liquid chromatography coupled with quadrupole/time-of-flight mass spectrometry (UPLC-Q-TOF-MS/ MS). 3-CQA, 4-CQA, 3, 4-diCQA, 4, 5-diCQA, and 3, 5-diCQA are isomers of caffeoylquinic acid derivatives, some of which have been reported to exhibit antioxidative activities and to induce granulocytic differentiation in HL-60 cells (Maruta et al. 1995;Mishima et al. 2005;Kim et al. 2011;Hwang et al. 2014). The structures of the seven components are shown in Figure 1. ...
Context: The dried fruits of Arctium lappa L. have been used in two forms in traditional Chinese medicine; crude and stir-heating Fructus Arctii. However, its processed product possesses better activity.
Objective: In this study, the chemical constituents of both crude and processed Fructus Arctii and their antiproliferative activities were evaluated.
Materials and methods: The seven main active components in crude and various processed Fructus Arctii were quantitatively determined using high-performance liquid chromatography (HPLC). According to the actual amount in crude and five processed samples, seven single components were combined as multi-component combinations with six different proportions. The antiproliferative activities of these compatibility component groups were examined using the CCK-8 assay.
Results: During the heating process, the proportion of the seven main components changed dynamically. The contents of 3-caffeoylquinic acid (3-CQA), 3,5-dicaffeoylquinic acid (3,5-diCQA), and arctiin (ARC) declined, while the contents of 4-caffeoylquinic acid (4-CQA), 3,4-dicaffeoylquinic acid (3,4-diCQA), 4,5-dicaffeoylquinic acid (4,5-diCQA), and arctigenin (ARG) increased very significantly.
Discussion and conclusions: The results also indicated that seven components in the processed samples had higher cytotoxic profiles against HL-60 cells than those in the crude sample. Therefore, the heating process may enhance the antitumor activity of Fructus Arctii by changing the proportion of active components.
... (Fam. Asteraceae) 24 ...
Este Manual es resultado de un estudio Etnografico sobre plantas medicinales en la Ciudad de Bogotá durante 2016-2017 , por investigadores de la Fundación Universitaria Agraria de Colombia.
... (Fam. Asteraceae) 24 ...
... (Fam. Asteraceae) 24 ...
Colombia es un país megadiverso cuya riqueza biológica representa una ventaja competitiva importante para el país, esto dado a su posición geográfica, con salida a dos océanos, Atlántico y Pacífico, con una gran variedad de microclimas y pisos térmicos, con plenitud de especies vegetales cultivables en diferentes suelos y con varias cosechas al año. Es por ello que, Colombia se destaca en América del Sur por su riqueza biológica por kilómetro cuadrado, ubicándola en los primeros puestos a nivel mundial.
Por lo anterior, el programa de Ingeniería Agroindustrial de la Fundación Universitaria Agraria de Colombia, considera pertinente presentar este documento sobre Productos Naturales con temáticas específicas en metabolitos secundarios y aceites esenciales como material de consulta que sirve de base para
... In the current study, we found that edible burdock, East Indian lotus root, strawberries, and spinach showed the highest Total-ORAC value as calculated from individual H-ORAC and L-ORAC measurements, which was consistent with previous findings (Takebayashi et al., 2013). In particular, it has been reported that edible burdock has a relatively high ORAC value among vegetables (Mikami-Konishide et al., 2013) and contained caffeoylquinic acid derivatives such as chlorogenic acid and dicaffeoylquinic acid, which have antioxidant activity (Maruta et al., 1995). However, the H-ORAC and L-ORAC values obtained in this study are generally slightly lower than the values reported previously (Mikami-Konishide et al., 2013;Takebayashi et al., 2013;Wu et al., 2004), which may be attributable to the specific cultivar, climate, and growing conditions (Mikami-Konishide et al., 2013). ...
Radical scavenging and singlet oxygen quenching activities of 32 kinds of fruits and vegetables typically consumed in Japan were evaluated using both the oxygen radical absorbance capacity (ORAC) and singlet oxygen absorption capacity (SOAC) methods. Total-ORAC and SOAC values correlated with total polyphenol (r = 0.92) and carotenoid (r = 0.85) contents. From the data of daily fruit and vegetable intake (110.0 and 286.4 g, respectively) in the National Health and Nutrition Survey in Japan, daily ORAC and SOAC intakes were estimated to be 3177.7 µmol trolox equivalents/day and 1610.3 µmol α-tocopherol equivalents/day, respectively. The major contributors to ORAC intake were apples, Satsuma mandarins, edible burdock, and onions, accounting for 44.3% of the total; whereas Japanese squash, carrots, tomatoes, and spinach accounted for 73.2% of total SOAC intake. Total antioxidant capacity assessment of foods may facilitate the identification of relationships between antioxidant intake and disease risk reduction.
... Concerning the basis of its medicinal use, data indicate that Bardanae radix is rich in caffeoylquinic acid isomers [1,3], with dicaffeoylquinic acid derivatives being quantified at 75.4% and 1,5-di-O-caffeoyl-4-O-maloylquinic acid representing 44% of the total isomers [4], but that the content also comprisesnumerous other secondary metabolites such as tannin-iron complexes, various polyacetylenes and sulphuric actylene compounds, essential oils, guainolides and bitter compounds, lignans (e.g., arctigenin, arctiin,) and sterols (e.g., sitosterol, stigmasterol) [2]. Studies regarding the metabolic profile of the compounds of burdock plant pieces indicated caffeoylquinic acid derivates and luteolin and quercetin rhamnosides occur in the root part, caffeoylquinic acid and quercetin, quercitrin and luteolin derivates in the leaves, whereas cynarin and chlorogenic acid are dominant in the seeds [5]. ...
Confounding by indication is a critical challenge in evaluating the effectiveness of surgical interventions using observational data. The threat from confounding is compounded when using medical claims data due to the inability to measure risk severity. If there are unobserved differences in risk severity across patients, treatment effect estimates based on methods such a multivariate regression may be biased in an unknown direction. A research design based on instrumental variables offers one possibility for reducing bias from unobserved confounding compared to risk adjustment with observed confounders. This study investigates whether a physician’s preference for operative care is a valid instrumental variable for studying the effect of emergency surgery. We review the plausibility of the necessary causal assumptions in an investigation of the effect of emergency general surgery (EGS) on inpatient mortality among adults using medical claims data from Florida, Pennsylvania, and New York in 2012–2013. In a departure from the extant literature, we use the framework of stochastic monotonicity which is more plausible in the context of a preference-based instrument. We compare estimates from an instrumental variables design to estimates from a design based on matching that assumes all confounders are observed. Estimates from matching show lower mortality rates for patients that undergo EGS compared to estimates based in the instrumental variables framework. Results vary substantially by condition type. We also present sensitivity analyses as well as bounds for the population level average treatment effect. We conclude with a discussion of the interpretation of estimates from both approaches.
... The roots and seeds of A. lappa have been used as food and traditional medicine. Previous studies have reported that A. lappa has anti-inflammatory (Lin, Lu, Yang, Chuang, & Ujiie, 1996;de Almeida et al., 2013;Maghsoumi-Norouzabad et al., 2016) and anti-oxidative effects (Maruta, Kawabata, & Niki, 1995). Although C. gladiata and A. lappa have anti-inflammatory activity and are widely used in food and traditional medicine, to our knowledge, their combined therapeutic potential and regulatory mechanisms in inflammatory diseases such as IBD have yet to be explored. ...
... Burdock root is not only a healthy and nutritive dietary supplement, it was also a folk herbal medicine with heat-clearing and detoxifying effect [1]. Pharmacological studies indicated that burdock root has antioxidant [2], antiallergic [3], antiinflammatory [4] and hepatoprotective activities [5]. Caffeoyl quinic acid derivatives are considered to be one of the main active ingredients, such as 1,3-, 1,4-, 1,5-dicaffeoylquinic acids, which were all positional isomers in chemical structure [6,7]. ...
Burdock roots are healthy dietary supplements and a kind of famous traditional Chinese medicine, which contains large amounts of caffeoylquinic acid derivatives. However, little research has been reported on the preparative separation of these compounds from burdock roots. In the present study, a combinative method of HSCCC and semi-preparative HPLC was developed for the semi-preparative separation of caffeoylquinic acid derivatives from the burdock roots. The ethyl acetate extract of burdock roots was first fractionated by MCI macroporous resin chromatography and give three fractions (Fr. 1-3) from the elution of 40% methanol. Then, these three fractions (120 mg) were separately subjected to HSCCC for purification with the solvent system composed of petroleum ether-ethyl acetate-methanol-water at different volume ratios, and the mixtures were further purified by semi-preparative HPLC. As a result, a total of eight known caffeoylquinic acid derivatives including 3-O-caffeoylquinic acid (32.7 mg, 95.7%), 1,5-O- dicaffeoylquinic acid (4.3 mg, 97.2%), 3-O-caffeoylquinic acid methyl ester (12.1 mg, 93.2%), 1,3-O-dicaffeoylquinic acid (42.9 mg, 91.1%), 1,5-O-dicaffeoyl-3-O-(4-maloyl)-quinic acid (4.3 mg, 84.5%), 4,5-O-dicaffeoylquinic acid (5.3 mg, 95.5%), 1,5-O-dicaffeoyl-3-O-succinylquinic acid (8.7 mg, 93.4%), and 1,5-O-dicaffeoyl-4-O-succinylquinic acid (1.7 mg, 91.8%), and two new compounds were obtained. The new compounds were 1,4-O-dicaffeoyl-3-succinyl methyl ester quinic acid (14.6 mg, 96.1%) and 1,5-O-dicaffeoyl-3-O-succinyl methyl ester quinic acid (3.1 mg, 92.6%), respectively. The research indicated that the combination of HSCCC and semi-preparative HPLC is a highly efficient approach for preparative separation of the instability and bioactive caffeoylquinic acid derivatives from natural products.
... It is widely used in popular medicine all over the world for its well-known therapeutic applications. It has anti-bacterial, antifungal (12), diuretic (13), anti-oxidant (14) anxiolytic (15), anti-platelet aggregating (16) and HIV-inhibitory properties (17). Bacterial resistant to antibiotics is increasing, requiring introduction of new and safe antibacterial substances. ...
Introduction: Arctium lappa (Great burduck) and Artemesia absinthium are medicinal plants that some of their antibacterial and antivirus properties have been suggested in nutritional industries. The objective of this research was to study the effects of A. lappa and A. absinthium on some microorganisms including Pseudomonads aeraginosa, Haemophilus influenza, Bacillus subtilis, Bacillus cereus, Klebsiella pneumonia and Staphylococcus aureus. Methods: Extracts were prepared by maceration method and tested on Mueller Hinton agar medium based on disc diffusion method. The minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) were determined by micro-dilution method. Antibiotic disks used for controlling and standardizing the examination. Results: The extracts of A. lappa and A. absinthium had significant effect on S. aureus. The MIC and MBC concentrations of the extract of A. lappa on B. subtilis were respectively 600 and 750 mg/ml. Also, these values were 230 and 540 mg/ml for H. influenza. Extract of A. absinthium showed more inhibitory effect on B. subtilis. All extracts showed inhibitory effect on B. cereus. The extracts of A. lappa and A. absinthium had inhibitory effects on H. influenza and P. aeraginosa. Among antibiotics, only Ofloxacin and Ciprofloxacin had effects on H. influenza. Extract of A. lappa showed flimsy effect on K. pneumonia, while extract of A. absinthium had no effect on this bacterium. Conclusion: Due to the effects of A. lappa and A. absinthium on some bacteria, they might be good substitutes for synthetic substances.
... Compounds were identified by their retention times, UV absorbance spectra, and MS fragmentation pattern and numbered in conformity with the IUPAC numbering system (IUPAC, 1976). For peak assignment, we took as references LC−MS/MS characterizations from Lin and Harnly (2008), Jaiswal and Kuhnert (2011) and Maruta et al. (1995). Isomers were assigned by using the appropriate standards (chlorogenic acid, caffeic acid). ...
Ethnopharmacological relevance:
Chicory (Cichorium intybus L.) is an indigenous vegetable widely cultivated in Europe, America and Asia. In ancient times, the leaves, flowers, seeds, and roots have been used as a wealth of health benefits including its tonic effects, the ability to ease digestive problems and to detoxify liver. In Indian traditional therapy, chicory was known to possess antidiabetic effect. In the traditional medicine of Bulgaria and Italy, chicory was used as hypoglycemic decoctions.
Aims of the studies:
We wanted to obtain the complete chemical composition of the natural chicoric acid extract (NCRAE), a chicory root extract rich in chicoric acid, which previously showed its glucose tolerance effect in normal rats. To investigate if the whole NCRAE is required to be effective, we performed a comparative in vivo experiment on STZ diabetic rats treated either with NCRAE or a mixture composed of the two major compounds of NCRAE.
Materials and methods:
LC-MS method has been used to analyze the exhaustive composition of NCRAE: we have determined that chicoric acid and chlorogenic acid represented 83.8% of NCRAE. So, we have prepared a solution mixture of chicoric acid and chlorogenic acid named SCCAM, in order to compare in vivo the antidiabetic effects of this last and NCRAE in streptozotocin diabetic rats. In vitro experiments were performed on L6 cell line both for glucose uptake and for the protective effect against H2O2 oxidative stress. Also, we have evaluated DPPH and ORAC (Oxygen Radical Absorbance Capacity) antioxidative capacities of the two compositions.
Results:
The LC-MS analysis confirmed the high abundance of chicoric acid (64.2%) in NCRAE and a second part of NCRAE is composed of caffeoylquinic acids (CQAs) at 19.6% with among them the chlorogenic acid. This result has permitted us to prepare a mixture of synthetic L-chicoric acid (70%) and synthetic chlorogenic acid (30%): the solution is designated SCCAM. Our results showed that both NCRAE and SCCAM are able to improve a glucose tolerance in STZ diabetic rats after a subchronic administration of seven days. Alone NCRAE allows to significantly decrease the basal hyperglycemia after six days of treatment. To explain these difference of effects between NCRAE and SCCAM, we have compared their in vitro effects on the L6 muscle cell line both for the insulin sensitizing effect and for their protective action in pretreatment against H2O2. We have also compared their antioxidant capacities. In conclusion, we demonstrated that NCRAE, a natural extract of chicory (Cichorium intybus) rich in CRA and CQAs improves glucose tolerance and reduces the basal hyperglycemia in STZ diabetic rats.
... Therapeutic activity has been attributed to flavonoids and lignans content of burdock roots. It has been reported that antioxidative, anti-inflammatory and hepatoprotective effects are due to the caffeoylquinic acid derivatives (Maruta et al., 1995;Lin et al., 1996) and that antiproliferative and apoptotic effects are attributable to the presence of arctigenin (Matsumoto et al., 2006) and lappaol A, C and F (Ming et al., 2004). ...
The present study aims to evaluate the potential uses of hydroalcoholic extracts obtained from Romanian native wild-growing plants. The hydroalcoholic extracts were obtained from the burdock roots and respectively the aerial parts of birdeye speedwell. The extracts were characterised by HPLC (quantifying 13 compounds in the V. persica extract, 6 compounds in the A. lappa extract and confirming the presence of arctiin and arctigenin in the burdock extract). The antioxidant potential of the crude extracts was evaluated using two methods: the DPPH assay (79.91% for speedwell extract, 76.23% for burdock extract) and the phosphomolybdate method (296.5 mg/g ascorbic acid equivalents for burdock, 324.4 mg/g for speedwell). The crude extracts were found to be active against both fungal lines used (Aspergillus niger and Penicillium hirsutum), inhibition zones - 17.1 mm and 13.1 mm against P. hirsutum, respectively ca. 22 mm for both extracts against A. niger. The cytogenetic effects (assessed using the Allium cepa assay) revealed a series of chromosomal aberrations and nuclear aberrations induced in the meristematic root cells. The antiinflammatory effect, estimated in two inflammation experimental models, showed a significant effect, especially for the speedwell extract. The results recommend the evaluated extracts as promising sources of biologically-active compounds.
... Burdock root, Artium lappa, is a popular vegetable in Japan and Korea. It contains a considerable amount of polyphenols such as chlorogenic acid, caffeoylquinic acid, hydroxycinnamoylquinic acids and related compounds and indicates antioxidant activity (Maruta, Kawabata & Niki, 1995;Lin & Harnly, 2008). Okazaki et al. (2013) prepared A. awamori-fermented burdock root to improve the functional property of burdock, and indicated that the intake improved intestinal environment and suppressed obesity in rats fed a high fat-diet. ...
Problem statement: Though alloxan-induced mouse hyperglycemia was ameliorated by feeding of 5 % Asperagillus awamori (A. awamori)-fermented burdock root diet (fermented burdock diet), it is unclear whether the anti-hyperglycemia activity is due to A. awamori or antioxidant activity induced by the fermentation.Methods: A 0.05 % A. awamori diet was prepared. Acatalasemic mice, having a quite low catalase activity in blood, were divided three groups, and each group fed control, A. awamori and the fermented burdock diets for 14 weeks, separately. Then, alloxan monohydrate (200 mg/ kg of body weight) was intraperitoneally administrated to each mouse. Glucose, insulin, C-peptide contents in blood and glucose tolerance tests (GTTs) were examined. Results: Incidence of alloxan-induced hyperglycemia in acatalasemic mice maintained with the A. awamori diet or the fermented burdock diet was low (20 or 25%) compared to that (75%) maintained with the control diet. Feeding the A. awamori diet ameliorated insulin, C-peptide in blood and GTT like as mice fed the fermented burdock diet. It indicated that A. awamori in these diets plays an important role for the prevention of alloxan-induced hyperglycemia.Conclusions: It is suggested that A. awamori has the anti-hyperglycemia activity.
... Concerning the basis of its medicinal use, data indicate that Bardanae radix is rich in caffeoylquinic acid isomers [1,3], with dicaffeoylquinic acid derivatives being quantified at 75.4% and 1,5-di-O-caffeoyl-4-O-maloylquinic acid representing 44% of the total isomers [4], but that the content also comprisesnumerous other secondary metabolites such as tannin-iron complexes, various polyacetylenes and sulphuric actylene compounds, essential oils, guainolides and bitter compounds, lignans (e.g., arctigenin, arctiin,) and sterols (e.g., sitosterol, stigmasterol) [2]. Studies regarding the metabolic profile of the compounds of burdock plant pieces indicated caffeoylquinic acid derivates and luteolin and quercetin rhamnosides occur in the root part, caffeoylquinic acid and quercetin, quercitrin and luteolin derivates in the leaves, whereas cynarin and chlorogenic acid are dominant in the seeds [5]. ...
This work aimed to study the potential effects of four Arctii folium extracts, 5 mg gallic [GAE] acid equivalents per 1 mL sample, on six antibiotics (Ampicillin/AM, Tetracycline/TE, Ciprofloxacin/CIP, Sulfamethoxazole-Trimethoprim/SXT, Chloramphenicol/C and Gentamicin/CN) tested on four Gram-positive (Staphylococcus aureus ATCC 6538, Staphylococcus aureus ATCC 25923, Enterococcus faecalis ATCC 29212, and Staphylococcus epidermidis ATCC 12228) and five Gram-negative (Proteus mirabilis ATCC 29245, Escherichia coli ATCC 35218, E. coli ATCC 11229, E. coli ATCC 8739, and Bacillus cereus ATCC 11778) bacteria. Arctii folium extracts were the whole ethanol extract/W and subsequent ethyl acetate/EA, aqueous/AQ, and chloroform/CHL fractions. Chemical qualitative analysis (HPTLC method) emphasized five main polyphenol compounds in Arctii folium polar extracts: chlorogenic acid (Rf≈0.52/0.55) and its isomer, 1,5-di-O-caffeoylquinic acid (Rf≈0.90/0.92), plus cynarin (Rf≈0.77), hyperoside (Rf≈0.68/0.64) and isoquercitrin (Rf≈0.69/0.71). Microbiological screening indicated Arctii folium polar extracts (AQ and W) efficacy on S. epidermidis ATCC 12228; the MIC values were in the range of common antibiotics, being 32 and 128 μg GAE per mL sample respectively. The unpredictable effects (stimulatory or inhibitory) of Arctii folium extracts in combination with typical antibiotics as well as a potential use of the whole ethanol extract/W for restoring the antimicrobial potency of susceptible antibiotics have also been evidenced.
Eleven new acyl-quinic acids (AQAs) 1a-9, and 18 known AQAs 10-27 were isolated from the root bark of Acanthopanax gracilistylus W. W. Smith (Acanthopanacis Cortex). The planar structures of 1a-9 were determined based on their HR-ESIMS, IR, and NMR data. The absolute configurations of 1a-6 were identified by comparing the experimental and the calculated electronic circular dichroism (ECD) spectra. This is the first report of the isolation of AQAs from Acanthopanacis Cortex. Notably, 1a-6 were determined as unusual oxyneolignan-(-)-quinic acids heterodimers, representing a new class of natural products. The inhibitory activities of 1a-27 on neutrophil elastase (NE) and cyclooxygenase-2 (COX-2) were studied in vitro, and the results indicated they possessed significant inhibitory activities on COX-2. Among them, the IC50 values of 1a-9 were 0.63±0.014, 0.75±0.028, 0.15±0.023, 0.63±0.016, 0.30±0.013, 35.63±4.600, 8.70±1.241, 16.51±0.480, 0.69±0.049, 0.39±0.017, and 0.26±0.080 μM, respectively. This study represents the inaugural disclosure of the anti-COX-2 constituents found in Acanthopanacis Cortex, thereby furnishing valuable insights into the exploration of novel COX-2 inhibitors derived from natural reservoirs.
Metabolic syndrome (METS) is a complex disorder that predisposes an affected person to an increased risk of diabetes and cardiovascular disease. Bitter Asteraceae plants contain several compounds active against METS that can be used as an alternative preventive therapy. Our previous work showed that a natural chicory extract (NCRAE) containing chicoric acid (CRA) and chlorogenic acid (CGA) in a molar ratio of 70/30 exhibited an antioxidant, insulin sensitization and anti-hyperglycemic effect. The present study was designed to evaluate the preventive effects of an NCRAE-like extract against METS in a complementary natural pharmacotherapeutic approach. An original Asteraceae infused drink containing the NCRAE CRA/CGA molecular ratio equivalent was prepared from dandelion (Taraxacum officinale L.) and burdock (Arctium lappa L.). The anti-METS effect of this drink was evaluated on the fructose-rat model for 8 weeks. Body weight, blood biochemistry, hepatic glucose-6-phosphatase, arterial blood pressure glucose and insulin tolerance were evaluated after 8 weeks. Our results show that daily oral intake of the Asteraceae infused drink led to a reduction of body weight gain, hyperglycemia, hypertriglyceridemia, insulin resistance and hypertension. Moreover, rat-by-rat analysis of the insulinemia measures revealed two types of responders. One sub-group of subjects demonstrated normal insulinemia and the other subgroup demonstrated hyperinsulinemia. This hyperinsulinemia, associated with the inhibition of the glucose-6-phosphatase activity in the liver tissue, may suggest an insulin release caused by CGA. The present study suggests that this original infusion of dandelion leaves and burdock roots may be used as an adjuvant therapy to prevent metabolic syndrome.
Diabetes mellitus (DM) type 2 is amongst the most common chronic diseases, being responsible for various problems in humans and contributing to increased mortality rates worldwide. Fructooligosaccharide, which can be produced from the roots of burdock (Arctium lappa L.), has been shown to have a wide range of pharmacological proprieties, including antiviral, anti-inflammatory, hypolipidemic, and antidiabetic effects. Moreover, burdock also contains chlorogenic acid, which has been used in traditional medicine as an antioxidant. Considering its natural origin and minimal toxicity, burdock fructooligosaccharides (BFO) has gained considerable attention from researchers owing its wide, efficient, and beneficial action against DM. Although the effectiveness of fructooligosaccharide and chlorogenic acid has been extensively discussed, limited information is available on the application of burdock for DM treatment. In this review, we discuss the beneficial contributions, and the recent in vitro and in vivo analytical findings on A. lappa extract as DM therapy.
In this study, we investigated the effects of dicaffeoylquinic acid derivatives, including 1,4-di-O-caffeoylquinic acid (1,4-DCQA), 3,4-di-O-caffeoylquinic acid (3,4-DCQA), 3,5-di-O-caffeoylquinic acid (3,5-DCQA), 4,5-di-O-caffeoylquinic acid (4,5-DCQA), and 1,5-di-O-caffeoylquinic acid (1,5-DCQA) on glucose-stimulated insulin secretion (GSIS) activity and α-glucosidase activity were compared in rat INS-1 pancreatic β-cells. The α-glucosidase inhibitory activities of dicaffeoylquinic acid derivatives were as follows: 1,4-DCQA > 1,5-DCQA > 3,4-DCQA > 4,5-DCQA > 3,5-DCQA. In INS-1 cells, dicaffeoylquinic acid derivatives showed no cytotoxic effect at any concentration (2.5–10 μM). In addition, the GSIS activities of dicaffeoylquinic acid derivatives were as follows: 4,5-DCQA > 3,4-DCQA > 1,4-DCQA > 3,5-DCQA > 1,5-DCQA. Treatment of INS-1 cells with 4,5-DCQA resulted in a marked increase in protein expression of extracellular signal-regulated protein kinases (ERK), insulin receptor substrate-2 (P-IRS-2), Akt, phosphoinositide 3-kinase (P-PI3K), and pancreatic and duodenal homeobox-1 (PDX-1), which might be related to its GSIS activity in INS-1 cells. These findings indicate that the location of the dicaffeoyl functional group influences the anti-diabetic activity of quinic acid.
Background
The traditional pharmacopoeia is full of potential resources for molecules with therapeutic effects involving the inhibition of enzymes linked to some diseases.
Objective
This work aimed to test invitro the neuroprotective activity against Alzheimer's disease (AD) combined with the antioxidant effect of root extracts obtained by water, water / methanol and ethyl acetate of the endemic Arctium minus. subsp. atlanticum. native of Algeria.
Methods
The different extracts of the root of the studied plant were obtained by decoction or maceration. The inhibitory effect of acetyl / butyryl cholinesterase (AChE/BChE) was achieved by a colorimetric method. Similarly, the antioxidant activity was measured, based on several mechanisms: 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) and galvinoxyl (GOR) radicals free scavenging assays, β-carotene bleaching inhibition activity, and cupric ion reducing antioxidant capacity (CUPRAC).
Results
In the various tests carried out, the ethyl acetate extract (EAE) possessed the most powerful antioxidant and anticholinesterase activities in comparison with the other samples. The IC50 and A0.5 values of DPPH, GOR, β-carotene, CUPRAC, anti-AChE and anti BChE assays were 69.45±5.49, 28.87±0.18, 121.58±16.76, 37.41±1.59, 265±21 and 240±6.3 µg / mL, respectively. Likewise, a correlation can be deduced between the type of extract and the potent antioxidant / anticholinesterase potential.
Conclusion
This work evokes for the first time the anticholinesterase potential combined with the antioxidant effect of Algerian Arctium minus. subsp. atlanticum. This association between the two effects could be effective in the fight against AD and therefore, the use of this natural resource may be possible in combating this aspect of neurodegeneration.
Arctium lappa (A. lappa) is one of the most significant edible medicinal plants with high antibacterial effects, in which it could be supposed to grow with more beneficial effects under administration by salicylic acid and chitosan based biofertilizers. Accordingly, the effects of salicylic acid, chitosan, and 50% moisture discharge were investigated in this work to see the antimicrobial treatments of some foodborne pathogens effects by A. lappa. To this aim, plants were cultivated based on different concentrations of salicylic acid and chitosan with/without drought stress, in which their extracted essential oils were examined for showing the antimicrobial effect against different bacterial agents. The results indicated that the salicylic acid and chitosan administrated A. lappa could work with improved inhibitory functions. Comparing with referenced antibiotics showed even higher antimicrobial effects of A. lappa against the targeted bacterial agents, in which the species with 14 mmol of salicylic acid and 2 g/l of chitosan was a distinguished one for approaching the purpose. Consequently, the achievements of this work could be further investigated for producing novel antibiotic drug agents.
Burdock root in natura has compounds with functional activity. However, few studies have evaluated the retention of these compounds after thermal processing. Thus, the present study aimed to evaluate the retention of functional compounds in burdock root-derived products. The processes consisted of blanching (98 ºC/4 min; BR1) followed by cooking in oil (95 ± 4 ºC/10 min; BR2), root infusion (2%, 98 ºC/10 min; BR3), the infusion residue (BR4); as well as the production of two types of chips: roasted burdock roots (120 ºC/20 min; BR5) and fried burdock roots (150 ± 4 ºC/4 min; BR6). All samples were evaluated for the content of total phenolics (TPC), antioxidant capacity (AC), total fructooligosaccharides (FOSt), and bifidogenic activity in vitro. The control (BR1) presented TPC of 162.07 mg gallic acid equivalents (GAE)/100 g, AC of 0.42 μmol Trolox equivalent/100 g, and 0.71 g/100 g of FOSt. These levels changed significantly for all processed products (BR2 to BR6) (p < 0.05) when compared to the control, with a reduction of 46–99% of TPC (BR4 and BR6), 47%–99% of AC (BR5 and BR6) and 40–63% of FOSt (BR5 and BR6). The results showed that the retention of TPC, AC, and FOSt in burdock-derived products was affected by thermal treatment, which should be considered during root processing. Roasted burdock chips have proven to be an alternative for a new convenience product with functional properties.
In the present investigation fresh leaf sheaths of locally cultivated cardoon (Cynara cardunculus L. var. altilis DC) populations and artichoke (Cynara cardunculus L. var. scolymus L.) edible sprouts from northern and central Italy were analysed for their total and individual phenolic content. Twelve phenolic compounds, belonging to monocaffeoylquinic, dicaffeoylquinic, and dicaffeoyl-succinylquinic acids were identified by high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) and quantified by HPLC-diode array detection (DAD). A significant variability was assessed within cardoon accessions cultivated in the same region, with total phenolic content in the range 20,835-27,051, 11,268-31,937, 11,911-30,016, 8853-34,961, 8794-22,628 mg kg⁻¹ of dry matter (DM) in artichoke sprouts, and cardoon stalks from Emilia-Romagna, Tuscany, Piedmont, and Marche, respectively. Four cardoon samples, one from Emilia-Romagna (Cardo di Cervia), one from Tuscany (Cardo di Lucca), and two from Piedmont (Cardo Gobbo di Nizza Monferrato), showed a total phenolic content higher than 30,000 mg kg⁻¹ DM. The present investigation represents a first contribution to characterise for their phenolic composition Italian cardoon and artichoke populations that still play an important role in local economy and are highly appreciated for their sensory properties.
1,3,5-Tri-O-caffeoyl quinic acid is a caffeoylquinic acid derivative isolated from the roots of Arctium lappa L. Our previous studies have revealed that the ethyl acetate extract of the roots of A. lappa L. and the caffeoylquinic acids contained in it possess antioxidant properties, especially 1,3,5-tri-O-caffeoyl quinic acid. The present study aimed to investigate the protective effects of 1,3,5-tri-O-caffeoyl quinic acid against hydrogen peroxide-induced oxidative stress and explore the underlying mechanism. We found that 1,3,5-tri-O-caffeoyl quinic acid prevented the decline of cell viability and excessive release of lactate dehydrogenase induced by hydrogen peroxide. In addition, Hoechst 33 342 staining and Annexin V-PI double staining showed that 1,3,5-tri-O-caffeoyl quinic acid inhibited hydrogen peroxide-induced neuronal cell apoptosis. 1,3,5-Tri-O-caffeoyl quinic acid reduced the excessive production of intracellular reactive oxygen species, decreased the malondialdehyde content, and improved the activity of superoxide dismutase. Furthermore, 1,3,5-tri-O-caffeoyl quinic acid restored the loss of mitochondrial membrane potential in SH-SY5Y cells induced by hydrogen peroxide. 1,3,5-Tri-O-caffeoyl quinic acid downregulated the overexpression of proapoptotic proteins, including Bax, cytochrome c, cleaved caspase-9, and cleaved caspase-3 as well as promoted the expression of the antiapoptotic protein Bcl-2. Moreover, the phosphorylation of mitogen-activated protein kinases induced by hydrogen peroxide was inhibited by 1,3,5-tri-O-caffeoyl quinic acid. Pretreatment with 1,3,5-tri-O-caffeoyl quinic acid also promoted the activation of phosphorylated Akt. Taken together, these findings suggest that 1,3,5-tri-O-caffeoyl quinic acid exerts protective effects against hydrogen peroxide-induced neuronal apoptosis. In addition, inhibition of the mitogen-activated protein kinase signaling pathway and the activation of Akt are implicated in the antioxidant activity of 1,3,5-tri-O-caffeoyl quinic acid, giving new insight in searching for a compound with antioxidant activity for the treatment of oxidative stress-associated neurological diseases.
The review summarizes information from the literature on the distribution, study of the composition and biological activity of metabolites, total extracts of plants of the genus Arctium L. of the world flora. In Russia, the roots of three species are allowed to be harvested and used: A. lappa, A. tomentosum, A. minus. To date, the most studied composition of metabolites and pharmacological properties of great burdock. The chemical composition of A. atlanticum, A. debrayi, A. leiobardanum, A. neumani, A. platylepis, A. pseudarctium, A. sardaimionense, A. scanicum, A. nemorosum and A. palladini has not been studied. About 360 substances related to polysaccharides, sesquiterpenes, triterpenes, fatty acids, phenolcarbonic acids, tannins, vitamins, lignans, sterols, polyacetylenes, amino acids, alkaloids, flavonoids, macro-and microelements and other were isolated and identified from the studied species. There are only a few publications about pharmacological activity of Arctium nemorosum, A. palladini, A. tomentosum and A. minus, and there is no information for other types. Total extracts and individual compounds of the studied burdock species in the experiment have a wide range of pharmacological activity. The information provided in the review shows that plants of the genus Arctium L., are promising for creating effective medicines. In addition, the fragmentation and lack of information on the composition of metabolites, pharmacological activity of most species of the genus burdock opens up great opportunities for researchers.
The roots and tubers of the Asteraceae family are known as a source of various oligosaccharides, and chicory roots and Jerusalem artichoke have stood out for its commercial viability. However burdock root (Arctium lappa L.), which is adapted to temperate climate, moist, and sandy soil, is still unknown as health food in the western world. This review showed the potential of burdock roots as a source of prebiotic fibers, chlorogenic acids, cinnarine, lignans, and quercetin. The extraction methods of burdock functional compounds are made with water, temperature and time variations only. Biological assays showed antioxidant activity, anti-inflammatory, and hypolipidemic properties, and gastric mucosal defense mechanisms, among others. Therefore, the use of burdock roots as functional food should be encouraged in countries that have imported products derived from other roots of the same family for health benefits.
A chemical investigation of Artemisia sieversiana, one of the Mongolian wild pasture forage plants led to the isolation and identification of 15 compounds. We revealed that lignan type compounds dominantly contained in spring samples and lignans, terpenoids, flavonoids in summer samples, terpenoids, flavnoids, chlorogenic acid derivatives in autumn sample. Six of them lignans (1-6), three chlorogenic acid derivatives (7-9), and six flavonoids (10-15) were isolated from A. sieversiana. Сиверсийн шарилжны химийн найрлагын хөдлөл зүйн судалгаа Бид Монгол орны малын тэжээлийн ургамалын нэг болох Сиверсийн шарилжны химийн найрлгын хөдлөлзүйн судалгааг явуулж хавар, зун, намрын дээжнээс 15 бодис цэврээр ялгаж, бодисын молекулын бүтэц байгууламжийг тогтоов. Уг ургамлын хаврын дээжинд лигнаны төрлийн бодисууд, зуны дээжинд лигнан, терпенойд, флавнойдууд, намрын дээжинд терпенойд, флавонойд, хлорогений хүчлийн уламжлалт нэгдлүүд зонхилж байгааг тогтоолоо. Дээрхи 15 бодисын зургаа нь лигнаны төрлийн бодис(1-6), 3 нь хлорогений хүчлийн уламжлалт нэгдлүүд(7-9), 6 нь флавоноид нэгдлүүд (1015) байв. Түлхүүр үг: Сиверсийн шарилж, лигнан, флавонойд, хлорогений хүчил
Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidences demonstrate that CQAs have a wide range of biological activities, such as anti-oxidation, anti-bacterial, anti-parasitic, neuroprotective, anti-inflammatory, anti-cancer, anti-viral, and antidiabetic effect. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis) and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents. Key words: Caffeoylquinic acids; Chlorogenic acid; Structure; Biosynthesis; Total synthesis; Bioactivity. .
Artemisia sieversiana is an annual herbaceous plant distributed throughout Central and East Eurasia and is regarded as an undesirable forage plant in Mongolia. It affects livestock, so information about its chemical composition is needed. We isolated three new sesquiterpenoids (1–3) and known compounds from A. sieversiana and investigated their activities. The absolute configuration of 1 was established using single-crystal X-ray diffraction crystallography, and its configuration differed from those of reported compounds with similar structures. Two additional new sesquiterpenoids (2 and 3) with similar structures were identified, and their configurations were determined. The trypanocidal activities of the isolated compounds (1–18) against Trypanosoma congolense and the pathogen responsible for fatal trypanosomosis in animals were estimated. Flavonoids and lignans were identified as active compounds with IC50 values ranging from 2.9 to 90.2 µM
Five undescribed caffeoylquinic acid derivatives (CQAs), along with fifteen known CQAs, were isolated from the roots of Arctium lappa L.(burdock). The chemical structures of compounds were determined using extensive spectroscopic analyses, including UV, IR, NMR and MS. Further in vitro bioactive investigation demonstrated the neuroprotective effects of these compounds against the neurotoxicity of hydrogen peroxide (H2O2) and N-methyl-D-aspartate (NMDA). 1,3,5-tri-O-caffeoylquinic acid and 1,4,5-tri-O-caffeoylquinic acid significantly reduced H2O2-induced human neuroblastoma SH-SY5Y cell death with concentration for 50% of maximal effect (EC50) values of 17.3 and 19.3 μM. Meanwhile, 3,5-di-O-caffeoyl-1-O-maloylquinic acid displayed protective effect against NMDA-induced cell injury with EC50 values of 18.4 μM. Overall, the more caffeoyl, the better the antioxidant activity, while the maloyl-containing compounds had better anti-NMDA activity.
Arctium lappa, commonly known as burdock, is being promoted as a healthy and nutritive food in Chinese societies. This study investigated the roots, seeds, and leaves of burdock in view of its popular uses in traditional Chinese medicine. Seven compounds, including three new ones, were isolated from the seeds of Arctium lappa. Structures of these compounds were examined by conducting extensive spectroscopic analysis. Biological analysis showed that compounds 4, 5, 6, and 7 could inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells, and the IC50 values were in the range of 14.7–18.3 μM.
The Himalyan region harbors rich diversity of medicinal plants which
are used as traditional medicines for a variety of diseases and
complications (Kala 2005). The people in the Himalayan region have
mastered and exercised the usage of medicinal plants which they used to
grow in their close vicinity for treating various ailments through trial and
error. The cherished ancient knowledge usually been propagated through
the oral message, requires to be documented imperatively. During the last
half a century, only few studies have been carried out to document the
medicinal properties of the plant species that grows in the region, particularly
in the remote and difficult terrains. Kashmir Himalaya often referred to
as Terrestrial Paradise on Earth, is located at the Northwestern tip of the
Himalayan biodiversity hotspot. The valley has rich biodiversity of plants
and majority of these plants have medicinal properties that have been used
in traditional health care systems for thousands of years (Malik, Khuroo
et al. 2011). This knowledge of using medicinal plants as traditional
medicine, transmitted by oral tradition from generation to generation, has
been eroding in recent decades due to rapid cultural and developmental
change. At present a significant percentage of people of J&K especially
tribal and nomads (Gujjars and Bakerwals) are wholly and solely dependent
on traditional medicines as far as their heath issues are concerned (Rashid
2012). Apart from this, important medicinal plants are being overexploited
at an alarming rate (Baig, Ramamoorthy et al. 2013).
Dormancy is a complex phenomenon that allows plants to survive the winter season. Studies of dormancy have recently attracted more attention due to the expansion of temperate fruit production in areas under mild winters and due to climate changes. This study aimed to identify and characterize the metabolic changes induced by chilling temperatures, as well as during thermal fluctuation conditions that simulate mild winter and/or climate change scenarios. To do this, we compared the metabolic profile of Japanese pear flower buds exposed to constant chilling at 6 °C and thermal fluctuations of 6 °C/18 °C (150 h/150 h) during endodormancy. We detected 91 metabolites by gas chromatography paired with time-of-flight mass spectrometry (GC-TOF-MS) that could be classified into eight groups: amino acids, amino acid derivatives, organic acids, sugars and polyols, fatty acids and sterols, phenol lipids, phenylpropanoids, and other compounds. Metabolomics analysis revealed that the level of several amino acids decreased during endodormancy. Sugar and polyol levels increased during endodormancy during constant chilling and might be associated with chilling stress tolerance and providing an energy supply for resuming growth. In contrast, thermal fluctuations produced low levels of metabolites related to the pentose phosphate pathway, energy production, and tricarboxylic acid (TCA) cycle in flower buds, which may be associated with failed endodormancy release. This metabolic profile contributes to our understanding of the biological mechanism of dormancy during chilling accumulation and clarifies the metabolic changes during mild winters and future climate change scenarios.
Łopian (Arctium lappa L.) to popularna roślina uważana za chwast w naszej strefie klimatycznej, podczas gdy w krajach Azji Wschodniej, łopian jest uprawiany jako warzywo (korzeń) i roślina lecznicza. W ostatnich latach, łopian był szeroko badany pod kątem składników aktywnych zawartych w korzeniu, liściach i nasionach, oraz ich właściwości fizykochemicznych i biochemicznych. Badania te potwierdzają przeciwrodnikowe, przeciwutleniające i antybakteryjne działanie surowców z łopianu. Z praktycznego punktu widzenia, nieobrany korzeń łopianu, który nie został poddany obróbce cieplnej najlepiej nadaje się do wytwarzania surowców kosmetycznych. Ekstrakty z łopianu charakteryzują się zdolnością hamowania wzrostu niektórych drobnoustrojów (m. in. endodontycznych) więc mogą one być stosowane w mydłach antybakteryjnych i pastach do zębów. Chociaż surowce kosmetyczne z korzeni, nasion, owoców lub liści łopianu wykazują właściwości istotne przy projektowaniu kosmetyków oraz są dostępne na rynku, nadal są rzadko stosowane w kosmetykach.
Chlorogenic acid is a well-known antioxidative compound. We investigated the content and behavior of chlorogenic acid derivatives with DPPH radical scavenging activity in sweet potato prepared by various cooking methods. A significant correlation was obtained between the chlorogenic acid content and DPPH radical scavenging activity. While the content and activity in sweet potato cooked with water were substantially retained, roasting in a convection oven resulted in their lower retention due to the higher temperature of around 200°C. We propose that chlorogenic acid could be effectively taken in sweet potato when cooked in a microwave oven or steamed, and also simmered with the cooking water after boiling.
This chapter gives a relatively comprehensive introduction about chlorogenic acids from sweet potato. It starts by presenting a well-rounded overview on chlorogenic acids. It then presents the preparing technology of chlorogenic acids from sweet potato, including pretreatment, extraction, purification, and qualitative and quantitative analyses. Next, the biological activities of chlorogenic acids from sweet potato are introduced and followed by the effects of pH, heat, and light treatments on the total polyphenol content and antioxidant activities of chlorogenic acids from sweet potato. By the end of this chapter, the applications of chlorogenic acids from sweet potato in different products are introduced.
Scope:
Chicory (Cichorium intybus L.) is a perennial herb often consumed as a vegetable, whereas the ground and roasted roots are blended as a coffee substitute. Caffeoylquinic or chlorogenic acids (CQA), the abundant intermediates of lignin biosynthesis in chicory, have been reported to improve glucose metabolism in humans, but the functional group in their structure responsible for this effect has not been yet characterized.
Methods and results:
Here, we showed that three di-O-caffeoylquinic acids suppressed hepatic glucose production in H4IIE rat hepatoma cells by reducing expression of glucose-6-phosphatase (G6Pase) and phosphoenolpyruvate carboxykinase (PEPCK), two key enzymes that regulate hepatic gluconeogenesis. Direct comparisons between CQAs and their metabolites (3-caffeoylquinic, caffeic, and quinic acids) revealed the caffeic acid moiety alone was responsible for the observed effects. Further analysis suggested the activation of PI3K and MAPK pathways as a method of controlling gene expression was shared between caffeoylquinic and caffeic acids. These compounds promoted increased mitochondrial respiration and cellular metabolism, in part by inducing oxidative phosphorylation and proton leak.
Conclusions:
We concluded that the caffeic acid moiety was important for suppression of hepatic gluconeogenesis and hyperglycemia, ultimately strengthening the link between dietary interventions based on caffeic acid-containing plant foods and healthy glucose metabolism. This article is protected by copyright. All rights reserved.
The study investigated the quality characteristics of white castella prepared with 0, 10, 20, and 30% burdock (Arctium lappa L.) powder. The specific gravity and weight of castella increased with higher burdock powder content. Height and baking loss rate of castella were not significantly different among the samples. The pH of castella decreased with increasing burdock powder content, whereas ^{\circ}Brix of castella increased. Hunter L and b values of crust increased, whereas a values decreased with addition of burdock powder. Hunter L values of crumb decreased, whereas a and b values of crumb increased. The hardness of castella increased upon addition of burdock powder, whereas fracturability, springiness, cohesiveness, gumminess, and resilience decreased. DPPH radical scavenging activity and total polyphenol contents increased significantly upon addition of burdock powder (P
The antioxidative activity of a 70% methanol extract of sweet potatoes was estimated in a linoleic acid-aqueous system. The extract had a markedly strong antioxidative activity. Major phenolic components contained in the 70% methanol extract were identified as chlorogenic acid and isochlorogenic acid-1, -2 and -3 by using high-performance liquid chromatography. The other minor free phenolics were identified, or tentatively identified, as caffeic acid and 4-o-caffeoylquinic acid. Chlorogenic acid and/or isochlorogenic acids, however, had only slight antioxidative activity. From the results of the addition of chlorogenic acid, isochlorogenic acids and the other coexisting components contained in the sweet potato extract, the effective antioxidant activity of the sweet potato extract was proposed to be mainly based on the synergistic effect of phenolic compounds with amino acids.
Chromatography on Florisil® (activated magnesium silicate) was used to separate model compounds representative of hydrocarbons, cholesterol esters, triglycerides, free sterols, diglycerides, monoglycerides, and free fatty acids. The order of elution was the same as that observed in silicic-acid chromatography except that free fatty acids were eluted after monoglycerides. Recoveries were nearly quantitative and the positions of individual compounds on the chromatograms were highly reproducible. Phospholipids were not eluted under the conditions used for separating the above compounds, and were eluted less readily from Florisil than from silicic acid with methanol. Florisil had definite advantages over silicic acid for the separation of lipid classes by column chromatography. It required no prewashing or other pretreatment except deactivation with water. Columns were quickly and easily packed, and the relatively coarse mesh of the Florisil permitted rapid flow rates. Separations could be achieved in much shorter times with smaller volumes of eluting solvents. Preliminary experiments indicated that chromatography on Florisil gave good separations of lipid classes of naturally occurring lipids extracted from liver and blood.
Two new guaianolides combined with a sulfur-containing acetylenic compound were isolated from Arctium lappa (Compositae). Their structures were elucidated on the basis of spectral data.
リノール酸の自動酸化物がβ-カロチンを退色させることを利用し,その退色の防止活性を指標とした抗酸化性の測定法を用いて, 43種の野菜の80%メタノール抽出液の抗酸化活性を測定し,以下の結果を得た.(1) BHAの抗酸化活性と比較し検討したところ,シュンギクやショウガ,アスパラガス等13種は, BHAが生鮮重100g当たり25mg以上含有されていることに相当する程の活性を示すことが分かった. BHA 5mg/100g以下に相当するものは,カボチャやキウリ,カブ,キャベツ等13種であった.(2) 野菜抽出液のポリフェノール含量と抗酸化性の相関性を検討したところ, 43種の野菜でr=0.7694となり,相関性があることを明らかにした.(3) 比較的抗酸化性の強い3種の野菜の抗酸化性成分をHPLCで分取し,質量分析計等で解析したところ,アスパラガスではルチン,ショウガではヘキサヒドロクルクミンとジンジェロールが同定された.一方シュンギクでは, 3, 5-ジカフェオイルキナ酸および新規のジカフェオイルキナ酸誘導体と推定される成分が得られた.
Two-dimensional heteronuclear chemical-shift correlation (1-4) has proven to be a very effective way for identifying which proton is bonded to which 13C nucleus. Unfortunately, the experiment is much less effective in determining long-range con-nectivity (5), i.e., correlating shifts from protons and 13C nuclei that are separated by two or more bonds. A possible way for determining two-bond connectivity is the two-dimensional RELAY experiment (6-9). Although this experiment is considerably less sensitive than conventional heteronuclear chemical-shift correlation, it can provide very useful information. In practice, there is a great interest in determining three-bond 'H-13C connectivity, as this would allow "bridging" of nonprotonated carbons, and nuclei other than carbon, for example, oxygen and nitrogen. In most practical cases, none of the tech-niques mentioned above are very effective at doing this. It will be demonstrated here, that a modified version of the refocused INEPT experiment (10-12) is a very sensitive and simple way for determining two-and three-bond connectivity. It has been dem-onstrated elsewhere that this modified INEPT experiment is also very useful for enhancing sensitivity of nonprotonated "N nuclei (13). For a description of how the regular INEPT experiment functions, the reader is referred to the original literature (10-12). Here the effect of replacing all nonselective proton pulses in the INEPT experiment by "soft" pulses (YH, = 25 Hz) will be discussed. The pulse scheme is sketched in Fig. 1. As will be shown below, the effect of this sequence can easily be understood. The first soft 90: proton pulse rotates the magnetization of one preselected proton into a position parallel to the y axis of the rotating frame (Fig. 2a). Consider the case where there is a 13C nucleus in the molecule that has a long-range coupling, irJcH, with the proton considered. The proton mag-netization will then evolve during the first half of the delay A,, under the influence of chemical shift, static magnetic field inhomogeneity, homonuclear J coupling, and coupling with the i3C nucleus (Fig. 2b). For clarity, the 'rJcH interaction is assumed to be larger than the homonuclear proton-proton coupling in the diagram. The selective 180; proton pulse then rotates the proton magnetization vectors 180" about the y axis (Fig. 2c) and all the effects of 'H-'H and 'H-13C J coupling, static field inhomogeneity, and chemical shift would refocus at the end of the interval, A1.
Six hydrolysable tannins, casuarinin (1), casuariin (2), punicacortein A (3), degalloyl-punicacortein A (4), 2,3-[(S)-4,4′,5,5′,6,6′-hexahydroxydiphenoyl]-d-glucopyranoside (5), and 4,6-[(S)-4,4′,5,5′,6,6′-hexahydroxydiphenoyl]-d-glucopyranoside (6), and related compounds, gallic acid, methyl gallate and ellagic acid, were isolated from the methanol extract of Osbeckia chinensis. In order to confirm the structure-activity relationship, the antioxidant activities of these compounds were examined both in the food model and in vitro systems. The antioxidative efficiency, using the thiocyanate and TBA methods, increased in the order of gallic acid <α-tocopherol<methyl gallate<(4)<(3)<(5)=(6)<(2)<(1)=BHA<ellagic acid. The in vitro antioxidant order is α-tocopherol<gallic acid<methyl gallate<(4)<(3)=(5)=(6)=ellagic acid<(2)<(1) in the rabbit erythrocyte membrane ghost system, and ellagic acid <(4)<gallic acid<(3)=(5)=(6)<methyl gallate<(2)<(1) = α-tocopherol in the rat liver microsome system.
Assay-guided isolation gave three new compounds, cassumunins A, B, and C, having both antioxidant and antiinflammatory activities, from the rhizomes of a tropical ginger, Zingiber cassumunar. Antioxidant activity and antiinflammatory activity were measured using a thiocyanate method and a 12-O-tetradecanoylphorbol 13-acetate-induced method on mouse ear, respectively. The antioxidant activity of cassumunins A-C is stronger than that of curcumin, and their antiinflammatory activity is also stronger than that of curcumin. Spectroscopic analysis of cassumunins A-C revealed them to be a new type of complex curcumin. Antioxidant and antiinflammatory activities of cassumunins suggested that the substituted group at the 5'-position of curcumin increased both activities.
The antioxidant activity of N-(long-chain-acyl)histidine-containing compounds was investigated. In a homogeneous solution of methyl linoleate with a radical initiator, these compounds suppressed the production of methyl linoleate hydroperoxides. When the oxidation of phosphatidylcoline liposomes was induced by ferrous ion and ascorbic acid, N-(long-chain-acyl)histidine and N-(long-chain-acyl)carnosine could suppress the oxidation more efficiently than histidine and carnosine. The emulsifying activities of these compounds were found to be higher than those of conventional surfactants, that is, casein, Tween 80, and Triton X-100.
Administration of eriodyctiol and (+)-catechin ( of body weight) to mice inhibited the enhancement of in situ liver chemiluminescence produced by CCl4 () by 32 and 38% respectively. 3,4-Dicaffeoylquinic acid was less effective (13%), and cynarin had no effect. Previously, these compounds and other polyphenols were assayed as in vitro antioxidants by their abilities to inhibit the tert-butyl hydroperoxide (t-BOOH)-initiated chemiluminescence of mouse liver homogenates, and the IC50 (μM) values were as follows: ( + )-catechin, 3; eriodyctiol, 9; myricetin and 4,2′,4′-trihydroxy-6′-metoxychalcone, 15; 3,4-dicaffeoylquinic acid, 20; isochlorogenic acid, 30; caffeic acid, 5,6,3′-trihydroxy-7,4′-dimethoxyflavone and cynarin, 50; chlorogenic acid and apigenin, 150; quercetin, pedalitin, sylimarin and quercetin-3-methyl ester, 200; 7,4'-dihydroxy-5-methoxyflavonone and kaempferol-3,7-dirhamnoside, 500; quercitrin, 900; and galangin-3-methyl ether, genkwanin, hesperidin, ombuoside, phloridzin, quinic acid, rhoifolin, rutin and sophoricoside, greater than 1 mM. The in vitro and in vivo effects of these flavonoids and polyphenols may be related to their antioxidant abilities, making them promising substances to be investigated as water-soluble protectors against lipid peroxidation and other free radical-mediated cell injury.
Two caffeoylquinic acids were isolated from flowers of Arnica montana and three from A. chamissonis ssp. foliosa var. incana. Their structures were established on the basis of spectral data (UV, 1H NMR, 13C NMR, FABMS) as 1,4,5-tri-O-caffeoylquinic acid, 1,5-di-O-caffeoylquinic acid and 3,4,5-tri-O-caffeoylquinic acid methyl ester. The first compound is a new natural product.
The hepatoprotective activity against CCl4 toxicity in isolated rat hepatocytes of some polyphenolic compounds, such as cynarin, isochlorogenic acid, chlorogenic acid, luteolin-7-glucoside, and two organic acids, caffeic and quinic, from Cynara scolymus, is tested. Only cynarine and, to a lesser extent, caffeic acid showed cytoprotective action. The possible relationship between the molecular structure and the protective effect found is discussed.
Agata, I.; Arichi, S. Studies on the activities of tannins and related com-pounds
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Studies on the tannin of fiuits and vegetables. Part 111. Polyphenolic compounds and phenol oxidative enzyme of edible burdock. Nippon Shokuhin Kogyo Gakkai-shi
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Nakabayashi, T. Studies on the tannin of fiuits and vegetables. Part 111. Polyphenolic compounds and phenol oxidative enzyme of edible burdock. Nippon Shokuhin Kogyo Gakkai-shi 1968,15, 199-206.
Tzoutzu-lova, A.; Apostolova, B.; Kuleva, L. Triterpenoids and sterols from roots ofArctium lappa
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Yochkova, Y. I.; Mladenova, K. A.; Zaharieva, E. V.; Tzoutzu-lova, A.; Apostolova, B.; Kuleva, L. Triterpenoids and sterols from roots ofArctium lappa. Dokl. Bolg. Akad. Nauk 1990,