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Изучены особенности накопления флавоноидов в органах надземной части растений Rheum compactum L. методом высокоэффективной жидкостной хроматографии. В этанольных экстрактах из репродуктивных органов, стеблей и листьев R. сompactum идентифицированы флавонолы кверцетин, кемпферол, рамнетин, рутин, астрагалин и флавон лютеолин. Выявлено, что флавонолы кверцетин, кемпферол, рамнетин, рутин и астрагалин содержатся во всех органах. Экстракт из плодов отличается наличием флавона лютеолина. Бутоны (13,06%), соцветия (6,92%) и листья в фазах вегетации (5,28%) и бутонизации (6,23%) могут быть источником рутина. Меньше всего рутина в черешках листьев (0,16–0,40%). Содержание остальных идентифицированных фенольных соединений в экстрактах из надземных органов R. сompactum не достигает 1%. Более высокое содержание кверцетина в соцветиях (0,55%) и бутонах (0,22%), кемпферола и астрагалина – в бутонах (0,19 и 0,44%, соответственно) и в листьях в фазе вегетации (0,14 и 0,26%), а рамнетина – в листьях в фазе вегетации (0,24%) и в бутонах (0,15%). В черешках листьев содержится меньше флавоноидов, чем в листьях и репродуктивных органах., Features of the flavonoids accumulation in the organs of aboveground parts of the plants Rheum compactum L. was investigated by High-Performance Liquid Chromatography method. The flavonols quercetin, kaempferol, rhamnetin, rutin, astragalin and flavone luteolin identified in the ethanol extract of the reproductive organs, stems and leaves of R. compactum.It was revealed, that the flavonols quercetin, kaempferol rhamnetin, rutin, astragalin contain in all the organs. The extract from the fruit is different by the presence of flavone luteolin. Buds (13,06%), inflorescence (6,92%) and leaves in the phases of vegetation (5,28%) and budding (6,23 %) may be a source of rutine. Least of all rutin accumulates in the petioles (0,16–0,40%).The content of the other phenolic compounds identified in the extracts from the aboveground organs R. compactum less than 1%. The higher content of quercetin in the inflorescences (0,55%) and buds (0,22%), astragalin and kaempferol – in the buds (0,19 and 0,44%, respectively) and in the leaves in the phases of vegetation (0,14 and 0,26%), and rhamnetin – in the leaves in the phases of vegetation (0,24%) and buds (0,15%). The petioles contain less flavonoids than in the leaves and reproductive organs.

The chemical investigation of ethanolic extract from rhizomes of Cautleya spicata (Sm.) Baker (Zingiberaceae) has resulted in the isolation of eight compounds which were characterised as β-sitosterol (1), β-sitosterol β-D-glucoside (2), bergapten (3), zerumin A (4), (E)-labda-8(17),12-diene-15,16-dial (5), kaempferol (6), quercetin (7) and astragalin (8). All compounds were identified by spectroscopic and chemical methods. This paper describes the first phytochemical work on C. spicata.

Four different colored beans (white, red, pinto, and black beans) were investigated for factors affecting iron bioavailability using an in vitro digestion/human Caco-2 cell model. Iron bioavailability from whole beans, dehulled beans, and their hulls was determined. The results show that white beans contained higher levels of bioavailable iron compared to red, pinto, and black beans. These differences in bioavailable iron were not due to bean-iron and bean-phytate concentrations. Flavonoids in the colored bean hulls were found to be contributing to the low bioavailability of iron in the non-white colored beans. White bean hulls contained no detectable flavonoids but did contain an unknown factor that may promote iron bioavailability. The flavonoids, kaempferol and astragalin (kaempferol-3-O-glucoside), were identified in red and pinto bean hulls via HPLC and MS. Some unidentified anthocyanins were also detected in the black bean hulls but not in the other colored bean hulls. Kaempferol, but not astragalin, was shown to inhibit iron bioavailability. Treating in vitro bean digests with 40, 100, 200, 300, 400, 500, and 1000 microM kaempferol significantly inhibited iron bioavailability (e.g., 15.5% at 40 microM and 62.8% at 1000 microM) in a concentration-dependent fashion. Thus, seed coat kaempferol was identified as a potent inhibitory factor affecting iron bioavailability in the red and pinto beans studied. Results comparing the inhibitory effects of kaempferol, quercitrin, and astragalin on iron bioavailability suggest that the 3',4'-dihydroxy group on the B-ring in flavonoids contributes to the lower iron bioavailability.

The functional components of leaves and their shoots classified into four categories according to length were investigated using Japanese persimmon 'Saijo'. The obtained results are as follows : (1) The total ascorbic acid (T-AsA) content in leaves from long (60-80cm) shoots (5, 310mg/100g DW) was about 1.4-fold that in foliating leaves (F-leaves). The highest T-AsA content (4, 690mg/100g DW) was obtained in medium (40-60cm) shoots (M-shoots). (2) The isoquercitrin contents in leaves were 240-360mg/100g DW and the astragalin content was 200-270mg/100g DW. The isoquercitrin and astragalin contents in shoots were significantly lower than those in leaves. (3) The polyphenol as catechin contents in shoots (5, 100-6, 200mg/100g DW) were lower than those in leaves (6, 000-9, 200 mg/100g DW). The polyphenol content of F-leaves was the highest (9, 200mg/100g DW) and decreased with an increase in the length of donor shoots. The polyphenol content of M-shoots was the highest (6, 200mg/100g DW) among the four shoot categories. In this study, we conclude that shoots as well as leaves are suitable material for health foods as sources of T-AsA, and that F-leaves are suitable sources of functional compounds (Polyphenols).

A prenylated arylbenzofuran and six flavonoids were isolated from the fruits of Morus alba L. through silica gel, octadecyl silica gel, and Diaion HP-20 column chromatography. Based on the nuclear magnetic resonance, mass spectrometry, and infrared spectroscopic data, the chemical structures of the compounds were determined to be artoindonesianin O (1), isobavachalcone (2), morachalcone A (3), quercetin (4), astragalin (5), isoquercetin (6), and rutin (7). The isolated compounds were evaluated for protection of HT22-immortalized hippocampal cells against glutamate-induced oxidative stress. Compounds 1 and 3 exhibited protective effects with EC50 values of 19.7±1.2 and 35.5±2.1 μM, respectively. The major compounds 1-3 and 7 were quantified using liquid chromatography/mass spectrometry analysis and were determined to be 1.88±2.1, 1.90±1.8, 0.78±1.5, and 37.29±2.2 mg/kg, respectively, in the ethanol extract of M. alba L. fruits.

We isolated four flavonols from garlic (Allium sativum L) leaf and shoot and measured the in vitro antioxidant activity of the isolated flavonols and their aglycones. The chemical structures of the compounds were shown to be quercetin 3-O-β-D-glucopyranoside (isoquercitrin), quercetin 3-O-β-D-xylopyranoside (reynoutrin), kaempferol 3-O-β-D-glucopyranoside (astragalin) and isorhamnetin 3-O-β-D-glucopyranoside based on FAB-MS and NMR analyses. Assays of DPPH (1,1-diphenyl-β-picryl hydrazyl) and hydroxyl radical scavenging, inhibition of linoleic acid peroxidation, and soybean lipoxygenase (LO) and hyaluronidase (HYA) inhibition were used to evaluate the antioxidant activity. Quercetin and its glycosides showed the highest antioxidant activity among the compounds. In the LO assay, the IC50 values of quercetin, isoquercitrin and reynoutrin were 16.9, 40.1 and 32.9 µM respectively. Quercetin was the most effective among the flavonols. In the HYA assay the IC50 values of quercetin, isoquercitrin and reynoutrin were 23.0, 20.9 and 22.1 mM respectively. Isoquercitrin had the most potent inhibitory activity on HYA. The inhibition patterns of the flavonols on LO and HYA were elucidated as mixed types of competitive and non-competitive inhibition according to Lineweaver–Burk plot results. Although most garlic shoots and leaves are discarded and not used at present, our results suggest that ancillary garlic parts could be utilised as functional foods or ingredients. Copyright © 2004 Society of Chemical Industry

Phenolic compounds are the major bioactive constituents of the Chinese herbal drug Tu-Si-Zi, which is prepared from the seeds of Cuscuta chinensis. However, seeds of C. australis also are offered under the name of this drug in the herb market. In order to make a comparison of their chemical constituents, the phenolic compounds of these two Cuscuta species were analyzed by high-performance liquid chromatography/diode-array detection/electrospray ion trap tandem mass spectrometry (HPLC/DAD/ESI-MS(n)). A total of 50 compounds were observed in the methanol extracts, including 23 flavonoids, 20 lignans and 7 quinic acid derivatives. These compounds were separated on a C18 column and identified or tentatively characterized based on UV spectra and MS fragmentation behavior. In contrast to previous reports, the phenolic patterns of these two Cuscuta species were found to be very different. Kaempferol and astragalin were the predominant constituents of C. australis, while hyperoside was the major compound in C. chinensis. Most of the identified compounds, especially the acylated flavonoid glycosides, have not previously been reported from Cuscuta species. In addition, a 30 Da neutral loss observed for flavonols was investigated and could be used to differentiate flavonoid isomers such as kaempferol and luteolin. The ESI-MS fragmentation behavior of furofuran lignans was also investigated, and a characteristic pathway is proposed. The large differences observed between the phenolic constituents of C. chinensis and C. australis strongly encouraged further comparison of the bioactivities of these two species.

The known flavonoids pinostrobin (5-hydroxy-7-methoxyflavanone), 2',6'-dihydroxy-4',5'-dimethoxychalcone (polygochalcone), astragalin, isoquercitrin, quercitrin, and also the new natural compound 6'-hydroxy2',4'-dimethoxychalcone (persicochalcone) were isolated from the aerial part of lady’s thumb (Polygonum persicaria L.) and characterized using PMR and UV spectroscopy and mass spectrometry.

Phytochemical investigation of Litsea fruticosa (Hemsl.) Gamble resulted in the isolation of eight flavonoids and four alkaloids. Their structures were identified as pinostrobin, pinocembrin, pinocembrin chalcone, apigenin, kaempferol, astragalin, isoquercetin, kaempferol 3,4′-di-O- l -rhamnopyranoside, boldine, laurolitsine, actinodaphnine and ushinsunine by comparison of their spectral data with those reported previously in the literature. Chemotaxonomic significance of these investigation is summarized.

Moringa oleifera Lam. (Moringaceae) possesses therapeutic potential for pharmaceutical product development. However, reports on chemical and biological stabilities of the bioactive components in the leaf extracts of M. oleifera are limited. This investigation aimed to evaluate the stability of bioactive compounds and free radical scavenging abilities of the leaf extracts stored under different conditions as established in the ASEAN guideline on drug stability study. The quantitative analysis of three major anti-oxidative constituents, crypto-chlorogenic acid, isoquercetin and astragalin, were performed using high-performance liquid chromatography. Total phenolics and total flavonoids contents, and DPPH free radical scavenging activity of the stored extracts were also investigated. After six months of storage, the bioactive contents and free radical scavenging activity of the extract kept at 25 ± 2 °C with 60 ± 5% relative humidity (RH) slightly decreased. About 50% decrease on the contents of active compounds and scavenging activity were found in the extract kept under accelerated condition at 40 ± 2 °C with 75 ± 5% RH. High temperature and humidity negatively impacted the contents of bioactive constituents and free radical scavenging activity of the extracts. Thus, the extracts and product from M. oleifera leaves should be kept in a cold place to prevent significant changes in chemical, physical and biological properties.

The methanol extract obtained from the aerial parts of Aceriphyllum rossii (Saxifragaceae) was fractionated into ethyl acetate (EtOAc), n-BuOH and H2O layers through solvent fractionation. Repeated silica gel column chromatography of EtOAc and n-BuOH layers afforded six flavonol glycosides. They were identified as kaempferol 3-O-beta-D-glucopyranoside (astragalin, 1), quercetin 3-O-beta-D-glucopyranoside (isoquercitrin, 2), kaempferol 3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (3), quercetin 3-O-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside (rutin, 4), kaempferol 3-O-[alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside] (5) and quercetin 3-O-[alpha-L-rhamnopyranosyl (1-->4)-alpha-L-rhamnopyranosyl (1-->6)-beta-D-glucopyranoside] (6) on the basis of several spectral data. The antioxidant activity of the six compounds was investigated using two free radicals such as the ABTS free radical and superoxide anion radical. Compound 1 exhibited the highest antioxidant activity in the ABTS [2,2-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid)] radical scavenging method. 100 mg/L of compound 1 was equivalent to 72.1+/-1.4 mg/L of vitamin C, and those of compounds 3 and 5 were equivalent to 62.7+/-0.5 mg/L and 54.3+/-1.3 mg/L of vitamin C, respectively. And in the superoxide anion radical scavenging method, compound 5 exhibited the highest activity with an IC50 value of 17.6+/-0.3 microM. In addition, some physical and spectral data of the flavonoids were confirmed.

The influence of traditional Chinese medicine (TCM) formulation from Astragalus Root (Radix astragalin seu Hedysari) and Chinese Angelica Root (R. Angelicae Sinensis) at a ratio of 5:1 (w/w) on non-specific immunity of Jian carp, Cyprinus carpio var. Jian was investigated. The number of NBT-positive cells in the blood and lysozyme and complement activities in the serum of Carp fed with commercial feed supplemented with 1.0% (diet 1) and 1.5% (diet 2) TCM at 10 day of post-feeding were not different from those of the control group fed with feed unsupplemented TCM 10 days post-feeding (P0.05), but at 20 and 30 days they increased significantly (P0.05). The values of diet 1 group and diet 2 group at 20 day and at 30 day were not significantly different (P0.05) from each other. In addition, the TCM formula increased body weight of experimental fish by about 16.84% (diet 1) and 19% (diet 2) above that of the control group. Therefore, these data suggest that the TCM formula could elevate the function of non-specific immunity of Jian carp. The optimal dosage added to commercial carp feed was 1.0% (w/w) and the oral administration time as a course of treatment was 20 days.

The kinetics of catalase decomposition of H2O2 (50 mM) inhibited by the flavonolic glycoside astragalin (1) from the aerial part of Gymnocarpium dryopteris were studied. 1 (0.3-30 M) is a strong inhibitor of the catalase process and was tested as a catalase (CAT) protector from ultrasonic activation at 45°C by treatment of enzyme solutions (1.2 nM) in phosphate buffer (7.5 mM) at pH 5.5 with low-frequency ultrasound (US, 27 kHz) at initial specific power 60 W/cm2. 1 inhibited US-inactivation of CAT according to the rate constants for US-inactivation of CAT in the presence of 1 with and without inhibitor. 1 at concentrations of 1.0 and 20.0 μM decreases US-inactivation up to 22.3 and 19.5% of the initial level. The useful properties and effectiveness of 1 are better than the synthetic inhibitors-antioxidants propylgallate and 4-t-butylpyrocatechin.

Four new jatrophane diterpenoids, altotibetin A (1), altotibetin B (2), altotibetin C (3), altotibetin D (4), and nine known compounds, beta-sitosterol, cycloart-23-ene-3beta,25-diol, cycloart-25-ene-3beta,24-diol, lupeol acetate, scopoletin, kaempferol, uracil, uridine, astragalin, and daucosterol have been isolated from the whole plant of Euphorbia altotibetic PAULS. Their structures were established by spectral methods, and the configurations of 1 and 2 were confirmed by X-ray analysis.

The influence of traditional Chinese medicine (TCM) formulated from Astragalus Root (Radix astragalin seu Hedysari) and Chinese Angelica Root (Radix angelicae sinensis) at the rate of 5:1 (w/w) on nonspecific immunity including the number of phagocytes, lysozyme and complement activities, and disease resistance to Vibrio alginolyticus in large yellow croaker, Pseudosciaena crocea (Richardson) was determined. Minced fish (surimi) supplemented with 0.5% TCM had no influence on the nonspecific immunity of the fish (P>0.05). On the other hand, the surimi with 1.0% and 1.5% TCM resulted in a significant increase in nitroblue tetrazolium (NBT) positive cells and lysozyme activities (P

Chaya (Cnidoscolus chayamansa, McVaugh) is an ubiquitous plant in southern Mexico. Its high nutritional value is well documented but its content of toxic cyanide glycosides and medicinal metabolites are undetermined. The concentrations of HCN and derivatives from chaya leaves were measured in the range of 2.37-4.25 mg/100 of dry weight. Several thermal treatments were tested to eliminate these undesirable components. Five minutes in boiling water was enough to destroy any residualcyanide. This pretreatment is recommended for safe consumption of the leaves. Some of the medicinal properties attributed to chaya may be due to the four flavonoids isolated from the aerial parts of this plant. Dihydromyricetin was isolated from the bark while the leaves had the biflavonoid (3′→ 8)-diapigenin (amentoflavone) and the glycosides kaempferol-3-O-glucoside (astragalin) and kaempferol-3-O-rutinoside.

Preparative RP-HPLC analysis of a methanol extract of the seeds of Rosa canina yielded kaempferol 3- O -(6?- O-E-p -coumaroyl)-s-D-glucopyranoside and kaempferol 3- O -(6?- O-Z-p -coumaroyl)-s-D-glucopyranoside. Structures of these compounds were elucidated by comprehensive spectroscopic analyses. Bioactivity, i.e., antibacterial and antioxidant activity and general toxicity, of these compounds were also determined.

The flavonoid glycosides kaempferol-​3-​O-​β-​D-​glucopyranoside (astragalin)​, kaempferol-​3-​O-​rutinoside and kaempferol-​3-​O-​(2-​gal-​rhamnosyl-​robinobioside) (mauritianin) as well as the aglycons apigenin, kaempferol and quercetin were isolated from the cell suspension cultures of Astragalus sieberi DC. (Leguminosae)​. The isolated compds. were detected by TLC and HPLC in varying amts. and identified by spectral anal. and comparison with authentic samples

Moringa oleifera , usually called “wonderful tree”, has been scientifically proven to inhibit proliferation of many cancer cell types by induction of apoptosis. Apoptosis is an energy dependent process, whereby cells due for death as a result of abnormal gene mutation, ageing among others commit suicide. It is referred to as hallmark of cancer. Proliferation of cancer cells is not unconnected to deficiency in their apoptotic process such as loss of caspase activity, p53 gene mutation and imbalanced regulation of Bcl2 proteins which leads to inactivation or reduction in cancer cell apoptosis, hence, agents that are capable of inducing apoptosis in cancer cells are potential sources of effective anticancer drug. The ability of M. oleifera to trigger apoptosis in cancer cells largely depends on its phytochemicals, most especially antioxidant phenols such as gallic acid, chlorogenic acid, rutin, apigenin, astragalin, quercetin, and kampferol. These compounds act by activating pro-apoptotic protein such as caspases, TRAIL, bax, bad, and inhibiting activity of anti-apoptotic proteins like Bcl2, IAPs (inhibitor of apoptosis), FLIP. In this review, we discussed cell apoptosis and its pathways, dysregulation of apoptosis in cancer cells, and more importantly, induction of apoptosis in cancer cells by Moringa oleifera tree. Keywords: Apoptosis, cancer cells, Moringa oleifera

The aim of this study was to explore the role of p-coumaroyl in the antioxidant and cytoprotective effects of flavonoid glycosides. The antioxidant effects of astragalin and tiliroside were compared using ferric ion reducing antioxidant power, DPPH• scavenging, ABTS•+ scavenging, •O2– scavenging, and Fe2+-chelating assays. The results of these assays revealed that astragalin and tiliroside both exhibited dose-dependent activities; however, tiliroside exhibited lower IC50 values than astragalin. In the Fe2+-chelating assay, tiliroside gave a larger shoulder-peak at 510 nm than astragalin, and was also found to be darker in color. Both of these compounds were subsequently evaluated in a Fenton-induced mesenchymal stem cell (MSC) damaged assay, where tiliroside performed more effectively as a cytoprotective agent than astragalin. Tiliroside bearing a 6′′-O-p-coumaroyl moiety exhibits higher antioxidant and cytoprotective effects than astragalin. The 6′′-O-p-coumaroyl moiety of tiliroside not only enhances the possibility of electron-transfer and hydrogen-atom-transfer-based multi-pathways, but also enhances the likelihood of Fe-chelating. The p-coumaroylation of the 6"-OH position could therefore be regarded as a potential approach for improving the antioxidant and cytoprotective effects of flavonoid glycosides in MSC implantation therapy.

Background: Chiranthodendron pentadactylon Larreat. (Sterculiaceae) is a Mexican plant used in traditional medicine for the treatment of heart disease symptoms and infectious diarrhea. Objective: To evaluate in vitro antiprotozoal and antibacterial activities and in vivo antidiarrheal activity from the flowers of C. pentadactylon using the extract, fractions, and major isolated flavonoids. Materials and methods: Bioassay-guided fractionation of the methanol extract of C. pentadactylon (MECP) led to the isolation of five flavonoids, tiliroside, astragalin, isoquercitrin, (+)-catechin, and (-)-epicatechin. Antimicrobial activities were tested on two protozoa (Entamoeba histolytica and Giardia lamblia) and nine bacterial enteropathogens (two Escherichia coli strains, two Shigella sonnei strains, two Shigella flexneri strains, two Salmonella sp. strains, and Vibrio cholerae) isolated from feces of children with acute diarrhea or dysentery and resistant to chloramphenicol. Also, antidiarrheal activity was tested on cholera toxin-induced diarrhea in male Balb-c mice. Results: Epicatechin was the most potent antiamoebic and antigiardial compound with IC50 values of 1.9 μg/mL for E. histolytica and 1.6 μg/mL for G. lamblia; tiliroside showed moderate antiprotozoal activity against both protozoan. In contrast, in the antibacterial activity, tiliroside was the most potent compound on all microorganisms with minimum inhibitory concentration values less than 0.7 mg/mL. In the case of cholera toxin-induced diarrhea, epicatechin was the most potent flavonoid with IC50 of 14.7 mg/kg. Conclusion: Epicatechin and tiliroside were the flavonoids responsible for antimicrobial andantidiarrheal activities of C. pentadactylon. Its antiprotozoal, antibacterial, and antidiarrheal properties are in good agreement with the traditional medicinal use of C. pentadactylon for the treatment of infectious diarrhea. SUMMARY Epicatechin was the most potent antiamoebic and antigiardial compound with IC50 values of 1.9 μg/mL for E. histolytica and 1.6 μg/mL for G. lamblia.Tiliroside showed antibacterial activity against all microorganisms tested with MIC values less than 0.7 mg/mL.Epicatechin was the most potent flavonoid on cholera toxin-induced diarrhea with IC50 of 14.7 mg/kg. Abbreviations used: MECP: Methanol extract of C. pentadactylon

This paper presents the effect of auxiliary energy on rhein, kaempferol and astragalin extraction from Cassia alata . The effect of auxiliary energy was examined by performing extraction using either the ultrasonic assisted extraction (UAE) or microwave assisted extraction (MAE). A dried plant material with size ranging from 125 μm to 800 μm was used throughout this work. The rhein, kaempferol and astragalin quantification and identification was performed using ultra-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometer. The presence of rhein, kaempferol and astragalin were identified and compared with external standards.The residence time, neutral mass and mass fragmentationpattern between the standard and plant extract are also observed. It was found that the extraction yield of rhein, kaempferol and astragalin were higher with UAE method compared to MAE method due to degradation of active component occur. The findings in this work may serve as a useful guide to select the extraction method used to maximise the yield of rhein, kaempferol and astragalin extraction from C. alata.

Ethnopharmacological relevance The leaves of Sapium sebiferum (L.) Roxb. have long been used in Traditional Chinese Medicine (TCM) for the treatment of eczema, shingles, edema, swelling, ascites, scabs, and snakebites, among other maladies. The present study was an outreach research behind our previous study and aimed to analyze the chemical composition of phenolic extracts of Sapium sebiferum leaves and evaluate their effects on allergic contact dermatitis (ACD). Materials and methods The main compounds of Sapium sebiferum leaves were identified using UPLC-PDA method by comparing retention times and UV–vis spectra with those of reference standards. Their effects on ACD were examined using a dinitrofluorobenzene (DNFB) induced mice ACD model. Chemical parameters including reactive oxygen species (ROS), MDA and GSH/T-GSH ratio of ear tissue were also determined. Results Seven compounds including gallic acid, ellagic acid, hyperin, isoquercitrin, astragalin, quercetin and kaempferol were identified from Sapium sebiferum leaves, and their contents were also determined; ellagic acid, isoquercitrin and astragalin were in the majority. Phenolic extracts of Sapium sebiferum leaves exhibited dose-dependent inhibitory effects on edema induced by ACD at doses of 0.03, 0.1 and 0.3 mg/ear. The application of extracts also decreased ROS and MDA levels and increased GSH/T-GSH ratio of ear tissue. Conclusion The present study demonstrated that the bioactivity of Sapium sebiferum leaves may be due to the existence of the identified phenolic components, and several high polarity compounds were also active. The beneficial effect of Sapium sebiferum leaves on skin diseases is based on its antioxidant activity or effects on antioxidant defense system.

We investigated the root of Podophyllum hexandrum as a potential source of lead bioactive metabolites with anticancer activity. The present study led to the isolation of six known aryltetralin-type lignans designated as 4'-demethyl-deoxypodophyllotoxin (1), podophyllotoxin (2), 4'-demethyl-podophyllotoxin (3), podophyllotoxin-4-O-β-d-glucopyranoside (4), 4'-demethyl-deoxypodophyllotoxin-4-O-β-d-glucopyranoside (5), 4'-demethyl-podophyllotoxin-4-O-β-d-glucopyranoside (6), along with three known flavones Kaempferol (7), Quercetin (8), Astragalin (9) from the root of P. hexandrum. Compounds (1-9) exhibited the remarkable cytotoxic potential in diverse cancer cell lines. 5 therapeutic potential was extensively studied first time which exhibiting antiproliferative and ROS generating activity than its non-glycoside analogue 1. Furthermore, 5 augmented the apoptotic cascades in MCF-7 breast cancer cells, viz. nuclear condensation, membrane blebbing, probably by destabilizing the micro-tubular protein tubulin. Strikingly, our docking study and in vitro assays demonstrate that 5 binds to and modulate checkpoint kinase-2, a key cell cycle regulatory protein in normal and cancer cells.

Background Eotaxin proteins are a potential therapeutic target in treating the peribronchial eosinophilia associated with allergic airway diseases. Since inflammation is often associated with an increased generation of reactive oxygen species (ROS), oxidative stress is a mechanistically imperative factor in asthma. Astragalin (kaempferol-3-O-glucoside) is a flavonoid with anti-inflammatory activity and newly found in persimmon leaves and green tea seeds. This study elucidated that astragalin inhibited endotoxin-induced oxidative stress leading to eosinophilia and epithelial apoptosis in airways. Methods Airway epithelial BEAS-2B cells were exposed to lipopolysaccharide (LPS) in the absence and presence of 1–20 μM astragalin. Western blot and immunocytochemical analyses were conducted to determine induction of target proteins. Cell and nuclear staining was also performed for ROS production and epithelial apoptosis. Results When airway epithelial cells were exposed to 2 μg/ml LPS, astragalin nontoxic at ≤20 μM suppressed cellular induction of Toll-like receptor 4 (TLR4) and ROS production enhanced by LPS. Both LPS and H2O2 induced epithelial eotaxin-1 expression, which was blocked by astragalin. LPS activated and induced PLCγ1, PKCβ2, and NADPH oxidase subunits of p22phox and p47phox in epithelial cells and such activation and induction were demoted by astragalin or TLR4 inhibition antagonizing eotaxin-1 induction. H2O2-upregulated phosphorylation of JNK and p38 MAPK was dampened by adding astragalin to epithelial cells, while this compound enhanced epithelial activation of Akt and ERK. H2O2 and LPS promoted epithelial apoptosis concomitant with nuclear condensation or caspase-3 activation, which was blunted by astragalin. Conclusions Astragalin ameliorated oxidative stress-associated epithelial eosinophilia and apoptosis through disturbing TLR4-PKCβ2-NADPH oxidase-responsive signaling. Therefore, astragalin may be a potent agent antagonizing endotoxin-induced oxidative stress leading to airway dysfunction and inflammation.

Tetracera scandens Linn. (Dilleniaceae), locally known as Mempelas Kasar, is traditionally used in folk remedies by various indigenous people in different countries including Malaysia for the treatment of rheumatism, inflammatory diseases, hepatitis, internal pains, urinary disorders, dysentery, sore throat, gout and diabetes infirmities; for lowering hypertension; and for child birth. In this study, phytochemical analysis of T. scandens leaf methanol (MeOH) extract was carried out for the first time and afforded three terpenoids (stigmasterol, betulinic acid and an isomeric mixture of sitosterol (∆5) glycoside and stigmasterol (∆5,22) glycoside) and six flavonoids (namely, kaempferol, quercetin, isoscutellarein, hypoletin, astragalin and kaempferol-3-O-(6″-O-p-trans-coumaroyl) glucoside, a rare compound which has been isolated for the first time from family Dilleniaceae). Structures of all compounds were elucidated through extensive UV–Vis, mass, IR and NMR spectral analysis. The occurrence of all these compounds is being reported for the first time from this plant. Due to the rare occurrence of hypoletin (3′,4′,5,7,8-pentahydroxyflavone) in plants, its in vitro antidiabetic effect was explored. Hence, the treatment of hypoletin in a dose-dependent manner was examined on the induction of lipid accumulation by using Oil Red O staining and glucose regulation in 3T3-L1 adipocytes in vitro with regard to its preventive role in the management of diabetes. After 8 days, morphological changes and high lipid accumulation activity were observed in cells treated with 10 μg/mL of hypoletin concentration (P < 0.01). In addition, the intracellular fat accumulation increased by up to 79.7 % relative to MDI-treated control cells at a dose of 10 μg/mL. Furthermore, insulin-induced 2-deoxy-d-[3H] glucose uptake was significantly increased (P < 0.001) in hypoletin-treated cells as compared to control (DMSO cells). Our results suggest that hypoletin could be useful for the management of type 2 diabetes due to its adipocyte stimulation and glucose uptake activity.

Artemisia herba-alba (A. h.-a.) has wide use in traditional medicine for the relief of coughing, healing external wounds, and treatment of pain associated with gastrointestinal disturbances. We investigated in vivo antinociceptive and anti-inflammatory activities of an aqueous extract (aq. ex.) and two isolated compounds obtained from aerial parts of A. h.-a. The analgesic effects of aq. ex. (10, 31.6, 100, 316, and 1000 mg/kg), astragalin, and eupatilin (both, 0.316, 1, 3.16, 10, 31.6, and 100 mg/kg) were studied using the hot-plate test in mice and formalin test in rats. The effects were compared with those of 5 mg/kg morphine. Dosedependent analgesic effects of aq. ex., astragalin, and eupatilin were clearly manifested in both hot-plate assay and early and late phases of formalin-induced paw licking. These effects were significantly but partly reduced by the opioid receptor antagonist naloxone (5 mg/kg). The same range of doses of aq. ex., astragalin, and eupatilin caused dose-dependent suppression of carrageenan-induced paw edema in rats. Thus, we demonstrated that A. h.-a. possesses noticeable antinociceptive and anti-inflammatory activities; our data support the reasons for using this plant as a remedy for treatment of pain and inflammation. Antinociceptive and anti-inflammatory actions of A. h.-a. are considerably related to the presence of astragalin and eupatilin Білий полин (Artemisia herba-alba – A. h.-a.) знаходить широке застосування в традиційній медицині. Його вживають для припинення кашлю, лікування ран, вгамування болю при шлунково-кишкових розладах та ін. В експериментах in vivo ми досліджували антиноцицептивні та протизапальні ефекти водного екстракту (в. екс.) та двох окремих компонентів, отриманих із надземних частин A. h.-a. Аналгетичні ефекти в. екс. (10, 31.6, 100, 316 та 1000 мг/кг), астрагаліну та еупатиліну (обидва в дозах 0.316, 1, 3.16, 10, 31.6 та 100 мг/кг) визначались у тесті «гарячої платівки» на мишах та формаліновому тесті на щурах; ці ефекти порівнювали з такими морфіну. Залежні від дози аналгетичні впливи в. екс., астрагаліну та еупатиліну яскраво проявлялись як у тесті «гарячої платівки», так і в перебігу ранньої та пізньої фаз реакції лизання кінцівки, індукованої ін’єкцією формаліну. Ці ефекти усувались, проте лише частково, антагоністом опіоїдних рецепторів налоксоном (5 мг/кг). Аналогічні дози в. екс., астрагаліну та еупатиліну забезпечували дозозалежне пригнічення індукованого карагенаном набряку кінцівки у щурів. Таким чином, ми продемонстрували, що для A. h.- a. характерні істотні антиноцицептивна та протизапальна властивості. Наші дані підтверджують обгрунтованість застосування цієї рослини як лікувального засобу в традиційній медицині. Згадані властивості A. h.-a. в істотній мірі залежать від наявності в її складі астрагаліну та еупатиліну.

The chemical constituents of fistular onion stalk obtained by supercritical CO(2) extraction were separated and purified by silica gel and sephadex LH-20 gel column chromatography and the preparative TLC method and four flavonoids were obtained. On the basis of the spectral data, they were structurally identified as (+)-catechin, (-)-epicatechin, astragalin, and 3-O-beta-D(2-O-beta-D-glucopyranosyl)-glucopyranosides of kaempferol.

Background: We previously found that persimmon leaf extract contains antiallergic substances that inhibit histamine release by human basophilic cell line KU812 in response to cross-linkage of FcϵRI. Objectives: The purpose of this study was to identify substances in the persimmon leaf extract that are responsible for the effect and to examine their in vivo effects on the allergic mouse model. Methods: HPLC analysis of persimmon leaf extract was done to measure its content. Inhibitory activity of persimmon leaf extract or its major constituent of flavonoids (astragalin) on the histamine release by KU812 cells was examined. To investigate the effects of these substances in vivo, models of passive cutaneous anaphylaxis and atopic dermatitis mice (NC/Nga) were used. Results: Persimmon leaf extract or astragalin inhibited histamine release from KU812 in response to cross-linkage of FcϵRI. Oral intake of both substances dose dependently inhibited passive cutaneous reactions. Moreover, oral administration of these substances to NC/Nga atopic dermatitis–model mice led to a striking suppression of the development of dermatitis, scratching behavior, and serum IgE elevation. Histologic analyses revealed that infiltration of inflammatory cells, especially degranulated mast cells, thickening of the epidermis, and prominent hyperkeratosis, were significantly reduced. Immunologic studies showed that the capacity of spleen T cells to produce both IL-4 and IL-13, but not IFN-γ, was downregulated by means of oral intake of these substances. Conclusion: This study demonstrates a novel activity of astragalin and the dramatic effect of persimmon leaf extract and astragalin on atopic dermatitis–model mice. (J Allergy Clin Immunol 2000;106:159-66.)

Three dry bean (Phaseolus vulgaris L.) genotypes differing in seedcoat color, mineral brown (P C D J G B v), yellow brown (P C D J G b v), and pale greenish yellow (P C D J g b v), were analyzed phytochemically. Kaempferol 3-O-β-d-glucoside (astragalin) was isolated and identified by nuclear magnetic resonance spectroscopy from all three genotypes, and was the main flavonoid monomer present. Flavonoid polymers (condensed tannins) were detected by thin layer chromatography, but anthocyanins were not detected in the three genotypes. High pressure liquid chromatography analyses indicated that astragalin was present at similar concentrations in pale greenish yellow and mineral brown genotypes, but was significantly lower in yellow brown. Presently, we do not know the functions of the G and B color genes, although the presence of astragalin in the three genotypes studied indicates these genes do not appear to act in a qualitative manner with regard to astragalin production, but may control the amount of astragalin present. Subtle differences in color between these genotypes may be due to the amount and type of tannins which have secondarily polymerized with phenolics and flavonoid monomers.

(3R)-O-beta-D-Glucopyranosyloxy-5-phenylvaleric acid (1), (3R)-O-beta-D-glucopyranosyloxy-5-phenylvaleric acid n-butyl ester (2), and a new dihydrochalcone diglycoside 4'-O-[beta-D-glucopyranosyl-(1--6)-glucopyranosyl]oxy-2'-hydroxy-3', 6'-dimethoxydihydrochalcone (3), together with six known flavonoid glycosides [kaempferol-3-O-beta-D-glucopyranoside (= astragalin) (4), kaempferol-3-O-beta-D-galactopyranoside (5), quercetin-3-O-beta-D-glucopyranoside (= isoquercitrin) (6), quercetin-3-O-beta-D-galactopyranoside (= hyperoside) (7), quercetin-3-O-(2''-O-galloyl)-beta-D-glucopyranoside (8), and quercetin-3-O-beta-D-glucuronopyranoside (9)] were isolated from the aerial parts of Polygonum salicifolium. The structure elucidation of the isolated compounds was performed by spectroscopic (UV, IR, ESI-MS, 1D- and 2D-NMR), chemical (methylation, enzymatic hydrolysis, partial synthesis), and chromatographic methods (HPLC, Chiralcel OD). The flavonoid glycosides (4-9) demonstrated scavenging properties toward the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical in TLC autographic assays.

Nine flavonoids (1-9) were isolated from the leaves of Morus alba (Moraceae). The structures of compounds were determined to be kaempferol-3-O-beta-D-glucopyranoside (astragalin, 1) kaempferol-3-O-(6"-O-acetyl)-beta-D-glucopyranoside (2), quercetin-3-O-(6"-O-acetyl)-beta-D-glucopyranoside (3), quercetin-3-O-beta-D-glucopyranoside (4), kaempferol-3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (5), quercetin-3-O-alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranoside (rutin, 6), quercetin-3-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (7), quercetin-3,7-di-O-beta-D-glucopyranoside (8) and quercetin (9) on the basis of spectroscopic and chemical studies. Compounds 7 and 9 exhibited significant radical scavenging effect on 1,1-diphenyl-2-picrylhydrazyl radical.

This paper describes the isolation and identification of an antimicrobial compound againstStreptococcus mutansfrom the leaves ofDiospyros kaki. After repeated chromatography of the weakly acidic fraction of acetone extracts, an antimicrobial compound againstS.mutanswas isolated. The chemical structure of the active compound was elucidated by spectroscopic methods, and identified as kaempferol. Kaempferol is an aglycone of astragalin (kaempferol 3-O-β-D-glucopyranoside) which has been isolated from the leaves ofD.kaki. The minimum inhibitory concentrations of kaempferol againstStreptococcus mutans, Escherichia coli, Bacillus subtilis, andStaphylococcus aureuswere estimated.

In the extreme north, Papaver radicatum s.l. occurs in a yellow and in a white-flowered type. The more severe the weather conditions the higher the frequency of the white phenotype. The colouring agents in the petals are all flavonol glucosides; in the yellow flowers gossypitrin (1) and herbacitrin (2), in the white ones the kaempferol glucoside astragalin (3). Only astragalin shows UV reflection, which is valuable in attracting insect pollinators, so very likely the presence of astragalin may be responsible for the success of the white-flowered type under suboptimal weather conditions. We were unable to confirm the hypothesis that the yellow colouring agents, gossypitrin and herbacitrin, should be more costly to produce than the white one, astragalin, as an investment in order to obtain the higher temperature observed in yellow flowers. The distribution pattern with high frequency of the yellow-flowered poppies where the likelihood of sunshine is high, may have other reasons than carbon allocation to the colouring agents. Yellow flowers are more showy than white ones, and although this in general benefits pollination it may also increase the risk of herbivory. White flowers are at the same time believed to escape herbivory and obtain a better pollination under dull weather conditions, due to the UV-reflection by astragalin.

Bioassay-guided fractionation of the methanol extract of aerial parts from Helianthemum glomeratum afforded five antiprotozoal flavonol glycosides: tiliroside, kaempferol-3-O-(3″,6″di-O-E-p-coumaroyl)-βd-glucopyranoside, astragalin, quercitrin and isoquercitrin. The invitro antiprotozoal assay showed that tiliroside was the most potent antiamoebic and antigiardial compound with IC50 values of 17.5 µg/mL for Entamoeba histolytica and 17.4 µg/mL for G. lamblia. Isoquercitrin showed selectivity against E. histolytica (IC50 14.7 µg/mL) and quercitrin toward G. lamblia (IC50 24.3 µg/mL). All isolated compounds were less active than metronidazole and emetine, two antiprotozoal drugs used as positive controls. Copyright © 2006 John Wiley & Sons, Ltd.

From the leaves of Salvadora persica L. eleven flavonoidal glycosides are isolated and identified. Seven of them: Isorhamnetin-3-O-robinobioside, Kaempferol-3-O-robinobioxide, Narcissin, Kaempferol-3-Orutinoside, Isorhamnetin-3-O-b-galactoside, Astragalin and Isorhamnetin-3-O-b-D-glucoside are isolated for the first time form the genus Salvadora. While the others four are identified as: Isorhamnetin-3-(2,6-di-rhamnopyranosyl-galactopyranoside), Mauritianin, Isorhamnetin-3-O-(2-Glc-rhamnosylrutinoside) and Kaempferol-3-O-(2-Glc-rhamnosylrutinoside) and reported for the first time in family Salvadoraceae.

The herbs of Euphorbia supina (Euphorbiaceae) have been used to treat hemorrhage, chronic bronchitis, hepatitis, jaundice, diarrhea, gastritis, and hemorrhoids as a medicinal herb. This work is aimed to qualitatively and quantitatively analyze the polyphenols with peroxynitrite-scavenging activities. The eight compounds: gallic acid, methyl gallate, avicularin, astragalin, juglanin, isoquercitrin 6″-gallate, astragalin 6″-gallate, and ellagic acid, were isolated from E. supina and used for HPLC analysis and peroxynitrite (ONOO(-))-scavenging assay. Simultaneous analysis of the eight compounds was performed on MeOH extract and its fractions. The contents in MeOH extract and peroxynitrite-scavenging activities of the dimer of gallic acid, ellagic acid (15.64 mg/g; IC50 0.89 μM), and two galloylated flavonoid glycosides, astragalin 6″-gallate (13.72 mg/g; IC50 1.43 μM) and isoquercitrin 6″-gallate (16.99 mg/g; IC50 1.75 μM), were high, compared to other compounds. The legendary uses of E. supina could be attributed to the high content of polyphenols, particularly ellagic acid, isoquercitrin 6″-gallate, and astragalin 6″-gallate as active principles.

A sensitive high-performance liquid chromatography method coupled with photodiode array detection was developed for the simultaneous determination of six major constituents in Flaveria bidentis (L.) Kuntze: hyperoside, patuletin-3-O-glucoside, isorhamnetin 3-sulfate, astragalin, 6-methoxykaempferol-3-O-galactoside and α-terthienyl. The chemical fingerprint of Flaveria bidentis (L.) Kuntze leaves was established using raw materials of 12 batches in China. The chromatographic separations were obtained by using an Eclipse XDB-C18 reserved-phase column (150 × 4.6 mm i.d., 5 µm) using gradient elution with water (0.0125% trifluoroacetic acid, v/v) and acetonitrile at a flow rate of 1.0 mL/min, an operating temperature of 30°C and a detection wavelength of 360 nm. The new method was validated by linearity, limits of detection and quantification, precision, reproducibility, stability and recovery, and was also successfully applied to the simultaneous determination of components in Flaveria bidentis (L.) Kuntze. The results indicate that this multi-component determination method in combination with chromatographic fingerprint analysis is suitable for the quantitative analysis and identification of Flaveria bidentis (L.) Kuntze.

We report the production of astragalin (AST) from regiospecific modifications of naringenin (NRN) in Escherichia coli BL21(DE3). The exogenously supplied NRN was converted into dihydrokaempferol (DHK) and then kaempferol (KMF) in the presence of flavanone-3-hydroxylase (f3h) and flavonone synthase (fls1) from Arabidopsis thaliana, respectively. KMF was further modified to produce AST by 3-O-glucosylation utilizing the endogeneous UDP-glucose in presence of UGT78K1 from Glycine max. To increase the intracellular UDP-glucose concentration by channeling the carbon flux toward UDP-glucose at the branch point of glucose-6-phosphate (G6P), the chromosomal glucose phosphate isomerase (pgi) and D-glucose-6-phosphate dehydrogenase (zwf) were knocked-out in E. coli BL21(DE3). The two enzymes directly involved in the synthesis of UDP-glucose from G6P, phosphoglucomutase (nfa44530) from Nocardia farcinia and glucose-1-phosphate uridylyltransferase (galU) from E. coli K12 were overexpressed, which successfully diverted the carbon flow from glycolysis to the synthesis of UDP-glucose. Furthermore, to prevent the dissociation of UDP-glucose into UDP and glucose, the UDP-glucose hydrolase (ushA) was deleted. The E. coli ΔpgiΔzwfΔushA mutant harboring the UDP-glucose biosynthetic pathway and the aforementioned genes for the regiospecific glucosylation produced 109.3 mg/L (244 µM) of AST representing 48.8% conversion from 500 µM of NRN in 60 h without any supplementation of extracellular UDP-glucose. Biotechnol. Bioeng. 2013; 110:2525–2535. © 2013 Wiley Periodicals, Inc.

Moringa oleiferaLamarck (Moringaceae) is used as a multipurpose medicinal plant for the treatment of various diseases. Isoquercetin, astragalin, and crypto-chlorogenic acid have been previously found to be major active components in the leaves of this plant. In this study, a thin-layer-chromatography (TLC-)densitometric method was developed and validated for simultaneous quantification of these major components in the 70% ethanolic extracts ofM. oleiferaleaves collected from 12 locations. The average amounts of crypto-chlorogenic acid, isoquercetin, and astragalin were found to be 0.0473, 0.0427, and 0.0534% dry weight, respectively. The method was validated for linearity, precision, accuracy, limit of detection, limit of quantitation, and robustness. The linearity was obtained in the range of 100–500 ng/spot with a correlation coefficient (r) over 0.9961. Intraday and interday precisions demonstrated relative standard deviations of less than 5%. The accuracy of the method was confirmed by determining the recovery. The average recoveries of each component from the extracts were in the range of 98.28 to 99.65%. Additionally, the leaves from Chiang Mai province contained the highest amounts of all active components. The proposed TLC-densitometric method was simple, accurate, precise, and cost-effective for routine quality controlling ofM. oleiferaleaf extracts.

We evaluated the antioxidant properties of mulberry leaves extract (MLE) and flavonoids isolated from MLE. MLE was prepared by extraction with methanol. Flavonoids were analyzed by high-performance liquid chromatography. Oxidative hemolysis of normal human red blood cells (RBCs) was induced by the aqueous peroxyl radical [2,2'-Azobis (2-amidinopropane) dihydrochloride, AAPH]. MLE contained three flavonoids in the order quercetin (QC) > kaempferol (KF) > astragalin (AG). Oxidative hemolysis of RBCs induced by AAPH was suppressed by MLE, AG, KF, and QC in a time- and dose-dependent manner. MLE and these three flavonoids prevented the depletion of cystosolic antioxidant glutathione (GSH) in RBCs. AG had the greatest protective effect against AAPH-induced oxidative hemolysis and GSH depletion in RBCs.