lignans and kaempferol

In this study, the chloroform-soluble extract of Cuscuta auralis was separated successfully using off-line two-dimensional high-performance countercurrent chromatography, yielding a γ-pyrone, two alkaloids, a flavonoid, and four lignans. The first-dimensional countercurrent separation using a methylene chloride/methanol/water (11:6:5, v/v/v) system yielded three subfractions (fractions I-III). The second-dimensional countercurrent separations, conducted on fractions I-III using n-hexane/ethyl acetate/methanol/water/acetic acid (5:5:5:5:0, 3:7:3:7:0, and 1:9:1:9:0.01, v/v/v/v/v) systems, gave maltol (1), (-)-(13S)-cuscutamine (2), (+)-(13R)-cuscutamine (3), (+)-pinoresinol (4), (+)-epipinoresinol (5), kaempferol (6), piperitol (7), and (9R)-hydroxy-d-sesamin (8). To the best of our knowledge, maltol was identified for the first time in Cuscuta species. Furthermore, this report details the first full assignment of spectroscopic data of two cuscutamine epimers, (-)-(13S)-cuscutamine and (+)-(13R)-cuscutamine.

Topics: Alkaloids; Chloroform; Chromatography, High Pressure Liquid; Circular Dichroism; Countercurrent Distribution; Cuscuta; Flavonoids; Furans; Hexanes; Kaempferols; Lignans; Magnetic Resonance Spectroscopy; Plant Extracts; Pyrones; Seeds; Spectrophotometry

We examined the effects of ambient, non-stressing ultraviolet (UV)-B (280-315nm) level combined with different intensities of photosynthetic active radiation (PAR, 400-700nm) on the accumulation of the lignan (-)-hinokinin, in leaves and stems of Hydrocotyle leucocephala. Plants were exposed in sun simulators under almost natural irradiance and climatic conditions to one of four light regimes, i.e. two PAR intensities (906 and 516μmolm(-2)s(-1)) including or excluding UV-B radiation (0 and 0.4Wm(-2)). Besides hinokinin, we identified three chlorogenic acid isomers, one other phenolic acid, 12 quercetin, and five kaempferol derivatives in the H. leucocephala extracts. Hinokinin was most abundant in the stems, and its accumulation was slightly enhanced under UV-B exposure. We therefore assume that hinokinin contributes to cell wall stabilization and consequently to a higher resistance of the plant to environmental factors. Quercetin derivatives increasingly accumulated under UV-B and high PAR exposure at the expense of kaempferols and chlorogenic acids, which was apparently related to its ability to scavenge reactive oxygen species. In general, the concentration of the constituents depended on the plant organ, the leaf age, the light regimes, and the duration of exposure. The distribution pattern of the compounds within the examined organs was not influenced by the treatments. Based on the chemical composition of the extracts a principal component analysis (PCA) enabled a clear separation of the plant organs and harvesting dates. Younger leaves mostly contained higher phenylpropanoid concentrations than older leaves. Nevertheless, more pronounced effects of the light regimes were detected in older leaves. As assessed, in many cases the individual compounds responded differently to the PAR/UV-B combinations, even within the same phenylpropanoid class. Since this is the first report on the influence of light conditions on the accumulation of lignans in herbaceous plants, it opens many perspectives for a more precise elucidation of all involved biochemical and molecular processes.

Topics: 4-Butyrolactone; Benzodioxoles; Centella; Chlorogenic Acid; Flavonols; Hydroxybenzoates; Kaempferols; Lignans; Oxidative Stress; Photosynthesis; Plant Leaves; Plant Stems; Propanols; Quercetin; Ultraviolet Rays

A new γ-alkylated-γ-butyrolactone, named melongenolide A (1), along with nine known compounds were obtained from the roots of Solanum melongena, and their structures were identified as melongenolide A (1), (+)-syringaresinol (2), (+)-lyoniresinol (3), 5,5'-dimethoxy lariciresinol (4), (+)-(7R,8R)-4-hydroxy-3,3',5'-trimethoxy-8',9'-dinor-8,4'-oxyneoligna-7, 9-diol-7'-aldehyde (5), kaempferol-3-O-(2″,6″-di-O-p-trans-coumaroyl)-β-glucoside (6), arjunolic acid (7), vanillic acid (8), scoparone (9), and β-sitosterol (10). Compounds 2, 6, and 7 showed potent inhibitory effects on nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages, with IC50 values being 5.62 ± 0.86, 11.47 ± 0.98, and 27.75 ± 1.26 μmol·L(-1), respectively.

Topics: 4-Butyrolactone; Animals; Furans; Inflammation; Inhibitory Concentration 50; Kaempferols; Lignans; Macrophages; Mice; Nitric Oxide; Plant Extracts; Plant Roots; RAW 264.7 Cells; Solanum melongena; Triterpenes

Phytochemical and antimicrobial activity study on the ethanol extract of the leaves and stems of Loropetalum chinense led to the isolation of a new flavan-3-ol compounds, 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]-catechin (loropetaliside A) (1) and a new lignan glucoside, 1-(5-hydroxy-3-methoxyphenyl)-2-(2-β-glucopyranosyl-4-hydroxy-5-(1-(E)propen-3-ol)-phenyl)-propane-3-ol (loropetaliside B) (3) and several known compounds manglieside D (2), quercetin (4), kaempferol-3-O-D-glucopyranoside (5), quercetin-3-O-β-L-rhamnoside (6) and tiliroside (7). Their structures were elucidated on the basis of extensive spectroscopic analysis.

Topics: Anti-Infective Agents; Bacteria; Flavonoids; Glucosides; Hamamelidaceae; Kaempferols; Lignans; Plant Extracts; Plant Leaves; Plant Stems; Quercetin

To study the chemical constituents of the roots of Vaccinium bracteatum.. The constituents were separated and purified with chromatographic methods (including silica gel, Sephadex LH-20 and RP-18 column chromatography), and their structures were determined by spectroscopic methods (including MS, 1H-NMR and 13C-NMR).. 10 compounds were isolated from the roots of Vaccinium bracteatu and were elucidated as chlorogenic acid (1), pinoresinol (2), ferulic acid (3), kaempferol (4), trans-caffeic acid (5), beta-sitosterol (6), quercetin (7), oleanolic acid (8), apigenin (9) and luteolin (10).. Compounds 1 -3 are obtained from this plant for the first time.

Topics: Chlorogenic Acid; Coumaric Acids; Furans; Kaempferols; Lignans; Magnetic Resonance Spectroscopy; Plant Roots; Quercetin; Solvents; Vaccinium

Cuscuta chinensis and Cuscuta australis, the two botanical sources of the Chinese herbal medicine Tu-Si-Zi, were distinguished from each other based on qualitative and quantitative chemical analysis. By HPLC‑DAD‑MS, a total of 36 compounds were characterized from these two Cuscuta species, including 14 flavonoids, 17 quinic acid derivatives, and 5 lignans. In addition, HPLC‑UV was applied to determine seven major compounds (6 flavonoids plus chlorogenic acid) in 27 batches of Tu-Si-Zi. The results revealed that the amounts of the three classes of compounds varied significantly between the species. C. australis contained more flavonoids but less quinic acid derivatives and lignans than C. chinensis. Particularly, the amounts of kaempferol and astragalin in C. australis were remarkably higher than in C. chinensis. This finding could be valuable for the quality control of Tu-Si-Zi.

Topics: Chemistry Techniques, Analytical; Chromatography, High Pressure Liquid; Cuscuta; Drugs, Chinese Herbal; Flavonoids; Kaempferols; Lignans; Mass Spectrometry; Plant Extracts; Quinic Acid; Seeds

Estimation of dietary intake of polyphenols is difficult, due to limited availability of food composition data and bias inherent to dietary assessment methods. The aim of the present study was to evaluate the associations between the intake of polyphenol-rich foods and the urinary excretion of several phenolic compounds and therefore explore whether these phenolic compounds could be used as a biomarker of intake. Fifty-three participants of the SU.VI.MAX study (a randomised primary-prevention trial evaluating the effect of daily antioxidant supplementation on chronic diseases) collected a 24 h urine and a spot urine sample and filled a dietary record during a 2 d period. Thirteen polyphenols and metabolites, chlorogenic acid, caffeic acid, m-coumaric acid, gallic acid, 4-O-methylgallic acid, quercetin, isorhamnetin, kaempferol, hesperetin, naringenin, phloretin, enterolactone and enterodiol, were measured using HPLC-electrospray ionisation-MS-MS. In spot samples apple consumption was positively correlated to phloretin, grapefruit consumption to naringenin, orange to hesperetin, citrus fruit consumption to both naringenin and hesperetin, with r coefficients ranging from 0.31 to 0.57 (P < 0.05). The combination of fruits and/or fruit juices was positively correlated to gallic acid and 4-O-methylgallic acid, isorhamnetin, kaempferol, hesperetin, naringenin and phloretin (r 0.24-0.44, P < 0.05). Coffee consumption was positively correlated to caffeic and chlorogenic acids (r 0.29 and 0.63, P < 0.05 respectively). Black tea and wine consumption were positively correlated with gallic and 4-O-methylgallic acids (r 0.37-0.54, P < 0.001). The present results suggest that several polyphenols measured in a spot urine sample can be used as biomarkers of polyphenol-rich food intake.

Topics: 4-Butyrolactone; Adult; Antioxidants; Biomarkers; Caffeic Acids; Chlorogenic Acid; Coffee; Cohort Studies; Diet; Female; Flavonoids; Food; Fruit; Gallic Acid; Humans; Hydroxybenzoates; Kaempferols; Lignans; Male; Middle Aged; Phenols; Polyphenols; Vegetables; Wine