lignans and protocatechuic-acid

Eucommia ulmoides Oliv. (E. ulmoides) is a valuable and nourishing medicinal herb in China that has been used in the treatment of hypertension. Given the fact that most traditional Chinese medicine is mainly used to treat disease, investigating the pharmacokinetics of traditional Chinese medicines in the pathological state is more useful than that in the normal state. However, the differences in the absorption kinetics of active ingredients of E. ulmoides extract between pathological and physiological conditions have not been reported. Therefore, in this study, the rat intestinal in situ circulatory perfusion model was used to investigate the differences in absorption kinetics of seven active ingredients of E. ulmoides extract in normal and spontaneously hypertensive rats, namely, genipinic acid, protocatechuic acid, neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid, (+)-pinoresinol di-O-β-D-glucopyranoside and (+)-pinoresinol 4'-O-β-D-glucopyranoside. Our results indicate that the pathological state of spontaneous hypertension may change the absorption of active components of E. ulmoides extracts, and these findings may provide a reference for improving the rational use of E. ulmoides in the clinic.

Topics: Animals; Antihypertensive Agents; Body Fluids; Chlorogenic Acid; Eucommiaceae; Furans; Hydroxybenzoates; Intestinal Absorption; Lignans; Plant Extracts; Rats; Rats, Inbred SHR; Rats, Wistar

The effects of roasting and in vitro digestion on total phenolic content (TPC), total flavonoid content (TFC), phenolic profiles, and antioxidant activity of water-soluble extracts from six varieties of sesame were investigated in this study. Our results showed that the major phenolic compounds in raw, roasted and digested sesame were gallic acid (GA), protocatechuic acid (PA), 4-hydroxybenzoic acid (4 HBA), ferulic acid (FA) and quercetin (Quer). Roasting significantly increased the TPC, pinoresinol diglucoside (PD), sesamol, as well as the content of phenolic compounds (especially GA, PA, 4 HBA and Quer) in sesame, but kept or reduced the TFC, sesamin and sesamolin. After roasting, the antioxidant potency composite index (ACI) of six varieties of sesame was significantly increased by 29.8%-216.6%. Additionally, the ACI of gastric digestion was significantly higher than that of oral and intestinal digestion during the in vitro digestion of the roasted-sesame, except for the varieties of Ganzhi 9 and Ganzhi 17. This study showed that five phenolic compounds (GA, PA, 4 HBA, p-coumaric acid, Quer) and sesamol of the water-soluble extracts contributed to the antioxidant activities of the digestive products of sesame.

Topics: Anticarcinogenic Agents; Antioxidants; Benzodioxoles; Coumaric Acids; Digestion; Dioxoles; Flavonoids; Gallic Acid; Hydroxybenzoates; Lignans; Parabens; Phenol; Phenols; Plant Extracts; Principal Component Analysis; Propionates; Quercetin; Seeds; Sesamum

The bark of Eucommia ulmoides is a well-known Chinese herbal medicine that is used to regulate blood pressure and reduce blood sugar and fats, as well as an antioxidant and antimicrobial agent. Here we describe the development of a sensitive ultrahigh performance liquid chromatography-tandem mass spectrum method for the simultaneous determination of five major active ingredients of E. ulmoides bark extract, namely, geniposidic acid (GA), protocatechuic acid (PCA), chlorogenic acid (CA), (+)-pinoresinol di-O-β-D-glucopyranoside (PDG) and (+)-pinoresinol 4'-O-β-D-glucopyranoside (PG), in rat plasma. The preliminary steps in the plasma analysis were the addition of an internal standard and acidification (0.1 % formic acid), followed by protein precipitation with methanol. Separation of the active ingredients was performed on an ACQUITY UPLC® BEH C18 column (2.1 × 50 mm; internal diameter 1.7 µm) at a flow rate of 0.35 mL/min, with acetonitrile/water containing 0.1 % formic acid as the mobile phase. Detection was performed on a triple quadrupole tandem mass spectrometer via electrospray ionization source with positive and negative ionization modes. All calibration curves showed good linearity (r ≥ 0.997) over the concentration range with the low limit of quantification between 4.45 and 54.9 ng/mL. Precision was evaluated by intra- and inter-day assays, and the percentages of the relative standard deviation were all within 15 %. Extraction efficiency and matrix effect were 84.3-102.4 % and 98.1-112.2 %, respectively. The validated method was successfully applied to the pharmacokinetic study in rats after oral administration of E. ulmoides extract. The results indicate that the pharmacokinetic properties of GA differ from those of PCA, CA, PDG and PG, respectively.

Topics: Animals; Chlorogenic Acid; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Eucommiaceae; Furans; Hydroxybenzoates; Iridoid Glucosides; Lignans; Male; Plant Extracts; Plasma; Rats; Rats, Sprague-Dawley; Tandem Mass Spectrometry

A new caffeate compound, (E)-erythro-syringylglyceryl caffeate (1), was isolated from the roots and rhizomes of Nardostachys chinensis Batal., together with nine known phenolic compounds, including (+)-licarin A (2), naringenin 4', 7-dimethyl ether (3), pinoresinol-4-O-β-D-glucoside (4), caraphenol A (5), Z-miyabenol C (6), protocatechuic acid (7), caffeic acid (8), gallic acid (9) and vanillic acid (10). Their chemical structures were elucidated on the basis of spectroscopic data and physicochemical properties. Furthermore, this is the first report of compounds 2, 5 and 6 from Nardostachys genus.

Topics: Caffeic Acids; Flavanones; Furans; Glucosides; Hydroxybenzoates; Lignans; Nardostachys; Plant Roots; Rhizome; Vanillic Acid

A simple and accurate liquid chromatographic method was developed for the simultaneous determination of six constituents in the fruit of Acanthopanax sessiliflorus. The conditions of sample extraction were optimised by using orthogonal design. The method provided good accuracy with recoveries in the range of 95.6-101.6% and good precision with RSD values less than 3.0%, which has been successfully applied to the quantitative determination of the six compounds in the fruit of A. sessiliflorus from two maturation periods.

Topics: Chromatography, High Pressure Liquid; Coumarins; Eleutherococcus; Fruit; Furans; Glucosides; Hydroxybenzoates; Lignans; Plant Extracts; Quercetin; Reference Standards

One alkyl glycoside, saussurostelloside A (1), two phenolic glycosides, saussurostellosides B1 (2) and B2 (3), and 27 known compounds, including eleven flavonoids, seven phenolics, six lignans, one neolignan, one phenethyl glucoside and one fatty acid, were isolated from an ethanol extract of Saussurea stella (Asteraceae). Their structures were elucidated by NMR, MS, UV, and IR spectroscopic analysis. Of the known compounds, (+)-medioresinol-di-O-β-D-glucoside (7), picraquassioside C (10), and diosmetin-3'-O-β-D-glucoside (27) were isolated from the Asteraceae family for the first time, while (+)-pinoresinol-di-O-β-D-glucoside (6), di-O-methylcrenatin (11), protocatechuic acid (14), 1,5-di-O-caffeoylquinic acid (17), formononetin (28), and phenethyl glucoside (29) were isolated from the Saussurea genus for the first time. The anti-inflammatory activities of three new compounds (1-3), five lignans ((-)-arctiin (4), (+)-pinoresinol-4-O-β-D-glucoside (5), (+)-pinoresinol-di-O-β-D-glucoside (6), (+)-medioresinol-di-O-β-D-glucoside (7) and (+)-syringaresinol-4-O-β-D-glucoside (8)), one neolignan (picraquassioside C (10)), and one phenolic glycoside (di-O-methylcrenatin (11)) were evaluated by testing their inhibition of the release of β-glucuronidase from PAF-stimulated neutrophils. Only compound 5 showed moderate inhibition of the release of β-glucuronidase, with an inhibition ratio of 39.1%.

Topics: Animals; Anti-Inflammatory Agents; Coumaric Acids; Disaccharides; Female; Flavonoids; Furans; Glucosides; Glucuronidase; Glycosides; Hydroxybenzoates; Inflammation; Isoflavones; Lignans; Male; Molecular Structure; Neutrophils; Phytotherapy; Plant Extracts; Platelet Activating Factor; Quinic Acid; Rats, Wistar; Saussurea

This work reports isolation of an unusual lignan with a bicyclic [2.2.2] octene skeleton, named rufescenolide (1), from stems of Cordia rufescens, along with β-sitosterol, stigmasterol, syringaldehyde, 3-β-O-D-glucopyranosyl-sitosterol, methyl caffeate, 4-methoxy-protocatechuic acid and methyl rosmarinate. Structural characterizations employed IR spectroscopic, ESIHRMS and mono and dimensional NMR spectroscopy.

Topics: Bridged Bicyclo Compounds; Caffeic Acids; Cordia; Hydroxybenzoates; Lignans; Magnetic Resonance Spectroscopy; Molecular Structure; Octanes; Plant Stems; Sitosterols; Stigmasterol