ABSTRACT
Thirty-one phenolic constituents were isolated and purified from the 95% ethanol extract of Sanguisorbae Radix by using various chromatographic techniques, including macroporous resin, silica gel, ODS, Sephadex LH-20 and semi-preparative HPLC. Their structures were elucidated by physicochemical properties, spectroscopic data (MS and NMR) and electronic circular dichroism (ECD) spectra, and identified as 3-methoxyl-2S,3S-epoxyflavanone (1a), 3-methoxyl-2R,3R-epoxyflavanone (1b), longifoin B (2), longifoin C (3), eriodictyol (4), naringenin (5), liquiritigenin (6), 5,3ʹ-dihydroxy-7,4ʹ-dimethoxyflavanone (7), naringenin-7-O-β-D-glucopyranoside (8), dihydroquercetin (9), dihydrokaempferol (10), (-)-garbanzol (11), (2R,3R)-4-methoxyl-distylin (12), kaempferol (13), quercetin (14), α,4,2′,4′-tetrahydroxydihydrochalcone (15), phloretin (16), (+)-catechin (17), ethyl (+)-cyanidan-3-ol-8-carboxylate (18), phyllocoumarin (19), methyl 3-methoxy-4,5-dihydroxybenzoate (20), 4,5-dimethoxy-3-hydroxybenzoic acid methyl ester (21), 3,4′-di-O-methylellagic acid (22), 3,4,3′-O-trimethylellagic acid (23), 3,3ʹ,4ʹ-O-trimethylellagic acid-4-O-β-D-xyloside (24), (3R)-thunberginol C (25), resveratrol (26), 1-hydroxypinoresinol (27), (7S,8S)-3-methoxy-3′,7-epoxy-8,4′-oxyneoligna-4,9,9′-triol (28), emodin-8-O-β-D-glucoside (29), phloracetophenone (30) and 4-(4′-hydroxyphenyl)-butan-2-one (31). Among them, compound 1a and 1b is a pair of new flavonoid enantiomers, compounds 2 and 3 are a pair of new epimers, while compounds 4, 5, 6, 9, 10, 13, 16 and 26 were obtained from S. officinalis for the first time, compounds 7, 8, 27, 30 and 31 were isolated for the first time from the S. officinalis genus, and compounds 11, 12, 15, 18, 19, 25, 28 and 29 were isolated for the first time from the Rosaceae. The antioxidant activities of compounds 1-24 were evaluated by activating the Nrf2 transcriptional pathway, which were measured by the dual-luciferase reporter gene assay in 293T cells. Compounds 4, 6-10, 12, 14, 17, 19, 20 and 22-24 showed significant Nrf2 agonistic effect compared with the control group at 25 μmol·L-1, which provided reference for the research of their antioxidant activity.
ABSTRACT
Objective: To study the low-polarity chemical constituents from the whole plants of Scrophularia dentata grown in Tibet. Methods: The compounds were isolated and purified by various column chromatography. Their structures were elucidated by means of spectral analyses (MS, 1H-NMR, and 13C-NMR). Results: Fifteen compounds were isolated and identified as oleanolic acid (1), 3-O-acetyloleanolic acid (2), stigmast-4-en-3-one (3), stigmast-4, 22-dien-3-one (4), 2, 6-dimethoxybenzoquinone (5), cerevisterol (6), cinnamic acid (7), spinasterol (8), β-sitosterol (9), 2-tritriacontanone (10), 2-(4-hydroxyphen-yl)-ethyl 1-dodecyloctadecanoate (11), apigenin (12), chrysoeriol (13), medioresinol (14), and syringaresinol (15). Conclusion: All the compounds are firstly isolated from this plant and compounds 2-6 and 10-15 are isolated from the plants of this genus for the first time.
ABSTRACT
Phytochemical investigation of the roots of Scrophularia buergeriana Miq. (Scrophulariaceae), resulted in the isolation of a new iridoid derivative named as buergerinin (1). Its structure was elucidated as rel-(1R, 5R, 6R)-(2-oxa-bicyclo[3.3.0]oct-7-en-6, 7-diyl)dimethoxypropane based mainly on MS and 1D and 2D NMR spectroscopic analyses.
Subject(s)
Iridoids , Chemistry , Magnetic Resonance Spectroscopy , Mass Spectrometry , Plant Roots , Chemistry , Scrophularia , ChemistryABSTRACT
A new oleanane-type triterpenoid glycoside, 3beta-O-(f-D-xylopyranosyl-(1-->2)-[beta-D-glucopyranosyl (1-->4)-beta-D-glucopyranosyl-(1 -->3)]-beta-D-fucopyranosyl-11, 13(18) diene-olean-23alpha, 28 diol (1), along with three known phenylethyl glycosides (2-4), was isolated from the root of traditional Chinese medicine Scrophularia ningpoensis. Among them, compounds 2 and 3 were obtained from Scrophularia genus for the first time. The structure of compound 1 was elucidated on the basis of spectroscopic method including 1D, 2D NMR and HR-ESI-MS.