Characterization of the Triterpene Saponins of the Roots and Rhizomes of Blue Cohosh (Caulophyllum Thalictroides)

Abstract

Seven triterpene saponins were isolated from n-butanol fractions of blue cohosh (Caulophyllum thalictroides) roots and rhizomes. Their structures were established by spectral ((1)H NMR, (13)C NMR, 2D-NMR, and APCI-MS) techniques and chemical reactions as hederagenin 3-O-alpha-L-arabinopyranoside (1); caulophyllogenin 3-O-alpha-L-arabinopyranoside (2); hederagenin 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranoside (3); 3-O-alpha-L-arabinopyranosyl-hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (4); 3-O-alpha-L-arabinopyranosyl- caulophyllogenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (5); 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl- echinocystic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (6); 3-O-beta-D-glucopyranosyl-(1-->2)-alpha-L-arabinopyranosyl-hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl(1-->6)-beta-D-glucopyranoside (7). All seven compounds were identified in this species for the first time.

Biochemical analysis of a multifunctional cytochrome P450 (CYP51) enzyme required for synthesis of antimicrobial triterpenes in plants

“…This result suggests a chemical formula of C 30 H 50 O 3 and is consistent with the previously obtained GC-MS data. The 1 H and 13 C NMR spectra of the purified compound were compared with available NMR data for β-amyrin (34,35). Characteristic signals for the olefinic carbons in β-amyrin (C12 δ 123; C13 δ 145) (34) were missing in the 13 C NMR spectrum of the analyzed compound, indicating the loss of the double bond.…”

“…The 1 H and 13 C NMR spectra of the purified compound were compared with available NMR data for β-amyrin (34,35). Characteristic signals for the olefinic carbons in β-amyrin (C12 δ 123; C13 δ 145) (34) were missing in the 13 C NMR spectrum of the analyzed compound, indicating the loss of the double bond. Further distortionless enhancement by polarization transfer, heteronuclear multiple bond correlation, and selective NOE experiments revealed an epoxide between C12 and C13 and a hydroxyl group attached to C16, leading to the identification of the compound as 12,13β-epoxy-3β,16β-dihydroxy-oleanane (12,13β-epoxy-16β-hydroxy-β-amyrin) ( Fig.…”

Triterpenoid Saponins from the Roots of <i>Clematis uncinata</i>

“…The NMR data of 2 assigned to the aglycone part were the same as those of hederagenin. 18) Acid hydrolysis of 2 also afforded D-glucose, D-ribose, L-arabinose and L-rhamnose. Comparison of the NMR data of the sugar units in 2 with those of 1 revealed that they were very similar, suggesting that 2 possessed the identical oligosaccharide chains to 1.…”

“…The 50% EtOH and 70% EtOH eluates were further purified by repeated column chromatography over middle chromatogram isolated (MCI) gel, octadecyl silica (ODS), silica gel and preparative HPLC to afford eight new bisdesmosidic triterpenoid saponins (1)(2)(3)(4)(5)(6)(7)(8), named as clematiunicinosides A-H, as well as eleven known ones (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19).…”

“…The plant Clematis uncinata is mainly distributed in southern China, such as Guizhou, Zhejiang, Fujian, Guangdong and Guangxi provinces. 13) The blank in chemical constituent, the potential medicinal importance and our interest in the chemistry of saponins prompted us to carry out a phytochemical investigation on this plant, which led to the isolation of eight new bisdesmosidic triterpenoid saponins, clematiunicinosides A-H (1-8), together with eleven known ones (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). In addition, the cytotoxic effects of the isolated triterpenoid saponins on Caski cells were evaluated.…”