Chemical constituents from the roots of <Emphasis Type="Italic">Polygonum bistorta</Emphasis>

Investigation of the roots of Polygonum bistorta L. afforded seven compounds including five triterpenoids, a coumarin, and a steroid, the structures of which were identified by EIMS, ¹H NMR, ¹³C NMR, DEPT, and HMBC experiments. All the compounds have been isolated from Polygonum genus for the first time. Published in Khimiya Prirodnykh Soedinenii, No. 5, pp. 463–465, September–October, 2007.     

New bioactive triterpenoid from Oldenlandia cantonensis How

A new pentacyclic triterpenoid, urs-12-en-29α-oic acid-3β-ol (1), was obtained from the ethanol extract of Chinese herb Oldenlandia cantonensis How. The structure was elucidated by spectroscopy methods, including nuclear magnetic resonance (NMR) (1D and 2D), infrared spectroscopy (IR), and mass spectrometry (MS). 1 exhibited significant inhibitory activity against the human DNA topoisomerase I (hTopo I), the cancer cell lines BEL-7402 and MCG-803, with the IC₅₀ values 12.0, 6.5, and 8.0 μg/mL, respectively. The volatile oil, the fraction of petroleum ether: EtOAc = 20:1 (V/V) on Si gel chromatography, was also quantitatively analyzed by gas chromatography mass spectrometry (GC-MS). As a result, 60 compounds were identified. Among them, the long chain aliphatics, terpenes and steroids, as the representative structure type, were found with percentages of 36.16%, 6.42% and 9.28%, respectively. Translated from Chinese Journal of Applied Chemistry, 2006, 23(8): 871–874 [译自: 应用化学]     

A New Triterpenoid Saponin and a New Glycoside from Epigynum aurilum

A new triterpenoid saponin with novel sugar moiety (1), a new trisaccharide derivative (2), as well as a known monosaccharide derivative (3), were isolated from the dried stem of Epigyhum aurilum. The structures of compounds 1 and 2 were determined by MS and NMR spectram analyses.     

3β-Methoxyolean-18-ene (miliacin) from the marine fungus Chaetomium olivaceum

A pentacyclic tritepenoid, 3-methoxyolean-18-ene (miliacin), was isolated for the first time from the marine fungus Chaetomium olivaceum. Its structure was determined on the basis of 2D NMR spectroscopy and X-ray diffraction data.     

A New Triterpenoid from "Gualou-xiebai-baijiu-tang" Consisting of Fructus trichosanthis and Bulbus allii mtacrostemi

A new triterpenoid saponin was isolated by bioactivity-guided isolation from "Gualou-xiebai-baijiu-tang" consisting ofFructus trichosanthisi and Bulbus allii macrostemi. Its structure was determined as 3-O-β-D-galactopyranosyl-hederagenin 28-O-β-D-xylopyranosyl (1→6)- β-D-galactopyranosyl ester by means of chemical evidences and spectral analysis.     

Arjunolic acid derivative glycoside from the stems of <Emphasis Type="Italic">Hedera colchica</Emphasis>

Five triterpenoid saponins were isolated from the stems of Hedera colchica K. Koch, Araliaceae. Two of them are new natural substances. HCSt-A (1): 3-O--D-arabinopyranoside; 28-O--L-rhamnopyranosyl-(1 4)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-arjunolic acid. HCSt-B (2): 3-O--D-xylopyranoside; 28-O--L-rhamnopyranosyl-(14)-O--D-glucopyranosyl-(16)-O--D-glucopyranosyl-hederagenin. The derivative of arjunolic acid is described for the first time in Araliaceae family. The chemical structures of isolated compounds were established on the base of chemical and 1D and 2D NMR experiments.Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 461–463, November–December, 2004.This revised version was published online in April 2005 with a corrected cover date.     

Two new triterpenoids from Gardenia jasminoides fruits

A new cycloartane triterpenoid, named gardenolic acid C (1), a new ursane triterpenoid, named 3β,16β,21β,23,24-pentahydroxy urs-12,18,20-trien-28-oic acid γ-lactone (2), together with three know triterpenoids, gardenolic acid A (3), gardenolic acid B (4), and 3α,16β,23,24-tetrahydroxy-28-nor-ursane-12,17,19,21-tetraen (5) were isolated from the fruits of Gardenia jasminoides Ellis. The structures of these compounds were elucidated by analyses of spectroscopic data. All isolates were evaluated for their neuroprotective effects in vitro.

     

A new cucurbitane triterpenoid from Momordica charantia

One new cucurbitane-type triterpenoid saponin, 5b,19-epoxycucurbita-6,23-diene-3b,19,25-triol-3-O-b-D-allopyranoside (1), named momordicoside P was isolated from the fresh fruits of Momordica charantia. The structure of the saponin was elucidated byspectral methods, including 2D-NMR spectra.     

Tirucallane Triterpenoid Saponins from Munronia delavayi Franch

Four new tirucallane triterpenoid saponins, named munronosides I–IV ( 2 – 5 ), along with three known triterpenoids, sapelin B ( 1 ), melianodiol, and (3β)‐22,23‐epoxytirucall‐7‐ene‐3,24,25‐triol, were isolated from the EtOH extract of the whole plants of Munronia delavayi Franch by chromatographic methods. On the basis of spectroscopic evidences, the structures of 2 – 5 were elucidated as (20S,23R,24S)‐21,25‐epoxy‐29‐{{O‐β‐d‐ glucopyranosyl‐(1→3)‐O‐[α‐l‐ rhamnopyranosyl‐(1→6)]‐β‐d‐ glucopyranosyl}oxy}‐23,24‐dihydroxytirucall‐7‐ene‐3,21‐dione ( 2 ), (3β,20S,23R,24S)‐21,25‐epoxy‐29‐{{O‐β‐d‐ glucopyranosyl‐(1→3)‐O‐[α‐l‐ rhamnopyranosyl‐(1→6)]‐β‐d‐ glucopyranosyl}oxy}‐3,23,24‐trihydroxytirucall‐7‐en‐21‐one ( 3 ), (20S,23R,24S)‐24‐(acetyloxy)‐21,25‐epoxy‐29‐{{O‐β‐d‐ glucopyranosyl‐(1→3)‐O‐[α‐l‐ rhamnopyranosyl‐(1→6)]‐β‐d‐ glucopyranosyl}oxy}‐23‐hydroxytirucall‐7‐ene‐3,21‐dione ( 4 ), and (3β,20S,23R,24S)‐24‐(acetyloxy)‐21,25‐epoxy‐29‐{{O‐β‐d‐ glucopyranosyl‐(1→3)‐O‐[α‐l‐ rhamnopyranosyl‐(1→6)]‐β‐d‐ glucopyranosyl}oxy}‐3,23‐dihydroxytirucall‐7‐en‐21‐one ( 5 ).     

Novel biotransformation of pentacyclic triterpenoid acids by Nocardia sp. NRRL 5646

Six pentacyclic triterpene acids, ursolic acid, oleanolic acid, betulinic acid, 23-hydroxybetulinic acid, glycyrrhetinic acid, and senegenin, were metabolized by the microbe Nocardia sp. NRRL 5646 to selectively furnish their corresponding 28-methyl esters. Notably, ursolic acid (1) was converted to oleanolic acid methyl ester (4) via two intermediates, oleanolic acid (2), and ursolic acid methyl ester (3), which are formed by participation of ‘retro-biosynthetic’ methyl migration from C-19 to C-20. Senegenin (11) was selectively converted to a nortriterpene methyl ester, senegenic acid methyl ester (12), via an unprecedented C-C bond cleavage. The stereochemical assignments of compounds 11 and 12 were made unambiguously for the first time using 2D NMR spectroscopy.