Thirteen steroids(1-13) were isolated from the non-alkaloid constituents of Uncaria rhynchophylla by column chromatography on silica gel, ODS, Sephadex LH-20, and preparative HPLC chromatography, and their structures were elucidated by analyses of the MS and NMR spectral data. All the compounds were isolated from the genus Uncaria for the first time, and 1 was a new compound. The ~1H-NMR and ~(13)C-NMR data of two compounds(12 and 13) in deuteron-chloroform were completely assigned. This study enriched the steroid constituents of U. rhynchophylla and provided scientific references for the elucidation of active constituents and further development and utilization of U. rhynchophylla.
Chromatography, High Pressure Liquid ; Steroids ; Uncaria/chemistry*

To study the oxidative alkaline-degradation products of PQS (Panax quinquefolium saponin), two compounds were isolated from the crude product of oxidative alkaline-degradation by silica gel column chromatography, Sephadex LH-20 column chromatography and recrystallized methods. On the basis of spectroscopic analysis, their structures were established as (12R, 20S, 24R)-20, 24; 12, 24-diepoxy-24-deisopropyl-dammarane-3beta-ol (1) and (20S, 24R)-20, 24-epoxydammarane-3beta3, 12beta, 25-triol (2). Compounds 1 and 2, dammarane type triterpene with cyclization at the side chain, were obtained for the first time from alkaline-degradation products of total ginsenosides of Panax quinquefolium L., compound 1 is a new compound.
Cyclization ; Oxidation-Reduction ; Panax ; chemistry ; Sapogenins ; chemistry ; Saponins ; chemistry ; Steroids ; chemistry ; Triterpenes ; chemistry

AIMTo study compounds isolated from Picria fel-terrae.

METHODSThe chemical constituents were separated and purified by column chromatography on silica gel and MCI. Their structures were identified on the basis of spectral data (IR, UV, MS, ID NMR and 2D NMR).

RESULTSA new cucurbitacin, along with a known one, were obtained from the 60% EtOH extract of the whole plant.

CONCLUSIONThe new compound was identified as 11, 24-dioxo-5, 21-diene-cucurbit-3alpha-O-beta-D-xylopyranosyl-16alpha-O-alpha-L-rhamnopyranoside (dehydrobryogenin glycoside). The known one, hexanorcucurbitacin F, was obtained for the first time from Picria fel-terrae.

Molecular Structure ; Plants, Medicinal ; chemistry ; Saponins ; chemistry ; isolation & purification ; Scrophulariaceae ; chemistry ; Steroids ; chemistry ; isolation & purification

OBJECTIVETo study the steroidal alkaloids in Veratrum dahuricum.

METHODThe compounds were isolated and purified by various column chromatographic methods. Their structures were identified by spectroscopic analysis.

RESULTFive compounds were isolated and identified as (20R, 22S, 25S)-veratra-5,13-dien-3beta-ol (1), angeloylzygadenine (2), 15-O-(2-methylbutanoyl)-3-O-veatroylprotoverine (3), 20-isoveratramine (4), veratramine (5).

CONCLUSIONCompound 1 was a new compound, compounds 24 were obtained from the plant for the first time.

Alkaloids ; chemistry ; Drugs, Chinese Herbal ; chemistry ; Isomerism ; Steroids ; chemistry ; Veratrum ; chemistry

Five new saponins, including three steroid saponins, paristenoids A-C (1-3), and two triterpenoid saponins, paristenoids D-E (4-5), along with four known ones (6-9) were isolated from the rhizomes of Paris polyphylla var. stenophylla. The structures of the isolated compounds were identified mainly by detailed spectroscopic analysis, including extensive 1D and 2D NMR, MS, as well as chemical methods. Compound 3 is a new cyclocholestanol-type steroidal saponin with a rare 6/6/6/5/5 fused-rings cholestanol skeleton, and this skeleton has been first found from the genus Paris. The cytotoxicities of the isolated compounds against three human three glioma cell lines (U87MG, U251MG and SHG44) were evaluated, and compound 7 displayed certain inhibitory effect with IC₅₀ values of 15.22 ± 1.73, 18.87 ± 1.81 and 17.64 ± 1.69 μmol·L^-1, respectively.
Humans ; Rhizome/chemistry* ; Steroids/chemistry* ; Liliaceae/chemistry* ; Saponins/chemistry* ; Triterpenes/analysis*

OBJECTIVETo isolate and identify the steroids in Sedum lineare.

METHODThe steroids were isolated by column chromatography, semi-preparative thin layer chromatography and related techniques, their structures were elucidated through spectroscopic analyses.

RESULTSix steroids were isolated and identified as stigmast-7-en-3beta-ol (1), stigmast-3beta,5alpha,6beta-triol (2), stigmast-5-en-3beta-ol-7-one (3), stigmast-5-en-3beta,7alpha-diol (4), stigmast-5-en-3beta,7beta-diol (5), beta-sitosterol (6).

CONCLUSIONCompounds 1-5 were isolated from this plant for the first time.

Plant Extracts ; analysis ; Sedum ; chemistry ; Steroids ; analysis ; isolation & purification

From an ethanol extract of Euphorbia micractina roots, seven steroids fifteen aromatic derivatives were isolated by a combination of various chromatographic techniques, including column chromatography over macroporous resin, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were elucidated by spectroscopic data analysis as stigamast-5-ene-3beta, 7alpha-diol(1), stigamast-5-ene-3beta,7beta-diol(2), stigmast-5-en-3beta-ol-7-one(3), stigmast-4-en-6beta-ol-3-one(4), stigmast-1, 4-dien-3-one(5), stigmast-3,6-dione(6), beta-sitosterol(7), scopoletin(8), aesculetin(9), 6-hydroxy-5,7-dimethoxycoumarin(10), quercetin(11), 3,3', 4'-tri-O-methylellagic acid(12), p-hydroxyphenylethyl anisate(13), m-hydroxyphenylethyl alcohol(14), (E)-cinnamic acid(15), (E)-ferulic acid(16), 3,4-dihydroxybenzoic acid(17), vanillic acid(18), p-hydroxybenzoic acid(19), ethyl 3,4-dihydroxybenzoate (20), ethyl gallate(21), and methyl gallate(22). These compounds were obtained from this plant for the first time.
Drugs, Chinese Herbal ; chemistry ; Euphorbia ; chemistry ; Molecular Structure ; Spectrometry, Mass, Electrospray Ionization ; Steroids ; chemistry

OBJECTIVETo study the chemical constituents of Monascus purpureus metabolite.

METHODThe compounds were isolated by column chromatography methods, and their structures were determined by spectroscopic methods.

RESULTEight compounds were isolated from the petroleum ether fraction of ethanolic extract and elucidated as stigmast-4-en-3-one (1), 3-oxo-24-methylenecycloarane (2), stigmasterol (3), 7beta-hydroxystigmasterol (4), 3beta-hydroxystigmast-5-en-7-one (5), 3beta-hydroxystigmast-5,22-dien-7-one (6), 5alpha, 8alpha-epidioxyergosta-6,22-dien-3beta-ol (7), sitosterol (8).

CONCLUSIONAll of the compounds were isolated from this genu for the first time except compound 3 and 7.

Drugs, Chinese Herbal ; chemistry ; isolation & purification ; metabolism ; Monascus ; chemistry ; metabolism ; Steroids ; chemistry ; isolation & purification ; metabolism

Cynanchum is one of the most important genera in Asclepiadaceae family, which has long been known for its therapeutic effects. In this genus, 16 species are of high medicinal value. The extracts of the root and/or rhizome parts have been applied in traditional Chinese medicines (TCM) for the prevention and treatment of various illnesses for centuries. C21 steroids, as the typical constituents of Cynanchum species, possess a variety of structures and pharmacological activities. This review summarizes the comprehensive information on phytochemistry and pharmacology of C21 steroid constituents from Cynanchum plants, based on reports published between 2007 and 2015. Our aim is to provide a rationale for their therapeutic application, and to discuss the future trends in research and development of these compounds. A total of 172 newly identified compounds are reviewed according to their structural classifications. Their in vitro and in vivo pharmacological studies are also reviewed and discussed, focusing on antitumor, antidepressant, antifungal, antitaging, Na(+)/K(+)-ATPase inhibitory, appetite suppressing and antiviral activities. Future research efforts should concentrate on in vitro and in vivo biological studies and structure activity relationship of various C21 steroid constituents.
Animals ; Cynanchum ; chemistry ; Humans ; Molecular Structure ; Plant Extracts ; chemistry ; pharmacology ; Steroids ; chemistry ; pharmacology

To study the chemical constituents of Dioscorea zingiberensis Wright, the EtOH extract of fresh rhizomes of D. zingiberensis was concentrated and partitioned further to produce petroleum ether-, ethylacetate-, n-butanol- and water-soluble fractions. The water-soluble fraction was subjected to column chromatography on macro resin AB-8, and the final products were obtained by repeated reversed-phase ODS and MCI gel CHP 20P column chromatography. Structures of compounds were elucidated by means of 1H NMR, 13C NMR, 135DEPT, HMQC, HMBC and TOCSY spectroscopic analyses. Five steroidal saponins were isolated, in which one new steroidal saponin was identified as (25R)-26-O-(beta-D-glucopyranosyl) -furost-5-en-3beta, 22xi, 26-triol-4beta-acetoxyl-3-O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopy ranosyl-(1-->4)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-glucopyranoside (V). The compound V is a new compound, named as zingiberenin G. The compounds I, II and III were reported for the first time from D. zingiberensis Wright.
Dioscorea ; chemistry ; Molecular Structure ; Plants, Medicinal ; chemistry ; Rhizome ; chemistry ; Saponins ; chemistry ; isolation & purification ; Steroids ; chemistry ; isolation & purification