OBJECTIVETo investigate the chemical constituents of Potentilla multifida.

METHODVarious chromatographic techniques were employed for isolation and purification of the constituents. The structures were elucidated by spectral analysis.

RESULTFour megastigmane glycosides were isolated from P. multifida and their structures were identified as citroside A (1), icariside B1 (2), (6S,7E,9R)-roseoside (3), (6S,7E,9R)-vomifoliol-9-O-beta-D-xylopyranosyl-(1-->6)-O-beta-D-glucopyranoside (4), respectively.

CONCLUSIONAll compounds were obtained from the genus Potentilla for the first time.

Glycosides ; chemistry ; isolation & purification ; Molecular Structure ; Norisoprenoids ; chemistry ; isolation & purification ; Plants, Medicinal ; chemistry ; Potentilla ; chemistry

Taking application of some isolation and purification technologies, such as solvent extraction, preliminary solvent isolation, column chromatographies over silica gel and Sephadex LH-20 gel and preparative HPLC, 10 compounds were obtained from Gynura nepalensis cultivated in the suburban area of Beijing. Their structures were identified by spectroscopic methods and comparison with literature as (3R) -3-hydroxy-β-ionone (1), (3S,5R, 6S, 7E) -5, 6-epoxy-3-hydroxy-7-megastigmen-9-one (2), (+) -boscialin (3), 3, 6-trans-3-hydroxy-α-ionone (4), 3, 6-cis-3-hydroxy-α-ionone (5), 3, 4-cis-3, 4-dihydroxy-β-ionone (6), ethyl caffeate (7), loliolide (8), 1H-indole-3-carbaldehyde (9), and 3-(hydroxyacetyl)indole (10), respectively. All compounds were isolated from the title plant for the first time, and with compounds 1, 2, 4-7, 9 and 10 being isolated from Gynura species for the first time. Structurally, the above compounds 1-6 belong to C13 nor-sesquiterpenoids, sharing the same carbon skeleton of megastigmane. According to this study, they are one of major kinds of chemical constituents of Gynura nepalensis and have important reference value for the investigation on phytotaxonomy of this species.
Asteraceae ; chemistry ; Caffeic Acids ; chemistry ; Cyclohexanones ; Drugs, Chinese Herbal ; chemistry ; Glucosides ; Indoles ; chemistry ; Mass Spectrometry ; Molecular Structure ; Norisoprenoids ; chemistry

Two new sulfated sesquiterpenoids, megastigman-7-ene-3, 5, 6, 9-tetrol-3-O-β-D-6'-sulfonated-glucopyranoside (1) and 3-O-β-D-6'-sulfonated-glucopyranosyl-6-(3-oxo-2-butenylidenyl)-1, 1, 5-trimethylcyclohexan-5-ol (2), along with one known sesquitepenoid compound icariside B1 (3) were isolated from the whole herb of Petasites tricholobus Franch. Their structures were identified by their chemical and spectroscopic characters. All obtained compounds were tested for their cytotoxicity against four cancer cell lines.
Cell Line, Tumor ; Glycosides ; isolation & purification ; pharmacology ; Humans ; Norisoprenoids ; isolation & purification ; pharmacology ; Petasites ; chemistry ; Sesquiterpenes ; isolation & purification ; pharmacology

OBJECTIVETo study the constituents of Hypericum attenatum.

METHODThe compounds were isolated by chromatography on silica gel, the structures were identified by their physical, chemical properties and IR, NMR and MS spectral data respectively.

RESULTNine compounds were isolated and identified as p-hydroxybenzoic acid (1), 6, 9-dihydroxy-4, 7-megastigmadien-3-one (2), butyl alcohol-O-alpha-D-fructoside (3), 24-ethyl-cholest-7-ene-3 beta, 5 alpha, 6 beta-thtroil (4), hexanol (5), 1 beta, 6 alpha-dihydroxyeudesmane-4(14)-ene (6), beta-sitosterol (7), 5, 5-dimethyl-4-hydroxy-tetrahydrofuran-2-one (8), beta-daucosterol (9).

CONCLUSIONAll of the compounds were isolated from H. attenuatum for the first time.

Hexanols ; chemistry ; isolation & purification ; Hypericum ; chemistry ; Norisoprenoids ; chemistry ; isolation & purification ; Parabens ; chemistry ; isolation & purification ; Plant Components, Aerial ; chemistry ; Plants, Medicinal ; chemistry

The present study was designed to determine the chemical constituents and identify new components of the leaves of Aquilaria sinensis (Lour.) Gilg. The compounds were isolated and purified by repeated silica gel, Sephadex LH-20, and ODS column chromatography and their structures were elucidated by NMR and HR-ESI-MS spectrometry. Eight megastigmane glycosides and two cucurbitacins were isolated and identified as (9S) megastigma-4,7-diene-2,3,9-triol 9-O-β-D-glucopyranoside (1), (9S) megastigma-4(13),7-diene-3,6,9-triol 9-O-β-D-glucopyranoside (2), macarangloside D (3), corchoionoside C (4), staphylionoside H (5), (+) 3-oxo-α-ionol-β-D-glucopyranoside (6), (-) 3-oxo-α-ionol-β-D-glucopyranoside (7), citroside B (8), 2-O-β-D-glucopyranosyl cucurbitacin I (9), bryoamaride (10). Compounds 1 and 2 were newly identified megstigmane glucosides and reported from this genus for the first time.
Chromatography, Liquid ; Cucurbitacins ; chemistry ; Cyclohexanones ; chemistry ; Glucosides ; chemistry ; isolation & purification ; Magnetic Resonance Spectroscopy ; Norisoprenoids ; chemistry ; isolation & purification ; Plant Leaves ; chemistry ; Thymelaeaceae ; chemistry

AIM: To study the chemical constituents of the aerial parts of Cirsium setosum (Willd.) MB.. METHODS: The chemical constituents were isolated and purified by various chromatographic techniques. Their structures were determined on the basis of physical properties and spectroscopic data. RESULTS: A new megastigmane glycoside and six known compounds were obtained and identified as (7E, 9R)-9-hydroxy-5, 7-megastigmadien-4-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyanoside (1), (6R, 7E, 9R)-9-hydroxy-4, 7-megastigmadien-3-one-9-O-α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside (2), urolignoside (3), 4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8-O-4$\prime $-neolignan-7-O-β-D-glucopyranoside (4), citroside A (5), salidrosidin (6), and adenosine (7). CONCLUSION Compound 1 is a new megastigmane glycoside, named as Xiaojiglycoside A.
Cirsium ; chemistry ; Cyclohexanones ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Molecular Structure ; Norisoprenoids ; chemistry ; isolation & purification ; Plant Components, Aerial ; chemistry

OBJECTIVETo study the chemical constituents from Hypericum perforatum.

METHODCompouds were isolated by chromatographic techniques. Their structures were identified by spectral methods. The inhibitory activity of recombinant human PTP1B was evaluated.

RESULTNine compounds were elucidated as D-Mannitol (1), 1,2-benzenedicarboxylic acid bis(1-methylpropyl) ester (2), (7E, 6R,9S)-9-hydroxy-4,7-megastigmadien-3-one (3), (6S,9R)-roseoside (4) , 2,6-dimethoxy-4-hydroquinone-l-O-beta-D-glucopyranoside (5), 2,6-di-methoxy-4-hydroxybenzyl alcohol 1 -O-beta-D-glucopyranoside (6), syringate 4-O-beta-glucopyranoside (7), hypericin (8), skyrin-6-0-beta-D-glucopyranoside (9) , (R)-2,3-dihydroxypropyl 3,4-dihydroxy-benzoate (10). At a concentration of 2 micromol x L(-1), compound 8 inhibited recombinant human PTP1B with inhibitory rate of 96.4% and IC50 of 2.5 micromol x L(-1).

CONCLUSIONcompound 10 was new, compounds 2-4, 7 were obtained from Hypericum for the first time and compounds 5-6 was isolated from this plant for the first time. Compound 8 showed remarkable PTP1B inhibitory activity.

Anthraquinones ; chemistry ; isolation & purification ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; Hypericum ; chemistry ; Molecular Structure ; Norisoprenoids ; chemistry ; isolation & purification

OBJECTIVETo investigate the chemical constituents of the red alga Gymnogongrus flabelliformis Harv.

METHODCompounds were isolated by normal phase silica gel and Sephadex LH - 20 gel column chromatography and reverse phase HPLC. Their structures were elucidated by spectroscopic methods including MS, 1H-NMR, 13C-NMR. Cytotoxicity of the compounds was screened by using standard MIT method.

RESULTFive compounds were isolated from G. flabelliforrmis, their structures were identified as(3S, 6R, 7E)-( + )-3-hydroxyl-4, 7-mega-stigmadien-9-one (1), (3S, 5R, 6S, 7E)-(-)-3-hydroxy-5, 6-epoxy-7-megastigmene-9-one (2), (3S, 5S, 6R, 7E)-(+)3-hydroxy-5, 6-epoxy-7-megastigmene-9-one (3), dehydrovomifoliol (4), (3R)-(-)4-[(2R, 4S)-4-acetoxy-2-hydroxy-2, 6, 6-trimethylcyclohexylidene] -3-buten-2-one (5).

CONCLUSIONAll of the compounds were obtained from this species for the first time and compound 1 was a new natural product. These compounds were inactive (IC50 > 10 microg x mL(-1)) in the MTT assay against several human cancer cell lines.

Antineoplastic Agents ; chemistry ; isolation & purification ; pharmacology ; Butanols ; chemistry ; isolation & purification ; pharmacology ; Cell Line, Tumor ; Cell Survival ; drug effects ; Chromatography, High Pressure Liquid ; Cyclohexanones ; chemistry ; isolation & purification ; pharmacology ; Humans ; Inhibitory Concentration 50 ; Magnetic Resonance Spectroscopy ; Norisoprenoids ; chemistry ; isolation & purification ; pharmacology ; Rhodophyta ; chemistry

The present study was designed to investigate the chemical constituents of the whole herb of Dichrocephala benthamii. A new megastigmane glucoside (compound 1), together with its four known analogues (compounds 2-5), was obtained. Their structures were elucidated on the basis of spectroscopic analyses (UV, IR, MS, and 1D and 2D NMR). The absolute configuration of compound 1 was assigned on the basis of CD method and chemical evidence. In addition, their cytotoxicity against human hepatoma cells (HepG-2) was evaluated by the MTT method. Compound 5 showed weak activity against HepG-2, while the other compounds did not show remarkable inhibitory effects.
Antineoplastic Agents, Phytogenic ; chemistry ; isolation & purification ; pharmacology ; Asteraceae ; chemistry ; China ; Cyclohexanones ; chemistry ; isolation & purification ; pharmacology ; Drug Screening Assays, Antitumor ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; Glucosides ; chemistry ; isolation & purification ; pharmacology ; Hep G2 Cells ; Humans ; Molecular Structure ; Norisoprenoids ; chemistry ; isolation & purification ; pharmacology ; Plants, Medicinal