By using a combination of various chromatographic techniques including column chromatography over silica gel and Pharmadex LH-20 and reversed-phase HPLC, two minor new compounds, labda-12, 14-dien-6beta, 7alpha, 8beta, 17-tetraol (1), 2, 3-cis-6-acetyl-5-hydroxy-2-(hydroxymethylvinyl)-2, 3-dihydrobenzofuran-3-ol angelate (2), and a minor new natural product 6-methoxy-4-methyl-3, 4-dihydro-2H-naphthalen-1-one (3) have been isolated from an ethanolic extract of Heteroplexis micocephala. Their structures were elucidated with spectroscopic data analysis including 2D NMR experiments.

Fifteen compounds were isolated from the stem (with skin removed) of Sinocalamus affinis by a combination of various chromatographic techniques including silica gel, macroporous adsorbent resin, Sephadex LH-20, and preparative HPLC. Their structures were elucidated by spectroscopic data as ( + )-(1S, 2R)-1, 2-bis (4-hydroxy- 3-methoxyphenyl)-1, 3-propanediol (1), threo-guaiacylglycerol-beta-O-4'-coniferyl ether(2), erythro-guaiacylglycerol-beta-O-4'-coniferyl ether(3), ( + )-(7S, 8R, 8'R)-5'-methoxylariciresinol(4), ( + )-(7S, 8R, 8'R)-5, 5'-dimethoxylariciresinol (5), ( +/- )-glaberide I (6), ( - )-syringaresinol (7), ( - )-medioresinol(8), ( - )-(8R, 8R')-4, 4'-dihydroxy-3, 3', 5, 5'-tetramethoxyligna-9, 9'-diol(9), ( - )-secoisolariciresinol-9, 9'-acetonide (10), and ( + )-lyoniresinol (11); a new natural product 2, 6-dimethoxypyran4-one (12), and beta-sitosterol, 4-hydroxycinnamic acid, and 2, 6-dimethoxy-p-benzoquinone. These compounds were isolated from the genus Sinocalamus for the first time, compound 10 should be an artifact.
Chromatography ; methods ; Drugs, Chinese Herbal ; chemistry ; Lignans ; chemistry ; isolation & purification ; Medicine, Chinese Traditional ; Plant Stems ; chemistry ; Poaceae ; chemistry

OBJECTIVETo investigate the chemical constituents of tuber of Gymnadenia conopsea.

METHODThe constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis.

RESULTThirty-four compounds were isolated. Their structures were identified as six 2-isobutyltartrate benzyl ester glucosides: coelovirin A (1), coelovirin B (2), coelovirin E (3), coelovirin D (4), dactylorhin B (5) and loroglossin (6). Three 2-isobutylmalate benzyl ester glucosides: dactylorhin A (7), dactylorhin E (8) and militarine (9). Three lignans: arctigenin (10), lappaol A (11) and lappaol F (12). Six aromatic acid (alhyde or alcohol) derivatives: 4-beta-D-glucopyranosyloxyl-trans-phenylpropenoic acid (13), 4-beta-D-glucopyranosyloxyl-cis-phenylpropenoic acid (14), gastrodin (15), 4-beta-D-glucopyranosyloxylphenylaldehyde (16), 4-beta-D-glucopyranosyloxylbenzyl methyl ether (17), 4-beta-D-glucopyranosyloxyloxylbenzyl ethyl ether (18), and bis(4-hydroxybenzyl) ether mono 4-O-beta-D-glucopyranoside (19). Four cyclodipeptides: cyclo(L-Leu-L-Tyr) (20), cyclo(L-Leu-L-Pro) (21), cyclo(L-Val-L-Tyr) (22), and cyclo(L-Ala-D-Phe) (23). One N6-substituted andenosine: N6-(4-hydroxybenzyl)-adenine riboside (24). An aromatic amide: N-trans-feruloyltyramine (25). Nine aromatic acids (or aldehyde or alcohol): 3-hydroxybenzoic acid (26), 4-hydroxyisophthalic acid (27), 4-hydroxybenzyl alcohol (28), 4-hydroxybenzyl methyl ether (29), 4-hydroxybenzylaldehyde (30), 4-hydroxybenzoic acic (31), 4-hydroxy-3-methoxybenzoic acid (32), trans-p-hydroxyphenylpropenoic acid (33), and cis-p-hydroxyphenylpropenoic acid (34). At a concentration of 1.0 x 10(-6) mol x L(-1), compounds 10-12 showed antioxidative activity inhibiting Fe(+2) -cystine induced rat liver microsomal lipid peroxidation with inhibitory rates of 53%, 59%, and 52%, respectively(positive control VE with 35% inhibition).

CONCLUSIONThese compounds were obtained from the genus Gymnadenia for the first time except for 5-7, 9, 15, 28-34. Compounds 10-12 possess antioxidant activity.

Animals ; Lipid Peroxidation ; drug effects ; Microsomes, Liver ; drug effects ; metabolism ; Orchidaceae ; chemistry ; Plant Extracts ; analysis ; isolation & purification ; pharmacology ; Rats

Twenty-one compounds were isolated from an ethanol extract of Machilus wangchiana by a combination of various chromatographic techniques including column chromatography over silica gel and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic data analysis including optical rotation, UV, IR, MS, and NMR data. The compounds are categorized as eight butanolides (1-8), eight lignans (9-16), and five terpenoids (17-21). Compound 16 is a new natural product with an uncommon heptanorlignan skeleton. Meanwhile, the unique Ginkgo biloba (maidenhair) metabolites ginkgolides A (19) and ginkgolides B (20) were obtained from this material. In the preliminary assays, compound 5 showed selective inhibitory activities against human stomach cancer cells (BGC-823) and ovary cancer cells (A2780) with IC50 values of 0.13 x 10(-6) and 2.66 x 10(-6) mol x L(-1), respectively. Compounds 8 and 9, at 1 x 10(-5) mol x L(-1), showed inhibitory activities against the release of beta-glucuronidase of the polymorphous nuclear leukocytes induced by platelet activating factor (PAF), with inhibition rates of 60.0% and 54.2%.
Cell Line, Tumor ; Cell Proliferation ; drug effects ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Humans ; Inhibitory Concentration 50 ; Lauraceae ; chemistry ; Molecular Structure

Two new compounds (1 and 2), together with twenty-one known compounds (3-23), were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin, MCI gel, silica gel, and Sephadex LH-20 and reversed-phase HPLC. Their structures were identified by spectroscopic data analysis as 4-hydroxy-3-(4-hydroxybenzyl) benzyl methyl ether (1), 4-( methoxymethyl) phenyl-1-O-beta-D-glucopyranoside (2), hibicutaiwanin (3), 4-(4-hydroxybenzyl)-2-methoxyphenol (4), 4,4'-methylenebis(2-methoxyphenol) (5), L-phenyllactic acid (6) ,4-hydroxy-3-methoxybenzyl ethol ether (7), p-hydroxylbenzyl alcohol (8), p-hydroxylbenzyl methyl ether (9), p-hydroxylbenzyl ethyl ether (10), p-hydroxybenzaldehyde (11), p-hydroxybenzoic acid (12), p-hydroxybenzoic acid (13), gastrodin (14), 4-(ethoxymethyl) phenyl-1-O-beta-D-glucopyranoside (15), 4-(beta-D-glucopyranosyloxy) benzaldehyde (16), p-methylphenyl-1-O-beta-D-glucopyranoside (17 ), methyl-O-beta-D-glucopyranoside (18), 5-hydroxymethl-furan aldehyde (19), parishin (20), parishin B (21), parishin C (22), and diosgenin (23). The 13C-NMR data of compound 4 was first reported.
Drugs, Chinese Herbal ; chemistry ; Gastrodia ; chemistry ; Organic Chemicals ; analysis ; isolation & purification ; Water ; chemistry

OBJECTIVETo investigate the chemical constituents of Heteroplexis nicocephala.

METHODThe constituents were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Pharmadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. In vitro cytotoxic, neuroprotective, and anti-inflammatory activities were screened by using cell-based models.

RESULTSeventeen terpenoids were isolated. The structures were identified as two monoterpenoids: (-)-bomyl ferulate(1) and loliolide(2). Seven sesquiterpenoids: 1beta-hydroxy-alpha-cyperone(3) , alpha-rotunol(4), 10alpha-hydroxycadin-4-en-15-al (5), 1-epi-10beta-hydroxycadin-4-en-15-al(6), 10alpha-hydroxyisodauc-3-en-15-al(7), germacrene B(8), and mandassidione(9). Five diterpenoids: 12-epi-bacchotricuneatin A(10), 1-hydroxy-12-epi-bacchotricuneatin A(11), cleroinermin(12), desoxyarticulin(13), and anhydroolearin(14). And three triterpenoids: friedelin (15), ursolic acid(16), and obtusalin(17). In the in vitro assays, 1 showed selective cytotoxic activity against BGC-823, with an IC50 value of 8.00 x 10(-5) mol x L(-1). At a concentration of 1 x 10(-5) mol x L(-1), 12 showed neuroprotective activity against MPP+ induced PC12-syn cell damage, with a relative cell proliferation rate of 104.32% (P < 0.001). 2 exhibited inhibitory activity against the release of beta-glucuronidase from the polymorphous nuclear leukocytes induced by PAF, with an inhibitory rate of 52.7% (P < 0.05) at the same concentration.

CONCLUSIONCompounds 1-17 were obtained from the genus Heteroplexis for the first time. 1 showed selective cytotoxic activity against human gastric cancer cell lines (BGC-823), 12 and 2 showed potent neuroprotective and anti-inflammatory activities, respectively.

Anti-HIV Agents ; chemistry ; pharmacology ; Anti-Inflammatory Agents ; chemistry ; pharmacology ; Asteraceae ; chemistry ; Cell Line ; Cell Survival ; drug effects ; Diterpenes ; chemistry ; pharmacology ; HIV-1 ; drug effects ; Humans ; Molecular Structure ; Nuclear Magnetic Resonance, Biomolecular ; Sesquiterpenes ; chemistry ; pharmacology ; Terpenes ; chemistry ; pharmacology

OBJECTIVETo investigate the chemical constituents of Heteroplexis micocephal and their bioactivities.

METHODThe constituents were isolated by using a combination of various chromatographic techniques including column chromatography over macroporous adsorbent resin, silica gel, Pharmadex LH-20, and C-18, as well as reversed-phase HPLC. Structures of the isolates were identified by spectroscopic data analysis. In vitro cytotoxic, HIV-1 replication, neuroprotective, and anti-inflammatory activities were screened by using cell-based models.

RESULTThirty-one compounds were obtained. Twelve of them are phenylpropanols, and the structures were elucidated as (+)-(7S,8R)-guaiacylglycerol (1), ferulic acid (2), cinnamate methyl ester (3), 1-eicosanyl 3,4-dihydroxycinnamate (4), morinin B (5), sinapyl diangelate (6), chlorogenic acid (7), 4-O-caffeoylquinic acid (8), 5-O-caffeoylquinic acid (9), 5-O-caffeoylquinic acid methyl ester (10), 1,5-di-O-caffeoylquinic acid (11) and 4,5-di-O-caffeoylquinic acid methyl ester (12). Three lignans, (+)-pinoresinol (13), prinsepiol (14) and (+)-pinoresinol-O-beta-D-glucopyranoside (15). Four acetophenones, 2,4-diacetylanisole (16), espeleton (17), viscidone (18) and 12-hydroxytremetone-12-O-beta-D-glucopyranoside (19). Nine flavones, isosakuranetin (20), hesperetin (21), 3-methoxy-5,7,3',4'-tetrahydroxyflavone (22), acacetin (23), 5-hydroxy-7,4'- dimethoxyflavone (24), 7-methoxy-4',5, 6-trihydroxyflavone (25), 3,3'-dimethylquercetin (26), kaempferol 3-O-rutinoside (27), rutin (28). And three coumarins scopoletin (29), umbelliferone (30) and ayapin (31). Compound 6 and 22 showed selective cytotoxicities against a human stomach cancer cell line(BGC-823) and a human lung cancer cell line (A549) with IC50 values of 3.74 x 10(-5) and 7.17 x 10(-5) mol L(-1), respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication with an IC50 value of 4.04 x 10(-6) mol L(-1), while 22 showed neuroprotective activity Against the MPP+ induced PC12-syn cell damage, with a relative protection ratio of 105.2% (P < 0.01) at a concentration of 10(-5) mol L(-1). Compound 26 and 31 showed inhibitory activities against the release of beta-glucuronidase of the polymorphous nuclear leukocytes induced by platelet activating factor (PAF), with inhibitory rates of 75.6% (P < 0.001) and 53. 9% (P < 0.01), respectively.

CONCLUSIONCompounds 1-31 were obtained from the genus Heteroplexis for the first time. Compound 6 and 22 possessed selective cytotoxicities against human cancer cell lines BGC-823 and A549, respectively. In addition, Compound 6 showed a potent activity inhibiting HIV-1 replication while 22 showed neuroprotective activity against the MPP+ induced PC12-syn cell damage. Compound 26 and 31 were potent anti-inflammatory agents.

Animals ; Antiviral Agents ; analysis ; pharmacology ; Cell Line, Tumor ; HIV-1 ; drug effects ; physiology ; Humans ; Myrtaceae ; chemistry ; Neurons ; cytology ; drug effects ; Neuroprotective Agents ; analysis ; pharmacology ; Plant Extracts ; analysis ; pharmacology ; Rats ; Virus Replication ; drug effects

To study chemical constituents contained in ethanol extracts from roots of Machilus yaoshansis. Fifteen compounds were separated from the roots of M. yaoshansis by using various chromatographic techniques. Their structures were identified on the basis of their physicochemical properties and spectral data as twelve lignans(+)-guaiacin (1), kadsuralignan C (2), (+)-isolariciresinol (3), 5'-methoxy-(+)-isolariciresinol (4), (7'S, 8R, 8'R)-lyoniresinol (5), meso-secoisolariciresinol (6), isolariciresinol-9'-O-beta-D-xylopyranoside (7), 5'-methoxy-isolariciresinol-9'-O-beta-D-xylopyranoside (8), lyoniresinol-9'-O-beta-D-xylopyranoside (9), (2R, 3R) -2, 3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-3-methyl-5-(E)-propenylbenzofuran (10), 3, 5'-dimethoxy-4', 7-epoxy-8, 3'-neolignan-4, 9, 9'-triol (11), nectandrin B (12), and three flavanes(+)-catechin (13), (-)-epicatechin (14), and bis-8, 8'-catechinylmethane (15). All of the compounds 1-15 were separated from M. yaoshansis for the first time.
Butylene Glycols ; chemistry ; Catechin ; chemistry ; Lauraceae ; chemistry ; Lignans ; chemistry ; Lignin ; chemistry ; Naphthols ; chemistry ; Plant Roots ; chemistry

Twenty-one non-anthraquinones constituents were isolated for the first time from an ethanol extract of the roots of Knoxia valerianoides by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Their structures were identified by their physical-chemical properties and spectroscopic analysis including NMR and MS. The compounds include ten triterpenoids: ursolic acid (1), oleanolic acid (2), 2-oxo pomolic acid (3), pomolic acid (4), maslinic acid (5), rotungenic acid (6), tormentic accid (7), rotundic acid 3,23-acetonide (8), arjungenin (9), and 2alpha, 3beta, 19alpha, 23-tetrahydroxy-urs-12-en-28-oic acid (10), four sitosterones: (24R)-24-ethylcholesta-4,22-dien-3-one (11), 3-oxo-4-en-sitosterone (12), 7-oxostigmasterol (13), and 7-oxo-beta-sitosterol (14), two lignans: eudesmin (15) and ciwujiatone (16), one coumarin: cnidilin (17), and four simple aromatic analogues: 5-hydroxymethylenefural (18), 3-hydroxy-4-methoxybenzoic acid (19), benzoic acid (20), and 2-hydroxy-5-methxoycinnamaldehydes (21). In the in vitro assays against human cancer cell lines (HCT-8, Bel7402, BGC-823, A549, and A2780), against deserum and glutamate induced PC12-syn cell damage, and against HIV-1 replication, and inhibiting protein tyrosine phosphatase 1B (PTP1 B), LPS induced NO production in macrophage, and Fe(2+)-cystine induced rat liver microsomal lipid peroxidation, at a concentration of 1 x 10(-5) mol x L(-1), no compound showed activity.
Animals ; Cell Line, Tumor ; Chromatography, High Pressure Liquid ; Humans ; Lignans ; analysis ; chemistry ; isolation & purification ; Mice ; Plant Roots ; chemistry ; Rubiaceae ; chemistry ; Sitosterols ; chemistry ; isolation & purification ; pharmacology ; Triterpenes ; chemistry ; isolation & purification ; pharmacology

OBJECTIVETo investigate the chemical constituents of the roots of Knoxia valerianoides and their biological activities.

METHODThe anthraquinones were isolated by using a combination of various chromatographic techniques including column chromatography over silica gel, Sephadex LH-20, and reversed-phase HPLC. Structures of the isolates were identified by their physical-chemical properties and spectroscopic analysis including 2D NMR and MS. Antioxidant, anti-HIV, neuroprotective, and cytotoxic activities were screened by using cell-based models.

RESULTTwenty-two constituents were isolated from an ethanolic extract of the roots of K. valerianoides. Their structures were identified as nordamnacanthal (1), ibericin (2), rubiadin (3), damnacanthol (4), 2-ethoxymethylknoxiavaledin (5), 3-hydroxymorindone (6), knoxiadin (7), 2-formyl knoxiavaledin (8), lucidin (9), xanthopurpurin (10), 1, 3-dihydroxy-2-methoxy-9, 10- anthraquinone (11), lucidin(-methyl ether (12), digiferruginol (13), 3-hydroxy-2-methyl-9,10-anthraquinone (14), rubiadin-1-methyl ether (15), 6-methoxylucidin (-ethyl ether (16), 1,3,6-trihydroxy-2-methyl-9,10-anthraquinone (17), 1,3-dihydroxy-2-hydroxy methyl-6-methoxy-9,10-anthraquinone (18), 1,3,6-trihydroxy-2-methoxymethyl-9,10- anthraquinone (19), 3,6-dihydroxy-2- hydroxymethyl-9,10-anthraquinone (20), and 1,6-dihydroxy-2-methyl-9,10-anthra quinone (21). In the in vitro assays, at a concentration of 1 x 10(-5) mol x L(-1), no compounds were active against human cancer cell lines (HCT-8, Bel7402, BGC-823, A549, and A2780), deserum and glutamate induced PC12-syn cell damage, LPS induced NO production in macrophage, Fe2+-cystine induced rat liver microsomal lipid peroxidation, HIV-1 replication, and protein tyrosine phosphatase 1B (PTP1B).

CONCLUSIONCompounds 9-21 were obtained from the roots of K. valerianoides for the first time.

Animals ; Anthraquinones ; chemistry ; isolation & purification ; pharmacology ; Cell Line ; Drugs, Chinese Herbal ; chemistry ; isolation & purification ; pharmacology ; Humans ; Molecular Structure ; Plant Roots ; chemistry ; Rats ; Rubiaceae ; chemistry