RESUMO
Two new limonoids, named xylomexicanins C and D, were isolated from a dichloromethane extract of the seeds of Xylocarpus granatum cultivated in Hainan, China, and their structures were elucidated on the basis of one- and two-dimensional NMR (including 1H, 13C-NMR, DEPT, 1H-1H COSY, HSQC, HMBC, and NOESY) and confirmed by high-resolution mass spectrometry. Xylomexicanin C exhibited antiproliferative activity against human breast carcinoma cells (KT).
Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Limoninas/química , Limoninas/farmacologia , Meliaceae/química , Antineoplásicos/isolamento & purificação , Linhagem Celular Tumoral , Humanos , Limoninas/isolamento & purificaçãoRESUMO
OBJECTIVE: To study the chemical constituents in the needles of Taxus cuspidata collected from Japan. METHODS: Chemical constituents were isolated by column chromatography, TLC and preparative HPLC. The structures were identified on the basis of NMR spectral analysis. RESULTS: Six non-taxoids were isolated and identified as: 4-[(1E)-3-hydroxy-1-buten-1-yl]-3,5,5-trimethyl-2-cyclohexen-1-one (1), megastigm-5-ene-3, 9-diol (2), 6alpha-epoxy-7-megastigmen-9-one (3), 4-(4-hydroxyphenyl)-2-butanone (4), 12-hydroxy-alpha-cyperone (5), scutellarein-7-O-alpha-L-rhamnoside (6). CONCLUSION: Compounds 2 - 6 are isolated from Taxus genus for the first time. Compound 1 is obtained from Taxus cuspidata for the first time.
Assuntos
Taxus/química , Cromatografia Líquida de Alta Pressão , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , TaxoidesRESUMO
A phytochemical investigation of Chromolaena odorata resulted in the isolation of five new compounds, 5aα,6,9,9aß,10-pentahydro-10ß-hydroxy-7-methylanthra[1,2-d][1,3]dioxol-5-one (1), 1,2-methylenedioxy-6-methylanthraquinone (2), 3-hydroxy-1,2,4-trimethoxy-6-methylanthraquinone (3), 3-hydroxy-1,2-dimethoxy-6-methylanthraquinone (4), and 7-methoxy-7-epi-medioresinol (5), together with 12 known compounds, odoratin (6), 3ß-acetyloleanolic acid (7), ursolic acid (8), ombuin (9), 4,2'-dihydroxy-4',5',6'-trimethoxychalcone (10), (-)-pinoresinol (11), austrocortinin (12), tianshic acid (13), cleomiscosin D (14), (-)-medioresinol (15), (-)-syringaresinol (16), and cleomiscosin A (17). All the compounds were evaluated for their PPARγ transactivation activity, and compound 6 showed moderate activity with an EC(50) value of 3.10 µM.
Assuntos
Antraquinonas/isolamento & purificação , Chromolaena/química , Dioxóis/isolamento & purificação , Dioxóis/farmacologia , Medicamentos de Ervas Chinesas/isolamento & purificação , Medicamentos de Ervas Chinesas/farmacologia , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Lignanas/isolamento & purificação , Lignanas/farmacologia , PPAR gama/agonistas , Antraquinonas/química , Antraquinonas/farmacologia , Dioxóis/química , Medicamentos de Ervas Chinesas/química , Flavonoides/química , Furanos/química , Furanos/isolamento & purificação , Hepatócitos/efeitos dos fármacos , Humanos , Lignanas/química , Luciferases/metabolismo , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , EstereoisomerismoRESUMO
Eight sesquiterpene lactones were isolated from the roots of Inula helenium and flowers of I. japonica. Among them, isoalantolactone (3) and santamarine (6) exhibited significant growth inhibitory activities against gynecologic cancer cell lines, while others weakly inhibited the growth of the cell lines (IC50 < or = 100 microM). In addition, 3 significantly inhibited the tumour growth of S180 tumour-bearing mice. Compounds 3 and 6 were not toxic to human embryonic lung fibroblast cells in vitro. These results demonstrated that the antitumour activities are closely related to the structures of the compounds, that is, an alpha-exomethylene-gamma-lactone ring is necessary for these activities.
Assuntos
Antineoplásicos Fitogênicos/farmacologia , Inula/química , Lactonas/farmacologia , Sesquiterpenos/química , Linhagem Celular Tumoral , HumanosRESUMO
Seven undescribed sesquiterpene lactone dimers (SLDs) (carpeabrodilactones A-G), one known SLD, and six known sesquiterpenes were isolated from the fruit of Carpesium abrotanoides L. Carpeabrodilactone A was a dimeric carabrane featuring a rare C-13-C-13' linkage. Carpeabrodilactones B and C are the first two SLDs to be described possessing a carabranolide unit and a guaianolide unit connected by an O-ether linkage. The structures of the SLDs were assigned based on HRESIMS, NMR analysis, 13C NMR calculation, ECD calculation, and modified Mosher's method. Four SLDs showed potent cytotoxicity against K562 and/or A549 cells, with IC50 values below 10 µM, but none inhibited protein tyrosine phosphatases at 40 µM, including PTP1B, SHP1, CD45, and TCPTP.
Assuntos
Asteraceae , Sesquiterpenos , Asteraceae/química , Éteres , Frutas , Lactonas/química , Lactonas/farmacologia , Estrutura Molecular , Compostos Fitoquímicos , Sesquiterpenos/química , Sesquiterpenos/farmacologiaRESUMO
A novel 6/8/6-membered taxane with a rare C-12(13)-double bond and rare 2(3â20)abeotaxane were isolated from the needles of Taxus canadensis. Their structures were characterized as 7ß,9α,10ß-triacetoxytaxa-4(20),12-diene-2α,5α,11ß-triol (1) and 2α,7ß,10ß-triacetoxy-5α-hydroxy-2(3â20)abeotaxa-4(20),11-diene-9,13-dione (2) on the basis of 1D and 2D spectroscopic data. 1 is the first example of a natural taxane without substitution at both C-13 and C-14.
Assuntos
Antineoplásicos/análise , Extratos Vegetais/análise , Taxoides/análise , Taxus/química , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Neoplasias da Mama/patologia , Linhagem Celular Tumoral , Feminino , Humanos , Espectroscopia de Ressonância Magnética , Masculino , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Folhas de Planta/química , Neoplasias da Próstata/tratamento farmacológico , Neoplasias da Próstata/patologia , Taxoides/química , Taxoides/isolamento & purificação , Taxoides/farmacologia , Falha de Tratamento , Neoplasias do Colo do Útero/tratamento farmacológico , Neoplasias do Colo do Útero/patologiaRESUMO
Achillinin A (2ß,3ß-epoxy-1α,4ß,10α-trihydroxyguai-11(13)-en-12,6α-olide, 1), a new guaianolide isolated from the flower of Achillea millefolium, exhibited potential antiproliferative activity to A549, RERF-LC-kj and QG-90 cells with 50% inhibitory concentration (IC(50)) values of 5.8, 10 and 0.31 µM, respectively.
Assuntos
Achillea/química , Adenocarcinoma/tratamento farmacológico , Antineoplásicos Fitogênicos/farmacologia , Carcinoma Pulmonar de Células não Pequenas/tratamento farmacológico , Neoplasias Pulmonares/tratamento farmacológico , Fitoterapia , Extratos Vegetais/farmacologia , Sesquiterpenos/farmacologia , Carcinoma de Pequenas Células do Pulmão/tratamento farmacológico , Adenocarcinoma/patologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/uso terapêutico , Carcinoma Pulmonar de Células não Pequenas/patologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Flores/química , Humanos , Concentração Inibidora 50 , Neoplasias Pulmonares/patologia , Espectroscopia de Ressonância Magnética , Extratos Vegetais/química , Extratos Vegetais/uso terapêutico , Sesquiterpenos/química , Sesquiterpenos/uso terapêutico , Carcinoma de Pequenas Células do Pulmão/patologiaRESUMO
Three new taxanes, 2 α,9 α,10 ß-triacetoxy-13 α-( ß-D-glucopyranosyloxy)taxa-4(20),11-dien-5 α-ol, 5 α,10 ß,13 α-triacetoxytax-11-ene-2 α,7 ß,9 α,20-tetraol, and 5 α,10 ß,13 ß-triacetoxy-2 α,7 ß-dihydroxy-2(3â20) abeotaxa-4(20),11-dien-9-one, were isolated from the leaves of the Japanese yew, Taxus cuspidata. Compound 1 is the first example of a taxane with 13-glycosidic linkage.
Assuntos
Glucosídeos/isolamento & purificação , Extratos Vegetais , Taxoides/isolamento & purificação , Taxus/química , Glucosídeos/química , Estrutura Molecular , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Folhas de Planta , Taxoides/químicaRESUMO
Ocean is a unique and excellent resource that provides a diverse array of intriguing natural products. Marine natural products have demonstrated significant and extremely potent biological activities and have captured the attention of natural products chemists in the past few decades. It is increasingly recognized that a wealth of fascinating natural products and novel chemical entities will play a dominant role in the discovery of useful leads for the development of pharmaceutical agents and provide useful probes to lead to breakthroughs in a variety of life-science fields. This article focused on the research progress of chemistry of marine natural products in recent five years.
Assuntos
Organismos Aquáticos/química , Produtos Biológicos/isolamento & purificação , Biologia Marinha , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Animais , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antineoplásicos/farmacologia , Produtos Biológicos/química , Produtos Biológicos/farmacologia , Humanos , Macrolídeos/química , Macrolídeos/isolamento & purificação , Macrolídeos/farmacologia , Toxinas Marinhas/química , Toxinas Marinhas/isolamento & purificação , Toxinas Marinhas/farmacologia , Estrutura Molecular , Peptídeos/química , Peptídeos/isolamento & purificação , Peptídeos/farmacologia , Esteroides/química , Esteroides/isolamento & purificação , Esteroides/farmacologia , Terpenos/química , Terpenos/isolamento & purificação , Terpenos/farmacologiaRESUMO
Taxusecone, 2alpha,7beta,9alpha,10beta-tetraacetoxy-5alpha,12-dihydroxy-11,12-secotax-4(20)-ene-11,13-dione (1), a novel taxane with an unprecedented skeleton, was isolated from the needles of Taxus cuspidata.
Assuntos
Taxoides/química , Taxoides/isolamento & purificação , Taxus/química , Taxus/anatomia & histologia , Taxus/metabolismoRESUMO
The plants of genus Celastrus, distributed in Asia, have been used as natural insecticides and folk medicines to treat fever, chill, joint pain, edema, rheumatoid arthritis, and bacterial infection in China for a long time. This contribution reviews the chemical constituents, isolated from the plants in genus Celastrus in the past few decades, and their biological activities. The compounds listed are sesquiterpenes (beta-agarofurans), diterpenes, triterpenes, alkaloids, and flavonoids.
Assuntos
Celastrus/química , Alcaloides/química , Alcaloides/isolamento & purificação , Alcaloides/farmacologia , Diterpenos/química , Diterpenos/isolamento & purificação , Diterpenos/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Medicina Tradicional Chinesa , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Triterpenos/química , Triterpenos/isolamento & purificação , Triterpenos/farmacologiaRESUMO
Two new mexicanolide-type limonoids, named xylomexicanin A (1) and xylomexicanin B (2), were isolated from seeds of the Chinese mangrove Xylocarpus granatum. Their structures were elucidated on the basis of spectroscopic methods. Compound 1 exhibited antiproliferative activity against human breast carcinoma cells (KT), while 2 did not show inhibitory effects on eleven human tumour cell lines tested.
Assuntos
Antineoplásicos/química , Antineoplásicos/farmacologia , Neoplasias da Mama/tratamento farmacológico , Limoninas/química , Limoninas/farmacologia , Meliaceae/química , Neoplasias/tratamento farmacológico , Sementes/química , Antineoplásicos/isolamento & purificação , Sudeste Asiático , Linhagem Celular Tumoral/efeitos dos fármacos , Feminino , Humanos , Limoninas/isolamento & purificação , Espectroscopia de Ressonância Magnética , Medicina TradicionalRESUMO
Two 11(15-->1)abeotaxanes having a tetrahydrofuran ring along the carbon atoms C-2, C-3, C-4, C-20 were identified for the first time from the needles of the Canadian yew, Taxus canadensis. The compounds could be identified as 4alpha,10beta,13alpha-triacetoxy-15-benzoyloxy-2alpha,20beta-epoxy-11(15-->1)abeotax-11-ene-5alpha,7beta,9alpha-triol (1) and 4alpha,7beta,9alpha,10beta,15-pentaacetoxy-2alpha,20beta-epoxy-11(15-->1)abeotax-11-ene-5alpha,13alpha-diol (2) on the basis of 1D-, 2D-NMR evidence and high-resolution FABMS analysis. Compound 1 showed weak growth inhibitory activities against T-98 and MM1-CB cells in vitro.
Assuntos
Linhagem Celular Tumoral/efeitos dos fármacos , Compostos de Epóxi/química , Células HeLa/efeitos dos fármacos , Taxoides/química , Taxus/química , Sobrevivência Celular/efeitos dos fármacos , Compostos de Epóxi/isolamento & purificação , Compostos de Epóxi/farmacologia , Humanos , Espectroscopia de Ressonância Magnética , Modelos Moleculares , Folhas de Planta/química , Taxoides/isolamento & purificação , Taxoides/farmacologiaRESUMO
Echinopines A (1) and B (2), novel sesquiterpenoids with an unprecedented rearranged skeleton named echinopane, were isolated from the roots of Echinops spinosus. The structures were elucidated by extensive spectroscopic analysis. The relative configuration of 1 was assigned by a combination of NOESY correlations and a simulation analysis. A plausible biosynthetic pathway for echinopane was discussed.
Assuntos
Echinops (Planta)/química , Plantas Medicinais/química , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Estrutura Molecular , Sesquiterpenos/farmacologiaRESUMO
The chemical constituents of Symplocos genus were reviewed with 90 structures and 28 references cited. These constituents include triterpenoids, flavonoids, lignans, phenols, steroids, alkaloids, and iridoids. Triterpenoids are the dominant constituents within the genus Symplocos, some of them exhibited antiproliferative effects. Some phenolic glycoside derivatives showed inhibitory activity against snake-venom phosphodiesterase I and human nucleotide pyrophosphatase phosphodiesterase.
Assuntos
Magnoliopsida/química , Estrutura MolecularRESUMO
A new taxoid metabolite with a new substitution pattern was isolated from the methanol extract of the seeds of Taxus mairei, and its structure was established as 5alpha,15-dihydroxy-7beta,9alpha-diacetoxy-11(15-->1)abeo-taxa-4(20),11-dien-13-one (1) on the basis of spectral analysis including (1)H- and (13)C-NMR, HMQC, HMBC, NOESY, and confirmed by HR-FAB mass spectrometry.
Assuntos
Extratos Vegetais/química , Sementes/química , Taxus/química , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Espectrometria de Massas de Bombardeamento Rápido de ÁtomosRESUMO
OBJECTIVE: To study the non-taxoids in the leaves of Taxus mairei. METHOD: The chemical constituents were isolated by chromatography and identified by spectral data. RESULT: Five compounds, taxamairin A (1), taxamairin B (2), sciadopitysin (3), ( - ) matairesinol (4), ponasterone A (5) were isolated and identified. CONCLUSION: Compounds 3-5 were isolated from this plant for the first time, compounds 1 and 2 were isolated from the leaves of T. mairei for the first time.
Assuntos
Biflavonoides/isolamento & purificação , Ecdisterona/análogos & derivados , Furanos/isolamento & purificação , Lignanas/isolamento & purificação , Plantas Medicinais/química , Taxus/química , Biflavonoides/química , Diterpenos/química , Diterpenos/isolamento & purificação , Ecdisterona/química , Ecdisterona/isolamento & purificação , Furanos/química , Lignanas/química , Folhas de Planta/químicaAssuntos
Senécio/química , Alcaloides/química , Alcaloides/farmacologia , Alcanos/química , Alcanos/farmacologia , Cumarínicos/química , Cumarínicos/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Flavonoides/química , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Monoterpenos/química , Monoterpenos/farmacologia , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Esteroides/química , Esteroides/farmacologia , Triterpenos/química , Triterpenos/farmacologiaRESUMO
OBJECTIVE: To study the chemical constituents of Acanthus ilicifolius. METHOD: Chromatographic methods were used to isolate compounds from A. ilicifolius, and chemical and spectroscopic methods were used to elucidate the structures of the isolated compounds. RESULT: Seven compounds, betaine (1), phenylethyl-O-beta-D-glucopyranosyl- (1-->2) -beta-D-glucopyranoside (2), phenylethyl-O-beta-D-glucopyranoside (3), acteoside (4), isoacteoside (5), benzyl-O-beta-D-glucopyranoside (6) and vanillic acid (7) were obtained. CONCLUSION: 1, 3, 6 and 7 were obtained from the genus for the first time.
Assuntos
Acanthaceae/química , Betaína/isolamento & purificação , Glucosídeos/isolamento & purificação , Plantas Medicinais/química , Ácido Vanílico/isolamento & purificação , Betaína/química , Glucosídeos/química , Ácido Vanílico/químicaRESUMO
OBJECTIVE: To study the chemical constituents in the heartwood of Taxus cuspidata. METHOD: Silica gel column chromatography, preparative HPLC and preparative TLC were used to isolate and purify the chemical constituents; 1H- and 13C-NMR spectroscopic methods were used for structural identification. RESULT: Ten compounds, taxinine (1), taxusin (2), beta-sitosterol (3), 1 beta-hydroxybaccatin I (4), 2alpha, 5alpha, 10beta-triacetoxy-14beta-(2'-methyl) butanoyloxy-4 (20), 11-taxadiene (5), 2alpha, 5alpha, 10beta-triacetoxy-14beta-(2'-methyl-3'-hydroxy-butanoyloxyl-4 (20), 11-taxadiene (yunnanxane) (6), 9alpha, 10beta, 13alpha-triacetoxy-5alpha-cinnamoyltaxa-4 (20), 11-diene (7), 2-deacetoxytaxinine J (8), taxezopidine G (9), 2alpha, 7beta, 9alpha, 10beta, 13alpha-pentaacetoxyl-taxa-4 (20), 11-dien-5-ol (5-decinnamoyltaxinine J) (10), were isolated and identified from the heartwood of T. cuspidata. CONCLUSION: Three taxanes, 1 beta-hydroxybaccatin I (4), 2alpha, 5alpha, 10beta-triacetoxy-14beta-(2'-methyl-3'-hydroxy-butanoyloxy)-4 (20), 11-taxadiene (yunnanxane) (6), and 2alpha, 7beta, 9alpha, 10beta, 13alpha-pentaacetoxyltaxa-4 (20) , 11-dien-5-ol (10), were obtained from this plant for the first time.