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1.
Chem Biodivers ; 2020 Mar 16.
Artigo em Inglês | MEDLINE | ID: mdl-32180346

RESUMO

Three dimeric cassane diterpenoids, caesalpanins A-C ( 1-3 ), were isolated from the seeds of Caesalpinia sappan L.. Their structures were determined via analysis of 1D-, 2D-NMR, and HR-ESI-MS data. Compounds 1 and 2 were the second examples of nitrogen containing cassane diterpenoid dimer linked through one ether bond between C-19 and C-20'. Compound 2 exhibited moderate cytotoxic activity against MCF-7 cell line with IC 50 value of 29.98 µ M. Compounds 1 and 2 had weak inhibitory effects against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages at 50 µ M with inhibitory rate of 36.01% and 32.93%, respectively.Three dimeric cassane diterpenoids, caesalpanins A-C ( 1-3 ), were isolated from the seeds of Caesalpinia sappan L., as well as three known compounds ( 4-6 ). Their structures were determined via analysis of 1D-, 2D-NMR, and HR-ESI-MS data. Compounds 1 and 2 were the second and third compounds that presented a nitrogen containing cassane diterpenoid dimer linked through one ether bond between C-19 and C-20'. Compound 2 exhibited moderate cytotoxic activity against MCF-7 cell line with IC 50 value of 29.98 µ M. Compounds 1 and 2 had weak inhibitory effects against LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages at 50 µ M with inhibitory rate of 36.01% and 32.93%, respectively.

2.
Phytochemistry ; 161: 86-96, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30822624

RESUMO

A phytochemical study on the stem bark of Metasequoia glyptostroboides led to the isolation of sixty-one diterpenoids and sesquiterpenoids, including seventeen previously undescribed compounds, metaglyptins A-Q. Their structures were elucidated by extensive analysis of spectroscopic data (IR, UV, HRESIMS, and 1H, 13C and 2D NMR). The absolute configurations of metaglyptins I, J, and O were determined by the ECD data and single-crystal X-ray diffraction analysis. The undescribed compounds were evaluated for their cytotoxicity against HeLa, AGS, and MDA-MB-231 cancer cell lines. The results revealed that metaglyptin A exhibited moderate cytotoxicity against MDA-MB-231 cell line with IC50 value of 20.02 µM.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Cupressaceae/química , Diterpenos/farmacologia , Casca de Planta/química , Caules de Planta/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Células HeLa , Humanos , Modelos Moleculares , Conformação Molecular , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
3.
Chem Biodivers ; 16(5): e1900013, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30811806

RESUMO

Thirteen sesquiterpenes including eight new ones, magnodelavins A-H (1-8), were obtained from the 95 % ethanolic extract of the leaves of Magnolia delavayi Franch. The structures of the new compounds were determined by exhaustive 1 H-, 13 C-, 2D-NMR, UV, IR, and HR-ESI-MS data, as well as X-ray crystallographic analysis. Compounds 9 and 10 showed potent cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, and SW480 human cancer cell lines in vitro using MTS assay.


Assuntos
Antineoplásicos Fitogênicos/química , Magnolia/química , Sesquiterpenos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Antineoplásicos Fitogênicos/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Ensaios de Seleção de Medicamentos Antitumorais , Células HL-60 , Humanos , Espectroscopia de Ressonância Magnética , Magnolia/metabolismo , Conformação Molecular , Folhas de Planta/química , Folhas de Planta/metabolismo , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Espectrometria de Massas por Ionização por Electrospray
4.
Phytochemistry ; 155: 182-190, 2018 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-30145456

RESUMO

Nine previously undescribed sesquiterpenoids, named magnograndins A-I, as well as fourteen known ones, were obtained from the 70% acetone extract of the leaves of Magnolia grandiflora. Their structures were ascertained based on the spectroscopic evidences. The assignment of the relative configuration of magnograndin A was further confirmed by single-crystal X-ray diffraction analysis. 1ß,10α-Epoxyparthenolide, parthenolide, and micheliolide exhibited potent cytotoxic activity against MDA-MB-468, AGS, HCT116, Hela, and MDA-MB-231 human cancer cell lines with IC50 values ranging from 1.76 to 16.11 µM. 1ß,10α-Epoxyparthenolide and micheliolide potently inhibited NF-κB transcriptional activity with IC50 of 13.92 and 8.95 µM, respectively. The expression levels of NF-κB downstream protein p65 and XIAP were clearly down-regulated in 1ß,10α-epoxyparthenolide and micheliolide treated cells, which demonstrated the inhibition of NF-κB signaling pathway.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Inibidores Enzimáticos/farmacologia , Magnolia/química , Folhas de Planta/química , Sesquiterpenos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Humanos , Luciferases/antagonistas & inibidores , Luciferases/genética , Luciferases/metabolismo , Estrutura Molecular , NF-kappa B/antagonistas & inibidores , NF-kappa B/metabolismo , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Relação Estrutura-Atividade
5.
Chem Biodivers ; 15(6): e1800124, 2018 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29667782

RESUMO

Twelve new ent-labdane diterpenoids, hypofolins A - F (1 - 6) and hypofolins G - L (7a/7b, 8a/8b, and 9a/9b), were isolated from the roots of Hypoestes phyllostachya 'Pink Splash'. Their structures were elucidated by extensive 1D- and 2D-NMR spectroscopic and HR-MS data. The absolute configurations of 1, 2, 5, and 7a/7b were determined by single crystal X-ray diffraction and ECD analysis, as well as chemical transformations. Compounds 7a/7b, 8a/8b, and 9a/9b were isolated as three pairs of interconverting mixture of two isomers between ketone and hemiketal types. Compound 1 showed weak cytotoxicity against SMMC-7721 cell line with IC50 value of 31.40 µm.


Assuntos
Acanthaceae/química , Antineoplásicos Fitogênicos/farmacologia , Diterpenos/farmacologia , Raízes de Plantas/química , Animais , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Diterpenos/química , Diterpenos/isolamento & purificação , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Lipopolissacarídeos/antagonistas & inibidores , Lipopolissacarídeos/farmacologia , Camundongos , Estrutura Molecular , Óxido Nítrico/antagonistas & inibidores , Óxido Nítrico/biossíntese , Células RAW 264.7 , Relação Estrutura-Atividade
6.
J Asian Nat Prod Res ; 19(7): 666-672, 2017 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-27989219

RESUMO

A rare carotane-type sesquiterpenoid, forkienin A (1), a new eudesmane-type sesquiterpenoid, forkienin B (2), and a new natural eudesmane-type sesquiterpenoid, forkienin C (3), were isolated from the twigs and leaves of Fokienia hodginsii, along with eight known sesquiterpenoids. The structures of the new compounds were elucidated on the basis of their spectroscopic analysis, including 1D and 2D NMR methods. All compounds were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Folhas de Planta/química , Caules de Planta/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Sesquiterpenos/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Células HL-60 , Humanos , Estrutura Molecular , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia
7.
Yao Xue Xue Bao ; 52(2): 279-82, 2017 Feb.
Artigo em Chinês | MEDLINE | ID: mdl-29979518

RESUMO

Five cassane diterpenes were isolated from the 95% ethanol extract of the seeds of Caesalpinia bonduc (Leguminosea) by a combination of various chromatographic methods, including silica gel, Sephadex LH-20, and semi-preparative HPLC. On the basis of spectroscopic techniques, their structures were identified as 3ß-acetoxy-cassa-12,14(17),15-trien-7ß-ol (1), caesalmin C (2), caesall E (3), caesalpinin MJ (4), and 1-deacetylcaesalmin C (5). Among them, compound 1 is a new compound and 2, 4, 5 were isolated from the plant for the first time.


Assuntos
Caesalpinia/química , Diterpenos/química , Sementes/química , Diterpenos/isolamento & purificação , Estrutura Molecular , Extratos Vegetais/química
8.
Phytochemistry ; 129: 68-76, 2016 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-27452450

RESUMO

Phytochemical investigation of the flowers of Inula japonica led to isolation of nine sesquiterpenoids, inujaponins A-I, as well as eighteen known ones. These sesquiterpenoids belong to six skeletal-types, including eudesmane, 1,10-seco-eudesmane, germacrane, guaiane, 4,5-seco-guaiane, and pseudoguaiane sesquiterpenoids. Their structures were established by extensive spectroscopic analysis. The absolute configurations of inujaponin A, eupatolide, and deacetylovatifolin were determined by Cu-Kα X-ray crystallographic analysis. Most of the isolated compounds exhibited potent cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW-480 cancer cell lines, with IC50 values ranging from 1.57 to 22.58 µM. Some selected compounds also possessed significant inhibitory activity against LPS-induced NO production in RAW264.7 macrophages with IC50 values ranging from 1.42 to 8.99 µM.


Assuntos
Flores/química , Inula/química , Sesquiterpenos de Eudesmano/isolamento & purificação , Animais , Cristalografia por Raios X , Células HL-60 , Humanos , Concentração Inibidora 50 , Lipopolissacarídeos/farmacologia , Macrófagos/efeitos dos fármacos , Camundongos , Conformação Molecular , Estrutura Molecular , Óxido Nítrico/biossíntese , Sesquiterpenos/química , Sesquiterpenos/isolamento & purificação , Sesquiterpenos/farmacologia , Sesquiterpenos de Eudesmano/química , Sesquiterpenos de Eudesmano/farmacologia , Sesquiterpenos de Guaiano/química , Sesquiterpenos de Guaiano/isolamento & purificação , Sesquiterpenos de Guaiano/farmacologia
9.
Zhong Yao Cai ; 39(6): 1296-9, 2016 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-30156801

RESUMO

Objective: To study the chemical constituents of Inula japonica. Methods: Silica gel, Sephadex LH-20,MCI and semipreparative HPLC were used to isolate and purify the constituents of Inula japonica,and the chemical structures were elucidated by chemical properties, MS and NMR analysis. Results: 14 compounds were isolated and their structures were identified as ivangustin( 1),1-acetoxy-6α-hydroxyeriolanolide( 2), 1ß-hydroxyalantolactone( 3),tomentosin( 4),11,13-dihydroinuchinenolide B( 5), britanlin A( 6),vomifoliol( 7), 17-hydroxy-16α-ent-kauran-19-oic acid( 8), 12-hydroxygeranylgeraniol ( 9), dihydroquercetin( 10), kaempferol( 11), quercetin( 12), dihydroconiferyl alcohol( 13) and fareanol( 14). Conclusion: Compounds 5,6,9,13 and 14 are isolated from this plant for the first time.


Assuntos
Inula , Diterpenos de Caurano , Medicamentos de Ervas Chinesas , Quempferóis , Lactonas , Espectroscopia de Ressonância Magnética , Sesquiterpenos
10.
Zhong Yao Cai ; 37(5): 807-11, 2014 May.
Artigo em Chinês | MEDLINE | ID: mdl-25335288

RESUMO

OBJECTIVE: To study the chemical compositions of Eucommia ulmoides. METHODS: The compounds were isolated and purified from Eucommia ulmoides by silica gel column chromatography, Sephadex LH-20, MPLC packed with MCI gel and semi-preparative HPLC. The structures of these compounds were established on the basis of spectral analyses (1H-NMR, 13C-NMR and MS). RESULTS: Thirteen compounds were obtained,and their structures were identified as betulin (1), syringin (2), pervoside A (3), glucosyringic acid (4), vanillic acid-beta-glucoside (5), geniposide acid (6), aucubin (7), geniposide (8), pinoresinol-4,4'-di-O-beta-D-glucopyranoside (9), syringaresinol di-O-beta-D-glucopyranoside (10), medioresinol di-O-beta-D-glucopyranoside (11), sucrose (12), and ethyl beta-glucopyranoside (13) on the basis of physical characteristics and spectral data. CONCLUSION: Compounds 3 - 5, 12 and 13 are isolated from this plant for the first itme.


Assuntos
Medicamentos de Ervas Chinesas/química , Eucommiaceae/química , Plantas Medicinais/química , Benzoatos/química , Benzoatos/isolamento & purificação , Cromatografia Líquida de Alta Pressão/métodos , Ácidos Cumáricos/química , Ácidos Cumáricos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Glucosídeos/química , Glucosídeos/isolamento & purificação , Estrutura Molecular , Casca de Planta/química
11.
Planta Med ; 80(8-9): 703-9, 2014 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-24963619

RESUMO

Tussilagone (TSL) and its allied sesquiterpenoids were considered as the main active principles of the flower buds of Tussilago farfara, which has been widely used in China as an antitussive herbal medicine. Six new bisabolane-type sesquiterpenoids, tussfararins A-F (1-6), along with 12 known sesquiterpenoids, were isolated from the flower buds of T. farfara. Structures of the new compounds were elucidated by extensive spectroscopic analysis. The biological analysis showed that compounds 1, 3, 6, and 7 inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells with IC50 values of 13.6-24.4 µM.


Assuntos
Antitussígenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Lipopolissacarídeos/efeitos adversos , Óxido Nítrico/metabolismo , Sesquiterpenos/isolamento & purificação , Tussilago/química , Animais , Antitussígenos/química , Antitussígenos/farmacologia , Linhagem Celular Tumoral , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Flores/química , Concentração Inibidora 50 , Espectroscopia de Ressonância Magnética , Camundongos , Estrutura Molecular , Plantas Medicinais , Sesquiterpenos/química , Sesquiterpenos/farmacologia
12.
J Asian Nat Prod Res ; 15(2): 151-7, 2013.
Artigo em Inglês | MEDLINE | ID: mdl-23323987

RESUMO

A new tigliane diterpenoid, acerifolin A (1), and a new isopimarane diterpenoid, acerifolin B (2), together with two known compounds, were isolated from Excoecaria acerifolia. Their structures were elucidated on the basis of their spectroscopic methods, including 1D and 2D NMR techniques. All of the compounds were evaluated for cytotoxicity against five human cancer cell lines with cisplantin as a positive control.


Assuntos
Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Medicamentos de Ervas Chinesas/isolamento & purificação , Euphorbiaceae/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Cisplatino/farmacologia , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/farmacologia , Feminino , Células HL-60 , Humanos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular
13.
Fitoterapia ; 85: 154-60, 2013 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-23353657

RESUMO

Three new labdane diterpenoids, calomacrins A-C (1-3), and a new diaryl butyrolactone-type lignan, calomacrol A (8), as well as four known labdane diterpenoids and six known lignans, were isolated from the twigs and leaves of Calocedrus macrolepis. Structures of the new compounds were elucidated on the basis of their spectroscopic methods, including 1D and 2D NMR techniques. Compounds 3-14 were evaluated for cytotoxicity against HL-60, SMMC-7721, A-549, MCF-7, and SW480 cell lines.


Assuntos
4-Butirolactona/análogos & derivados , Antineoplásicos Fitogênicos/isolamento & purificação , Benzodioxóis/isolamento & purificação , Cupressaceae/química , Diterpenos/isolamento & purificação , 4-Butirolactona/química , 4-Butirolactona/isolamento & purificação , Antineoplásicos Fitogênicos/química , Benzodioxóis/química , Diterpenos/química , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Células MCF-7
14.
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