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1.
Fitoterapia ; 139: 104418, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31704262

RESUMO

A new isoiphionane sesquiterpene, named (3S, 5S, 7S, 10R)-3, 11-dihydroxyisoiphion-4-one (1), two new phloroglucinol glycosides, named eucalglobuside A (2) and eucalglobuside B (3), along with 15 known compounds were isolated from the leaves of Eucalyptus globulus. Their structures were elucidated based on extensive spectroscopic analysis and in comparison with literature data. The absolute configuration of compound 1 was determined by ECD calculation. All isolates were evaluated their inhibitory activities against the mushroom tyrosinase. As a result, three sesquiterpenoids, 1, 5ß, 11-dihydroxy-iphionan-4-one (5), and (-)-globulol (8), exhibited the most potent activities with IC50 values of 14.17 µM, 10.08 µM and 9.79 µM, respectively.


Assuntos
Inibidores Enzimáticos/farmacologia , Eucalyptus/química , Glicosídeos/farmacologia , Monofenol Mono-Oxigenase/antagonistas & inibidores , Floroglucinol/farmacologia , Sesquiterpenos/farmacologia , China , Inibidores Enzimáticos/isolamento & purificação , Glicosídeos/isolamento & purificação , Estrutura Molecular , Floroglucinol/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Compostos Fitoquímicos/farmacologia , Folhas de Planta/química , Sesquiterpenos/isolamento & purificação
2.
Chem Pharm Bull (Tokyo) ; 66(12): 1199-1202, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-30504634

RESUMO

Four new prenylated 2-arylbenzofurans, namely artopithecins A-D (1-4), together with five known compounds (5-9) were isolated from the twigs of Artocarpus pithecogallus for the first time. Their structures were elucidated based on extensive spectroscopic analysis and in comparison with literature data. All isolates were evaluated for their inhibitory activities against mushroom tyrosinase. Compounds 3 and 4 displayed significant tyrosinase inhibitory activities with IC50 values of 37.09±0.33 and 38.14±0.21 µM, respectively.


Assuntos
Artocarpus/química , Benzofuranos/farmacologia , Inibidores Enzimáticos/farmacologia , Monofenol Mono-Oxigenase/antagonistas & inibidores , Caules de Planta/química , Agaricales/enzimologia , Benzofuranos/química , Benzofuranos/isolamento & purificação , Relação Dose-Resposta a Droga , Inibidores Enzimáticos/química , Inibidores Enzimáticos/isolamento & purificação , Estrutura Molecular , Monofenol Mono-Oxigenase/metabolismo , Prenilação , Relação Estrutura-Atividade
3.
Chem Pharm Bull (Tokyo) ; 66(4): 434-438, 2018.
Artigo em Inglês | MEDLINE | ID: mdl-29607909

RESUMO

Two new prenylated flavones, artocarnin A (2) and carpachromenol (12), together with 13 known prenylflavonoids (1, 3-11, 13-15) were isolated from the twigs of Artocarpus nigrifolius for the first time. Their structures were elucidated by high resolution-electrospray ionization (HR-ESI)-MS, NMR spectroscopic analysis, and in comparison with the reported data. Compounds 1-15 were evaluated for their antiproliferative effects against SiHa and SGC-7901 human cancer cell lines in vitro. The most active compound, eleocharin A (10), showed significant cytotoxicity on SiHa cells (IC50=0.7±0.1 µM) and inhibitory activity against SGC-7901 cells (IC50=8.3±0.2 µM) and could be considered as potential lead compound for further development of novel anti-tumor agents.


Assuntos
Antineoplásicos Fitogênicos/farmacologia , Artocarpus/química , Flavonoides/farmacologia , Casca de Planta/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/isolamento & purificação , Proliferação de Células/efeitos dos fármacos , Relação Dose-Resposta a Droga , Ensaios de Seleção de Medicamentos Antitumorais , Flavonoides/química , Flavonoides/isolamento & purificação , Humanos , Estrutura Molecular , Relação Estrutura-Atividade , Células Tumorais Cultivadas
4.
J Nat Prod ; 71(8): 1414-7, 2008 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-18611050

RESUMO

Five new diterpenes, trigonochinenes A-E (1-5), and two known ones, 3,4- seco-sonderianol (6) and 3,4- seco-sonderianic acid (7), were isolated from the aerial part of Trigonostemon chinensis. Compounds 1-4 possess a rare 3,4-seco-cleistanthanic skeleton, and compound 5 is a highly aromatized tetranorditerpene. Structures of these compounds were elucidated by spectroscopic analysis. The antimicrobial activities of compounds 1-7 were evaluated against a panel of bacteria and fungi.


Assuntos
Anti-Infecciosos/isolamento & purificação , Diterpenos/isolamento & purificação , Euphorbiaceae/química , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Bactérias/efeitos dos fármacos , Dicroísmo Circular , Diterpenos/química , Diterpenos/farmacologia , Fungos/efeitos dos fármacos , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Estrutura Molecular , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Infravermelho
5.
J Nat Prod ; 71(8): 1410-3, 2008 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-18651771

RESUMO

Five new guaiane-type sesquiterpenoids, hedyosumins A-E (1-5), together with five known ones (6-10), were isolated from the aerial parts of Hedyosmum orientale. Two known sesquiterpenoids, 10alpha-hydroxy-1,5alpha H-guaia-3,7(11)-dien-8alpha,12-olide and 9alpha-hydroxyasterolide, were obtained as natural products for the first time. Their structures were elucidated on the basis of spectroscopic methods. 9alpha-Hydroxyasterolide (7) showed moderate activities against A-549 and HL-60 tumor cell lines with the IC 50 values of 3.1 and 8.8 microM, respectively.


Assuntos
Magnoliopsida/química , Sesquiterpenos/isolamento & purificação , Linhagem Celular Tumoral , Cromatografia Líquida de Alta Pressão , Humanos , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Sesquiterpenos/química , Espectrometria de Massas por Ionização por Electrospray , Espectrofotometria Ultravioleta
6.
Org Lett ; 10(3): 465-8, 2008 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-18163640

RESUMO

Walsucochins A (1) and B (2) with an unprecedented skeleton were isolated from Walsura cochinchinensis. Their structures including absolute configuration were elucidated by spectral methods. A biosynthetic pathway of 1 and 2 was postulated. Both 1 and 2 exhibited significant cell protecting activities against H2O2-induced PC12 cell damage.


Assuntos
Meliaceae/química , Plantas Medicinais/química , Triterpenos/química , Triterpenos/isolamento & purificação , Animais , Sobrevivência Celular/efeitos dos fármacos , Relação Dose-Resposta a Droga , Peróxido de Hidrogênio/farmacologia , Estrutura Molecular , Células PC12 , Folhas de Planta/química , Caules de Planta/química , Ratos , Triterpenos/farmacologia
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