RESUMO
Bioactivity-guided fractionation of the stem bark of Mitrephora glabra yielded nine compounds, comprising three ent-kaurenoids (1-3), five polyacetylenic acids/esters (4-8), and one aporphine alkaloid, liriodenine (9). The structures of the six new compounds (1-3, 5, 7, and 8) were determined by spectroscopic data interpretation. All compounds were evaluated for their inhibitory activities against a panel of cancer cell lines and a battery of microorganisms.
Assuntos
Annonaceae/química , Anti-Infecciosos/isolamento & purificação , Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Plantas Medicinais/química , Poli-Inos/isolamento & purificação , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Aporfinas/isolamento & purificação , Aspergillus niger/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Feminino , Humanos , Indonésia , Testes de Sensibilidade Microbiana , Micrococcus luteus/efeitos dos fármacos , Estrutura Molecular , Mycobacterium/efeitos dos fármacos , Ressonância Magnética Nuclear Biomolecular , Casca de Planta/química , Poli-Inos/química , Poli-Inos/farmacologia , Saccharomyces cerevisiae/efeitos dos fármacosRESUMO
[chemical reaction: see text]. Three new ent-trachylobane diterpenoids (1-3) were isolated and structures elucidated from Mitrephora glabra Scheff. (Annonaceae). Mitrephorone A (1) possesses a hexacyclic ring system with adjacent ketone moieties and an oxetane ring, both of which are unprecedented among trachylobanes. All compounds were evaluated for cytotoxicity against a panel of cancer cells, where 1 displayed the most potent and broadest activity, and against a battery of antimicrobial assays, where all compounds were approximately equipotent.
Assuntos
Annonaceae/química , Antineoplásicos Fitogênicos/isolamento & purificação , Diterpenos/isolamento & purificação , Plantas Medicinais/química , Anfotericina B/farmacologia , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Bactérias/efeitos dos fármacos , Diterpenos/química , Diterpenos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Saccharomyces cerevisiae/efeitos dos fármacos , Células Tumorais CultivadasRESUMO
Activity-guided fractionation of a CHCl(3)-soluble extract of the twigs of Aglaia rubiginosa, using human oral epidermoid carcinoma (KB) cells as a monitor, led to the isolation of a new naturally occurring cyclopenta[b]benzofuran, 1-O-acetylrocaglaol (1), along with seven known compounds, methyl rocaglate (2), rocagloic acid (3), 1-O-acetylmethyl rocaglate (4), desyclamide, eryodictiol, 5-hydroxy-3,7,4'-trimethoxyflavone, and naringenin. A CHCl(3) extract of the leaves of A. rubiginosa yielded the new compound (3S,4R,22R)-cholest-7,24-diene-3,4,22-triol (5), as well as 11 known compounds, including 2 and 4 and cabraleone, dammarelonic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid, (20S,23E)-20,25-dihydroxy-3,4-secodammara-4(28),23-dienoic acid methyl ester, (3beta,4beta,22R)-ergosta-5,24(24')-diene-3,4,22-triol, ocotillone, shoreic acid, beta-sitosterol, and beta-sitosterol glycoside. The structures of 1 and 5 were elucidated by spectral and chemical methods. Isolates were evaluated with a human cancer cell panel, and compounds 1-4 were found to exhibit potent cytotoxic activity.
Assuntos
Aglaia/química , Antineoplásicos Fitogênicos/isolamento & purificação , Benzofuranos/isolamento & purificação , Plantas Medicinais/química , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Benzofuranos/química , Benzofuranos/farmacologia , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Hidroxicolesteróis/química , Hidroxicolesteróis/isolamento & purificação , Hidroxicolesteróis/farmacologia , Indonésia , Células KB , Estrutura Molecular , Folhas de Planta/química , Caules de Planta/química , Estereoisomerismo , Células Tumorais CultivadasRESUMO
Bioactivity-directed fractionation of extracts of two Diospyros maritima bark samples from Indonesia,one collected at sea level in a beach forest in Java and the other collected at a slight elevation away from the sea shore on the island of Lombok, yielded a diverse set of secondary metabolites. The naphthoquinone plumbagin (1), although found in extracts of both specimens, constituted a much larger percentage of the former sample, which also yielded a series of plumbagin dimers, maritinone (2), chitranone (3), and zeylanone (4). The latter sample yielded a new naphthoquinone derivative, (4S)-shinanolone (5), and a new natural product coumarin, 7,8-dimethoxy-6-hydroxycoumarin (6), along with three other analogues of plumbagin, 2-methoxy-7-methyljuglone (7), 3-methoxy-7-methyljuglone (8), and 7-methyljuglone (9). The structures of compounds 5 and 6 were elaborated by physical, spectral, and chemical methods. All of the isolates were evaluated in both cytotoxicity and antimicrobial assays, and structure-activity relationships of these naphthoquinones are proposed. Plumbagin (1) and maritinone (2) were evaluated also for in vivo antitumor activity in the hollow fiber assay, but both were found to be inactive.