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1.
J Nat Prod ; 66(1): 2-6, 2003 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-12542334

RESUMO

An investigation of the constituents from an Indonesian Hyrtios sponge has provided new insights about the chemistry and biology of the puupehenones, a unique class of merosesquiterpenes. The parent compound, puupehenone (2), has been repeatedly encountered in sponges from four distinct orders. In this study we characterized three compounds, (+)-(5S,8S,9R,10S)-20-methoxypuupehenone (3), (+)-(5S,8S,10S)-20-methoxy-9,15-ene-puupehenol (4), and (+)-(5S,8S,9R,10S)-15,20-dimethoxypuupehenol (5). Their structures were supported by complete sets of spectroscopic data along with comparisons to literature properties. While 5 was observed in the crude extracts, it was also heat labile and could be converted at 35 degrees C to a mixture of 3 and 4. The possibility that 3, 4, and 5 are formed from 2 by a series of methanol additions is discussed. The bioactivity of these compounds in soft-agar cytotoxicity tests was also explored.


Assuntos
Poríferos/química , Sesquiterpenos/isolamento & purificação , Xantonas , Animais , Neoplasias do Colo , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Indonésia , Leucemia , Camundongos , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Poríferos/classificação , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Estereoisomerismo , Células Tumorais Cultivadas/efeitos dos fármacos
2.
J Org Chem ; 68(10): 3866-73, 2003 May 16.
Artigo em Inglês | MEDLINE | ID: mdl-12737565

RESUMO

Four novel bisulfide bromotyrosine derivatives, psammaplins E (9), F (10), G (11), and H (12), and two new bromotyrosine derivatives, psammaplins I (13) and J (14), were isolated from the sponge Pseudoceratina purpurea, along with known psammaplins A (4), B (6), C (7), and D (8) and bisaprasin (5). The structures of psammaplins E (9) and F (10), which each contain an oxalyl group rarely found in marine organisms, were determined by spectroscopic analysis. Compounds 4, 5, and 10 are potent histone deacetylase inhibitors and also show mild cytotoxicity. Furthermore, compounds 4, 5, and 11 are potent DNA methyltransferase inhibitors. The biogenetic pathway previously proposed for the psammaplins class is also revisited.


Assuntos
Metilases de Modificação do DNA/antagonistas & inibidores , Dissulfetos/isolamento & purificação , Inibidores Enzimáticos/isolamento & purificação , Inibidores de Histona Desacetilases , Poríferos/química , Ésteres do Ácido Sulfúrico/isolamento & purificação , Tirosina/análogos & derivados , Tirosina/isolamento & purificação , Animais , Dissulfetos/química , Dissulfetos/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Estrutura Molecular , Ressonância Magnética Nuclear Biomolecular , Papua Nova Guiné , Ésteres do Ácido Sulfúrico/química , Ésteres do Ácido Sulfúrico/farmacologia , Tirosina/química , Tirosina/farmacologia
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