RESUMO
Acylation of 3-O-angeloylingenol (1) with vinyl acetate, vinyl decanoate and vinyl cinnamate, catalyzed by Candida antarctica Lipase B, was investigated. In each case, compound 1 was quantitatively and regioselectively acylated to afford a single product, 3-O-angeloyl-20-O-acetylingenol (1a), 3-O-angeloyl-20-O-decanoylingenol (1b) and 3-O-angeloyl-20-O-cinnamoylingenol (1c), respectively. The structures of the novel compounds 1b-1c were determined by MS and NMR, and product 1a by comparison of RP-HPLC and TLC with a standard. Compounds 1b-1c induced a bipolar morphology of MM96L melanoma cells at a similar concentration as compound 1, as well as having activity in inhibiting the growth of MM96L melanoma cells.
Assuntos
Antineoplásicos Fitogênicos/metabolismo , Diterpenos/metabolismo , Euphorbia/química , Lipase/metabolismo , Melanoma/tratamento farmacológico , Extratos Vegetais/metabolismo , Acilação , Antineoplásicos Fitogênicos/farmacologia , Antineoplásicos Fitogênicos/uso terapêutico , Linhagem Celular Tumoral , Diterpenos/farmacologia , Diterpenos/uso terapêutico , Proteínas Fúngicas , Humanos , Extratos Vegetais/farmacologia , Extratos Vegetais/uso terapêutico , Compostos de Vinila/metabolismoRESUMO
Two new cyclopeptides, leiocyclocin C (1) and D (2), were isolated from the seeds of Goniothalamus leiocarpus (Annonaceae). Their structures were determined as cyclo-(Gly1-Ser-Pro2-Tyr2-Gly2-Tyr1-Pro1-Pro3) and cyclo-(Gly1-Leu-Pro1-Gly2-Phe-Tyr-Pro2), respectively, by means of spectral and chemical methods.
