Antimalarial Isocyano and Isothiocyanato Sesquiterpenes with Tri- and Bicyclic Skeletons from the Nudibranch Phyllidia ocellata.
J Nat Prod
; 78(6): 1422-7, 2015 Jun 26.
Article
en En
| MEDLINE
| ID: mdl-26056748
ABSTRACT
Five new isocyano/isothiocyanato sesquiterpenes (1-5) with tri- or bicyclic carbon skeletons have been characterized from Australian specimens of the nudibranch Phyllidia ocellata. Spectroscopic analyses at 900 MHz were informed by DFT calculations. The 1S, 5S, 8R configuration of 2-isocyanoclovene (1) was determined by X-ray crystallographic analysis of formamide 6. A biosynthetic pathway to clovanes 1 and 2 from epicaryolane precursors is proposed. Isocyanides 1, 2, and 4 showed activity against Plasmodium falciparum (IC50 0.26-0.30 µM), while isothiocyanate 3 and formamide 6 had IC50 values of >10 µM.
Texto completo:
1
Banco de datos:
MEDLINE
Asunto principal:
Plasmodium falciparum
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Sesquiterpenos
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Isotiocianatos
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Isocianatos
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Gastrópodos
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Antimaláricos
Límite:
Animals
País como asunto:
Oceania
Idioma:
En
Año:
2015
Tipo del documento:
Article