HIV-Inhibitory cembrane derivatives from a Philippines collection of the soft coral Lobophytum sp.

Mohammed A. Rashid, Kirk R. Gustafson and Michael R. Boyd: J.Nat.Prod. 63: 531-533, 2000.

Abstract:

Bioassay-guided fractionation of an aqueous extract of a Philippine Islands collection of the soft coral Lobophytum sp. concentrated its HIV-inhibitory activity into fractions rich in cembranoid diterpenes. Lobohedleolide (1), (7Z)-lobohedleolide (2), and a new compound, 17-dimethylaminolobohedleolide
(3), were purified from these fractions by HPLC. The structures of compounds 1-3 were elucidated by spectroscopic analyses and by comparison of their spectral data with previously reported values. The relative stereochemistry of the gamma-lactone ring substituents of 3 was determined by 1D NOESY experiments. While several other cembranoids that contain a dimethylamino functional group have been reported from the soft coral Sinularia sp., compound 3 represents the first cembrane diterpene with this functional group isolated from a Lobophytum species. Diterpenoids 1-3 exhibited moderate HIV-inhibitory activity (EC50 approximately 3-5 µg/mL) in a cell-based in vitro anti-HIV assay.

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