HIV-inhibitory cembrane derivatives from a Philippines collection of the soft coral Lobophytum species.
Bioassay-guided fractionation of an aqueous extract of a Philippine Islands collection of the soft coralLobophytum 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 (EC(50) approximately 3-5 microg/mL) in a cell-based in vitro anti-HIV assay.
Rashid
M A
MA
Laboratory of Drug Discovery Research and Development, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick Cancer Research and Development Center, Frederick, MD 21702-1201, USA.
Gustafson
K R
KR
Boyd
M R
MR
D000818:Animals; D019380:Anti-HIV Agents / Q000302:isolation & purification* / Q000494:pharmacology; D001643:Bridged Bicyclo Compounds / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003063:Cnidaria / Q000737:chemistry*; D005663:Furans / Q000302:isolation & purification* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010679:Philippines; D013056:Spectrophotometry, Ultraviolet
C409628:17-dimethylaminolobohedleolide; D019380:Anti-HIV Agents; D001643:Bridged Bicyclo Compounds; D005663:Furans; C409627:lobohedleolide