Puupehenone congeners from an indo-pacific hyrtios sponge.
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.
Piña
Ivette C
IC
Department of Chemistry and Biochemistry, and Institute of Marine Sciences, University of California, Santa Cruz, California 95064, USA.
Sanders
Miranda L
ML
Crews
Phillip
P
D000818:Animals; D003110:Colonic Neoplasms; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007214:Indonesia; D007938:Leukemia; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry* / Q000145:classification; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism; D014407:Tumor Cells, Cultured / Q000187:drug effects; D044004:Xanthones
D012717:Sesquiterpenes; D044004:Xanthones; C053594:puupehenone