A new cacospongionolide derivative from the sponge Fasciospongia cavernosa.
Cacospongionolide F (4a), a new bioactive cacospongionolide-related sesterterpene, has been isolated from the Northern Adriatic sponge Fasciospongia cavernosa. The structure was proposed on the basis of spectroscopic data and chemical transformations. The absolute configuration was established using the modified Mosher's method. A molecular mechanics study of the dehydrodecalin ring explained the observed differences in dynamic behavior between cacospongionolide F and mamanuthaquinone, a related compound. Antimicrobial activity, brine shrimp and fish lethalities of this new compound are reported.
De Rosa
S
S
Istituto per la Chimica di Molecole di Interesse Biologico CNR, Via Toiano 6, 80072 Arco Felice (Napoli), Italy. sdr@sdr.icmib.na.cnr.it
Crispino
A
A
De Giulio
A
A
Iodice
C
C
Amodeo
P
P
Tancredi
T
T
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D011714:Pyrans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013057:Spectrum Analysis
D000890:Anti-Infective Agents; D011714:Pyrans; C098384:cacospongionolide B; D015107:4-Butyrolactone