Antifouling 26,27-Cyclosterols from the Vietnamese Marine Sponge Xestospongia testudinaria

作者：Xuan Cuong Nguyen; Longeon Arlette; Van Cuong Pham; Urvois Felix; Bressy Christine; Thi Thanh Van Trinh; Hoai Nam Nguyen; Van Kiem Phan; Van Minh Chau; Briand Jean Francois; Bourguet Kondracki Marie Lise^*

来源：Journal of Natural Products, 2013, 76(7): 1313-1318.

DOI：10.1021/np400288j

Three new C-29 sterols with a cyclopropane ring cyclized between C-26 and C-27 of the side chain, aragusterol I (1), 21-O-octadecanoyl-xestokerol A (4), and 7 beta-hydroxypetrosterol (5b), were isolated from the Vietnamese marine sponge Xestospongia testudinaria, along with the known compounds, aragusterol B (2), xestokerol A (3), 7 alpha-hydroxypetrosterol (5a), 7-oxopetrosterol (6), and petrosterol (7). The structures of the new compounds were established by analysis of spectroscopic data including 1D and 2D NMR, and high-resolution electrospray ionization mass spectrometry (HRESIMS). Their capacity to inhibit the adhesion of isolated bacteria from marine biofilms was evaluated against the bacterial strains Pseudoalteromonas sp. D41, Pseudoalteromonas sp. TC8, and Polaribacter sp. TC5. Aragusterol B (2) and 21-O-octadecanoyl-xestokerol A (4) exhibited the most potent antifouling activity with EC50 values close to these reported in the literature for tributyltin oxide, a marine anti-biofouling agent now considered to be a severe marine pollutant. Due to its comparable activity to tributyltin oxide and its absence of toxicity, the new 26,27-cyclosterol, 21-O-octadecanoyl-xestokerol A (4) constitutes a promising scaffold for further investigations.

• 出版日期2013-7