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

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• 作者：Xuan Cuong Nguyen ; Arlette Longeon ; Van Cuong Pham ; F茅lix Urvois ; Christine Bressy ; Thi Thanh Van Trinh ; Hoai Nam Nguyen ; Van Kiem Phan ; Van Minh Chau ; Jean-Fran莽ois Briand ; Marie-Lise Bourguet-Kondracki
• 刊名：Journal of Natural Products
• 出版年：2013
• 出版时间：July 26, 2013
• 年：2013
• 卷：76
• 期：7
• 页码：1313-1318
• 全文大小：262K
• 年卷期：v.76,no.7(July 26, 2013)
• ISSN：1520-6025

文摘

Three new C₂₉ 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尾-hydroxypetrosterol (5b), were isolated from the Vietnamese marine sponge Xestospongia testudinaria, along with the known compounds, aragusterol B (2), xestokerol A (3), 7伪-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.