Antifouling 26,27-Cyclosterols from the Vietnamese Marine Sponge \textitXestospongia testudinaria - Université de Toulon Access content directly
Journal Articles Journal of Natural Products Year : 2013

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

Xuan Cuong Nguyen
  • Function : Author
Arlette Longeon
  • Function : Author
van Cuong Pham
  • Function : Author
Félix Urvois
  • Function : Author
Thi Thanh Van Trinh
  • Function : Author
Hoai Nam Nguyen
  • Function : Author
van Kiem Phan
  • Function : Author
van Minh Chau
  • Function : Author
Marie-Lise Bourguet-Kondracki
  • Function : Author

Abstract

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 7β-hydroxypetrosterol (5b), were isolated from the Vietnamese marine sponge Xestospongia testudinaria, along with the known compounds, aragusterol B (2), xestokerol A (3), 7α-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.
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Dates and versions

hal-01364130 , version 1 (12-09-2016)

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Xuan Cuong Nguyen, Arlette Longeon, van Cuong Pham, Félix Urvois, Christine Bressy, et al.. Antifouling 26,27-Cyclosterols from the Vietnamese Marine Sponge \textitXestospongia testudinaria. Journal of Natural Products, 2013, 76 (7), pp.1313--1318. ⟨10.1021/np400288j⟩. ⟨hal-01364130⟩

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