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Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
KAUST Global Academic Partnership Program, Division of Life Science, The Hong Kong University of Science and Technology, Clear Water Bay, Hong Kong, China
Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, Ministry of Education, School of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin 541004, China
School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, China
Netherlands Centre for Biodiversity Naturalis, P.O. Box 9517, Leiden 2300 RA, The Netherlands
* Authors to whom correspondence should be addressed.
Received: 20 November 2011; in revised form: 19 December 2011 / Accepted: 22 December 2011 / Published: 19 January 2012
Abstract: Four new bisabolane-type sesquiterpenoids, aspergiterpenoid A (1), (−)-sydonol (2), (−)-sydonic acid (3), and (−)-5-(hydroxymethyl)-2-(2′,6′,6′-trimethyltetrahydro-2H- pyran-2-yl)phenol (4) together with one known fungal metabolite (5) were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated from the sponge Xestospongia testudinaria collected from the South China Sea. Four of them (1–4) are optically active compounds. Their structures and absolute configurations were elucidated by using NMR spectroscopic techniques and mass spectrometric analysis, and by comparing their optical rotations with those related known analogues. Compounds 1–5 showed selective antibacterial activity against eight bacterial strains with the MIC (minimum inhibiting concentrations) values between 1.25 and 20.0 µM. The cytotoxic, antifouling, and acetylcholinesterase inhibitory activities of these compounds were also examined.
Keywords: bisabolane-type sesquiterpenoid; antibacterial; sponge-derived fungus; Aspergillus sp.
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Li, D.; Xu, Y.; Shao, C.-L.; Yang, R.-Y.; Zheng, C.-J.; Chen, Y.-Y.; Fu, X.-M.; Qian, P.-Y.; She, Z.-G.; Voogd, N.J.; Wang, C.-Y. Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.. Mar. Drugs 2012, 10, 234-241.
Li D, Xu Y, Shao C-L, Yang R-Y, Zheng C-J, Chen Y-Y, Fu X-M, Qian P-Y, She Z-G, Voogd NJ, Wang C-Y. Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.. Marine Drugs. 2012; 10(1):234-241.
Li, Dan; Xu, Ying; Shao, Chang-Lun; Yang, Rui-Yun; Zheng, Cai-Juan; Chen, Yi-Yan; Fu, Xiu-Mei; Qian, Pei-Yuan; She, Zhi-Gang; Voogd, Nicole J. de; Wang, Chang-Yun. 2012. "Antibacterial Bisabolane-Type Sesquiterpenoids from the Sponge-Derived Fungus Aspergillus sp.." Mar. Drugs 10, no. 1: 234-241.