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Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China
Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Hainan Normal University, Haikou 571158, China
Guangxi Key Laboratory of Marine Biotechnology, Guangxi Institute of Oceanology, Beihai 536000, China
* Authors to whom correspondence should be addressed.
Received: 1 April 2013; in revised form: 10 May 2013 / Accepted: 14 May 2013 / Published: 10 June 2013
Abstract: One new phenylalanine derivative 4′-OMe-asperphenamate (1), along with one known phenylalanine derivative (2) and two new cytochalasins, aspochalasin A1 (3) and cytochalasin Z24 (4), as well as eight known cytochalasin analogues (5–12) were isolated from the fermentation broth of Aspergillus elegans ZJ-2008010, a fungus obtained from a soft coral Sarcophyton sp. collected from the South China Sea. Their structures and the relative configurations were elucidated using comprehensive spectroscopic methods. The absolute configuration of 1 was determined by chemical synthesis and Marfey’s method. All isolated metabolites (1–12) were evaluated for their antifouling and antibacterial activities. Cytochalasins 5, 6, 8 and 9 showed strong antifouling activity against the larval settlement of the barnacle Balanus amphitrite, with the EC50 values ranging from 6.2 to 37 μM. This is the first report of antifouling activity for this class of metabolites. Additionally, 8 exhibited a broad spectrum of antibacterial activity, especially against four pathogenic bacteria Staphylococcus albus, S. aureus, Escherichia coli and Bacillus cereus.
Keywords: soft coral-derived fungus; Aspergillus elegans; phenylalanine derivative; cytochalasin; antifouling
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MDPI and ACS Style
Zheng, C.-J.; Shao, C.-L.; Wu, L.-Y.; Chen, M.; Wang, K.-L.; Zhao, D.-L.; Sun, X.-P.; Chen, G.-Y.; Wang, C.-Y. Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans. Mar. Drugs 2013, 11, 2054-2068.
Zheng C-J, Shao C-L, Wu L-Y, Chen M, Wang K-L, Zhao D-L, Sun X-P, Chen G-Y, Wang C-Y. Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans. Marine Drugs. 2013; 11(6):2054-2068.
Zheng, Cai-Juan; Shao, Chang-Lun; Wu, Lu-Yong; Chen, Min; Wang, Kai-Ling; Zhao, Dong-Lin; Sun, Xue-Ping; Chen, Guang-Ying; Wang, Chang-Yun. 2013. "Bioactive Phenylalanine Derivatives and Cytochalasins from the Soft Coral-Derived Fungus, Aspergillus elegans." Mar. Drugs 11, no. 6: 2054-2068.