Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus

Chang Lun Shao, Hui Xian Wu, Chang Yun Wang, Qing Ai Liu, Ying Xu, Mei Yan Wei, Pei-Yuan Qian, Yu Cheng Gu, Cai Juan Zheng, Zhi Gang She, Yong Cheng Lin

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134 Scopus citations

Abstract

Three new 14-membered resorcylic acid lactones, two with a rare natural acetonide group and one with a 5-chloro-substituted lactone, named cochliomycins A-C (1-3), together with four known analogues, zeaenol (4), LL-Z1640-1 (5), LL-Z1640-2 (6), and paecilomycin F (7), were isolated from the culture broth of Cochliobolus lunatus, a fungus obtained from the gorgonian Dichotella gemmacea collected in the South China Sea. Their structures and the relative configurations of 1-3 were elucidated using comprehensive spectroscopic methods including NOESY spectra and chemical conversions. A transetherification reaction was also observed in which cochliomycin B (2) in a solution of CDCl3 slowly rearranged to give cochliomycin A (1) at room temperature. These resorcylic acid lactones were evaluated against the larval settlement of barnacle Balanus amphitrite, and antifouling activity was detected for the first time for this class of metabolites. The antibacterial and cytotoxic activities of these compounds were also examined. © 2011 The American Chemical Society and American Society of Pharmacognosy.
Original languageEnglish (US)
Pages (from-to)629-633
Number of pages5
JournalJournal of Natural Products
Volume74
Issue number4
DOIs
StatePublished - Apr 25 2011
Externally publishedYes

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