title: Potent antifouling resorcylic acid lactones from the gorgonian-derived fungus Cochliobolus lunatus.
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 CDCl(3) 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.
authors.affiliation: Key Laboratory of Marine Drugs, The Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, People's Republic of China.
authors.forename: Chang-Lun
authors.initials: CL
authors.lastname: Shao
authors.forename: Hui-Xian
authors.initials: HX
authors.lastname: Wu
authors.forename: Chang-Yun
authors.initials: CY
authors.lastname: Wang
authors.forename: Qing-Ai
authors.initials: QA
authors.lastname: Liu
authors.forename: Ying
authors.initials: Y
authors.lastname: Xu
authors.forename: Mei-Yan
authors.initials: MY
authors.lastname: Wei
authors.forename: Pei-Yuan
authors.initials: PY
authors.lastname: Qian
authors.forename: Yu-Cheng
authors.initials: YC
authors.lastname: Gu
authors.forename: Cai-Juan
authors.initials: CJ
authors.lastname: Zheng
authors.forename: Zhi-Gang
authors.initials: ZG
authors.lastname: She
authors.forename: Yong-Cheng
authors.initials: YC
authors.lastname: Lin
mesh_terms: D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry*; D001412:Bacillus subtilis / Q000187:drug effects; D057219:Biofouling / Q000517:prevention & control; D004354:Drug Screening Assays, Antitumor; D004926:Escherichia coli / Q000187:drug effects; D056945:Hep G2 Cells; D006801:Humans; D062385:Hydroxybenzoates; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D007814:Larva / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008837:Micrococcus / Q000187:drug effects; D015394:Molecular Structure; D013211:Staphylococcus aureus / Q000187:drug effects; D001468:Thoracica / Q000737:chemistry*
chemical_list: D000900:Anti-Bacterial Agents; D000970:Antineoplastic Agents; D062385:Hydroxybenzoates; C118715:LL Z1640-2; D007783:Lactones; C559005:cochliomycin A; C559006:cochliomycin B; C559007:cochliomycin C