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

• Published in: Journal of natural products (Washington, D.C.) Vol. 74; no. 4; pp. 629 - 633
• Main Authors: Shao, Chang-Lun, Wu, Hui-Xian, Wang, Chang-Yun, Liu, Qing-Ai, Xu, Ying, Wei, Mei-Yan, Qian, Pei-Yuan, Gu, Yu-Cheng, Zheng, Cai-Juan, She, Zhi-Gang, Lin, Yong-Cheng
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 25.04.2011; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Animals; Anthozoa - chemistry; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Ascomycota - chemistry; Bacillus subtilis - drug effects; Biofouling - prevention & control; Biological and medical sciences; Chemistry, Medicinal; Drug Screening Assays, Antitumor; Escherichia coli - drug effects; General pharmacology; Hep G2 Cells; Humans; Hydroxybenzoates; Lactones - chemistry; Lactones - isolation & purification; Lactones - pharmacology; Larva - drug effects; Life Sciences & Biomedicine; Medical sciences; Microbial Sensitivity Tests; Micrococcus - drug effects; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Science & Technology; Staphylococcus aureus - drug effects; Thoracica - chemistry; South China Sea; HYPOTHEMYCIN; MACROLIDES; METABOLITES; Ascomycota; Human; Liver; Lung; Animal origin; Cytotoxicity; Lactone; Tricyclic compound; Biological activity; Cochliobolus lunatus; Macrocycle; Fungi; Marine environment; Coelenterata; Cell line; Hepatocyte; Antifouling protection; Cnidaria; Isolation; Invertebrata; Tumor cell; Structural analysis
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/np100641b

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.