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

Handle URI:
http://hdl.handle.net/10754/600224
Title:
Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus
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
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.
Citation:
Shao C-L, Wu H-X, Wang C-Y, Liu Q-A, Xu Y, et al. (2011) Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus . Journal of Natural Products 74: 629–633. Available: http://dx.doi.org/10.1021/np100641b.
Publisher:
American Chemical Society (ACS)
Journal:
Journal of Natural Products
Issue Date:
25-Apr-2011
DOI:
10.1021/np100641b
PubMed ID:
21348465
Type:
Article
ISSN:
0163-3864; 1520-6025
Sponsors:
This work was supported by the National Natural Science Foundation of China (Nos. 30901879; 40976077; 40776073), the Research Fund for the Doctoral Program of Higher Education, Ministry of Education of China (No. 20090132110002), and the Basic Research Program of Science and Technology, Ministry of Science and Technology of China (No. 2007FY210500).
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Publications Acknowledging KAUST Support

Full metadata record

DC FieldValue Language
dc.contributor.authorShao, Chang Lunen
dc.contributor.authorWu, Hui Xianen
dc.contributor.authorWang, Chang Yunen
dc.contributor.authorLiu, Qing Aien
dc.contributor.authorXu, Yingen
dc.contributor.authorWei, Mei Yanen
dc.contributor.authorQian, Pei Yuanen
dc.contributor.authorGu, Yu Chengen
dc.contributor.authorZheng, Cai Juanen
dc.contributor.authorShe, Zhi Gangen
dc.contributor.authorLin, Yong Chengen
dc.date.accessioned2016-02-28T07:59:25Zen
dc.date.available2016-02-28T07:59:25Zen
dc.date.issued2011-04-25en
dc.identifier.citationShao C-L, Wu H-X, Wang C-Y, Liu Q-A, Xu Y, et al. (2011) Potent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatus . Journal of Natural Products 74: 629–633. Available: http://dx.doi.org/10.1021/np100641b.en
dc.identifier.issn0163-3864en
dc.identifier.issn1520-6025en
dc.identifier.pmid21348465en
dc.identifier.doi10.1021/np100641ben
dc.identifier.urihttp://hdl.handle.net/10754/600224en
dc.description.abstractThree 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.en
dc.description.sponsorshipThis work was supported by the National Natural Science Foundation of China (Nos. 30901879; 40976077; 40776073), the Research Fund for the Doctoral Program of Higher Education, Ministry of Education of China (No. 20090132110002), and the Basic Research Program of Science and Technology, Ministry of Science and Technology of China (No. 2007FY210500).en
dc.publisherAmerican Chemical Society (ACS)en
dc.titlePotent Antifouling Resorcylic Acid Lactones from the Gorgonian-Derived Fungus Cochliobolus lunatusen
dc.typeArticleen
dc.identifier.journalJournal of Natural Productsen
dc.contributor.institutionKey Laboratory of Marine Drugs, Ministry of Education of China, Ocean University of China, Qingdao 266003, Chinaen
dc.contributor.institutionKey Laboratory of Exploration and Utilization of Aquatic Genetic Resources, Ministry of Education, Shanghai Ocean University, Shanghai 201306, Chinaen
dc.contributor.institutionSchool of Pharmacy, Guangdong Medical College, Dongguan 523808, Chinaen
dc.contributor.institutionSyngenta, Jealott's Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, United Kingdomen
dc.contributor.institutionSchool of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, Chinaen
kaust.authorWu, Hui-Xianen
kaust.authorXu, Yingen
kaust.authorQian, Pei-Yuanen
kaust.grant.programKAUST Global Partnership Programen

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