Isolation, antimicrobial activity, and absolute configuration of the furylidene tetronic acid core of pestalotic acids A-G

Natural products possessing the 3-(furan-2(5H)-ylidene)furan-2,4(3H,5H)-dione (furylidene tetronic acid) skeleton are rare and were encountered only as fungal metabolites. The configurational assignment of the furylidene tetronic acid core using conventional approaches remained a challenge. Pestalot...

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Veröffentlicht in:Organic & biomolecular chemistry 2012-07, Vol.10 (27), p.5307-5314
Hauptverfasser: Zhang, Fan, Ding, Gang, Li, Li, Cai, Xiaoyue, Si, Yikang, Guo, Liangdong, Che, Yongsheng
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Sprache:eng
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Zusammenfassung:Natural products possessing the 3-(furan-2(5H)-ylidene)furan-2,4(3H,5H)-dione (furylidene tetronic acid) skeleton are rare and were encountered only as fungal metabolites. The configurational assignment of the furylidene tetronic acid core using conventional approaches remained a challenge. Pestalotic acids A-G (1-7) are new furylidene tetronic acid derivatives isolated from a plant endophyte Pestalotiopsis yunnanensis. The structure of 1 was elucidated by combination of NMR experiments, X-ray crystallography, and ECD calculations. Compounds 3 and 7 showed significant antimicrobial activity.
ISSN:1477-0520
1477-0539
DOI:10.1039/c2ob25469g