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Colletotrichalactones A-Ca, unusual 5/6/10-fused tricyclic polyketides produced by an endophytic fungus, Colletotrichum sp. JS-0361

Authors
Bang, SungheeKwon, Ha EunBaek, Ji YunJang, Dae SikKim, SoonokNam, Sang-JipLee, DonghoKang, Ki SungShim, Sang Hee
Issue Date
12월-2020
Publisher
ACADEMIC PRESS INC ELSEVIER SCIENCE
Keywords
Colletotrichum sp.; Polyketides; 5/6/10-Fused ring system; Cytotoxicity
Citation
BIOORGANIC CHEMISTRY, v.105
Indexed
SCIE
SCOPUS
Journal Title
BIOORGANIC CHEMISTRY
Volume
105
URI
https://scholar.korea.ac.kr/handle/2021.sw.korea/51270
DOI
10.1016/j.bioorg.2020.104449
ISSN
0045-2068
Abstract
Three unusual polyketides with a 5/6/10-fused ring system, named colletotrichalactones A-Ca (1-3a), were isolated from cultures of the endophytic fungus, Colletotrichum sp. JS-0361, which was isolated from a leaf of Morus alba. Their structures, including their absolute stereochemistries, were completely established using extensive spectroscopic methods together with a chemical reaction utilizing competing enantioselective acylation coupled with LC/MS. Compounds possessing this ring skeleton were previously reported in three studies. Our rigorous chemical investigation revealed the complete configuration of this skeleton, which agreed with the results for glabramycin B with this ring skeleton established by computational chemistry and enantioselective synthesis in previous reports. 1 and 2 had unstable aldehyde groups that were easily converted to acetal groups in the presence of solvents. Meanwhile, compound 3a, with terminal acetal functionality, was deduced to be an artefact originating from compound 3 with a terminal aldehyde group. Compounds 1 and 3a displayed moderate to-potent cytotoxic activities against MCF7 cells with IC(50)s of 35.06 and 25.20 mu M, respectively.
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