Samholides, swinholide-related metabolites from a marine cyanobacterium cf. Phormidium sp

TitleSamholides, swinholide-related metabolites from a marine cyanobacterium cf. Phormidium sp
Publication TypeJournal Article
Year of Publication2018
AuthorsTao Y.W, Li P.L, Zhang D.J, Glukhov E., Gerwick L, Zhang C., Murray T.F, Gerwick WH
JournalJournal of Organic Chemistry
Volume83
Pagination3034-3046
Date Published2018/03
Type of ArticleArticle
ISBN Number0022-3263
Accession NumberWOS:000428002800003
Keywordschemistry; congeners; cytotoxic dimeric macrolides; isoswinholide-a; natural-products; origin; resistance; scytophycins; seco acid; sponge theonella-swinhoei; tolytoxin
Abstract

Cancer cell cytotoxicity was used to guide the isolation of nine new swinholide-related compounds, named samholides A-I (1-9), from an American Samoan marine cyanobacterium cf. Phormidium sp. Their structures were determined by extensive analysis of 1D and 2D NMR spectroscopic data. The new compounds share an unusual 20-demethyl 44-membered lactone ring composed of two monomers, and they demonstrate structural diversity arising from geometric isomerization of double bonds, sugar units with unique glyceryl moieties and varied methylation patterns. All of the new samholides were potently active against the H-460 human lung cancer cell line with IC50 values ranging from 170 to 910 nM. The isolation of these new swinholide-related compounds from a marine cyanobacterium reinvigorates questions concerning the evolution and biosynthetic origin of these natural products.

DOI10.1021/acs.joc.8b00028
Short TitleJ. Org. Chem.
Student Publication: 
No
Research Topics: 
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