Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp.

Yiwen Tao, Pinglin Li, Daojing Zhang, Evgenia Glukhov, Lena Gerwick, Chen Zhang, Thomas F. Murray, William H. Gerwick

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)3034-3046
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number6
DOIs
StatePublished - Mar 16 2018

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Metabolites
Cells
Methylation
Lactones
Cytotoxicity
Isomerization
Biological Products
Sugars
Monomers
Nuclear magnetic resonance
Cyanobacteria

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Tao, Y., Li, P., Zhang, D., Glukhov, E., Gerwick, L., Zhang, C., ... Gerwick, W. H. (2018). Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp. Journal of Organic Chemistry, 83(6), 3034-3046. https://doi.org/10.1021/acs.joc.8b00028

Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp. / Tao, Yiwen; Li, Pinglin; Zhang, Daojing; Glukhov, Evgenia; Gerwick, Lena; Zhang, Chen; Murray, Thomas F.; Gerwick, William H.

In: Journal of Organic Chemistry, Vol. 83, No. 6, 16.03.2018, p. 3034-3046.

Research output: Contribution to journalArticle

Tao, Y, Li, P, Zhang, D, Glukhov, E, Gerwick, L, Zhang, C, Murray, TF & Gerwick, WH 2018, 'Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp.', Journal of Organic Chemistry, vol. 83, no. 6, pp. 3034-3046. https://doi.org/10.1021/acs.joc.8b00028
Tao, Yiwen ; Li, Pinglin ; Zhang, Daojing ; Glukhov, Evgenia ; Gerwick, Lena ; Zhang, Chen ; Murray, Thomas F. ; Gerwick, William H. / Samholides, Swinholide-Related Metabolites from a Marine Cyanobacterium cf. Phormidium sp. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 6. pp. 3034-3046.
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