Kalkipyrone B, a marine cyanobacterial gamma-pyrone possessing cytotoxic and anti-fungal activities

TitleKalkipyrone B, a marine cyanobacterial gamma-pyrone possessing cytotoxic and anti-fungal activities
Publication TypeJournal Article
Year of Publication2016
AuthorsBertin M.J, Demirkiran O., Navarro G., Moss N.A, Lee J., Goldgof G.M, Vigil E., Winzeler E.A, Valeriote F.A, Gerwick WH
JournalPhytochemistry
Volume122
Pagination113-118
Date Published2016/02
Type of ArticleArticle
ISBN Number0031-9422
Accession NumberWOS:000369460200011
Keywordsactinopyrone-b; analogs; cells; cyanobacteria; drug discovery; Kalkipyrone; Leptolyngbya; lyngbya-majuscula; Moorea; natural-products; physiologically active substances; polyketide; Schizothrix; Yoshinone
Abstract

Bioassay-guided fractionation of two marine cyanobacterial extracts using the H-460 human lung cancer cell line and the OVC-5 human ovarian cancer cell line led to the isolation of three related alpha-methoxy-beta, beta'-dimethyl-gamma-pyrones each containing a modified alkyl chain, one of which was identified as the previously reported kalkipyrone and designated kalkipyrone A. The second compound was an analog designated kalkipyrone B. The third was identified as the recently reported yoshinone A, also isolated from a marine cyanobacterium. Kalkipyrone A and B were obtained from a field-collection of the cyanobacterium Leptolyngbya sp. from Fagasa Bay, American Samoa, while yoshinone A was isolated from a field-collection of cyanobacteria (cf. Schizothrix sp.) from Panama. One-dimensional and twodimensional NMR experiments were used to determine the overall structures and relative configurations of the kalkipyrones, and the absolute configuration of kalkipyrone B was determined by H-1 NMR analysis of diastereomeric Mosher's esters. Kalkipyrone A showed good cytotoxicity to H-460 human lung cancer cells (EC50 = 0.9 mu M), while kalkipyrone B and yoshinone A were less active (EC50 = 9.0 mu M and >10 mu M, respectively). Both kalkipyrone A and B showed moderate toxicity to Saccharomyces cerevisiae ABC16-Monster strain (IC50 = 14.6 and 13.4 mu M, respectively), whereas yoshinone A was of low toxicity to this yeast strain (IC50 = 63.8 mu M). (C) 2015 Elsevier Ltd. All rights reserved.

DOI10.1016/j.phytochem.2015.11.011
Short TitlePhytochemistry
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