2,3-seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens

Diaa T A Youssef, Lamiaa A. Shaala, Gamal A. Mohamed, Sabrin R M Ibrahim, Zainy M. Banjar, Jihan M. Badr, Kerry L. McPhail, April L Risinger, Susan L Mooberry

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

Chemical investigation of the organic extract of a Red Sea strain of the cyanobacterium Moorea producens has afforded 2,3-seco-2,3-dioxo-lyngbyatoxin A (1). Five known compounds including lyngbyatoxin A (2), majusculamides A and B (3 and 4), aplysiatoxin (5) and debromoaplysiatoxin (6) were also isolated. Their structures were elucidated by using HR-FAB-MS, 1D and 2D NMR analyses. The compounds were evaluated for antiproliferative activity against HeLa cancer cells. Lyngbyatoxin A (2) showed potent activity, with an IC50 of 9.2 nM, while 5 and 6 displayed modest activity with IC50 values of 13.3 and 3.03 μM, respectively. In contrast, compounds 1, 3 and 4 were inactive, with IC50 values greater than 50 μM. The lack of cytotoxicity for 2,3-seco-2,3-dioxo-lyngbyatoxin A (1) demonstrates that the indole moiety in lyngbyatoxin (2) is essential for its cytotoxicity, and suggests that detoxification of 2 may be carried out by biological oxidation of the indole moiety to yield 1.

Original languageEnglish (US)
Pages (from-to)703-709
Number of pages7
JournalNatural Product Research
Volume29
Issue number8
DOIs
StatePublished - 2015

Keywords

  • 2,3-seco-2,3-dioxolyngbyatoxin A
  • antiproliferative activity
  • HeLa cells
  • lyngbyatoxin
  • Moorea producens
  • Red Sea cyanobacterium

ASJC Scopus subject areas

  • Medicine(all)

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