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 journalArticlepeer-review

9 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 M, respectively. In contrast, compounds 1, 3 and 4 were inactive, with IC50 values greater than 50 M. 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 - Apr 18 2015

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Plant Science
  • Organic Chemistry

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