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 language | English (US) |
---|---|
Pages (from-to) | 703-709 |
Number of pages | 7 |
Journal | Natural Product Research |
Volume | 29 |
Issue number | 8 |
DOIs | |
State | Published - 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)