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

doi:10.1080/14786419.2014.982647

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

Pharmacology

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	703-709
Number of pages	7
Journal	Natural Product Research
Volume	29
Issue number	8
DOIs	https://doi.org/10.1080/14786419.2014.982647
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)

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2,3-seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens. / Youssef, Diaa T A; Shaala, Lamiaa A.; Mohamed, Gamal A.; Ibrahim, Sabrin R M; Banjar, Zainy M.; Badr, Jihan M.; McPhail, Kerry L.; Risinger, April L ; Mooberry, Susan L.

In: Natural Product Research, Vol. 29, No. 8, 2015, p. 703-709.

Research output: Contribution to journal › Article › peer-review

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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.",

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AB - 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.

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