2,3-Seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens |
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| Authors: | Diaa T.A. Youssef Lamiaa A. Shaala Gamal A. Mohamed Sabrin R.M. Ibrahim Zainy M. Banjar Jihan M. Badr |
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| Affiliation: | 1. Department of Natural Products, Faculty of Pharmacy, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia;2. Natural Products Unit, King Fahd Medical Research Center, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia;3. Suez Canal Hospital, Suez Canal University, Ismailia 41522, Egypt;4. Department of Pharmacognosy, Faculty of Pharmacy, Al-Azhar University, Assiut Branch, Assiut 71524, Egypt;5. Department of Pharmacognosy, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt;6. Department of Clinical Biochemistry, Faculty of Medicine, King Abdulaziz University, Jeddah 21589, Kingdom of Saudi Arabia;7. Department of Pharmacognosy, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt |
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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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| Keywords: | Red Sea cyanobacterium Moorea producens 2,3-seco-2,3-dioxolyngbyatoxin A lyngbyatoxin HeLa cells antiproliferative activity |
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