TY - JOUR
T1 - 2,3-Seco-2,3-dioxo-lyngbyatoxin A from a Red Sea strain of the marine cyanobacterium Moorea producens
AU - Youssef, Diaa T.A.
AU - Shaala, Lamiaa A.
AU - Mohamed, Gamal A.
AU - Ibrahim, Sabrin R.M.
AU - Banjar, Zainy M.
AU - Badr, Jihan M.
AU - McPhail, Kerry L.
AU - Risinger, April L.
AU - Mooberry, Susan L.
N1 - Publisher Copyright:
© 2015 Taylor and Francis.
PY - 2015/4/18
Y1 - 2015/4/18
N2 - 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.
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 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.
UR - https://www.scopus.com/pages/publications/84930702235
UR - https://www.scopus.com/pages/publications/84930702235#tab=citedBy
U2 - 10.1080/14786419.2014.982647
DO - 10.1080/14786419.2014.982647
M3 - Article
C2 - 25421266
AN - SCOPUS:84930702235
SN - 1478-6419
VL - 29
SP - 703
EP - 709
JO - Natural Product Research
JF - Natural Product Research
IS - 8
ER -