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Mar. Drugs 2018, 16(11), 409; https://doi.org/10.3390/md16110409

Benderamide A, a Cyclic Depsipeptide from a Singapore Collection of Marine Cyanobacterium cf. Lyngbya sp.

1
Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore
2
p53 Laboratory, Agency for Science, Technology and Research (A*STAR), #06-06, Immunos, 8A Biomedical Grove, Singapore 138648, Singapore
*
Author to whom correspondence should be addressed.
Received: 12 September 2018 / Revised: 18 October 2018 / Accepted: 22 October 2018 / Published: 26 October 2018
(This article belongs to the Special Issue Marine Natural Products Discovery: In Honor of Late Prof. Tatsuo Higa)
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Abstract

Benderamide A (1), a (S)-2,2-dimethyl-3-hydroxy-7-octynoic acid (S-Dhoya)-containing cyclic depsipeptide that belongs to the kulolide superfamily, was isolated from a Singapore collection of cf. Lyngbya sp. marine cyanobacterium using a bioassay-guided approach. While the planar structure of 1 was elucidated using a combination of 1D and 2D NMR experiments and MS analysis, the absolute configuration was subsequently achieved using the results obtained from Marfey’s analysis, comparative analysis of nuclear overhauser effect spectroscopy (NOESY) with the known compound 3, and one dimensional-nuclear overhauser effect (1D-NOE). Although 1 did not display antiproliferative activity against MCF7 breast cancer cells, the presence of an Ala instead of Gly suggests a possible mechanistic pathway to explain the consequential decrease in cytotoxicity compared to the closely related 2. In addition, results obtained from an LC–MS/MS-based molecular networking algorithm revealed two other closely related compounds encouraging further identification and isolation from the same marine cyanobacterium extract. View Full-Text
Keywords: Lyngbya sp.; marine cyanobacterium; cyclic depsipeptide; molecular networking Lyngbya sp.; marine cyanobacterium; cyclic depsipeptide; molecular networking
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Ding, C.Y.G.; Ong, J.F.M.; Goh, H.C.; Coffill, C.R.; Tan, L.T. Benderamide A, a Cyclic Depsipeptide from a Singapore Collection of Marine Cyanobacterium cf. Lyngbya sp.. Mar. Drugs 2018, 16, 409.

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