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- Title
Benderamide A, a Cyclic Depsipeptide from a Singapore Collection of Marine Cyanobacterium cf. Lyngbya sp.
- Authors
Ding, Chi Ying Gary; Ong, Ji Fa Marshall; Tan, Lik Tong; Goh, Hui Chin; Coffill, Cynthia R.
- 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.
- Subjects
LYNGBYA; DEPSIPEPTIDES; MARINE biology; ALGORITHMS; COMPARATIVE studies; NUCLEAR magnetic resonance
- Publication
Marine Drugs, 2018, Vol 16, Issue 11, p409
- ISSN
1660-3397
- Publication type
Article
- DOI
10.3390/md16110409