title: Lagunamide C, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Lyngbya majuscula.
abstract: Lagunamide C (1) is a cytotoxic cyclodepsipeptide isolated from the marine cyanobacterium, Lyngbya majuscula, from the western lagoon of Pulau Hantu Besar, Singapore. The complete structural characterization of the molecule was achieved by extensive NMR spectroscopic analysis as well as chemical manipulations. Several methods, including the advanced Marfey's method, a modified method based on derivatization with Mosher's reagents and analysis using LC-MS, and the use of (3)J(H-H) coupling constant values, were utilized for the determination of its absolute configuration. Compound 1 is related to the aurilide-class of molecules and it differs mainly in the macrocyclic structure by having a 27 membered ring system due to additional methylene carbon in the polyketide moiety. Lagunamide C displayed potent cytotoxic activity against a panel of cancer cell lines, such as P388, A549, PC3, HCT8, and SK-OV3 cell lines, with IC(50) values ranging from 2.1 nM to 24.4 nM. Compound 1 also displayed significant antimalarial activity with IC(50) value of 0.29 μM when tested against Plasmodium falciparum. In addition, lagunamide C exhibited weak anti-swarming activity when tested at 100 ppm against the Gram-negative bacterial strain, Pseudomonas aeruginosa PA01.
authors: Natural Sciences and Science Education, National Institute of Education, Nanyang Technological University, Singapore, Singapore.
authors: Ashootosh
authors: A
authors: Tripathi
authors: Jonathan
authors: J
authors: Puddick
authors: Michele R
authors: MR
authors: Prinsep
authors: Matthias
authors: M
authors: Rottmann
authors: Kok Ping
authors: KP
authors: Chan
authors: David Yu-Kai
authors: DY
authors: Chen
authors: Lik Tong
authors: LT
authors: Tan
mesh_terms: D045744:Cell Line, Tumor; D000458:Cyanobacteria / Q000737:chemistry*; D047630:Depsipeptides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D008235:Lyngbya Toxins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects; D011550:Pseudomonas aeruginosa / Q000187:drug effects
chemical_list: D047630:Depsipeptides; D008235:Lyngbya Toxins; C574190:lagunamide C