Lagunamide C, a cytotoxic cyclodepsipeptide from the marine cyanobacterium Lyngbya majuscula |
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| Authors: | Tripathi Ashootosh Puddick Jonathan Prinsep Michele R Rottmann Matthias Chan Kok Ping Chen David Yu-Kai Tan Lik Tong |
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| Institution: | aNatural Sciences and Science Education, National Institute of Education, Nanyang Technological University, 1 Nanyang Walk, Singapore 637616, Singapore;bDepartment of Chemistry, University of Waikato, Private Bag 3105, Hamilton 3205, New Zealand;cSwiss Tropical and Public Health Institute, Parasite Chemotherapy, Socinstrasse 57, CH-4002 Basel, Switzerland and University of Basel, CH-4003 Basel, Switzerland;dChemical Synthesis Laboratory, Institute of Chemical and Engineering Sciences, 11 Biopolis Way, Helios #03-08, Singapore 138667, Singapore;eDepartment of Chemistry, Seoul National University, Gwanak-1 Gwanak-ro, Gwanak-gu, Seoul 151-742, South Korea |
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| 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 3JH–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 IC50 values ranging from 2.1 nM to 24.4 nM. Compound 1 also displayed significant antimalarial activity with IC50 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. |
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| Keywords: | Lyngbya majuscula Oscillatoriaceae Marine cyanobacteria Cytotoxicity Anti-malarial Cyclic depsipeptide |
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