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Open AccessFeature PaperArticle

Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria

Department of Medicinal Chemistry and Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, FL 32610, USA
Research Center for Oceanography, Indonesian Institute of Sciences, Jl. Pasir Putih I, Ancol Timur, Jakarta 14430, Indonesia
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, China
QianYan Pharmatech Limited, Shenzhen 518172, China
Smithsonian Marine Station, 701 Seaway Drive, Fort Pierce, FL 34949, USA
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(2), 83;
Received: 29 December 2018 / Revised: 16 January 2019 / Accepted: 18 January 2019 / Published: 1 February 2019
(This article belongs to the Special Issue Compounds from Cyanobacteria II)
Lagunamide D, a new cytotoxic macrocyclic depsipeptide, was discovered from a collection of marine cyanobacteria from Loggerhead Key in the Dry Tortugas, Florida. An intramolecular ester exchange was observed, where the 26-membered macrocycle could contract to a 24-membered compound via acyl migration at the 1,3-diol unit, and the transformation product was named lagunamide D’. The planar structures of both compounds were elucidated using a combination of nuclear magnetic resonance (NMR) spectroscopy and high-resolution mass spectroscopy (HRMS). The absolute configurations were determined on the basis of enantioselective analysis, modified Mosher’s analysis, Kishi NMR database, and direct comparison with lagunamide A, a structure closely resembling lagunamide D. Lagunamides A and D displayed low-nanomolar antiproliferative activity against A549 human lung adenocarcinoma cells, while the structural transformation from the 26-membered lagunamide D macrocycle to the 24-membered ring structure for lagunamide D’ led to a 9.6-fold decrease in activity. Lagunamide D also displayed potent activity in triggering apoptosis in a dose- and time-dependent manner. Further investigation on the mechanism of action of the lagunamide scaffold is needed to fully explore its therapeutic potential as an anticancer agent. View Full-Text
Keywords: marine cyanobacteria; cyclic depsipeptides; acyl migration; anticancer; apoptosis marine cyanobacteria; cyclic depsipeptides; acyl migration; anticancer; apoptosis
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MDPI and ACS Style

Luo, D.; Putra, M.Y.; Ye, T.; Paul, V.J.; Luesch, H. Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria. Mar. Drugs 2019, 17, 83.

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