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Article

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

1
Department of Medicinal Chemistry and Center for Natural Products, Drug Discovery and Development (CNPD3), University of Florida, Gainesville, FL 32610, USA
2
Research Center for Oceanography, Indonesian Institute of Sciences, Jl. Pasir Putih I, Ancol Timur, Jakarta 14430, Indonesia
3
State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics, Shenzhen Graduate School of Peking University, Shenzhen 518055, China
4
QianYan Pharmatech Limited, Shenzhen 518172, China
5
Smithsonian Marine Station, 701 Seaway Drive, Fort Pierce, FL 34949, USA
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(2), 83; https://doi.org/10.3390/md17020083
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. https://doi.org/10.3390/md17020083

AMA Style

Luo D, Putra MY, Ye T, Paul VJ, Luesch H. Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria. Marine Drugs. 2019; 17(2):83. https://doi.org/10.3390/md17020083

Chicago/Turabian Style

Luo, Danmeng, Masteria Y. Putra, Tao Ye, Valerie J. Paul, and Hendrik Luesch. 2019. "Isolation, Structure Elucidation and Biological Evaluation of Lagunamide D: A New Cytotoxic Macrocyclic Depsipeptide from Marine Cyanobacteria" Marine Drugs 17, no. 2: 83. https://doi.org/10.3390/md17020083

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