Viridamides A and B, lipodepsipeptides with antiprotozoal activity from the marine cyanobacterium Oscillatoria nigro-viridis.

Journal of Natural Products
T Luke SimmonsWilliam H Gerwick

Abstract

Parallel chemical and phylogenetic investigation of a marine cyanobacterium from Panama led to the isolation of two new PKS-NRPS-derived compounds, viridamides A and B. Their structures were determined by NMR and mass spectroscopic methods, and the absolute configurations assigned by Marfey's method and chiral HPLC analysis. In addition to six standard, N-methylated amino and hydroxy acids, these metabolites contained the structurally novel 5-methoxydec-9-ynoic acid moiety and an unusual proline methyl ester terminus. Morphologically, this cyanobacterium was identified as Oscillatoria nigro-viridis, and its 16S rDNA sequence is reported here for the first time. Phylogenetic analysis of these sequence data has identified O. nigro-viridis strain OSC3L to be closely related to two other marine cyanobacterial genera, Trichodesmium and Blennothrix. Viridamide A showed antitrypanosomal activity with an IC50 of 1.1 microM and antileishmanial activity with an IC50 of 1.5 microM.

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Citations

Apr 7, 2011·The Journal of Antibiotics·Rahul Kunwar SinghTribhuban M Mohapatra
Jan 15, 2013·Applied and Environmental Microbiology·Niclas EngeneValerie J Paul
Dec 1, 2010·Marine Drugs·Ira Bhatnagar, Se-Kwon Kim
Oct 30, 2010·Current Opinion in Biotechnology·Joshawna K NunneryWilliam H Gerwick
Oct 20, 2010·Current Opinion in Biotechnology·Katharine R WattsPhillip Crews
Sep 13, 2011·Journal of Applied Toxicology : JAT·M NagarajanM Sundararaman
Jul 16, 2014·Pharmaceutical Biology·Maruthanayagam VeerabadhranSundararaman Muthuraman
Mar 19, 2013·Biotechnology Advances·Saradavey Vinothkumar, P S Parameswaran
Nov 6, 2012·Environmental Toxicology and Pharmacology·Ira Bhatnagar, Se-Kwon Kim
Nov 26, 2016·Marine Drugs·Qiu-Ye ChaiBing-Nan Han
Jan 21, 2015·Marine Drugs·Hee Kyoung KangYoonkyung Park
Sep 20, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sergio Martínez-LuisMarcelino Gutiérrez
May 9, 2009·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Karl Gademann, Joanna Kobylinska
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Sep 24, 2019·Natural Product Reports·Raúl G Saraiva, George Dimopoulos
Dec 22, 2009·Chemical Communications : Chem Comm·Shuo LiangTao Ye
Feb 8, 2020·Journal of Medicinal Chemistry·Tanaji T Talele
Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Manuel Jesús Chan-BacabBenjamín Otto Ortega-Morales
Sep 26, 2014·Chemical Reviews·Hidayat HussainSimon Gibbons
Oct 10, 2021·Applied Microbiology and Biotechnology·Ana F S da CunhaSona Jain

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