Structures and Activities of Tiahuramides A–C, Cyclic Depsipeptides from a Tahitian Collection of the Marine Cyanobacterium Lyngbya majuscula

Journal of Natural Products
2018.0

Abstract

The structures of three new cyclic depsipeptides, tiahuramides A (1), B (2), and C (3), from a French Polynesian collection of the marine cyanobacterium Lyngbya majuscula are described. The planar structures of these compounds were established by a combination of mass spectrometry and 1D and 2D NMR experiments. Absolute configurations of natural and nonproteinogenic amino acids were determined through a combination of acid hydrolysis, derivitization with Marfey's reagent, and HPLC. The absolute configuration of hydroxy acids was confirmed by Mosher's method. The antibacterial activities of tiahuramides against three marine bacteria were evaluated. Compound 3 was the most active compound of the series, with an MIC of 6.7 μM on one of the three tested bacteria. The three peptides inhibit the first cell division of sea urchin fertilized eggs with IC

Knowledge Graph

Similar Paper

Structures and Activities of Tiahuramides A–C, Cyclic Depsipeptides from a Tahitian Collection of the Marine Cyanobacterium <i>Lyngbya majuscula</i>
Journal of Natural Products 2018.0
Structures and Activities of Tiahuramides A–C, Cyclic Depsipeptides from a Tahitian Collection of the Marine Cyanobacterium <i>Lyngbya majuscula</i>
Journal of Natural Products 2018.0
Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium<i>Lyngbya majuscula</i>
Journal of Natural Products 2010.0
Palmyramide A, a Cyclic Depsipeptide from a Palmyra Atoll Collection of the Marine Cyanobacterium<i>Lyngbya majuscula</i>
Journal of Natural Products 2010.0
The Guineamides, Novel Cyclic Depsipeptides from a Papua New Guinea Collection of the Marine Cyanobacterium <i>Lyngbya </i><i>m</i><i>ajuscula</i>
Journal of Natural Products 2003.0
The Guineamides, Novel Cyclic Depsipeptides from a Papua New Guinea Collection of the Marine Cyanobacterium <i>Lyngbya </i><i>m</i><i>ajuscula</i>
Journal of Natural Products 2003.0
Trungapeptins A−C, Cyclodepsipeptides from the Marine Cyanobacterium <i>Lyngbya majuscula</i>
Journal of Natural Products 2006.0
Trungapeptins A−C, Cyclodepsipeptides from the Marine Cyanobacterium <i>Lyngbya majuscula</i>
Journal of Natural Products 2006.0
Hantupeptin A, a Cytotoxic Cyclic Depsipeptide from a Singapore Collection of <i>Lyngbya majuscula</i>
Journal of Natural Products 2009.0
Hantupeptin A, a Cytotoxic Cyclic Depsipeptide from a Singapore Collection of <i>Lyngbya majuscula</i>
Journal of Natural Products 2009.0