AI Article Synopsis
- A new cyclic peptide called jamaicensamide A, containing six amino acids and a unique thiazole-homologated amino acid, was extracted from the Bahamian sponge Plakina jamaicensis alongside known compounds.
- The structure of jamaicensamide A was determined using various analytical techniques, including mass spectrometry and nuclear magnetic resonance.
- The similarity between jamaicensamide A and other peptides from Western Pacific sponges suggests a shared biosynthetic source, likely due to a symbiotic bacterium called Entotheonella sp., indicating that different sponge species may host similar or the same symbionts.
Article Abstract
A new cyclic peptide, jamaicensamide A, composed of six amino acids, including a thiazole-homologated amino acid, was isolated from the Bahamian sponge Plakina jamaicensis, along with known compounds bitungolide A and franklinolide A. The structure of the title peptide was solved by integrated analysis of MS, 1D and 2D NMR data, oxidation-hydrolyses to α-amino acids, and their stereodetermination by Marfey's method. The close structural resemblance of Western Atlantic-derived jamaicensamide A to known Western Pacific-derived peptides of lithistid sponges in the genus Theonella and Discodermia suggests a common origin: the symbiotic bacterium Entotheonella sp., a so-called "talented producer" responsible for biosynthesis of most Theonella-associated peptides. Similar natural products from sponges of disparate genera evince the likelihood that these invertebrates harbor the same or a very similar symbiont.
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| http://dx.doi.org/10.1021/acs.jnatprod.6b00336 | DOI Listing |
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