Kahalalides V-Y isolated from a Hawaiian collection of the sacoglossan mollusk Elysia rufescens.

Journal of Natural Products
Karumanchi V RaoMark T. Hamann

Abstract

Four new kahalalides, V (1), W (2), X (3), and Y (4), as well as six previously characterized kahalalides have been isolated from a two-year collection of the sacoglossan mollusk Elysia rufescens. Curiously, kahalalide B, previously isolated in high yield from E. rufescens, was found to be essentially absent from these collections despite identical collection sites and times with previous collections. In addition, kahalalide K, which to date has only been reported from Bryopsis sp., was found in this collection of E. rufescens, suggesting that the production of these metabolites could potentially be from a microbial association with the mollusk and algae, and this relationship is continuously evolving in response to changes in the environment and predation. The structures of new peptides have been established on the basis of extensive 1D and 2D NMR spectroscopic data analysis. Kahalalide V (1) was ascertained to be an acyclic derivative of kahalalide D (5), while kahalalide W (2) was determined to have a 4-hydroxy-L-proline residue instead of the proline in 5. The arginine residue of kahalalide X (3), an acyclic derivative of kahalalide C, was determined to have an L configuration. Kahalalide Y (4) was found to have an L-prolin...Continue Reading

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Sep 20, 1996·The Journal of Organic Chemistry·Mark T. HamannD. Chuck Dunbar
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Citations

Apr 13, 2011·Chemical Reviews·Jiangtao Gao, Mark T Hamann
Aug 20, 2015·Marine Drugs·Natalie Netz, Till Opatz
Jan 27, 2015·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Oct 20, 2010·Natural Product Reports·Roberto G S BerlinckCarolina M Mizuno
Mar 15, 2015·Journal of Natural Products·Arihiro IwasakiKiyotake Suenaga

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