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Kahalalides V–Y Isolated from a Hawaiian Collection of the Sacoglossan Mollusk Elysia rufescens

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Department of Pharmacognosy and National Center for the Development of Natural Products, and Department of Pharmacology, School of Pharmacy, The University of Mississippi, University, Mississippi 38677
* To whom correspondence should be addressed. Tel: 662-915-5730. Fax: 662-915-6975. E-mail: [email protected].
†Department of Pharmacognosy.
‡Department of Pharmacology.
Cite this: J. Nat. Prod. 2008, 71, 5, 772–778
Publication Date (Web):April 12, 2008
https://doi.org/10.1021/np070508g
Copyright © 2008 The American Chemical Society and American Society of Pharmacognosy

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    Abstract

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    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-proline residue instead of the hydroxyproline in kahalalide K. It is clear from this collection of E. rufescens that the discovery of new kahalalide-related metabolites is still highly feasible.

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