ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

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

View Author Information
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
Copyright © 2008 The American Chemical Society and American Society of Pharmacognosy

    Article Views





    Other access options
    Supporting Info (1)»


    Abstract Image

    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.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    Jump To

    This material is available free of charge via the Internet at

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system:

    Cited By

    This article is cited by 23 publications.

    1. Yueying Li, Hao-Bing Yu, Yi Zhang, Tiago Leao, Evgenia Glukhov, Marsha L. Pierce, Chen Zhang, Hyunwoo Kim, Huanru Henry Mao, Fang Fang, Garrison W. Cottrell, Thomas F. Murray, Lena Gerwick, Huashi Guan, William H. Gerwick. Pagoamide A, a Cyclic Depsipeptide Isolated from a Cultured Marine Chlorophyte, Derbesia sp., Using MS/MS-Based Molecular Networking. Journal of Natural Products 2020, 83 (3) , 617-625.
    2. Arihiro Iwasaki, Osamu Ohno, Shinpei Sumimoto, Teruhiko Matsubara, Satoshi Shimada, Toshinori Sato, and Kiyotake Suenaga . Mebamamides A and B, Cyclic Lipopeptides Isolated from the Green Alga Derbesia marina. Journal of Natural Products 2015, 78 (4) , 901-908.
    3. Christine M. Theodore, Nicholas Lorig-Roach, Patrick C. Still, Tyler A. Johnson, Marija Drašković, Joshua A. Schwochert, Cassandra N. Naphen, Mitchell S. Crews, Simone A. Barker, Frederick A. Valeriote, R. Scott Lokey, and Phillip Crews . Biosynthetic Products from a Nearshore-Derived Gram-Negative Bacterium Enable Reassessment of the Kailuin Depsipeptides. Journal of Natural Products 2015, 78 (3) , 441-452.
    4. Mohamed A. Albadry, Khaled M. Elokely, Bin Wang, John J. Bowling, Mohamed F. Abdelwahab, Mohamed H. Hossein, Robert J. Doerksen, and Mark T. Hamann . Computationally Assisted Assignment of Kahalalide Y Configuration Using an NMR-Constrained Conformational Search. Journal of Natural Products 2013, 76 (2) , 178-185.
    5. Jiangtao Gao and Mark T. Hamann . Chemistry and Biology of Kahalalides. Chemical Reviews 2011, 111 (5) , 3208-3235.
    6. Jiangtao Gao, Catherina Caballero-George, Bin Wang, Karumanchi V. Rao, Abbas Gholipour Shilabin and Mark T. Hamann. 5-OHKF and NorKA, Depsipeptides from a Hawaiian Collection of Bryopsis pennata: Binding Properties for NorKA to the Human Neuropeptide Y Y1 Receptor. Journal of Natural Products 2009, 72 (12) , 2172-2176.
    7. Bimal Krishna Banik, Aparna Das. Anticancer activity of natural compounds from marine animals. 2024, 181-236.
    8. Daniel W. Armstrong, Alain Berthod. Occurrence of D-amino acids in natural products. Natural Products and Bioprospecting 2023, 13 (1)
    9. Scott Wyer, Danyelle M. Townsend, Zhiwei Ye, Antonis Kourtidis, Yeun-Mun Choo, André Luís Branco de Barros, Mohamed S. Donia, Mark T. Hamann. Recent advances and limitations in the application of kahalalides for the control of cancer. Biomedicine & Pharmacotherapy 2022, 148 , 112676.
    10. Maria Wanna Figueiredo Sena Macedo, Nicolau Brito da Cunha, Juliana Araújo Carneiro, Rosiane Andrade da Costa, Sergio Amorim de Alencar, Marlon Henrique Cardoso, Octávio Luiz Franco, Simoni Campos Dias. Marine Organisms as a Rich Source of Biologically Active Peptides. Frontiers in Marine Science 2021, 8
    11. Jindong Zan, Zhiyuan Li, Ma. Diarey Tianero, Jeanette Davis, Russell T. Hill, Mohamed S. Donia. A microbial factory for defensive kahalalides in a tripartite marine symbiosis. Science 2019, 364 (6445)
    12. Supriya Tilvi, Prabha Devi, Mahesh S Majik. Quick elucidation of cyclodepsipeptide sequence from sacoglossan Elysia grandifolia using electrospray ionisation-tandem mass spectrometry. European Journal of Mass Spectrometry 2017, 23 (3) , 92-97.
    13. L. Bornancin, I. Bonnard, S. C. Mills, B. Banaigs. Chemical mediation as a structuring element in marine gastropod predator-prey interactions. Natural Product Reports 2017, 34 (6) , 644-676.
    14. Natalie Netz, Till Opatz. Marine Indole Alkaloids. Marine Drugs 2015, 13 (8) , 4814-4914.
    15. John W. Blunt, Brent R. Copp, Robert A. Keyzers, Murray H. G. Munro, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2015, 32 (2) , 116-211.
    16. Jean‐Michel Kornprobst. Mollusks–2. 2014, 1419-1460.
    17. Bernard Banaigs, Isabelle Bonnard, Anne Witczak, Nicolas Inguimbert. Marine Peptide Secondary Metabolites. 2014, 285-318.
    18. Juan Rubiolo, Eva Alonso, Eva Cagide. Marine Compounds as a Starting Point to Drugs. 2014, 1141-1178.
    19. Masahiro Umehara, Takayuki Negishi, Yukie Maehara, Yoichi Nakao, Junji Kimura. Stereochemical analysis and cytotoxicity of kulokekahilide-2 and its analogues. Tetrahedron 2013, 69 (14) , 3045-3053.
    20. Pavel A. Belyakov, Valentine I. Kadentsev, Alexander O. Chizhov, Natal’ya G. Kolotyrkina, Alexander S. Shashkov, Valentine P. Ananikov. Mechanistic insight into organic and catalytic reactions by joint studies using mass spectrometry and NMR spectroscopy. Mendeleev Communications 2010, 20 (3) , 125-131.
    21. John W. Blunt, Brent R. Copp, Murray H. G. Munro, Peter T. Northcote, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2010, 27 (2) , 165.
    22. Roberto G. S. Berlinck, Antonio Carlos B. Burtoloso, Amaro E. Trindade-Silva, Stelamar Romminger, Raquel P. Morais, Karin Bandeira, Carolina M. Mizuno. The chemistry and biology of organic guanidine derivatives. Natural Product Reports 2010, 27 (12) , 1871.
    23. Masahiro Umehara, Yuuki Takada, Yoichi Nakao, Junji Kimura. Intramolecular ester exchange of potent cytotoxic kulokekahilide-2. Tetrahedron Letters 2009, 50 (7) , 840-843.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect