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

Halogenated Tyrosine Derivatives from the Tropical Eastern Pacific Zoantharians Antipathozoanthus hickmani and Parazoanthus darwini

  • Paul O. Guillen
    Paul O. Guillen
    ESPOL Escuela Superior Politécnica del Litoral, ESPOL, Centro Nacional de Acuacultura e Investigaciones Marinas, Campus Gustavo Galindo km. 30.5 vía Perimetral, P.O. Box 09-01-5863, Guayaquil, Ecuador
    Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
  • Karla B. Jaramillo
    Karla B. Jaramillo
    ESPOL Escuela Superior Politécnica del Litoral, ESPOL, Centro Nacional de Acuacultura e Investigaciones Marinas, Campus Gustavo Galindo km. 30.5 vía Perimetral, P.O. Box 09-01-5863, Guayaquil, Ecuador
    Zoology, School of Natural Sciences and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
  • Laurence Jennings
    Laurence Jennings
    Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
  • Grégory Genta-Jouve
    Grégory Genta-Jouve
    Équipe C-TAC, UMR CNRS 8038 CiTCoM, Université Paris Descartes, 4 Avenue de l’Observatoire, 75006 Paris, France
    Unité Molécules de Communication et Adaptation des Micro-organismes (UMR 7245), Sorbonne Universités, Muséum National d’Histoire Naturelle, CNRS, Paris, France
  • Mercedes de la Cruz
    Mercedes de la Cruz
    Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016, Armilla, Granada, Spain
  • Bastien Cautain
    Bastien Cautain
    Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016, Armilla, Granada, Spain
  • Fernando Reyes
    Fernando Reyes
    Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avenida del Conocimiento 34, Parque Tecnológico de Ciencias de la Salud, E-18016, Armilla, Granada, Spain
  • Jenny Rodríguez
    Jenny Rodríguez
    ESPOL Escuela Superior Politécnica del Litoral, ESPOL, Centro Nacional de Acuacultura e Investigaciones Marinas, Campus Gustavo Galindo km. 30.5 vía Perimetral, P.O. Box 09-01-5863, Guayaquil, Ecuador
  • , and 
  • Olivier P. Thomas*
    Olivier P. Thomas
    Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland
    *Tel: +353-(0)91493563. E-mail: [email protected]
Cite this: J. Nat. Prod. 2019, 82, 5, 1354–1360
Publication Date (Web):April 24, 2019
https://doi.org/10.1021/acs.jnatprod.9b00173
Copyright © 2019 American Chemical Society and American Society of Pharmacognosy

    Article Views

    899

    Altmetric

    -

    Citations

    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    In the search for bioactive marine natural products from zoantharians of the Tropical Eastern Pacific, four new tyrosine dipeptides, named valdiviamides A–D (14), were isolated from Antipathozoanthus hickmani, and two new tyramine derivatives, 5 and 6, from Parazoanthus darwini. The phenols of all six tyrosine derivatives are substituted by bromine and/or iodine atoms at the ortho positions of the hydroxyl. The planar structures of these aromatic alkaloids were elucidated from 1D and 2D NMR experiments in combination with HRESIMS data, and the absolute configurations of 14 were deduced from comparison between experimental and calculated electronic circular dichroism spectra. As halogenated tyrosine derivatives could represent chemotaxonomic markers of these genera, we decided to undertake the first chemical investigation of another species, Terrazoanthus cf. patagonichus. As expected, no halogenated metabolite was evidenced in the species, but we report herein the identification of two new zoanthoxanthin derivatives, named zoamides E (7) and F (8), from this species. Antimicrobial and cytotoxicity bioassays revealed that valdiviamide B (2) displayed moderate cytotoxicity against the HepG2 cell line with an IC50 value of 7.8 μM.

    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.

    Recommended

    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

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jnatprod.9b00173.

    • Biological description of the species; UV, ECD, NMR, and MS data of compounds 18 together with the IR spectrum of 1; and computational analyses for compounds 3 and 8 (PDF)

    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: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 10 publications.

    1. Jason B. Hedges, Katherine S. Ryan. Biosynthetic Pathways to Nonproteinogenic α-Amino Acids. Chemical Reviews 2020, 120 (6) , 3161-3209. https://doi.org/10.1021/acs.chemrev.9b00408
    2. Jayanti Bhandari Neupane, Ram P. Neupane, Yuheng Luo, Wesley Y. Yoshida, Rui Sun, Philip G. Williams. Characterization of Leptazolines A–D, Polar Oxazolines from the Cyanobacterium Leptolyngbya sp., Reveals a Glitch with the “Willoughby–Hoye” Scripts for Calculating NMR Chemical Shifts. Organic Letters 2019, 21 (20) , 8449-8453. https://doi.org/10.1021/acs.orglett.9b03216
    3. Gordon W. Gribble. Naturally Occurring Organohalogen Compounds—A Comprehensive Review. 2023, 1-546. https://doi.org/10.1007/978-3-031-26629-4_1
    4. Ajay Krishna M. S., Sangeetha Mohan, K. T. Ashitha, Manasa Chandramouli, Alaganandam Kumaran, Srikantamurthy Ningaiah, K. Suresh Babu, Sasidhar B. Somappa. Marine Based Natural Products: Exploring the Recent Developments in the Identification of Antimicrobial Agents. Chemistry & Biodiversity 2022, 19 (10) https://doi.org/10.1002/cbdv.202200513
    5. Mario Mardirossian, Marina Rubini, Mauro F. A. Adamo, Marco Scocchi, Michele Saviano, Alessandro Tossi, Renato Gennaro, Andrea Caporale. Natural and Synthetic Halogenated Amino Acids—Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics. Molecules 2021, 26 (23) , 7401. https://doi.org/10.3390/molecules26237401
    6. Andrzej Jończyk, Jan K. Maurin, Monika Moreń, Anna Kowalkowska. Synthesis of 2‐Aryl‐ N ‐(EWG‐methyl)‐ N ‐methylpyrrolidinium Salts as Precursors of Ylides Entering the [1,2] Stevens Rearrangement. ChemistrySelect 2021, 6 (22) , 5575-5585. https://doi.org/10.1002/slct.202100787
    7. Anthony R. Carroll, Brent R. Copp, Rohan A. Davis, Robert A. Keyzers, Michèle R. Prinsep. Marine natural products. Natural Product Reports 2021, 38 (2) , 362-413. https://doi.org/10.1039/D0NP00089B
    8. Paul O. Guillen, Shauna O’Brien, Kishor K. Keekan, Karla B. Jaramillo, Olivier P. Thomas. Serotonin and dopamine derivatives from the Papua New Guinea zoantharian Zoanthus cf. sansibaricus. Phytochemistry Letters 2020, 40 , 1-4. https://doi.org/10.1016/j.phytol.2020.09.001
    9. Yuanxi Fu, Jodi Schneider. Towards Knowledge Maintenance in Scientific Digital Libraries with the Keystone Framework. 2020, 217-226. https://doi.org/10.1145/3383583.3398514
    10. Paul O. Guillen, Karla B. Jaramillo, Grégory Genta-Jouve, Olivier P. Thomas. Marine natural products from zoantharians: bioactivity, biosynthesis, systematics, and ecological roles. Natural Product Reports 2020, 37 (4) , 515-540. https://doi.org/10.1039/C9NP00043G

    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.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect