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J Nat Prod. 2019 May 24;82(5):1354-1360. doi: 10.1021/acs.jnatprod.9b00173. Epub 2019 Apr 24.

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

Author information

1
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.
2
Marine Biodiscovery, School of Chemistry and Ryan Institute , National University of Ireland Galway (NUI Galway) , University Road , H91 TK33 Galway , Ireland.
3
Zoology, School of Natural Sciences and Ryan Institute , National University of Ireland Galway (NUI Galway) , University Road , H91 TK33 Galway , Ireland.
4
Équipe C-TAC, UMR CNRS 8038 CiTCoM , Université Paris Descartes , 4 Avenue de l'Observatoire , 75006 Paris , France.
5
Unité Molécules de Communication et Adaptation des Micro-organismes (UMR 7245) , Sorbonne Universités , Muséum National d'Histoire Naturelle, CNRS, Paris , France.
6
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.

Abstract

In the search for bioactive marine natural products from zoantharians of the Tropical Eastern Pacific, four new tyrosine dipeptides, named valdiviamides A-D (1-4), 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 1-4 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.

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