Zoanthamine Alkaloids from the Zoantharian Zoanthus cf. pulchellus and Their Effects in Neuroinflammation

Paul O Guillen; Sandra Gegunde; Karla B Jaramillo; Amparo Alfonso; Kevin Calabro; Eva Alonso; Jenny Rodriguez; Luis M Botana; Olivier P Thomas

doi:10.3390/md16070242

Zoanthamine Alkaloids from the Zoantharian Zoanthus cf. pulchellus and Their Effects in Neuroinflammation

Mar Drugs. 2018 Jul 20;16(7):242. doi: 10.3390/md16070242.

Authors

Paul O Guillen^{1

2}, Sandra Gegunde³, Karla B Jaramillo^{4

5}, Amparo Alfonso⁶, Kevin Calabro⁷, Eva Alonso⁸, Jenny Rodriguez⁹, Luis M Botana¹⁰, Olivier P Thomas¹¹

Affiliations

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. P.GUILLENMENA1@nuigalway.ie.
² Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland. P.GUILLENMENA1@nuigalway.ie.
³ Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain. sandra.gegunde@rai.usc.es.
⁴ 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. K.JARAMILLOAGUILAR1@nuigalway.ie.
⁵ Zoology, School of Natural Sciences and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland. K.JARAMILLOAGUILAR1@nuigalway.ie.
⁶ Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain. amparo.alfonso@usc.es.
⁷ Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland. kevin.calabro@nuigalway.ie.
⁸ Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain. eva.alonso@usc.es.
⁹ 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. jenrodri@espol.edu.ec.
¹⁰ Departamento de Farmacología, Facultad de Veterinaria, Universidade de Santiago de Compostela, 27002 Lugo, Spain. luis.botana@usc.es.
¹¹ Marine Biodiscovery, School of Chemistry and Ryan Institute, National University of Ireland Galway (NUI Galway), University Road, H91 TK33 Galway, Ireland. olivier.thomas@nuigalway.ie.

Abstract

Two new zoanthamine alkaloids, namely 3-acetoxynorzoanthamine (1) and 3-acetoxyzoanthamine (2), have been isolated from the zoantharian Zoanthus cf. pulchellus collected off the coast of the Santa Elena Peninsula, Ecuador, together with three known derivatives: zoanthamine, norzoanthamine, and 3-hydroxynorzoanthamine. The chemical structures of 1 and 2 were determined by interpretation of their 1D and 2D NMR data and comparison with literature data. This is the first report of zoanthamine-type alkaloids from Zoanthus cf. pulchellus collected in the Tropical Eastern Pacific. The neuroinflammatory activity of all the isolated compounds was evaluated in microglia BV-2 cells and high inhibitory effects were observed in reactive oxygen species (ROS) and nitric oxide (NO) generation.

Keywords: Tropical Eastern Pacific; Zoanthus pulchellus; inflammation; zoanthamine; zoantharia.

MeSH terms

Alkaloids / chemistry*
Alkaloids / pharmacology*
Animals
Anthozoa / chemistry*
Azepines / chemistry*
Azepines / pharmacology*
Heterocyclic Compounds, 4 or More Rings / chemistry*
Heterocyclic Compounds, 4 or More Rings / pharmacology*
Inflammation / drug therapy*
Magnetic Resonance Spectroscopy / methods
Microglia / drug effects
Nitric Oxide / metabolism
Quinolines / chemistry*
Quinolines / pharmacology*
Reactive Oxygen Species / metabolism
Stereoisomerism

Substances

Alkaloids
Azepines
Heterocyclic Compounds, 4 or More Rings
Quinolines
Reactive Oxygen Species
zoanthamine
norzoanthamine
Nitric Oxide