seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum

Two new eunicellin-based diterpenes, seco-briarellinone (1) and briarellin S (2), and a known seco-asbestinin (3) have been isolated from the methanolic extract of the common octocoral Briareum asbestinum collected in Bocas del Toro, Caribbean of Panama. The structures and relative stereochemistry o...

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Autores principales: Gómez-Reyes, José Félix, Salazar, Ana, Guzmán, Héctor M., González, Yisett, Fernández, Patricia L., Ariza-Castolo, Armando, Gutiérrez, Marcelino
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2012
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3509539/
https://www.ncbi.nlm.nih.gov/pubmed/23203281
http://dx.doi.org/10.3390/md10112608
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author Gómez-Reyes, José Félix
Salazar, Ana
Guzmán, Héctor M.
González, Yisett
Fernández, Patricia L.
Ariza-Castolo, Armando
Gutiérrez, Marcelino
author_facet Gómez-Reyes, José Félix
Salazar, Ana
Guzmán, Héctor M.
González, Yisett
Fernández, Patricia L.
Ariza-Castolo, Armando
Gutiérrez, Marcelino
author_sort Gómez-Reyes, José Félix
collection PubMed
description Two new eunicellin-based diterpenes, seco-briarellinone (1) and briarellin S (2), and a known seco-asbestinin (3) have been isolated from the methanolic extract of the common octocoral Briareum asbestinum collected in Bocas del Toro, Caribbean of Panama. The structures and relative stereochemistry of the compounds were defined using extensive spectroscopic analysis including 1D, 2D-nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). compounds 1 and 2 displayed anti-inflammatory properties inhibiting nitric oxide (NO) production induced by lipopolisacharide (LPS) in macrophages with an Inhibitory concentration 50% (IC(50)) of 4.7 μM and 20.3 μM, respectively. This is the first report of briarellin diterpenes containing a ketone group at C-12.
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spelling pubmed-35095392012-12-10 seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum Gómez-Reyes, José Félix Salazar, Ana Guzmán, Héctor M. González, Yisett Fernández, Patricia L. Ariza-Castolo, Armando Gutiérrez, Marcelino Mar Drugs Article Two new eunicellin-based diterpenes, seco-briarellinone (1) and briarellin S (2), and a known seco-asbestinin (3) have been isolated from the methanolic extract of the common octocoral Briareum asbestinum collected in Bocas del Toro, Caribbean of Panama. The structures and relative stereochemistry of the compounds were defined using extensive spectroscopic analysis including 1D, 2D-nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS). compounds 1 and 2 displayed anti-inflammatory properties inhibiting nitric oxide (NO) production induced by lipopolisacharide (LPS) in macrophages with an Inhibitory concentration 50% (IC(50)) of 4.7 μM and 20.3 μM, respectively. This is the first report of briarellin diterpenes containing a ketone group at C-12. MDPI 2012-11-21 /pmc/articles/PMC3509539/ /pubmed/23203281 http://dx.doi.org/10.3390/md10112608 Text en © 2012 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Gómez-Reyes, José Félix
Salazar, Ana
Guzmán, Héctor M.
González, Yisett
Fernández, Patricia L.
Ariza-Castolo, Armando
Gutiérrez, Marcelino
seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title_full seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title_fullStr seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title_full_unstemmed seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title_short seco-Briarellinone and Briarellin S, Two New Eunicellin-Based Diterpenoids from the Panamanian Octocoral Briareum asbestinum
title_sort seco-briarellinone and briarellin s, two new eunicellin-based diterpenoids from the panamanian octocoral briareum asbestinum
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3509539/
https://www.ncbi.nlm.nih.gov/pubmed/23203281
http://dx.doi.org/10.3390/md10112608
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