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• Gómez-Reyes, JFélix
• Salazar, A
• Guzmán, HM.
• González, Y
• Fernández, PL.
• Ariza-Castolo, A
• Gutiérrez, M
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• Gómez-Reyes, JFélix
• Salazar, A
• Guzmán, HM.
• González, Y
• Fernández, PL.
• Ariza-Castolo, A
• Gutiérrez, M
• [+] on PubMed
• Gómez-Reyes, JFélix
• Salazar, A
• Guzmán, HM.
• González, Y
• Fernández, PL.
• Ariza-Castolo, A
• Gutiérrez, M

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Mar. Drugs 2012, 10(11), 2608-2617; doi:10.3390/md10112608

Article

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

José Félix Gómez-Reyes ^1,2 , Ana Salazar ¹ , Héctor M. Guzmán ³ , Yisett González ⁴ , Patricia L. Fernández ⁴ , Armando Ariza-Castolo ²  and Marcelino Gutiérrez ^1,*

¹ Center for Drug Discovery and Biodiversity, Institute for Scientific Research and Technology Services (INDICASAT), Clayton, City of Knowledge, P.O. Box 0843-01103, Panama ² Department of Chemistry, Center for Research and Advanced Studies of the National Polytechnic Institute (CINVESTAV-IPN), P.O. Box 14-740, 07000, F.D., Mexico ³ Smithsonian Tropical Research Institute, Balboa, Ancon, P.O. Box 0843-03092, Panama ⁴ Center for Molecular and Cellular Biology of Diseases, Institute for Scientific Research and Technology Services (INDICASAT), Clayton, City of Knowledge, P.O. Box 0843-01103, Panama

* Author to whom correspondence should be addressed.

Received: 20 August 2012; in revised form: 26 September 2012 / Accepted: 22 October 2012 / Published: 21 November 2012

Download PDF Full-Text [288 KB, uploaded 21 November 2012 11:19 CET]

Abstract: 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% (IC₅₀) of 4.7 μM and 20.3 μM, respectively. This is the first report of briarellin diterpenes containing a ketone group at C-12.

Keywords: Briareum asbestinum; seco-briarellins; briarellin diterpenes; seco-asbestinin diterpenes; anti-inflammatory properties

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