Structure and antimicrobial activity of phloroglucinol derivatives from achyrocline satureioides

Carina Casero, Félix MacHín, Sebastián Méndez-Álvarez, Mirta Demo, Ángel G. Ravelo, Nury Pérez-Hernández, Pedro Joseph-Nathan, Ana Estévez-Braun

Research output: Contribution to journalArticleResearchpeer-review

21 Citations (Scopus)

Abstract

© 2014 The American Chemical Society and American Society of Pharmacognosy. The new prenylated phloroglucinol α-pyrones 1-3 and the new dibenzofuran 4, together with the known 23-methyl-6-O-demethylauricepyrone (5), achyrofuran (6), and 5,7-dihydroxy-3,8-dimethoxyflavone (gnaphaliin A), were isolated from the aerial parts of Achyrocline satureioides. Their structures were determined by 1D and 2D NMR spectroscopic studies, while the absolute configuration of the sole stereogenic center of 1 was established by vibrational circular dichroism measurements in comparison to density functional theory calculated data. The same (S) absolute configuration of the α-methylbutyryl chain attached to the phloroglucinol nucleus was assumed for compounds 2-6 based on biogenetic considerations. Derivatives 7-16 were prepared from 1 and 5, and the antimicrobial activities of the isolated metabolites and some of the semisynthetic derivatives against a selected panel of Gram-positive and Gram-negative bacteria, as well as a set of yeast molds, were determined.
Original languageAmerican English
Pages (from-to)93-102
Number of pages82
JournalJournal of Natural Products
DOIs
StatePublished - 23 Jan 2015

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Achyrocline
Phloroglucinol
Pyrones
Derivatives
Molds
Metabolites
Circular Dichroism
Gram-Negative Bacteria
Yeast
Density functional theory
Bacteria
Fungi
Yeasts
Nuclear magnetic resonance
Antennas

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Casero, Carina ; MacHín, Félix ; Méndez-Álvarez, Sebastián ; Demo, Mirta ; Ravelo, Ángel G. ; Pérez-Hernández, Nury ; Joseph-Nathan, Pedro ; Estévez-Braun, Ana. / Structure and antimicrobial activity of phloroglucinol derivatives from achyrocline satureioides. In: Journal of Natural Products. 2015 ; pp. 93-102.
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Casero, C, MacHín, F, Méndez-Álvarez, S, Demo, M, Ravelo, ÁG, Pérez-Hernández, N, Joseph-Nathan, P & Estévez-Braun, A 2015, 'Structure and antimicrobial activity of phloroglucinol derivatives from achyrocline satureioides', Journal of Natural Products, pp. 93-102. https://doi.org/10.1021/np500735f

Structure and antimicrobial activity of phloroglucinol derivatives from achyrocline satureioides. / Casero, Carina; MacHín, Félix; Méndez-Álvarez, Sebastián; Demo, Mirta; Ravelo, Ángel G.; Pérez-Hernández, Nury; Joseph-Nathan, Pedro; Estévez-Braun, Ana.

In: Journal of Natural Products, 23.01.2015, p. 93-102.

Research output: Contribution to journalArticleResearchpeer-review

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AU - MacHín, Félix

AU - Méndez-Álvarez, Sebastián

AU - Demo, Mirta

AU - Ravelo, Ángel G.

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AU - Joseph-Nathan, Pedro

AU - Estévez-Braun, Ana

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