TY - JOUR
T1 - Structure and antimicrobial activity of phloroglucinol derivatives from achyrocline satureioides
AU - Casero, Carina
AU - MacHín, Félix
AU - Méndez-Álvarez, Sebastián
AU - Demo, Mirta
AU - Ravelo, Ángel G.
AU - Pérez-Hernández, Nury
AU - Joseph-Nathan, Pedro
AU - Estévez-Braun, Ana
N1 - Publisher Copyright:
© 2014 The American Chemical Society and American Society of Pharmacognosy.
PY - 2015/1/23
Y1 - 2015/1/23
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84921653040&partnerID=8YFLogxK
U2 - 10.1021/np500735f
DO - 10.1021/np500735f
M3 - Artículo
SN - 0163-3864
VL - 78
SP - 93
EP - 102
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 1
ER -