title: Structure and antimicrobial activity of phloroglucinol derivatives from Achyrocline satureioides.
abstract: 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.
authors.affiliation: Instituto Universitario de Bio-Orgánica Antonio González (CIBICAN), Departamento de Química Orgánica, Universidad de La Laguna , Avenida Astrofísico Francisco Sánchez No. 2, 38206, La Laguna, Tenerife, Spain.
authors.forename: Carina
authors.initials: C
authors.lastname: Casero
authors.forename: Félix
authors.initials: F
authors.lastname: Machín
authors.forename: Sebastián
authors.initials: S
authors.lastname: Méndez-Álvarez
authors.forename: Mirta
authors.initials: M
authors.lastname: Demo
authors.forename: Ángel G
authors.initials: ÁG
authors.lastname: Ravelo
authors.forename: Nury
authors.initials: N
authors.lastname: Pérez-Hernández
authors.forename: Pedro
authors.initials: P
authors.lastname: Joseph-Nathan
authors.forename: Ana
authors.initials: A
authors.lastname: Estévez-Braun
mesh_terms: D036921:Achyrocline / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D001118:Argentina; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010696:Phloroglucinol / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D011753:Pyrones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D005419:Flavonoids; D005663:Furans; D011753:Pyrones; C452205:achyrofuran; C121845:gnaphalin; D010696:Phloroglucinol