title: Phytotoxic phenylpropanoids isolated from Ophryosporus charua (Griseb.) Hieron.
abstract: Bioguided isolation of the EtOH extract from the medicinal native plant, Ophryosporus charua, against Raphanus sativus, yielded three phenylpropanoids, charuol A [(Z)-4-((1S,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate], charuepoxide [(Z)-4-((2S,3R)-3-(acetoxymethyl oxiran-2-yl)phenyl) 2-methylbut-2-enoate] and charuol B [(Z)-4-((1R,2R)-3-acetoxy-1,2-dihydroxypropyl)phenyl) 2-methylbut-2-enoate]. Their structures and absolute configuration were established by extensive spectroscopic analyses. The effective concentrations for 50% inhibition of germination (ECg50) and root (ECr50) and shoot (ECs50) elongations were determined for these compounds against P. miliaceum (monocot) and Raphanus sativus (dicot). Charuol A was the most active in the inhibition of germination of P. miliaceum (ECg50= 0.97 mM), followed by charuol B and charuepoxide, although charuol B was the most effective in regulating the root growth of P. miliaceum seedlings, with an ECr50of 1.0 mM. Charuol A inhibited the germination of R. sativus, while its seedling development was also affected by all three compounds with different effectiveness. Charuol A was also highly effective in the 0.09-0.30 mM range against other test species such as Lactuca sativa, Eruca sativa, Allium ampeloprasum and Secale cereale.
authors.affiliation: Unidad Asociada Area Cs. Agr. Ing. Bio. y S.- CONICET - Universidad Católica de Córdoba, Avenida Armada Argentina 3555, CPA X5016DHK, Córdoba, Argentina.
authors.forename: Margarita M Del M
authors.initials: MMDM
authors.lastname: Bravetti
authors.affiliation: Instituto de Investigaciones en Físico Química de Córdoba (INFIQC), Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA, Córdoba, Argentina.
authors.forename: Raquel V
authors.initials: RV
authors.lastname: Vico
authors.affiliation: Unidad Asociada Area Cs. Agr. Ing. Bio. y S.- CONICET - Universidad Católica de Córdoba, Avenida Armada Argentina 3555, CPA X5016DHK, Córdoba, Argentina.
authors.forename: Maria C
authors.initials: MC
authors.lastname: Carpinella
authors.affiliation: CEPROCOR, Ministerio de Ciencia y Tecnología de la Provincia de Córdoba, Arenales 230, 5000, Córdoba, Argentina.
authors.forename: Carlos C
authors.initials: CC
authors.lastname: Ferrayoli
authors.affiliation: Unidad Asociada Area Cs. Agr. Ing. Bio. y S.- CONICET - Universidad Católica de Córdoba, Avenida Armada Argentina 3555, CPA X5016DHK, Córdoba, Argentina. Electronic address: sarapalacios@ucc.edu.ar.
authors.forename: Sara M
authors.initials: SM
authors.lastname: Palacios
mesh_terms: D019659:Asteraceae / Q000737:chemistry*; D018525:Germination / Q000187:drug effects*; D015394:Molecular Structure; D008897:Panicum / Q000187:drug effects; D010666:Phenylpropionates / Q000737:chemistry*; D035261:Plant Components, Aerial / Q000737:chemistry; D010936:Plant Extracts / Q000737:chemistry*; D031224:Raphanus / Q000187:drug effects*; D036226:Seedlings / Q000187:drug effects
chemical_list: D010666:Phenylpropionates; D010936:Plant Extracts
keywords: Asteraceae; Germination inhibition; Growth inhibition; Lactuca sativa; Ophryosporus charua; Panicum miliaceum; Phenylpropanoids; Raphanus sativus