title: A New Depigmenting-Antifungal Methylated Grindelane from Grindelia chiloensis.
abstract: The new methylated grindelane diterpenoid, 7β-hydroxy-8(17)-dehydrogrindelic acid (1b), together with the known 7α-hydroxy-8(17)-dehydrogrindelic acid (2a), 6-oxogrindelic acid (3a), 4β-hydroxy-6-oxo-19-norgrindelic (4a), 19-hydroxygrindelic acid (5a), 18-hydroxygrindelic acid (6a), 4α-carboxygrindelic acid (7a), 17-hydroxygrindelic acid (8a), 6α-hydroxygrindelic acid (9a), 8,17-bisnor-8-oxagrindelic acid (10a), 7α,8α-epoxygrindelic acid (11a), and strictanonic acid (12a) as methyl esters were obtained from an Argentine collection of Grindelia chiloensis (Cornel.) Cabrera. Their structures and relative configurations were established on the basis of spectroscopic analysis. CHCl3extract from the aerial parts and their pure compounds were evaluated for their antifungal and depigmenting effects. Methyl ester derivative of 10a (10b) exhibited a remarkable mycelial growth inhibition against Botritis cinerea with an IC50of 13.5 μg ml-1. While the new grindelane 1b exerted a clear color reduction of the yellow-orange pigment developed by Fusarium oxysporum against UV-induced damage.
authors.affiliation: Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, 4000, Tucumán, Argentina.
authors.forename: María
authors.initials: M
authors.lastname: de Los A Mesurado
authors.affiliation: Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, 4000, Tucumán, Argentina.
authors.forename: María L
authors.initials: ML
authors.lastname: Arias Cassará
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, C1428EGA, Ciudad de Buenos Aires, Argentina.
authors.forename: Rosana
authors.initials: R
authors.lastname: Misico
authors.affiliation: Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, 4000, Tucumán, Argentina.
authors.forename: Alicia
authors.initials: A
authors.lastname: Bardón
authors.affiliation: Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, 4000, Tucumán, Argentina.
authors.forename: María I
authors.initials: MI
authors.lastname: Ybarra
authors.affiliation: Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho, 471, 4000, Tucumán, Argentina.
authors.forename: Elena
authors.initials: E
authors.lastname: Cartagena
mesh_terms: D000935:Antifungal Agents / Q000302:isolation & purification* / Q000494:pharmacology; D004224:Diterpenes; D005670:Fusarium / Q000187:drug effects; D036623:Grindelia / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D062327:Skin Lightening Preparations / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000935:Antifungal Agents; D004224:Diterpenes; D010936:Plant Extracts; D062327:Skin Lightening Preparations; C503616:ent-7beta,11alpha,14-trihydroxy-18-aldehyde-11beta-20-epoxy-kaur-16-en15-one
keywords: Antifungal and depigmenting effects; Botrytis cinerea; Fusarium oxysporum; Grindelane diterpenoids and derivatives; Grindelia chiloensis