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A New Depigmenting‐Antifungal Methylated Grindelane from Grindelia chiloensis
Author(s) -
A. Mesurado María,
Arias Cassará María L.,
Misico Rosana,
Bardón Alicia,
Ybarra María I.,
Cartagena Elena
Publication year - 2017
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201600426
Subject(s) - chemistry , fusarium oxysporum , antifungal , mycelium , terpenoid , stereochemistry , orange (colour) , pigment , organic chemistry , botany , food science , microbiology and biotechnology , biology
The new methylated grindelane diterpenoid, 7 β ‐hydroxy‐8(17)‐dehydrogrindelic acid ( 1b ), together with the known 7 α ‐hydroxy‐8(17)‐dehydrogrindelic acid ( 2a ), 6‐oxogrindelic acid ( 3a ), 4 β ‐hydroxy‐6‐oxo‐19‐norgrindelic ( 4a ), 19‐hydroxygrindelic acid ( 5a ), 18‐hydroxygrindelic acid ( 6a ), 4 α ‐carboxygrindelic acid ( 7a ), 17‐hydroxygrindelic acid ( 8a ), 6 α ‐hydroxygrindelic acid ( 9a ), 8,17‐bisnor‐8‐oxagrindelic acid ( 10a ), 7 α ,8 α ‐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. CHC l 3 extract 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 IC 50 of 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.