Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 61, Issue 18, Pages 4336-4343Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf400531h
Keywords
Calceolaria talcana; verbascoside; iridoid monoterpenes; triterpenes; diterpenes; phenylethanoids; naphthoquinones; tyrosinase inhibitory activity; protease inhibition; insect growth inhibitory activity; defense mechanism; plant-insect interaction
Funding
- Comision Nacional de Investigacion Cientifica y Tecnologica de Chile (CONICYT), through FONDECYT Program [1101003, 1130242]
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As a defense mechanism of the aerial parts of Calceolaria talcana (Calceolariaceae; formerly Scrophulariaceae) against herbivore offenses and insect pest attack, diterpenoids, triterpenoids, phenylethanoids, flavonoids, and iridoids are rapidly accumulated along the aerial parts, resulting in a unique natural biopesticide complex from this plant. In addition to verbascoside a series of known compounds were screened for their inhibitory activity against mushroom tyrosinase and protease enzymes. Ethyl acetate and n-hexane extracts, together with cyclopropy1-7,15-ent-pimaradiene (1), abietatriene (2), ursolic acid (3), alpha-lupeol (4), beta-sitosterol (5), 2-hydroxy-3-(1,1-dimethylallyl)-1,4-naphthoquinone (6), alpha-dunnione (7), verbascoside (8), martynoside (9), and some known model compounds proved to be inhibitors of oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) catalyzed by tyrosinase (EC 1.14.18.1) with an I-C50 between 10.0 and 200 ppm or mu M, respectively, suggesting that phenolic moieties in the molecules assayed are important for the activity.
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