Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)
2020
Hirukawa, Minako | Zhang, Menghua | Echenique–Diaz, Lazaro M. | Mizota, Koji | Ohdachi, Satoshi D. | Begué–Quiala, Gerardo | Delgado–Labañino, Jorge L. | Gámez–Díez, Jorgelino | Alvarez–Lemus, José | Machado, Leandro Galano | Núñez, Miguel Suárez | Shibata, Takahiro | Kigoshi, Hideo | Kita, Masaki
The Cuban endemic plant Jacaranda arborea (Bignoniaceae) has been traditionally used in folk medicine as an acaricide and for acne treatment. Two known quinoids, methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate (jacaranone) (1) and its ethyl ester 2 were isolated from this species as anti-inflammatory substances. Compound 1 prominently inhibited the production of TNF-α in both LPS-treated macrophages and mice, with low toxicity. Structure-activity relationship studies revealed that the high electrophilicity of 1 as a Michael acceptor played an important role in these effects. Unlike in previous studies, such as those on antitumor, anti-oxidant, and anti-malarial activities, ester derivatives of 1 retained their potent anti-inflammatory activity. Our results suggest that jacaranones may target specific biomacromolecule(s) at lower concentrations than hitherto expected to exhibit potent activities.
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