1. Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae).
- Author
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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, and Kita, Masaki more...
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STRUCTURE-activity relationships , *ENDEMIC plants , *BIGNONIACEAE , *ESTER derivatives , *TRADITIONAL medicine , *ACARICIDES , *ETHYL esters - Abstract
• Activity screening of Cuban endemic plants used as traditional medicines. • Discovery of an anti-inflammatory quinoid from a Cuban endemic plant. • Structure-activity relationship studies and stability analysis. • Monitoring of inflammatory cytokines in vitro and in vivo. • Relationship of anti-inflammatory activity and electrophilicity as a Michael acceptor. 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. [ABSTRACT FROM AUTHOR] more...
- Published
- 2020
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