60508-82-9Relevant academic research and scientific papers
Isolation and structure–activity relationship studies of jacaranones: Anti-inflammatory quinoids from the Cuban endemic plant Jacaranda arborea (Bignoniaceae)
Hirukawa, Minako,Zhang, Menghua,Echenique-Diaz, Lazaro M.,Mizota, Koji,Ohdachi, Satoshi D.,Begué-Quiala, Gerardo,Delgado-Laba?ino, Jorge L.,Gámez-Díez, Jorgelino,Alvarez-Lemus, José,Machado, Leandro Galano,Nú?ez, Miguel Suárez,Shibata, Takahiro,Kigoshi, Hideo,Kita, Masaki
supporting information, (2020/06/03)
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.
