Lipoxygenase inhibition by anadanthoflavone, a new flavonoid from the aerial parts of Anadenanthera colubrina.
Chemical investigation of the aerial parts of Anadenanthera colubrina led to the isolation of a new flavonoid named anadanthoflavone ( 1), along with 11 known compounds: alnusenol, lupenone, lupeol, betulinic acid, alpha-amyrin, beta-amyrin, beta-sitosterol, stigmasterol, apigenin, 4-hydroxybenzoic acid and cinnamic acid. The isolated compounds were evaluated for their inhibitory activity on human platelet 12-lipoxygenase (12-hLO), human reticulocyte 15-lipoxygenase (15-hLO) and soybean lipoxygenase-1 (15-sLO). Compound 1 was found to be active against 12-hLO and 15-hLO with IC50 values of 13 +/- 3 microM and 17 +/- 3 microM, respectively. Apigenin selectively inhibited the activity of 15-hLO (IC50 : 4.0 +/- 1 microM), while lupenone, lupeol and alpha-amyrin were found active against 15-sLO (IC50 : 22 +/- 3 microM, 35 +/- 9 microM and 15 +/- 3 microM, respectively).
Gutierrez-Lugo
Maria-Teresa
MT
Department of Pharmacology and Toxicology, Division of Medicinal and Natural Products Chemistry, College of Pharmacy, University of Arizona, Tucson, U.S.A.
Deschamps
Joshua D
JD
Holman
Theodore R
TR
Suarez
Enrique
E
Timmermann
Barbara N
BN
D007887:Fabaceae; D005419:Flavonoids / Q000008:administration & dosage / Q000494:pharmacology*; D006801:Humans; D020128:Inhibitory Concentration 50; D008084:Lipoxygenase / Q000096:biosynthesis / Q000187:drug effects; D016859:Lipoxygenase Inhibitors / Q000008:administration & dosage / Q000494:pharmacology*; D008517:Phytotherapy; D035261:Plant Components, Aerial; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology*
D005419:Flavonoids; D016859:Lipoxygenase Inhibitors; D010936:Plant Extracts; C488286:anadanthoflavone; D008084:Lipoxygenase