Increasing 5-lipoxygenase inhibitory activities by oxidative conversion of o-methoxyphenols to catechols using a Cu2(+)-ascorbic acid-O2 system.
Several complicated o-methoxyphenols were oxidized with high selectivity to catechols by a Cu2(+)-ascorbic acid-O2 system. In this way, the RBL-1 5-lipoxygenase inhibitory activities of o-methoxyphenols were greatly increased. [6]-Norgingerol (4), a novel compound derived from [6]-gingerol (3), shows promise as a lead compound for new drugs because of its high inhibitory potency (IC50 = 5.0 x 10(-8) M).
Aihara
K
K
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Higuchi
T
T
Hirobe
M
M
D000840:Anisoles / Q000032:analysis; D001091:Arachidonate Lipoxygenases / Q000037:antagonists & inhibitors*; D001205:Ascorbic Acid; D002396:Catechols / Q000138:chemical synthesis / Q000494:pharmacology*; D055598:Chemical Phenomena; D002621:Chemistry; D003300:Copper; D016859:Lipoxygenase Inhibitors; D010084:Oxidation-Reduction
D000840:Anisoles; D002396:Catechols; D016859:Lipoxygenase Inhibitors; C009760:mequinol; D003300:Copper; D001091:Arachidonate Lipoxygenases; D001205:Ascorbic Acid