3-Hydroxycoumarins: first direct preparation from coumarins using a Cu2(+)-ascorbic acid-O2 system, and their potent bioactivities.
First direct 3-hydroxylation of a coumarin ring via a purely chemical system, previously only possible using cytochrome P-450, was successfully conducted by a Cu2(+)-ascorbic acid-O2 system; the two 3-hydroxycoumarins obtained were novel compounds, 3-hydroxyscopoletin and 3-hydroxyisoscopoletin. 5-Lipoxygenase and alpha-D-glucosidase inhibitory activities of coumarins greatly increased through 3-hydroxylation. 3-Hydroxyscopoletin and 3-hydroxyumbelliferone had a high inhibitory potency for 5-lipoxygenase and for alpha-D-glucosidase respectively; they serve as lead compounds for new drugs.
Aihara
K
K
Faculty of Pharmaceutical Sciences, University of Tokyo, Japan.
Higuchi
T
T
Hirobe
M
M
D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism; D001205:Ascorbic Acid; D001681:Biological Assay; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D003300:Copper; D003374:Coumarins; D065089:Glycoside Hydrolase Inhibitors; D006900:Hydroxylation; D010100:Oxygen; D012603:Scopoletin / Q000031:analogs & derivatives / Q000302:isolation & purification / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014468:Umbelliferones / Q000302:isolation & purification / Q000494:pharmacology
D003374:Coumarins; D065089:Glycoside Hydrolase Inhibitors; D014468:Umbelliferones; C063682:3-hydroxyscopoletin; C063683:3-hydroxyisoscopoletin; D003300:Copper; D001094:Arachidonate 5-Lipoxygenase; D012603:Scopoletin; D001205:Ascorbic Acid; D010100:Oxygen