Flavone and Flavonol Biosynthesis - https://www.kegg.jp/kegg-bin/highlight_pathway?scale=1.0&map=map00944&keyword=flavonoids Flavones and flavonols (3-hydroxyflavones) are common flavonoids in the plant kingdom. They are synthesized as part of the flavonoid modification pathways in aglycone and glucoside forms. (Flavonoid Biosynthesis) -> [1,2] 1) Apigenin -> [1,2,3,4,5] 1) flavone 7-O-beta-glucosyltransferase -> Cosmosiin -> [1,2] 1) flavone apiosyltransferase -> Apiin -> isoflavone 7- O-glucoside-6’’-O-malonyltransferase -> Malonylapiin OR 2) flavanone 7-O- glucoside 2’’-O-beta-L-rhamnosyltransferase -> Rhoifolin OR 2) Isovitexin -> isovitexin beta-glucosyltransferase -> isovitexin 2’’-O-beta-D- glucoside OR 3) Vitexin -> [1,2] 1) vitexin beta-glucosyltransferase -> Vitexin 2’’-O-beta-D-glucoside OR 2) Vitexin 2’’-O-beta-L-rhamnoside -> vitexin 2’’-O-rhamnoside 7-O-methyltransferase -> Isoswertisin 2’’- rhamnoside OR 4) flavonoid 3’,5’-hydroxylase & flavonoid 3’-monooxygenase -> Luteolin -> [1,2,3] 1) flavone 7-O-beta-glucosyltransferase -> Luteolin 7-O-beta-D-glucoside -> flavanone 7-O-glucoside 2’’-O-beta-L- rhamnosyltransferase -> Scolymoside OR 2) luteolin 7-O- glucuronosyltransferase -> Luteolin 7-O-glucuronide -> luteolin-7-O- glucuronide-7-O-glucuronide 2’’-O-glucuronosyltransferase -> Luetolin 7-O- [beta-D-glucuronosyl-(1->2)-beta-D-glucuronide] -> luteolin-7-O- diglucuronide 4’-O-glucuronosyltransferase -> Luteolin 7-O-[beta-D- glucuronosyl-(1->2)-beta-D-glucuronide]-4’-O-beta-D-glucuronide -> beta- glucuronidase -> Luetolin 7-O-[beta-D-glucuronosyl-(1->2)-beta-D- glucuronide] OR 5) apigenin 4’-O-methyltransferase -> Acacetin 2) Kaempferol -> [1,2,3,4,5] 1) kaempferol 4’-O-methyltransferase -> Kaempferide OR 2) flavonol-3-O-rhamnosyltransferase -> Kaempferin -> flavonol-3-O-L-rhamnoside-7-O-glucosyltransferase -> Kaempferol 3-O- rhamnoside-7-O-glucoside OR 3) flavonol 3-O-glucosyltransferase -> Astragalin [1,2] 1) flavonol-3-O-glucoside/galactoside glucosyltransferase -> Sophoraflavonolside -> flavonol-3-O-glycoside glucosyltransferase -> Kaempferol 3-sophorotrioside -> flavonol-3-O-triglucoside O- coumaroyltransferase -> Kaempferol 3-O-[6-(4-coumaroyl)-beta-D-glucosyl- (1->2)-beta-D-glucosyl-91->2)-beta-D-glucoside] OR 2) flavonol-3-O- glucoside L-rhamnosyltransferase -> Nictoflorin OR 4)kaempferol 3-O-beta- D-galactosyltransferase -> trifolin -> flavonol-3-O-glucoside/galactoside glucosyltransferase -> Kaempferol 3-O-beta-D-glucosylgalactoside OR 5) flavonoid 3’,5’-hydroxylase & flavonoid 3’-monooxygenase -> Quercetin -> [1,2,3,4,5] 1) flavonol 3-O-glucosyltransferase -> 3-O-methylquercetin -> 3-methylquercetin 7-O-methyltransferase -> 3,7-Di-O-methylquercetin -> 3,7-dimethylquercetin 4’-O-methyltransferase -> Ayarin OR 2) flavonol 3-O- glucosyltransferase -> Isoquercitrin -> [1,2,3,4] 1) flavonol-3-O-beta- glucoside O-malonyltransferase -> Quercetin 3-O-(6-O-malonyl-beta-D- glucoside) OR 2) flavonol-3-O-glycoside xylosyltransferase -> Quercetin 3- O-[beta-D-xylosyl-(1->2)-beta-D-glucoside] OR 3) flavonol-3-O-glucoside L- rhamnosyltransferase -> Rutin -> flavonol-3-O-glycoside xylotransferase -> Hansford Boutchyard IV www.phytpharma.com 2/24/21 Quercetin 3-(2G-xylosylrutinoside) OR 4) flavonol-3-O- glucoside/galactoside glucosyltransferase -> Baimaside -> flavonol-3-O- glycoside glucosyltransferase OR 3) flavonol-3-O-rhamnosyltransferase -> Quercitrin -> flavonol-3-O-L-rhamnoside-7-O-glucosyltransferase -> Quercetin 3-O-rhamnoside 7-O-glucoside OR 4) flavonol 3-sulfotransferase - > Quercetin 3-sulfate -> [1,2] 1) quercetin-3-sulfate 3’-sulfotransferase -> quercetin 3,3’-bissulfate -> quercetin-3,3’-bissulfate 7- sulfotransferase -> Quercetin 3,3’,7-trisulfate OR 2) flavonol 4’sulfotransferase -> Quercetin 3,4-bissulfate -> quercetin-3,3’- bissulfate 7-sulfotransferase -> Quercetin 3,4’,7-trisulfate OR 5) flavonoid 3’,5’-hydroxylase -> Myricetin -> flavonoid O-methyltransferase -> Laricitrin -> flavonoid O-methyltransferase -> Syringetin Hansford Boutchyard IV www.phytpharma.com 2/24/21.