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Pathway Description
Flavone and Flavonol Biosynthesis
Arabidopsis thaliana
Category:
Metabolite Pathway
Sub-Category:
Metabolic
Created: 2017-02-20
Last Updated: 2025-02-08
Flavonols are a class of flavonoids that have a flavone backbone and a C3 hydroxyl group. These compounds can be found in many fruits and vegetables. This pathway, whereby flavones and flavonols are synthesized and modified, occurs in the cytoplasm and only has a single endoplasmic-reticulum-associated enzyme (flavonoid 3'-hydroxylase) which is coloured dark green in the pathway image. Flavonoid 3'-hydroxylase converts apigenin, aromadendrin (dihydrokaempferol), and kaempferol into luteolin, taxifolin (dihydroquercetin), and quercetin, respectively. Flavonol synthase (FLS) uses oxoglutaric acid and oxygen to catalyze the conversion of dihydroflavonols from flavonols. Requiring Fe2+ and ascorbate as cofactors, FLS converts dihydroquercetin (taxifolin) into quercetin and dihydrokaempferol (aromadendrin) into kaempferol, producing succinic acid, carbon dioxide, and water as byproducts. Four modifications to the flavonol, quercetin, include sulfonation, methylation, glycosylation, and rhamnosylation. Gglycosylation and rhamnosylation are carried out in the chloroplast. Quercetin 3-sulfotransferase utilizes 3'-phosphoadenylyl-sulfate (PAPS) to transfer a sulfate group to quercetin which forms quercetin 3-sulfate. This reaction produces adenosine 3',5'-diphosphate as a byproduct. Quercetin 3'-O-methyltransferase uses S-adenosylmethionine to methylate quercetin to produce isorhamnetin and S-adenosylhomocysteine. Flavonol 3-O-glucosyltransferase catalyzes the conversion of quercetin into isoquercitrin. Flavonol-3-O-rhamnosyltransferase catalyzes two successive reactions to convert quercetin first into quercitrin and then second into quercetin 3-O-rhamnoside 7-O-glucoside. Kaempferol also undergoes modifications such as glycosylation and rhamnosylation. Flavonol 3-O-glucosyltransferase catalyzes the conversion of kaempferol into astragalin. Flavonol-3-O-rhamnosyltransferase catalyzes two successive reactions to convert kaempferol first into afzelin (kaempferin) and then second into kaempferol 3-O-rhamnoside-7-O-glucoside.
References
Flavone and Flavonol Biosynthesis References
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Pubmed: 9112784
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Cheng CY, Krishnakumar V, Chan AP, Thibaud-Nissen F, Schobel S, Town CD: Araport11: a complete reannotation of the Arabidopsis thaliana reference genome. Plant J. 2017 Feb;89(4):789-804. doi: 10.1111/tpj.13415. Epub 2017 Feb 10.
Pubmed: 27862469
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Zhang H, Wang J, Goodman HM: An Arabidopsis gene encoding a putative 14-3-3-interacting protein, caffeic acid/5-hydroxyferulic acid O-methyltransferase. Biochim Biophys Acta. 1997 Sep 12;1353(3):199-202. doi: 10.1016/s0167-4781(97)00096-1.
Pubmed: 9349713
Kotani H, Nakamura Y, Sato S, Asamizu E, Kaneko T, Miyajima N, Tabata S: Structural analysis of Arabidopsis thaliana chromosome 5. VI. Sequence features of the regions of 1,367,185 bp covered by 19 physically assigned P1 and TAC clones. DNA Res. 1998 Jun 30;5(3):203-16. doi: 10.1093/dnares/5.3.203.
Pubmed: 9734815
Schoenbohm C, Martens S, Eder C, Forkmann G, Weisshaar B: Identification of the Arabidopsis thaliana flavonoid 3'-hydroxylase gene and functional expression of the encoded P450 enzyme. Biol Chem. 2000 Aug;381(8):749-53. doi: 10.1515/BC.2000.095.
Pubmed: 11030432
Tabata S, Kaneko T, Nakamura Y, Kotani H, Kato T, Asamizu E, Miyajima N, Sasamoto S, Kimura T, Hosouchi T, Kawashima K, Kohara M, Matsumoto M, Matsuno A, Muraki A, Nakayama S, Nakazaki N, Naruo K, Okumura S, Shinpo S, Takeuchi C, Wada T, Watanabe A, Yamada M, Yasuda M, Sato S, de la Bastide M, Huang E, Spiegel L, Gnoj L, O'Shaughnessy A, Preston R, Habermann K, Murray J, Johnson D, Rohlfing T, Nelson J, Stoneking T, Pepin K, Spieth J, Sekhon M, Armstrong J, Becker M, Belter E, Cordum H, Cordes M, Courtney L, Courtney W, Dante M, Du H, Edwards J, Fryman J, Haakensen B, Lamar E, Latreille P, Leonard S, Meyer R, Mulvaney E, Ozersky P, Riley A, Strowmatt C, Wagner-McPherson C, Wollam A, Yoakum M, Bell M, Dedhia N, Parnell L, Shah R, Rodriguez M, See LH, Vil D, Baker J, Kirchoff K, Toth K, King L, Bahret A, Miller B, Marra M, Martienssen R, McCombie WR, Wilson RK, Murphy G, Bancroft I, Volckaert G, Wambutt R, Dusterhoft A, Stiekema W, Pohl T, Entian KD, Terryn N, Hartley N, Bent E, Johnson S, Langham SA, McCullagh B, Robben J, Grymonprez B, Zimmermann W, Ramsperger U, Wedler H, Balke K, Wedler E, Peters S, van Staveren M, Dirkse W, Mooijman P, Lankhorst RK, Weitzenegger T, Bothe G, Rose M, Hauf J, Berneiser S, Hempel S, Feldpausch M, Lamberth S, Villarroel R, Gielen J, Ardiles W, Bents O, Lemcke K, Kolesov G, Mayer K, Rudd S, Schoof H, Schueller C, Zaccaria P, Mewes HW, Bevan M, Fransz P: Sequence and analysis of chromosome 5 of the plant Arabidopsis thaliana. Nature. 2000 Dec 14;408(6814):823-6. doi: 10.1038/35048507.
Pubmed: 11130714
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Yamada K, Lim J, Dale JM, Chen H, Shinn P, Palm CJ, Southwick AM, Wu HC, Kim C, Nguyen M, Pham P, Cheuk R, Karlin-Newmann G, Liu SX, Lam B, Sakano H, Wu T, Yu G, Miranda M, Quach HL, Tripp M, Chang CH, Lee JM, Toriumi M, Chan MM, Tang CC, Onodera CS, Deng JM, Akiyama K, Ansari Y, Arakawa T, Banh J, Banno F, Bowser L, Brooks S, Carninci P, Chao Q, Choy N, Enju A, Goldsmith AD, Gurjal M, Hansen NF, Hayashizaki Y, Johnson-Hopson C, Hsuan VW, Iida K, Karnes M, Khan S, Koesema E, Ishida J, Jiang PX, Jones T, Kawai J, Kamiya A, Meyers C, Nakajima M, Narusaka M, Seki M, Sakurai T, Satou M, Tamse R, Vaysberg M, Wallender EK, Wong C, Yamamura Y, Yuan S, Shinozaki K, Davis RW, Theologis A, Ecker JR: Empirical analysis of transcriptional activity in the Arabidopsis genome. Science. 2003 Oct 31;302(5646):842-6. doi: 10.1126/science.1088305.
Pubmed: 14593172
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