Flavonoid biosynthesis

Flavonoids are a major class of plant secondary metabolites that serves a multitude of functions including pigments and antioxidant activity. Flavonoids are synthesized from phenylpropanoid derivatives by condensation with malonyl-CoA. For example, condensation of p-coumaroyl-CoA (C6-C3) with three malonyl-CoA (C3) molecules results in naringenin chalcone with a diphenylpropane (C6-C3-C6) unit, which is converted to naringenin with the flavone (2-phenylchromen-4-one) backbone by conjugate ring closure. These and further modifications yield a variety of structural forms including chalcones, flavanones, dihyroflavonols, and flavans, anthocyanins, flavones and flavonols, and isoflavonoids.

Metabolism; Biosynthesis of other secondary metabolites

PMID:16945088

Tsai CJ, Harding SA, Tschaplinski TJ, Lindroth RL, Yuan Y.

Genome-wide analysis of the structural genes regulating defense phenylpropanoid metabolism in Populus.

New Phytol 172:47-62 (2006)

PMID:16367960

Ono E, Hatayama M, Isono Y, Sato T, Watanabe R, Yonekura-Sakakibara K, Fukuchi-Mizutani M, Tanaka Y, Kusumi T, Nishino T, Nakayama T.

Localization of a flavonoid biosynthetic polyphenol oxidase in vacuoles.

Plant J 45:133-43 (2006)

PMID:16774647

Morreel K, Goeminne G, Storme V, Sterck L, Ralph J, Coppieters W, Breyne P, Steenackers M, Georges M, Messens E, Boerjan W.

Genetical metabolomics of flavonoid biosynthesis in Populus: a case study.

Plant J 47:224-37 (2006)

PMID:16832053

Ono E, Fukuchi-Mizutani M, Nakamura N, Fukui Y, Yonekura-Sakakibara K, Yamaguchi M, Nakayama T, Tanaka T, Kusumi T, Tanaka Y.

Yellow flowers generated by expression of the aurone biosynthetic pathway.

Proc Natl Acad Sci U S A 103:11075-80 (2006)

Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.

Synthesis of (14C)-labeled 5-deoxyflavonoids and their application in the study of dihydroflavonol/leucoanthocyanidin interconversion by dihydroflavonol 4-reductase.

Plant Science 170(3): 587-595 (2006)

PMID:15231405

Stevens JF, Page JE.

Xanthohumol and related prenylflavonoids from hops and beer: to your good health!

Phytochemistry 65:1317-30 (2004)

Ogata J, Itoh Y, Ishida M, Yoshida H, Ozeki Y.

Cloning and heterologous expression of cDNAs encoding flavonoid glucosyltransferases from Dianthus caryophyllus.

Plant Biotechnology 21(5):367-375 (2004)

PMID:12828368

Springob K, Nakajima J, Yamazaki M, Saito K.

Recent advances in the biosynthesis and accumulation of anthocyanins.

Nat Prod Rep 20:288-303 (2003)

PMID:12644647

Shimada N, Aoki T, Sato S, Nakamura Y, Tabata S, Ayabe S.

A cluster of genes encodes the two types of chalcone isomerase involved in the biosynthesis of general flavonoids and legume-specific 5-deoxy(iso)flavonoids in Lotus japonicus.

Plant Physiol 131:941-51 (2003)

Halbwirth H, Martens S, Wienand U, Forkmann G, Stich K.

Biochemical formation of anthocyanins in silk tissue of Zea mays.

Plant Science 164(4):489-495 (2003)

Martens S, Knott J, Seitz CA, Janvari L, Yu SN, Forkmann G.

Impact of biochemical pre-studies on specific metabolic engineering strategies of flavonoid biosynthesis in plant tissues.

Biochemical Engineering Journal 14(3):227-235 (2003)

PMID:11073455

Nakayama T, Yonekura-Sakakibara K, Sato T, Kikuchi S, Fukui Y, Fukuchi-Mizutani M, Ueda T, Nakao M, Tanaka Y, Kusumi T, Nishino T.

Aureusidin synthase: a polyphenol oxidase homolog responsible for flower coloration.

Science 290:1163-6 (2000)

PMID:16667183

Lewinsohn E, Britsch L, Mazur Y, Gressel J.

Flavanone Glycoside Biosynthesis in Citrus: Chalcone Synthase, UDP-Glucose:Flavanone-7-O-Glucosyl-Transferase and -Rhamnosyl-Transferase Activities in Cell-Free Extracts.

Plant Physiol 91:1323-1328 (1989)