Category:FL/Biosynthesis

Biosynthesis of Flavonoid

Flavonoid is synthesized through both the phenylpropanoid-acetate pathway and the acetate-malonate pathway in all higher plants (but not algae). Most plants contain the 6 major subgroups: chalcones, flavanones, flavones, flavonols, flavans, and anthocyani(di)ns. Aurones or isoflavonoids are not ubiquitous.

4-coumaroyl CoA + malonyl CoA

CHS

FLAVONES

CHI

(isomerase)

FS (oxygenase)

IFS

naringenin

FLAVANONE

kaempferol

FLAVONOLS

quercetin

myricetin

ISO-FLAVONES

F3H

(hydroxylase)

FLS (oxygenase)

FLS

DIHYDRO FLAVONOLS

dihydro-kaempferol

F3'H

+OH in B-ring

dihydro-quercetin

F3'5'H

+OH in B-ring

dihydro-myricetin

DFR

(reductase)

DFR

flavan diol
LEUCOANTHO-CYANIDINS

leuco-pelargonidin

(reductase)

LAR

leuco-cyanidin

LAR

leuco-delphinidin

LAR

LDOX

(oxygenase)

PROANTHO- CYANIDINS *

LDOX

PROANTHO- CYANIDINS *

LDOX

*...polymers of flavanols

ANTHO-CYANIDINS

pelargonidin

ANR

cyanidin

ANR

delphinidin

ANR

UF3GT

(+sugar)

epi-afzelechin

UF3GT

epi-catechin

UF3GT

epigallo-catechin

FLAVAN 3-OLS

ANTHO-CYANINS

pelargonidin 3-glucoside

cyanidin 3-glucoside

delphinidin 3-glucoside

UF5GT, AOMT etc.

Information for the Above Abbreviated Gene Names
Six Structural Genes
Abbrev.	Name	Origin	Information
CHS	chalcone synthase	Bacterial polyketide synthases, particularly those in fatty acid synthesis (Verwoert et al. 1992)	Early response against light ^[1] ^[2]
CHI	chalcone-flavanone isomerase	Unclear and unique to plants.^[3] Eubacterium ramulus has the CHI activity. ^[4]	Early response against light.
F3H	flavanone 3-hydroxylase	2-oxoglutarate-dependent dioxygenase family ^[5]	Early response in Arabidopsis but late in Antirrhinum ^[6]
FLS	flavonol synthase	2-oxoglutarate-dependent dioxygenase family ^[7]	Early response against light. In Arabidopsis, all structural genes are single-copy except for this one, to which six genes exist and two of them are not expressed.
DFR	dihydroflavonol 4-reductase	NADPH-dependent reductase associated with steroid metabolism ^[8]	Later response
ANS/LDOX	anthocyanidin synthase or leucoanthocyanidin dioxygenase	2-oxoglutarate-dependent dioxygenase family	Later response
Auxiliary Genes
F3'H	flavonoid 3'-hydroxylase	cytochrome P450 hydroxylase family ^[9]
F3'5'H	flavonoid 3',5'-hydroxylase	cytochrome P450 hydroxylase family ^[10]	Not reported in mosses or liverworts. The transformation of the F3'5'H and the cytochrome b5 gene of petunia into carnation changed its flower color deep purple.^[11]^[12]
FSI	flavone synthase	Dioxygenase in parsley (FSI) and P450 monooxygenase in snapdragon (FSII).
LAR (or LCR)	leucoanthocyanidin reductase
UF3GT	UDP flavonoid glucosyltransferase
GST	glutathione-S-transferase		Transport of flavonoids from cytoplasm to vacuole or cell walls requires both GST and the glutathione pump in ATP-binding cassette family.^[13]^[14]
AOMT	anthocyanin O-methyl transferase
↑ Kubasek WL, Shirley BW, McKillop A, Goodman HM, Briggs W, Ausubel FM: Regulation of flavonoid biosynthetic genes in germinating Arabidopsis seedlings. Plant Cell 1992 4:1229-1236 ↑ Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445 ↑ Jez JM, Bowman ME, Dixon RA, Noel JP: Structure and mechanism of chalcone isomerase: an evolutionarily unique enzyme in plants. Nat Struct Biol 2000 7: 786?791 ↑ Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from Eubacterium ramulus. Arch Microbiol 2004 181:428-434. ↑ Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492 ↑ Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers Antirrhinum majus. Plant J 1991 1:37-49 ↑ Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083 ↑ Baker ME, Blasco RE: Expansion of the mammalian 3bhydroxysteroid dehydrogenase/plant dihydroflavonol reductase superfamily to include a bacterial cholesterol dehydrogenase, a bacterial UDP-galactose 4-epimerase, and open reading frames in vaccinia virus and fish lymphocystis disease virus. FEBS Lett 1992 301: 89?93 ↑ Brugliera F, Barri-Rewell G, Holton TA, Mason JG: Isolation and characterization of a flavonoid 3-hydroxylase. cDNA clone corresponding to the Ht1 locus of Petunia hybrida. Plant J 1999 19: 441?451 ↑ Holton TA, Brugliera F, Lester DR, Tanaka Y, Hyland CD, Menting JGT, Lu CY, Farcy E, Stevenson TW, Cornish EC: Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993 366:276?279 ↑ de Vetten N, ter Horst J, van Schaik H-P, de Boer A, Mol J, Koes R: A cytochrome b5 is required for full activity of flavonoid 39,59-hydroxylase, a cytochrome P450 involved in the formation of blue flowers. Proc Natl Acad Sci USA 1999 96: 778?783 ↑ Brugliera F, Tull D, Holton TA, Karan M, Treloar N, Simpson K, Skurczynska J, Mason JG: Introduction of a cytochrome b5 enhances the activity of flavonoid 3'5' hydroxylase (a cytochrome P450) in transgenic carnation. Sixth International Congress of Plant Molecular Biology. University of Laval, Quebec, 2000 pp S6?S8 ↑ Marrs KA, Alfenito MR, Lloyd AM, Walbot V: A glutathione S-transferase involved in vacuolar transfer encoded by the maise gene Bronze-2. Nature 1995 375: 397?400 ↑ Alfenito MR, Souer E, Goodman CD, Buell R, Mol J, Koes R, Walbot V: Functional complementation of anthocyanin sequestration in the vacuole by widely divergent glutathione S-transferases. Plant Cell 1998 10: 1135?1149

Evolutionary Pressure

Rausher and colleagues studied the relationship between pathway architecture and protein evolutionary rates in anthocyanin biosynthetic pathways. Upstream enzymes showed reduced rates of non-synonymous substitution compared with downstream enzymes, which are under relaxed constraints, in both broad (Zea in monocot and Antirrhinum and Ipomoea in eudicot ^[1] ^[2] ) and narrow (within Ipomoea ^[3]) comparisons. Similarly, the downstream enzyme is under less selective pressure in the carotenoid biosynthetic pathway ^[4].

↑ Rausher MD, Miller R, Tiffin P (1999) "Patterns of evolutionary rate variation among genes of the anthocyanin biosynthetic pathway" Mol Biol Evol 16:266-274
↑ Lu Y, Rausher MD (2003) "Evolutionary rate variation in anthocyanin pathway genes" Mol Biol Evol 20:1844-1853
↑ Rausher MD, Lu Y, Meyer K (2008) "Variation in constraint versus positive selection as an explanation for evolutionary rate variation among anthocyanin genes" J Mol Evol 7:137-144
↑ Livingstone K, Anderson S (2009) "Patterns of variation in the evolution of carotenoid biosynthetic pathway enzymes of higher plants" J Heredity 100:754-761

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[0] Kubasek WL, Shirley BW, McKillop A, Goodman HM, Briggs W, Ausubel FM: Regulation of flavonoid biosynthetic genes in germinating Arabidopsis seedlings. Plant Cell 1992 4:1229-1236

[1] Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445

[2] Jez JM, Bowman ME, Dixon RA, Noel JP: Structure and mechanism of chalcone isomerase: an evolutionarily unique enzyme in plants. Nat Struct Biol 2000 7: 786?791

[3] Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from Eubacterium ramulus. Arch Microbiol 2004 181:428-434.

[4] Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492

[5] Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers Antirrhinum majus. Plant J 1991 1:37-49

[6] Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083

[7] Baker ME, Blasco RE: Expansion of the mammalian 3bhydroxysteroid dehydrogenase/plant dihydroflavonol reductase superfamily to include a bacterial cholesterol dehydrogenase, a bacterial UDP-galactose 4-epimerase, and open reading frames in vaccinia virus and fish lymphocystis disease virus. FEBS Lett 1992 301: 89?93

[8] Brugliera F, Barri-Rewell G, Holton TA, Mason JG: Isolation and characterization of a flavonoid 3-hydroxylase. cDNA clone corresponding to the Ht1 locus of Petunia hybrida. Plant J 1999 19: 441?451

[9] Holton TA, Brugliera F, Lester DR, Tanaka Y, Hyland CD, Menting JGT, Lu CY, Farcy E, Stevenson TW, Cornish EC: Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993 366:276?279

[10] Vetten N, ter Horst J, van Schaik H-P, de Boer A, Mol J, Koes R: A cytochrome b5 is required for full activity of flavonoid 39,59-hydroxylase, a cytochrome P450 involved in the formation of blue flowers. Proc Natl Acad Sci USA 1999 96: 778?783

[11] Brugliera F, Tull D, Holton TA, Karan M, Treloar N, Simpson K, Skurczynska J, Mason JG: Introduction of a cytochrome b5 enhances the activity of flavonoid 3'5' hydroxylase (a cytochrome P450) in transgenic carnation. Sixth International Congress of Plant Molecular Biology. University of Laval, Quebec, 2000 pp S6?S8

[12] Marrs KA, Alfenito MR, Lloyd AM, Walbot V: A glutathione S-transferase involved in vacuolar transfer encoded by the maise gene Bronze-2. Nature 1995 375: 397?400

[13] Alfenito MR, Souer E, Goodman CD, Buell R, Mol J, Koes R, Walbot V: Functional complementation of anthocyanin sequestration in the vacuole by widely divergent glutathione S-transferases. Plant Cell 1998 10: 1135?1149

[14] Rausher MD, Miller R, Tiffin P (1999) "Patterns of evolutionary rate variation among genes of the anthocyanin biosynthetic pathway" Mol Biol Evol 16:266-274

[15] Lu Y, Rausher MD (2003) "Evolutionary rate variation in anthocyanin pathway genes" Mol Biol Evol 20:1844-1853

[16] Rausher MD, Lu Y, Meyer K (2008) "Variation in constraint versus positive selection as an explanation for evolutionary rate variation among anthocyanin genes" J Mol Evol 7:137-144

[17] Livingstone K, Anderson S (2009) "Patterns of variation in the evolution of carotenoid biosynthetic pathway enzymes of higher plants" J Heredity 100:754-761

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Category:FL/Biosynthesis

Biosynthesis of Flavonoid

Evolutionary Pressure

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