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.
| [show] 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
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| 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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CHS
FS (oxygenase)
flavan diol
LAR
