Category:FL

Revision as of 22:48, 24 March 2012

Flavonoid Database

Figure 1: The Backbone of Flavonoid Structure

Flavonoid Top

Class Overview

The word "flavonoid" comes from its Latin origin flavus (yellow) with oid, meaning yellow-ish. It comes from its history as yellow natural dye (quercetin and kaempferol are the most widespread flavone dyes. See flavone).
Chemically speaking, it is a class of plant secondary metabolites that have two benzene rings (each called A-ring and B-ring) connected by a chain of three carbons (Figure 1). The carbon chain, corresponding to the numbers 2,3,4 in Figure 1, is linked to a hydroxyl group in the A-ring to form the C-ring. The class of flavonoids are usually determined by the modification pattern of the C-ring (Table 1).
Flavonoid is utilized in many industrial processes from pigments to food additives. Often heard names include anthocyanin, catechin, flavan, and isoflavone.

Table 1. Flavonoid Classification

1st Class

FL1: Anthochlor
(Aurone and Chalcone)

safflower yellow

FL2: Flavanone

white skin of orange

FL3: Flavone

herbs like parsley, yellow dye

2nd Class
FL1A	Aurone
FL1B	Auronol
FL1C	Chalcone
FL1D	Dihydrochalcone

FL4: Dihydroflavonol

antioxidant in grapes

FL5: Flavonol

vegetables such as onion

FL6: Flavan
(Leucoanthocyanidin)

tea, cocoa

2nd Class
FL6F	Flavan
FL63	Flavan 3-ol
FL64	Flavan 4-ol
FL6D	Flavan 3,4-diol

FL7: Anthocyani(di)n

purple vegetables/fruits

FLI: Isoflavonoid

beans

FLN: Neoflavonoid

2nd Class
FL7A	Anthocyanin
FL7D	3-Deoxyanthocyanin

2nd Class
FLIA	Isoflavone
FLIB	Isoflavanone
FLIC	Isoflavan
FLID	Pterocarpane
FLIE	Coumestan
FLIF	Rotenoid
FLIG	Coumaranochromone
FLIH	3-Arylcoumarin
FLII	2-Arylbenzofuran
FLIJ	alpha-Methoxynbenzoin

2nd Class
FLNA	4-Arylcoumarin
FLNB	4-Arylchroman
FLNC	Dalbergiquinol
FLND	Dalbergione
FLNE	Neoflavene
FLNF	Coumarinic acid

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

Bioactivity

Tea Related

Tea category 茶の種類
Tea consumption 茶の消費量
Tea and health　茶と健康

Others

Photoprotectant, anti-oxidant activity (More Information)

Not only anthocyanins but even simple structures such as chalcone can absorb UV wavelengths strongly. The ability of photoprotection is derived from its anti-oxidative activity.

Hypotensive activity

Quercetin in onions and flavanols in cocoa are said to reduce blood pressure in hypertensive animals ^[1], but their effect or mechanism is not clinically conclusive.

Anti-bacteria, anti-fungal activity

Tannins (proanthocyanidins) show anti-bacterial activity.

↑ Hooper L, Kroon PA, Rimm EB, et al. (2008) "Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials" Am J Clin Nutr 88:38–50 PMID 18614722

Database statistics/ranking

This database collects original references that report identification of flavonoid in various plant species. The database consists of three major namespaces: (flavonoid) compounds, plant species, and references. Currently, 6961 flavonoid structures, 3961 plant species, and 5215 references describing total 19861 metabolite-species relationships are registered.

class	FL1 (chalcones)	FL2 (flavanones)	FL3 (flavones)	FL4 (dihydroflavonols)	FL5 (flavonols)	FL6 (flavans)	FL7 (anthocyanidins)	FLI (isoflavonoids)	FLN (neoflavonoids)	Total
#data	690	705	1479	272	1943	291	574	916	96	6961

Flavonoid content in food

For details, please visit this page.

Food containing high Flavanone

Flavanones are rich in citrus, not in vegetables.

Food	Flavanone (mg/100g)	食品名
grapefruit, raw or juice	14-53	グレープフルーツ　（生、ジュース）
orange and tangerine, raw or juice	13-33	オレンジ、みかん　(生、ジュース）

Food containing high flavone

Many herbs contain flavones. Parsley is rich in apigenin; celery and thyme in luteolin.

Food	Flavone (mg/100g)	食品名
celery hearts, raw	19	セロリの芯（生）
parsley, raw	302	パセリ　（生）

Food containing high flavonol

Flavonols are prevalent in vegetables, usually in small amounts. Onions, kales, hot peppers are good sources.

Food	Flavonol (mg/100g)	食品名
buckwheat	23	そば
cranberry, juice	16	クランベリー　（ジュース）
onion, raw or boiled	5-20	たまねぎ　（生、ゆで等）
kale, raw or canned	18-34	ケール　(生、かんづめ）

Food containing high flavan

Catechins and epicatechins are contained in legumes and teas, but not in other vegetables.

Food	Flavan (mg/100g or 100ml)	食品名
broadbeans, raw	～50	そらまめ　（生）
dark chocolate bar	～50	ダークチョコレート
black grapes	18	黒いブドウ
brewed black tea	> 16	淹れた紅茶
brewed oolong tea	50	淹れたウーロン茶
brewed green tea	> 50	淹れた緑茶

Food containing high anthocyanin

Anthocyanins are contained in berries. Vegetables supply only small amounts.

Food	Anthocyanin (mg/100g)	食品名
blueberries, raw	113	ブルーベリー　（生）
sweet cherries, raw	116	さくらんぼ　（生）
elderberries, raw	749	エルダーベリー　（生）
raspberries, raw	49	ラズベリー　（生）

Vegetables and herbs with scarce flavonoids

The following vegetables and herbs have flavonoid contents less than 5 mg/100 g: beets, kidney beans, snap beans, cabbage, carrot, cauliflower, cucumber, endive, gourd, leek, lettuce, green peas, sweet pepper, potato, radish, tomato, oregano, perrilla, rosemary

Design of Flavonoid ID numbers

12-DIGIT

F

L

x

y

z

w

c

x ... backbone structure (母核構造)

FL1 aurone and chalcone; FL2 flavanone; FL3 flavone; FL4 Dihydroflavonol; FL5 Flavonol; FL6 Flavan; FL7 Anthocyanin; FLI Isoflavonoid; FLN Neoflavonoid

y ... hydroxylation pattern in A and B ring (水酸基パターン)

Click above categories to see details. General description is here.

z ... glycosylation pattern (糖修飾パターン)

Click above categories to see details. General description is here.

w ... halogenation etc. (ハロゲン等)

Currently unused.

c ... serial number (通し番号)

For Users of Flavonoid Viewer

The flavonoid IDs used in this site is the same as those in Flavonoid Viewer in metabolome.jp except for the following FL7 category.

Anthocyanin glycosylated with other than glucose and galactose
Flavonoid Viewer `FL7A..GS`	→	This site `FL7A..GO`

Subcategories

This category has the following 10 subcategories, out of 10 total.

F

[+] FL1‎ (4 C)
[+] FL2‎ (1 C)
[+] FL3‎ (1 C)
[+] FL4‎ (1 C)

F cont.

[+] FL5‎ (1 C)
[+] FL6‎ (4 C)
[+] FL7‎ (2 C)
[+] FLI‎ (10 C)

F cont.

[+] FLN‎ (6 C)
[×] FLT‎ (empty)

Pages in category "FL"

The following 2 pages are in this category, out of 2 total.

F

[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

[18] Hooper L, Kroon PA, Rimm EB, et al. (2008) "Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials" Am J Clin Nutr 88:38–50 PMID 18614722

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 玉葱のクエルセチンやココアのフラバノールは血圧降下作用があるといわれますが、その効果や医学的メカニズムははっきりしていません。
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Category:FL

Revision as of 22:48, 24 March 2012

Contents

Class Overview

Biosynthesis of Flavonoid

Evolutionary Pressure

Bioactivity

Tea Related

Others

Database statistics/ranking

Flavonoid content in food

Design of Flavonoid ID numbers

For Users of Flavonoid Viewer

Subcategories

F

F cont.

F cont.

Pages in category "FL"

F

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Namespaces

Variants

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