Category:FL

Revision as of 12:24, 11 December 2009

Flavonoid (フラボノイド)

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. (BY Masanori Arita)

Table 1. Flavonoid Classification

1st Class

FL1: Anthochlor
(Aurone and Chalcone)
オーロン、カルコン

safflower yellow
紅花（末摘花）の黄色

FL2: Flavanone
フラバノン

white skin of orange
みかんジュースの白沈

FL3: Flavone
フラボン

herbs like parsley
セロリやパセリ等ハーブ

[show]2nd Class
FL1A	Aurone
FL1B	Auronol
FL1C	Chalcone
FL1D	Dihydrochalcone

FL2F: Flavanone

FL3F: Flavone

FL4: Dihydroflavonol
ジヒドロフラボノール

antioxidant in grapes
ブドウの抗酸化成分

FL5: Flavonol
フラボノール

vegetables such as onion
たまねぎ等多くの野菜

FL6: Flavan
Leucoanthocyanidin
フラバン

tea, cocoa
お茶、ココア

FL4D: Dihydroflavonol

FL5F: Flavonol

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

FL7: Anthocyani(di)n
アントシアニ(ジ)ン

purple vegetables/fruits
(赤)紫の野菜、果物

FLI: Isoflavonoid
イソフラボノイド

beans
豆類

FLN: Neoflavonoid
ネオフラボノイド

[show]2nd Class
FL7A	Anthocyanin
FL7D	3-Deoxyanthocyanin

[show]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

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

Biosynthesis 生合成

[show] Explanation (解説)
Flavonoid is synthesized through the phenylpropanoid-acetate pathway in all higher plants (but not algae). Most plants contain the six major subgroups (chalcones, flavones, flavonols, flavandiols, anthycyanins, and proanthocyanidins), but the seventh, aurones, is not ubiquitous.

4-coumaroyl CoA + malonyl CoA

CHS

CHALCONES, AURONES

chalcone

FLAVONES

CHI

FS

IFS

FLAVANONE
naringenin

kaempferol

FLAVONOLS

quercetin

myricetin

ISO-FLAVONES

F3H

FLS

DIHYDRO FLAVONOLS

dihydro-kaempferol

F3'H

dihydro-quercetin

F3'5'H

dihydro-myricetin

DFR

LEUCOANTHO-CYANIDINS
(flavan diols)

leuco-pelargonidin

LAR

leuco-cyanidin

LAR

leuco-delphinidin

LAR

LDOX

PROANTHO- CYANIDINS

LDOX

PROANTHO- CYANIDINS

LDOX

PROANTHO- CYANIDINS

ANTHO-CYANIDINS

pelargonidin

ANR

cyanidin

ANR

delphinidin

ANR

UF3GT

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.

[show] Information for the Gene Abbreviations (遺伝子略称の詳細)
Six Structural Genes (構造遺伝子)
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 (その他の遺伝子)
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

Bioactivity

all flavonoids photoprotectant, anti-oxidant 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. For example, quercetin is a more effective photoprotectant and anti-oxidant than kaempferol. ^[1]^[2]	全フラボノイド抗紫外線、抗酸化作用アントシアニンだけでなく、カルコンのような構造の簡単なフラボノイドでも紫外線をよく吸収します。効紫外線は効酸化作用に由来します。例えばクエルセチンはケンフェロールよりも強い効紫外線、効酸化作用を示します。
Tannins (proanthocyanidins) anti-bacteria, anti-fungi	タンニン (プロアントシアニジニン) 抗菌、抗カビ作用

↑ Ryan KG, Swinny EE, Markham KR, Winefield C: Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves. Phytochem 2002 59:23-32
↑ Li J, Ou-Lee T-M, Raba R, Amundson RG, Last RL: Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation. Plant Cell 1993 5: 171-179

Bioavailability

Isoflavones

Isoflavones are efficiently absorbed from the colon and exhibit the highest bioavailability. (Usually polyphenols absorbed from the colon show very low availability.) Daidzein and genistein are known to form chlorinated products (e.g. 3- and 8-chlorodaidzein), then are conjugated with glucuronides and excreted in bile.

Anthocyanins

Although anthocyanins comprise ca. 50% of total polyphenols, they are poorly available (less than 1% of intake in urinary levels). Anthocyanins are absorbed from the stomach, and their glycosides appear in plasma soon after the intake. In blood, only anthocyanins exist in a non-conjugated form.

Flavan

Flavan 3-ols and phenolic acids are efficiently abosrbed from the small instestine, a few hours after intake.

Rest

Non-absorbed flavonoids are transported to the colon, and subjected to metabolism by microbiota. These flavonoids are therefore absorbed much less compared to flavan 3-ols and phenolic acids. Esterification of phenolic acids (e.g. chlorogenic acid), however, reduces absorption.

During absorption, polyphenols are metabolized to form β-glucuronide and sulfate conjugates (phase II conjugation in the intestinal wall), and catechol units are methylated. C-glycosides such as puerarin remain stable and not conjugated. These metabolized forms show markedly different bioactivities from their aglycones.

Links to familiar names 耳にする名前

isoflavonoid in beans (豆のイソフラボン)
anthocyanin in berries (ベリーのアントシアニン)
catechin in tea (お茶のカテキン)
rutin in buckwheat (ソバのルチン)
hesperidin in orange (ミカンのヘスペリジン)
naringenin chalcone in tomato (トマトのナリンゲニンカルコン)

Database statistics/ranking データベース統計

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.

Flavonoid content in food 食品中の量

still under construction
Category	Flavonol	Flavone	Flavan
Names	quercetin, kampferol, myricetin, isorhamnetin	apigenin, luteolin	catechin, epicatechin
broccoli ブロッコリ	Δ
celery セロリ		ΔΔ
fava そら豆			ΔΔ
hot pepper とうがらし		ΔΔ
onion たまねぎ	ΔΔ (Δ)
parsley パセリ		ΔΔΔ
peppermint ペパーミント		ΔΔ
spinach ほうれん草		Δ
thyme タイム		ΔΔΔ
watercress クレソン		Δ
dill, fennel ディル, フェンネル		ΔΔΔ

Δ 5 to <10 mg/100 g; ΔΔ 10 to <50 mg/100 g; ΔΔΔ 50< mg/100 g

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 ID番号の設計

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

[Ryan_2002-14] Ryan KG, Swinny EE, Markham KR, Winefield C: Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves. Phytochem 2002 59:23-32

[15] Li J, Ou-Lee T-M, Raba R, Amundson RG, Last RL: Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation. Plant Cell 1993 5: 171-179

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

[11]

[12]

[13]

[14]

[1]

[2]

@@ Line 398: / Line 398: @@
 |'''all flavonoids'''
 ''photoprotectant, anti-oxidant'' <br/>
-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. For example, quercetin is a more effective photoprotectant and anti-oxidant than kaempferol. <ref name="Ryan 2002">Ryan KG, Swinny EE, Markham KR, Winefield C: Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves. Phytochem 2002 59:23-32</ref><ref>Li J, Ou-Lee T-M, Raba R, Amundson RG, Last RL: Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation. Plant Cell 1993 5: 171?179</ref>
+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. For example, quercetin is a more effective photoprotectant and anti-oxidant than kaempferol. <ref name="Ryan 2002">Ryan KG, Swinny EE, Markham KR, Winefield C: Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves. Phytochem 2002 59:23-32</ref><ref>Li J, Ou-Lee T-M, Raba R, Amundson RG, Last RL: Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation. Plant Cell 1993 5: 171-179</ref>
 |'''全フラボノイド'''
 ''抗紫外線、抗酸化作用'' <br/>
@@ Line 411: / Line 411: @@
 <references/>
-===Links to familiar names <small>耳にする名前</small>===
+==Bioavailability==
+; Isoflavones
+Isoflavones are efficiently absorbed from the colon and exhibit the highest bioavailability. (Usually polyphenols absorbed from the colon show very low availability.) Daidzein and genistein are known to form chlorinated products (e.g. 3- and 8-chlorodaidzein), then are conjugated with glucuronides and excreted in bile.
+; Anthocyanins
+Although anthocyanins comprise ca. 50% of total polyphenols, they are poorly available (less than 1% of intake in urinary levels). Anthocyanins are absorbed from the stomach, and their glycosides appear in plasma soon after the intake. In blood, only anthocyanins exist in a non-conjugated form.
+; Flavan
+Flavan 3-ols and phenolic acids are efficiently abosrbed from the small instestine, a few hours after intake.
+; Rest
+Non-absorbed flavonoids are transported to the colon, and subjected to metabolism by microbiota. These flavonoids are therefore absorbed much less compared to flavan 3-ols and phenolic acids. Esterification of phenolic acids (e.g. chlorogenic acid), however, reduces absorption.
+During absorption, polyphenols are metabolized to form &beta;-glucuronide and sulfate conjugates (phase II conjugation in the intestinal wall), and catechol units are methylated. C-glycosides such as puerarin remain stable and not conjugated. These metabolized forms show markedly different bioactivities from their aglycones.
+==Links to familiar names <small>耳にする名前</small>==
 <div style="column-count:2; -moz-column-count:2;">
 * [[:Category:FLI|isoflavonoid]] in beans (豆のイソフラボン)

Category:FL

Revision as of 12:24, 11 December 2009

Contents

Class Overview

Biosynthesis 生合成

Bioactivity

Bioavailability

Links to familiar names 耳にする名前

Database statistics/ranking データベース統計

Flavonoid content in food 食品中の量

Design of Flavonoid ID numbers ID番号の設計

For Users of Flavonoid Viewer

Subcategories

F

F cont.

F cont.

Pages in category "FL"

F

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