Category:FL

Flavonoid (フラボノイド)

Figure 1: The Backbone of Flavonoid Structure

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) 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
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 teas お茶など
FL4D: Dihydroflavonol	FL5F: Flavonol	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
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 生合成

4-coumaroyl CoA + malonyl CoA
	CHS
CHALCONES, AURONES	chalcone		FLAVONES
	CHI	／FS
IFS ／	FLAVANONE naringenin		kaempferol	FLAVONOLS		quercetin	myricetin
ISO-FLAVONES	F3H	／ FLS			／ FLS		／ FLS
DIHYDRO FLAVONOLS	dihydro-kaempferol	F3'H		dihydro-quercetin	F3'5'H		dihydro-myricetin
	DFR			DFR			DFR
LEUCOANTHO-CYANIDINS (flavan diols)	leuco-pelargonidin	LAR		leuco-cyanidin	LAR		leuco-delphinidin	LAR
	ANS/LDOX		PROANTHO- CYANIDINS	ANS/LDOX		PROANTHO- CYANIDINS	ANS/LDOX		PROANTHO- CYANIDINS
ANTHO-CYANIDINS	pelargonidin	ANR		cyanidin	ANR		delphinidin	ANR
	UF3GT		epi-afzelechin	UF3GT		epi-catechin	UF3GT		epigallo-catechin
ANTHO-CYANINS	pelargonidin 3-glucoside			cyanidin 3-glucoside			delphinidin 3-glucoside		FLAVAN 3-OLS
	UF5GT, AOMT etc.			UF5GT, AOMT etc.			UF5GT, AOMT etc.

1. ↑ 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
2. ↑ Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445
3. ↑ 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
4. ↑ Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from Eubacterium ramulus. Arch Microbiol 2004 181:428-434.
5. ↑ Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492
6. ↑ Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers Antirrhinum majus. Plant J 1991 1:37-49
7. ↑ Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083
8. ↑ 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
9. ↑ 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
10. ↑ 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
11. ↑ 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
12. ↑ 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
13. ↑ 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
14. ↑ 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

1. ↑ ^{1.0 1.1} 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

Links to familiar names 耳にする名前

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

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

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.