Category:FL

Revision as of 23:18, 21 September 2009

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 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: Anthocyanin アントシアニン 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

Links to familiar names 耳にする名前

Biosynthesis 生合成

Flavonoid is synthesized through the phenylpropanoid-acetate pathway in all higher plants. It is responsible for many biological activities including pigments, anti-oxidative or anti-allergic agents, and signaling elements in nodule formation. Some of them are quite familiar in our daily life.

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

Biosynthesis

• Flavonoids are seen only in land plants (not algae).

4-coumaroyl CoA + malonyl CoA
CHS
chalcone		FLAVONES
CHI	／FS
naringenin	kaempferol			quercetin		myricetin		FLAVONOLS
F3H	／ FLS			／ FLS		／ FLS
dihydro-kaempferol	F3'H		dihydro-quercetin	F3'5'H		dihydro-myricetin		DIHYDRO FLAVONOLS
DFR	＼LCR	LCR／	DFR		LCR／	DFR
leuco-pelargonidin	PROANTHO- CYANIDINS		leuco-cyanidin	PROANTHO- CYANIDINS		leuco-delphinidin		LEUCOANTHO-CYANIDINS
ANS			ANS			ANS
pelargonidin			cyanidin			delphinidin		ANTHO-CYANIDINS
UR3GT			UR3GT			UR3GT
pelargonidin 3-glucoside			cyanidin 3-glucoside			delphinidin 3-glucoside		ANTHO-CYANINS

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.

Some Flavonoid Ranking ちょっとしたランキング

Heavy 重い 

Heavenly blue anthocyanin ... Well-known skyblue pigment of morning glory (空色で有名な朝顔の色素)

Light 軽い 

1,3-Diphenylpropan-1-one ... as light as the amino acid Tryptophan (アミノ酸トリプトファンと同じぐらいの軽さ)

Long word (単語が)長い 

isopropenyldihydrofuranoflavanone, glucopyranosyldihydrokaempferol

Long name (名前が)長い 

7- [ [ o-6-deoxy-alpha-l-mannopyranosyl- (1->3) -o-6-deoxy-alpha-l-mannopyranosyl- (1->3) -6-deoxy-4-o- [ (2e) -3- (4-hydroxyphenyl) -1-oxo-2-propenyl ] -alpha-l-mannopyranosyl ] oxy ] -3- [ [ o-6-deoxy-alpha-l-mannopyranosyl- (1->3) -o- [ beta-d-glucopyranosyl- (1->6) ] -2-o- [ (2e) -3- (4-hydroxyphenyl) -1-oxo-2-propenyl ] -beta-d-glucopyranosyl ] oxy ] -5-hydroxy-2- (4-hydroxyphenyl) -4h-1-benzopyran-4-one

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.