Category:FL

Revision as of 13:39, 7 October 2008

Flavonoid (フラボノイド)

Figure 1: The Backbone of Flavonoid Structure

Related Pages : Molecule Index : Author Index

Class Overview

The word "flavonoid" comes from its Latin origin flavus (yellow) with oid, meaning yellow-ish. It is probably due to its function as (yellow) flower pigments. 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 (tea), and isoflavone.

Links to familiar names 耳にする名前

Table 1. Flavonoid Classification

1st Class
FL1: 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-Desoxyanthocyanin	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

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.

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 0 metabolite-species relationships are registered.

Flavonoid RanKING

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 ... close to the amino acid Tryptophan (アミノ酸トリプトファンと同じぐらい)

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)