Category:FL

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==Class Overview==
 
==Class Overview==
  
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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 [[:Category:FL3F|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 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 [[:Category:FL3F|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).
 
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).
 
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  Flavonoid is utilized in many industrial processes from pigments to food additives.  Often heard names include anthocyanin, catechin, flavan, and isoflavone.
 
  Flavonoid is utilized in many industrial processes from pigments to food additives.  Often heard names include anthocyanin, catechin, flavan, and isoflavone.
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フラボノイドの語源は,ラテン語の flavus （黄色）に「～のような」という意味の oid をつけたものです。これは代表的なフラボンであるquercetinやkaempferolが広く使われてきた黄色の天然色素であることに由来しています ([[:Category:FL3F|flavone]]参照)。
 
フラボノイドの語源は,ラテン語の flavus （黄色）に「～のような」という意味の oid をつけたものです。これは代表的なフラボンであるquercetinやkaempferolが広く使われてきた黄色の天然色素であることに由来しています ([[:Category:FL3F|flavone]]参照)。
  
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フラボノイドの用途は 色素から食品添加物まで多様です。 よく耳にするものでは, アントシアニン, カテキン, フラバン（茶）, イソフラボンなど, 全てフラボノイドです。
 
フラボノイドの用途は 色素から食品添加物まで多様です。 よく耳にするものでは, アントシアニン, カテキン, フラバン（茶）, イソフラボンなど, 全てフラボノイドです。
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Revision as of 23:42, 21 September 2009

Flavonoid (フラボノイド)

Figure 1: The Backbone of Flavonoid Structure


Flavonoid Top Molecule Index Author Index Journals Structure Search Food New Input

Contents

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
Fl1.png
safflower yellow
紅花（末摘花）の黄色 		FL2: Flavanone
フラバノン
Fl2.png
white skin of orange
みかんジュースの白沈 		FL3: Flavone
フラボン
Fl3.png
herbs like parsley
セロリやパセリ等ハーブ
FL2F: Flavanone FL3F: Flavone
FL4: Dihydroflavonol
ジヒドロフラボノール
Fl4.png
antioxidant in grapes
ブドウの抗酸化成分 		FL5: Flavonol
フラボノール
Fl5.png
vegetables such as onion
たまねぎ等多くの野菜 		FL6: Flavan
フラバン
Fl6.png

teas
お茶など
FL4D: Dihydroflavonol FL5F: Flavonol
FL7: Anthocyani(di)n
アントシアニ(ジ)ン
Fl7.png
purple vegetables/fruits
(赤)紫の野菜、果物 		FLI: Isoflavonoid
イソフラボノイド
Fli.png
beans
豆類 		FLN: Neoflavonoid
ネオフラボノイド
Fln.png


Links to familiar names 耳にする名前

Biosynthesis 生合成

4-coumaroyl CoA
+ malonyl CoA
Arrow00d35.pngCHS
chalcone FLAVONES
Arrow00d35.pngCHI ／FS
naringenin kaempferol quercetin myricetin FLAVONOLS
Arrow00d35.pngF3H ／ FLS ／ FLS ／ FLS
dihydro-kaempferol F3'H
Arrow00r35.png 		dihydro-quercetin F3'5'H
Arrow00r35.png 		dihydro-myricetin DIHYDRO FLAVONOLS
Arrow00d35.pngDFR ＼LCR LCR／ Arrow00d35.pngDFR LCR／ Arrow00d35.pngDFR
leuco-pelargonidin PROANTHO- CYANIDINS leuco-cyanidin PROANTHO- CYANIDINS leuco-delphinidin LEUCOANTHO-CYANIDINS
Arrow00d35.pngANS Arrow00d35.pngANS Arrow00d35.pngANS
pelargonidin cyanidin delphinidin ANTHO-CYANIDINS
Arrow00d35.pngUR3GT Arrow00d35.pngUR3GT Arrow00d35.pngUR3GT
pelargonidin 3-glucoside cyanidin 3-glucoside delphinidin 3-glucoside ANTHO-CYANINS

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].

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[1]。

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

  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).


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

still under construction
Category Flavonol Flavone Flavan Flavanone
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 x y y z z w c c 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

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