Category:FL

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Flavonoid (フラボノイド)

Figure 1: The Backbone of Flavonoid Structure
Figure 1: The Backbone of Flavonoid Structure
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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. (BY Masanori Arita)

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 (flavone参照)。 化学的な定義でフラボノイドとは, ベンゼン環2個 (それぞれA環B環と呼ばれる) を3つの炭素 (C) で結合した, 植物の代謝産物の総称です (Figure 1)。 Figure 1 において 2,3,4 と番号付けされた炭素鎖は A 環の水酸基と結合して C 環を構成します。フラボノイドのカテゴリーは,たいてい C 環の修飾パターンで決まります (Table 1)。 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。 (BY 有田正規)

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
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
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

Biosynthesis 生合成

4-coumaroyl CoA + malonyl CoA
Image:Arrow00d35.pngCHS
CHALCONES, AURONES chalconaringenin FLAVONES
CHI Image:Arrow00d35.png (isomerase) Image:Arrow00ur35.pngFS (oxygenase)

IFS Image:Arrow00dl35.png
FLAVANONE

naringenin
kaempferol FLAVONOLS quercetin myricetin
ISO-FLAVONES F3H Image:Arrow00d35.png (hydroxylase) Image:Arrow00ur35.png FLS (oxygenase) Image:Arrow00ur35.png FLS Image:Arrow00ur35.png FLS
DIHYDRO FLAVONOLS dihydro-kaempferol F3'H
Image:Arrow00r100.png
+OH in B-ring
dihydro-quercetin F3'5'H
Image:Arrow00r100.png
+OH in B-ring
dihydro-myricetin
DFR Image:Arrow00d35.png (reductase) Image:Arrow00d35.pngDFR Image:Arrow00d35.pngDFR
flavan diol
LEUCOANTHO-CYANIDINS
leuco-pelargonidin
Image:Arrow00dr35.png
(reductase)
LAR
leuco-cyanidin Image:Arrow00dr35.png LAR leuco-delphinidin Image:Arrow00dr35.png LAR
LDOX Image:Arrow00d35.png (oxygenase) PROANTHO- CYANIDINS *    Image:Arrow00d35.png LDOX    PROANTHO- CYANIDINS *    Image:Arrow00d35.png LDOX    *...polymers of flavanols
ANTHO-CYANIDINS pelargonidin Image:Arrow00dr35.pngANR   Image:Arrow00u35.png cyanidin Image:Arrow00dr35.pngANR   Image:Arrow00u35.png delphinidin Image:Arrow00dr35.pngANR   Image:Arrow00u35.png
UF3GT Image:Arrow00d35.png (+sugar) epi-afzelechin Image:Arrow00d35.pngUF3GT epi-catechin Image:Arrow00d35.pngUF3GT epigallo-catechin FLAVAN 3-OLS
ANTHO-CYANINS pelargonidin 3-glucoside cyanidin 3-glucoside delphinidin 3-glucoside
Image:Arrow00d35.png UF5GT, AOMT etc.
Image:Arrow00d35.png UF5GT, AOMT etc.
Image:Arrow00d35.png UF5GT, AOMT etc.

Bioactivity

For tea, visit here.
お茶についてはこちら.
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。

Flavanols

Quercetin in onions and flavanols in cocoa are said to reduce blood pressure in hypertensive animals, but their effect is not clinically conclusive.

フラバノール

玉葱のクエルセチンやココアのフラバノールは血圧降下作用があるといわれますが、その医学的効果ははっきりしていません。

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. 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
  2. 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.

Others

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

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, 6918 flavonoid structures, 3653 plant species, and 4997 references describing total 19851 metabolite-species relationships are registered.

このデータベースは, 様々な植物種で同定された フラボノイドを報告した文献を 集めたものです。 データベースは 物質、植物種、文献 という 3 つの名前空間で構成されます。 現在 6918 フラボノイド構造, 3653 植物種, そして 4997 文献 に基づく 19851 物質:生物種 の対応関係が登録されています。


Flavonoid content in food 食品中の量

The daily intake of polyphenols from plant foods is considered about 1000 mg/day.

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

以下の野菜やハーブは フラボノイドの含有量が 5 mg/100 g 以下です。 ビーツ, えんどう豆, キャベツ, にんじん, カリフラワー, きゅうり, エンダイブ, ゴード, 長ねぎ, レタス, グリンピース, パプリカ, ポテト, かぶ, トマト, オレガノ, しそ, ローズマリー

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.

このサイトで利用しているフラボノイドIDは、metabolome.jpのFlavonoid Viewerと以下のFL7カテゴリー以外は一致しています。

Anthocyanin glycosylated with other than glucose and galactose
Flavonoid Viewer
FL7A..GS
This site
FL7A..GO

Subcategories

There are 9 subcategories to this category.

F

F cont.

F cont.

Articles in category "FL"

There are 2 articles in this category.

F

I

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