Category:FL

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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. (BY Masanori Arita)

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
Leucoanthocyanidin
フラバン
Fl6.png
tea, cocoa
お茶、ココア
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

Biosynthesis 生合成

4-coumaroyl CoA + malonyl CoA
Arrow00d35.pngCHS
CHALCONES, AURONES chalcone FLAVONES
Arrow00d35.pngCHI Arrow00ur35.pngFS

IFS Arrow00dl35.png
FLAVANONE
naringenin
kaempferol FLAVONOLS quercetin myricetin
ISO-FLAVONES Arrow00d35.pngF3H Arrow00ur35.png FLS Arrow00ur35.png FLS Arrow00ur35.png FLS
DIHYDRO FLAVONOLS dihydro-kaempferol F3'H
Arrow00r100.png
dihydro-quercetin F3'5'H
Arrow00r100.png
dihydro-myricetin
Arrow00d35.pngDFR Arrow00d35.pngDFR Arrow00d35.pngDFR
LEUCOANTHO-CYANIDINS
(flavan diols)
leuco-pelargonidin Arrow00dr35.png LAR leuco-cyanidin Arrow00dr35.png LAR leuco-delphinidin Arrow00dr35.png LAR
Arrow00d35.png LDOX PROANTHO- CYANIDINS    Arrow00d35.png LDOX    PROANTHO- CYANIDINS    Arrow00d35.png LDOX    PROANTHO- CYANIDINS
ANTHO-CYANIDINS pelargonidin Arrow00dr35.pngANR   Arrow00u35.png cyanidin Arrow00dr35.pngANR   Arrow00u35.png delphinidin Arrow00dr35.pngANR   Arrow00u35.png
Arrow00d35.pngUF3GT epi-afzelechin Arrow00d35.pngUF3GT epi-catechin Arrow00d35.pngUF3GT epigallo-catechin FLAVAN 3-OLS
ANTHO-CYANINS pelargonidin 3-glucoside cyanidin 3-glucoside delphinidin 3-glucoside
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.

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][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。

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, 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

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.

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