Category:FL

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Flavonoid Database

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
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

Flavonoid is synthesized through both the phenylpropanoid-acetate pathway and the acetate-malonate pathway in all higher plants (but not algae). Most plants contain the 6 major subgroups (chalcones, flavanones, flavones, flavonols, flavans, and anthocyani(di)ns). Aurones or isoflavonoids are not ubiquitous.


4-coumaroyl CoA + malonyl CoA
Arrow00d35.pngCHS
Fl1.png
CHALCONES, AURONES
chalconaringenin
FL1CAANS0001.png
Fl3.png
FLAVONES
apigenin
FL3FAANS0001.png
luteolin
FL3FACNS0001.png
CHI Arrow00d35.png (isomerase) Arrow00ur35.pngFS (oxygenase)

IFS Arrow00dl35.png
naringenin
Fl2.png
FLAVANONE
kaempferol
FL5FAANS0001.png
Fl5.png
FLAVONOLS
quercetin
FL5FACNS0001.png
myricetin
FL5FAGNS0001.png
Fli.png
ISO-FLAVONES
F3H Arrow00d35.png (hydroxylase) Arrow00ur35.png FLS (oxygenase) Arrow00ur35.png FLS Arrow00ur35.png FLS
Fl4.png
DIHYDRO FLAVONOLS
dihydro-kaempferol
FL4DAANS0001.png
F3'H
Arrow00r100.png
+OH in B-ring
dihydro-quercetin
FL4DACNS0001.png
F3'5'H
Arrow00r100.png
+OH in B-ring
dihydro-myricetin
FL4DAGNS0001.png
DFR Arrow00d35.png (reductase) Arrow00d35.pngDFR Arrow00d35.pngDFR
Fl6d.pngflavan diol
LEUCOANTHO-CYANIDINS
leuco-pelargonidin
FL6DAANS0001.png
Arrow00dr35.png
(reductase)
LAR
leuco-cyanidin
FL6DACNS0001.png
Arrow00dr35.png LAR leuco-delphinidin
FL6DAGNS0001.png
Arrow00dr35.png LAR
LDOX Arrow00d35.png (oxygenase) PROANTHO- CYANIDINS *    Arrow00d35.png LDOX    PROANTHO- CYANIDINS *    Arrow00d35.png LDOX    *...polymers of flavanols
Fl7 2.png
ANTHO-CYANIDINS
pelargonidin
FL7AAANS0001.png
Arrow00dr35.pngANR   Arrow00u.png cyanidin
FL7AACNS0001.png
Arrow00dr35.pngANR   Arrow00u.png delphinidin
FL7AAGNS0001.png
Arrow00dr35.pngANR   Arrow00u.png
UF3GT Arrow00d35.png (+sugar) epi-afzelechin
FL63AANS0002.png
Arrow00d35.pngUF3GT epi-catechin
FL63ACNS0002.png
Arrow00d35.pngUF3GT epigallo-catechin
FL63AGNS0003.png
Fl6.png
FLAVAN 3-OLS
Fl7.png
ANTHO-CYANINS
pelargonidin 3-glucoside
FL7AAAGL0002.png
cyanidin 3-glucoside
FL7AACGL0001.png
delphinidin 3-glucoside
FL7AAGGL0002.png
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.

Bioactivity

Tea Related

Others

Photoprotectant, anti-oxidant activity (More Information)

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.

Hypotensive activity

Quercetin in onions and flavanols in cocoa are said to reduce blood pressure in hypertensive animals [1], but their effect or mechanism is not clinically conclusive.

  1. Hooper L, Kroon PA, Rimm EB, et al. (2008) "Flavonoids, flavonoid-rich foods, and cardiovascular risk: a meta-analysis of randomized controlled trials" Am J Clin Nutr 88:38–50 PMID 18614722
Anti-bacteria, anti-fungal activity

Tannins (proanthocyanidins) show anti-bacterial activity.


Database statistics/ranking

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.

class FL1
(chalcones)
FL2
(flavanones)
FL3
(flavones)
FL4
(dihydroflavonols)
FL5
(flavonols)
FL6
(flavans)
FL7
(anthocyanidins)
FLI
(isoflavonoids)
FLN
(neoflavonoids)
Total
#data 690 705 1479 272 1943 291 574 916 96 6961


Flavonoid content in food

For details, please visit this page.

Food containing high Flavanone

Flavanones are rich in citrus, not in vegetables.

Food Flavanone
(mg/100g)
食品名
grapefruit, raw or juice 14-53 グレープフルーツ (生、ジュース)
orange and tangerine, raw or juice 13-33 オレンジ、みかん (生、ジュース)
Food containing high flavone

Many herbs contain flavones. Parsley is rich in apigenin; celery and thyme in luteolin.

Food Flavone
(mg/100g)
食品名
celery hearts, raw 19 セロリの芯 (生)
parsley, raw 302 パセリ (生)
Food containing high flavonol

Flavonols are prevalent in vegetables, usually in small amounts. Onions, kales, hot peppers are good sources.

Food Flavonol
(mg/100g)
食品名
buckwheat 23 そば
cranberry, juice 16 クランベリー (ジュース)
onion, raw or boiled 5-20 たまねぎ (生、ゆで等)
kale, raw or canned 18-34 ケール (生、かんづめ)
Food containing high flavan

Catechins and epicatechins are contained in legumes and teas, but not in other vegetables.

Food Flavan
(mg/100g or 100ml)
食品名
broadbeans, raw ~50 そらまめ (生)
dark chocolate bar ~50 ダークチョコレート
black grapes 18 黒いブドウ
brewed black tea > 16 淹れた紅茶
brewed oolong tea 50 淹れたウーロン茶
brewed green tea > 50 淹れた緑茶
Food containing high anthocyanin

Anthocyanins are contained in berries. Vegetables supply only small amounts.

Food Anthocyanin
(mg/100g)
食品名
blueberries, raw 113 ブルーベリー (生)
sweet cherries, raw 116 さくらんぼ (生)
elderberries, raw 749 エルダーベリー (生)
raspberries, raw 49 ラズベリー (生)
Vegetables and herbs with scarce flavonoids

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

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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