Category:FL

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(→‎{{Bilingual|フラボノイド一般|General Flavonoid}})
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* [[Doc:Tea/Health|Tea and health]]　茶と健康
 
* [[Doc:Tea/Health|Tea and health]]　茶と健康
  
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==={{Bilingual|フラボノイド一般|General Flavonoid}}===
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;{{Bilingual|抗紫外、抗酸化作用|Photoprotectant, anti-oxidant activity}}
 
{{Twocolumn|
 
{{Twocolumn|
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;All flavonoids
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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.  
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''photoprotectant, anti-oxidant'' <br/>
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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. <ref name="Ryan 2002">Ryan KG, Swinny EE, Markham KR, Winefield C (2002) "Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves" Phytochem 59:23-32 PMID 11754940</ref>
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<ref>Li J, Ou-Lee T-M, Raba R, Amundson RG, Last RL (1993) "Arabidopsis flavonoid mutants are hypersensitive to UV-B irradiation" Plant Cell 5: 171-179 PMID 12271060</ref>
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;全フラボノイド
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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。効紫外線効果は効酸化作用に関係しています。
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''抗紫外線、抗酸化作用'' <br/>
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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。効紫外線効果は効酸化作用に関係しています。例えばクエルセチンはケンフェロールよりも効紫外線と効酸化作用がともに強くなります。
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<references/>
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[[Doc:Antioxidant|{{Bilingual|抗酸化作用の詳細|Details of antioxidant activity}}]]
  
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* [Doc:Antioxidant|{{Bilingual|抗酸化作用の詳細|Details of antioxidant activity}}]
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;{{Bilingual|血圧効果作用|Hypotensive activity}}
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{{Twocolumn|
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{{Twocolumn
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|'''Flavanols'''<br/>
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Quercetin in onions and flavanols in cocoa are said to reduce blood pressure in hypertensive animals <ref>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</ref>, but their effect or mechanism is not clinically conclusive.
 
Quercetin in onions and flavanols in cocoa are said to reduce blood pressure in hypertensive animals <ref>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</ref>, but their effect or mechanism is not clinically conclusive.
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|'''フラバノール'''<br/>
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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、その効果や医学的メカニズムははっきりしていません。
 
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、その効果や医学的メカニズムははっきりしていません。
 
}}
 
}}
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<references/>
 
<references/>
  
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{{Twocolumn
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;{{Bilingual|抗菌、抗カビ作用|Anti-bacteria, anti-fungal activity}}
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|'''Tannins (proanthocyanidins)'''
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{{Twocolumn|
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''anti-bacteria, anti-fungi''
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Tannins (proanthocyanidins) show anti-bacterial activity.
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|'''タンニン (プロアントシアニジニン)'''
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|
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''抗菌、抗カビ作用''
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タンニン (プロアントシアニジニン) は一般に抗菌、抗カビ作用があります。
 
}}
 
}}
  

Revision as of 15:21, 30 September 2010

Flavonoid

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 7 major subgroups (chalcones, flavanones, flavones, flavonols, flavans, anthocyanidins, and anthycyanins), but 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

Photoprotectant, anti-oxidant activity

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.

Details of antioxidant 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.

Bioavailability

Flavonoid Dose Observation
catechin[1] 5.8 g 26% was excreted within 24h. m-hydroxyphenyl propionic acid was detected in plasma after 6h
3-O-methyl-catechin[2] 2 g plasma level 11-18 ug/ml within 2h; 38% was excreted as glucuronides and sulphates in urine within 120h
quercetin[3] 64 mg (as fried onion) plasma level 1 uM, 2h later
quercetin[4] 4 g (as supplement) undetected in urine or plasma
decaffeinated green tea[5] 88 mg EGCG, 82 mg EGC, 33 mg ECG, and 32 mg EC plasma level 46-268 ng/ml, 82-206 ng/ml, undetected, and 40-80 ng/ml, respectively.
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.

  1. ↑ Das NP (1971) Biochem Pharmacol 20, 3435-3445
  2. ↑ Hackett AM, Griffiths LA, Wermeille M (1985) Xenobiotica 15, 907-914
  3. ↑ Hollman PCH et al (1995) Am J Clin Nutr 62, 1276-1282; Hollman PCH et al (1996) Free Rad Biol Med 21, 703-707
  4. ↑ Gugler R, Leshik M, Dengler HV (1975) Eur J Clin Pharmacol 9, 229-234
  5. ↑ Lee MT et al (1995) Cancer Epidemiol Biomarkers Prev 41,393-399

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.

F

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