Category:FL

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m (→‎Biosynthesis 生合成)
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! Explanation (解説)
 
! Explanation (解説)
 
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|Flavonoid is synthesized through the phenylpropanoid-acetate pathway in all higher plants. It is responsible for many biological activities including pigments, anti-oxidative or anti-allergic agents, and signaling elements in nodule formation.  Some of them are quite familiar in our daily life.
+
|Flavonoid is synthesized through the phenylpropanoid-acetate pathway in all higher plants (but not algae). Most plants contain the six major subgroups (chalcones, flavones, flavonols, flavandiols, anthycyanins, and proanthocyanidins), but the seventh, aurones, is not ubiquitous.  
 +
 
 +
 
 
|
 
|
 
<!----一般にポリフェノール類は  
 
<!----一般にポリフェノール類は  
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| chalcone synthase
 
| chalcone synthase
 
| Bacterial polyketide synthases, particularly those in fatty acid synthesis (Verwoert et al. 1992)
 
| Bacterial polyketide synthases, particularly those in fatty acid synthesis (Verwoert et al. 1992)
−
| early response against light <ref>Kubasek WL, Shirley BW, McKillop A, Goodman HM, Briggs W, Ausubel FM: Regulation of flavonoid biosynthetic genes in germinating Arabidopsis seedlings. Plant Cell 1992 4:1229-1236</ref> <ref>Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445</ref>
+
| Early response against light <ref>Kubasek WL, Shirley BW, McKillop A, Goodman HM, Briggs W, Ausubel FM: Regulation of flavonoid biosynthetic genes in germinating Arabidopsis seedlings. Plant Cell 1992 4:1229-1236</ref> <ref>Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445</ref>
 
|-
 
|-
 
| CHI
 
| CHI
 
| chalcone-flavanone isomerase
 
| chalcone-flavanone isomerase
−
| Unclear. ''Eubacterium ramulus'' has the CHI activity. <ref>Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from ''Eubacterium ramulus''. Arch Microbiol 2004 181:428-434.</ref>
+
| Unclear and unique to plants.<ref>Jez JM, Bowman ME, Dixon RA, Noel JP: Structure and mechanism of chalcone isomerase: an evolutionarily unique enzyme in plants. Nat Struct Biol 2000 7: 786–791</ref>
−
| early response against light
+
''Eubacterium ramulus'' has the CHI activity. <ref>Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from ''Eubacterium ramulus''. Arch Microbiol 2004 181:428-434.</ref>
 +
| Early response against light.
 
|-
 
|-
 
| F3H
 
| F3H
 
| flavanone 3-hydroxylase
 
| flavanone 3-hydroxylase
 
| 2-oxoglutarate-dependent dioxygenase family <ref>Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492</ref>
 
| 2-oxoglutarate-dependent dioxygenase family <ref>Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492</ref>
−
| early response in Arabidopsis but late in Antirrhinum <ref>Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers ''Antirrhinum majus''. Plant J 1991 1:37-49</ref>
+
| Early response in Arabidopsis but late in Antirrhinum <ref>Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers ''Antirrhinum majus''. Plant J 1991 1:37-49</ref>
 
|-
 
|-
 
| FLS
 
| FLS
 
| flavonol synthase
 
| flavonol synthase
 
| 2-oxoglutarate-dependent dioxygenase family <ref>Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083</ref>
 
| 2-oxoglutarate-dependent dioxygenase family <ref>Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083</ref>
−
| early response against light
+
| Early response against light. In Arabidopsis, all structural genes are single-copy except for this one, to which six genes exist and two of them are not expressed.
 
|-
 
|-
 
| DFR
 
| DFR
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| NADPH-dependent reductase associated with steroid metabolism <ref>Baker ME, Blasco RE: Expansion of the mammalian 3bhydroxysteroid dehydrogenase/plant dihydroflavonol reductase superfamily to include a bacterial cholesterol dehydrogenase, a bacterial UDP-galactose 4-epimerase, and open reading frames in vaccinia virus and fish lymphocystis disease virus.
 
| NADPH-dependent reductase associated with steroid metabolism <ref>Baker ME, Blasco RE: Expansion of the mammalian 3bhydroxysteroid dehydrogenase/plant dihydroflavonol reductase superfamily to include a bacterial cholesterol dehydrogenase, a bacterial UDP-galactose 4-epimerase, and open reading frames in vaccinia virus and fish lymphocystis disease virus.
 
FEBS Lett 1992 301: 89–93</ref>
 
FEBS Lett 1992 301: 89–93</ref>
−
| later response
+
| Later response
 
|-
 
|-
 
| ANS/LDOX
 
| ANS/LDOX
 
| anthocyanidin synthase or leucoanthocyanidin dioxygenase
 
| anthocyanidin synthase or leucoanthocyanidin dioxygenase
 
| 2-oxoglutarate-dependent dioxygenase family
 
| 2-oxoglutarate-dependent dioxygenase family
−
| later response
+
| Later response
 
|-
 
|-
 
! colspan=4| Auxiliary Genes (その他の遺伝子)
 
! colspan=4| Auxiliary Genes (その他の遺伝子)
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| flavonoid 3',5'-hydroxylase
 
| flavonoid 3',5'-hydroxylase
 
| cytochrome P450 hydroxylase family <ref>Holton TA, Brugliera F, Lester DR, Tanaka Y, Hyland CD, Menting JGT, Lu CY, Farcy E, Stevenson TW, Cornish EC: Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993 366:276–279</ref>
 
| cytochrome P450 hydroxylase family <ref>Holton TA, Brugliera F, Lester DR, Tanaka Y, Hyland CD, Menting JGT, Lu CY, Farcy E, Stevenson TW, Cornish EC: Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993 366:276–279</ref>
−
| Not reported in mosses or liverworts.
+
| Not reported in mosses or liverworts. The transformation of the F3'5'H and the cytochrome b5 gene of petunia into carnation changed its flower color deep purple.<ref>de Vetten N, ter Horst J, van Schaik H-P, de Boer A, Mol J, Koes R: A cytochrome b5 is required for full activity of flavonoid 39,59-hydroxylase, a cytochrome P450 involved in the formation of blue flowers. Proc Natl Acad Sci USA 1999 96: 778–783</ref><ref>Brugliera F, Tull D, Holton TA, Karan M, Treloar N,
 +
Simpson K, Skurczynska J, Mason JG: Introduction of a cytochrome b5 enhances the activity of flavonoid 3'5' hydroxylase (a cytochrome P450) in transgenic carnation. Sixth International Congress of Plant Molecular Biology. University of Laval, Quebec, 2000 pp S6–S8</ref>
 +
|-
 +
| FSI
 +
| flavone synthase
 +
| Dioxygenase in parsley (FSI) and P450 monooxygenase in snapdragon (FSII).
 +
|-
 +
| LAR (or LCR)
 +
| leucoanthocyanidin reductase
 +
|
 
|-
 
|-
 
| UF3GT
 
| UF3GT
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| GST
 
| GST
 
| glutathione-S-transferase
 
| glutathione-S-transferase
 +
|
 +
| Transport of flavonoids from cytoplasm to vacuole or cell walls requires both GST and the glutathione pump in ATP-binding cassette family.<ref>Marrs KA, Alfenito MR, Lloyd AM, Walbot V: A glutathione S-transferase involved in vacuolar transfer encoded by the maise gene Bronze-2. Nature 1995 375: 397–400</ref><ref>Alfenito MR, Souer E, Goodman CD, Buell R, Mol J, Koes R, Walbot V: Functional complementation of anthocyanin sequestration in the vacuole by widely divergent
 +
glutathione S-transferases. Plant Cell 1998 10: 1135–1149</ref>
 +
|-
 +
| AOMT
 +
| anthocyanin O-methyl transferase
 
|}
 
|}
  

Revision as of 21:30, 22 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
Leucoanthocyanidin
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

Biosynthesis 生合成

4-coumaroyl CoA + malonyl CoA
Arrow00d35.pngCHS
CHALCONES, AURONES chalcone FLAVONES
Arrow00d35.pngCHI ／FS
IFS ／ FLAVANONE
naringenin 		kaempferol FLAVONOLS quercetin myricetin
ISO-FLAVONES Arrow00d35.pngF3H ／ FLS ／ FLS ／ FLS
DIHYDRO FLAVONOLS dihydro-kaempferol F3'H
Arrow00r.png 		dihydro-quercetin F3'5'H
Arrow00r.png 		dihydro-myricetin
Arrow00d35.pngDFR Arrow00d35.pngDFR Arrow00d35.pngDFR
LEUCOANTHO-CYANIDINS
(flavan diols) 		leuco-pelargonidin LAR
Arrow00r35.png 		leuco-cyanidin LAR
Arrow00r35.png 		leuco-delphinidin LAR
Arrow00r35.png
Arrow00d35.pngANS/LDOX PROANTHO- CYANIDINS Arrow00d35.pngANS/LDOX PROANTHO- CYANIDINS Arrow00d35.pngANS/LDOX PROANTHO- CYANIDINS
ANTHO-CYANIDINS pelargonidin ANR
Arrow00r35.png 		Arrow00u35.png cyanidin ANR
Arrow00r35.png 		Arrow00u35.png delphinidin ANR
Arrow00r35.png 		Arrow00u35.png
Arrow00d35.pngUF3GT epi-afzelechin Arrow00d35.pngUF3GT epi-catechin Arrow00d35.pngUF3GT epigallo-catechin
ANTHO-CYANINS pelargonidin 3-glucoside cyanidin 3-glucoside delphinidin 3-glucoside FLAVAN 3-OLS
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.
Arrow00d35.png UF5GT, AOMT etc.
Six Structural Genes (6つの構造遺伝子)
Abbrev. Name Origin Information
CHS chalcone synthase Bacterial polyketide synthases, particularly those in fatty acid synthesis (Verwoert et al. 1992) Early response against light [1] [2]
CHI chalcone-flavanone isomerase Unclear and unique to plants.[3]

Eubacterium ramulus has the CHI activity. [4]

Early response against light.
F3H flavanone 3-hydroxylase 2-oxoglutarate-dependent dioxygenase family [5] Early response in Arabidopsis but late in Antirrhinum [6]
FLS flavonol synthase 2-oxoglutarate-dependent dioxygenase family [7] Early response against light. In Arabidopsis, all structural genes are single-copy except for this one, to which six genes exist and two of them are not expressed.
DFR dihydroflavonol 4-reductase NADPH-dependent reductase associated with steroid metabolism [8] Later response
ANS/LDOX anthocyanidin synthase or leucoanthocyanidin dioxygenase 2-oxoglutarate-dependent dioxygenase family Later response
Auxiliary Genes (その他の遺伝子)
F3'H flavonoid 3'-hydroxylase cytochrome P450 hydroxylase family [9]
F3'5'H flavonoid 3',5'-hydroxylase cytochrome P450 hydroxylase family [10] Not reported in mosses or liverworts. The transformation of the F3'5'H and the cytochrome b5 gene of petunia into carnation changed its flower color deep purple.[11][12]
FSI flavone synthase Dioxygenase in parsley (FSI) and P450 monooxygenase in snapdragon (FSII).
LAR (or LCR) leucoanthocyanidin reductase
UF3GT UDP flavonoid glucosyltransferase
GST glutathione-S-transferase Transport of flavonoids from cytoplasm to vacuole or cell walls requires both GST and the glutathione pump in ATP-binding cassette family.[13][14]
AOMT anthocyanin O-methyl transferase
  1. ↑ Kubasek WL, Shirley BW, McKillop A, Goodman HM, Briggs W, Ausubel FM: Regulation of flavonoid biosynthetic genes in germinating Arabidopsis seedlings. Plant Cell 1992 4:1229-1236
  2. ↑ Pelletier MK, Murrell JR, Shirley BW: Characterization of flavonol synthase and leucoanthocyanidins dioxygenase genes in Arabidopsis. Plant Physiol 1997 113:1437-1445
  3. ↑ Jez JM, Bowman ME, Dixon RA, Noel JP: Structure and mechanism of chalcone isomerase: an evolutionarily unique enzyme in plants. Nat Struct Biol 2000 7: 786–791
  4. ↑ Herles C, Braune A, Braut M: First bacterial chalcone isomerase isolated from Eubacterium ramulus. Arch Microbiol 2004 181:428-434.
  5. ↑ Winkel-Shirley B: Flavonoid biosynthesis. A colorful model for genetics, biochemistry, cell biology and biotechnology. Plant Physiol 2001 126:485-492
  6. ↑ Martin C, Prescott A, Mackay S, Bartlett J, Vrijlandt E: Control of anthocyanin biosyntehsis in flowers Antirrhinum majus. Plant J 1991 1:37-49
  7. ↑ Holton TA, Cornish EC: Genetics and biochemistry of anthocyanin biosynthesis. Plant Cell 1993 7:1071-1083
  8. ↑ Baker ME, Blasco RE: Expansion of the mammalian 3bhydroxysteroid dehydrogenase/plant dihydroflavonol reductase superfamily to include a bacterial cholesterol dehydrogenase, a bacterial UDP-galactose 4-epimerase, and open reading frames in vaccinia virus and fish lymphocystis disease virus. FEBS Lett 1992 301: 89–93
  9. ↑ Brugliera F, Barri-Rewell G, Holton TA, Mason JG: Isolation and characterization of a flavonoid 3-hydroxylase. cDNA clone corresponding to the Ht1 locus of Petunia hybrida. Plant J 1999 19: 441–451
  10. ↑ Holton TA, Brugliera F, Lester DR, Tanaka Y, Hyland CD, Menting JGT, Lu CY, Farcy E, Stevenson TW, Cornish EC: Cloning and expression of cytochrome P450 genes controlling flower colour. Nature 1993 366:276–279
  11. ↑ de Vetten N, ter Horst J, van Schaik H-P, de Boer A, Mol J, Koes R: A cytochrome b5 is required for full activity of flavonoid 39,59-hydroxylase, a cytochrome P450 involved in the formation of blue flowers. Proc Natl Acad Sci USA 1999 96: 778–783
  12. ↑ Brugliera F, Tull D, Holton TA, Karan M, Treloar N, Simpson K, Skurczynska J, Mason JG: Introduction of a cytochrome b5 enhances the activity of flavonoid 3'5' hydroxylase (a cytochrome P450) in transgenic carnation. Sixth International Congress of Plant Molecular Biology. University of Laval, Quebec, 2000 pp S6–S8
  13. ↑ Marrs KA, Alfenito MR, Lloyd AM, Walbot V: A glutathione S-transferase involved in vacuolar transfer encoded by the maise gene Bronze-2. Nature 1995 375: 397–400
  14. ↑ Alfenito MR, Souer E, Goodman CD, Buell R, Mol J, Koes R, Walbot V: Functional complementation of anthocyanin sequestration in the vacuole by widely divergent glutathione S-transferases. Plant Cell 1998 10: 1135–1149

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

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.

F

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