Category:FL

From Metabolomics.JP
(Difference between revisions)
Jump to: navigation, search
m (→‎Bioactivity)
m
 
(51 intermediate revisions by one user not shown)
Line 1: Line 1:
−
{{Huge|Flavonoid (フラボノイド)}}
+
{{Huge|{{Bilingual|フラボノイドのデータベース|Flavonoid Database}}}}
−
[[Image:FL.gif|thumb|150px|right|Figure 1: The Backbone of Flavonoid Structure]]
+
{|  
−
 
+
| __TOC__
 +
|}
 
{{Flavonoid/Header}}
 
{{Flavonoid/Header}}
  
−
==Class Overview==
+
=={{Bilingual|フラボノイドの概要|Class Overview}}==
  
 
{{Twocolumn
 
{{Twocolumn
 
|
 
|
−
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 [[:Category:FL3F|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 word "flavonoid" comes from its Latin origin ''flavus'' (yellow), meaning yellow-ish.  It comes from its history as yellow natural dye (quercetin and kaempferol are the most widespread flavone dyes. See [[:Category:FL3F|flavone]]).
−
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).
+
−
<br>
+
−
Flavonoid is utilized in many industrial processes from pigments to food additives.  Often heard names include anthocyanin, catechin, flavan, and isoflavone. {{WrittenBy|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 ([[:Category:FL3F|flavone]]参照)。
 
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 ([[:Category:FL3F|flavone]]参照)。
−
 
+
}}
 +
{{Twocolumn
 +
|
 +
In chemistry terms, 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).
 +
|
 
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)。
 
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)。
+
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)。}}
−
 
+
[[Image:FL.gif|thumb|150px|right|Figure 1: The Backbone of Flavonoid Structure]]
−
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。 {{WrittenBy|有田正規}}
+
{{Twocolumn
 +
|
 +
Flavonoid is utilized in many industrial processes from pigments to food additives.  Well known names include anthocyanin, catechin, flavan, and isoflavone.
 +
|
 +
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。
 
}}
 
}}
  
 
<center>
 
<center>
−
{| class="wikitable"
+
{| class="wikitable" style="text-align:center"
 
|+ Table 1. Flavonoid Classification
 
|+ Table 1. Flavonoid Classification
 
|-
 
|-
 
!colspan="3"|1st Class
 
!colspan="3"|1st Class
 
|- valign="top"
 
|- valign="top"
−
|align="center"|[[:Category:FL1|FL1: Anthochlor<br/> (Aurone and Chalcone)]]<br>オーロン、カルコン<br>[[Image:Fl1.png|100px]]<br>safflower yellow<br>紅花（末摘花）の黄色
+
|[[:Category:FL1|FL1: Anthochlor<br/>({{Bilingual|オーロン、カルコン|Aurone and Chalcone}})]]<br/>
−
|align="center"|[[:Category:FL2|FL2: Flavanone]]<br>フラバノン<br>[[Image:Fl2.png|100px]]<br>white skin of orange<br>みかんジュースの白沈
+
[[Image:Fl1.png|100px]]<br/>{{Bilingual|紅花（末摘花）の黄色|safflower yellow}}
−
|align="center"|[[:Category:FL3|FL3: Flavone]]<br>フラボン<br>[[Image:Fl3.png|100px]]<br>herbs like parsley<br>セロリやパセリ等ハーブ
+
|[[:Category:FL2|FL2: {{Bilingual|フラバノン|Flavanone}}]]<br/>
 +
[[Image:Fl2.png|100px]]<br/>{{Bilingual|みかんジュースの白沈|white skin of orange}}
 +
|[[:Category:FL3|FL3: {{Bilingual|フラボン|Flavone}}]]<br/>
 +
[[Image:Fl3.png|100px]]<br>{{Bilingual|セロリやパセリ等ハーブ|herbs like parsley, yellow dye}}
 
|- valign="top"
 
|- valign="top"
 
|
 
|
Line 44: Line 54:
 
  |[[:Category:FL1D|FL1D]]||[[:Category:FL1D|Dihydrochalcone]]<br>[[Image:Fl1d.png|120px]]
 
  |[[:Category:FL1D|FL1D]]||[[:Category:FL1D|Dihydrochalcone]]<br>[[Image:Fl1d.png|120px]]
 
  |}
 
  |}
−
|align="center" valign="center"| [[:Category:FL2F|FL2F: Flavanone]]
+
|  
−
<!---{| class="collapsible collapsed" border="1" cellspacing="0" width="150"
+
|  
−
|-
+
−
! colspan="2"|2nd Class
+
−
|-
+
−
|[[:Category:FL2F|FL2F]]||[[:Category:FL2F|Flavanone]]
+
−
|}--->
+
−
|align="center" valign="center"|[[:Category:FL3F|FL3F: Flavone]]
+
 
|- valign="top"
 
|- valign="top"
−
|align="center"|[[:Category:FL4|FL4: Dihydroflavonol]]<br/>ジヒドロフラボノール<br>[[Image:Fl4.png|100px]]<br/>antioxidant in grapes<br/>ブドウの抗酸化成分
+
|[[:Category:FL4|FL4: {{Bilingual|ジヒドロフラボノール|Dihydroflavonol}}]]<br/>
−
|align="center"|[[:Category:FL5|FL5: Flavonol]]<br>フラボノール<br>[[Image:Fl5.png|100px]]<br/>vegetables such as onion<br>たまねぎ等多くの野菜
+
[[Image:Fl4.png|100px]]<br/>{{Bilingual|ブドウの抗酸化成分|antioxidant in grapes}}
−
|align="center"|[[:Category:FL6|FL6: Flavan]]<br/>Leucoanthocyanidin<br/>フラバン<br>[[Image:Fl6.png|100px]]<br/>tea, cocoa<br/>お茶、ココア
+
|[[:Category:FL5|FL5: {{Bilingual|フラボノール|Flavonol}}]]<br/>
 +
[[Image:Fl5.png|100px]]<br/>{{Bilingual|たまねぎ等多くの野菜|vegetables such as onion}}
 +
|[[:Category:FL6|FL6: {{Bilingual|フラバン|Flavan}}<br/>({{Bilingual|ロイコアントシアニジン|Leucoanthocyanidin}})]]<br/>
 +
[[Image:Fl6.png|100px]]<br/>{{Bilingual|お茶、ココア|tea, cocoa}}
 
|- valign="top"
 
|- valign="top"
−
|align="center"| [[:Category:FL4D|FL4D: Dihydroflavonol]]
+
|  
−
|align="center"| [[:Category:FL5F|FL5F: Flavonol]]
+
|
−
||
+
|
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  |-
 
  |-
Line 73: Line 80:
 
  |}
 
  |}
 
|- valign="top"
 
|- valign="top"
−
|align="center"|[[:Category:FL7|FL7: Anthocyani(di)n]]<br>アントシアニ(ジ)ン<br>[[Image:Fl7.png|100px]]<br>purple vegetables/fruits<br>(赤)紫の野菜、果物
+
|[[:Category:FL7|FL7: {{Bilingual|アントシアニ(ジ)ン|Anthocyani(di)n}}]]<br/>
−
|align="center"|[[:Category:FLI|FLI: Isoflavonoid]]<br>イソフラボノイド<br>[[Image:Fli.png|100px]]<br>beans<br>豆類
+
[[Image:Fl7.png|120px]]<br/>{{Bilingual|(赤)紫の野菜、果物|purple vegetables/fruits}}
−
|align="center"|[[:Category:FLN|FLN: Neoflavonoid]]<br>ネオフラボノイド<br>[[Image:Fln.png|75px]]
+
|[[:Category:FLI|FLI: {{Bilingual|イソフラボノイド|Isoflavonoid}}]]<br/>
 +
[[Image:Fli.png|100px]]<br>{{Bilingual|豆類|beans}}
 +
|[[:Category:FLN|FLN: {{Bilingual|ネオフラボノイド|Neoflavonoid}}]]<br/>
 +
[[Image:Fln.png|75px]]
 
|- valign="top"
 
|- valign="top"
 
|
 
|
Line 86: Line 96:
 
  |[[:Category:FL7D|FL7D]]||[[:Category:FL7D|3-Deoxyanthocyanin]]<br>[[Image:Fl7d.png|90px]]
 
  |[[:Category:FL7D|FL7D]]||[[:Category:FL7D|3-Deoxyanthocyanin]]<br>[[Image:Fl7d.png|90px]]
 
  |}
 
  |}
−
||
+
|
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  |-
 
  |-
Line 111: Line 121:
 
  |[[:Category:FLIJ|FLIJ]]||[[:Category:FLIJ|alpha-Methoxynbenzoin]]<br>[[Image:Flij.png|90px]]
 
  |[[:Category:FLIJ|FLIJ]]||[[:Category:FLIJ|alpha-Methoxynbenzoin]]<br>[[Image:Flij.png|90px]]
 
  |}
 
  |}
−
||
+
|
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  {| class="collapsible collapsed" border="1" cellspacing="0" width="150"
 
  |-
 
  |-
Line 130: Line 140:
 
|}
 
|}
 
</center>
 
</center>
−
<!--- Class Information (Do not delete. It is used by Template:Hierarchy.)
+
<!--- Class Information (Do not delete. This list is used by Template:Hierarchy.)
 
&&FL&&Flavonoid&&
 
&&FL&&Flavonoid&&
 
&&FL1&&Aurone and Chalcone&&
 
&&FL1&&Aurone and Chalcone&&
Line 145: Line 155:
 
&&FL64&&Flavan 4-ol&&
 
&&FL64&&Flavan 4-ol&&
 
&&FL6D&&Flavan 3,4-diol&&
 
&&FL6D&&Flavan 3,4-diol&&
−
&&FL7&&Anthocyanin&&
+
&&FL7&&Anthocyani(di)n&&
−
&&FL7A&&Anthocyanin&&
+
&&FL7A&&Anthocyani(di)n&&
 
&&FL7D&&3-Deoxyanthocyanin&&
 
&&FL7D&&3-Deoxyanthocyanin&&
 
&&FLI&&Isoflavonoid&&
 
&&FLI&&Isoflavonoid&&
Line 166: Line 176:
 
&&FLNE&&Neoflavene&&
 
&&FLNE&&Neoflavene&&
 
&&FLNF&&Coumarinic acid&&
 
&&FLNF&&Coumarinic acid&&
 +
&&FLT&&Condensed Tannin
 
--->
 
--->
  
−
==Biosynthesis 生合成==
+
==[[:Category:FL/Biosynthesis|{{Bilingual|生合成のページヘ|Biosynthesis}}]]==
  
−
{| class="collapsible collapsed"
+
==[[:Category:FL/Bioactivity|{{Bilingual|生物活性のページヘ|Bioactivity}}]]==
−
! Explanation (解説)
+
−
|-
+
−
|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
+
−
# フェニルプロパノイド経路 から生合成されるもの　と
+
−
# 酢酸－マロン酸経路 から生合成されるもの
+
−
にわかれます。 たとえば, 1 では、クマリン, リグナン, リグニンなどが生合成され, 2 の酢酸－マロン酸経路では, アントラキノンが知られています。
+
−
フラボノイドは, 上記 2 つの, 脂肪酸フェニルプロパノイド経路と 酢酸-マロン酸パスウェイとの 組み合わせにより生合成されます。 同様のパスウェイから生成される産物には, キサントン, スチルベンなどがあります。
+
−
----->
+
−
|}
+
−
 
+
−
{| style="text-align:center"
+
−
|-
+
−
| colspan="4"| 4-coumaroyl CoA + malonyl CoA
+
−
|-
+
−
|
+
−
| [[Image:Arrow00d35.png]]CHS
+
−
|-
+
−
| style="background:lightyellow"| [[:Category:FL1|''CHALCONES, AURONES'']]
+
−
| style="background:lightyellow"| chalcone
+
−
|
+
−
| style="background:mistyrose"| [[:Category:FL2|''FLAVONES'']]
+
−
|-
+
−
|
+
−
| [[Image:Arrow00d35.png]]CHI
+
−
| colspan="2" style="text-align:left" | [[Image:Arrow00ur35.png]]FS
+
−
|-
+
−
| style="text-align:right"|<br/>IFS [[Image:Arrow00dl35.png]]
+
−
| style="background:whitesmoke"| [[:Category:FL2| ''FLAVANONE''<br/>naringenin]]
+
−
|
+
−
| style="background:lightyellow"| kaempferol
+
−
| style="background:lightyellow" colspan="3" | [[:Category:FL5|''FLAVONOLS'']]
+
−
| style="background:lightyellow"| quercetin
+
−
|
+
−
| style="background:lightyellow"| myricetin
+
−
|-
+
−
| style="background:oldlace"| [[:Category:FLI|''ISO-FLAVONES'']]
+
−
| [[Image:Arrow00d35.png]]F3H       
+
−
| colspan="2" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS
+
−
|
+
−
|
+
−
| colspan="2" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS
+
−
|
+
−
| colspan="2" style="text-align:left"|[[Image:Arrow00ur35.png]] FLS   
+
−
|-
+
−
| style="background:ghostwhite"| [[:Category:FL4|''DIHYDRO FLAVONOLS'']]
+
−
| style="background:ghostwhite"| dihydro-kaempferol
+
−
| colspan="3"| F3'H<br/>[[Image:Arrow00r100.png]]
+
−
| style="background:ghostwhite"| dihydro-quercetin
+
−
| colspan="3"| F3'5'H<br/>[[Image:Arrow00r100.png]]
+
−
| style="background:ghostwhite"| dihydro-myricetin
+
−
|-
+
−
|
+
−
| [[Image:Arrow00d35.png]]DFR
+
−
|
+
−
|
+
−
|
+
−
| [[Image:Arrow00d35.png]]DFR
+
−
|
+
−
|
+
−
|
+
−
| [[Image:Arrow00d35.png]]DFR
+
−
|
+
−
|-
+
−
| style="background:azure"| [[:Category:FL6|''LEUCOANTHO-CYANIDINS'']]<br/><small>(flavan diols)</small>
+
−
| style="background:azure"| leuco-pelargonidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="3"|[[Image:Arrow00dr35.png]] LAR
+
−
| style="background:azure"| leuco-cyanidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="3"|[[Image:Arrow00dr35.png]] LAR
+
−
| style="background:azure"| leuco-delphinidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="2"|[[Image:Arrow00dr35.png]] LAR
+
−
|
+
−
|-
+
−
|
+
−
| [[Image:Arrow00d35.png]] LDOX
+
−
|
+
−
| style="background:papayawhip"| ''PROANTHO- CYANIDINS''
+
−
| &nbsp;&nbsp;
+
−
| [[Image:Arrow00d35.png]] LDOX
+
−
| &nbsp;&nbsp;
+
−
| style="background:papayawhip"| ''PROANTHO- CYANIDINS''
+
−
| &nbsp;&nbsp;
+
−
| [[Image:Arrow00d35.png]] LDOX
+
−
| &nbsp;&nbsp;
+
−
| style="background:papayawhip"| ''PROANTHO- CYANIDINS''
+
−
|-
+
−
| style="background:mistyrose"| [[:Category:FL7|''ANTHO-CYANIDINS'']]
+
−
| style="background:mistyrose"| pelargonidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="2" | [[Image:Arrow00dr35.png]]ANR &nbsp; [[Image:Arrow00u35.png]]
+
−
|
+
−
| style="background:mistyrose"| cyanidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="2" | [[Image:Arrow00dr35.png]]ANR &nbsp; [[Image:Arrow00u35.png]]
+
−
|
+
−
| style="background:mistyrose"| delphinidin
+
−
| style="text-align:left;vertical-align:bottom" colspan="2" | [[Image:Arrow00dr35.png]]ANR &nbsp; [[Image:Arrow00u35.png]]
+
−
|-
+
−
|
+
−
| [[Image:Arrow00d35.png]]UF3GT
+
−
|
+
−
| style="background:beige"| epi-afzelechin
+
−
|
+
−
| [[Image:Arrow00d35.png]]UF3GT
+
−
|
+
−
| style="background:beige"| epi-catechin
+
−
|
+
−
| [[Image:Arrow00d35.png]]UF3GT
+
−
|
+
−
| style="background:beige"| epigallo-catechin
+
−
| style="background:beige"| [[:Category:FL6|''FLAVAN 3-OLS'']]
+
−
|-
+
−
| style="background:lavender"| [[:Category:FL7|''ANTHO-CYANINS'']]
+
−
| style="background:lavender"| pelargonidin 3-glucoside
+
−
|
+
−
|
+
−
|
+
−
| style="background:lavender"| cyanidin 3-glucoside
+
−
|
+
−
|
+
−
|
+
−
| style="background:lavender"| delphinidin 3-glucoside
+
−
|-
+
−
|
+
−
|
+
−
{|
+
−
|[[Image:Arrow00d35.png]]
+
−
|UF5GT, AOMT etc.
+
−
|}
+
−
|
+
−
|
+
−
|
+
−
|
+
−
{|
+
−
|[[Image:Arrow00d35.png]]
+
−
|UF5GT, AOMT etc.
+
−
|}
+
−
|
+
−
|
+
−
|
+
−
|
+
−
{|
+
−
|[[Image:Arrow00d35.png]]
+
−
|UF5GT, AOMT etc.
+
−
|}
+
−
|}
+
−
 
+
−
{| class="wikitable collapsible collapsed"
+
−
! colspan=4| Information for the Gene Abbreviations (遺伝子略称の詳細)
+
−
|-
+
−
! colspan=4| Six Structural Genes (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 <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
+
−
| chalcone-flavanone isomerase
+
−
| 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>
+
−
''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
+
−
| 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>
+
−
| 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
+
−
| 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>
+
−
| 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 <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>
+
−
| Later response
+
−
|-
+
−
| ANS/LDOX
+
−
| anthocyanidin synthase or leucoanthocyanidin dioxygenase
+
−
| 2-oxoglutarate-dependent dioxygenase family
+
−
| Later response
+
−
|-
+
−
! colspan=4| Auxiliary Genes (その他の遺伝子)
+
−
|-
+
−
| F3'H
+
−
| flavonoid 3'-hydroxylase
+
−
| cytochrome P450 hydroxylase family <ref>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</ref>
+
−
|-
+
−
| F3'5'H
+
−
| 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>
+
−
| 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
+
−
| 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.<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
+
−
|-
+
−
| colspan="4"| <references/>
+
−
|}
+
−
 
+
−
==Bioactivity==
+
−
{|
+
−
|-
+
−
|'''All flavonoids'''
+
−
''photoprotectant, anti-oxidant'' <br/>
+
−
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: Flavonoid gene expression and UV photoprotection in transgenic and mutant Penunia leaves. Phytochem 2002 59:23-32</ref><ref>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</ref>
+
−
|'''全フラボノイド'''
+
−
''抗紫外線、抗酸化作用'' <br/>
+
−
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'''<br/>
+
−
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'''<br/>
+
−
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''
+
−
|}
+
−
 
+
−
<references/>
+
−
 
+
−
==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 &beta;-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 <small>耳にする名前</small>==
 
−
<div style="column-count:2; -moz-column-count:2;">
 
−
* [[:Category:FLI|isoflavonoid]] in beans (豆のイソフラボン)
 
−
* [[:Category:FL7|anthocyanin]] in berries (ベリーのアントシアニン)
 
−
* [[FL63ACNS0001|catechin]] in tea (お茶のカテキン)
 
−
* [[FL5FACGL0013|rutin]] in buckwheat (ソバのルチン)
 
−
* [[FL2FAEGS0001|hesperidin]] in orange (ミカンのヘスペリジン)
 
−
* [[FL1CAANS0001|naringenin chalcone]] in tomato (トマトのナリンゲニンカルコン)
 
−
</div>
 
  
−
==Database statistics/ranking データベース統計==
+
=={{Bilingual|データベース統計|Database statistics/ranking}}==
 
{{#DEF:NumberOfMolecules|{{#countTitle:FL|}}}}
 
{{#DEF:NumberOfMolecules|{{#countTitle:FL|}}}}
 
{{#DEF:NumberOfSpecies|{{#countTitle:.+|Species}}}}
 
{{#DEF:NumberOfSpecies|{{#countTitle:.+|Species}}}}
 
{{#DEF:NumberOfReferences|{{#expr:{{#countTitle:.+|Reference}}-{{#countTitle:^Country|Reference}} }} }}
 
{{#DEF:NumberOfReferences|{{#expr:{{#countTitle:.+|Reference}}-{{#countTitle:^Country|Reference}} }} }}
 
{{#DEF:NumberOfRelations|{{#countLine:^&&_%&&FL|Reference}}}}
 
{{#DEF:NumberOfRelations|{{#countLine:^&&_%&&FL|Reference}}}}
−
 
+
{{#DEF:FL1Num|{{#countTitle:FL1|}}}}
 +
{{#DEF:FL2Num|{{#countTitle:FL2|}}}}
 +
{{#DEF:FL3Num|{{#countTitle:FL3|}}}}
 +
{{#DEF:FL4Num|{{#countTitle:FL4|}}}}
 +
{{#DEF:FL5Num|{{#countTitle:FL5|}}}}
 +
{{#DEF:FL6Num|{{#countTitle:FL6|}}}}
 +
{{#DEF:FL7Num|{{#countTitle:FL7|}}}}
 +
{{#DEF:FLINum|{{#countTitle:FLI|}}}}
 +
{{#DEF:FLNNum|{{#countTitle:FLN|}}}}
 
{{Twocolumn|
 
{{Twocolumn|
 
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, {{#var:NumberOfMolecules}} flavonoid structures, {{#var:NumberOfSpecies}} plant species, and {{#var:NumberOfReferences}} references describing total {{#var:NumberOfRelations}} metabolite-species relationships are registered.
 
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, {{#var:NumberOfMolecules}} flavonoid structures, {{#var:NumberOfSpecies}} plant species, and {{#var:NumberOfReferences}} references describing total {{#var:NumberOfRelations}} metabolite-species relationships are registered.
Line 457: Line 208:
 
の対応関係が登録されています。
 
の対応関係が登録されています。
 
}}
 
}}
−
 
+
{| class="wikitable" style="text-align:center"
 +
! class
 +
| [[:Category:FL1|FL1]]<br/><small>(chalcones)</small>
 +
| [[:Category:FL2|FL2]]<br/><small>(flavanones)</small>
 +
| [[:Category:FL3|FL3]]<br/><small>(flavones)</small>
 +
| [[:Category:FL4|FL4]]<br/><small>(dihydroflavonols)</small>
 +
| [[:Category:FL5|FL5]]<br/><small>(flavonols)</small>
 +
| [[:Category:FL6|FL6]]<br/><small>(flavans)</small>
 +
| [[:Category:FL7|FL7]]<br/><small>(anthocyanidins)</small>
 +
| [[:Category:FLI|FLI]]<br/><small>(isoflavonoids)</small>
 +
| [[:Category:FLN|FLN]]<br/><small>(neoflavonoids)</small>
 +
| Total
 +
|-
 +
! #data
 +
| {{#var:FL1Num}} || {{#var:FL2Num}} || {{#var:FL3Num}} || {{#var:FL4Num}} || {{#var:FL5Num}} || {{#var:FL6Num}} || {{#var:FL7Num}} || {{#var:FLINum}} || {{#var:FLNNum}} || {{#var:NumberOfMolecules}}
 +
|}
 
{{#graph:pie|size=350x200;title=Registered Molecules;legend=0.05x0.2;label=;
 
{{#graph:pie|size=350x200;title=Registered Molecules;legend=0.05x0.2;label=;
−
FL1={{#countTitle:FL1|}};
+
FL1={{#var:FL1Num}};
−
FL2={{#countTitle:FL2|}};
+
FL2={{#var:FL2Num}};
−
FL3={{#countTitle:FL3|}};
+
FL3={{#var:FL3Num}};
−
FL4={{#countTitle:FL4|}};
+
FL4={{#var:FL4Num}};
−
FL5={{#countTitle:FL5|}};
+
FL5={{#var:FL5Num}};
−
FL6={{#countTitle:FL6|}};
+
FL6={{#var:FL6Num}};
−
FL7={{#countTitle:FL7|}};
+
FL7={{#var:FL7Num}};
−
FLI={{#countTitle:FLI|}};
+
FLI={{#var:FLINum}};
−
FLN={{#countTitle:FLN|}}; }}
+
FLN={{#var:FLNNum}}}; }}
 
{{#graph:pie|size=350x200;title=Metabolite-Species Relations;legend=0.05x0.2;label=;
 
{{#graph:pie|size=350x200;title=Metabolite-Species Relations;legend=0.05x0.2;label=;
 
FL1={{#countLine:&&FL1|Reference}};
 
FL1={{#countLine:&&FL1|Reference}};
Line 494: Line 260:
 
---->
 
---->
  
−
==Flavonoid content in food 食品中の量==
+
=={{Bilingual|食品含有量|Flavonoid content in food}}==
−
<center>
+
<small>For details, please visit [[Doc:Food/Flavonoid|this page]].</small>
−
{| style="wikitable;" border="1" cellpadding="2" cellspacing="1" margin: 1em 1em 1em 1em"
+
{{Doc:Food/Flavonoid/Summary}}
−
|+ still under construction
+
−
|-
+
−
! style="width:15%" | Category
+
−
! style="width:15%" | <B>Flavonol</B>
+
−
! style="width:15%" | <B>Flavone</B>
+
−
! style="width:15%" | <B>Flavan</B>
+
−
! style="width:15%" | <B>Flavanone</B>
+
−
|-
+
−
| Names
+
−
| <small>quercetin, kampferol, myricetin, isorhamnetin</small>
+
−
| <small>apigenin, luteolin</small>
+
−
| <small>catechin, epicatechin</small>
+
−
|-
+
−
| broccoli ブロッコリ
+
−
|align=center| &Delta; || ||
+
−
|-
+
−
| celery セロリ ||
+
−
|align=center| &Delta;&Delta; ||
+
−
|-
+
−
| fava そら豆 || ||
+
−
|align=center| &Delta;&Delta;
+
−
|-
+
−
| hot pepper とうがらし ||
+
−
|align=center| &Delta;&Delta; ||
+
−
|-
+
−
| onion たまねぎ
+
−
|align=center| &Delta;&Delta; (&Delta;) || ||
+
−
|-
+
−
| parsley パセリ ||
+
−
|align=center| &Delta;&Delta;&Delta; ||
+
−
|-
+
−
| peppermint ペパーミント ||
+
−
|align=center| &Delta;&Delta; || 
+
−
|-
+
−
| spinach ほうれん草 ||
+
−
|align=center| &Delta; ||
+
−
|-
+
−
| thyme タイム ||
+
−
|align=center| &Delta;&Delta;&Delta; ||
+
−
|-
+
−
| watercress クレソン ||
+
−
|align=center| &Delta; ||
+
−
|-
+
−
| dill, fennel ディル, フェンネル ||
+
−
|align=center| &Delta;&Delta;&Delta; ||
+
−
|}
+
−
</center>
+
−
&Delta; 5 to <10 mg/100 g;
+
−
&Delta;&Delta; 10 to <50 mg/100 g;
+
−
&Delta;&Delta;&Delta; 50< mg/100 g
+
−
 
+
−
{{Twocolumn|
+
−
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==
+
=={{Bilingual|ID番号の設計|Design of Flavonoid ID numbers}}==
 
<center>
 
<center>
 
12-DIGIT
 
12-DIGIT
Line 589: Line 295:
  
  
−
===For Users of Flavonoid Viewer===
+
==={{Bilingual|フラボノイドビューワ利用者の方へ|For Users of Flavonoid Viewer}}===
 
{{Twocolumn|
 
{{Twocolumn|
 
The flavonoid IDs used in this site is the same as those in Flavonoid Viewer in [http://metabolome.jp/ metabolome.jp] except for the following FL7 category.
 
The flavonoid IDs used in this site is the same as those in Flavonoid Viewer in [http://metabolome.jp/ metabolome.jp] except for the following FL7 category.

Latest revision as of 11:10, 19 January 2017

Flavonoid Database

Contents

Flavonoid Top Molecule Index Author Index Journals Structure Search Food New Input

[edit] Class Overview

The word "flavonoid" comes from its Latin origin flavus (yellow), meaning yellow-ish. It comes from its history as yellow natural dye (quercetin and kaempferol are the most widespread flavone dyes. See flavone).

In chemistry terms, 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).

Figure 1: The Backbone of Flavonoid Structure

Flavonoid is utilized in many industrial processes from pigments to food additives. Well known names include anthocyanin, catechin, flavan, and isoflavone.

Table 1. Flavonoid Classification
1st Class
FL1: Anthochlor
(Aurone and Chalcone)

Fl1.png
safflower yellow

FL2: Flavanone

Fl2.png
white skin of orange

FL3: Flavone

Fl3.png
herbs like parsley, yellow dye

FL4: Dihydroflavonol

Fl4.png
antioxidant in grapes

FL5: Flavonol

Fl5.png
vegetables such as onion

FL6: Flavan
(Leucoanthocyanidin)

Fl6.png
tea, cocoa

FL7: Anthocyani(di)n

Fl7.png
purple vegetables/fruits

FLI: Isoflavonoid

Fli.png
beans

FLN: Neoflavonoid

Fln.png

[edit] Biosynthesis

[edit] Bioactivity

[edit] 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


[edit] 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


[edit] 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)


[edit] 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

Retrieved from "http://metabolomics.jp/mediawiki/index.php?title=Category:FL&oldid=315233"
Personal tools
Namespaces

Variants
Actions
Navigation
metabolites
Toolbox