Category:FL7

Revision as of 16:23, 7 January 2010 (view source) Adm (Talk | contribs) ← Older edit		Revision as of 17:07, 7 January 2010 (view source) Adm (Talk | contribs) (→‎Biosynthesis) Newer edit →
Line 114:		Line 114:
	| F3'5'H is absent.		| F3'5'H is absent.
	|}		|}
		+
		+
		+	===Structure===
		+
		+	{{Twocolumn
		+	|
		+	Most anthocyanins in autumn leaves are comparatively simple and 3-O-glycosilated (glucoside, galactoside, rhamnoside, gentiobiosid and rutinoside) and/or acylated (p-coumaric, caffeic, ferulic, gallic, acetyl, malonic, malic etc.). Those in storage organs often show complicated structures (see [[Species:Ipomoea|Ipomoea]] and [[Species:Dioscorea|Dioscorea]]).
		+	|
		+	紅葉に含まれる多くのアントシアニンは多くが単純な構造を持ち3位に糖（グルコース、ガラクトース、ラムノース、ゲンチオビオース、ルチン）、更にアシル化（p-クマル酸、ケイ皮酸、フェルラ酸、没食子酸、酢酸、マロン酸、リンゴ酸）をうけます。芋のような貯蔵器官に含まれるものは複雑な構造が多くなります（ [[Species:Ipomoea|サツマイモ属]]や[[Species:Dioscorea|ヤマノイモ属]]を参照のこと）。
		+	}}
	==Database statistics データベース統計==<!--- see also FL1--->		==Database statistics データベース統計==<!--- see also FL1--->

---

Revision as of 17:07, 7 January 2010

Anthocyanidin, Anthocyanin

Flavonoid Top

Molecule Index

Author Index

Journals

Structure Search

Food

New Input

Upper classes : FL Flavonoid

2nd Class
FL7A	Anthocyanin	FL7D	3-Deoxyanthocyanin

Contents 1 Overview 1.1 Target of fruit- and flower-color engineering 2 Biosynthesis 2.1 Structure 3 Database statistics データベース統計 4 Major Plant Families

Overview

Distribution

Anthocyanin is almost ubiquitous, whereas 3-Deoxyanthocyanin (luteolinidin and apigeninidin) is found only in some lower plants (moss and fern^[1][2][3]) and in sorghum (Sorghum bicolor ^[4]), gloxinia (Sinningia cardinalis) and many species in Gesneriaceae^[5].
The nine known families without anthocyanin are Aizoaceae, Amaranthaceae, Basellaceae, Cactaceae, Chenopodiaceae, Didiereaceae, Nyctaginaceae, Phytolaccaceae, Portulacaceae (all in the order Caryophylalles). These families synthesize the betalain instead of anthocyanin.^[6]

Word origin

The Greek word origin of anthocyanin is "flower" ἀνθός (anthos) and "blue" κυανός (kyanos). It was first used by Marquart to describe water-soluble pigments in red, blue, and purple from flowers ^[7]. Nowadays, such water-soluble pigments from flowers and fruits are called anthocyan. The flavonoid backbone without sugar (shown below) is called anthocyanidin (it is called aglycon because it is devoid of glyco moiety), and structure with sugars is called anthocyanin. Except for carotenoid (yellow) or indigo (deep blue), most pigments of plant origin are anthocyanins.

1. ↑ Bendz G, Martensson O, Terenlus L: Moss pigments I. The anthocyanins of Bryum cryophilum O. Mart. Acta Chem Scand 1962 16:1183-1190
2. ↑ Bendz G, Martensson O: Moss pigments II. The anthocyanins of Bryum rutilans Brid. and Bryum weigelii Spreng. Acta Chem Scand 1963 17:266
3. ↑ Comparative biochemistry of the flavonoids-II. 3-Desoxyanthocyanins and their systematic distribution in ferns and gesnerads. Phytochemistry 1966 5:589-600
4. ↑ Nip WK, Burns EE: Pigment characterization in grain Sorghum. Cereal Chem 1969 46:490-495 also in 1971 48:74-80
5. ↑ Harborne JB: Comparative biochemistry of the flavonoids-II. 3-Desoxyanthocyanins and their systematic distribution in ferns and gesnerads. Phytochemistry 5:589-600
6. ↑ Piattelli M, Minale L: Pigments of centrospermae-II. Distribution of betacyanins. Phytochemistry 1964 3:547-557
7. ↑ Marquart LC. "Die Farben der Bluethen. Eine chemisch-physiol." Abhandlung, Bonn, 1835 (Cited by Onslow MW. "The Anthocyanin Pigments of Plants," Cambridge University Press, 1925).

Target of fruit- and flower-color engineering

Anthocyanin contains 3 aromatic rings, and glycosylation at the 3-OH position is necessary for stabilizing the aromatic ring. The general color of anchocyanin is red in acidic environment and purple/blue in alkali. The colors are, however, dependent on many other factors such as additional modifications and metal ions as is suggested by multi-color flowers such as pansy (yellow, orange, purple, violet, deep blue). (BY Masanori Arita)

References

• Kroon J. et al. Plant J. 1994 Jan;5(1):69-80 PMID 8130799
• Boss PK. et al. Plant Mol Biol. 1996 Nov;32(3):565-9 PMID 8980508
• Fukuchi-Mizutani M. et al. Plant Physiol. 2003 Jul;132(3):1652-63 PMID 12857844 (research paper on Blue Rose)

Biosynthesis

The six common anthocyanidins are the product of three different branches.

Biosynthesis (continued from the chart in Flavonoid)
(red or orange)		(blue or magenta)		(blue or purple)
pelargonidin	hydroxylation	cyanidin	hydroxylation	delphinidin
		peonidin		petunidin
indicates methylation by anthocyanin O-methyltransferase (AOMT)
				malvidin

All three classes exist in most angio- and gymnosperm orders, and hydroxylating enzymes (F3'H and F3'5'H) show high sequence homology throughout orders. However, genetic changes cause genus-specific inactivation of these pathways.

Genus (Family)	Inactivation	Cause
Arabidopsis (Brassicaceae) Petunia (Solanaceae) Cymbidium (Orchidaceae)	pelargonidin	DFR does not metabolize dihydrokaempferol.
Chrysanthemum (Asteraceae) Dianthus (Caryophyllaceae) Ipomoea (Convolvulaceae)	delphinidin	F3'5'H is absent.

Structure

Most anthocyanins in autumn leaves are comparatively simple and 3-O-glycosilated (glucoside, galactoside, rhamnoside, gentiobiosid and rutinoside) and/or acylated (p-coumaric, caffeic, ferulic, gallic, acetyl, malonic, malic etc.). Those in storage organs often show complicated structures (see Ipomoea and Dioscorea).

Database statistics データベース統計

Major Plant Families

The number in each family is counted as the number of genera (not species) listed in our registered references. Each reference record is accessible by clicking the link in compound pages. The taxonomy follows the APG-II classification. For details (or if the figure is broken), visit this page. 各科のカウントは種名でなく文献に記載された属名の数です。文献は代謝物ページのリンクからたどれ、分類はAPG-IIです。左の図が表示されない場合はここをクリックしてください。