Category:FLI

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Isoflavonoid


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Upper classes : FL Flavonoid

Contents

イソフラボノイドの概要

2nd Class
FLIA Isoflavone
Flia.png 		FLIB Isoflavanone
Flib.png 		FLIC Isoflavan
Flic.png 		FLID Pterocarpane
Flid.png
FLIE Coumestan
Flie.png 		FLIF Rotenoid
Flif.png 		FLIG Coumaranochromone
Flig.png 		FLIH 3-Arylcoumarin
Flih.png
FLII 2-Arylbenzofuran
Flii.png 		FLIJ alpha-Methoxynbenzoin
Flij.png

The discovery of isoflavonoid was in 1842, when Reinsch and Hlasiwetz obtained ononin from the roots of spiny restharrow (Ononis spinosa L.)[1]. Its structure was later determined by Baker et al. as Formononetin 7-O-glucoside (1933). Since then, most isoflavonoids have been found in Fabaceae (bean family).
First isoflavonoid found in non-bean family was iridin from the rhizomes of Iris florentina (Iridaceae)[2]. The first structural identification was Prunetin from Prunus species in 1910 by Finnemore. Major isoflavonoids in iris are isoflavones and their O-glycosides. In iris, isoflavonoids are produced only in the rhizomes except for a trace of coumaranochromones in leaves [3].

イソフラボノイドの発見は1842年まで遡り、ReinschとHlasiwetzが マメ科ハリモクシュにononinを見出しました。 その構造をFormononetin 7-O-glucosideと同定したのは Baker et al. たちです(1933)。以降、イソフラボノイドのほとんどはマメ科に見出されてきました。
マメ科以外からはじめて見つかったイソフラボノイドは、アヤメ(Iris florentina, Iridaceae)の根茎から抽出されたイリジンです。ただし初めて精製、構造が同定されたのは1910年のプルネチン (Prunus属) です(Finnemore)。アヤメにおける主なイソフラボノイドはイソフラボンとその配糖体です。アヤメでは葉に微量あるクマラノクロモンを除く全イソフラボノイドが根茎にあります。

  1. ↑ Reinsch H, Repert. Pharm. 26:12-31, 1842; Reinsch H, Repert. Pharm. 28:18-25, 1842; Hlasiwetz H, J. Prakt. Chem. 65:419-450, 1855; Hlasiwetz H, Sitzungsber. Kais. Akad. Wiss. Wien, Math.-Naturwiss. Kl. 15:142-168, 1855
  2. ↑ de Laire G and Tiemann F, Chem. Ber., 26:2010, 1893
  3. ↑ Iwashita T, Ootani S: Flavonoids of the genus Iris: structures, distribution and function (review). Ann. Tsukuba Bot. Gard. 17:147-183 (in Japanese)

代表例

daidzein
FLIA1ANS0002.png 		genistein
FLIAAANS0001.png 		coumestrol
FLIE1ANS0001.png 		Medicarpin
FLID1ANS0001.png

Daidzin is its glycosylated form in soy beans. Daidzein (aglycon) is contained in fermented beans. Medicarpin is the major phytoalexin in alfalfa (Medicago sativa) and clover (Trifolium spp.), synthesized by bacterial infection[1].

大豆に含まれるのは、ダイジンというダイゼインの配糖体。豆を醗酵させるとアグリコンであるダイゼインになる。 メディカルパンはアルファルファ(Medicago sativa)やクローバー(Trifolium spp.)が微生物の感染に対抗して生産する防御物質として知られる。

  1. ↑ Guo L, Dixon RA, Paiva NL (1994) Conversion of vestitone to medicarpin in alfalfa (Medicago sativa L.) is catalyzed by two independent enzymes. Identification, purification, and characterization of vestitone reductase and 7,2'-dihydroxy-4'-methoxyisoflavanol dehydratase. J Biol Chem 269:22372-22378

食品含有量

Isoflavone Contents (mg / 100g wet weight) [1]
food daizein genistein glycitein total isoflavone
大豆（全粒）乾 153 201 40 394
大豆（全粒）ゆで 27 95 1 123
えだまめ　生 3 6 0 10
えだまめ　ゆで 5 7 1 12
豆腐（木綿、絹、ゆし等） 12-28 20-40 2 39-63
納豆、生揚げ、がんもどき 13-37 27-82 1-4 42-126
味噌（甘味噌、淡色辛、赤色辛） 21-23 29-38 2-4 53-60
緑豆もやし、アルファルファ、えんどう、いんげん、そらまめ 0 0 0 0
  1. ↑ 荒井綜一 他編 「機能性食品の辞典」朝倉書店 p.341

生合成

This pathway is said to exist as an enzyme complex at ER membrane. [1]

この経路はER膜に局在する酵素複合体を形成すると言われています。

liquiritigenin
FL2F1ANS0001.png
Arrow00r35.png
IFS 		daidzein
FLIA1ANS0002.png
Arrow00r35.png
IOMT 		formononetin
FLIA1ANS0001.png
Arrow00r35.png
I2'H + IFR 		vestitone
FLIB1LNS0002.png
Arrow00r35.png
VR + DMID 		medicarpin
FLID1ANS0001.png


Structural Genes (continued from Flavonoid)
Abbrev. Name Origin Information
IFS isoflavone synthase cytochrome P450 oxygenase family [2][3]

[4]

  • CYP93C subfamily in Fabaceae[5]
  • IgIFS1 in German iris (Iridaceae) shows low similarity (< 35%) with other P450[6]
Use both liquiritigenin and naringenin as substrates to produce genistein and daidzein, respectively.
IOMT isoflavone O-methyltransferase
I2'H isoflavone 2'-hydroxylase cytochrome P450 oxygenase family[7]
IFR isoflavone reductase
VR vestitone reductase
DMID 7,2'-dihydroxy,4'-methyxyisoflavanol dehydratase
  1. ↑ Hrazdina G: Compartmentation in aromatic metabolism. In HA Stafford, RK Ibrahim, eds, Recent Advances in Phytochemistry. Plenum Press, New York, 1992 pp 1–23
  2. ↑ Akashi T, Aoki T, Ayabe S: Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol 1999 121:821-828
  3. ↑ Steele CL, Gijzen M, Qutob D, Dixon RA: Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean. Arch Biochem Biophys 1999 367: 146–150
  4. ↑ Jung W, Yu O, Sze-Mei CL, O’Keefe DP, Odell J, Fader G, McGonigle B: Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nat Biotechnol 2000 18: 208–213
  5. ↑ Ayabe S, Akashi T (2006) Phytochem Rev 5(2-3), 271-282
  6. ↑ Akashi T (2011) Proceedings of Biosynthetic Machinary (in Japanese)
  7. ↑ Akashi T, Aoki T, Ayabe S: CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 29-hydroxylase. 1998 Biochem Biophys Res Comm 251: 67–70

データベース統計

主な植物科

 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。

Subcategories

This category has the following 10 subcategories, out of 10 total.

F

  • [×] FLIA‎ (empty)
  • [×] FLIB‎ (empty)
  • [×] FLIC‎ (empty)
  • [×] FLID‎ (empty)

F cont.

  • [×] FLIE‎ (empty)
  • [×] FLIF‎ (empty)
  • [×] FLIG‎ (empty)
  • [×] FLIH‎ (empty)

F cont.

  • [×] FLII‎ (empty)
  • [×] FLIJ‎ (empty)
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