Ononin

Names
IUPAC name

7-(β-D-Glucopyranosyloxy)-4′-methoxyisoflavone

Systematic IUPAC name

3-(4-Methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one

Other names

Formononetin glucoside
Formononetin-7-glucoside
Formononetin 7-O-glucoside

Identifiers

CAS Number

* 486-62-4 Y

3D model (JSmol)

* Interactive image
* Interactive image

ChEBI |

* CHEBI:7775 N

ChEMBL |

* ChEMBL465980 N

ChemSpider |

* 391135 N

KEGG |

* C10509 N

PubChem CID

* 442813

UNII |

* Z0Z637970U Y

InChI

* InChI=1S/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1 N

Key: MGJLSBDCWOSMHL-MIUGBVLSSA-N N

* InChI=1/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1

Key: MGJLSBDCWOSMHL-MIUGBVLSBD

SMILES

* COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O

* COc1ccc(cc1)c2coc3cc(ccc3c2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O

Properties

Chemical formula

| C22H22O9
Molar mass | 430.409 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin,[1] which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein.

## Contents

* 1 Natural sources
* 2 Pharmacokinetics
* 3 Pharmacodynamics
* 4 References

## Natural sources

Ononin is a major isoflavone [2] found in a number of plants and herbs like soybean[3] and Glycyrrhiza uralensis.[4]

## Pharmacokinetics

Intestinal bacterial metabolic pathways may include demethylation and deglycosylation.[5] It follows that formation of formononetin and/or daidzein is possible.

## Pharmacodynamics

An in vitro anti-inflammatory effect on lipopolysaccharide (LPS)-induced inflammation has been demonstrated in one study.[6]

## References

1. ↑ You-Ping Zhu (28 May 1998). Chinese Materia Medica: Chemistry, Pharmacology and Applications. p. 622. ISBN 9057022850.
2. ↑ Dong, Lin; Yin, Lei; Zhang, Yuanbin; Fu, Xueyan; Lu, Jincai (2017). "Anti-inflammatory effects of ononin on lipopolysaccharide-stimulated RAW 264.7 cells". Molecular Immunology 83: 46–51. doi:10.1016/j.molimm.2017.01.007. PMID 28095349.
3. ↑ Stanley F. Osman; William F. Fett (1983). "Isoflavone glucoside stress metabolites of soybean leaves". Phytochemistry 2 (9): 1921–1923. doi:10.1016/0031-9422(83)80013-2.
4. ↑ Tsutomu Nakanishi; Akira Inada; Kazuko Kambayashia; Kaisuke Yonedaa (1985). "Flavonoid glycosides of the roots of Glycyrrhiza uralensis". Phytochemistry 24 (2): 339–341. doi:10.1016/S0031-9422(00)83548-7.
5. ↑ Zhang W, Jiang S, Qian DW, Shang EX, Guan HL, Ren H, Zhu ZH, Duan JA (2014). "The interaction between ononin and human intestinal bacteria" (in Chinese). Yao Xue Xue Bao 49 (8): 1162–1168. PMID 25322559.
6. ↑ Dong, Lin; Yin, Lei; Zhang, Yuanbin; Fu, Xueyan; Lu, Jincai (2017). "Anti-inflammatory effects of ononin on lipopolysaccharide-stimulated RAW 264.7 cells". Molecular Immunology 83: 46–51. doi:10.1016/j.molimm.2017.01.007. PMID 28095349.

* v
* t
* e

Isoflavones and their glycosides

Isoflavones|

* Daidzein
* Genistein
* Orobol

O-methylated isoflavones|

* Biochanin A
* Calycosin
* Formononetin
* Glycitein
* Irigenin
* 5-O-methylgenistein
* Pratensein
* Prunetin
* Psi-tectorigenin
* Retusin
* Tectorigenin

Glycosides|

* Daidzin
* Genistin
* Iridin
* Mirificin
* Ononin
* Puerarin
* Sophoricoside
* Tectoridin

Prenylated isoflavones|

* Bidwillol A
* Derrubone
* Luteone
* 7-O-Methylluteone
* Wighteone

Pyranoisoflavones|

* Alpinumisoflavone
* Barbigerone
* Di-O-methylalpinumisoflavone
* 4'-methyl-alpinumisoflavone

Derivatives|

* Anagyroidisoflavone A and B
* Irilone
* Pseudobaptigenin
* Rotenoids

Synthetic|

* Ipriflavone

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