Ononin

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • 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
  • 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
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 checkY☒N ?)
Close

Natural sources

Ononin is a major isoflavone [2] found in a number of plants and herbs like soybean,[3] Astragalus root, 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

Related Articles

Wikiwand AI