Ononin

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Ononin
Ononin.svg
Names
IUPAC name
3-(4-Methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Other names
Formononetin glucoside
Formononetin-7-glucoside
Formononetin 7-O-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
Properties
C22H22O9
Molar mass 430.41 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 ☑Y☒N ?)
Infobox references

Ononin is an isoflavone glycoside, the 7-0-beta-D-glucopyranoside of formononetin,[1] which in turn is the 4'-O-methoxy derivative of the parent isoflavone daidzein.

Natural sources[edit]

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

Pharmacokinetics[edit]

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

Pharmacodynamics[edit]

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

References[edit]

  1. ^ "Chinese Materia Medica: Chemistry, Pharmacology and Applications" By You-Ping Zhu, page 622, ISBN 9057022850
  2. ^ 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. ^ PMID 25322559
  6. ^ PMID 28095349