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Ononin

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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).
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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.

Natural sources

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

Pharmacokinetics

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

Pharmacodynamics

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

References

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  1. ^ You-Ping Zhu (28 May 1998). Chinese Materia Medica: Chemistry, Pharmacology and Applications. CRC Press. 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. S2CID 3443736.
  3. ^ Stanley F. Osman; William F. Fett (1983). "Isoflavone glucoside stress metabolites of soybean leaves". Phytochemistry. 2 (9): 1921–1923. Bibcode:1983PChem..22.1921O. 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. Bibcode:1985PChem..24..339N. 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". Yao Xue Xue Bao (in Chinese). 49 (8): 1162–1168. PMID 25322559.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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. S2CID 3443736.
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