Ononin

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 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:7775 ;
ChEMBL	ChEMBL465980 ;
ChemSpider	391135 ;
KEGG	C10509 ;
PubChem CID	442813;
UNII	Z0Z637970U ;
CompTox Dashboard (EPA)	DTXSID70964089 ;
	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 Key: MGJLSBDCWOSMHL-MIUGBVLSSA-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). verify (what is ?) 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.

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

^ You-Ping Zhu (28 May 1998). Chinese Materia Medica: Chemistry, Pharmacology and Applications. CRC Press. p. 622. ISBN 9057022850.
^ 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.
^ 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.
^ 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.
^ 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)
^ 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.

[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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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
CompTox Dashboard (EPA)	DTXSID70964089
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