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 ;
	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. 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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

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Original source: https://en.wikipedia.org/wiki/Ononin. Read more

[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.

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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

Ononin

Topic: Chemistry

Contents

Natural sources

Pharmacokinetics

Pharmacodynamics

References

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