Ononin

Ononin
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
CAS Number	486-62-4 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:7775 ;
ChEMBL	ChEMBL465980 ;
ChemSpider	391135 ;
KEGG	C10509 ;
PubChem CID	442813;
	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	430.41 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 7-0-beta-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

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[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

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

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
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
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	430.41 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 ^YN ?)
Infobox references