ononin

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 414762729

| Name = Ononin

| Reference =

| ImageFile = Ononin.svg

| IUPACName = 7-(β-D-Glucopyranosyloxy)-4′-methoxyisoflavone

| SystematicName = 3-(4-Methoxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one

| OtherNames = Formononetin glucoside
Formononetin-7-glucoside
Formononetin 7-O-glucoside

|Section1={{Chembox Identifiers

| Abbreviations =

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 486-62-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z0Z637970U

| EINECS =

| PubChem = 442813

| SMILES = COC1=CC=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O

| RTECS =

| MeSHName =

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 7775

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 465980

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 391135

| SMILES2 = COc1ccc(cc1)c2coc3cc(ccc3c2=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O

| 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

| InChIKey = MGJLSBDCWOSMHL-MIUGBVLSBD

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = MGJLSBDCWOSMHL-MIUGBVLSSA-N

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C10509

}}

|Section2={{Chembox Properties

| C=22 | H=22 | O=9

| Appearance =

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|Section7={{Chembox Hazards

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| FlashPt =

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}}

Ononin is an isoflavone glycoside, the 7-O-β-D-glucopyranoside of formononetin,{{Cite book | title = Chinese Materia Medica: Chemistry, Pharmacology and Applications | author = You-Ping Zhu | date = 28 May 1998 | page = 622 | publisher = CRC Press | isbn = 9057022850}} which in turn is the 4'-O-methyl (4'-methoxy) derivative of the parent isoflavone daidzein.

Natural sources

Ononin is a major isoflavone {{cite journal | doi = 10.1016/j.molimm.2017.01.007 | title = Anti-inflammatory effects of ononin on lipopolysaccharide-stimulated RAW 264.7 cells | journal = Molecular Immunology | volume = 83 | pages = 46–51 | year = 2017 | last1 = Dong | first1 = Lin | last2 = Yin | first2 = Lei | last3 = Zhang | first3 = Yuanbin | last4 = Fu | first4 = Xueyan | last5 = Lu | first5 = Jincai | pmid = 28095349 | s2cid = 3443736 }} found in a number of plants and herbs like soybean,{{cite journal | journal = Phytochemistry | volume = 2 | issue = 9 | date = 1983 | pages = 1921–1923 | title = Isoflavone glucoside stress metabolites of soybean leaves |author1=Stanley F. Osman |author2=William F. Fett | doi = 10.1016/0031-9422(83)80013-2 | bibcode = 1983PChem..22.1921O }} Astragalus root, and Glycyrrhiza uralensis.{{cite journal | journal = Phytochemistry | volume = 24 | issue = 2 | date = 1985 | pages = 339–341 | title = Flavonoid glycosides of the roots of Glycyrrhiza uralensis |author1=Tsutomu Nakanishi |author2=Akira Inada |author3=Kazuko Kambayashia |author4=Kaisuke Yonedaa | doi = 10.1016/S0031-9422(00)83548-7| bibcode = 1985PChem..24..339N }}

Pharmacokinetics

Intestinal bacterial metabolic pathways may include demethylation and deglycosylation.{{cite journal | pmid = 25322559 | journal = Yao Xue Xue Bao | date = 2014 | volume = 49 | issue = 8 | pages = 1162–1168 | title = The interaction between ononin and human intestinal bacteria | language = Chinese | author = Zhang W, Jiang S, Qian DW, Shang EX, Guan HL, Ren H, Zhu ZH, Duan JA}} 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.{{cite journal | doi = 10.1016/j.molimm.2017.01.007| title = Anti-inflammatory effects of ononin on lipopolysaccharide-stimulated RAW 264.7 cells| journal = Molecular Immunology| volume = 83| pages = 46–51| year = 2017| last1 = Dong| first1 = Lin| last2 = Yin| first2 = Lei| last3 = Zhang| first3 = Yuanbin| last4 = Fu| first4 = Xueyan| last5 = Lu| first5 = Jincai| pmid = 28095349| s2cid = 3443736}}

References