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Ononin

From Wikipedia, the free encyclopedia
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 mass430.409 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Ononin is anisoflavone glycoside, the 7-O-β-D-glucopyranoside offormononetin,[1] which in turn is the 4'-O-methyl (4'-methoxy) derivative of the parent isoflavonedaidzein.

Natural sources

[edit]

Ononin is a major isoflavone[2] found in a number of plants and herbs likesoybean,[3]Astragalus root, andGlycyrrhiza uralensis.[4]

Pharmacokinetics

[edit]

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

Pharmacodynamics

[edit]

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

References

[edit]
  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.
Isoflavones and theirglycosides
Isoflavones
O-methylated isoflavones
Glycosides
Prenylated isoflavones
Pyranoisoflavones
Derivatives
Synthetic
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