Ampelopsin

Chemical compound From Wikipedia, the free encyclopedia

Ampelopsin, also known as dihydromyricetin and DHM, when used as an herbal medicine, is a flavanonol, a type of flavonoid. It is extracted from the Japanese raisin tree and found in Ampelopsis species japonica, megalophylla, and grossedentata; Cercidiphyllum japonicum; Hovenia dulcis; Rhododendron cinnabarinum; some Pinus species; and some Cedrus species,[1] as well as in Salix sachalinensis.[2]

Quick facts Names, Identifiers ...
Ampelopsin
Names
IUPAC name
(2R,3R)-3,3′,4′,5,5′,7-Hexahydroxyflavan-4-one
Systematic IUPAC name
(2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxy)-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Dihydromyricetin, Ampeloptin,(+)-Ampelopsin,(+)-Dihydromyricetin
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m1/s1 checkY
    Key: KJXSIXMJHKAJOD-CABCVRRESA-N checkY
  • InChI=1/C15H12O8/c16-6-3-7(17)11-10(4-6)23-15(14(22)13(11)21)5-1-8(18)12(20)9(19)2-5/h1-4,14-20,22H/t14-,15+/m1/s1
    Key: KJXSIXMJHKAJOD-CABCVRREBP
  • Oc1cc(cc(O)c1O)[C@@H]3Oc2cc(O)cc(O)c2C(=O)[C@H]3O
Properties
C15H12O8
Molar mass 320.253 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Hovenia dulcis has been used in traditional Japanese, Chinese, and Korean medicines to treat fever, parasitic infection, as a laxative, and a treatment of liver diseases, and as a hangover treatment.[3] Methods have been developed to extract ampelopsin on a larger scale, and laboratory research has been conducted with the compound to see if it might be useful as a drug in any of the conditions for which the parent plant has been traditionally used.[3]

Research

Research suggests that ampelopsin protects against doxorubicin-induced cardiotoxicity by inhibiting NLRP3 inflammasome activation via stimulation of the SIRT1 pathway.[4] In a study of 60 patients with non-alcoholic fatty liver disease, ampelopsin improved glucose and lipid metabolism and yielded potentially beneficial anti-inflammatory effects.[5] A study of rats demonstrated pharmacological properties of ampelopsin which suggest it would be a therapeutic candidate to treat alcohol use disorders.[6]

Additional research is required before claims of human efficacy and application, necessary dosage, and solutions to poor bioavailability, are met with scientific validation.[7]

Purported benefits

Ampelopsin has been claimed to possess various health, wellness, and cosmetic benefits, including:

  • Anti-alcohol intoxication: ampelopsin is widely used in hangover remedies due to its claimed ability to accelerate alcohol breakdown in the liver and mitigate alcohol-induced damage.[3] However, a pharmacokinetic study found no effect of DHM on alcohol metabolism.[8]
  • Cosmetic applications: ampelopsin is used in skincare products for its purported ability to protect skin from UV-induced damage and aging.[9]

References

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