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Ampelopsin

From Wikipedia, the free encyclopedia
For other uses, seeAmpelopsin (compound).
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 mass320.253 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

Ampelopsin, also known asdihydromyricetin andDHM, when used as an herbal medicine, is aflavanonol, a type of flavonoid. It is extracted from the Japanese raisin tree and found inAmpelopsis speciesjaponica,megalophylla, andgrossedentata;Cercidiphyllum japonicum;Hovenia dulcis;Rhododendron cinnabarinum; somePinus species; and someCedrus species,[1] as well as inSalix sachalinensis.[2]

Hovenia dulcis has been used in traditionalJapanese,Chinese, andKorean medicines to treat fever, parasitic infection, as a laxative, and a treatment of liver diseases, and as ahangover 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

[edit]

Research suggests that ampelopsin protects againstdoxorubicin-inducedcardiotoxicity by inhibitingNLRP3 inflammasome activation via stimulation of theSIRT1 pathway.[4] In a study of 60 patients withnon-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 treatalcohol 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

[edit]

Ampelopsin has been claimed to possess various health, wellness, andcosmetic 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

[edit]
  1. ^Zhou, Jiaju; Xie, Guirong; Yan, Xinjian (2011-02-21).Encyclopedia of Traditional Chinese Medicines – Molecular Structures, Pharmacological Activities, Natural Sources and Applications: Vol. 1: Isolated Compounds A-C. Springer Science & Business Media. p. 123.ISBN 978-3-642-16735-5.
  2. ^Tahara S (June 2007)."A journey of twenty-five years through the ecological biochemistry of flavonoids".Biosci Biotechnol Biochem.71 (6):1387–404.doi:10.1271/bbb.70028.PMID 17587669.S2CID 35670587.
  3. ^abcHyun TK, Eom SH, Yu CY, Roitsch T (July 2010)."Hovenia dulcis--an Asian traditional herb".Planta Med.76 (10):943–9.doi:10.1055/s-0030-1249776.PMID 20379955.
  4. ^Christidi E, Brunham LR (April 2021)."Regulated cell death pathways in doxorubicin-induced cardiotoxicity".Cell Death Dis.12 (4) 339.doi:10.1038/s41419-021-03614-x.PMC 8017015.PMID 33795647.
  5. ^Chen S, Zhao X, Wan J, Ran L, Qin Y, Wang X, Gao Y, Shu F, Zhang Y, Liu P, Zhang Q, Zhu J, Mi M (September 2015). "Dihydromyricetin improves glucose and lipid metabolism and exerts anti-inflammatory effects in nonalcoholic fatty liver disease: A randomized controlled trial".Pharmacol Res.99:74–81.doi:10.1016/j.phrs.2015.05.009.PMID 26032587.
  6. ^Shen Y, Lindemeyer AK, Gonzalez C, Shao XM, Spigelman I, Olsen RW, Liang J (January 2012)."Dihydromyricetin as a novel anti-alcohol intoxication medication".J Neurosci.32 (1):390–401.doi:10.1523/JNEUROSCI.4639-11.2012.PMC 3292407.PMID 22219299.
  7. ^Li H, Li Q, Liu Z, Yang K, Chen Z, Cheng Q, Wu L (2017)."The Versatile Effects of Dihydromyricetin in Health".Evid Based Complement Alternat Med.2017 1053617.doi:10.1155/2017/1053617.PMC 5602609.PMID 28947908.
  8. ^Skotnicová, A.; Boubínová, G.; Boštíková, Z.; Dušková, Š; Šulc, M.; Kutinová-Canová, N.; Mráz, J.; Hodek, P. (2020-12-31)."Does dihydromyricetin impact on alcohol metabolism".Physiological Research.69 (Suppl 4):S573 –S581.doi:10.33549/physiolres.934606.ISSN 1802-9973.PMC 8603706.PMID 33656905.
  9. ^EP patent 2356980A2 
Flavanonols and theirglycosides
3-Hydroxyflavanones:
O-methylated flavanonols
dihydroflavonol 3-O-glycosides
Glycosides
Acetylated glycosides
Alcohols
Barbiturates
Benzodiazepines
Carbamates
Flavonoids
Imidazoles
Kava constituents
Monoureides
Neuroactive steroids
Nonbenzodiazepines
Phenols
Piperidinediones
Pyrazolopyridines
Quinazolinones
Volatiles/gases
Others/unsorted
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