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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 effective ingredient in supplements and other tonics, 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 DHM protects against DOX-induced cardiotoxicity by inhibitingNLRP3 inflammasome activation via stimulation of theSIRT1 pathway.[4]

In a trial of 60 patients with "nonalcoholic fatty liver disease," dihydromyricetin improved glucose and lipid metabolism and yielded potentially beneficial anti-inflammatory effects.[5]

A study of rats demonstrated pharmacological properties of DHM which suggest it would be a therapeutic candidate to treatalcohol use disorders.[6]

Dihydromyricetin shows poorbioavailability which limits its potential medicinal applications.[7]

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

Applications

[edit]

Ampelopsin is a versatile compound with a range of applications in health, wellness, andcosmetics, including:

  • Anti-Alcohol Intoxication: DHM is widely used in hangover remedies due to its ability to accelerate alcohol breakdown in the liver and mitigate alcohol-induced damage.[8][3]
  • Liver Protection: It helps in protecting the liver fromtoxins and promoting liver health.[9]
  • Antioxidant and Anti-Inflammatory: DHM has strongantioxidant and anti-inflammatory properties, contributing to its potential in preventing and treating chronic diseases.[10]
  • Cosmetic Applications: DHM is used in skincare products for its ability to protect skin from UV-induced damage and aging.[12]

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. ^"Dihydromyricetin".Stanford Chemicals. RetrievedJuly 7, 2024.
  9. ^Chen, Jingnan; Wang, Xitong (2021)."Molecular mechanisms and therapeutic implications of dihydromyricetin in liver disease".Biomedicine & Pharmacotherapy.142.doi:10.1016/j.biopha.2021.111927.PMID 34339914.
  10. ^Wen, Chaoyu; Zhang, Fan (2023)."Dihydromyricetin alleviates intestinal inflammation by changing intestinal microbial metabolites and inhibiting the expression of the MyD88/NF-κB signaling pathway".Animal Research and One Health.1 (2):219–232.doi:10.1002/aro2.21.
  11. ^Zhang, S; Fan, L (2022)."Dihydromyricetin ameliorates osteogenic differentiation of human aortic valve interstitial cells by targeting c-KIT/interleukin-6 signaling pathway".Frontiers in Pharmacology.13.doi:10.3389/fphar.2022.932092.PMC 9393384.PMID 36003494.
  12. ^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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