Ampelopsin

Last updated
Ampelopsin
Ampelopsin.svg
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
PubChem CID
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 Yes check.svgY
    Key: KJXSIXMJHKAJOD-CABCVRRESA-N Yes check.svgY
  • 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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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]

Contents

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:

References

  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. 1 2 3 Hyun 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. ↑ EPpatent 2356980A2
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