ampelopsin
{{Other uses|Ampelopsin (compound)}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443388481
| ImageFile = Ampelopsin.svg
| ImageSize = 250px
| IUPACName = (2R,3R)-3,3′,4′,5,5′,7-Hexahydroxyflavan-4-one
| SystematicName = (2R,3R)-3,5,7-Trihydroxy-2-(3,4,5-trihydroxy)-2,3-dihydro-4H-1-benzopyran-4-one
| OtherNames = Dihydromyricetin, Ampeloptin,(+)-Ampelopsin,(+)-Dihydromyricetin
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735660
| 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
| InChIKey = KJXSIXMJHKAJOD-CABCVRREBP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = KJXSIXMJHKAJOD-CABCVRRESA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 27200-12-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KD8QND6427
| PubChem = 161557
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28429
| SMILES = Oc1cc(cc(O)c1O)[C@@H]3Oc2cc(O)cc(O)c2C(=O)[C@H]3O
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|Section2={{Chembox Properties
| C=15 | H=12 | O=8
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Ampelopsin, also known as dihydromyricetin and DHM, when used as an effective ingredient in supplements and other tonics, 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,{{cite book |title=Encyclopedia of Traditional Chinese Medicines – Molecular Structures, Pharmacological Activities, Natural Sources and Applications: Vol. 1: Isolated Compounds A-C |url=https://books.google.com/books?id=PMsXJnUYTFkC |publisher=Springer Science & Business Media |date=2011-02-21 |isbn=978-3-642-16735-5 |first1=Jiaju |last1=Zhou |first2=Guirong |last2=Xie |first3=Xinjian |last3=Yan |page=123}} as well as in Salix sachalinensis.{{cite journal |vauthors=Tahara S |title=A journey of twenty-five years through the ecological biochemistry of flavonoids |journal=Biosci Biotechnol Biochem |volume=71 |issue=6 |pages=1387–404 |date=June 2007 |pmid=17587669 |doi=10.1271/bbb.70028 |s2cid=35670587|doi-access=free }}
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.{{cite journal |vauthors=Hyun TK, Eom SH, Yu CY, Roitsch T |title=Hovenia dulcis--an Asian traditional herb |journal=Planta Med |volume=76 |issue=10 |pages=943–9 |date=July 2010 |pmid=20379955 |doi=10.1055/s-0030-1249776 |doi-access=free}} 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.
Research
Research suggests that DHM protects against DOX-induced cardiotoxicity by inhibiting NLRP3 inflammasome activation via stimulation of the SIRT1 pathway.{{cite journal |vauthors=Christidi E, Brunham LR |title=Regulated cell death pathways in doxorubicin-induced cardiotoxicity |journal=Cell Death Dis |volume=12 |issue=4 |pages=339 |date=April 2021 |pmid=33795647 |pmc=8017015 |doi=10.1038/s41419-021-03614-x }}
In a trial of 60 patients with "nonalcoholic fatty liver disease," dihydromyricetin improved glucose and lipid metabolism and yielded potentially beneficial anti-inflammatory effects.{{cite journal |vauthors=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 |title=Dihydromyricetin improves glucose and lipid metabolism and exerts anti-inflammatory effects in nonalcoholic fatty liver disease: A randomized controlled trial |journal=Pharmacol Res |volume=99 |issue= |pages=74–81 |date=September 2015 |pmid=26032587 |doi=10.1016/j.phrs.2015.05.009 |url=}}
A study of rats demonstrated pharmacological properties of DHM which suggest it would be a therapeutic candidate to treat alcohol use disorders.{{cite journal |vauthors=Shen Y, Lindemeyer AK, Gonzalez C, Shao XM, Spigelman I, Olsen RW, Liang J |title=Dihydromyricetin as a novel anti-alcohol intoxication medication |journal=J Neurosci |volume=32 |issue=1 |pages=390–401 |date=January 2012 |pmid=22219299 |pmc=3292407 |doi=10.1523/JNEUROSCI.4639-11.2012 }}
Dihydromyricetin shows poor bioavailability which limits its potential medicinal applications.{{cite journal |vauthors=Li H, Li Q, Liu Z, Yang K, Chen Z, Cheng Q, Wu L |title=The Versatile Effects of Dihydromyricetin in Health |journal=Evid Based Complement Alternat Med |volume=2017 |issue= |pages=1053617 |date=2017 |pmid=28947908 |pmc=5602609 |doi=10.1155/2017/1053617 |doi-access=free }}
Additional research is required before claims of human efficacy and application, necessary dosage, and solutions to poor bioavailability, are met with scientific validation.
Applications
Ampelopsin is a versatile compound with a range of applications in health, wellness, and cosmetics, 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.{{cite web |url=https://www.stanfordchem.com/dihydromyricetin.html |title=Dihydromyricetin |website=Stanford Chemicals |access-date=July 7, 2024}}
- Liver Protection: It helps in protecting the liver from toxins and promoting liver health.{{cite journal |last1=Chen |first1=Jingnan |last2=Wang |first2=Xitong |date=2021 |title=Molecular mechanisms and therapeutic implications of dihydromyricetin in liver disease |journal=Biomedicine & Pharmacotherapy |volume=142 |doi=10.1016/j.biopha.2021.111927|pmid=34339914 |doi-access=free }}
- Antioxidant and Anti-Inflammatory: DHM has strong antioxidant and anti-inflammatory properties, contributing to its potential in preventing and treating chronic diseases.{{cite journal |last1=Wen |first1=Chaoyu |last2=Zhang |first2=Fan |year=2023 |title=Dihydromyricetin alleviates intestinal inflammation by changing intestinal microbial metabolites and inhibiting the expression of the MyD88/NF-κB signaling pathway |journal= Animal Research and One Health|volume=1 |issue=2 |pages=219–232 |doi=10.1002/aro2.21|doi-access=free }}
- Cardiovascular Health: Research indicates that DHM may lower blood pressure and reduce cholesterol levels, benefiting heart health.{{cite journal |last1=Zhang |first1=S |last2=Fan |first2=L |year=2022 |title=Dihydromyricetin ameliorates osteogenic differentiation of human aortic valve interstitial cells by targeting c-KIT/interleukin-6 signaling pathway |journal= Frontiers in Pharmacology|volume=13 |doi=10.3389/fphar.2022.932092|doi-access=free |pmid=36003494 |pmc=9393384 }}
- Cosmetic Applications: DHM is used in skincare products for its ability to protect skin from UV-induced damage and aging.{{cite patent |status=patent |country=EP |number=2356980A2}}
References
{{Reflist}}
{{Flavanonol}}
{{GABAAR PAMs}}