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'''Ampelopsin''', also known as '''dihydromyricetin''' and '''DHM''', when purported 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,<ref name="EncTCM">{{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}}</ref> as well as in ''[[Salix sachalinensis]]''.<ref name="pmid17587669">{{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 }}</ref>


'''Ampelopsin''', also known as '''dihydromyricetin''' and '''DHM''', when purported 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,<ref name="EncTCM">{{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}}</ref> as well as in ''[[Salix sachalinensis]]''.<ref name="pmid17587669">{{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 }}</ref>
''[[Hovenia dulcis]]'' has been used in traditional [[Kampo|Japanese]], [[Traditional chinese medicine|Chinese]], and [[Traditional Korean medicine|Korean]] medicines to treat fever, parasitic infection, as a laxative, and a treatment of liver diseases, and as a [[hangover]] treatment.<ref name=Hyun>{{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}}</ref> 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.<ref name=Hyun />

''[[Hovenia dulcis]]'' has been used in traditional [[Kampo|Japanese]], [[Traditional chinese medicine|Chinese]], and [[Traditional Korean medicine|Korean]] medicines to treat fever, parasitic infection, as a laxative, and a treatment of liver diseases, and as a [[hangover]] treatment.<ref name=Hyun>{{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}}</ref> 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.<ref name=Hyun />


== Research ==
== Research ==
Research suggests that DHM protects against [[Doxorubicin| DOX-induced cardiotoxicity]] by inhibiting [[NLRP3]] inflammasome activation via stimulation of the [[SIRT1]] pathway.<ref name="pmid33795647">{{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 }}</ref>


In a trial of 60 patients with "[[Non-alcoholic fatty liver disease|nonalcoholic fatty liver disease]]," dihydromyricetin improved glucose and lipid metabolism and yielded potentially beneficial anti-inflammatory effects.<ref name="ChenZhao2015">{{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=}}</ref>
Research suggests that DHM protects against [[Doxorubicin| DOX-induced cardiotoxicity]] by inhibiting [[NLRP3]] inflammasome activation via stimulation of the [[SIRT1]] pathway.<ref name="pmid33795647">{{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 }}</ref>


In a trial of 60 patients with "[[Non-alcoholic fatty liver disease|nonalcoholic fatty liver disease]]," dihydromyricetin improved glucose and lipid metabolism and yielded potentially beneficial anti-inflammatory effects.<ref name="ChenZhao2015">{{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 = }}</ref>
A study of rats demonstrated pharmacological properties of DHM which suggest it would be a therapeutic candidate to treat [[alcohol use disorders]].<ref name="pmid22219299">{{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 }}</ref>


A study of rats demonstrated pharmacological properties of DHM which suggest it would be a therapeutic candidate to treat [[alcohol use disorders]].<ref name="pmid22219299">{{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 }}</ref>
Dihydromyricetin shows poor [[bioavailability]] which limits its potential medicinal applications.<ref name="pmid28947908">{{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 }}</ref>

Dihydromyricetin shows poor [[bioavailability]] which limits its potential medicinal applications.<ref name="pmid28947908">{{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 }}</ref>


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

{{Flavanonol}}
{{Flavanonol}}
{{GABAAR PAMs}}
{{GABAAR PAMs}}

Latest revision as of 05:59, 4 October 2023

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).
☒N verify (what is checkY☒N ?)

Ampelopsin, also known as dihydromyricetin and DHM, when purported 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,[1] as well as in Salix sachalinensis.[2]

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[edit]

Research suggests that DHM protects against DOX-induced cardiotoxicity by inhibiting NLRP3 inflammasome activation via stimulation of the SIRT1 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 treat alcohol use disorders.[6]

Dihydromyricetin shows poor bioavailability 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.

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. ^ a b 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.

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