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{{other uses|Ampelopsin (compound)}}
{{Other uses|Ampelopsin (compound)}}
{{chembox
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| ImageFile = Ampelopsin.svg
| ImageFile = Ampelopsin.svg
| ImageSize = 250px
| ImageSize = 250px
| IUPACName = (2''R'',3''R'')-3,5,7-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-4-one
| IUPACName = (2''R'',3''R'')-3,3′,4′,5,5′,7-Hexahydroxyflavan-4-one
| SystematicName = (2''R'',3''R'')-3,5,7-Trihydroxy-2-(3,4,5-trihydroxy)-2,3-dihydro-4''H''-1-benzopyran-4-one
| OtherNames = Dihydromyricetin, Ampeloptin,(+)-Ampelopsin,(+)-Dihydromyricetin
| OtherNames = Dihydromyricetin, Ampeloptin,(+)-Ampelopsin,(+)-Dihydromyricetin
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 27200-12-0
| CASNo = 27200-12-0
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KD8QND6427
| PubChem = 161557
| PubChem = 161557
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
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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 found in the ''[[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/?id=PMsXJnUYTFkC&printsec=frontcover&dq=isbn:9783642167355#v=onepage&q&f=false|publisher = Springer Science & Business Media|date = 2011-02-21|isbn = 978-3-642-16735-5|first = Jiaju|last = Zhou|first2 = Guirong|last2 = Xie|first3 = Xinjian|last3 = Yan}}</ref> as well as in ''[[Salix sachalinensis]]''.<ref>{{cite journal|title = A Journey of Twenty-Five Years through the Ecological Biochemistry of Flavonoids|journal = Bioscience, Biotechnology, and Biochemistry|date = June 23, 2007|issn = 0916-8451|pmid = 17587669|pages = 1387–1404|volume = 71|issue = 6|doi = 10.1271/bbb.70028|first = Satoshi|last = Tahara}}</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|last1=Hyun|first1=Tae|last2=Eom|first2=Seung|last3=Yu|first3=Chang|last4=Roitsch|first4=Thomas|title=Hovenia dulcis– An Asian Traditional Herb|journal=Planta Medica|volume=76|issue=10|year=2010|pages=943–949|issn=0032-0943|doi=10.1055/s-0030-1249776|pmid=20379955|doi-access=free}}</ref> Methods have been developed to extract ampelopsin from it at large scales, 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 />
<big>'''Scientific peer-reviewed research'''</big>


== Research ==
⚫
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|last1=Chen|first1=Shihui|last2=Zhao|first2=Xiaolan|last3=Wan|first3=Jing|last4=Ran|first4=Li|last5=Qin|first5=Yu|last6=Wang|first6=Xiaofang|last7=Gao|first7=Yanxiang|last8=Shu|first8=Furong|last9=Zhang|first9=Yong|last10=Liu|first10=Peng|last11=Zhang|first11=Qianyong|last12=Zhu|first12=Jundong|last13=Mi|first13=Mantian|title=Dihydromyricetin improves glucose and lipid metabolism and exerts anti-inflammatory effects in nonalcoholic fatty liver disease: A randomized controlled trial|journal=Pharmacological Research|volume=99|year=2015|pages=74–81|issn=1043-6618|doi=10.1016/j.phrs.2015.05.009|pmid=26032587}}</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>
In a study wherein the subjects were rats, researchers demonstrated "pharmacological properties of dihydromyricetin consistent with those expected to underlie successful medical treatment of [[alcohol use disorders]]; therefore dihydromyricetin is a therapeutic candidate."<ref>{{Cite journal
| author = Yi Shen, A. Kerstin Lindemeyer, Claudia Gonzalez, Xuesi M. Shao, Igor Spigelman, Richard W. Olsen & Jing Liang
| title = Dihydromyricetin as a novel anti-alcohol intoxication medication
| journal = [[The Journal of Neuroscience]]
| volume = 32
| issue = 1
| pages = 390–401
| year = 2012
| doi = 10.1523/JNEUROSCI.4639-11.2012
| pmid = 22219299
| pmc = 3292407
}}</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>
"Structurally, due to the highly hydrophilic character, dihydromyricetin shows poor '''[[bioavailability]]''' and significantly limits its potential medicinal applications."<ref>{{Cite journal|last=Li|first=Hongliang|last2=Li|first2=Qisheng|last3=Liu|first3=Zhaowen|last4=Yang|first4=Kai|last5=Chen|first5=Zhixi|last6=Cheng|first6=Qilai|last7=Wu|first7=Longhuo|date=2017|title=The Versatile Effects of Dihydromyricetin in Health|url=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5602609/|journal=Evidence-based Complementary and Alternative Medicine : eCAM|volume=2017|doi=10.1155/2017/1053617|issn=1741-427X|pmc=5602609|pmid=28947908}}</ref> "In pharmacology, '''bioavailability''' [...] is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation."<ref>{{Cite web|url=https://en.m.wikipedia.org/wiki/Bioavailability|title=Bioavailability - Wikipedia|website=en.m.wikipedia.org|language=en|access-date=2020-04-28}}</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>
⚫
As they pertain to dihydromyricetin, 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.


== References ==
== References ==
{{Reflist|2}}<br />{{Flavanonol}}
{{Reflist}}
{{Flavanonol}}
{{GABAAR PAMs}}
{{GABAAR PAMs}}


Latest revision as of 05:59, 4 October 2023

For other uses, see Ampelopsin (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 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.
source: https://en.wikipedia.org/w/index.php?title=Ampelopsin&diff=1178522706&oldid=953634007

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