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{{otheruses|Ampelopsin (compounds)}}
{{Other uses|Ampelopsin (compound)}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 443388481
| verifiedrevid = 443388481
| name = Ampelopsin
| ImageFile = Ampelopsin.svg
⚫
| ImageSize = 250px
| ImageFile = Ampelopsin.svg
| IUPACName = (2''R'',3''R'')-3,3′,4′,5,5′,7-Hexahydroxyflavan-4-one
⚫
| ImageSize = 250px
| IUPACName = (2''R'',3''R'')-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-2,3-dihydrochromen-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<br>Ampeloptin<br>(+)-Ampelopsin<br>(+)-Dihydromyricetin
| OtherNames = Dihydromyricetin, Ampeloptin,(+)-Ampelopsin,(+)-Dihydromyricetin
| Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16735660
| 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
| 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
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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}}
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| PubChem = 161557
| UNII = KD8QND6427
⚫
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫
| PubChem = 161557
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| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28429
| ChEBI = 28429
| SMILES = Oc1cc(cc(O)c1O)[C@@H]3Oc2cc(O)cc(O)c2C(=O)[C@H]3O
| SMILES = Oc1cc(cc(O)c1O)[C@@H]3Oc2cc(O)cc(O)c2C(=O)[C@H]3O
}}
}}
| Section2= {{Chembox Properties
|Section2={{Chembox Properties
| C=15|H=12|O=8
| C=15 | H=12 | O=8
| Appearance =
| ExactMass = 320.053217
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition =
| AutoignitionPt =
}}
}}
}}
}}
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'''Ampelopsin''', also known as '''dihydromyricetin''', 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>Jiaju Zhou, Guirong Xie, Xinjian Yan Encyclopedia of Traditional Chinese Medicines - Molecular Structures, Pharmacological Activities, Natural Sources and Applications: Vol. 1: Isolated Compounds A-C. Springer Science & Business Media, 2011 ISBN 9783642167355</ref> as well as in ''[[Salix sachalinensis]]''.<ref>Tahara S. A journey of twenty-five years through the ecological biochemistry of flavonoids. Biosci Biotechnol Biochem. 2007 Jun;71(6):1387-404. PMID 17587669</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>Hyun TK et al. Hovenia dulcis--an Asian traditional herb. Planta Med. 2010 Jul;76(10):943-9. PMID 20379955</ref> Methods have been developed to extract ampelopsin 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 />
⚫
==References==

{{reflist}}
== 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>

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>

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

⚫
== References ==
{{Reflist}}


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


[[Category:Flavanonols]]
[[Category:Flavanonols]]
[[Category:Pyrogallols]]
[[Category:Pyrogallols]]
[[Category:Resorcinols]]
[[Category:Resorcinols]]
[[Category:GABAA receptor positive allosteric modulators]]

{{Natural-phenol-stub}}

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=635481208

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