Dihydromyricetin

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Structural formula
Ampelopsin.svg
(+) - dihydromyricetin
General
Surname Dihydromyricetin
other names
  • Ampelopsin
  • Ampeloptin
  • (2 R , 3 R ) -3,5,7-trihydroxy-2- (3,4,5-trihydroxyphenyl) -2,3-dihydrochromen-4-one
Molecular formula C 15 H 12 O 8
Brief description

white needle-shaped crystals

External identifiers / databases
CAS number 27200-12-0
PubChem 161557
ChemSpider 16735660
Wikidata Q422305
properties
Molar mass 320.25 g mol −1
Physical state

firmly

Melting point

245-246 ° C

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dihydromyricetin (DHM), also called ampelopsin , is a flavanonol from the group of flavonoids .

Occurrence

For example, dihydromyricetin is found in the Japanese raisin tree

Dihydromyricetin is found as a secondary plant substance in the Japanese raisin tree ( Hovenia dulcis ), in plants from the genus Ampelopsis , for example in A. meliaefolia , A. japonica , A. megalophylla , A. cantoniensis (= A. grossedentata ), in the coastal Pine ( Pinus contoria ), found in Erythrophleum africanum , in Rhododendron cinnabarinum , and in the Japanese cake tree ( Cercidiphyllum japonicum ).

pharmacology

Dihydromyricetin binds to the GABA A receptor . Alcohol , for example, also binds to this nerve cell receptor . In the animal model, the color rat , it could be shown that alcoholized animals, which had previously been given a dose of 1 mg / kg body weight DHM, were fasted again significantly faster. In further tests, properties that could potentially promote alcohol withdrawal could be determined. Rats, to which any amount of alcohol is available, consume increasing amounts of alcohol over time; a typical sign of addictive behavior. In a test series, DHM was added to the alcohol in the animals after seven weeks, whereupon the alcohol consumption was significantly reduced. The level reached was that of the test animals to which DHM was administered with alcohol from the start.

With the amounts of active ingredient used, no toxicological effects caused by the DHM could be detected in the test animals. Only at 100 times the dose used in the experiments did the rats show slight orientation disorders, which are also caused, for example, by benzodiazepines , which also bind to the GABA A receptor.

A liver-protective effect of DHM is assumed based on various studies on mice. Extracts of the Japanese raisin tree have been approved by the Korea Food & Drug Administration since 2008 for the regeneration of the liver of patients with alcohol abuse . The effect has been known for over 500 years.

further reading

Individual evidence

  1. ↑ a b c d e f g J. Zhou, G. Xie, X. Yan: Encyclopedia of Traditional Chinese Medicines. Verlag Springer, 2011, ISBN 3-642-16734-9 , p. 123. Restricted preview in the Google book search
  2. ↑ a b R. Hänsel, J. Klaffenbach: Optically active dihydromyricetin from Erythrophleum africanum. Volume 294, Number 3, 1961, pp. 158-172, doi : 10.1002 / ardp.19612940306
  3. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. ↑ R. Hegnauer: Chemotaxonomy of plants. Verlag Birkhäuser, 1973, ISBN 3-764-30667-X , p. 639. Restricted preview in the Google book search
  5. ↑ JW Rowe, JH Scroggins: Benzene Extractives of Lodgepole Pine Bark. Isolation of New Diterpenes. In: J Org Chem. Volume 29, Number 6, 1964, pp. 1554-1562. doi : 10.1021 / jo01029a068
  6. ↑ a b Y. Shen, AK Lindemeyer et al .: Dihydromyricetin as a novel anti-alcohol intoxication medication. In: The Journal of neuroscience. Volume 32, number 1, January 2012, pp. 390-401, doi : 10.1523 / JNEUROSCI.4639-11.2012 . PMID 22219299 .
  7. ↑ K. Hase, M. Ohsugi and a .: Hepatoprotective effect of Hovenia dulcis THUNB. on experimental liver injuries induced by carbon tetrachloride or D-galactosamine / lipopolysaccharide. In: Biological and Pharmaceutical Bulletin . Volume 20, Number 4, April 1997, pp. 381-385, PMID 9145214 .
  8. ↑ HL Fang, HY Lin u. a .: Treatment of chronic liver injuries in mice by oral administration of ethanolic extract of the fruit of Hovenia dulcis. In: The American journal of Chinese medicine. Volume 35, Number 4, 2007, pp. 693-703, PMID 17708635 .
  9. ↑ T. Murakami, M. Miyakoshi et al. a .: Hepatoprotective activity of tocha, the stems and leaves of Ampelopsis grossedentata, and ampelopsin. In: BioFactors. Volume 21, Numbers 1-4, 2004, pp. 175-178, PMID 15630194 .
  10. ^ D. Mitchell: Chinese Herbal Hangover Remedy May Fight Alcoholism. In: EmaxHealth. Retrieved January 9, 2012.

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