Taxifolin

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Structural formula
Structural formula
(+) - Taxifolin
General
Surname Taxifolin
other names
  • ( 2R, 3R ) - (+) - taxifolin
  • (2 R , 3 R ) -Dihydroquercetin (DHQ)
  • 3,3 ', 4', 5,7-pentahydroxyflavanone
  • 3,3 ', 4', 5,7-pentahydroxy-2,3-dihydroflavone
  • ( 2R, 3R ) -2- (3,4-dihydroxyphenyl) -2,3-dihydro-3,5,7-trihydroxy-4 H -1-benzopyran-4-one
  • DIHYDROQUERCETINE ( INCI )
Molecular formula C 15 H 12 O 7
Brief description

light yellow solid

External identifiers / databases
CAS number 480-18-2
EC number 207-543-4
ECHA InfoCard 100.006.859
PubChem 439533
ChemSpider 458
DrugBank DB02224
Wikidata Q412191
properties
Molar mass 304.24 g mol −1
Physical state

firmly

density

1.33 g cm −3

Melting point

227 ° C (decomposition)

solubility

bad in water

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Taxifolin is a naturally occurring organic compound that chemically belongs to the flavanonols (compare structure, variety and subgroups of flavonoids ). In its pure state, Taxifolin is a white to light yellow powder.

pharmacology

As for many flavonoids, antioxidant effects on metabolic functions in humans have been demonstrated. Taxifolin has - compared to 2,3- unsaturated quercetin - only about 50% of its antioxidant effect. The presence of a double bond in the vicinity of a hydroxyl group ( enol structure ) and thus a possibility to stabilize energetically unfavorable states seems to be an essential characteristic of antioxidant flavonoids. However, the lack of a double bond on the heterocycle probably means that taxifolin is not mutagenic and hardly toxic compared to quercetin.

At the beginning of the coronavirus crisis in March 2020, a study by the University of Basel identified taxifolin as the only natural substance in a computer-aided screening of 687 million compounds, along with only 11 other active ingredient-like compounds, as a potent inhibitor of the novel coronavirus protease of SARS-CoV-2 .

Based on the results of an in vitro study on colon cancer cells , a modulation of chemopreventive regulating genes by taxifolin was postulated. It was also shown that, among other things Taxifolin in vitro the ovarian cancer cell growth dose-dependently inhibited. There is a strong correlation between the inhibitory effect of taxifolin derivatives on tissue reproduction in mouse skin cell lines and in human breast cancer cells. Results of a study in vitro and animal experiments show that taxifolin can represent a potential new therapeutic agent for the treatment of osteosarcoma (bone cancer).

Findings from a mouse model published in 2010 suggest that taxifolin, when used externally and internally, prevents the production of inflammatory cytokines , reduces skin inflammation and is therefore a possible therapeutic agent against neurodermatitis .

Epidemiological and in vivo studies indicate a positive influence of flavonoids in various cardiovascular diseases . Traditionally, these effects have only been attributed to antioxidant activities. However, in addition to the direct binding of reactive oxygen species (ROS), there are a number of other effects which, in pharmacologically achievable concentrations, can also be responsible for the positive cardiovascular influence. These include, in particular, the inhibition of ROS- forming enzymes, inhibition of platelet function , inhibition of leukocyte activation, and properties that lower blood pressure and expand blood vessels.

Taxifolin inhibits cellular melanogenesis ebensoso effective as arbutin , one of the most widely used agent for hyperpigmentation in cosmetics . In animal experiments on mice, a prevention of the production of inflammatory cytokines and a reduction in skin inflammation were observed after topical treatment with taxifolin .

Taxifolin significantly reduces the production of the blue dye pyocyanin and the enzyme elastase in the widespread hospital germ Pseudomonas aeruginosa . The flavonoid thus also inhibits the virulence of disease-causing bacteria by interfering with their quorum sensing mechanism. Taxifolin also improved the effectiveness of conventional antibiotics such as levofloxacin and ceftazidime against MRSA infections in vitro .

Dihydroquercetin inhibits the production of lipopolysaccharide -induced prostaglandin E . Taxifolin was isolated from Cercidiphyllum japonicum among other substances and showed - similar to minoxidil and procyanidin B-2 - significant activities on mouse hair epithelial cells that stimulate hair growth . Taxifolin has shown similarly strong effects on protein and RNA synthesis in liver cells as with silibinin .

The antimicrobial activity of Taxifolin against Streptococcus sobrinus could be demonstrated in vitro . Stopping these common bacteria from multiplying in the mouth could be a potent means of preventing tooth decay.

Occurrence and extraction

Siberian larch ( Larix sibirica )

Certain parts of the trunks of conifers, especially larch [e.g. B. Siberian larch ( Larix sibirica )], have a relatively high proportion of taxifolin (DHQ). The phenolic ingredients, in connection with plant metabolic reactions, are decisive for the natural durability and resistance of the wood to pests, UV radiation and weather. In the case of larch, the Taxifolin is of decisive importance here. The totality of phenolic ingredients rarely goes beyond 3 to 4%. In the first step in the extraction of Taxifolin, the lower ends of the larch trunk, which is a waste product from wood production, are debarked and chopped up. The following laboratory tests provide information about the proportion of DHQ (dihydroquercetin) in the chips. Using classic extraction processes , Taxifolin is produced with a purity of max. 85 to 88% achieved. Only a subsequent multi-stage liquid chromatography (LC) leads to a degree of purity of almost 100%. This process is necessary in order to remove undesirable impurities such as resins and other substances from the substance obtained.

A glycoside of Taxifolin is the astilbin () (+ - Taxifolin-3-O-α-L-rhamnopyranoside), which in the rhizome of Astilbe Astilbe odontophylla occurs.

Individual evidence

  1. ↑ Entry on DIHYDROQUERCETIN in the CosIng database of the EU Commission, accessed on May 16, 2020.
  2. ↑ a b Data sheet Taxifolin at Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
  3. ^ Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 479 ( limited preview in Google Book search).
  4. ↑ a b David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 452 ( limited preview in Google Book search).
  5. ↑ Russian Pharmacology and Toxicology , 1975, Vol. 38, p. 213.
  6. ↑ a b Entry on Taxifolin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  7. ↑ MB GUPTA, TN BHALLA u. a .: ANTI-INFLAMMATORY ACTIVITY OF TAXIFOLIN. In: The Japanese Journal of Pharmacology. 21, 1971, p. 377, doi : 10.1254 / jjp.21.377 .
  8. ↑ H. Boehm, H. Boeing et al.: Flavonols, flavones and anthocyanins as natural antioxidants in food and their possible role in the prevention of chronic diseases. In: Journal of Nutritional Science. Volume 37, 1998, pp. 147-163. doi : 10.1007 / PL00007376 .
  9. ^ PS Makena, SC Pierce et al. a .: Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP-2 uvrA. In: Environmental and Molecular Mutagenesis . Volume 50, number 6, July 2009, pp. 451-459, doi : 10.1002 / em.20487 . PMID 19326464 .
  10. ^ André Fischer; Manuel Sellner; Santhosh Neranjan; Markus A. Lill; Martin Smieško: Inhibitors for Novel Coronavirus Protease Identified by Virtual Screeningof 687 Million Compounds. University of Basel, 2020. ( online )
  11. ↑ SB Lee, KH Cha et al. a .: The chemopreventive effect of taxifolin is exerted through ARE-dependent gene regulation. In: Biological and Pharmaceutical Bulletin . Volume 30, Number 6, June 2007, pp. 1074-1079, PMID 17541156 .
  12. ↑ H. Luo, BH Jiang et al. a .: Inhibition of cell growth and VEGF expression in ovarian cancer cells by flavonoids. In: Nutrition and Cancer . Volume 60, number 6, 2008, pp. 800-809, doi : 10.1080 / 01635580802100851 . PMID 19005980 .
  13. ↑ VS Rogovski ?, AI Matiushin u. a .: [Antiproliferative and antioxidant activity of new dihydroquercetin derivatives]. In: Eksperimental'naia i klinicheskaia farmakologiia. Volume 73, Number 9, September 2010, pp. 39-42, PMID 21086652 .
  14. ↑ Xin Chen, Na Gu, Chao Xue, Ban-Ruo Li: Plant flavonoid taxifolin inhibits the growth, migration and invasion of human osteosarcoma cells . PMID 29257319 .
  15. ↑ JY Ahn et al .: Effect of taxifolin glycoside on atopic dermatitis-like skin lesions in NC / Nga mice. In: Phytotherapy research. 24 (7), Jul 2010, pp. 1071-1077. PMID 0041431
  16. ↑ P. Mladenka, L. Zatloukalová u. a .: Cardiovascular effects of flavonoids are not caused only by direct antioxidant activity. In: Free Radical Biology and Medicine . Volume 49, number 6, September 2010, pp. 963-975, doi : 10.1016 / j.freeradbiomed.2010.06.010 . PMID 20542108 . (Review).
  17. ↑ SM An, HJ Kim et al. a .: Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels. In: Phytotherapy Research . Volume 22, Number 9, September 2008, pp. 1200-1207, doi : 10.1002 / ptr.2435 . PMID 18729255 .
  18. ↑ JY Ahn, SE Choi u. a .: Effect of taxifolin glycoside on atopic dermatitis-like skin lesions in NC / Nga mice. In: Phytotherapy Research. Volume 24, Number 7, July 2010, pp. 1071-1077, doi : 10.1002 / ptr.3084 . PMID 20041431 .
  19. ↑ OM Vandeputte, M. Kiendrebeogo u. a .: The flavanone naringenin reduces the production of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa PAO1. In: Microbiology. Volume 157, July 2011, pp. 2120-2132, doi : 10.1099 / mic.0.049338-0 . PMID 21546585 .
  20. ↑ J. An, GY Zuo et al. a .: Antibacterial and synergy of a flavanonol rhamnoside with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA). In: Phytomedicine . Volume 18, number 11, August 2011, pp. 990-993, doi : 10.1016 / j.phymed.2011.02.013 . PMID 21466953 .
  21. ↑ Y.Woo, SYShin, J. Hyun et al. a .: Flavanones inhibit the clonogenicity of HCT116 colo ( l ) [r] ectal cancer cells. In: International journal of molecular medicine. 2012 Mar; 29 (3): 403-8., PMID 22160193 .
  22. ↑ K.Towatari et al. a .: Polyphenols from the heartwood of Cercidiphyllum japonicum and their effects on proliferation of mouse hair epithelial cells. In: Planta Medica . 2002 Nov; 68 (11): 995-8., PMID 12451489 .
  23. ↑ J. Sonnenbichler et al. a .: Biochemistry and pharmacology of Silibinin. (PDF; 801 kB) In: Phytopharmaka II, Research and Clinical Application , p. 133 (127–138).
  24. ↑ Harlinda Kuspradini, Tohru Mitsunaga, Hideo Ohashi: Antimicrobial activity against Streptococcus sobrinus and glucosyltransferase inhibitory activity of taxifolin and some flavanonol rhamnosides from kempas (Koompassia malaccensis) extracts. In: Journal of Wood Science - J WOOD SCI. vol. 55, no. 4, pp. 308-313, 2009. doi : 10.1007 / s10086-009-1026-4
  25. ↑ Rupert Wimmer, University of Natural Resources and Life Sciences, Vienna: When larch wood sees red! . www.holzkurier.com, January 5, 2009.