Taxifolin

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Taxifolin
200px
Names
IUPAC name
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Other names
Dihydroquercetin
Taxifoliol
Distylin
Catechin hydrate
(+)-Taxifolin
trans-Dihydroquercetin
(+)-Dihydroquercetin
Identifiers
480-18-2 N
ChEBI CHEBI:17948 N
ChEMBL ChEMBL66 N
ChemSpider 388626 N
EC Number 207-543-4
Jmol 3D model Interactive image
KEGG C01617 N
PubChem 439533
Properties
C15H12O7
Molar mass 304.25 g·mol−1
Appearance Brown powder
UV-vismax) 290, 327 nm (methanol)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Taxifolin is a flavanonol, a type of flavonoid.

Natural occurrences

It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii,[1] in Cedrus deodara[1] and in the Chinese yew, Taxus chinensis var. mairei.[2]

It is also found in the silymarin extract from the milk thistle seeds.

Taxifolin is present in vinegars aged in cherry wood.[3]

Pharmacology

Taxifolin is not mutagenic and less toxic than the related compound quercetin.[4] It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism.[5] Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.[6] There is also a strong correlation (with a correlation coefficient of 0.93) between the antiproliferative effects of dihydroquercetin (DHQ, Taxifolin) derivatives on murine skin fibroblasts and human breast cancer cells.[7]

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine.[8] Also taxifolin inhibited the cellular melanogenesis as effectively as arbutin, one of the most widely used hypopigmenting agents in cosmetics. However, arbutin acts as quercetin extremely mutagenic, carcinogenic and toxic.[9]

Taxifolin enhanced also the efficacy of conventional antibiotics like levofloxacin and ceftazidime in vitro, which have potential for combinatory therapy of patients infected with methicillin-resistant Staphylococcus aureus (MRSA).[10]

Taxifolin, as well as many other flavonoids, has been found to act as a non-selective antagonist of the opioid receptors, albeit with somewhat weak affinity.[11]

Taxifolin has been found to act as an agonist of the adiponectin receptor 2 (AdipoR2).[12]

Metabolism

The enzyme taxifolin 8-monooxygenase uses taxifolin, NADH, NADPH, H+, and O2 to produce 2,3-dihydrogossypetin, NAD+, NADP+, and H2O.

The enzyme leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, taxifolin, succinate, CO2, and H2O.

Glycosides

Astilbin is the 3-O-rhamnoside of taxifolin. Taxifolin deoxyhexose can be found in açai fruits.[13]

Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa.[14]

(-)-2,3-trans-Dihydroquercetin-3'-O-β-D-glucopyranoside, a taxifolin glucoside has been extracted from the inner bark of Pinus densiflora and can act as an oviposition stimulant in the cerambycid beetle Monochamus alternatus.[15]

(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.[16]

(2R,3R)-Taxifolin-3'-O-β-D-pyranoglucoside has been isolated from the rhizome of Smilax glabra.[17]

Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found in red onions.[18]

(2R,3R)-Taxifolin 3-O-arabinoside and (2S,3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides[19] (star jasmine).

Chemistry

(+)-Leucocyanidin can be synthesized from taxifolin by sodium borohydride reduction.[20]

References

  1. 1.0 1.1 Extractives in bark of different conifer species growing in Pakistan. Willför S, Mumtaz Ali, Karonen M, Reunanen M, Mohammad Arfan and Harlamow R, Holzforschung, 2009, Volume 63, Number 5, pages 551-558, doi:10.1515/HF
  2. Chemistry of Chinese yew, Taxus chinensis var. mairei. Cunfang Li, Changhong Huo , Manli Zhang, Qingwen Shi, Biochemical Systematics and Ecology, Volume 36, Issue 4, April 2008, Pages 266–282, doi:10.1016/j.bse.2007.08.002
  3. Effect of wood on the phenolic profile and sensory properties of wine vinegars during ageing. Ana B. Cerezoa, Wendu Tesfayea, M.E. Soria-Díazb, M. Jesús Torijac, Estíbaliz Mateoc, M. Carmen Garcia-Parrillaa, Ana M. Troncosoa, Journal of Food Composition and Analysis, March 2010, Volume 23, Issue 2, Pages 175–184, doi:10.1016/j.jfca.2009.08.008
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  7. Rogovskiĭ VS, Matiushin AI, Shimanovskiĭ NL; et al. (2010). "Antiproliferative and antioxidant activity of new dihydroquercetin derivatives". Eksperimental'naia i klinicheskaia farmakologiia. 73 (9): 39–42. PMID 21086652. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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  13. Polyphenolic Constituents of Fruit Pulp of Euterpe oleracea Mart. (Açai palm). S. Gallori, A. R. Bilia, M. C. Bergonzi, W. L. R. Barbosa and F. F. Vincieri, Chromatographia, June 2004, Volume 59, Issue 11-12, pages 739-743, doi:10.1365/s10337-004-0305-x
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  15. Sato, Masashi; Islam, Syed Q.; Awata, Shinobu; Yamasaki, Tory (1999). "Flavanonol glucoside and proanthocyanidins: Oviposition stimulants for the cerambycid beetle, Monochamus alternatus" (PDF). Journal of Pesticide Science. 24 (2): 123–9.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  16. Pei YH, Li X, Zhu TR, Wu LJ (1990). "[Studies on the structure of a new flavanonol glucoside of the root-sprouts of Agrimonia pilosa Ledeb]". Yao Xue Xue Bao (in Chinese). 25 (4): 267–70. PMID 2281787. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  17. Yuan JZ, Dou DQ, Chen YJ, et al. (September 2004). "[Studies on dihydroflavonol glycosides from rhizome of Smilax glabra]". Zhongguo Zhong Yao Za Zhi (in Chinese). 29 (9): 867–70. PMID 15575206. <templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  18. Flavonoids from red onion (Allium cepa). Torgils Fossen, Atle T. Pedersen and Øyvind M. Andersen, Phytochemistry, January 1998, Volume 47, Issue 2, Pages 281–285, doi:10.1016/S0031-9422(97)00423-8
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