Taxifolin

Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclass flavanonols in the flavonoids, which in turn is a class of polyphenols. It is extracted from plants such as Siberian larch and milk thistle. [2]

Taxifolin
Names
IUPAC name
(2R,3R)-3,3′,4′,5,7-Pentahydroxyflavan-4-one
Systematic IUPAC name
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names
Dihydroquercetin
Taxifoliol
Distylin
(+)-Taxifolin
trans-Dihydroquercetin
(+)-Dihydroquercetin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.859
EC Number
  • 207-543-4
KEGG
UNII
  • InChI=1S/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1 ☒N
    Key: CXQWRCVTCMQVQX-LSDHHAIUSA-N ☒N
  • InChI=1/C15H12O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,14-19,21H/t14-,15+/m0/s1
    Key: CXQWRCVTCMQVQX-LSDHHAIUBE
  • OC1=C(C([C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)=O)C3=CC(O)=C1
Properties
C15H12O7
Molar mass 304.254 g·mol−1
Appearance Brown powder
Melting point 237 °C (459 °F; 510 K)[1]
UV-vis (λmax) 290, 327 nm (methanol)
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 ?)
Infobox references

Stereocenters

Taxifolin has two stereocenters on the C-ring, as opposed to quercetin which has none.[3] For example, (+)-taxifolin has (2R,3R)-configuration, making it 1 out of 4 stereoisomers that comprise 2 pairs of enantiomers.[4]

Natural occurrences

Taxifolin is found in non-glutinous rice boiled with adzuki bean (adzuki-meshi).[5]

It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii,[6] in Cedrus deodara[6] and in the Chinese yew, Taxus chinensis var. mairei.[7]

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

Taxifolin is present in vinegars aged in cherry wood.[8]

Taxifolin, and flavonoids in general, can be found in many beverages and products. Specifically, taxifolin is found in plant-based foods like fruit, vegetables, wine, tea, and cocoa.[9]

Pharmacology

Taxifolin is not mutagenic and less toxic than the related compound quercetin.[10] It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism.[11] Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.[12] However, in this same study, taxifolin was the least effective flavonoid in the inhibition of VEGF expression.[13] There is also a strong correlation (with a correlation coefficient of 0.93) between the antiproliferative effects of taxifolin derivatives on murine skin fibroblasts and human breast cancer cells.[14]

Taxifolin has shown to have anti-proliferative effects on many types of cancer cells by inhibiting cancer cell lipogenesis. By inhibiting the fatty acid synthase in cancer cells, taxifolin is able to prevent the growth and spread of cancer cells.[15]

Taxifolin also stops the effects of overexpression of P-glycoprotein, which prevents the development of chemoresistance. Taxifolin does this via inhibition of rhodamine 123 and doxorubicin.[16]

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine.[17] 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.[18]

Taxifolin also enhances 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).[19]

Taxifolin can act as an anti-flammant because of its ability to inhibit the synthesis of cyclooxygenase by blocking prostaglandin synthesis. [20] Indeed, the taxifolin-mediated inhibition of the E2 prostaglandin synthesis (by PLA2 phospholipase) was shown to prevent beta-amyloid-induced impairment of synapsis genesis and related memory deficits, which take part in the pathogenesis of neurodegenerative disorders like Alzheimer's disease.[21] Other observed benefits comprise the reduction of beta-amyloid accumulation in the brain vessels, restoration of vascular integrity and memory improvement in cerebral amyloid angiopathy, a condition often linked to alzheimer's.[22] Cognitive performance has even been raised in young healthy adults by taxifolin administration.[23]

Like other flavonoids, taxifolin is able to function as an antifungal agent by blocking multiple pathways that promote the growth and proliferation of fungi. [20]

Taxifolin has also been found to reduce inhibitor of intestinal mobility especially when antagonized by verapamil.[20]

Taxifolin has also been shown to be anti-hyperlipidemic by maintaining the normal lipid profile of the liver and keeping lipid excretion at normal levels. Taxifolin prevents hyperlipidemia by reducing the esterification of cellular cholesterol, phospholipid, and triacylglycerol synthesis.[16]

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.[24] Taxifolin shows promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders [25]

Taxifolin has been found to act as an agonist of the adiponectin receptor 2 (AdipoR2).[26]

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, alpha-ketoglutarate, 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.[27]

Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa.[28]

(-)-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.[29]

(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.[30]

(2R,3R)-Taxifolin-3'-O-β-D-pyranoglucoside has been isolated from the rhizome of Smilax glabra.[31]

Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found in red onions.[32]

(2R,3R)-Taxifolin 3-O-arabinoside and (2S,3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides[33] (star jasmine).

Derived natural compounds

References
  1. Graham, H. M.; Kurth, E. F. (1949). "Constituents of Extractives from Douglas Fir". Industrial and Engineering Chemistry. 41 (2): 409–414. doi:10.1021/ie50470a035.
  2. Title = Global Taxifolin Market Size was USD 167.90 Million in 2022| URL = https://www.reportprime.com/taxifolin-r195 | Date = 14 August 2023 | Website = https://www.reportprime.com/
  3. "Quercetin". pubchem.ncbi.nlm.nih.gov.
  4. "(+)-taxifolin (CHEBI:17948)". www.ebi.ac.uk.
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  6. Willför S, Mumtaz A, Karonen M, Reunanen M, Mohammad A, Harlamow R (August 2009). "Extractives in bark of different conifer species growing in Pakistan". Holzforschung. 63 (5): 551–558. doi:10.1515/HF.2009.095. S2CID 97003177.
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  8. Cerezoa, Ana B.; Tesfayea, Wendu; Soria-Díazb, M.E.; Torijac, M. Jesús; Mateoc, Estíbaliz; Garcia-Parrillaa, M. Carmen; Troncosoa, Ana M. (2010). "Effect of wood on the phenolic profile and sensory properties of wine vinegars during ageing". Journal of Food Composition and Analysis. 23 (2): 175–184. doi:10.1016/j.jfca.2009.08.008.
  9. Brusselmans, K.; Vrolix, R.; Verhoeven, G.; Swinnen, J. (2005). "Induction of Cancer Cell Apoptosis by Flavonoids Is Associated with Their Ability to Inhibit Fatty Acid Synthase Activity". Journal of Biological Chemistry. 280 (7): 5636–5645. doi:10.1074/jbc.m408177200. PMID 15533929.
  10. Makena, Patrudu S.; Pierce, Samuel C.; Chung, King-Thom; Sinclair, Scott E. (2009). "Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP-2 uvrA". Environmental and Molecular Mutagenesis. 50 (6): 451–9. doi:10.1002/em.20487. PMID 19326464. S2CID 25826873.
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  16. Das, A.; Baidya, R.; Chakraborty, T.; Samanta, A. K.; Roy, S. Pharmacological basis and new insights of taxifolin: A comprehensive review. Biomedicine & Pharmacotherapy 2021, 142, 17.
  17. Tarahovsky, Y. S.; Selezneva, I. I.; Vasilieva, N. A.; Egorochkin, M. A.; Kim, Yu. A. (2007). "Acceleration of fibril formation and thermal stabilization of collagen fibrils in the presence of taxifolin (dihydroquercetin)". Bulletin of Experimental Biology and Medicine. 144 (6): 791–4. doi:10.1007/s10517-007-0433-z. PMID 18856203. S2CID 22328651.
  18. An, Sang Mi; Kim, Hyo Jung; Kim, Jung-Eun; Boo, Yong Chool (2008). "Flavonoids, taxifolin and luteolin attenuate cellular melanogenesis despite increasing tyrosinase protein levels". Phytotherapy Research. 22 (9): 1200–7. doi:10.1002/ptr.2435. PMID 18729255. S2CID 29105755.
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  22. Saito, 2017
  23. Shinozaki, 2023
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  25. Sunil, Christudas; Xu, Baojun (2019). "An insight into the health-promoting effects of taxifolin (dihydroquercetin)". Phytochemistry. 166: 112066. doi:10.1016/J.PHYTOCHEM.2019.112066. PMID 31325613. S2CID 198131999.
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  29. Sato, Masashi; Islam, Syed Q.; Awata, Shinobu; Yamasaki, Tory (1999). "Flavanonol glucoside and proanthocyanidins: Oviposition stimulants for the cerambycid beetle, Monochamus alternatus". Journal of Pesticide Science. 24 (2): 123–9. doi:10.1584/jpestics.24.123.
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  31. 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.
  32. Fossen, Torgils (1998). "Flavonoids from red onion (Allium cepa)". Phytochemistry. 47 (2): 281–285. doi:10.1016/S0031-9422(97)00423-8.
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