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.

Taxifolin
Names
IUPAC name
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-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
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).
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Infobox references

Stereocenters

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

Natural occurrences

Taxifolin is found in non-glutinous rice boiled with adzuki bean (adzuki-meshi).[4]

It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii,[5] in Cedrus deodara[5] and in the Chinese yew, Taxus chinensis var. mairei.[6]

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

Taxifolin is present in vinegars aged in cherry wood.[7]

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.[8]

Pharmacology

Taxifolin is not mutagenic and less toxic than the related compound quercetin.[9] It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism.[10] Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.[11] However, in this same study, taxifolin was the least effective flavonoid in the inhibition of VEGF expression.[12] 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.[13]

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.[14]

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine.[15] 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.[16]

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).[17]

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.[18] Taxifolin showed promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders [19]

Taxifolin has been found to act as an agonist of the adiponectin receptor 2 (AdipoR2).[20]

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.[21]

Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa.[22]

(-)-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.[23]

(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.[24]

(2R,3R)-Taxifolin-3'-O-β-D-pyranoglucoside has been isolated from the rhizome of Smilax glabra.[25]

Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found in red onions.[26]

(2R,3R)-Taxifolin 3-O-arabinoside and (2S,3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides[27] (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. "Quercetin". pubchem.ncbi.nlm.nih.gov.
  3. "(+)-taxifolin (CHEBI:17948)". www.ebi.ac.uk.
  4. Takahama (2016-10-01). "Antioxidative flavonoids in adzuki-meshi (rice boiled with adzuki bean) react with nitrite under simulated stomach conditions". Journal of Functional Foods. 26: 657–666. doi:10.1016/j.jff.2016.08.032.
  5. 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.
  6. Li, Cunfang (2008). "Chemistry of Chinese yew, Taxus chinensis var. mairei". Biochemical Systematics and Ecology. 36 (4): 266–282. doi:10.1016/j.bse.2007.08.002.
  7. 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.
  8. 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.
  9. 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.
  10. Lee, Saet Byoul; Cha, Kwang Hyun; Selenge, Dangaa; Solongo, Amgalan; Nho, Chu Won (2007). "The Chemopreventive Effect of Taxifolin Is Exerted through ARE-Dependent Gene Regulation". Biological & Pharmaceutical Bulletin. 30 (6): 1074–9. doi:10.1248/bpb.30.1074. PMID 17541156.
  11. Luo, Haitao; Jiang, Bing-Hua; King, Sarah; Chen, Yi Charlie (2008). "Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids". Nutrition and Cancer. 60 (6): 800–9. doi:10.1080/01635580802100851. PMID 19005980.
  12. Luo, Haitao; Jiang, Bing-Hua; King, Sarah M.; Chen, Yi Charlie (2008). "Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids". Nutrition and Cancer. 60 (6): 800–809. doi:10.1080/01635580802100851. PMID 19005980.
  13. Rogovskiĭ VS, Matiushin AI, Shimanovskiĭ NL, Semeĭkin AV, Kukhareva TS, Koroteev AM, Koroteev MP, Nifant'ev EE (2010). "[Antiproliferative and antioxidant activity of new dihydroquercetin derivatives]". Eksp Klin Farmakol (in Russian). 73 (9): 39–42. PMID 21086652.
  14. Brusselmans, Koen; Vrolix, Ruth; Verhoeven, Guido; Swinnen, Johannes V. (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.
  15. 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.
  16. 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.
  17. An J, Zuo GY, Hao XY, Wang GC, Li ZS (August 2011). "Antibacterial and synergy of a flavanonol rhamnoside with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA)". Phytomedicine. 18 (11): 990–3. doi:10.1016/j.phymed.2011.02.013. PMID 21466953.
  18. Katavic PL, Lamb K, Navarro H, Prisinzano TE (August 2007). "Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships". J. Nat. Prod. 70 (8): 1278–82. doi:10.1021/np070194x. PMC 2265593. PMID 17685652.
  19. 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.
  20. Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE. 8 (5): e63354. Bibcode:2013PLoSO...863354S. doi:10.1371/journal.pone.0063354. PMC 3653934. PMID 23691032.
  21. Gallori, S. (2004). "Polyphenolic Constituents of Fruit Pulp of Euterpe oleracea Mart. (Açai palm)". Chromatographia. 59 (11–12). doi:10.1365/s10337-004-0305-x (inactive May 2020).
  22. Sakushima, Akiyo; Ohno, Kosei; Coskun, Makusut; Seki, Koh-Ichi; Ohkura, Kazue (2002). "Separation and Identification of Taxifolin 3- O -Glucoside Isomers from Chamaecyparis Obtusa (Cupressaceae)". Natural Product Research. 16 (6): 383–7. doi:10.1080/10575630290033141. PMID 12462342.
  23. 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. doi:10.1584/jpestics.24.123. Archived from the original (PDF) on 2011-07-22.
  24. 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.
  25. 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.
  26. Fossen, Torgils (1998). "Flavonoids from red onion (Allium cepa)". Phytochemistry. 47 (2): 281–285. doi:10.1016/S0031-9422(97)00423-8.
  27. Hosoi, Shinzo; Shimizu, Eri; Ohno, Kosei; Yokosawa, Ryozo; Kuninaga, Shiro; Coskun, Maksut; Sakushima, Akiyo (2006). "Structural Studies of Zoospore Attractants from Trachelospermum jasminoides var. pubescens: Taxifolin 3-O-glycosides". Phytochemical Analysis. 17 (1): 20–4. doi:10.1002/pca.876. PMID 16454472.
  28. Heller, Werner; Britsch, Lothar; Forkmann, Gert; Grisebach, Hans (1985). "Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br". Planta. 163 (2): 191–6. doi:10.1007/BF00393505. PMID 24249337.
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