Taxifolin (5,7,3',4'-flavan-on-ol), also known as dihydroquercetin, belongs to the subclassflavanonols in theflavonoids, which in turn is a class ofpolyphenols. It is extracted from plants such as Siberian larch and milk thistle.
Taxifolin has twostereocenters on the C-ring, as opposed to quercetin which has none.[2] For example, (+)-taxifolin has (2R,3R)-configuration, making it one out of fourstereoisomers that comprise two pairs ofenantiomers.[3]
Taxifolin is present invinegars 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]
Taxifolin is notmutagenic and lesstoxic than the related compoundquercetin.[9] It acts as a potentialchemopreventive agent by regulating genes via an ARE-dependent mechanism.[10] Taxifolin has shown to inhibit theovarian 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 strongcorrelation (with a correlation coefficient of 0.93) between the antiproliferative effects of taxifolin derivatives on murine skinfibroblasts and humanbreast 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]
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.[15]
The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms ofcollagen can be used in medicine.[16] Also taxifolin inhibited the cellularmelanogenesis as effectively asarbutin, one of the most widely used hypopigmenting agents in cosmetics.
Like other flavonoids, taxifolin is able to function as an antifungal agent by blocking multiple pathways that promote the growth and proliferation of fungi.[18][unreliable medical source?]
Taxifolin has also been found to reduce inhibitor of intestinal mobility especially when antagonized by verapamil.[18][unreliable medical source?]
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.[15]
Taxifolin, as well as many other flavonoids, has been found to act as a non-selectiveantagonist of theopioid receptors, albeit with somewhat weakaffinity.[19]Taxifolin shows promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders[20]
(-)-2,3-trans-Dihydroquercetin-3'-O-β-D-glucopyranoside, a taxifolinglucoside has been extracted from the inner bark ofPinus densiflora and can act as an oviposition stimulant in the cerambycid beetleMonochamus alternatus.[24]
(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts ofAgrimonia pilosa.[25]
(2R,3R)-Taxifolin-3'-O-β-D-pyranoglucoside has been isolated from the rhizome ofSmilax glabra.[26]
Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found inred onions.[27]
^Graham HM, Kurth EF (1949). "Constituents of Extractives from Douglas Fir".Industrial and Engineering Chemistry.41 (2):409–414.doi:10.1021/ie50470a035.
^abWillför 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.S2CID97003177.
^Cerezoa AB, Tesfayea W, Soria-Díazb M, Torijac MJ, Mateoc E, Garcia-Parrillaa MC, Troncosoa AM (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.
^Makena PS, Pierce SC, Chung KT, Sinclair SE (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.Bibcode:2009EnvMM..50..451M.doi:10.1002/em.20487.PMID19326464.S2CID25826873.
^Luo H, Jiang BH, King S, Chen YC (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.PMID19005980.S2CID43576449.
^Luo H, Jiang BH, King SM, Chen YC (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.PMID19005980.S2CID43576449.
^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.PMID21086652.
^Tarahovsky YS, Selezneva II, Vasilieva NA, Egorochkin MA, Kim YA (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.PMID18856203.S2CID22328651.
^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.PMID21466953.
^Gallori S (2004). "Polyphenolic Constituents of Fruit Pulp ofEuterpe oleracea Mart. (Açai palm)".Chromatographia.59 (11–12).doi:10.1365/s10337-004-0305-x.S2CID94388806.
^Sakushima A, Ohno K, Coskun M, Seki KI, Ohkura K (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.PMID12462342.S2CID28973885.
^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.PMID2281787.
^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.PMID15575206.
^Hosoi S, Shimizu E, Ohno K, Yokosawa R, Kuninaga S, Coskun M, Sakushima A (2006). "Structural Studies of Zoospore Attractants from Trachelospermum jasminoides var. pubescens: Taxifolin 3-O-glycosides".Phytochemical Analysis.17 (1):20–4.Bibcode:2006PChAn..17...20H.doi:10.1002/pca.876.PMID16454472.
