Taxifolin

Taxifolin has two stereocenters on the C-ring, as opposed to quercetin which has none.{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/5280343|title=Quercetin|website=pubchem.ncbi.nlm.nih.gov}} For example, (+)-taxifolin has (2R,3R)-configuration, making it one out of four stereoisomers that comprise two pairs of enantiomers.{{cite web|url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17948|title=(+)-taxifolin (CHEBI:17948)|website=www.ebi.ac.uk}}

Taxifolin is found in non-glutinous rice boiled with adzuki bean (adzuki-meshi).{{cite journal |title=Antioxidative flavonoids in adzuki-meshi (rice boiled with adzuki bean) react with nitrite under simulated stomach conditions |url=https://www.sciencedirect.com/science/article/abs/pii/S1756464616302468 |author=Takahama |date=2016-10-01 |doi=10.1016/j.jff.2016.08.032 |volume=26 |journal=Journal of Functional Foods |pages=657–666 }}

It can be found in conifers like the Siberian larch, Larix sibirica, in Russia, in Pinus roxburghii,{{cite journal |title=Extractives in bark of different conifer species growing in Pakistan |vauthors=Willför S, Mumtaz A, Karonen M, Reunanen M, Mohammad A, Harlamow R |journal=Holzforschung |date=August 2009 |volume=63 |issue=5 |pages=551–558 |doi=10.1515/HF.2009.095|s2cid=97003177 }} in Cedrus deodara and in the Chinese yew, Taxus chinensis var. mairei.{{cite journal | doi = 10.1016/j.bse.2007.08.002 | volume=36 | title=Chemistry of Chinese yew, Taxus chinensis var. mairei | year=2008 | journal=Biochemical Systematics and Ecology | pages=266–282 | last1 = Li | first1 = Cunfang| issue=4 | bibcode=2008BioSE..36..266L }}

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

Taxifolin is present in vinegars aged in cherry wood.{{cite journal | last1 = Cerezoa | first1 = Ana B. | last2 = Tesfayea | first2 = Wendu | last3 = Soria-Díazb | first3 = M.E. | last4 = Torijac | first4 = M. Jesús | last5 = Mateoc | first5 = Estíbaliz | last6 = Garcia-Parrillaa | first6 = M. Carmen | last7 = Troncosoa | first7 = Ana M. | year = 2010 | title = Effect of wood on the phenolic profile and sensory properties of wine vinegars during ageing | journal = Journal of Food Composition and Analysis | volume = 23 | issue = 2| pages = 175–184 | doi = 10.1016/j.jfca.2009.08.008 }}

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.{{cite journal | last1 = Brusselmans | first1 = K. | last2 = Vrolix | first2 = R. | last3 = Verhoeven | first3 = G. | last4 = Swinnen | first4 = J. | year = 2005 | title = Induction of Cancer Cell Apoptosis by Flavonoids Is Associated with Their Ability to Inhibit Fatty Acid Synthase Activity | journal = Journal of Biological Chemistry | volume = 280 | issue = 7| pages = 5636–5645 | doi = 10.1074/jbc.m408177200 | pmid = 15533929 | doi-access = free }}

Taxifolin is not mutagenic and less toxic than the related compound quercetin.{{cite journal |last1=Makena |first1=Patrudu S. |last2=Pierce |first2=Samuel C. |last3=Chung |first3=King-Thom |last4=Sinclair |first4=Scott E. |title=Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP-2 uvrA |journal=Environmental and Molecular Mutagenesis |volume=50 |issue=6 |pages=451–9 |year=2009 |pmid=19326464 |doi=10.1002/em.20487|bibcode=2009EnvMM..50..451M |s2cid=25826873 }} It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism.{{cite journal |last1=Lee |first1=Saet Byoul |last2=Cha |first2=Kwang Hyun |last3=Selenge |first3=Dangaa |last4=Solongo |first4=Amgalan |last5=Nho |first5=Chu Won |title=The Chemopreventive Effect of Taxifolin Is Exerted through ARE-Dependent Gene Regulation |journal=Biological & Pharmaceutical Bulletin |volume=30 |pages=1074–9 |year=2007 |doi=10.1248/bpb.30.1074 |pmid=17541156 |issue=6|doi-access=free }} Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.{{cite journal |last1=Luo |first1=Haitao |last2=Jiang |first2=Bing-Hua |last3=King |first3=Sarah |last4=Chen |first4=Yi Charlie |title=Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids |journal=Nutrition and Cancer |volume=60 |issue=6 |pages=800–9 |year=2008 |pmid=19005980 |doi=10.1080/01635580802100851|s2cid=43576449 }} However, in this same study, taxifolin was the least effective flavonoid in the inhibition of VEGF expression.{{cite journal | doi = 10.1080/01635580802100851 | pmid = 19005980 | title = Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids | journal = Nutrition and Cancer | volume = 60 | issue = 6 | pages = 800–809 | year = 2008 | last1 = Luo | first1 = Haitao | last2 = Jiang | first2 = Bing-Hua | last3 = King | first3 = Sarah M. | last4 = Chen | first4 = Yi Charlie | s2cid = 43576449 }} 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.{{cite journal |vauthors=Rogovskiĭ VS, Matiushin AI, Shimanovskiĭ NL, Semeĭkin AV, Kukhareva TS, Koroteev AM, Koroteev MP, Nifant'ev EE |title=[Antiproliferative and antioxidant activity of new dihydroquercetin derivatives] |language=ru |journal=Eksp Klin Farmakol |volume=73 |issue=9 |pages=39–42 |year=2010 |pmid=21086652 }}

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.{{cite journal | doi = 10.1074/jbc.M408177200 | pmid = 15533929 | title = Induction of Cancer Cell Apoptosis by Flavonoids is Associated with Their Ability to Inhibit Fatty Acid Synthase Activity | journal = Journal of Biological Chemistry | volume = 280 | issue = 7 | pages = 5636–5645 | year = 2005 | last1 = Brusselmans | first1 = Koen | last2 = Vrolix | first2 = Ruth | last3 = Verhoeven | first3 = Guido | last4 = Swinnen | first4 = Johannes V. | doi-access = free }}

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.{{cite journal |last1=Das |first1=A. |last2=Baidya |first2=R. |last3=Chakraborty |first3=T. |last4=Samanta |first4=A. K. |last5=Roy |first5=S. |title=Pharmacological basis and new insights of taxifolin: A comprehensive review |journal=Biomedicine & Pharmacotherapy |year=2021 |volume=142 |doi=10.1016/j.biopha.2021.112004|pmid=34388527 |doi-access=free }}

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine.{{cite journal |last1=Tarahovsky |first1=Y. S. |last2=Selezneva |first2=I. I. |last3=Vasilieva |first3=N. A. |last4=Egorochkin |first4=M. A. |last5=Kim |first5=Yu. A. |title=Acceleration of fibril formation and thermal stabilization of collagen fibrils in the presence of taxifolin (dihydroquercetin) |journal=Bulletin of Experimental Biology and Medicine |volume=144 |issue=6 |pages=791–4 |year=2007 |pmid=18856203 |doi=10.1007/s10517-007-0433-z|s2cid=22328651 }} Also taxifolin inhibited the cellular melanogenesis as effectively as arbutin, one of the most widely used hypopigmenting agents in cosmetics.

Taxifolin also enhances the efficacy of conventional antibiotics such as levofloxacin and ceftazidime in vitro, which have potential for combinatory therapy of patients infected with methicillin-resistant Staphylococcus aureus (MRSA).{{cite journal | pmid = 21466953 | doi=10.1016/j.phymed.2011.02.013 | volume=18 | issue=11 | title=Antibacterial and synergy of a flavanonol rhamnoside with antibiotics against clinical isolates of methicillin-resistant Staphylococcus aureus (MRSA) |date=August 2011 | journal=Phytomedicine | pages=990–3 |vauthors=An J, Zuo GY, Hao XY, Wang GC, Li ZS }}

Like other flavonoids, taxifolin is able to function as an antifungal agent by blocking multiple pathways that promote the growth and proliferation of fungi.{{Cite journal |last1=Asmi |first1=K. Saftar |last2=Lakshmi |first2=T. |last3=Balusamy |first3=Sri Renukadevi |last4=Parameswari |first4=R. |date=2017 |title=Therapeutic Aspects of Taxifolin – An Update |url=https://japer.in/article/therapeutic-aspects-of-taxifolin-an-update |journal=Journal of Advanced Pharmacy Education and Research|volume=7 |issue=3–2017 |pages=187–189 }}{{medrs|date=July 2024}}

Taxifolin has also been found to reduce inhibitor of intestinal mobility especially when antagonized by verapamil.{{medrs|date=July 2024}}

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.

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.{{cite journal |vauthors=Katavic PL, Lamb K, Navarro H, Prisinzano TE | title = Flavonoids as opioid receptor ligands: identification and preliminary structure-activity relationships | journal = J. Nat. Prod. | volume = 70 | issue = 8 | pages = 1278–82 |date=August 2007 | pmid = 17685652 | pmc = 2265593 | doi = 10.1021/np070194x }}

Taxifolin shows promising pharmacological activities in the management of inflammation, tumors, microbial infections, oxidative stress, cardiovascular, and liver disorders {{cite journal | doi = 10.1016/J.PHYTOCHEM.2019.112066 | pmid = 31325613 | title = An insight into the health-promoting effects of taxifolin (dihydroquercetin) | journal = Phytochemistry | volume = 166 | pages = 112066 | year = 2019 | last1 = Sunil | first1 = Christudas | last2 = Xu | first2 = Baojun | bibcode = 2019PChem.166k2066S | s2cid = 198131999 }}

Taxifolin has been found to act as an agonist of the adiponectin receptor 2 (AdipoR2).{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354 | bibcode = 2013PLoSO...863354S | doi-access = free }}

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.

Astilbin is the 3-O-rhamnoside of taxifolin. Taxifolin deoxyhexose can be found in açai fruits.{{cite journal | doi = 10.1365/s10337-004-0305-x | volume=59 | title=Polyphenolic Constituents of Fruit Pulp of Euterpe oleracea Mart. (Açai palm) | year=2004 | journal=Chromatographia | last1 = Gallori | first1 = S.| issue=11–12 |s2cid=94388806 }}

Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa.{{cite journal |last1=Sakushima |first1=Akiyo |last2=Ohno |first2=Kosei |last3=Coskun |first3=Makusut |last4=Seki |first4=Koh-Ichi |last5=Ohkura |first5=Kazue |title=Separation and Identification of Taxifolin 3- O -Glucoside Isomers from Chamaecyparis Obtusa (Cupressaceae) |journal=Natural Product Research |volume=16 |pages=383–7 |year=2002 |doi=10.1080/10575630290033141 |pmid=12462342 |issue=6|s2cid=28973885 }}

(-)-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.{{cite journal |first1=Masashi |last1=Sato |first2=Syed Q. |last2=Islam |first3=Shinobu |last3=Awata |first4=Tory |last4=Yamasaki |year=1999 |title=Flavanonol glucoside and proanthocyanidins: Oviposition stimulants for the cerambycid beetle, Monochamus alternatus |journal=Journal of Pesticide Science |volume=24 |issue=2 |pages=123–9 |doi=10.1584/jpestics.24.123 |doi-access=free }}

(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.{{cite journal |vauthors=Pei YH, Li X, Zhu TR, Wu LJ |title=[Studies on the structure of a new flavanonol glucoside of the root-sprouts of Agrimonia pilosa Ledeb] |language=zh |journal=Yao Xue Xue Bao |volume=25 |issue=4 |pages=267–70 |year=1990 |pmid=2281787}}

(2R,3R)-Taxifolin-3'-O-β-D-pyranoglucoside has been isolated from the rhizome of Smilax glabra.{{cite journal |vauthors=Yuan JZ, Dou DQ, Chen YJ, etal |title=[Studies on dihydroflavonol glycosides from rhizome of Smilax glabra] |language=zh |journal=Zhongguo Zhong Yao Za Zhi |volume=29 |issue=9 |pages=867–70 |date=September 2004 |pmid=15575206}}

Minor amount of taxifolin 4′-O-β-glucopyranoiside can be found in red onions.{{cite journal | doi = 10.1016/S0031-9422(97)00423-8 | volume=47 | title=Flavonoids from red onion (Allium cepa) | year=1998 | journal=Phytochemistry | pages=281–285 | last1 = Fossen | first1 = Torgils| issue=2 | bibcode=1998PChem..47..281F }}

(2R,3R)-Taxifolin 3-O-arabinoside and (2S,3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides{{cite journal |last1=Hosoi |first1=Shinzo |last2=Shimizu |first2=Eri |last3=Ohno |first3=Kosei |last4=Yokosawa |first4=Ryozo |last5=Kuninaga |first5=Shiro |last6=Coskun |first6=Maksut |last7=Sakushima |first7=Akiyo |title=Structural Studies of Zoospore Attractants from Trachelospermum jasminoides var. pubescens: Taxifolin 3-O-glycosides |journal=Phytochemical Analysis |volume=17 |issue=1 |pages=20–4 |year=2006 |pmid=16454472 |doi=10.1002/pca.876|bibcode=2006PChAn..17...20H }} (star jasmine).

• [https://perfecthealthsciences.com/dihydroquercetin Dihydroquercetin]-3-O-rhamnoside (Astilbin)
• (+)-Leucocyanidin can be synthesized from taxifolin by sodium borohydride reduction.{{cite journal |last1=Heller |first1=Werner |last2=Britsch |first2=Lothar |last3=Forkmann |first3=Gert |last4=Grisebach |first4=Hans |title=Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br |journal=Planta |volume=163 |issue=2 |pages=191–6 |year=1985 |doi=10.1007/BF00393505 |pmid=24249337|bibcode=1985Plant.163..191H |s2cid=20854538 }}

{{Reflist|2}}

{{Opioid receptor modulators}}

{{Flavanonols}}

Category:Adiponectin receptor agonists

Category:Flavanonols

Category:Catechols

Category:Resorcinols

Category:Kappa-opioid receptor antagonists

Category:Mu-opioid receptor antagonists

Category:3-Hydroxypropenals

Category:Wood extracts