Taxifolin

Taxifolin
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
CAS number	480-18-2 N
PubChem	439533
	ChEBI	CHEBI:17948 N
ChEMBL	CHEMBL66 N
Jmol-3D images	{{#if:OC1=C(C([C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)=O)C3=CC(O)=C1|Image 1
SMILES OC1=C(C([C@H](O)[C@@H](C2=CC(O)=C(O)C=C2)O3)=O)C3=CC(O)=C1
Properties
Molecular formula	C15H12O7
Molar mass	304.25 g mol−1
Appearance	brown powder
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 açaí palm, in the silymarin extract from the milk thistle seeds and in small quantities in red onion.

Pharmacology

Taxifolin is not mutagenic and low toxic compared to the related compound quercetin.^[3] It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism.^[4] Taxifolin has shown to inhibit the ovarian cancer cell growth in a dose-dependent manner.^[5] 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.^[6]

The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen can be used in medicine.^[7] 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.^[8]

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).^[9]

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 3-O-glucoside isomers have been separated from Chamaecyparis obtusa.^[10]

(-)-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.^[11]

(2S,3S)-(-)-Taxifolin-3-O-β-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.^[12]

(2R,3R)-Taxifolin-3'-O-β-D-pyranglucoside has been isolated from the rhizome of Smilax glabra.^[13]

(2R,3R)-Taxifolin 3-O-arabinoside and (2S,3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides^[14] (star jasmine).

Chemistry

(+)-Leucocyanidin [(2R,3S,4R)-3,4,5,7,3,4-hexahydroxyflavan] can be synthesized from taxifolin by sodium borohydride reduction.^[15]

References