Taxifolin
Encyclopedia
Taxifolin is a flavanonol
, a type of flavonoid. It can be found in the açaí palm
, in the Siberian larch
(Larix sibirica) in Russia and in the silymarin extract from the milk thistle
seeds. It's also found in small quantities in red onion
.
cell growth in a dose-dependent manner. 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.
The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen
can be used in medicine. 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.
Taxifolin enhanced also the efficacy of conventional antibiotics like levofloxacin
and ceftazidime
in vitro, which have potential for combinatory therapy of patients infected with MRSA.
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, trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.
is the 3-O-rhamnoside of taxifolin.
Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa
.
(-)-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.
(2S,3S)-(-)-taxifolin-3-O-beta-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.
(2R,3R)-taxifolin-3'-O-beta-D-pyranglucoside has been isolated from the rhizome of Smilax glabra.
(2R, 3R)-taxifolin 3-O-arabinoside and (2S, 3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides
(star jasmine).
[(2R,3S,4R)-3,4,5,7,3,4-hexahydroxyflavan] can be synthesized from (+)dihydroquercetin by sodium borohydride
reduction.
Flavanonol
The flavanonols are a class of flavonoids that use the 3-hydroxy-2,3-dihydro-2-phenylchromen-4-one backbone.Some examples include:* Taxifolin...
, a type of flavonoid. It can be found in the açaí palm
Açaí Palm
The açaí palm is a species of palm tree in the genus Euterpe cultivated for their fruit and superior hearts of palm. Its name comes from the Portuguese adaptation of the Tupian word ïwasa'i, '[fruit that] cries or expels water'. Global demand for the fruit has expanded rapidly in recent years,...
, in the Siberian larch
Siberian Larch
The Siberian Larch or Russian Larch is a frost-hardy tree native to western Russia, from close to the Finnish border east to the Yenisei valley in central Siberia, where it hybridises with the Dahurian Larch L...
(Larix sibirica) in Russia and in the silymarin extract from the milk thistle
Milk thistle
The milk thistle is a thistle of the genus Silybum Adans., a flowering plant of the daisy family . They are native to the Mediterranean regions of Europe, North Africa and the Middle East...
seeds. It's also found in small quantities in red onion
Red onion
Red onions, sometimes called purple onions, are cultivars of the onion with purplish red skin and white flesh tinged with red.These onions tend to be medium to large in size and have a mild to sweet flavor. They are often consumed raw, grilled or lightly cooked with other foods, or added as color...
.
Pharmacology
Taxifolin is not mutagenic and low toxic compared to Qercetin. It acts as a potential chemopreventive agent by regulating genes via an ARE-dependent mechanism. Taxifolin has shown to inhibit the ovarian cancerOvarian cancer
Ovarian cancer is a cancerous growth arising from the ovary. Symptoms are frequently very subtle early on and may include: bloating, pelvic pain, difficulty eating and frequent urination, and are easily confused with other illnesses....
cell growth in a dose-dependent manner. There is also a strong correlation
Correlation
In statistics, dependence refers to any statistical relationship between two random variables or two sets of data. Correlation refers to any of a broad class of statistical relationships involving dependence....
(with a correlation coefficient of 0.93) between the antiproliferative effects of dihydroquercetin (DHQ, Taxifolin) derivatives on murine skin fibroblasts and human
Human
Humans are the only living species in the Homo genus...
breast cancer
Breast cancer
Breast cancer is cancer originating from breast tissue, most commonly from the inner lining of milk ducts or the lobules that supply the ducts with milk. Cancers originating from ducts are known as ductal carcinomas; those originating from lobules are known as lobular carcinomas...
cells.
The capacity of taxifolin to stimulate fibril formation and promote stabilization of fibrillar forms of collagen
Collagen
Collagen is a group of naturally occurring proteins found in animals, especially in the flesh and connective tissues of mammals. It is the main component of connective tissue, and is the most abundant protein in mammals, making up about 25% to 35% of the whole-body protein content...
can be used in medicine. Also taxifolin inhibited the cellular melanogenesis as effectively as arbutin
Arbutin
Arbutin is both an ether and a glycoside; a glycosylated hydroquinone extracted from bearberry plant in the genus Arctostaphylos. It inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Arbutin is found in wheat, and is concentrated...
, one of the most widely used hypopigmenting agents in cosmetics. However, arbutin acts as quercetin extremely mutagenic, carcinogenic and toxic.
Taxifolin enhanced also the efficacy of conventional antibiotics like levofloxacin
Levofloxacin
Levofloxacin is a synthetic chemotherapeutic antibiotic of the fluoroquinolone drug class and is used to treat severe or life-threatening bacterial infections or bacterial infections that have failed to respond to other antibiotic classes. It is sold under various brand names, such as Levaquin and...
and ceftazidime
Ceftazidime
Ceftazidime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram-positive and Gram-negative bacteria. Unlike most third-generation agents, it is active against Pseudomonas aeruginosa, however it has weaker activity...
in vitro, which have potential for combinatory therapy of patients infected with MRSA.
Metabolism
The enzyme Taxifolin 8-monooxygenaseTaxifolin 8-monooxygenase
In enzymology, a taxifolin 8-monooxygenase is an enzyme that catalyzes the chemical reactionThe 5 substrates of this enzyme are taxifolin, NADH, NADPH, H+, and O2, whereas its 4 products are 2,3-dihydrogossypetin, NAD+, NADP+, and H2O....
uses taxifolin, NADH, NADPH, H+, and O2 to produce 2,3-dihydrogossypetin
Dihydrogossypetin
Dihydrogossypetin is a flavanonol, a type of flavonoid. -Metabolism:The enzyme Taxifolin 8-monooxygenase uses taxifolin, NADH, NADPH, H+, and O2 to produce 2,3-dihydrogossypetin, NAD+, NADP+, and H2O....
, NAD+, NADP+, and H2O.
The enzyme leucocyanidin oxygenase
Leucocyanidin oxygenase
In enzymology, a leucocyanidin oxygenase is an enzyme that catalyzes the chemical reactionThe 3 substrates of this enzyme are leucocyanidin, 2-oxoglutarate, and O2, whereas its 5 products are cis-dihydroquercetin, trans-dihydroquercetin, succinate, CO2, and H2O.This enzyme belongs to the family of...
uses leucocyanidin
Leucocyanidin
Leucocyanidin is a colorless chemical compound related to leucoanthocyanidins. Leucoyanidin can be found in Aesculus hippocastanum , Anacardium occidentale , Arachis hypogaea , Areca catechu , Asimina triloba , Cerasus vulgaris , Cinnamomum camphora , Erythroxylon...
, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.
Glycosides
AstilbinAstilbin
Astilbin is a flavanonol, a type of flavonoid. Astilbin is the -isomer; neoisoastilbin is the -isomer and isoastilbin is the -isomer....
is the 3-O-rhamnoside of taxifolin.
Taxifolin 3-O-glucoside isomers have been separated from Chamaecyparis obtusa
Chamaecyparis obtusa
Chamaecyparis obtusa is a species of cypress native to central Japan.It is a slow-growing tree which grows to 35 m tall with a trunk up to 1 m in diameter. The bark is dark red-brown...
.
(-)-2,3-trans-dihydroquercetin-3'-O-β-D-glucopyranoside, a taxifolin glucoside
Glucoside
A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes....
has been extracted from the inner bark of Pinus densiflora and can act as an oviposition stimulant in the cerambycid beetle Monochamus alternatus.
(2S,3S)-(-)-taxifolin-3-O-beta-D-glucopyranoside has been isolated from the root-sprouts of Agrimonia pilosa.
(2R,3R)-taxifolin-3'-O-beta-D-pyranglucoside has been isolated from the rhizome of Smilax glabra.
(2R, 3R)-taxifolin 3-O-arabinoside and (2S, 3S)-taxifolin 3-O-arabinoside have been isolated from the leaves of Trachelospermum jasminoides
Trachelospermum jasminoides
Trachelospermum jasminoides is a species of flowering plant in the milkweed family, Apocynaceae, that is native to eastern and southeastern Asia, into Japan, Korea, southern China, and Vietnam. Common names include Star Jasmine, Confederate Jasmine, and Trader's Compass.-Description:Trachelospermum...
(star jasmine).
Chemistry
(+)LeucocyanidinLeucocyanidin
Leucocyanidin is a colorless chemical compound related to leucoanthocyanidins. Leucoyanidin can be found in Aesculus hippocastanum , Anacardium occidentale , Arachis hypogaea , Areca catechu , Asimina triloba , Cerasus vulgaris , Cinnamomum camphora , Erythroxylon...
[(2R,3S,4R)-3,4,5,7,3,4-hexahydroxyflavan] can be synthesized from (+)dihydroquercetin by sodium borohydride
Sodium borohydride
Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are...
reduction.