Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...

combining the

flavonol Flavonols are a class of flavonoids that have the 3-hydroxyflavone backbone (IUPAC name : 3-hydroxy-2-phenylchromen-4-one). Their diversity stems from the different positions of the phenolic -OH groups. They are distinct from flavanols (with "a ...

quercetin Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor a ...

and the

disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lact ...

rutinose Rutinose is the disaccharide also known as 6-''O''-α-L-rhamnose, rhamnosyl-D-glucose (C12H22O10) that is present in some flavonoid glycosides. It is prepared from rutin by hydrolysis with the enzyme rhamnodiastase. References

* Disaccharide ...

(α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a

flavonoid Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...

found in a wide variety of plants, including

citrus ''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Lemon, lemons, grapefruits, pomelos, and lim ...

Occurrences

Rutin is one of the phenolic compounds found in the invasive plant species, ''

Carpobrotus edulis ''Carpobrotus edulis'' is a ground-creeping plant with succulent leaves in the genus ''Carpobrotus'', native to South Africa. Its common names include hottentot-fig, sour fig, ice plant or highway ice plant. Description ''Carpobrotus edulis'' ...

''. Its name comes from the name of ''

Ruta graveolens ''Ruta graveolens'', commonly known as rue, common rue or herb-of-grace, is a species of '' Ruta'' grown as an ornamental plant and herb. It is native to the Balkan Peninsula. It is grown throughout the world in gardens, especially for its blui ...

'', a plant that also contains rutin. Various citrus fruit peels contain 32 to 49 mg/g of

s expressed as rutin equivalents. Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees, respectively. In 2021, Samoan researchers identified rutin in the native plant, ''matalafi'' (''

Psychotria insularum ''Psychotria insularum'' is a rainforest understory shrub from the coffee family, Rubiaceae. Its native range is the South Pacific. It has traditional uses in herbal medicine. In 2021, the potent anti-inflammatory rutin was isolated from ''P. ...

'').

Metabolism

The enzyme

quercitrinase In enzymology, a quercitrinase () is an enzyme that catalyzes the chemical reaction :quercitrin + H2O \rightleftharpoons L-rhamnose + quercetin Thus, the two substrates of this enzyme are quercitrin and H2O, whereas its two products are L- rh ...

found in ''

Aspergillus flavus ''Aspergillus flavus'' is a saprotrophic and pathogenic fungus with a cosmopolitan distribution. It is best known for its colonization of cereal grains, legumes, and tree nuts. Postharvest rot typically develops during harvest, storage, and/or t ...

'' is in the rutin

catabolic pathway Catabolism () is the set of metabolic pathways that breaks down molecules into smaller units that are either oxidized to release energy or used in other anabolic reactions. Catabolism breaks down large molecules (such as polysaccharides, lipid ...

In food

Rutin is a

found in many plants, including

buckwheat Buckwheat (''Fagopyrum esculentum''), or common buckwheat, is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. The name "buckwheat" is used for several other species, such as '' Fago ...

, the leaves and petioles of ''

Rheum Rheum (; from Greek: ῥεῦμα ''rheuma'' 'a flowing, rheum') is a thin mucus naturally discharged from the eyes, nose, or mouth, often during sleep (cf. mucopurulent discharge).Amodio, Aime"Where Do Eye Boogers Come From?" Families.com bl ...

'' species, and

asparagus Asparagus, or garden asparagus, folk name sparrow grass, scientific name ''Asparagus officinalis'', is a perennial flowering plant species in the genus ''Asparagus''. Its young shoots are used as a spring vegetable. It was once classified in ...

Tartary buckwheat ''Fagopyrum tataricum'', also known as Tartary buckwheat, green buckwheat, ku qiao, Tatar buckwheat, or bitter buckwheat, is a domesticated food plant in the genus ''Fagopyrum'' in the family Polygonaceae. With another species in the same genus, ...

seeds have been found to contain more rutin (about 0.8–1.7% dry weight) than common buckwheat seeds (0.01% dry weight). Rutin is one of the primary flavonols found in 'clingstone'

peach The peach (''Prunus persica'') is a deciduous tree first domesticated and cultivated in Zhejiang province of Eastern China. It bears edible juicy fruits with various characteristics, most called peaches and others (the glossy-skinned, non-fu ...

es. It is also found in

green tea Green tea is a type of tea that is made from '' Camellia sinensis'' leaves and buds that have not undergone the same withering and oxidation process which is used to make oolong teas and black teas. Green tea originated in China, and since the ...

infusions. Approximate rutin content per 100g of selected foods, in

milligrams The kilogram (also kilogramme) is the unit of mass in the International System of Units (SI), having the unit symbol kg. It is a widely used measure in science, engineering and commerce worldwide, and is often simply called a kilo colloquially. ...

per 100

milliliters The litre (international spelling) or liter (American English spelling) (SI symbols L and l, other symbol used: ℓ) is a metric unit of volume. It is equal to 1 cubic decimetre (dm3), 1000 cubic centimetres (cm3) or 0.001 cubic metre (m3). ...

Research

Rutin (rutoside or rutinoside) and other dietary

s are under preliminary

clinical research Clinical research is a branch of healthcare science that determines the safety and effectiveness ( efficacy) of medications, devices, diagnostic products and treatment regimens intended for human use. These may be used for prevention, treatm ...

for their potential biological effects, such as in reducing

post-thrombotic syndrome Post-thrombotic syndrome (PTS), also called postphlebitic syndrome and venous stress disorder is a medical condition that may occur as a long-term complication of deep vein thrombosis (DVT). Signs and symptoms Signs and symptoms of PTS in the leg ...

, venous insufficiency, or

endothelial dysfunction In vascular diseases, endothelial dysfunction is a systemic pathological state of the endothelium. Along with acting as a semi-permeable membrane, the endothelium is responsible for maintaining vascular tone and regulating oxidative stress by ...

, but there was no high-quality evidence for their safe and effective uses as of 2018. A 2020 review indicated that oral rutosides may reduce leg

edema Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's Tissue (biology), tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels t ...

in people with post-thrombotic syndrome, but the risk of

adverse effect An adverse effect is an undesired harmful effect resulting from a medication or other intervention, such as surgery. An adverse effect may be termed a "side effect", when judged to be secondary to a main or therapeutic effect. The term complica ...

s was higher. As a

among similar flavonoids, rutin has low

bioavailability In pharmacology, bioavailability is a subcategory of absorption and is the fraction (%) of an administered drug that reaches the systemic circulation. By definition, when a medication is administered intravenously, its bioavailability is 100%. H ...

due to poor

absorption Absorption may refer to: Chemistry and biology * Absorption (biology), digestion **Absorption (small intestine) *Absorption (chemistry), diffusion of particles of gas or liquid into liquid or solid materials *Absorption (skin), a route by which ...

, high

metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

, and rapid

excretion Excretion is a process in which metabolic waste is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after lea ...

that collectively make its potential for use as a therapeutic agent limited.

Biosynthesis

The biosynthesis pathway of rutin in mulberry (''

Morus alba ''Morus alba'', known as white mulberry, common mulberry and silkworm mulberry, is a fast-growing, small to medium-sized mulberry tree which grows to tall. It is generally a short-lived tree with a lifespan comparable to that of humans, although ...

'' L.) leaves begins with

phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the formula . It can be viewed as a benzyl group substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of alanine. This essential amino a ...

, which produces

cinnamic acid Cinnamic acid is an organic compound with the formula C6H5-CH=CH- COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs n ...

under the action of

phenylalanine ammonia lyase The enzyme phenylalanine ammonia lyase (EC 4.3.1.24) catalyzes the conversion of L-phenylalanine to ammonia and ''trans''-cinnamic acid.: :L-phenylalanine = ''trans''-cinnamate + NH3 Phenylalanine ammonia lyase (PAL) is the first and committed ...

(PAL). Cinnamic acid is catalyzed by cinnamic acid-4-hydroxylase (C4H) and 4-coumarate-CoA ligase (4CL) to form ''p''-

coumaroyl-CoA Coumaroyl-coenzyme A is the thioester of coenzyme-A and coumaric acid. Coumaroyl-coenzyme A is a central intermediate in the biosynthesis of myriad natural products found in plants. These products include lignols (precursors to lignin and lign ...

. Subsequently,

chalcone synthase Chalcone synthase or naringenin-chalcone synthase (CHS) is an enzyme ubiquitous to higher plants and belongs to a family of polyketide synthase enzymes (PKS) known as type III PKS. Type III PKSs are associated with the production of chalcones, a ...

(CHS) catalyzes the condensation of ''p''-coumaroyl-CoA and three molecules of

malonyl-CoA Malonyl-CoA is a coenzyme A derivative of malonic acid. Functions It plays a key role in chain elongation in fatty acid biosynthesis and polyketide biosynthesis. Fatty acid biosynthesis Malonyl-CoA provides 2-carbon units to fatty acids and commi ...

to produce

naringenin chalcone Naringenin chalcone is a common chalconoid (or chalcone, not to be confused with the compound chalcone). It is synthesized from 4-coumaroyl-CoA and malonyl-CoA by chalcone synthase (CHS), a key enzyme in the phenylpropanoid pathway. Naringenin ...

, which is eventually converted into naringenin flavanone with the participation of

chalcone isomerase In enzymology, a chalcone isomerase () is an enzyme that catalyzes the chemical reaction :a chalcone \rightleftharpoons a flavanone Hence, this enzyme has one substrate, a chalcone, and one product, a flavanone. This enzyme belongs to the fam ...

(CHI). With the action of flavanone 3-hydroxylas (F3H),

dihydrokaempferol Aromadendrin (aromodendrin or dihydrokaempferol) is a flavanonol, a type of flavonoid. It can be found in the wood of ''Pinus sibirica''. Metabolism The enzyme dihydrokaempferol 4-reductase uses ''cis''-3,4-leucopelargonidin and NADP+ to pro ...

(DHK) is generated. DHK can be further hydroxylated by flavonoid 3´-hydroxylase (F3'H) to produce

dihydroquercetin 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. Stereocenters Taxifolin has two stereocenters on the C-ring, as opposed to quer ...

(DHQ), which is then catalyzed by

flavonol synthase In enzymology, a flavonol synthase () is an enzyme that catalysis, catalyzes the following chemical reaction : dihydroflavonol + 2-oxoglutarate + \rightleftharpoons a flavonol + succinate + C + H2O The 3 substrate (biochemistry), substrates of ...

(FLS) to form

. After quercetin is catalyzed by UDP-glucose flavonoid 3-''O''-glucosyltransferase (

UFGT In enzymology, a flavonol 3-O-glucosyltransferase () is an enzyme that catalysis, catalyzes the chemical reaction :UDP-glucose + a flavonol \rightleftharpoons UDP + a flavonol 3-O-beta-D-glucoside Thus, the two substrate (biochemistry), substrate ...

) to form

isoquercitrin Isoquercetin, isoquercitrin or isotrifoliin is a flavonoid, a type of chemical compound. It is the 3-''O''-glucoside of quercetin. Isoquercitrin can be isolated from various plant species including ''Mangifera indica'' (mango) and ''Rheum nobile'' ...

, finally, the formation of rutin from isoquercitrin is catalyzed by flavonoid 3-''O''-glucoside L-rhamnosyltransferase.Yu X, Liu J, Wan J, Zhao L, Liu Y, Wei Y, Ouyang Z. Cloning, prokaryotic expression, and enzyme activity of a UDP-glucose flavonoid 3-o-glycosyltransferase from mulberry (Morus alba L.) leaves. Phcog Mag 2020;16:441-7
/ref> Rutin Biosynthesis

References

External links

* {{Vasoprotectives CYP3A4 inhibitors Quercetin glycosides Flavonol rutinosides Flavonoid antioxidants Polyphenols