Rutin
Encyclopedia
Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is a citrus
flavonoid
glycoside
found in buckwheat
, the leaves and petiole
s of Rheum
species, and asparagus
. Rutin is also found in the fruit of the fava d'anta
tree (from Brazil
), fruits and flowers of the pagoda tree, fruits and fruit rinds (especially citrus fruits (orange
, grapefruit
, lemon
, lime
)) and berries such as mulberry
, ash tree
fruits and cranberries
. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. It is sometimes referred to as vitamin P, although not strictly a vitamin.
Rutin is the glycoside
between the flavonol quercetin
and the disaccharide
rutinose
(α-L-Rhamnopyranosyl-(1→6))-β-D-glucopyranose). In fava d'anta, the synthesis is done via a rutin synthase activity.
, is a glycoside of the flavonoid
quercetin. As such, the chemical structures of both are very similar, with the difference existing in the Hydroxyl
functional group. Both quercetin and rutin are used in many countries as medications for blood vessel protection, and are ingredients of numerous multivitamin preparations and herbal remedies.
s from the soil
to the cells in plant
s. In humans, it attaches to the iron ion Fe
2+, preventing it from binding to hydrogen peroxide
, which would otherwise create a highly-reactive free radical that may damage cells. It is also an antioxidant
.
Furthermore, it has been shown to inhibit in vitro
the vascular endothelial growth factor
in subtoxic concentrations, so acts as an inhibitor of angiogenesis
. This finding can be potentially relevant for the control of some cancer
s.
in
mice,
rats,
hamsters
and rabbits,
as well as in vitro
studies,
no clinical studies directly demonstrating significant, positive effects of rutin as dietary supplement in humans exist.
Hydroxyethylrutoside
s, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.
in dogs and cats.
Citrus
Citrus is a common term and genus of flowering plants in the rue family, Rutaceae. Citrus is believed to have originated in the part of Southeast Asia bordered by Northeastern India, Myanmar and the Yunnan province of China...
flavonoid
Flavonoid
Flavonoids , are a class of plant secondary metabolites....
glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
found in buckwheat
Buckwheat
Buckwheat refers to a variety of plants in the dicot family Polygonaceae: the Eurasian genus Fagopyrum, the North American genus Eriogonum, and the Northern Hemisphere genus Fallopia. Either of the latter two may be referred to as "wild buckwheat"...
, the leaves and petiole
Petiole (botany)
In botany, the petiole is the stalk attaching the leaf blade to the stem. The petiole usually has the same internal structure as the stem. Outgrowths appearing on each side of the petiole are called stipules. Leaves lacking a petiole are called sessile, or clasping when they partly surround the...
s of Rheum
Rhubarb
Rhubarb is a group of plants that belong to the genus Rheum in the family Polygonaceae. They are herbaceous perennial plants growing from short, thick rhizomes. They have large leaves that are somewhat triangular-shaped with long fleshy petioles...
species, and asparagus
Asparagus
Asparagus officinalis is a spring vegetable, a flowering perennialplant species in the genus Asparagus. It was once classified in the lily family, like its Allium cousins, onions and garlic, but the Liliaceae have been split and the onion-like plants are now in the family Amaryllidaceae and...
. Rutin is also found in the fruit of the fava d'anta
Dimorphandra mollis
Dimorphandra mollis, the Fava d'anta, is a tree species in the genus of Dimorphandra. It is a plant of the Cerrado vegetation of Brazil.Fava d'anta contains astilbin and rutin....
tree (from Brazil
Brazil
Brazil , officially the Federative Republic of Brazil , is the largest country in South America. It is the world's fifth largest country, both by geographical area and by population with over 192 million people...
), fruits and flowers of the pagoda tree, fruits and fruit rinds (especially citrus fruits (orange
Orange (fruit)
An orange—specifically, the sweet orange—is the citrus Citrus × sinensis and its fruit. It is the most commonly grown tree fruit in the world....
, grapefruit
Grapefruit
The grapefruit , is a subtropical citrus tree known for its sour fruit, an 18th-century hybrid first bred in Barbados. When found, it was named the "forbidden fruit"; it has also been misidentified with the pomelo or shaddock , one of the parents of this hybrid, the other being sweet orange The...
, lemon
Lemon
The lemon is both a small evergreen tree native to Asia, and the tree's ellipsoidal yellow fruit. The fruit is used for culinary and non-culinary purposes throughout the world – primarily for its juice, though the pulp and rind are also used, mainly in cooking and baking...
, lime
Lime (fruit)
Lime is a term referring to a number of different citrus fruits, both species and hybrids, which are typically round, green to yellow in color, 3–6 cm in diameter, and containing sour and acidic pulp. Limes are a good source of vitamin C. Limes are often used to accent the flavors of foods and...
)) and berries such as mulberry
Mulberry
Morus is a genus of flowering plants in the family Moraceae. The 10–16 species of deciduous trees it contains are commonly known as Mulberries....
, ash tree
Ash tree
Fraxinus is a genus flowering plants in the olive and lilac family, Oleaceae. It contains 45-65 species of usually medium to large trees, mostly deciduous though a few subtropical species are evergreen. The tree's common English name, ash, goes back to the Old English æsc, while the generic name...
fruits and cranberries
Cranberry
Cranberries are a group of evergreen dwarf shrubs or trailing vines in the subgenus Oxycoccus of the genus Vaccinium. In some methods of classification, Oxycoccus is regarded as a genus in its own right...
. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. It is sometimes referred to as vitamin P, although not strictly a vitamin.
Rutin is the glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...
between the flavonol quercetin
Quercetin
Quercetin , a flavonol, is a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods.-Occurrence:...
and the disaccharide
Disaccharide
A disaccharide or biose is the carbohydrate formed when two monosaccharides undergo a condensation reaction which involves the elimination of a small molecule, such as water, from the functional groups only. Like monosaccharides, disaccharides form an aqueous solution when dissolved in water...
rutinose
Rutinose
Rutinose is the disaccharide also known as 6-O-L-rhamnosyl-D-glucose that is present in some flavonoid glycosides. It is prepared from rutin by hydrolysis with the enzyme rhamnodiastase....
(α-L-Rhamnopyranosyl-(1→6))-β-D-glucopyranose). In fava d'anta, the synthesis is done via a rutin synthase activity.
Chemical relatives
Rutin (quercetin rutinoside), as well as quercitrinQuercitrin
Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose. It is a constituent of the dye quercitron. It can be found in Tartary buckwheat ....
, is a glycoside of the flavonoid
Flavonoid
Flavonoids , are a class of plant secondary metabolites....
quercetin. As such, the chemical structures of both are very similar, with the difference existing in the Hydroxyl
Hydroxyl
A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...
functional group. Both quercetin and rutin are used in many countries as medications for blood vessel protection, and are ingredients of numerous multivitamin preparations and herbal remedies.
Role as ligand
It can combine with cations, supplying nutrientNutrient
A nutrient is a chemical that an organism needs to live and grow or a substance used in an organism's metabolism which must be taken in from its environment. They are used to build and repair tissues, regulate body processes and are converted to and used as energy...
s from the soil
Soil
Soil is a natural body consisting of layers of mineral constituents of variable thicknesses, which differ from the parent materials in their morphological, physical, chemical, and mineralogical characteristics...
to the cells in plant
Plant
Plants are living organisms belonging to the kingdom Plantae. Precise definitions of the kingdom vary, but as the term is used here, plants include familiar organisms such as trees, flowers, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The group is also called green plants or...
s. In humans, it attaches to the iron ion Fe
Iron
Iron is a chemical element with the symbol Fe and atomic number 26. It is a metal in the first transition series. It is the most common element forming the planet Earth as a whole, forming much of Earth's outer and inner core. It is the fourth most common element in the Earth's crust...
2+, preventing it from binding to hydrogen peroxide
Hydrogen peroxide
Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...
, which would otherwise create a highly-reactive free radical that may damage cells. It is also an antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
.
Furthermore, it has been shown to inhibit in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
the vascular endothelial growth factor
Vascular endothelial growth factor
Vascular endothelial growth factor is a signal protein produced by cells that stimulates vasculogenesis and angiogenesis. It is part of the system that restores the oxygen supply to tissues when blood circulation is inadequate....
in subtoxic concentrations, so acts as an inhibitor of angiogenesis
Angiogenesis
Angiogenesis is the physiological process involving the growth of new blood vessels from pre-existing vessels. Though there has been some debate over terminology, vasculogenesis is the term used for spontaneous blood-vessel formation, and intussusception is the term for the formation of new blood...
. This finding can be potentially relevant for the control of some cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
s.
Health effects
While there is a body of evidence for the effects of rutin and quercetinQuercetin
Quercetin , a flavonol, is a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods.-Occurrence:...
in
mice,
rats,
hamsters
and rabbits,
as well as in vitro
In vitro
In vitro refers to studies in experimental biology that are conducted using components of an organism that have been isolated from their usual biological context in order to permit a more detailed or more convenient analysis than can be done with whole organisms. Colloquially, these experiments...
studies,
no clinical studies directly demonstrating significant, positive effects of rutin as dietary supplement in humans exist.
- Rutin inhibits plateletPlateletPlatelets, or thrombocytes , are small,irregularly shaped clear cell fragments , 2–3 µm in diameter, which are derived from fragmentation of precursor megakaryocytes. The average lifespan of a platelet is normally just 5 to 9 days...
aggregation, as well as decreasing capillary permeability, making the blood thinner and improving circulation. - Rutin shows anti-inflammatoryAnti-inflammatoryAnti-inflammatory refers to the property of a substance or treatment that reduces inflammation. Anti-inflammatory drugs make up about half of analgesics, remedying pain by reducing inflammation as opposed to opioids, which affect the central nervous system....
activity in some animal and in vitro models. - Rutin inhibits aldose reductaseAldose reductaseAldose reductase is an NADPH-dependent oxidoreductase that catalyzes the reduction of a variety of aldehydes and carbonyls, including monosaccharides...
activity. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol sorbitolSorbitolSorbitol, also known as glucitol, Sorbogem® and Sorbo®, is a sugar alcohol that the human body metabolizes slowly. It can be obtained by reduction of glucose, changing the aldehyde group to a hydroxyl group. Sorbitol is found in apples, pears, peaches, and prunes...
. - Rutin also strengthens the capillariesCapillaryCapillaries are the smallest of a body's blood vessels and are parts of the microcirculation. They are only 1 cell thick. These microvessels, measuring 5-10 μm in diameter, connect arterioles and venules, and enable the exchange of water, oxygen, carbon dioxide, and many other nutrient and waste...
, and, therefore, can reduce the symptoms of haemophiliaHaemophiliaHaemophilia is a group of hereditary genetic disorders that impair the body's ability to control blood clotting or coagulation, which is used to stop bleeding when a blood vessel is broken. Haemophilia A is the most common form of the disorder, present in about 1 in 5,000–10,000 male births...
. It also may help to prevent a common, unpleasant-looking, venous edemaEdemaEdema or oedema ; both words from the Greek , oídēma "swelling"), formerly known as dropsy or hydropsy, is an abnormal accumulation of fluid beneath the skin or in one or more cavities of the body that produces swelling...
of the legs; however, a double-blind clinical study on the effect of buckwheat tea containing rutin did not show a significant effect above placebo. - Rutin, as ferulic acidFerulic acidFerulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell wall components such as arabinoxylans as covalent side chains. It is related to trans-cinnamic acid. As a component of lignin, ferulic acid is a precursor in the...
, can reduce the cytotoxicity of oxidized LDL cholesterol and lower the risk of heart diseaseHeart diseaseHeart disease, cardiac disease or cardiopathy is an umbrella term for a variety of diseases affecting the heart. , it is the leading cause of death in the United States, England, Canada and Wales, accounting for 25.4% of the total deaths in the United States.-Types:-Coronary heart disease:Coronary...
. - There is also some evidence that rutin can be used to treat hemorrhoids, varicosis, and microangiopathy.
- Rutin is also an antioxidant; compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest. However, in other trials, the effects of rutin were lower or negligible compared to those of quercetinQuercetinQuercetin , a flavonol, is a plant-derived flavonoid found in fruits, vegetables, leaves and grains. It also may be used as an ingredient in supplements, beverages or foods.-Occurrence:...
.
Hydroxyethylrutoside
Hydroxyethylrutoside
Hydroxyethylrutosides are hydroxyethyl acetylations of rutoside. It may refer to :* Monoxerutin* Dihydroxyethylrutoside* Troxerutin* Tetrahydroxyethylrutoside...
s, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.
In veterinary medicine
Rutin has a veterinary use in the management of chylothoraxChylothorax
A chylothorax is a type of pleural effusion. It results from lymphatic fluid accumulating in the pleural cavity.-Causes:...
in dogs and cats.