Genistin
Encyclopedia
Genistin is an isoflavone
found in a number of dietary plants like soy and kudzu
. It was first isolated in 1931 from the 90% methanol extract of a soybean
meal, when it was found that hydrolysis
with hydrochloric acid
produced 1 mole
each of genistein
and glucose
. Chemically it is the 7-O-beta-D-glucoside
form of genistein
and is the predominant form of the isoflavone
naturally occurring in plants. In fact Studies in the 1970s revealed that 99% of the isoflavonoid compounds
in soy are present as their glucoside
s. The glucoside
s are converted by digestive enzymes in the digestive system to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic, estrogenic and anticancer effects are analogous.
form, genistein
. It is hydrolyzed
by removing the covalently bound
glucose
to form genistein
and that genistein
is the form of the compound that is absorbed in the intestine
and is the form responsible for the biological activities of the isoflavone
. The digestive metabolism was first demonstrated in 2002 that the gut microflora played a large role in the conversion of genistin to genistein
. It was later found that enzyme
s present in the human small intestine
and liver
also have the ability to convert the isoflavone
. Hydrolysis
actually starts very quickly in the digestive system once genistin is ingested, conversion begins in the mouth and then continues in the small intestine
. Moreover, both human saliva
and the intestinal cell-free extract from mice
can cause the complete conversion.
-dependent breast cancer
cell growth in vivo. At a concentratio of 1200 ppm
, genistin caused significant increase of growth of breast tumors (MCF-7), cellular proliferation and estrogen-responsive pS2 gene expression in mice
. Removal of genistin or genistein
from the diet caused tumor
s to regress.
s are demonstrated to be bioactive within the neonatal intestine and may reduce the severity of rotavirus
infections; genistin alone shows inhibition of the viral infectivity by 40-60%.
are capable of enhancing bone
metabolism
in the femoral-metaphyseal tissues of elderly rats
. The presence of genistein or genistin in the tissue culture
caused a significant increase in alkaline phosphatase activity
, deoxyribonucleic acid (DNA)
and calcium
contents. The effect of genistein was greater than that of genistin. It is also revealed that genistin has a strong bone loss preventive activity on experimental rats, and is especially enhaced by combination with fructooligosaccharides. The amount of new bone produced by grafting genistin in collagen
matrix was compared to the bone produced by collagen matrix alone in New Zealand White rabbits
, and was observed that genistin caused significant increase in bone formation.
Isoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. Many act as phytoestrogens in mammals...
found in a number of dietary plants like soy and kudzu
Kudzu
Kudzu is a plant in the genus Pueraria in the pea family Fabaceae, subfamily Faboideae. It is a climbing, coiling, and trailing vine native to southern Japan and southeast China. Its name comes from the Japanese name for the plant, . It is a weed that climbs over trees or shrubs and grows so...
. It was first isolated in 1931 from the 90% methanol extract of a soybean
Soybean
The soybean or soya bean is a species of legume native to East Asia, widely grown for its edible bean which has numerous uses...
meal, when it was found that hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
with hydrochloric acid
Hydrochloric acid
Hydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
produced 1 mole
Mole (unit)
The mole is a unit of measurement used in chemistry to express amounts of a chemical substance, defined as an amount of a substance that contains as many elementary entities as there are atoms in 12 grams of pure carbon-12 , the isotope of carbon with atomic weight 12. This corresponds to a value...
each of genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
and glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...
. Chemically it is the 7-O-beta-D-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....
form of genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
and is the predominant form of the isoflavone
Isoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. Many act as phytoestrogens in mammals...
naturally occurring in plants. In fact Studies in the 1970s revealed that 99% of the isoflavonoid compounds
Isoflavonoid
Isoflavonoids are a class of flavonoid polyphenolic compounds. They are biologically active compounds, such as phytoestrogens, produced by pea family plants.Isoflavonoids are derived from the flavonoid biosynthesis pathway via liquiritigenin or naringenin....
in soy are present as their 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....
s. The 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....
s are converted by digestive enzymes in the digestive system to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic, estrogenic and anticancer effects are analogous.
Metabolism
When ingested along the diet, genistin is readily converted to its aglyconeAglycone
An aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The spelling aglycon is sometimes encountered .Classes of phytochemicals found in the aglycone and glycosides forms :...
form, genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
. It is hydrolyzed
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
by removing the covalently bound
Covalent bond
A covalent bond is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. The stable balance of attractive and repulsive forces between atoms when they share electrons is known as covalent bonding....
glucose
Glucose
Glucose is a simple sugar and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate...
to form genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
and that genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
is the form of the compound that is absorbed in the intestine
Intestine
In human anatomy, the intestine is the segment of the alimentary canal extending from the pyloric sphincter of the stomach to the anus and, in humans and other mammals, consists of two segments, the small intestine and the large intestine...
and is the form responsible for the biological activities of the isoflavone
Isoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. Many act as phytoestrogens in mammals...
. The digestive metabolism was first demonstrated in 2002 that the gut microflora played a large role in the conversion of genistin to genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
. It was later found that enzyme
Enzyme
Enzymes are proteins that catalyze chemical reactions. In enzymatic reactions, the molecules at the beginning of the process, called substrates, are converted into different molecules, called products. Almost all chemical reactions in a biological cell need enzymes in order to occur at rates...
s present in the human small intestine
Small intestine
The small intestine is the part of the gastrointestinal tract following the stomach and followed by the large intestine, and is where much of the digestion and absorption of food takes place. In invertebrates such as worms, the terms "gastrointestinal tract" and "large intestine" are often used to...
and liver
Liver
The liver is a vital organ present in vertebrates and some other animals. It has a wide range of functions, including detoxification, protein synthesis, and production of biochemicals necessary for digestion...
also have the ability to convert the isoflavone
Isoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. Many act as phytoestrogens in mammals...
. Hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...
actually starts very quickly in the digestive system once genistin is ingested, conversion begins in the mouth and then continues in the small intestine
Small intestine
The small intestine is the part of the gastrointestinal tract following the stomach and followed by the large intestine, and is where much of the digestion and absorption of food takes place. In invertebrates such as worms, the terms "gastrointestinal tract" and "large intestine" are often used to...
. Moreover, both human saliva
Saliva
Saliva , referred to in various contexts as spit, spittle, drivel, drool, or slobber, is the watery substance produced in the mouths of humans and most other animals. Saliva is a component of oral fluid. In mammals, saliva is produced in and secreted from the three pairs of major salivary glands,...
and the intestinal cell-free extract from mice
MICE
-Fiction:*Mice , alien species in The Hitchhiker's Guide to the Galaxy*The Mice -Acronyms:* "Meetings, Incentives, Conferencing, Exhibitions", facilities terminology for events...
can cause the complete conversion.
Estrogenic activity
Genistin, like genistein, is a phytoestrogen as it was shown to stimulate estrogenEstrogen
Estrogens , oestrogens , or œstrogens, are a group of compounds named for their importance in the estrous cycle of humans and other animals. They are the primary female sex hormones. Natural estrogens are steroid hormones, while some synthetic ones are non-steroidal...
-dependent breast 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...
cell growth in vivo. At a concentratio of 1200 ppm
PPM
- Culture :*Peter, Paul and Mary, a 1960s folk music trio*Picture Postcard Monthly, a magazine for collectors of postcards*Please Please Me, the first album by The Beatles- Health :*Permanent pacemaker or artificial pacemaker...
, genistin caused significant increase of growth of breast tumors (MCF-7), cellular proliferation and estrogen-responsive pS2 gene expression in mice
MICE
-Fiction:*Mice , alien species in The Hitchhiker's Guide to the Galaxy*The Mice -Acronyms:* "Meetings, Incentives, Conferencing, Exhibitions", facilities terminology for events...
. Removal of genistin or genistein
Genistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
from the diet caused tumor
Tumor
A tumor or tumour is commonly used as a synonym for a neoplasm that appears enlarged in size. Tumor is not synonymous with cancer...
s to regress.
Antiviral activity
Genistin and other isoflavoneIsoflavone
Isoflavones comprise a class of organic compounds, often naturally occurring, related to the isoflavonoids. Many act as phytoestrogens in mammals...
s are demonstrated to be bioactive within the neonatal intestine and may reduce the severity of rotavirus
Rotavirus
Rotavirus is the most common cause of severe diarrhoea among infants and young children, and is one of several viruses that cause infections often called stomach flu, despite having no relation to influenza. It is a genus of double-stranded RNA virus in the family Reoviridae. By the age of five,...
infections; genistin alone shows inhibition of the viral infectivity by 40-60%.
Bone metabolism
In vitro study have shown that both genistin and genisteinGenistein
Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, also in the medicinal plant, Flemingia vestita and coffee Besides functioning as...
are capable of enhancing bone
Bone
Bones are rigid organs that constitute part of the endoskeleton of vertebrates. They support, and protect the various organs of the body, produce red and white blood cells and store minerals. Bone tissue is a type of dense connective tissue...
metabolism
Metabolism
Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...
in the femoral-metaphyseal tissues of elderly rats
RATS
RATS may refer to:* RATS , Regression Analysis of Time Series, a statistical package* Rough Auditing Tool for Security, a computer program...
. The presence of genistein or genistin in the tissue culture
Tissue culture
Tissue culture is the growth of tissues or cells separate from the organism. This is typically facilitated via use of a liquid, semi-solid, or solid growth medium, such as broth or agar...
caused a significant increase in alkaline phosphatase activity
Phosphatase
A phosphatase is an enzyme that removes a phosphate group from its substrate by hydrolysing phosphoric acid monoesters into a phosphate ion and a molecule with a free hydroxyl group . This action is directly opposite to that of phosphorylases and kinases, which attach phosphate groups to their...
, deoxyribonucleic acid (DNA)
DNA
Deoxyribonucleic acid is a nucleic acid that contains the genetic instructions used in the development and functioning of all known living organisms . The DNA segments that carry this genetic information are called genes, but other DNA sequences have structural purposes, or are involved in...
and calcium
Calcium
Calcium is the chemical element with the symbol Ca and atomic number 20. It has an atomic mass of 40.078 amu. Calcium is a soft gray alkaline earth metal, and is the fifth-most-abundant element by mass in the Earth's crust...
contents. The effect of genistein was greater than that of genistin. It is also revealed that genistin has a strong bone loss preventive activity on experimental rats, and is especially enhaced by combination with fructooligosaccharides. The amount of new bone produced by grafting genistin in 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...
matrix was compared to the bone produced by collagen matrix alone in New Zealand White rabbits
Rabbit
Rabbits are small mammals in the family Leporidae of the order Lagomorpha, found in several parts of the world...
, and was observed that genistin caused significant increase in bone formation.