Genistin

Last updated
Genistin
Genistin.svg
Names
IUPAC name
7-(β-D-Glucopyranosyloxy)-4′,5-dihydroxyisoflavone
Systematic IUPAC name
5-Hydroxy-3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Genistoside
Genistine
Genistein 7-glucoside
Genistein glucoside
Genistein-7-glucoside
Genisteol 7-monoglucoside
Glucosyl-7-genistein
Genistein 7-O-beta-D-glucoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.120.406 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1 Yes check.svgY
    Key: ZCOLJUOHXJRHDI-CMWLGVBASA-N Yes check.svgY
  • InChI=1/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1
    Key: ZCOLJUOHXJRHDI-CMWLGVBABE
  • O=C3c4c(O)cc(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)cc4O/C=C3/c2ccc(O)cc2
Properties
C21H20O10
Molar mass 432.37 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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. [1] 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 glucosides. The glucosides 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.

Contents

Metabolism

When ingested along the diet, genistin is readily converted to its aglycone 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. [2] It was later found that enzymes 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. [2]

Biological importance

Estrogenic activity

Genistin, like genistein, is a phytoestrogen as it was shown to stimulate estrogen-dependent breast cancer cell growth in vivo. At a concentration 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 tumors to regress. [3]

Antiviral activity

Genistin and other isoflavones 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%. [4]

Bone metabolism

In vitro study have shown that both genistin and genistein are capable of enhancing bone metabolism in the femoral-metaphyseal tissues of elderly rats. [5] 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 enhanced by combination with fructooligosaccharides. [6] 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. [7]

Related Research Articles

Hot flashes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from two to 30 minutes for each occurrence.

<span class="mw-page-title-main">Phytoestrogen</span> Plant-derived xenoestrogen

A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity to estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots.

<span class="mw-page-title-main">Prolactinoma</span> Medical condition

A prolactinoma is a tumor (adenoma) of the pituitary gland that produces the hormone prolactin. It is the most common type of functioning pituitary tumor. Symptoms of prolactinoma are due to abnormally high levels of prolactin in the blood (hyperprolactinemia), or due to pressure of the tumor on surrounding tissues. Based on size, a prolactinoma can be classified as a microprolactinoma or a macroprolactinoma.

<span class="mw-page-title-main">Selective estrogen receptor modulator</span> Drugs acting on the estrogen receptor

Selective estrogen receptor modulators (SERMs), also known as estrogen receptor agonist/antagonists (ERAAs), are a class of drugs that act on the estrogen receptor (ER). A characteristic that distinguishes these substances from pure ER agonists and antagonists is that their action is different in various tissues, thereby granting the possibility to selectively inhibit or stimulate estrogen-like action in various tissues.

<span class="mw-page-title-main">Tamoxifen</span> Medication

Tamoxifen, sold under the brand name Nolvadex among others, is a selective estrogen receptor modulator used to prevent breast cancer in women and men. It is also being studied for other types of cancer. It has been used for Albright syndrome. Tamoxifen is typically taken daily by mouth for five years for breast cancer.

<span class="mw-page-title-main">Equol</span> Isoflavandiol estrogen metabolized from daidzein

Equol (4',7-isoflavandiol) is an isoflavandiol estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones are produced almost exclusively by the members of the bean family, Fabaceae (Leguminosae).

<span class="mw-page-title-main">Genistein</span> Chemical compound

Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen.

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<i>Genista tinctoria</i> Species of flowering plant in the pea and bean family Fabaceae

Genista tinctoria, the dyer's greenweed or dyer's broom, is a species of flowering plant in the family Fabaceae. Its other common names include dyer's whin, waxen woad and waxen wood. The Latin specific epithet tinctoria means "used as a dye".

<span class="mw-page-title-main">GPER</span> Protein-coding gene in the species Homo sapiens

G protein-coupled estrogen receptor 1 (GPER), also known as G protein-coupled receptor 30 (GPR30), is a protein that in humans is encoded by the GPER gene. GPER binds to and is activated by the female sex hormone estradiol and is responsible for some of the rapid effects that estradiol has on cells.

<span class="mw-page-title-main">Estrogen-related receptor alpha</span> Protein-coding gene in the species Homo sapiens

Estrogen-related receptor alpha (ERRα), also known as NR3B1, is a nuclear receptor that in humans is encoded by the ESRRA gene. ERRα was originally cloned by DNA sequence homology to the estrogen receptor alpha, but subsequent ligand binding and reporter-gene transfection experiments demonstrated that estrogens did not regulate ERRα. Currently, ERRα is considered an orphan nuclear receptor.

<span class="mw-page-title-main">Coumestrol</span> Chemical compound

Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957. It has garnered research interest because of its estrogenic activity and prevalence in some foods, including soybeans, brussels sprouts, spinach and a variety of legumes. The highest concentrations of coumestrol are found in clover, Kala Chana, and Alfalfa sprouts.

<span class="mw-page-title-main">Estrone sulfate</span> Chemical compound

Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.

<span class="mw-page-title-main">Glycitein</span> Chemical compound

Glycitein is an O-methylated isoflavone which accounts for 5-10% of the total isoflavones in soy food products. Glycitein is a phytoestrogen with weak estrogenic activity, comparable to that of the other soy isoflavones.

<span class="mw-page-title-main">Formononetin</span> Chemical compound

Formononetin is an O-methylated isoflavone.

<span class="mw-page-title-main">8-Prenylnaringenin</span> Chemical compound

8-Prenylnaringenin (8-PN; also known as flavaprenin, (S)-8-dimethylallylnaringenin, hopein, or sophoraflavanone B) is a prenylflavonoid phytoestrogen. It is reported to be the most estrogenic phytoestrogen known. The compound is equipotent at the two forms of estrogen receptors, ERα and ERβ, and it acts as a full agonist of ERα. Its effects are similar to those of estradiol, but it is considerably less potent in comparison.

<span class="mw-page-title-main">Gynecomastia</span> Endocrine system disorder of human male breast

Gynecomastia is the abnormal non-cancerous enlargement of one or both breasts in males due to the growth of breast tissue as a result of a hormone imbalance between estrogens and androgens. Gynecomastia can cause significant psychological distress or unease.

<span class="mw-page-title-main">Rimostil</span>

Rimostil is a dietary supplement and extract of isoflavones from red clover which was under development by Kazia Therapeutics for the prevention of postmenopausal osteoporosis and cardiovascular disease and for the treatment of menopausal symptoms and hyperlipidemia but was never approved for medical use. It is enriched with isoflavone phytoestrogens such as formononetin, biochanin A, daidzein, and genistein, and is proposed to act as a selective estrogen receptor modulator, with both estrogenic and antiestrogenic effects in different tissues. The extract reached phase II clinical trials for cardiovascular disorders, hyperlipidemia, and postmenopausal osteoporosis prior to the discontinuation of its development in 2007.

<span class="mw-page-title-main">Bahram H. Arjmandi</span> American nutritionist

Bahram H. Arjmandi is an American nutritionist. He is the Margaret A. Sitton Professor at Florida State University (FSU) and is the founder and Director of the Center for Advancing Exercise and Nutrition Research on Aging (CAENRA). He is a researcher in the fields of functional foods and human health. He was among the first to detect the presence of estrogen receptors in the gut linking the importance of estrogen and estrogen receptors in calcium regulation independent of vitamin D.

References

  1. Walter ED (1941). "Genistin (an isoflavone glucoside) and its aglucone, genistein, from soybeans". J Am Chem Soc. 62 (12): 3273–3276. doi:10.1021/ja01857a013.
  2. 1 2 Coldham NG, Darby C, Hows M, King LJ, Zhang AQ, Sauer MJ (2001). "Comparative metabolism of genistin by human and rat gut microflora: detection and identification of the end-products of metabolism". Xenobiotica . 32 (10): 45–62. doi:10.1080/00498250110085809. PMID   11820509.
  3. Allred CD, Ju YH, Allred KF, Chang J, Helferich WG (2001). "Dietary genistin stimulates growth of estrogen-dependent breast cancer tumors similar to that observed with genistein". Carcinogenesis. 22 (10): 1667–1673. doi: 10.1093/carcin/22.10.1667 . PMID   11577007.
  4. Donovan SM, Andres A, Mathai RA, Kuhlenschmidt TB, Kuhlenschmidt MS (2009). "Soy formula and isoflavones and the developing intestine". Nutr. Rev. 67 (S2): 192–200. doi:10.1111/j.1753-4887.2009.00240.x. PMID   19906223.
  5. Yamaguchi M, Gao YH (January 1998). "Anabolic effect of genistein and genistin on bone metabolism in the femoral-metaphyseal tissues of elderly rats: the genistein effect is enhanced by zinc". Mol. Cell. Biochem. 178 (1–2): 377–82. doi:10.1023/A:1006809031836. PMID   9546622.
  6. Hooshmand S, Juma S, Arjmandi BH (2010). "Combination of Genistin and Fructooligosaccharides Prevents Bone Loss in Ovarian Hormone Deficiency". J Med Food. 13 (2): 320–5. doi:10.1089/jmf.2009.0059. PMID   20132047.
  7. Wong RW, Rabie AB (2010). "Effect of genistin on bone formation". Front Biosci. 2 (1): 764–770. PMID   20036920.