Miroestrol

Last updated
Miroestrol
Miroestrol.png
Names
IUPAC name
(3R,13S,17R,18S)-7,13,16,17-Tetrahydroxy-2,2-dimethyl-10-oxapentacyclo[14.2.1.03,12.04,9.013,18]nonadeca-4,6,8,11-tetraen-14-one
Other names
(+)-Miroestrol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
Properties
C20H22O6
Molar mass 358.385
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Miroestrol is a phytoestrogen, a plant-derived chemical that mimics the biological activity of the hormone estrogen. Miroestrol was first reportedly isolated from the Thai herb Pueraria mirifica in 1960 and thought to be responsible for the supposed rejuvenating properties of the plant. [1] However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol (shown below), and the reported presence of miroestrol may only have been an artifact of the isolation procedure. [2] When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.

Phytoestrogen Compounds derived from plants, primarily isoflavones that mimic or modulate endogenous estrogens, usually by binding to estrogen receptors

A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating phytoestrogenic plants. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity with estradiol (17-β-estradiol), have the ability to cause estrogenic and/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.

Estrogen primary female sex hormone as well as a medication, is responsible for the development and regulation of the female reproductive system and secondary sex characteristics

Estrogen, or oestrogen, is the primary female sex hormone. It is responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens in females that have estrogenic hormonal activity: estrone, estradiol, and estriol. The estrane steroid estradiol is the most potent and prevalent of these.

Pueraria mirifica, also known as กวาวเครือ Kwao Krua, is a plant found in northern and north eastern Thailand and Myanmar.

Chemical structure of deoxymiroestrol Deoxymiroestrol.png
Chemical structure of deoxymiroestrol

A comparative study of the estrogenic properties of phytoestrogens found that both deoxymiroestrol and miroestrol were comparable in activity in vitro to other known phytoestrogens such as coumestrol as 17β-oestradiol agonists. [3] Because of their estrogenic activities, miroestrol, deoxymiroestrol, and other related compounds have been the targets of scientific research including total synthesis. [4] [5]

<i>In vitro</i> test-tube experiments

In vitro studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology and its subdisciplines are traditionally done in labware such as test tubes, flasks, Petri dishes, and microtiter plates. Studies conducted using components of an organism that have been isolated from their usual biological surroundings permit a more detailed or more convenient analysis than can be done with whole organisms; however, results obtained from in vitro experiments may not fully or accurately predict the effects on a whole organism. In contrast to in vitro experiments, in vivo studies are those conducted in animals, including humans, and whole plants.

Coumestrol 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, a type of chick pea, and Alfalfa sprouts.

Agonist chemical substance which, upon binding to a receptor, leads to its activation

An agonist is a chemical that binds to a receptor and activates the receptor to produce a biological response. Whereas an agonist causes an action, an antagonist blocks the action of the agonist, and an inverse agonist causes an action opposite to that of the agonist.

Extracts of Pueraria mirifica reportedly containing miroestrol are marketed as dietary supplements intended to lead to breast enhancement in women. However, there is a lack of conclusive evidence for such claims. The Federal Trade Commission has taken legal action against marketers for these unproven claims. [6]

Federal Trade Commission Government agency

The Federal Trade Commission (FTC) is an independent agency of the United States government, established in 1914 by the Federal Trade Commission Act. Its principal mission is the promotion of consumer protection and the elimination and prevention of anticompetitive business practices, such as coercive monopoly. It is headquartered in the Federal Trade Commission Building in Washington, D.C.

Related Research Articles

Phytochemistry study of phytochemicals, which are chemicals derived from plants

Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Those studying phytochemistry strive to describe the structures of the large number of secondary metabolic compounds found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. Phytochemicals in food plants are often active in human biology, and in many cases have health benefits. The compounds found in plants are of many kinds, but most are in four major biochemical classes, the alkaloids, glycosides, polyphenols, and terpenes.

Aromatase inhibitor medicine

Aromatase inhibitors (AIs) are a class of drugs used in the treatment of breast cancer in postmenopausal women and gynecomastia in men. They may also be used off-label to reduce estrogen conversion when using external testosterone. They may also be used for chemoprevention in high risk women.

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 Fabaceae family.

Xenoestrogens are a type of xenohormone that imitates estrogen. They can be either synthetic or natural chemical compounds. Synthetic xenoestrogens include some widely used industrial compounds, such as PCBs, BPA, and phthalates, which have estrogenic effects on a living organism even though they differ chemically from the estrogenic substances produced internally by the endocrine system of any organism. Natural xenoestrogens include phytoestrogens which are plant-derived xenoestrogens. Because the primary route of exposure to these compounds is by consumption of phytoestrogenic plants, they are sometimes called "dietary estrogens". Mycoestrogens, estrogenic substances from fungi, are another type of xenoestrogen that are also considered mycotoxins.

Genistein chemical compound

Genistein is an isoflavone that is described as an angiogenesis inhibitor and a phytoestrogen. It was first isolated in 1899 from the dyer's broom, Genista tinctoria; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of prunetol. It was chemically synthesized in 1928.

7-Hydroxymitragynine chemical compound

7-Hydroxymitragynine is a terpenoid indole alkaloid from the plant Mitragyna speciosa, commonly known as Kratom. In mice, it is orally active and has analgesic effects.

Triclocarban chemical compound

Triclocarban is an antibacterial agent common in personal care products like soaps and lotions as well as in the medical field, for which it was originally developed. Studies on its antibacterial qualities and mechanisms are growing. Research suggests that it is similar in its mechanism to triclosan and is effective in fighting infections by targeting the growth of bacteria such as Staphylococcus aureus. Additional research seeks to understand its potential for causing antibacterial resistance and its effects on organismal and environmental health.

Coumestan chemical compound

Coumestan is a heterocyclic organic compound. Coumestan forms the central core of a variety of natural compounds known collectively as coumestans. Coumestans are oxidation products of pterocarpan that are similar to coumarin. Coumestans, including coumestrol, a phytoestrogen, are found in a variety of plants. Food sources high in coumestans include split peas, pinto beans, lima beans, and especially alfalfa and clover sprouts.

Medrogestone chemical compound

Medrogestone, sold under the brand name Colprone among others, is a progestin medication which has been used in menopausal hormone therapy and in the treatment of gynecological disorders. It is available both alone and in combination with an estrogen. It is taken by mouth.

Genistin chemical compound

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 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.

Breast enlargement supplement herbal supplements claiming, without evidence, to enlarge breasts

Breast enlargement supplements are frequently portrayed as being a natural means to increase breast size, and with the suggestion that they are free from risk. The popularity of breast enlargement supplements stems from their heavy promotion toward women. Though there has been historical folklore about using herbs for breast enlargement, there is no scientific evidence to support the effectiveness of any breast enlargement supplement. At times, testimonials by companies have been faked. In the United States, both the Federal Trade Commission and the Food and Drug Administration have taken action against the manufacturers of these products for fraudulent practices. The Mayo Clinic advises that there may be serious drug interactions with their use.

8-Prenylnaringenin chemical compound

8-Prenylnaringenin 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.

Isoxanthohumol chemical compound

Isoxanthohumol is a prenylflavonoid, and it is a phytoestrogen. It is abbreviated as IX or IXN.

Neurodegenerative diseases can disrupt the normal human homeostasis and result in abnormal estrogen levels. For example, neurodegenerative diseases can cause different physiological effects in males and females. In particular, estrogen studies have revealed complex interactions with neurodegenerative diseases. Estrogen was initially proposed to be a possible treatment for certain types of neurodegenerative diseases but a plethora of harmful side effects such as increased susceptibility to breast cancer and coronary heart disease overshadowed any beneficial outcomes. On the other hand, Estrogen Replacement Therapy has shown some positive effects with postmenopausal women. Estrogen and estrogen-like molecules form a large family of potentially beneficial alternatives that can have dramatic effects on human homeostasis and disease. Subsequently, large-scale efforts were initiated to screen for useful estrogen family molecules. Furthermore, scientists discovered new ways to synthesize estrogen-like compounds that can avoid many side effects.

Bisdehydrodoisynolic acid chemical compound

Bisdehydrodoisynolic acid (BDDA), as the (Z)-isomer ( -BDDA), is a synthetic, nonsteroidal estrogen related to doisynolic acid that was never marketed. It is one of the most potent estrogens known, although it has more recently been characterized as a selective estrogen receptor modulator (SERM). BDDA and other doisynolic acid derivatives display relatively low affinity accompanied by disproportionately high estrogenic potency in vivo, which was eventually determined to be due to transformation into metabolites with greater estrogenic activity. The drug was discovered in 1947 as a degradation product of the reaction of equilenin or dihydroequilenin with potassium hydroxide. It is the seco-analogue of equilenin, while doisynolic acid is the seco-analogue of estrone. These compounds, along with diethylstilbestrol, can be considered to be open-ring analogues of estradiol. The methyl ether of BDDA, doisynoestrol, is also an estrogen, and in contrast to BDDA, has been marketed.

Glabrene chemical compound

Glabrene is an isoflavonoid that is found in Glycyrrhiza glabra (licorice). It has estrogenic activity, showing estrogenic effects on breast, vascular, and bone tissue, and hence is a phytoestrogen (IC50 for estrogen receptor binding = 1 μM). It has also been found to act as a tyrosinase inhibitor (IC50 = 3.5 μM) and to inhibit the formation of melanin in melanocytes, and for these reasons, has been suggested as a potential skin-lightening agent.

Mirificin chemical compound

Mirificin, also known as daidzein 8-C-(6-apiofuranosylglucoside), is an isoflavone that is found in Pueraria mirifica and Pueraria lobata. It has estrogenic activity and hence is a phytoestrogen.

References

  1. ↑ Cain, J. C. (1960). "Miroestrol - An Estrogen from the Plant Pueraria mirifica". Nature. 188 (4753): 774–777. doi:10.1038/188774a0. PMID   13689829.
  2. ↑ Chansakaow, S.; Ishikawa, T.; Seki, H.; Sekine, K.; Okada, M.; Chaichantipyuth, C. (2000). "Identification of Deoxymiroestrol as the Actual Rejuvenating Principle of "Kwao Keur", Pueraria mirifica. The Known Miroestrol may be an Artifact". Journal of Natural Products. 63 (2): 173–175. doi:10.1021/np990547v. PMID   10691701.
  3. ↑ Matsumura, A.; Ghosh, A.; Pope, G. S.; Darbre, P. D. (2005). "Comparative Study of Estrogenic Properties of eight Phytoestrogens in MCF7 Human Breast Cancer Cells". Journal of Steroid Biochemistry and Molecular Biology. 94 (5): 431–443. doi:10.1016/j.jsbmb.2004.12.041. PMID   15876408.
  4. ↑ Corey, E. J.; Wu, L. I. (1993). "Enantioselective Total Synthesis of Miroestrol". Journal of the American Chemical Society . 115 (20): 9327–9328. doi:10.1021/ja00073a074.
  5. ↑ Ito, F.; Kumamoto, T.; Yamaguchi, K.; Ishikawa, T. (2009). "Synthetic Studies toward Miroestrols: Trials for Elongation of the Methyl Group of 5-Substituted 2-Methyl-2-Cyclohexanone to 3-Methyl-2-Butenyl Function". Tetrahedron. 65 (4): 771–785. doi:10.1016/j.tet.2008.11.055.
  6. ↑ "Federal Trade Commission v. Vital Dynamics" (PDF). FTC.


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