O-Desmethylangolensin

Last updated
O-Desmethylangolensin
Desmethylangolensin.svg
Names
IUPAC name
1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)-1-propanone
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.230.083 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3
    Key: JDJPNKPFDDUBFV-UHFFFAOYSA-N
  • CC(c1ccc(cc1)O)C(=O)c2ccc(cc2O)O
Properties
C15H14O4
Molar mass 258.273 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Danger
H302, H318, H410
P264, P270, P273, P280, P301+P312, P305+P351+P338, P310, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

O-Desmethylangolensin (O-DMA) is a phytoestrogen. It is an intestinal bacterial metabolite of the soy phytoestrogen daidzein. [1] It produced in some people, deemed O-DMA producers, but not others. [1] O-DMA producers were associated with 69% greater mammographic density and 6% bone density. [1]

See also

Related Research Articles

Direct memory access (DMA) is a feature of computer systems that allows certain hardware subsystems to access main system memory independently of the central processing unit (CPU).

<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">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.

<span class="mw-page-title-main">Low Pin Count</span> Low-bandwidth computer motherboard bus

The Low Pin Count (LPC) bus is a computer bus used on IBM-compatible personal computers to connect low-bandwidth devices to the CPU, such as the BIOS ROM, "legacy" I/O devices, and Trusted Platform Module (TPM). "Legacy" I/O devices usually include serial and parallel ports, PS/2 keyboard, PS/2 mouse, and floppy disk controller.

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">Isoflavonoid</span>

Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estrogen receptor.

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

Ipriflavone is a synthetic isoflavone which may be used to inhibit bone resorption, maintain bone density and to prevent osteoporosis in postmenopausal women. It is not used to treat osteoporosis. It slows down the action of the osteoclasts, possibly allowing the osteoblasts to build up bone mass.

<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">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">Femarelle</span> Trademarked mixture

Femarelle is a dietary supplement that is a mixture of DT56a and flaxseed powder, that may act as a selective estrogen receptor modulator (SERM). In 2008 an application was submitted to the European Food Safety Authority to market Femarelle with a health claim, namely that it can reduce the risk for osteoporosis and other bone disorders; the EFSA found that "the food/constituent for which the claim is made, i.e. Femarelle, has not been sufficiently characterised" and that " a cause and effect relationship has not been established between the consumption of Femarelle and increased BMD, increased bone formation, or decreased risk of osteoporosis or other bone disorders in post-menopausal women."

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

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. However, more recent studies have suggested that the active ingredient may actually be the closely related chemical compound deoxymiroestrol, and the reported presence of miroestrol may only have been an artifact of the isolation procedure. When deoxymiroestrol is exposed to the oxygen in air, it is converted to miroestrol.

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

Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea and in other legumes.

The molecular formula C15H14O4 may refer to:

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

Isoflavanes are a class of isoflavonoids, which are themselves types of polyphenolic compounds. They have the 3-phenylchroman (isoflavan, CAS number: 4737-26-2, molecular formula: C15H14O, exact mass: 210.1044646 u) backbone.

Adlercreutzia is a genus in the phylum Actinomycetota (Bacteria).

<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">Nonsteroidal estrogen</span> Class of drugs

A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used. On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES, and these drugs remain widely used in medicine for the treatment of breast cancer among other indications. In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity.

<span class="mw-page-title-main">DMA's</span> Australian band

DMA's are an Australian three-piece rock band formed in 2012 in Sydney. The band is composed of Tommy O'Dell, Matt Mason, and Johnny Took. They gained popularity for their debut single "Delete" and for their self-titled EP released in 2014. The band's moniker comes from their former name, "The Dirty MA's".

<i>Soy boy</i> Pejorative term for men perceived as non-masculine

Soy boy is a pejorative term sometimes used in online communities to describe men perceived to be lacking masculine characteristics. The term bears many similarities and has been compared to the slang terms cuck, nu-male and low-T – terms sometimes used as an insult for male femininity by online communities.

References

  1. 1 2 3 Frankenfeld, C. L. (2011). "O-Desmethylangolensin: The Importance of Equol's Lesser Known Cousin to Human Health". Advances in Nutrition. 2 (4): 317–324. doi:10.3945/an.111.000539. PMC   3125681 . PMID   22332073.