Enterodiol

Last updated
Enterodiol
Enterodiol.png
Names
Preferred IUPAC name
(2R,3R)-2,3-Bis[(3-hydroxyphenyl)methyl]butane-1,4-diol
Other names
(−)-Enterodiol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.162.704 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1 X mark.svgN
    Key: DWONJCNDULPHLV-HOTGVXAUSA-N X mark.svgN
  • InChI=1/C18H22O4/c19-11-15(7-13-3-1-5-17(21)9-13)16(12-20)8-14-4-2-6-18(22)10-14/h1-6,9-10,15-16,19-22H,7-8,11-12H2/t15-,16-/m0/s1
    Key: DWONJCNDULPHLV-HOTGVXAUBO
  • C1=CC(=CC(=C1)O)C[C@@H](CO)[C@@H](CC2=CC(=CC=C2)O)CO
Properties
C18H22O4
Molar mass 302.370 g·mol−1
Appearancecolorless
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Enterodiol is an organic compound with the formula [HOC6H4CH2CH(CH2OH)]2.

It is formed by the action of intestinal bacteria on lignan precursors. As such it is sometimes classified as a enterolignan or mammalian lignan. [1] [2] Elevated levels of enterodiol in urine are attributed consumption of tea and other lignan-rich foods. [3]

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<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.

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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.

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.

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">Secoisolariciresinol</span> Chemical compound

Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, e.g. rye, and together with matairesinol, has attracted much attention for its beneficial nutritional effects.

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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.

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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.

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Enterolignans are organic compounds formed by the action of gut microflora on lignans. They are thus the products of the combined action of both plants and of the animal gut. Prominent enterolignans are enterodiol and enterolactone. Enterolignans are also called "mammalian lignans", although that term is self-contradictory since mammals do not produce lignans.

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

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References

  1. Adlercreutz, Herman (2007). "Lignans and Human Health". Critical Reviews in Clinical Laboratory Sciences. 44 (5–6): 483–525. doi:10.1080/10408360701612942. PMID   17943494. S2CID   31753060.
  2. Lampe JW (2003). "Isoflavonoid and lignan phytoestrogens as dietary biomarkers". J Nutr. 133 (Suppl 3): 956S–964S. doi: 10.1093/jn/133.3.956S . PMID   12612182.
  3. Adlercreutz, H.; Honjo, H.; Higashi, A.; Fotsis, T.; Hämäläinen, E.; Hasegawa, T.; Okada, H. (1991). "Urinary excretion of lignans and isoflavonoid phytoestrogens in Japanese men and women consuming a traditional Japanese Diet". The American Journal of Clinical Nutrition. 54 (6): 1093–1100. doi: 10.1093/ajcn/54.6.1093 . PMID   1659780.