Enterolactone

Last updated
Enterolactone
Enterolactone.png
Names
Preferred IUPAC name
(3R,4R)-3,4-Bis[(4-hydroxyphenyl)methyl]oxolan-2-one
Other names
(−)-Enterolactone
Identifiers
3D model (JSmol)
AbbreviationsENL
ChEMBL
ChemSpider
ECHA InfoCard 100.162.708 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 634-756-3
KEGG
PubChem CID
UNII
  • InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m0/s1
    Key: HVDGDHBAMCBBLR-WMLDXEAASA-N
  • C1[C@@H]([C@H](C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O
Properties
C18H18O4
Molar mass 298.338 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Enterolactone is a organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

Contents

Sources

Many dietary plant lignan precursors, such as secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, and sesamin, can be metabolized by gut microbes to enterolactone. [1] [2] [3] In edible plants lignans are bound to the fiber fraction and therefore fiber-rich food products, such as cereals, vegetables, fruits and berries, are generally good sources of lignans and enterolactone. The richest known dietary sources of enterolactone precursors are flaxseed and sesame seed. [4] [5] [6] Since enterolactone is produced by specific species of gut microbiota, the capacity to produce it varies between people. [7] Antibiotic treatments can abolish the capacity to produce enterolactone. It may take up to a year before enterolactone production is restored. [8] [9]

Health effects

Enterolactone is suggested to possess beneficial health effects in humans. In epidemiological studies lower concentrations of enterolactone have been observed in breast cancer patients compared to healthy controls, which may suggest that enterolactone is anti-carcinogenic. Enterolactone and lignans may also be protective against cardiovascular disease. [10] [11]

Related Research Articles

Tocopherols are a class of organic compounds comprising various methylated phenols, many of which have vitamin E activity. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was named tocopherol, from Greek τόκοςtókos 'birth' and φέρεινphérein 'to bear or carry', that is 'to carry a pregnancy', with the ending -ol signifying its status as a chemical alcohol.

<span class="mw-page-title-main">Soybean</span> Legume grown for its edible bean

The soybean, soy bean, or soya bean is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses.

<span class="mw-page-title-main">Polyphenol</span> Class of chemical compounds

Polyphenols are a large family of naturally occurring phenols. They are abundant in plants and structurally diverse. Polyphenols include phenolic acids, flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and for tanning garments.

<span class="mw-page-title-main">Inulin</span> Natural plant polysaccharides

Inulins are a group of naturally occurring polysaccharides produced by many types of plants, industrially most often extracted from chicory. The inulins belong to a class of dietary fibers known as fructans. Inulin is used by some plants as a means of storing energy and is typically found in roots or rhizomes. Most plants that synthesize and store inulin do not store other forms of carbohydrate such as starch. In 2018, the United States Food and Drug Administration approved inulin as a dietary fiber ingredient used to improve the nutritional value of manufactured food products. Using inulin to measure kidney function is the "gold standard" for comparison with other means of estimating glomerular filtration rate.

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

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.

<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">Vegetarian nutrition</span> Nutritional and human health aspects of vegetarian diets

Vegetarian nutrition is the set of health-related challenges and advantages of vegetarian diets.

<span class="mw-page-title-main">Secoisolariciresinol diglucoside</span> Antioxidant phytoestrogen

Secoisolariciresinol diglucoside (SDG) is an antioxidant phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed. It is a precursor of mammal lignans which are produced in the colon from chemicals in foods.

<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.

Prebiotics are compounds in food that foster growth or activity of beneficial microorganisms such as bacteria and fungi. The most common environment concerning their effects on human health is the gastrointestinal tract, where prebiotics can alter the composition of organisms in the gut microbiome.

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.

<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, such as rye, and together with matairesinol has attracted much attention for its beneficial nutritional effects.

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

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

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

Sesamin is a lignan isolated from the bark of Fagara plants and from sesame oil. It has been used as a dietary fat-reduction supplement. Its major metabolite is enterolactone, which has an elimination half life of less than 6 hours. Sesamin and sesamolin are minor components of sesame oil, on average comprising only 0.14% of the oil by mass.

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

Lariciresinol is a lignan, i.e., a type of phenylpropanoids. It is the precursor to enterolignans by the action of gut microflora. Enterolignans are of interest because they are speculated to exhibit beneficial medicinal properties.

<span class="mw-page-title-main">Enterolignan</span> Class of chemical compounds

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.

<span class="mw-page-title-main">Enterodiol</span> Lignan formed by the action of intestinal bacteria on lignan precursors found in plants.[1]

Enterodiol is an organic compound with the formula [HOC6H4CH2CH(CH2OH)]2.

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

Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

References

  1. 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.
  2. Peñalvo JL, Heinonen SM, Aura AM, Adlercreutz H (May 2005). "Dietary sesamin is converted to enterolactone in humans". J. Nutr. 135 (5): 1056–1062. doi: 10.1093/jn/135.5.1056 . PMID   15867281.
  3. Heinonen, S; Nurmi, T; Liukkonen, K; Poutanen, K; Wähälä, K; Deyama, T; Nishibe, S; Adlercreutz, H (2001). "In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol". Journal of Agricultural and Food Chemistry. 49 (7): 3178–86. doi:10.1021/jf010038a. PMID   11453749.
  4. Milder, I. E.; Arts, I. C.; Van De Putte, B; Venema, D. P.; Hollman, P. C. (2005). "Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol". The British Journal of Nutrition. 93 (3): 393–402. doi: 10.1079/bjn20051371 . PMID   15877880.
  5. Thompson, L. U.; Boucher, B. A.; Liu, Z; Cotterchio, M; Kreiger, N (2006). "Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan". Nutrition and Cancer. 54 (2): 184–201. doi:10.1207/s15327914nc5402_5. PMID   16898863. S2CID   60328.
  6. Smeds, A. I.; Eklund, P. C.; Sjöholm, R. E.; Willför, S. M.; Nishibe, S; Deyama, T; Holmbom, B. R. (2007). "Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts". Journal of Agricultural and Food Chemistry. 55 (4): 1337–46. doi:10.1021/jf0629134. PMID   17261017.
  7. Clavel, T; Doré, J; Blaut, M (2006). "Bioavailability of lignans in human subjects". Nutrition Research Reviews. 19 (2): 187–96. doi: 10.1017/S0954422407249704 . PMID   19079885.
  8. Setchell, K. D.; Lawson, A. M.; Borriello, S. P.; Harkness, R; Gordon, H; Morgan, D. M.; Kirk, D. N.; Adlercreatz, H; Anderson, L. C.; Axelson, M (1981). "Lignan formation in man--microbial involvement and possible roles in relation to cancer". Lancet. 2 (8236): 4–7. doi:10.1016/s0140-6736(81)90250-6. PMID   6113409. S2CID   39049097.
  9. Kilkkinen, A; Pietinen, P; Klaukka, T; Virtamo, J; Korhonen, P; Adlercreutz, H (2002). "Use of oral antimicrobials decreases serum enterolactone concentration". American Journal of Epidemiology. 155 (5): 472–7. doi: 10.1093/aje/155.5.472 . PMID   11867359.
  10. Adlercreutz, H (2007). "Lignans and human health". Critical Reviews in Clinical Laboratory Sciences. 44 (5–6): 483–525. doi:10.1080/10408360701612942. PMID   17943494. S2CID   31753060.
  11. Peterson, J; Dwyer, J; Adlercreutz, H; Scalbert, A; Jacques, P; McCullough, M. L. (2010). "Dietary lignans: Physiology and potential for cardiovascular disease risk reduction". Nutrition Reviews. 68 (10): 571–603. doi:10.1111/j.1753-4887.2010.00319.x. PMC   2951311 . PMID   20883417.