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
  • 78473-71-9 Yes check.svgY
3D model (JSmol)
AbbreviationsENL
ECHA InfoCard 100.162.708 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
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

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

A nutrient is a substance used by an organism to survive, grow, and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi, and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures, such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted to smaller molecules in the process of releasing energy, such as for carbohydrates, lipids, proteins, and fermentation products, leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.

Inulin Chemical compound

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 the United States in 2018, the 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.

Phytoestrogen

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.

Secoisolariciresinol diglucoside Antioxidant[1] phytoestrogen present in flax, sunflower, sesame, and pumpkin seeds. In food, it can be found in commercial breads containing flaxseed

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.

Equol Isoflavandiol estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines

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. However, only about 30–50% of people have intestinal bacteria that make equol. Equol can exist in two enantiomeric forms, (S)-equol and (R)-equol. (S)-Equol preferentially binds estrogen receptor beta.

Prebiotics are compounds in food that induce the growth or activity of beneficial microorganisms such as bacteria and fungi. The most common example is in 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.

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).

Alkylresorcinols, also known as resorcinolic lipids, are phenolic lipids composed of long aliphatic chains and resorcinol-type phenolic rings.

Secoisolariciresinol 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.

Podophyllotoxin

Podophyllotoxin (PPT) is the active ingredient in Podofilox, which is a medical cream that is used to treat genital warts and molluscum contagiosum. It is not recommended in HPV infections without external warts. It can be applied either by a healthcare provider or the person themselves.

Diet and cancer Connections between dietary habits and cancer

Dietary factors are recognized as having a significant effect on the risk of cancers, with different dietary elements both increasing and reducing risk. Diet and obesity may be related to up to 30-35% of cancer deaths, while physical inactivity appears to be related to 7% risk of cancer occurrence. One review in 2011 suggested that total caloric intake influences cancer incidence and possibly progression.

Matairesinol 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, e.g. rye, and together with Secoisolariciresinol, has attracted much attention for its beneficial nutritional effects.

Sesamin 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, although no controlled studies on this application have been performed. 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.

Lariciresinol 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.

Enterolignan

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.

Enterodiol 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.

Pinoresinol Chemical compound

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

Hydroxymatairesinol Chemical compound

Hydroxymatairesinol (HMR) is a lignan found in Norway spruce. It is an enterolactone precursor with anticancer activities. In rats, HMR decreased the volume of induced tumours and stabilised established tumours, as well as preventing the development of new tumours. It has also shown anti-oxidant properties in vitro.

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.
  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.
  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.
  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.