Enterolactone
title: "Enterolactone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["lignans", "tetrahydrofurans", "furanones", "phytoestrogens", "diols", "3-hydroxyphenyl-compounds"] topic_path: "general/lignans" source: "https://en.wikipedia.org/wiki/Enterolactone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| Watchedfields = changed | verifiedrevid = 423619705 | ImageFile=Enterolactone.png | ImageSize=180px | PIN=(3R,4R)-3,4-Bis[(4-hydroxyphenyl)methyl]oxolan-2-one | OtherNames=(−)-Enterolactone |Section1={{Chembox Identifiers | Abbreviations = ENL | CASNo_Ref = | CASNo=78473-71-9 | ChEMBL = 471475 | ChemSpiderID = 8860823 | EC_number = 634-756-3 | UNII_Ref = | UNII = X01E7E1D6H | KEGG_Ref = | KEGG = C18165 | PubChem=10685477 | StdInChI=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 | StdInChIKey = HVDGDHBAMCBBLR-WMLDXEAASA-N | SMILES=C1C@@HCC3=CC(=CC=C3)O |Section2={{Chembox Properties | C=18 | H=18 | O=4 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | GHS_ref=https://pubchem.ncbi.nlm.nih.gov/compound/10685477#section=Safety-and-Hazards | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases = | MainHazards= | FlashPt= | AutoignitionPt =
Enterolactone is an organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.
Sources
Many dietary plant lignan precursors, such as secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, and sesamin, can be metabolized by gut microbes to enterolactone.{{Cite journal | pmid = 11453749 | year = 2001 | last1 = Heinonen | first1 = S | title = In vitro metabolism of plant lignans: New precursors of mammalian lignans enterolactone and enterodiol | journal = Journal of Agricultural and Food Chemistry | volume = 49 | issue = 7 | pages = 3178–86 | last2 = Nurmi | first2 = T | last3 = Liukkonen | first3 = K | last4 = Poutanen | first4 = K | last5 = Wähälä | first5 = K | last6 = Deyama | first6 = T | last7 = Nishibe | first7 = S | last8 = Adlercreutz | first8 = H | doi=10.1021/jf010038a | bibcode = 2001JAFC...49.3178H | pmid = 15877880 | year = 2005 | last1 = Milder | first1 = I. E. | title = Lignan contents of Dutch plant foods: A database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol | journal = The British Journal of Nutrition | volume = 93 | issue = 3 | pages = 393–402 | last2 = Arts | first2 = I. C. | last3 = Van De Putte | first3 = B | last4 = Venema | first4 = D. P. | last5 = Hollman | first5 = P. C. | doi=10.1079/bjn20051371 | doi-access = free | pmid = 16898863 | year = 2006 | last1 = Thompson | first1 = L. U. | title = Phytoestrogen content of foods consumed in Canada, including isoflavones, lignans, and coumestan | journal = Nutrition and Cancer | volume = 54 | issue = 2 | pages = 184–201 | last2 = Boucher | first2 = B. A. | last3 = Liu | first3 = Z | last4 = Cotterchio | first4 = M | last5 = Kreiger | first5 = N | doi = 10.1207/s15327914nc5402_5 | s2cid = 60328 | pmid = 17261017 | year = 2007 | last1 = Smeds | first1 = A. I. | title = Quantification of a broad spectrum of lignans in cereals, oilseeds, and nuts | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 4 | pages = 1337–46 | last2 = Eklund | first2 = P. C. | last3 = Sjöholm | first3 = R. E. | last4 = Willför | first4 = S. M. | last5 = Nishibe | first5 = S | last6 = Deyama | first6 = T | last7 = Holmbom | first7 = B. R. | doi = 10.1021/jf0629134 | bibcode = 2007JAFC...55.1337S | pmid = 19079885 | year = 2006 | last1 = Clavel | first1 = T | title = Bioavailability of lignans in human subjects | journal = Nutrition Research Reviews | volume = 19 | issue = 2 | pages = 187–96 | last2 = Doré | first2 = J | last3 = Blaut | first3 = M | doi = 10.1017/S0954422407249704 | doi-access = free | pmid = 6113409 | year = 1981 | last1 = Setchell | first1 = K. D. | title = Lignan formation in man--microbial involvement and possible roles in relation to cancer | journal = Lancet | volume = 2 | issue = 8236 | pages = 4–7 | last2 = Lawson | first2 = A. M. | last3 = Borriello | first3 = S. P. | last4 = Harkness | first4 = R | last5 = Gordon | first5 = H | last6 = Morgan | first6 = D. M. | last7 = Kirk | first7 = D. N. | last8 = Adlercreatz | first8 = H | last9 = Anderson | first9 = L. C. | last10 = Axelson | first10 = M | doi=10.1016/s0140-6736(81)90250-6 | s2cid = 39049097 | pmid = 11867359 | year = 2002 | last1 = Kilkkinen | first1 = A | title = Use of oral antimicrobials decreases serum enterolactone concentration | journal = American Journal of Epidemiology | volume = 155 | issue = 5 | pages = 472–7 | last2 = Pietinen | first2 = P | last3 = Klaukka | first3 = T | last4 = Virtamo | first4 = J | last5 = Korhonen | first5 = P | last6 = Adlercreutz | first6 = H | doi=10.1093/aje/155.5.472 | doi-access = free
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.{{Cite journal | pmid = 17943494 | year = 2007 | last1 = Adlercreutz | first1 = H | title = Lignans and human health | journal = Critical Reviews in Clinical Laboratory Sciences | volume = 44 | issue = 5–6 | pages = 483–525 | doi = 10.1080/10408360701612942 | s2cid = 31753060 | pmid = 20883417 | pmc = 2951311 | year = 2010 | last1 = Peterson | first1 = J | title = Dietary lignans: Physiology and potential for cardiovascular disease risk reduction | journal = Nutrition Reviews | volume = 68 | issue = 10 | pages = 571–603 | last2 = Dwyer | first2 = J | last3 = Adlercreutz | first3 = H | last4 = Scalbert | first4 = A | last5 = Jacques | first5 = P | last6 = McCullough | first6 = M. L. | doi = 10.1111/j.1753-4887.2010.00319.x
References
References
- Lampe JW. (2003). "Isoflavonoid and lignan phytoestrogens as dietary biomarkers". J Nutr.
- (May 2005). "Dietary sesamin is converted to enterolactone in humans". J. Nutr..
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