Enterolactone
{{chembox
| 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 = {{cascite|correct|??}}
| CASNo=78473-71-9
| ChEMBL = 471475
| ChemSpiderID = 8860823
| EC_number = 634-756-3
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X01E7E1D6H
| KEGG_Ref = {{keggcite|correct|kegg}}
| 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=C1[C@@H]([C@H](C(=O)O1)CC2=CC(=CC=C2)O)CC3=CC(=CC=C3)O
}}
|Section2={{Chembox Properties
| C=18 | H=18 | O=4
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
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|Section3={{Chembox Hazards
| GHS_ref=[https://pubchem.ncbi.nlm.nih.gov/compound/10685477#section=Safety-and-Hazards]
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|264|264+265|271|280|302+352|304+340|305+351+338|319|321|332+317|337+317|362+364|403+233|405|501}}
| MainHazards=
| FlashPt=
| AutoignitionPt =
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}}
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 | author = Lampe JW | title = Isoflavonoid and lignan phytoestrogens as dietary biomarkers | journal = J Nutr | year = 2003 | volume = 133 | issue = Suppl 3 | pages = 956S–964S | pmid = 12612182| doi = 10.1093/jn/133.3.956S | doi-access = free }}{{cite journal |vauthors=Peñalvo JL, Heinonen SM, Aura AM, Adlercreutz H |title=Dietary sesamin is converted to enterolactone in humans |journal=J. Nutr. |volume=135 |issue=5 |pages=1056–1062 |date=May 2005 |pmid=15867281 |url=http://jn.nutrition.org/content/135/5/1056.long |doi=10.1093/jn/135.5.1056 |doi-access=free }}{{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
}} 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.{{Cite journal
| 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
}} Since enterolactone is produced by specific species of gut microbiota, the capacity to produce it varies between people.{{Cite journal
| 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
}} Antibiotic treatments can abolish the capacity to produce enterolactone. It may take up to a year before enterolactone production is restored.{{Cite journal
| 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
}}