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.
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 effectsedit
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]
Referencesedit
^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.
^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.
^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.
^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.
^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.
^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.
^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.
^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.
^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.
^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.
^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. PMC2951311. PMID 20883417.
April 11, 2024
enterolactone, organic, compound, classified, enterolignan, formed, action, intestinal, bacteria, plant, lignan, precursors, present, diet, namespreferred, iupac, name, hydroxyphenyl, methyl, oxolan, oneother, names, identifierscas, number, 78473, model, jsmol. 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 Enterolactone NamesPreferred IUPAC name 3R 4R 3 4 Bis 4 hydroxyphenyl methyl oxolan 2 oneOther names EnterolactoneIdentifiersCAS Number 78473 71 9 Y3D model JSmol Interactive imageAbbreviations ENLECHA InfoCard 100 162 708KEGG C18165 YPubChem CID 10685477UNII X01E7E1D6H YCompTox Dashboard EPA DTXSID0048183SMILES C1 C H C H C O O1 CC2 CC CC C2 O CC3 CC CC C3 OPropertiesChemical formula C 18H 18O 4Molar mass 298 338 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox referencesSources editMany 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 editEnterolactone 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 References edit 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 Penalvo 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 Heinonen S Nurmi T Liukkonen K Poutanen K Wahala 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 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 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 Smeds A I Eklund P C Sjoholm R E Willfor 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 Clavel T Dore J Blaut M 2006 Bioavailability of lignans in human subjects Nutrition Research Reviews 19 2 187 96 doi 10 1017 S0954422407249704 PMID 19079885 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 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 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 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 Retrieved from https en wikipedia org w index php title Enterolactone amp oldid 1129816914, wikipedia, wiki, book, books, library,
