Mammalian phytoestrogens: enterodiol and enterolactone.
The mammalian phytoestrogens enterodiol (END) and enterolactone (ENL) are produced in the colon by the action of bacteria on the plant precursors matairesinol (MAT), secoisolariciresinol (SECO), their glycosides, and other precursors in the diet. Both END and ENL have been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of these antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men. Various in vitro experiments suggested END and ENL significantly inhibited the growth of human colon tumor cells, and the E2-induced proliferation of MCF-7 breast cancer cells was inhibited by ENL. The protective effects of mammalian lignans may be due to their ability to compete with E2 for the type II estrogen receptor, to induce sex hormone binding globulin (SHBG), to inhibit placental aromatase, and to act as antioxidants. This review mainly deals with the chemistry, quantitative analysis, biological properties and health effects of END and ENL.
Wang
Li-Quan
LQ
Department of Medicinal Chemistry, College of Pharmacy, University of Florida, PO Box 100485, 1600 SW Archer Road, Gainesville, FL 32610, USA. 1qwang@ufl.edu
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000378:metabolism / Q000494:pharmacology / Q000502:physiology*; D005260:Female; D006801:Humans; D017705:Lignans / Q000096:biosynthesis / Q000378:metabolism* / Q000494:pharmacology; D008297:Male; D014407:Tumor Cells, Cultured
D017705:Lignans; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone