Enterolactone
IUPAC 名称
(3R,4R)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one
描述
Production of intestinal flora acting on lignans present in cereal
Enterolactone is a mammalian lignan that have a similar biphenolic structure to lignans from plants. Lignans are compounds with estrogenic properties and are probably the most important source of phytoestrogens in western diets. Mammalian lignans are formed from precursors that are contained mainly in vegetables, whole grain products and berries, via action of intestinal microflora. Enterolactone is produced in the colon by the action of bacteria on secoisolariciresinol, matairesinol and its glycosides. Secoisolariciresinol is converted to enterodiol which is subsequently converted to enterolactone as it passes through the colon. Matairesinol is converted directly to enterolactone. Enterolactone have been shown to possess weakly estrogenic and antiestrogenic activities, and it has been suggested that the high production of this antiestrogenic mammalian lignans in the gut may serve to protect against breast cancer in women and prostate cancer in men; however epidemiological evidence to date is conflicting. (PMID: 16168401, 12270221, 11216511, 12107024). Enterolactone is a biomarker for the consumption of soy beans and other soy products. Enterolactone is found in cereals and cereal products.
异构
OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC=C2)=C1
InChI标识符
InChI=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
键
HVDGDHBAMCBBLR-WMLDXEAASA-N