Lipophilic oestrogen derivatives contained in lipoprotein particles.
Steroid fatty acid esters constitute a unique family of lipophilic hormones carried exclusively in circulating lipoproteins. Our studies have focused on the formation of 17beta fatty acid esters of labelled oestradiol in in vitro incubations with human ovarian follicular fluid and plasma and demonstrated the accumulation of these labelled derivatives in lipoprotein particles. The oestradiol esters are formed in a reaction catalysed by lecithin : cholesterol acyltransferase in association with high-density lipoprotein particles and they can be transferred to low-density lipoprotein particles in a process mediated by cholesteryl ester transfer protein. Using a novel quantitative method for the determination of oestradiol esters their endogenous concentrations in follicular fluid and in early and late pregnancy plasma have been determined. In addition, using labelled genistein and its chemically synthesized fatty acid esters, we also demonstrated that phytoestrogen derivatives could be incorporated in lipoprotein particles. Both oestradiol and genistein contain aromatic hydroxyl groups which cause them to exert powerful antioxidant activity in lipid-aqueous systems in vitro. The physiological role of the steroidal fatty acid esters remains to be elucidated. In theory, the hormonal esters might form a reservoir constituted by esterified hormones stored in lipoprotein particles and perhaps in fat tissue, or they might use lipoproteins as vehicles for endocrine transport, or they could act as antioxidant protection of the lipoprotein particles. Enzyme systems necessary for the formation of lipophilic oestrogen and phytoestrogen derivatives as well as for their incorporation in lipoprotein particles are present in human body fluids. Because of their water-insolubility, steroid fatty acid esters are carried exclusively by circulating lipoproteins. These esters can provide antioxidant protection for lipoprotein particles.
D002845:Chromatography; D004952:Esters / Q000378:metabolism; D004958:Estradiol / Q000378:metabolism; D004967:Estrogens / Q000378:metabolism*; D004968:Estrogens, Non-Steroidal / Q000378:metabolism; D005227:Fatty Acids / Q000378:metabolism / Q000502:physiology*; D005260:Female; D015571:Follicular Fluid / Q000378:metabolism*; D019833:Genistein / Q000378:metabolism; D006801:Humans; D007529:Isoflavones; D008074:Lipoproteins / Q000737:chemistry / Q000378:metabolism*; D008075:Lipoproteins, HDL / Q000378:metabolism; D008077:Lipoproteins, LDL / Q000378:metabolism; D008079:Lipoproteins, VLDL / Q000378:metabolism; D048789:Phytoestrogens; D028321:Plant Preparations; D011247:Pregnancy
D004952:Esters; D004967:Estrogens; D004968:Estrogens, Non-Steroidal; D005227:Fatty Acids; D007529:Isoflavones; D008074:Lipoproteins; D008075:Lipoproteins, HDL; D008077:Lipoproteins, LDL; D008079:Lipoproteins, VLDL; D048789:Phytoestrogens; D028321:Plant Preparations; D004958:Estradiol; D019833:Genistein