Identification of lignans and phytoestrogens in urine of chimpanzees.
It was recently observed that the urinary excretion of animal lignans is low in postmenopausal breast cancer patients compared to normal omnivorous and vegetarian women. In addition, the mean excretion of the isoflavonic phytoestrogen equol tended to be lower. Because nonhuman primates appear to be remarkably resistant to the carcinogenic effect of estrogens, we investigated the possible occurrence of lignans and phytoestrogens in the urine of chimpanzees on their regular diet. Five major diphenols were isolated and identified by capillary gas chromatography and mass spectrometry by comparison with synthesized authentic reference compounds. Three of these compounds, the phytoestrogen equol and its precursor daidzein, the lignan enterolactone, were according to preliminary assays excreted in very large amounts. In addition, the lignan enterodiol and the daidzein metabolite O-desmethylangolensin were identified. It is concluded that the chimpanzee excretes both isoflavonic phytoestrogens and lignans in urine, apparently in high concentrations. It is suggested that these compounds may play a role in the maintenance of the resistance against carcinogenic effects of estrogens, which nonhuman primates possess, because both equol and enterolactone have been shown to have antiestrogenic properties in animals. However, much further work is necessary before the possible biological role of these compounds may be established.
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000652:urine; D000818:Animals; D002072:Butylene Glycols / Q000652:urine; D002839:Chromans / Q000652:urine; D004032:Diet; D060754:Equol; D004967:Estrogens / Q000652:urine*; D004968:Estrogens, Non-Steroidal; D007529:Isoflavones / Q000652:urine; D017705:Lignans; D008297:Male; D002679:Pan troglodytes / Q000652:urine*; D048789:Phytoestrogens; D010936:Plant Extracts / Q000652:urine*; D028321:Plant Preparations
C007610:4',7-dihydroxy-3,4-dihydroisoflavone; D002072:Butylene Glycols; D002839:Chromans; D004967:Estrogens; D004968:Estrogens, Non-Steroidal; D007529:Isoflavones; D017705:Lignans; D048789:Phytoestrogens; D010936:Plant Extracts; D028321:Plant Preparations; D060754:Equol; C004742:daidzein; C029498:2,3-bis(3'-hydroxybenzyl)butane-1,4-diol; D015107:4-Butyrolactone; C050052:O-desmethylangolensin; C029497:2,3-bis(3'-hydroxybenzyl)butyrolactone