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Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Agric. Food Chem. 2013, 61, 31, 7654-7660
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Hypaphorine Is Present in Human Milk in Association with Consumption of Legumes

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† Department of Pathology and Laboratory Medicine, University of British Columbia, Child & Family Research Institute, Nutrition and Metabolism, Vancouver, BC, V5Z 4H4, Canada
‡ Department of Pediatrics, University of British Columbia, Child & Family Research Institute, Nutrition and Metabolism, Vancouver, BC, V5Z 4H4, Canada
§ Department of Chemistry, University of British Columbia, Vancouver, BC, V6T 1Z1, Canada
*Phone: +1-604-875-2000 ext 5480. E-mail: [email protected]
Cite this: J. Agric. Food Chem. 2013, 61, 31, 7654–7660
Publication Date (Web):July 16, 2013
https://doi.org/10.1021/jf401758f
Copyright © 2013 American Chemical Society
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Abstract

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In metabolomic analysis of human milk amines, we found a previously unidentified compound. This was tentatively identified as hypaphorine, an indole alkaloid composed of tryptophan and three methyls, and with neurological and glucose-lowering effects in rodents. Hypaphorine identity was confirmed by hypaphorine synthesis, and then a fluorometric method was developed to quantify hypaphorine in milk and foods. Using dietary records, we identified peanut products as probable sources of hypaphorine. Milk from 24 lactating women showed widely varying hypaphorine, with a mean ± SD 0.34 ± 0.33 μM, and the highest concentration of 1.24 μM. Peanuts showed high hypaphorine of 70 μg/g compared to 60 and 100 μg/g in dried chickpeas and lentils. Dietary challenge in lactating women with hypaphorine-rich foods demonstrated transfer of hypaphorine into milk with hypaphorine appearance peaking 5–18 h after consumption and prolonged disappearance indicative of slow excretion or metabolism. The potential functional roles of hypaphorine in human nutrition remain to be addressed.

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Copies of original NMR scans for hypaphorine, calibration curves for fluorometric tryptophan and hypaphorine determination, fluorogram and mass spectra for synthesized hypaphorine, time courses of free hypaphorine concentration in human milk from 2 more volunteers after a dietary intervention, and details of the employed HPLC–MS gradient program. This material is available free of charge via the Internet at http://pubs.acs.org.

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This article is cited by 18 publications.

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