ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
Recently Viewed
You have not visited any articles yet, Please visit some articles to see contents here.
CONTENT TYPES

Figure 1Loading Img

Hypaphorine Is Present in Human Milk in Association with Consumption of Legumes

View Author Information
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
Article Views
600
Altmetric
-
Citations
LEARN ABOUT THESE METRICS
Read OnlinePDF (714 KB)
Supporting Info (1)»

Abstract

Abstract Image

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.

Supporting Information

ARTICLE SECTIONS
Jump To

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.

Terms & Conditions

Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

Cited By


This article is cited by 18 publications.

  1. Alessandra Olarini, Madeleine Ernst, Gözde Gürdeniz, Min Kim, Nicklas Brustad, Klaus Bønnelykke, Arieh Cohen, David Hougaard, Jessica Lasky-Su, Hans Bisgaard, Bo Chawes, Morten Arendt Rasmussen. Vertical Transfer of Metabolites Detectable from Newborn’s Dried Blood Spot Samples Using UPLC-MS: A Chemometric Study. Metabolites 2022, 12 (2) , 94. https://doi.org/10.3390/metabo12020094
  2. Yu‐Hua Ding, Run‐Xin Miao, Qiang Zhang. Hypaphorine exerts anti‐inflammatory effects in sepsis induced acute lung injury via modulating DUSP1 /p38/ JNK pathway. The Kaohsiung Journal of Medical Sciences 2021, 37 (10) , 883-893. https://doi.org/10.1002/kjm2.12418
  3. Murilo K.A. Yonekawa, Bruna de B. Penteado, Amanda Dal'Ongaro Rodrigues, Estela M.G. Lourenço, Euzébio G. Barbosa, Silvia C. das Neves, Rodrigo J. de Oliveira, Maria R. Marques, Denise B. Silva, Dênis P. de Lima, Adilson Beatriz, Jean P. Oses, Jeandre A. dos S. Jaques, Edson dos A. dos Santos. l-Hypaphorine and d-hypaphorine: Specific antiacetylcholinesterase activity in rat brain tissue. Bioorganic & Medicinal Chemistry Letters 2021, 47 , 128206. https://doi.org/10.1016/j.bmcl.2021.128206
  4. Robert Ringseis, Sarah M. Grundmann, Sven Schuchardt, Erika Most, Klaus Eder. Limited Impact of Pivalate-Induced Secondary Carnitine Deficiency on Hepatic Transcriptome and Hepatic and Plasma Metabolome in Nursery Pigs. Metabolites 2021, 11 (9) , 573. https://doi.org/10.3390/metabo11090573
  5. Mar Garcia‐Aloy, Marynka Ulaszewska, Pietro Franceschi, Sheila Estruel‐Amades, Christoph H. Weinert, Alba Tor‐Roca, Mireia Urpi‐Sarda, Fulvio Mattivi, Cristina Andres‐Lacueva. Discovery of Intake Biomarkers of Lentils, Chickpeas, and White Beans by Untargeted LC–MS Metabolomics in Serum and Urine. Molecular Nutrition & Food Research 2020, 64 (13) , 1901137. https://doi.org/10.1002/mnfr.201901137
  6. Victoria Meslier, Manolo Laiola, Henrik Munch Roager, Francesca De Filippis, Hugo Roume, Benoit Quinquis, Rosalba Giacco, Ilario Mennella, Rosalia Ferracane, Nicolas Pons, Edoardo Pasolli, Angela Rivellese, Lars Ove Dragsted, Paola Vitaglione, Stanislav Dusko Ehrlich, Danilo Ercolini. Mediterranean diet intervention in overweight and obese subjects lowers plasma cholesterol and causes changes in the gut microbiome and metabolome independently of energy intake. Gut 2020, 69 (7) , 1258-1268. https://doi.org/10.1136/gutjnl-2019-320438
  7. Emmanuel Talla, Marthe Carine Djuidje Fotsing, Musa Bunu Ismaila, Charlotte Mungho Tata, Monisola Itohan Ikhile, Lydia Rhyman, Charmaine Arderne, Nicolette Niemann, Ponnadurai Ramasami, Derek Tantoh Ndinteh. Density functional theory studies of Hypaphorine from Erythrina mildbraedii and Erythrina addisoniae: structural and biological properties. SN Applied Sciences 2020, 2 (3) https://doi.org/10.1007/s42452-020-2228-z
  8. Mar Garcia-Aloy, Paul J. M. Hulshof, Sheila Estruel-Amades, Maryse C. J. Osté, Maria Lankinen, Johanna M. Geleijnse, Janette de Goede, Marynka Ulaszewska, Fulvio Mattivi, Stephan J. L. Bakker, Ursula Schwab, Cristina Andres-Lacueva. Biomarkers of food intake for nuts and vegetable oils: an extensive literature search. Genes & Nutrition 2019, 14 (1) https://doi.org/10.1186/s12263-019-0628-8
  9. Marjo Tuomainen, Olli Kärkkäinen, Jukka Leppänen, Seppo Auriola, Marko Lehtonen, Markku J Savolainen, Kjeld Hermansen, Ulf Risérus, Björn Åkesson, Inga Thorsdottir, Marjukka Kolehmainen, Matti Uusitupa, Kaisa Poutanen, Ursula Schwab, Kati Hanhineva. Quantitative assessment of betainized compounds and associations with dietary and metabolic biomarkers in the randomized study of the healthy Nordic diet (SYSDIET). The American Journal of Clinical Nutrition 2019, 110 (5) , 1108-1118. https://doi.org/10.1093/ajcn/nqz179
  10. Casey M Rebholz, Alice H Lichtenstein, Zihe Zheng, Lawrence J Appel, Josef Coresh. Serum untargeted metabolomic profile of the Dietary Approaches to Stop Hypertension (DASH) dietary pattern. The American Journal of Clinical Nutrition 2018, 108 (2) , 243-255. https://doi.org/10.1093/ajcn/nqy099
  11. Ying Wang, Susan M Gapstur, Brian D Carter, Terryl J Hartman, Victoria L Stevens, Mia M Gaudet, Marjorie L McCullough. Untargeted Metabolomics Identifies Novel Potential Biomarkers of Habitual Food Intake in a Cross-Sectional Study of Postmenopausal Women. The Journal of Nutrition 2018, 148 (6) , 932-943. https://doi.org/10.1093/jn/nxy027
  12. Ikram Belghit, Josef D. Rasinger, Svenja Heesch, Irene Biancarosa, Nina Liland, Bente Torstensen, Rune Waagbø, Erik-Jan Lock, Christian G. Bruckner. In-depth metabolic profiling of marine macroalgae confirms strong biochemical differences between brown, red and green algae. Algal Research 2017, 26 , 240-249. https://doi.org/10.1016/j.algal.2017.08.001
  13. Jenni Puurunen, Katriina Tiira, Marko Lehtonen, Kati Hanhineva, Hannes Lohi. Non-targeted metabolite profiling reveals changes in oxidative stress, tryptophan and lipid metabolisms in fearful dogs. Behavioral and Brain Functions 2016, 12 (1) https://doi.org/10.1186/s12993-016-0091-2
  14. E Isganaitis, S L Rifas-Shiman, E Oken, J M Dreyfuss, W Gall, M W Gillman, M-E Patti. Associations of cord blood metabolites with early childhood obesity risk. International Journal of Obesity 2015, 39 (7) , 1041-1048. https://doi.org/10.1038/ijo.2015.39
  15. Isabel Bondia-Pons, José Alfredo Martinez, Rocio de la Iglesia, Patricia Lopez-Legarrea, Kaisa Poutanen, Kati Hanhineva, Maria de los Ángeles Zulet. Effects of short- and long-term Mediterranean-based dietary treatment on plasma LC-QTOF/MS metabolic profiling of subjects with metabolic syndrome features: The Metabolic Syndrome Reduction in Navarra (RESMENA) randomized controlled trial. Molecular Nutrition & Food Research 2015, 59 (4) , 711-728. https://doi.org/10.1002/mnfr.201400309
  16. Allegra Vit, Laëtitia Misson, Wulf Blankenfeldt, Florian P. Seebeck. Ergothioneine Biosynthetic Methyltransferase EgtD Reveals the Structural Basis of Aromatic Amino Acid Betaine Biosynthesis. ChemBioChem 2015, 16 (1) , 119-125. https://doi.org/10.1002/cbic.201402522
  17. Kristin A Guertin, Steven C Moore, Joshua N Sampson, Wen-Yi Huang, Qian Xiao, Rachael Z Stolzenberg-Solomon, Rashmi Sinha, Amanda J Cross. Metabolomics in nutritional epidemiology: identifying metabolites associated with diet and quantifying their potential to uncover diet-disease relations in populations. The American Journal of Clinical Nutrition 2014, 100 (1) , 208-217. https://doi.org/10.3945/ajcn.113.078758
  18. Romanas Chaleckis, Masahiro Ebe, Tomáš Pluskal, Itsuo Murakami, Hiroshi Kondoh, Mitsuhiro Yanagida. Unexpected similarities between the Schizosaccharomyces and human blood metabolomes, and novel human metabolites. Mol. BioSyst. 2014, 10 (10) , 2538-2551. https://doi.org/10.1039/C4MB00346B

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

Pair your accounts.

Export articles to Mendeley

Get article recommendations from ACS based on references in your Mendeley library.

You’ve supercharged your research process with ACS and Mendeley!

STEP 1:
Click to create an ACS ID

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

MENDELEY PAIRING EXPIRED
Your Mendeley pairing has expired. Please reconnect

This website uses cookies to improve your user experience. By continuing to use the site, you are accepting our use of cookies. Read the ACS privacy policy.

CONTINUE