{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,3]],"date-time":"2026-08-03T05:16:39Z","timestamp":1785734199918,"version":"3.56.0"},"reference-count":28,"publisher":"Springer Science and Business Media LLC","issue":"2","license":[{"start":{"date-parts":[[2023,1,2]],"date-time":"2023-01-02T00:00:00Z","timestamp":1672617600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2023,1,2]],"date-time":"2023-01-02T00:00:00Z","timestamp":1672617600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Amino Acids"],"published-print":{"date-parts":[[2023,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>L-tryptophan has been used as a feed additive for swine and poultry and as a nutrient supplement for humans. However, some impurities in <jats:sc>l<\/jats:sc>-tryptophan have been reported as causative components of eosinophilia-myalgia syndrome. Therefore, from a safety perspective, it is important to analyze meat samples for these impurities. This study aims to develop an analytical method for the simultaneous detection of <jats:sc>l<\/jats:sc>-tryptophan impurities in meat products using LC\u2013MS\/MS. Among the various impurities, detection methods for (S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid (5-hydroxytryptophan) (HTP), 1-methyl-1,2,3,4-tetrahydro-\u03b2-carboline-3-carboxylic acid (MTCA), 3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo-[2,3-b]-indole-2-carboxylic acid (PIC), and 1,1\u2032-ethylidenebistryptophan (EBT) and 2-(3-indoylmethyl)-<jats:sc>l<\/jats:sc>-tryptophan (IMT) were developed. The developed method allowed simultaneous determination of these four impurities in 5\u00a0min. No interferences from the matrix were observed, and the method showed good sensitivity to each analyte. The method detection limit and limit of quantification in meat matrices were below 11.2 and 35.7\u00a0\u03bcg\/kg, respectively.<\/jats:p>","DOI":"10.1007\/s00726-022-03215-8","type":"journal-article","created":{"date-parts":[[2023,1,2]],"date-time":"2023-01-02T03:02:32Z","timestamp":1672628552000},"page":"173-182","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Simultaneous determination of l-tryptophan impurities in meat products"],"prefix":"10.1007","volume":"55","author":[{"given":"Doo-Hee","family":"Lee","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yang Hee","family":"Kim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mina","family":"Baek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"In Kyung","family":"Heo","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yonguk","family":"Shin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2023,1,2]]},"reference":[{"issue":"1\u20132","key":"3215_CR1","doi-asserted-by":"publisher","first-page":"501","DOI":"10.1016\/s0021-9673(00)00197-7","volume":"881","author":"J Adachi","year":"2000","unstructured":"Adachi J, Asano M, Ueno Y (2000) Tetrahydro-beta-carboline-3-carboxylic acids and contaminants of L-tryptophan. J Chromatogr A 881(1\u20132):501\u2013515. https:\/\/doi.org\/10.1016\/s0021-9673(00)00197-7","journal-title":"J Chromatogr A"},{"key":"3215_CR2","first-page":"1523","volume-title":"Eosinophilia-myalgia syndrome, eosinophilic fasciitis, and related fasciitis disorders","author":"JA Allen","year":"2014","unstructured":"Allen JA, Varga J (2014) Eosinophilia-myalgia syndrome, eosinophilic fasciitis, and related fasciitis disorders. Springer, New York, pp 1523\u20131535"},{"key":"3215_CR3","first-page":"114","volume-title":"Meyler's side effects of drugs: the international encyclopedia of adverse drug reactions and interactions","author":"JK Aronson","year":"2015","unstructured":"Aronson JK (2015) Meyler\u2019s side effects of drugs: the international encyclopedia of adverse drug reactions and interactions, 16th edn. Elsevier, Amsterdam, p 114","edition":"16"},{"issue":"6","key":"3215_CR4","doi-asserted-by":"publisher","first-page":"357","DOI":"10.1056\/NEJM199008093230601","volume":"323","author":"EA Belongia","year":"1990","unstructured":"Belongia EA, Hedberg CW, Gleich GJ, White KE, Mayeno AN, Loegering DA, Dunnette SL, Pirie PL, MacDonald KL, Osterholm MT (1990) An investigation of the cause of the eosinophilia-myalgia syndrome associated with tryptophan use. N Engl J Med 323(6):357\u2013365. https:\/\/doi.org\/10.1056\/NEJM199008093230601","journal-title":"N Engl J Med"},{"issue":"6","key":"3215_CR5","doi-asserted-by":"publisher","first-page":"788","DOI":"10.1016\/S0049-0172(97)80022-4","volume":"26","author":"WD Blackburn","year":"1997","unstructured":"Blackburn WD (1997) Eosinophilia myalgia syndrome. Semin Arthritis Rheum 26(6):788\u2013793. https:\/\/doi.org\/10.1016\/S0049-0172(97)80022-4","journal-title":"Semin Arthritis Rheum"},{"issue":"1","key":"3215_CR6","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1016\/j.toxlet.2003.12.070","volume":"150","author":"YT Das","year":"2004","unstructured":"Das YT, Bagchi M, Bagchi D, Preuss HG (2004) Safety of 5-hydroxy-l-tryptophan. Toxicol Lett 150(1):111\u2013122. https:\/\/doi.org\/10.1016\/j.toxlet.2003.12.070","journal-title":"Toxicol Lett"},{"key":"3215_CR7","unstructured":"European Commission (2002) Implementing Council Directive 96\/23\/EC concerning the performance of analytical methods and interpretation of results, Off J Eur Commun L221\/8"},{"key":"3215_CR8","unstructured":"European Commission (2021) Guidance document on pesticide analytical methods for risk assessment and post\u2010approval control and monitoring purposes. SANTE\/2020\/12830\u2010rev. 1, 24 Feb 2021"},{"issue":"Suppl 1","key":"3215_CR9","doi-asserted-by":"publisher","first-page":"3","DOI":"10.4137\/IJTR.S11588","volume":"6","author":"T Fukuwatari","year":"2013","unstructured":"Fukuwatari T, Shibata K (2013) Nutritional aspect of tryptophan metabolism. Int J Tryptophan Res 6(Suppl 1):3\u20138. https:\/\/doi.org\/10.4137\/IJTR.S11588","journal-title":"Int J Tryptophan Res"},{"issue":"1","key":"3215_CR10","doi-asserted-by":"publisher","first-page":"134","DOI":"10.1007\/BF00230724","volume":"25","author":"RH Hill","year":"1993","unstructured":"Hill RH, Caudill SP, Philen RM, Bailey SL, Flanders WD, Driskell WJ, Kamb ML, Needham LL, Sampson EJ (1993) Contaminants in L-tryptophan associated with eosinophilia myalgia syndrome. Arch Environ Contam Toxicol 25(1):134\u2013142. https:\/\/doi.org\/10.1007\/BF00230724","journal-title":"Arch Environ Contam Toxicol"},{"key":"3215_CR11","doi-asserted-by":"publisher","first-page":"158","DOI":"10.3389\/fendo.2019.00158","volume":"10","author":"E H\u00f6glund","year":"2019","unstructured":"H\u00f6glund E, \u00d8verli \u00d8, Winberg S (2019) Tryptophan metabolic pathways and brain serotonergic activity: a comparative review. Front Endocrinol 10:158. https:\/\/doi.org\/10.3389\/fendo.2019.00158","journal-title":"Front Endocrinol"},{"key":"3215_CR12","unstructured":"ICH Harmonised Tripartite Guideline (2005) Validation of Analytical Procedures: Text and Methodology Q2(R1)"},{"issue":"1","key":"3215_CR13","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1016\/0278-6915(92)90139-c","volume":"30","author":"J Ito","year":"1992","unstructured":"Ito J, Hosaki Y, Torigoe Y, Sakimoto K (1992) Identification of substances formed by decomposition of peak E substance in tryptophan. Food Chem Toxicol 30(1):71\u201381. https:\/\/doi.org\/10.1016\/0278-6915(92)90139-c","journal-title":"Food Chem Toxicol"},{"issue":"3","key":"3215_CR14","doi-asserted-by":"publisher","first-page":"1017","DOI":"10.2527\/jas.2008-1627","volume":"88","author":"AJM Jansman","year":"2010","unstructured":"Jansman AJM, van Diepen JTM, Melchior MB (2010) The effect of diet composition on tryptophan requirement of young piglets. J Anim Sci 88(3):1017\u20131027. https:\/\/doi.org\/10.2527\/jas.2008-1627","journal-title":"J Anim Sci"},{"key":"3215_CR15","doi-asserted-by":"publisher","first-page":"835","DOI":"10.1007\/s00726-022-03125-9","volume":"54","author":"S Karakawa","year":"2022","unstructured":"Karakawa S, Nakayama A, Ohtsuka N, Sato K, Smriga M (2022) Detection of impurities in dietary supplements containing L-tryptophan. Amino Acids 54:835\u2013839. https:\/\/doi.org\/10.1007\/s00726-022-03125-9","journal-title":"Amino Acids"},{"key":"3215_CR16","doi-asserted-by":"publisher","first-page":"16","DOI":"10.1093\/oxfordjournals.epirev.a036085","volume":"14","author":"EM Kilbourne","year":"1992","unstructured":"Kilbourne EM (1992) Eosinophilia-myalgia syndrome: coming to grips with a new illness. Epidemiol Rev 14:16\u201336. https:\/\/doi.org\/10.1093\/oxfordjournals.epirev.a036085","journal-title":"Epidemiol Rev"},{"issue":"11","key":"3215_CR17","doi-asserted-by":"publisher","first-page":"942","DOI":"10.1016\/S1044-0305(00)00163-X","volume":"11","author":"R King","year":"2000","unstructured":"King R, Bonfiglio R, Fernandez-Metzler C, Miller-Stein C, Olah T (2000) Mechanistic investigation of ionization suppression in electrospray ionization. J Am Soc Mass Spectrom 11(11):942\u2013950. https:\/\/doi.org\/10.1016\/S1044-0305(00)00163-X","journal-title":"J Am Soc Mass Spectrom"},{"key":"3215_CR18","doi-asserted-by":"publisher","first-page":"71","DOI":"10.1016\/j.toxlet.2017.10.012","volume":"282","author":"K Klarskov","year":"2018","unstructured":"Klarskov K, Gagnon H, Boudreault PL, Normandin C, Plancq B, Marsault E, Gleich GJ, Naylor S (2018) Structure determination of disease associated peak AAA from l-Tryptophan implicated in the eosinophilia-myalgia syndrome. Toxicol Lett 282:71\u201380. https:\/\/doi.org\/10.1016\/j.toxlet.2017.10.012","journal-title":"Toxicol Lett"},{"issue":"1\u20132","key":"3215_CR19","doi-asserted-by":"publisher","first-page":"23","DOI":"10.1016\/j.livsci.2007.07.002","volume":"112","author":"N Le Floc'h","year":"2007","unstructured":"Le Floc\u2019h N, Seve B (2007) Biological roles of tryptophan and its metabolism: potential implications for pig feeding. Livest Sci 112(1\u20132):23\u201332. https:\/\/doi.org\/10.1016\/j.livsci.2007.07.002","journal-title":"Livest Sci"},{"issue":"4988","key":"3215_CR20","doi-asserted-by":"publisher","first-page":"1707","DOI":"10.1126\/science.2270484","volume":"250","author":"AN Mayeno","year":"1990","unstructured":"Mayeno AN, Lin F, Foote CS, Loegering DA, Ames MM, Hedberg CW, Gleich GJ (1990) Characterization of \u201cpeak E,\u201d a novel amino acid associated with eosinophilia-myalgia syndrome. Science 250(4988):1707\u20131708. https:\/\/doi.org\/10.1126\/science.2270484","journal-title":"Science"},{"key":"3215_CR21","doi-asserted-by":"publisher","first-page":"290","DOI":"10.1007\/BF01974349","volume":"67","author":"Y Ogawa","year":"1993","unstructured":"Ogawa Y, Adachi J, Tatsuno Y (1993) Accumulation of 1-methyl-tetrahydro-\u0392-carboline-3-carboxylic acid in blood and organs of rat. A possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. Arch Toxicol 67:290\u2013293. https:\/\/doi.org\/10.1007\/BF01974349","journal-title":"Arch Toxicol"},{"issue":"5","key":"3215_CR22","doi-asserted-by":"publisher","first-page":"815","DOI":"10.1093\/ps\/82.5.815","volume":"82","author":"S Peganova","year":"2003","unstructured":"Peganova S, Hirche F, Eder K (2003) Requirement of tryptophan in relation to the supply of large neutral amino acids in laying hens. Poult Sci 82(5):815\u2013822. https:\/\/doi.org\/10.1093\/ps\/82.5.815","journal-title":"Poult Sci"},{"issue":"3","key":"3215_CR23","doi-asserted-by":"publisher","first-page":"154","DOI":"10.1093\/oxfordjournals.aje.a116841","volume":"138","author":"RM Philen","year":"1993","unstructured":"Philen RM, Hill RH Jr, Flanders WD, Caudill SP, Needham L, Sewell L, Sampson EJ, Falk H, Kilbourne EM (1993) Tryptophan contaminants associated with eosinophilia-myalgia syndrome. Am J Epidemiol 138(3):154\u2013159. https:\/\/doi.org\/10.1093\/oxfordjournals.aje.a116841","journal-title":"Am J Epidemiol"},{"key":"3215_CR24","doi-asserted-by":"publisher","DOI":"10.1007\/978-1-4615-4709-9_95","volume-title":"Tryptophan, serotonin, and melatonin","author":"B S\u00e8ve","year":"1999","unstructured":"S\u00e8ve B (1999) Physiological roles of tryptophan in pig nutrition. In: Huether G, Kochen W, Simat TJ, Steinhart H (eds) Tryptophan, serotonin, and melatonin, vol 467. Springer, Boston"},{"issue":"3","key":"3215_CR25","doi-asserted-by":"publisher","first-page":"241","DOI":"10.1007\/s00217-002-0646-3","volume":"216","author":"TJ Simat","year":"2003","unstructured":"Simat TJ, Kleeberg KK, M\u00fcller B, Sierts A (2003) Contamination of commercially available L-tryptophan by related substances. Eur Food Res Technol 216(3):241\u2013252. https:\/\/doi.org\/10.1007\/s00217-002-0646-3","journal-title":"Eur Food Res Technol"},{"issue":"2","key":"3215_CR26","doi-asserted-by":"publisher","first-page":"139","DOI":"10.1016\/s0378-4274(98)00223-9","volume":"99","author":"BL Williamson","year":"1998","unstructured":"Williamson BL, Johnson KL, Tomlinson AJ, Gleich GJ, Naylor S (1998) On-line HPLC-tandem mass spectrometry structural characterization of case-associated contaminants of l-tryptophan implicated with the onset of eosinophilia myalgia syndrome. Toxicol Lett 99(2):139\u2013150. https:\/\/doi.org\/10.1016\/s0378-4274(98)00223-9","journal-title":"Toxicol Lett"},{"issue":"3","key":"3215_CR27","doi-asserted-by":"publisher","first-page":"1008","DOI":"10.1016\/0006-291x(91)90992-g","volume":"178","author":"Y Yamaguchi","year":"1991","unstructured":"Yamaguchi Y, Tsunoda J, Suda T, Miura Y, Shioiri-Nakano K, Kasahara T (1991) Effect of synthesized constituents in the L-tryptophan product on the differentiation of eosinophils and the induction of IL-6: a possible cause of eosinophilia-myalgia syndrome. Biochem Biophys Res Commun 178(3):1008\u20131013. https:\/\/doi.org\/10.1016\/0006-291x(91)90992-g","journal-title":"Biochem Biophys Res Commun"},{"issue":"23","key":"3215_CR28","doi-asserted-by":"publisher","first-page":"1839","DOI":"10.4155\/bio-2017-0214","volume":"9","author":"W Zhou","year":"2017","unstructured":"Zhou W, Yang S, Wang PG (2017) Matrix effects and application of matrix effect factor. Bioanalysis 9(23):1839\u20131844. https:\/\/doi.org\/10.4155\/bio-2017-0214","journal-title":"Bioanalysis"}],"container-title":["Amino Acids"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s00726-022-03215-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1007\/s00726-022-03215-8\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1007\/s00726-022-03215-8.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,2,23]],"date-time":"2023-02-23T18:04:56Z","timestamp":1677175496000},"score":1,"resource":{"primary":{"URL":"https:\/\/link.springer.com\/10.1007\/s00726-022-03215-8"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,2]]},"references-count":28,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2023,2]]}},"alternative-id":["3215"],"URL":"https:\/\/doi.org\/10.1007\/s00726-022-03215-8","relation":{},"ISSN":["0939-4451","1438-2199"],"issn-type":[{"value":"0939-4451","type":"print"},{"value":"1438-2199","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,2]]},"assertion":[{"value":"11 July 2022","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"14 November 2022","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"2 January 2023","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"YHK, MB, HIK, and YS are employed by CJ CheilJedang (Suwon, South Korea).","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Conflict of interest"}}]}}