{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T21:13:15Z","timestamp":1791839595294,"version":"4.3.4"},"reference-count":37,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"},{"start":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T00:00:00Z","timestamp":1738713600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0"}],"funder":[{"DOI":"10.13039\/501100007210","name":"RWTH Aachen University","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100007210","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Plant Methods"],"abstract":"<jats:title>Abstract<\/jats:title>\n          <jats:sec>\n            <jats:title>Background<\/jats:title>\n            <jats:p>Allergic contact dermatitis and chronic actinic dermatitis are frequently observed among florists and gardeners due to exposure to potentially allergenic plants and plant products. Tulipalin A, an alpha-methylene-gamma-butyrolactone, is a common allergen synthesized by <jats:italic>Tulipa<\/jats:italic> genera, but its natural occurrence across <jats:italic>Plantae<\/jats:italic> remains unexplored.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Results<\/jats:title>\n            <jats:p>Here, we demonstrated the secondary electrospray ionization coupled Orbitrap mass spectrometry (SESI-Orbitrap MS) methodology for quantifying tulipalin A release from plants upon injury. By outlining temperature treatment, homogenization strategies and plant organ distribution, we show that processing flower samples stored at room temperature using a garlic press yielded the highest tulipalin A release upon injury. Via real-time monitoring, tulipalin A release was demonstrated to occur immediately upon homogenization. Next, the biosynthesis of tulipalin A across spring flowers was landscaped. Highlighting <jats:italic>Rosa<\/jats:italic>, <jats:italic>Gerbera<\/jats:italic>, <jats:italic>Neapolitanum<\/jats:italic>, <jats:italic>Ranunculus<\/jats:italic>, <jats:italic>Othocalis<\/jats:italic>, <jats:italic>Muscari<\/jats:italic>, <jats:italic>Galanthus<\/jats:italic>, <jats:italic>Tulipa<\/jats:italic> and <jats:italic>Alstroemeria<\/jats:italic> to release detectable amounts of tulipalin A upon injury. Tulipalin A was predominantly released from the <jats:italic>Tulipa<\/jats:italic> and <jats:italic>Alstroemeria<\/jats:italic> species, both belonging to the Liliales order, as stated in previous clinical and research studies.<\/jats:p>\n          <\/jats:sec>\n          <jats:sec>\n            <jats:title>Conclusions<\/jats:title>\n            <jats:p>In conclusion, a rapid method using the SESI-Orbitrap MS is reported to detect and track tulipalin A synthesis across plant organs and outline its cross-species distribution. Our methodology can be easily adapted for mapping other volatile plant defense metabolites and identify potentially allergenic plants. By addressing these aspects, we can ensure a safer work environment for florists and gardeners.<\/jats:p>\n          <\/jats:sec>","DOI":"10.1186\/s13007-025-01331-6","type":"journal-article","created":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T06:01:11Z","timestamp":1738735271000},"update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Rapid detection of Tulipalin A with SESI-Orbitrap MS: an exploration across spring flowers"],"prefix":"10.1186","volume":"21","author":[{"given":"An N. T.","family":"Phan","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roy","family":"Eerlings","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hendrik G.","family":"Mengers","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lars M.","family":"Blank","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2025,2,5]]},"reference":[{"key":"1331_CR1","first-page":"811","volume-title":"The physiology of flower bulbs: a comprehensive treatise on the physiology and utilization of ornamental flowering bulbous and tuberous plants","author":"A De Hertogh","year":"1993","unstructured":"De Hertogh A, Nard ML. The physiology of flower bulbs: a comprehensive treatise on the physiology and utilization of ornamental flowering bulbous and tuberous plants. Amsterdam, The Netherlands; New York: Elsevier. xii; 1993. p. 811."},{"issue":"6","key":"1331_CR2","doi-asserted-by":"publisher","first-page":"320","DOI":"10.1111\/j.1600-0536.1999.tb06180.x","volume":"41","author":"LP Christensen","year":"1999","unstructured":"Christensen LP. Direct release of the allergen tulipalin A from Alstroemeria cut flowers: a possible source of airborne contact dermatitis? Contact Dermat. 1999;41(6):320\u20134.","journal-title":"Contact Dermat"},{"issue":"6","key":"1331_CR3","doi-asserted-by":"publisher","first-page":"397","DOI":"10.1093\/occmed\/48.6.397","volume":"48","author":"IA van der Mei","year":"1998","unstructured":"van der Mei IA, de Boer EM, Bruynzeel DP. Contact dermatitis in Alstroemeria workers. Occup Med (Lond). 1998;48(6):397\u2013404.","journal-title":"Occup Med (Lond)"},{"issue":"4","key":"1331_CR4","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1111\/j.1600-0536.1985.tb01110.x","volume":"12","author":"B Santucci","year":"1985","unstructured":"Santucci B, et al. Contact dermatitis to Alstroemeria. Contact Dermat. 1985;12(4):215\u20139.","journal-title":"Contact Dermat"},{"issue":"3","key":"1331_CR5","doi-asserted-by":"publisher","first-page":"196","DOI":"10.1034\/j.1600-0536.2001.440308-9.16","volume":"44","author":"R Mascarenhas","year":"2001","unstructured":"Mascarenhas R, et al. Allergic and irritant occupational contact dermatitis from Alstroemeria. Contact Dermat. 2001;44(3):196\u20137.","journal-title":"Contact Dermat"},{"issue":"2","key":"1331_CR6","doi-asserted-by":"publisher","first-page":"73","DOI":"10.1157\/13086751","volume":"34","author":"B Tavares","year":"2006","unstructured":"Tavares B, et al. Home gardening may be a risk factor for contact dermatitis to Alstroemeria. Allergol Immunopathol (Madr). 2006;34(2):73\u20135.","journal-title":"Allergol Immunopathol (Madr)"},{"issue":"1","key":"1331_CR7","doi-asserted-by":"publisher","first-page":"54","DOI":"10.1016\/0190-9622(90)70007-5","volume":"22","author":"DM Thiboutot","year":"1990","unstructured":"Thiboutot DM, Hamory BH, Marks JG Jr. Dermatoses among floral shop workers. J Am Acad Dermatol. 1990;22(1):54\u20138.","journal-title":"J Am Acad Dermatol"},{"key":"1331_CR8","doi-asserted-by":"crossref","unstructured":"Nomura T, Ogita S, Kato Y. A novel lactone-forming carboxylesterase: Molecular Identification of a Tuliposide A-Converting enzyme in Tulip Plant Physiology, 2012. 159(2): pp. 565\u201378.","DOI":"10.1104\/pp.112.195388"},{"issue":"1","key":"1331_CR9","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1080\/09168451.2016.1240608","volume":"81","author":"T Nomura","year":"2017","unstructured":"Nomura T. Function and application of a non-ester-hydrolyzing carboxylesterase discovered in tulip. Biosci Biotechnol Biochem. 2017;81(1):81\u201394.","journal-title":"Biosci Biotechnol Biochem"},{"issue":"6","key":"1331_CR10","doi-asserted-by":"publisher","first-page":"300","DOI":"10.1111\/j.1600-0536.1999.tb06080.x","volume":"40","author":"LP Christensen","year":"1999","unstructured":"Christensen LP, Kristiansen K. Isolation and quantification of tuliposides and tulipalins in tulips (Tulipa) by high-performance liquid chromatography. Contact Dermat. 1999;40(6):300\u20139.","journal-title":"Contact Dermat"},{"issue":"12","key":"1331_CR11","doi-asserted-by":"publisher","first-page":"2517","DOI":"10.1271\/bbb.130663","volume":"77","author":"K SHIGETOMI","year":"2013","unstructured":"SHIGETOMI K, et al. MurA as a primary target of Tulipalin B and 6-Tuliposide B. Biotechnol Biochem. 2013;77(12):2517\u20139. Bioscience.","journal-title":"Biotechnol Biochem"},{"issue":"4","key":"1331_CR12","doi-asserted-by":"publisher","first-page":"718","DOI":"10.1271\/bbb.100845","volume":"75","author":"K SHIGETOMI","year":"2011","unstructured":"SHIGETOMI K, et al. Asymmetric total synthesis of 6-Tuliposide B and its biological activities against Tulip pathogenic Fungi. Biotechnol Biochem. 2011;75(4):718\u201322. Bioscience.","journal-title":"Biotechnol Biochem"},{"issue":"23","key":"1331_CR13","doi-asserted-by":"publisher","first-page":"2997","DOI":"10.1002\/pmic.201600130","volume":"16","author":"P Zwicker","year":"2016","unstructured":"Zwicker P, et al. A proteomic approach for the identification of immunotoxic properties of Tulipalin A. Proteomics. 2016;16(23):2997\u20133008.","journal-title":"Proteomics"},{"key":"1331_CR14","first-page":"411","volume":"14","author":"B Amin","year":"2015","unstructured":"Amin B, et al. Protective effects of the aqueous extract of Crocus sativus against ethylene glycol induced nephrolithiasis in rats. EXCLI J. 2015;14:411\u201322.","journal-title":"EXCLI J"},{"issue":"3","key":"1331_CR15","doi-asserted-by":"publisher","first-page":"411","DOI":"10.1023\/A:1001174132428","volume":"40","author":"AMA Mazen","year":"1997","unstructured":"Mazen AMA, El OMO, Maghraby. Accumulation of cadmium, lead and strontium, and a role of calcium oxalate in water hyacinth tolerance. Biol Plant. 1997;40(3):411\u20137.","journal-title":"Biol Plant"},{"issue":"1","key":"1331_CR16","doi-asserted-by":"publisher","first-page":"41","DOI":"10.12788\/cutis.0678","volume":"111","author":"KP Lee","year":"2023","unstructured":"Lee KP, Elston DM. Botanical briefs: daffodils (Narcissus species). Cutis. 2023;111(1):41\u20135.","journal-title":"Cutis"},{"issue":"9","key":"1331_CR17","doi-asserted-by":"publisher","first-page":"e443","DOI":"10.1002\/pld3.443","volume":"6","author":"RE Paull","year":"2022","unstructured":"Paull RE, et al. Taro raphide-associated proteins: Allergens and crystal growth. Plant Direct. 2022;6(9):e443.","journal-title":"Plant Direct"},{"issue":"11","key":"1331_CR18","doi-asserted-by":"publisher","first-page":"2953","DOI":"10.1021\/acs.jnatprod.7b00495","volume":"80","author":"A Bozicevic","year":"2017","unstructured":"Bozicevic A, et al. Secondary metabolites in allergic plant pollen samples modulate afferent neurons and Murine Tracheal rings. J Nat Prod. 2017;80(11):2953\u201361.","journal-title":"J Nat Prod"},{"issue":"7","key":"1331_CR19","doi-asserted-by":"publisher","first-page":"6290","DOI":"10.1007\/s11356-019-04146-w","volume":"26","author":"M Denisow-Pietrzyk","year":"2019","unstructured":"Denisow-Pietrzyk M, Pietrzyk \u0141, Denisow B. Asteraceae species as potential environmental factors of allergy. Environ Sci Pollut Res Int. 2019;26(7):6290\u2013300.","journal-title":"Environ Sci Pollut Res Int"},{"issue":"1","key":"1331_CR20","doi-asserted-by":"publisher","first-page":"341","DOI":"10.1104\/pp.16.00625","volume":"172","author":"M Chen","year":"2016","unstructured":"Chen M, et al. Origin and functional prediction of Pollen allergens in plants. Plant Physiol. 2016;172(1):341\u201357.","journal-title":"Plant Physiol"},{"issue":"6","key":"1331_CR21","doi-asserted-by":"publisher","first-page":"745","DOI":"10.1016\/j.aller.2019.06.011","volume":"48","author":"Z Strzelczyk","year":"2020","unstructured":"Strzelczyk Z, et al. Avoidance of allergens as an environmental method in the prevention of inhaled allergy symptoms. Allergol Immunopathol. 2020;48(6):745\u201352.","journal-title":"Allergol Immunopathol"},{"issue":"3","key":"1331_CR22","doi-asserted-by":"publisher","first-page":"215","DOI":"10.1097\/00130832-200406000-00014","volume":"4","author":"DA Moneret-Vautrin","year":"2004","unstructured":"Moneret-Vautrin DA, Kanny G. Update on threshold doses of food allergens: implications for patients and the food industry. Curr Opin Allergy Clin Immunol. 2004;4(3):215\u20139.","journal-title":"Curr Opin Allergy Clin Immunol"},{"issue":"2","key":"1331_CR23","doi-asserted-by":"publisher","first-page":"565","DOI":"10.1104\/pp.112.195388","volume":"159","author":"T Nomura","year":"2012","unstructured":"Nomura T, Ogita S, Kato Y. A novel lactone-forming carboxylesterase: molecular identification of a tuliposide A-converting enzyme in tulip. Plant Physiol. 2012;159(2):565\u201378.","journal-title":"Plant Physiol"},{"key":"1331_CR24","doi-asserted-by":"publisher","first-page":"100030","DOI":"10.1016\/j.rechem.2020.100030","volume":"2","author":"H Mardani-Korrani","year":"2020","unstructured":"Mardani-Korrani H, et al. Application of the protoplast co-culture method for evaluation of allelopathic activities of volatile compounds, safranal and tulipalin A. Results Chem. 2020;2:100030.","journal-title":"Results Chem"},{"key":"1331_CR25","doi-asserted-by":"crossref","unstructured":"Nie Q, Nie S. 13 - High-performance liquid chromatography for food quality evaluation, in Evaluation Technologies for Food Quality, J. Zhong and X. Wang, Editors. 2019, Woodhead Publishing. pp. 267\u2013299.","DOI":"10.1016\/B978-0-12-814217-2.00013-5"},{"key":"1331_CR26","doi-asserted-by":"publisher","first-page":"261","DOI":"10.1016\/j.chemosphere.2013.10.094","volume":"99","author":"RS Jian","year":"2014","unstructured":"Jian RS, Sung LY, Lu CJ. Measuring real-time concentration trends of individual VOC in an elementary school using a sub-ppb detection muGC and a single GC-MS analysis. Chemosphere. 2014;99:261\u20136.","journal-title":"Chemosphere"},{"issue":"19","key":"1331_CR27","doi-asserted-by":"publisher","first-page":"4883","DOI":"10.1007\/s00216-019-01764-8","volume":"411","author":"KD Singh","year":"2019","unstructured":"Singh KD, et al. Standardization procedures for real-time breath analysis by secondary electrospray ionization high-resolution mass spectrometry. Anal Bioanal Chem. 2019;411(19):4883\u201398.","journal-title":"Anal Bioanal Chem"},{"key":"1331_CR28","doi-asserted-by":"publisher","first-page":"133804","DOI":"10.1016\/j.foodchem.2022.133804","volume":"397","author":"HG Mengers","year":"2022","unstructured":"Mengers HG, et al. Seeing the smell of garlic: detection of gas phase volatiles from crushed garlic (Allium sativum), onion (Allium cepa), ramsons (Allium ursinum) and human garlic breath using SESI-Orbitrap MS. Food Chem. 2022;397:133804.","journal-title":"Food Chem"},{"issue":"1","key":"1331_CR29","doi-asserted-by":"publisher","first-page":"12462","DOI":"10.1038\/s41598-022-16554-z","volume":"12","author":"HG Mengers","year":"2022","unstructured":"Mengers HG, Zimmermann M, Blank LM. Using off-gas for insights through online monitoring of ethanol and baker\u2019s yeast volatilome using SESI-Orbitrap MS. Sci Rep. 2022;12(1):12462.","journal-title":"Sci Rep"},{"key":"1331_CR30","doi-asserted-by":"publisher","first-page":"217","DOI":"10.1016\/j.snb.2015.09.073","volume":"223","author":"C Barrios-Collado","year":"2016","unstructured":"Barrios-Collado C, Vidal-de-Miguel G, Martinez-Lozano P, Sinues. Numerical modeling and experimental validation of a universal secondary electrospray ionization source for mass spectrometric gas analysis in real-time. Sens Actuators B. 2016;223:217\u201325.","journal-title":"Sens Actuators B"},{"issue":"6","key":"1331_CR31","doi-asserted-by":"publisher","first-page":"1085","DOI":"10.1007\/s13361-012-0369-z","volume":"23","author":"G Vidal-de-Miguel","year":"2012","unstructured":"Vidal-de-Miguel G, Herrero A. Secondary electrospray ionization of complex vapor mixtures. Theoretical and experimental approach. J Am Soc Mass Spectrom. 2012;23(6):1085\u201396.","journal-title":"J Am Soc Mass Spectrom"},{"key":"1331_CR32","doi-asserted-by":"crossref","unstructured":"Schoch CL et al. NCBI Taxonomy: a comprehensive update on curation, resources and tools. Database (Oxford), 2020. 2020.","DOI":"10.1093\/database\/baaa062"},{"issue":"1","key":"1331_CR33","doi-asserted-by":"publisher","first-page":"395","DOI":"10.1186\/1471-2105-11-395","volume":"11","author":"T Pluskal","year":"2010","unstructured":"Pluskal T, et al. MZmine 2: modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinformatics. 2010;11(1):395.","journal-title":"BMC Bioinformatics"},{"key":"1331_CR34","doi-asserted-by":"publisher","first-page":"1159","DOI":"10.1016\/B0-12-227050-9\/00128-9","volume-title":"SECONDARY PRODUallergensergens, in Encyclopedia of Applied sciencesiences","author":"LP Christensen","year":"2003","unstructured":"Christensen LP, Larsen E. SECONDARY PRODUallergensergens, in Encyclopedia of Applied sciencesiences. Oxford: Elsevier; 2003. pp. 1159\u201374. B. Thomas, Editor."},{"key":"1331_CR35","doi-asserted-by":"publisher","first-page":"338209","DOI":"10.1016\/j.aca.2021.338209","volume":"1150","author":"J Lan","year":"2021","unstructured":"Lan J, et al. Minimizing ion competition boosts volatile metabolome coverage by secondary electrospray ionization orbitrap mass spectrometry. Anal Chim Acta. 2021;1150:338209.","journal-title":"Anal Chim Acta"},{"issue":"8","key":"1331_CR36","doi-asserted-by":"publisher","first-page":"1895","DOI":"10.1271\/bbb.90226","volume":"73","author":"Y Kato","year":"2009","unstructured":"Kato Y, et al. Purification and characterization of a tuliposide-converting enzyme from bulbs of Tulipa gesneriana. Biosci Biotechnol Biochem. 2009;73(8):1895\u20137.","journal-title":"Biosci Biotechnol Biochem"},{"issue":"4","key":"1331_CR37","doi-asserted-by":"publisher","first-page":"417","DOI":"10.1006\/anbo.2000.1352","volume":"87","author":"RS Pearce","year":"2001","unstructured":"Pearce RS. Plant freezing and Damage. Ann Botany. 2001;87(4):417\u201324.","journal-title":"Ann Botany"}],"container-title":["Plant Methods"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s13007-025-01331-6.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/article\/10.1186\/s13007-025-01331-6\/fulltext.html","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/link.springer.com\/content\/pdf\/10.1186\/s13007-025-01331-6.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,2,5]],"date-time":"2025-02-05T06:01:16Z","timestamp":1738735276000},"score":1,"resource":{"primary":{"URL":"https:\/\/plantmethods.biomedcentral.com\/articles\/10.1186\/s13007-025-01331-6"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,5]]},"references-count":37,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2025,12]]}},"alternative-id":["1331"],"URL":"https:\/\/doi.org\/10.1186\/s13007-025-01331-6","relation":{},"ISSN":["1746-4811"],"issn-type":[{"value":"1746-4811","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,5]]},"assertion":[{"value":"4 July 2024","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"25 January 2025","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"5 February 2025","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Declarations"}},{"value":"Not applicable.","order":2,"name":"Ethics","group":{"name":"EthicsHeading","label":"Ethics approval and consent to participate"}},{"value":"Not applicable.","order":3,"name":"Ethics","group":{"name":"EthicsHeading","label":"Consent for publication"}},{"value":"The authors declare no competing interests.","order":4,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}],"article-number":"14"}}