title: N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot.
abstract: The occurrence of N-methylated tryptamine derivatives in bergamot plant (Citrus bergamia Risso et Poit) is reported for the first time. Interestingly, the most abundant of these substances is N,N,N-trimethyltryptamine, which has not been previously identified in any citrus plant. The N-methylated tryptamine derivatives were identified and quantitated in leaves, peel, juice, and seeds by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry. N,N,N-Trimethyltryptamine was confirmed by MS(3) and comparison with the synthesized authentic standard. In addition, the study of the distribution of tryptophan, tryptamine, N-methyltryptamine, N,N-dimethyltryptamine, and N,N,N-trimethyltryptamine indicated that these compounds are differently expressed in the various tissues of the bergamot plant. Intriguingly, chemically synthesized N,N,N-trimethyltryptamine was reported to possess nicotine-like activity being a stimulant of parasympathetic ganglia by exerting its action on acetylcholine receptors. On this basis, the identification of N,N,N-trimethyltryptamine at a relatively high level in leaves suggests a possible role in a physiological mechanism of plant defense.
authors.affiliation: Dipartimento di Biochimica e Biofisica, II Università degli Studi di Napoli, Naples, Italy. luigi.servillo@unina2.it
authors.forename: Luigi
authors.initials: L
authors.lastname: Servillo
authors.forename: Alfonso
authors.initials: A
authors.lastname: Giovane
authors.forename: Maria Luisa
authors.initials: ML
authors.lastname: Balestrieri
authors.forename: Domenico
authors.initials: D
authors.lastname: Cautela
authors.forename: Domenico
authors.initials: D
authors.lastname: Castaldo
mesh_terms: D002851:Chromatography, High Pressure Liquid; D002957:Citrus / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry; D012639:Seeds / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry; D014363:Tryptamines / Q000032:analysis* / Q000737:chemistry
chemical_list: C577668:N,N,N-trimethyltryptamine; D014363:Tryptamines; C035668:N-methyltryptamine