title: Citrus genus plants contain N-methylated tryptamine derivatives and their 5-hydroxylated forms.
abstract: The occurrence and distribution in Citrus genus plants of N-methylated derivatives of tryptamine and their 5-hydroxylated forms are reported. Tryptamine, N-methyltryptamine, N,N-dimethyltryptamine, N,N,N-trimethyltryptamine, 5-hydroxytryptamine (serotonin), 5-hydroxy-N-methyltryptamine, 5-hydroxy-N,N-dimethyltryptamine (bufotenine), and 5-hydroxy-N,N,N-trimethyltryptamine (bufotenidine) were quantitated by LC-ESI-MS/MS. Leaves of all citrus plants examined contained N,N,N-trimethyltryptamine, a compound that we first discovered in the bergamot plant. Interestingly, we also found out that all plants examined contained 5-hydroxy-N,N-dimethyltryptamine and 5-hydroxy-N,N,N-trimethyltryptamine, compounds never described so far in the Citrus genus. As N,N,N-trimethyltryptamine and 5-hydroxy-N,N,N-trimethyltryptamine possess nicotine-like activity by exerting their action on acetylcholine receptors, it is conceivable that both represent the arrival point of a biosynthetic pathway aimed to provide Citrus plants with chemical defense against aggressors. This hypothesis is supported by our finding that leaves and seeds, which are more frequently attacked by biotic agents, are the parts of the plant where the highest levels of those compounds were found.
authors.affiliation: Dipartimento di Biochimica, Biofisica e Patologia Generale-II Università degli Studi di Napoli, via L. De Crecchio, 7- 80138 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: Rosario
authors.initials: R
authors.lastname: Casale
authors.forename: Domenico
authors.initials: D
authors.lastname: Cautela
authors.forename: Domenico
authors.initials: D
authors.lastname: Castaldo
mesh_terms: D002957:Citrus / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D018515:Plant Leaves / Q000737:chemistry; D053719:Tandem Mass Spectrometry; D014363:Tryptamines / Q000737:chemistry*
chemical_list: D010936:Plant Extracts; D014363:Tryptamines