Citrus genus plants contain N-methylated tryptamine derivatives and their 5-hydroxylated forms

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 21, 2013, Pages 5156-5162

  Servillo, Luigi ^a   Giovane, Alfonso ^a   Balestrieri, Maria Luisa ^a   Casale, Rosario ^a   Cautela, Domenico ^b   Castaldo, Domenico ^c,d  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b Stazione Sperimentale per le Industrie Delle Essenze e Dei Derivati Dagli Agrumi SSEA   (Italy)

^c Ministero Dello Sviluppo Economico (MiSE)   (Italy)

^d UNIVERSITY OF SALERNO   (Italy)

Author keywords

5 hydroxy N, N, N trimethyltryptamine; biotic stress; bufotenine; citrus plants; hydroxylated tryptamine derivatives; psilocin; tryptamine derivatives

Indexed keywords

5-HYDROXY- N, N, N -TRIMETHYLTRYPTAMINE; BIOTIC STRESS; BUFOTENINE; CITRUS PLANT; PSILOCIN; TRYPTAMINE DERIVATIVES;

HYDROXYLATION; SEED;

PLANTS (BOTANY);

PLANT EXTRACT; TRYPTAMINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CITRUS; PLANT LEAF; TANDEM MASS SPECTROMETRY;

CITRUS; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; TANDEM MASS SPECTROMETRY; TRYPTAMINES;

CITRUS;

EID: 84878405373     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf401448q     Document Type: Article

References (20)

1. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Cautela, D.; Castaldo, D. N -Methylated tryptamine derivatives in Citrus genus plants: identification of N, N, N -trimethyltryptamine in bergamot J. Agric. Food Chem. 2012, 60, 9512-9518
2. Gill, R. I. S.; Ellis, B. E.; Isman, M. B. Tryptamine induced resistance in tryptophan decarboxylase transgenic poplar and tobacco plants against their specific herbivores J. Chem. Ecol. 2003, 29, 779-793
3. Facchini, P. J.; Huber-Allanach, K. L.; Tari, L. W. Plant aromatic L-amino acid decarboxylase: evolution, biochemistry, regulation, and metabolic engineering applications Phytochemistry 2000, 54, 121-138
4. De Luca, V.; Marineau, C.; Brisson, N. Molecular cloning and analysis of a cDNA encoding a plant tryptophan decarboxylase Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 2582-2586
5. Cautela, D.; Laratta, B.; Santelli, F.; Trifirò, A.; Servillo, L.; Castaldo, D. Estimating bergamot juice adulteration of lemon juice by high performance liquid chromatography (HPLC) analysis of flavanone glycosides J. Agric. Food Chem. 2008, 56, 5407-5414
6. Cautela, D.; Castaldo, D.; Santelli, F.; Laratta, B.; Pirrello, A. G.; Malorni, A.; Boscaino, F. Survey of polychlorinated dibenzo-p-dioxins (PCDDs), polychlorinated dibenzo-p-furans (PCDFs), polychlorinated biphenyls (PCBs) and mineral components in Italian Citrus cold pressed oils J. Agric. Food Chem. 2007, 55, 1627-1637
7. Siano, F.; Cautela, D. Analisi comparativa di oli essenziali agrumari italiani estratti a freddo Ind. Conserve 2012, 87, 99-108
8. O'Connor, S. E.; Maresh, J. Chemistry and biology of monoterpene indole alkaloid biosynthesis Nat. Prod. Rep. 2006, 23, 532-547
9. Barlow, R. B.; Burston, K. N. A comparison of cinobufotenine (the quaternary derivative of 5-HT) and some related compounds with coryneine (the quaternary derivative of dopamine) on the frog rectus, guinea-pig ileum and rat fundus strip preparations Br. J. Pharmacol. 1980, 69, 597-600
10. Chen, F. M. F.; Benoiton, N. L. A new method of quaternizing amines and its use in amino acid and peptide chemistry Can. J. Chem. 1976, 54, 3310-3311
11. 6-trimethyl-L-lysine dioxalate in gram amounts Biochem. Cell Biol. 1986, 64, 182-183
12. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Bata-Csere, A.; Cautela, D.; Castaldo, D. Betaines in fruits of Citrus genus plants J. Agric. Food Chem. 2011, 59, 9410-9416
13. McClean, S.; Robinson, R. C.; Shaw, C.; Smyth, F. Characterisation and determination of indole alkaloids in frog-skin secretions by electrospray ionisation ion trap mass spectrometry Rapid Commun. Mass Spectrom. 2002, 16, 346-354
14. Hillebrand, J.; Olszewski, D.; Sedefov, R. Hallucinogenic Mushrooms: an Emerging Trend Case Study; European Monitoring Centre for Drugs and Addiction (EMCDDA): Lisbon, Portugal, 2006; http://www.emcdda.europa.eu (accessed 18/05/2012).
15. Gartz, J.; Allen, J. W. Teonanácatl: A Bibliography of Entheogenic Fungi; Mycoart.org: Knüllwald, Germany, 2001; http://www.mycoart.org (accessed 12/12/2011).
16. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Ferrari, G.; Cautela, D.; Castaldo, D. Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants J. Agric. Food Chem. 2012, 60, 315-321
17. Zhao, Y.; Christensen, S. K.; Fankhauser, C.; Cashman, J. R.; Cohen, J. D.; Weigel, D.; Chory, J. A role for flavin monooxygenase-like enzymes in auxin biosynthesis Science 2001, 291, 306-309
18. Murch, S. J.; KrishnaRaj, S.; Saxena, P. K. Tryptophan is a precursor for melatonin and serotonin biosynthesis in in vitro regenerated St. John's wort (Hypericum perforatum L. cv. Anthos) plants Plant Cell Rep. 2000, 19, 698-704
19. Veenstra-VanderWeele, J.; Anderson, G. M.; Cook, E. H. Pharmacogenetics and the serotonin system: initial studies and future directions Eur. J. Pharmacol. 2000, 410, 165-181
20. Schroder, P.; Abele, C.; Gohr, P.; Stuhlfauth-Roisch, U.; Grosse, W. Latest on the enzymology of serotonin biosynthesis in walnut seeds Adv. Exp. Med. Biol. 1999, 467, 637-644