N-methylated derivatives of tyramine in citrus genus plants: Identification of N, N, N-trimethyltyramine (candicine)

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 12, 2014, Pages 2679-2684

  Servillo, Luigi ^a   Giovane, Alfonso ^a   D'Onofrio, Nunzia ^a   Casale, Rosario ^a   Cautela, Domenico ^b   Ferrari, Giovanna ^c   Balestrieri, Maria Luisa ^a   Castaldo, Domenico ^c,d  

^a SECOND UNIVERSITY OF NAPLES   (Italy)

^b Stazione Sperimentale per le Industrie delle Essenze e dei Derivati Agrumari   (Italy)

^c UNIVERSITY OF SALERNO   (Italy)

^d Ministero dello Sviluppo Economico   (Italy)

Author keywords

biotic stress; candicine; Citrus plants; N, N, N trimethyltyramine; N methylated tyramine derivatives

Indexed keywords

AMINES; ELECTROSPRAY IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANTS (BOTANY); FRUITS; IONIZATION OF LIQUIDS; SPECTROMETRY;

BIOTIC STRESS; CANDICINE; CITRUS PLANT; LC-ESI-MS/MS; MASS SPECTROMETRIC ANALYSIS; QUATERNARY AMMONIUM COMPOUND; TANDEM MASS SPECTROMETRY; TRACE LEVEL; LIQUID CHROMATOGRAPHY ELECTROSPRAY;

CITRUS FRUITS;

PLANT EXTRACT; TYRAMINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CITRUS; CLASSIFICATION; FRUIT; METHYLATION; PLANT LEAF; TANDEM MASS SPECTROMETRY;

CITRUS; FRUIT; METHYLATION; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; TANDEM MASS SPECTROMETRY; TYRAMINE;

ANIMALIA; CITRUS; CITRUS AURANTIUM; CITRUS LIMON; CITRUS MAXIMA; CITRUS MEDICA; CITRUS MYRTIFOLIA; CITRUS RETICULATA;

EID: 84896913845     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf5001698     Document Type: Article

References (39)

1. Kutchan, T. M. A role for intra-and intercellular translocation in natural product biosynthesis Curr. Opin. Plant Biol. 2005, 8, 292-300
2. Murata, J.; Roepke, J.; Gordon, H.; De Luca, V. The leaf epidermome of Catharanthus roseus reveals its biochemical specialization Plant Cell 2008, 20, 524-542
3. Ballhorn, D. J.; Kautz, S.; Heil, M.; Hegeman, A. D. Analyzing plant defences in nature Plant Signal Behav. 2009, 8, 743-745
4. Facchini, P. J. Alkaloid biosynthesis in plants: Biochemistry, cell biology, molecular regulation, and metabolic engineering applications Annu. Rev. Plant Physiol. Plant Mol. Biol. 2001, 52, 29-66
5. O'Connor, S. E.; Maresh, J. Chemistry and biology of monoterpene indole alkaloid biosynthesis Nat. Prod. Rep. 2006, 23, 532-547
6. St.Pierre, B.; Vazquez-Flota, F. A.; De Luca, V. Multicellular compartmentation of Catharanthus roseus alkaloid biosynthesis predicts intercellular translocation of a pathway intermediate Plant Cell 1999, 11, 887-900
7. Irmler, S.; Schroder, G.; St. Pierre, B.; Crouch, N. P.; Hotze, M.; Schmidt, J.; Strack, D.; Matern, U.; Schroder, J. Indole alkaloid biosynthesis in Catharanthus roseus: new enzyme activities and identification of cytochrome P450 CYP72A1 as secologanin synthase Plant J. 2000, 24, 797-804
8. Burlat, V.; Oudin, A.; Courtois, M.; Rideau, M.; St. Pierre, B. Coexpression of three MEP pathway genes and geraniol 10-hydroxylase in internal phloem parenchyma of Catharanthus roseus implicates multicellular translocation of intermediates during the biosynthesis of monoterpene indole alkaloids and isoprenoid-derived primary metabolites Plant J. 2004, 38, 131-141
9. Gugler, K.; Funk, C.; Brodelius, P. Elicitor-induced tyrosine decarboxylase in berberine-synthesizing suspension cultures of Thalictrum rugosum Eur. J. Biochem. 1988, 170, 661-666
10. Kawalleck, P.; Keller, H.; Hahlbrock, K.; Scheel, D.; Somssich, I. E. A pathogen-responsive gene of parsley encodes tyrosine decarboxylase J. Biol. Chem. 1993, 268, 2189-2194
11. Facchini, P. J.; De Luca, V. Expression in Escherichia coli and partial characterization of two tyrosine/dopa decarboxylases from opium poppy Phytochemistry 1995, 38, 1119-1126
12. Gallon, J. R.; Butt, V. S. L-Tyrosine decarboxylase from barley roots Biochem. J. 1971, 123, 5P-6P
13. Facchini, P. J.; Huber-Allanach, K. L.; Tari, L. W. Plant aromatic-amino acid decarboxylases: evolution, biochemistry, regulation, and metabolic engineering applications Phytochemistry 2000, 54, 121-138
14. Facchini, P. J.; De Luca, V. Differential and tissue-specific expression of a gene family for tyrosine/dopa decarboxylase in opium poppy J. Biol. Chem. 1994, 269, 26684-26690
15. Bartley, G. E.; Breksa, A. P., III; Ishida, B. K. PCR amplification and cloning of tyrosine decarboxylase involved in synephrine biosynthesis in Citrus New Biotechnol. 2010, 27, 308-316
16. Pellati, F.; Benvenuti, S. Fast high-performance liquid chromatography analysis of phenethylamine alkaloids in citrus natural products on a pentafluorophenylpropyl stationary phases J. Chromatogr. A. 2007, 1165, 58-66
17. Nelson, B. C.; Putzbach, K.; Sharpless, K. E.; Sander, L. C. Mass spectrometric determination of the predominant adrenergic protoalkaloids in bitter orange (Citrus aurantium) J. Agric. Food Chem. 2007, 55, 9769-9775
18. Haaz, S.; Fontaine, K. R.; Cutter, G.; Limdi, N.; Perumean-Chaney, S.; Allison, D. B. Citrus aurantium and synephrine alkaloids in the treatment of overweight and obesity: an update Obes. Rev 2006, 7, 79-88
19. Stewart, I.; Newhall, W. F; Edwards, G. J. The isolation and identification of L-synephrine in the leaves and fruit of citrus J. Biol. Chem. 1964, 239, 85-92
20. Wheaton, T. A.; Stewart, I. Quantitative analysis of phenolic amines using ion exchange chromatography Anal. Biochem. 1965, 12, 585-592
21. Wheaton, T. A.; Stewart, I. Biosynthesis of synephrine in citrus Phytochemistry 1969, 8, 85-92
22. Urakawa, N.; Hayama, T.; Deguchi, T.; Ohkubo, Y. Some chemical and pharmacological properties of an amine (maltoxin) isolated from malt rootlet Jpn. J. Pharmacol. 1959, 9, 41-45
23. Urakawa, N.; Hirabe, Y.; Ohkubo, Y. Identification of maltoxin, an active principle from malt rootlet, as candicine Jpn. J. Pharmacol. 1961, 11, 4-10
24. Urakawa, N.; Deguchi, T.; Ohkubo, Y. Decamethonium-like action of maltoxin, an active principle from malt rootlet, on the frog muscle Jpn. J. Pharmacol. 1960, 10, 1-6
25. Deguchi, T.; Urakawa, N.; Hayama, T.; Ohkubo, Y. Ganglion stimulating action of candicine Jpn. J. Pharmacol. 1963, 13, 143-159
26. 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
27. 6-trimethyl-L-lysine dioxalate in gram amounts Biochem. Cell Biol. 1986, 64, 182-183
28. 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
29. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Casale, R.; Cautela, D.; Castaldo, D. Citrus genus plants contain N-methylated tryptamine derivatives and their 5-hydroxylated forms J. Agric. Food Chem. 2013, 61, 5156-5162
30. 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
31. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Ferrari, G.; Cautela, D.; Castaldo, D. Occurence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants J. Agric. Food Chem. 2012, 60, 315-321
32. Servillo, L.; Giovane, A.; Balestrieri, M. L.; Cautela, D.; Castaldo, D. Proline derivatives in fruits of bergamot (Citrus bergamia Risso et Poit): Presence of N -methylproline and 4-hydroxyprolinebetaine J. Agric. Food Chem. 2011, 59, 274-281
33. Cram, D. J.; Thompson, J. A. Phenonium verus open ions in solvolyses of 3-phenyl-2-butyl tosylate and its p-nitro derivative J. Am. Chem. Soc. 1967, 89, 6766-6768
34. 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
35. Cautela, D.; Castaldo, D.; Servillo, L.; Giovane, A. Enzymes in citrus juice processing. In Enzymes in Fruit and Vegetable Processing: Chemistry and Engineering Applications; Bayindirdli, A., Ed.; CRC Press, Taylor & Francis Group: Boca Raton, FL, 2010; pp 197-214.
36. Pieterse, C. M. J; Leon-Reyes, A.; Van der Ent, S.; Van Wees, S. C. M. Networking by small-molecule hormones in plant immunity Nat. Chem. Biol. 2009, 5, 308-316
37. Chehab, E. W.; Kaspi, R.; Savchenko, T.; Rowe, H.; Negre-Zakharov, F.; Liebenstein, D.; Dehesh, K. Distinct roles of jasmonates and aldehydes in plant-defense responses PLoS One 2008, 3, e1904
38. Kang, S.; Kang, K.; Lee, K.; Back, K. Characterization of tryptamine 5-hydroxylase and serotonin synthesis in rice plants Plant Cell Rep. 2007, 26, 2009-2015
39. Facchini, P. J.; Hagel, J.; Zulak, K. G. Hydroxycinnamic acid amide metabolism: physiology and biochemistry Can. J. Bot. 2002, 80, 577-589