Occurrence of pipecolic acid and pipecolic acid betaine (homostachydrine) in Citrus genus plants

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 1, 2012, Pages 315-321

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

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

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

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

Author keywords

betaine biosynthesis; citrus fruit; citrus fruit composition; food analysis; homostachydrine; pipecolic acid; pipecolic acid betaine

Indexed keywords

ABIOTIC STRESS; CITRUS PLANT; ESI-MS/MS; FOOD ANALYSIS; FRAGMENTATION PATTERNS; HIGH CONCENTRATION; HIGH SENSITIVITY; HOMOSTACHYDRINE; ION TRAP MASS SPECTROMETER; IONIC FRAGMENTS; MEDICAGO; MS/MS FRAGMENTATION; OSMOLYTES; PIPECOLIC ACID; POSITIVE ION MODE;

ALKYLATION; AMINO ACIDS; BIOCHEMISTRY; PIPE;

CITRUS FRUITS;

BETAINE; DRUG DERIVATIVE; PIPECOLIC ACID; PIPECOLIC ACID DERIVATIVE; PLANT EXTRACT; PROLINE; STACHYDRINE;

ARTICLE; CHEMISTRY; CITRUS;

BETAINE; CITRUS; PIPECOLIC ACIDS; PLANT EXTRACTS; PROLINE;

CITRUS; CITRUS AURANTIUM BERGAMIA; CITRUS LIMON; MEDICAGO SATIVA;

EID: 84855772476     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf204286r     Document Type: Article

References (33)

1. Hasegawa, P. M.; Bressan, R. A.; Kang Zhu, J.; Bohnert, J. Plant cellular and molecular responses to high salinity Annu. Rev. Plant Physiol. Plant Mol. Biol. 2000, 51, 463-499
2. Rhodes, D.; Verlues, P. E.; Sharp, R. E. Role of amino acids in abiotic stress resistance. In Plant Amino Acids: Biochemistry and Biotechnology; Singh, B. K., Ed.; Dekker: New York, 1999; pp 319-356.
3. Giovanelli, J.; Mudd, S. H.; Datko, A. H. Sulfur amino acids in plants. In The Biochemistry of Plants; Miflin, B. J., Ed.; Academic Press: New York, 1980; Vol. 5, pp 453-505.
4. Hanson, A. D.; Rivoal, J.; Burnet, M.; Rathinasabapathi, B. Biosynthesis of quaternary ammonium and tertiary sulphonium compounds in response to water deficit. In Environment and Plant Metabolism: Flexibility and Acclimation; Smirnoff, N., Ed.; Bios Scientific: Oxford, U.K., 1995; pp 189-198.
5. Bohnert, H. J.; Jensen, R. G. Strategies for engineering water stress tolerance in plants Trends Biotechnol. 1996, 14, 89-97 (Pubitemid 26079508)
6. Yancey, P. H. Organic osmolytes as compatible, metabolic and counteracting cytoprotectants in high osmolarity and other stresses J. Exp. Biol. 2005, 208, 2819-2830 (Pubitemid 41265173)
7. Stret, T. O.; Bolen, D. W.; Rose, G. D. A molecular mechanism for osmollyte-induced protein stability Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13997-14002 (Pubitemid 44488414)
8. Nolte, K. D.; Hanson, A. D.; Gage, D. A. Proline accumulation and methylation to proline betaine in citrus: implications for genetic engineering of stress resistance J. Am. Soc. Hortic. Sci. 1997, 122, 8-13 (Pubitemid 27134293)
9. Arbona, V.; Marco, A. J.; Iglesias, D. J.; Lopez-Climent, M. F.; Talon, M.; Gomez-Cadenas, A. Carbohydrate depletiv in root and leaves of salt-stressed potted Citrus clementina L J. Plant Growth Regul. 2005, 46, 153-160 (Pubitemid 41186253)
10. 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-hydroxyproline betaine J. Agric. Food Chem. 2011, 59, 274-281
11. 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
12. Slow, S.; Donaggio, M.; Cressey, P. J.; Lever, M.; George, P. M.; Chambers, S. T. The betaine content of New Zealand foods and estimated intake in the New Zealand diet J. Food Compos. Anal. 2005, 18, 473-485 (Pubitemid 40277328)
13. Zeisel, S. H.; Mar, M. H.; Howe, J. C.; Holden, J. M. Concentrations of choline-containing compounds and betaine in common foods J. Nutr. 2003, 133, 1302-1307 (Pubitemid 36548698)
14. (Published erratum appears in J. Nutr. 2003, 133, 2918-2919.)
15. Grobbelaar, N.; Steward, F. C. Pipecolic acid in Phaseolus vulgaris: evidence on its derivation from lysine J. Am. Chem. Soc. 1953, 75, 4341-4343
16. Goas, G.; Larher, F.; Goas, M. Mise en evidence de l'acide pipécolique et 5 hydroxypipécolique dans certaines halophytes C. R. Acad. Sci. Paris 1970, 271, 1368-1371
17. Fujita, T.; Hada, T.; Higashino, K. Origin of d-and l -pipecolic acid in human physiological fluids: a study of the catabolic mechanism to pipecolic acid using the lysine loading test Clin. Chim. Acta 1999, 287, 145-156 (Pubitemid 29413016)
18. Kite, G. C.; Ireland, H. Non-protein amino acids of Bocoa (Leguminoseae; Papilinoideae) Phytochemistry 2002, 59, 163-168 (Pubitemid 34123580)
19. Moulin, M.; Deleu, C.; Larher, F.; Bouchereau, A. The lysine-ketoglutarate reductase-saccharopine dehydrogenase is involved in the osmo-induced synthesis of pipecolic acid in rapeseed leaf tissues Plant Physiol. Biochem. 2006, 44, 474-482 (Pubitemid 44540401)
20. Wood, K. V.; Stringham, K. J.; Smith, D. L.; Volienec, J. J.; Hendershot, K. L.; Jackson, K. A.; Rich, P. J.; Yang, W. J.; Rhodes, D. Betaines of alfa: characterization by fast atom bombardment and desorption chemical ionisation mass spectrometry Plant Physiol. 1991, 96, 892-897 (Pubitemid 21914100)
21. Bonham, C. C.; Wood, K. V.; Yang, W. J.; Nadolska-Orczyk, A.; Samaras, Y.; Gage, D. A.; Poupart, J.; Burnet, M.; Hanson, A. D.; Rhodes, D. Identification of quaternary ammonium and tertiary sulfonium compounds by plasma desorption mass spectrometry J. Mass Spectrom. 1995, 30, 1187-1194
22. 13C NMR spektroskopie in der aminosaureana wein und fruchtsaften Z. Lebensm. Unters. 1991, 192, 1-6
23. Robertson, A. V.; Marion, L. The biogenesis of alkaloids. XXV. The role of hygric acid in the biogenesis of stachydrine Can. J. Chem. 1960, 38, 396-398
24. Essery, J. M.; McCaldin, D. J.; Marion, L. The biogenesis of stachydrine Phytochemistry 1962, 1, 209-213
25. Rhodes, D. Personal web page: http://www.hort.purdue.edu/rhodcv/hort640c/ onium/on00008.htm (last accessed Dec 6, 2011).
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. Chen., F. M. F.; Benoiton, N. L. A synthesis of N6,N6,N6-trimethyl- l -lysine dioxalate in gram amounts Biochem. Cell Biol. 1986, 64, 182-183 (Pubitemid 16036406)
28. Wood, K. V.; Bonham, C. C.; Miles, D.; Rothwell, A. P.; Peel, G.; Wood, B. C.; Rhodes, D. Characterization of betaines using electrospray MS/MS Phytochemistry 2002, 59, 759-765 (Pubitemid 34269949)
29. Rogalewicz, F.; Hoppiliard, Y.; Ohanessian, G. Fragmentation mechanisms of α-amino acids protonated under electrospray ionization: a collisional activation and ab initio theoretical study Int. J. Mass Spectrom. 2000, 195/196, 565-590
30. Piraud, M.; Vianey-Saban, C.; Petritis, K.; Elfakir, C.; Steghens, J. P.; Morla, A.; Bouchu, D. ESI-MS/MS analysis of underivatised amino acids: a new tool for the diagnosis of inherited disorders of amino acid metabolism. Fragmentation study of 79 molecules of biological interest in positive and negative ionisation mode Rapid Commun. Mass Spectrom. 2003, 17, 1297-1311 (Pubitemid 36750014)
31. Piraud, M.; Vianey-Saban, C.; Petritis, K.; Elfakir, C.; Steghens, J. P.; Bouchu, D. Ion-pairing reversed-phase liquid chromatography/electrospray ionization mass spectrometric analysis of 76 underivatized amino acids of biological interest: a new tool for diagnosis of inherited disorders of amino acid metabolism Rapid Commun. Mass Spectrom. 2005, 19, 1587-1602 (Pubitemid 40831939)
32. AIJN (Association of the Industry of Juice and Nectars). Code of Practice for Evaluation of Fruit and vegetable Juices: Reference Guide; AIJN: Brussels, Belgium, 1994.
33. van Wandelen, C.; Cohen, S. A. Using quaternary high-performance liquid chromatography eluent systems for separating 6-aminoquinolyl- N -hydroxysuccinimidyl carbamate-derivatized amino acid mixtures J. Chromatogr., A 1997, 763, 11-22 (Pubitemid 27149969)