Dihydrocaffeoyl polyamines (kukoamine and allies) in potato (Solanum tuberosum) tubers detected during metabolite profiling

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 13, 2005, Pages 5461-5466

  Parr, Adrian J ^a   Mellon, Fred A ^a   Colquhoun, Ian J ^a   Davies, Howard V ^b  

^a NORWICH RESEARCH PARK   (United Kingdom)

^b SCOTTISH CROP RESEARCH INSTITUTE   (United Kingdom)

Author keywords

Kukoamine; Metabolite profiling; Polyamine conjugates; Potato; Spermidine; Spermine

Indexed keywords

DRUG DERIVATIVE; KUKOAMINE A; N1,N8 BIS(DIHYDROCAFFEOYL)SPERMIDINE; N1,N8-BIS(DIHYDROCAFFEOYL)SPERMIDINE; POLYAMINE; SPERMIDINE; SPERMINE;

ARTICLE; CHEMISTRY; METABOLISM; PLANT TUBER; POTATO;

PLANT TUBERS; POLYAMINES; SOLANUM TUBEROSUM; SPERMIDINE; SPERMINE;

ARABIDOPSIS; ARABIDOPSIS THALIANA; BETA VULGARIS; BETA VULGARIS SUBSP. VULGARIS; LYCIUM; LYCIUM CHINENSE; LYCOPERSICON ESCULENTUM; NICOTIANA SYLVESTRIS; SOLANUM TUBEROSUM;

EID: 22244458870     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf050298i     Document Type: Article

References (31)

1. Simmonds, M. S. J.; Grayer, R. J. Plant drug discovery and development. In Chemicals from Plants - Perspectives On Plant Secondary Products; Walton, N. J., Brown, D. E., Eds.; Imperial College Press: London, 1999; pp 215-249.
2. Mithen, R. F.; Dekker, M.; Verkerk, R.; Rabot, S.; Johnson, I. T. The nutritional significance, biosynthesis and bioavailability of glucosinolates in human foods. J. Sci. Food Agric. 2000, 80, 967-984.
3. Parr, A. J.; Bolwell, G. P. Phenols in the plant and man - the potential for possible nutritional enhancement of the diet by modifying the phenols content or profile. J. Sci. Food Agric. 2000, 80, 985-1012.
4. Rao, A. V.; Agarwal, S. Role of lycopene as antioxidant carotenoid in the prevention of chronic diseases: A review. Nutr. Res. 1999, 19, 305-323.
5. Fiehn, O.; Kopka, J.; Dörmann, P.; Altmann, T.; Trethewey, R. N.; Willmitzer, L. Metabolite profiling for plant functional genomics. Nat. Biotechnol. 2000, 18, 1157-1161.
6. Fiehn, O. Metabolomics - The link between genotypes and phenotypes. Plant Mol. Biol. 2002, 48, 155-171.
7. Dunn W. B.; Ellis, D. I. Metabolomics: Current analytical platforms and methodologies. TrAC-Trend. Anal. Chem. 2005, 24, 285-294.
8. Stitt, M.; Fernie, A. R. From measurements of metabolites to metabolomics: An 'on the fly' perspective illustrated by recent studies of carbon-nitrogen interactions. Curr. Opin. Biotechnol. 2003, 14, 136-144.
9. Sumner, L. W.; Mendes, P.; Dixon, R. A. Plant metabolomics: Large-scale phytochemistry in the functional genomics era. Phytochemistry 2003, 62, 817-836.
10. Weckwerth, W. Metabolomics in systems biology. Annu. Rev. Plant Biol. 2003, 54, 669-689.
11. Wolfender, J.-L.; Rodriguez, S.; Hostettmann, K. Liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectroscopy for the screening of plant constituents. J. Chromat. A 1998, 794, 299-316.
12. Pham-Tuan, H.; Kaskavelis, L.; Daykin, C. A.; Janssen, H.-G. Method development in high-performance liquid chromatography for high-throughput profiling and metabonomic studies of biofluid samples. J Chromatogr. B 2003, 789, 283-301.
13. Silva Elipe, M. V. Advantages and disadvantages of nuclear magnetic resonance spectroscopy as a hyphenated technique. Anal. Chim. Acta 2003, 497, 1-25.
14. Fiehn, O. Metabolic networks of Cucurbita maxima phloem. Phytochemistry 2003, 62, 875-86.
15. Kell, D. B. Metabolomics and systems biology: Making sense of the soup. Curr. Opin. Microbiol. 2004, 7, 296-307.
16. Defernez, M.; Gunning, Y. M.; Parr, A. J.; Shepherd, L. V. T.; Davies, H. V.; Colquhoun, I. J. NMR and HPLC/UV profiling of potatoes with genetic modifications to metabolic pathways. J. Agric. Food Chem. 2004, 52, 6075-6085.
17. Funayama, S.; Yoshida, K.; Konno, C.; Hikino, H. Structure of kukoamine A, a hypotensive principle of Lycium chinense root barks. Tetrahedron Lett. 1980, 21, 1355-1356.
18. Funayama, S.; Zhang, G. R.; Nozoe, S. Kukoamine-B, a spermine alkaloid from Lycium chinense. Phytochemistry 1995, 38, 1529-1531.
19. Ponasik, J. A.; Strickland, C.; Faerman, C.; Savvides, S.; Karplus, P. A.; Ganem, B. Kukoamine A and other hydrophobic acylpolyamines: Potent and selective inhibitors of Crithidia fasciculata trypanothione reductase. Biochem. J. 1995, 311, 371-375.
20. Brandl W.; Herrmann, K. Uber das Vorkommen der Chlorogensauren in der Kartoffel. Z. Lebensm. Unters. Forsch. 1984, 178, 192-194.
21. Davies, A. M. C. The free amino acids of tubers of potato varieties grown in England and Ireland. Potato Res. 1977, 20, 9-21.
22. Giusti, M. M.; Rodriguez-Saona, L. E.; Griffin, D.; Wrolstad, R. E. Electrospray and tandem mass spectrometry as tools for anthocyanin characterisation. J. Agric. Food Chem. 1999, 47, 4657-4664.
23. Leubner-Metzger, G.; Amrhein, N. The distribution of hydroxycinnamoylputrescines in different organs of Solanum tuberosum and other Solanaceous species. Phytochemistry 1993, 32, 551-556.
24. Lewis, C. E.; Walker, J. R. L.; Lancaster, J. E.; Sutton, K. H. Determination of anthocyanins, flavonoids and phenolic acids in potatoes. I: Coloured cultivars of Solanum tuberosum L. J. Sci. Food Agric. 1998, 77, 45-57.
25. Waterman, P. G.; Mole, S. Analysis of Phenolic Plant Metabolites; Methods in Ecology Series; Blackwell Scientific Publications: London, 1994.
26. Mellon, F. A.; Self, R.; Startin, J. R. Mass Spectrometry of Natural Substances in Foods; Royal Society of Chemistry, Cambridge. 2000.
27. Karigiannis, G.; Mamos, P.; Balayiannis, G.; Katsoulis, I.; Papaioannou, D. Simple fragment syntheses of all four isomers of the spermine alkaloid kukoamine. Tetrahedron Lett. 1998, 59, 5117-5120.
28. Vassis, S.; Karigiannis, G.; Balayiannis, G.; Militsopoulou, M.; Mamos, P.; Francis, G. W.; Papaioannou, D. Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. Tetrahedron Lett. 2001, 42, 1579-1582.
29. Borken, M.; Witte, L.; Wray, V.; Nimtz, M.; Meurer-Grimes, B. Trisubstituted hydroxycinnamic acid spermidines from Quercus dentata pollen. Phytochemistry 1995, 39, 1371-1375.
30. Maga, J. A. Potato glycoalkaloids. Crit. Rev. Food Sci. Nutr. 1980, 12, 371-405.
31. Whitaker, B. D.; Stommel, J. R. Distribution of hydroxycinnamic acid conjugates in fruit of commercial eggplant (Solanum melongena L.) cultivars. J. Agric. Food Chem. 2003, 51, 3448-3454.