Involvement of ethylene in the accumulation of esculeoside a during fruit ripening of tomato (solanum lycopersicum)

Journal of Agricultural and Food Chemistry

Volumn 57, Issue 8, 2009, Pages 3247-3252

  Iijima, Yoko ^a,b,c   Fujiwara, Yukio ^a,b,c   Tokita, Takeaki ^a,b,c   Ikeda, Tsuyoshi ^a,b,c   Nohara, Toshihiro ^a,b,c   Aoki, Koh ^a,b,c   Shibata, Daisuke ^a,b,c  

^a KAZUSA DNA RESEARCH INSTITUTE   (Japan)

^b KUMAMOTO UNIVERSITY   (Japan)

^c SOJO UNIVERSITY   (Japan)

Author keywords

Esculeoside A; Ethylene; Glycoalkaloids; R tomatine; Ripening; Solanaceae; Solanum lycopersicum; Tomato

Indexed keywords

ALPHA-TOMATINE; DRUG DERIVATIVE; ESCULEOSIDE A; ETHYLENE; ETHYLENE DERIVATIVE; SAPOGENIN; TOMATINE;

ARTICLE; DRUG EFFECT; FRUIT; GENETICS; GROWTH, DEVELOPMENT AND AGING; METABOLISM; MUTATION; TOMATO;

ETHYLENES; FRUIT; LYCOPERSICON ESCULENTUM; MUTATION; SAPOGENINS; TOMATINE;

LYCOPERSICON ESCULENTUM; MAGNOLIOPHYTA; SOLANACEAE; SOLANUM;

EID: 65349181863     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8037902     Document Type: Article

References (40)

1. Friedman, M. Analysis of biologically active compounds in potatoes {Solarium tuberosum), tomatoes (Lycopersicon esculen-tum), and jimson weed {Datura stramonium) seeds. J. Chro-matoer. A 2004, 1054, 143-155.
2. Friedman, M. Potato glycoalkaloids and metabolites: Roles in the plant and in the diet. J. Agric. Food Chem. 2006, 54, 8655-8681.
3. Nohara, T.; Ikeda, T.; Fujiwara, Y.; Matsushita, S.; Noguchi, E.; Yoshimitsu, H.; Ono, M. Physiological functions of solanaceous and tomato steroidal glycosides. J. Nat. Med. 2007, 61, 1-13.
4. Vaananen, T.; Ikonen, T.; Rokka, V. M.; Kuronen, P.; Serimaa, R.; Ollilainen, V. Influence of incorporated wild Solarium genomes on potato properties in terms of starch nanostructure and glycoal-kaloid content. J. Agric. Food Chem. 2005, 53, 5313-5325.
5. Friedman, M. Tomato glycoalkaloids: Role in the plant and in the diet. J. Agric. Food Chem. 2002, 50, 5751-5780.
6. Lee, K. R.; Kozukue, N; Han, J. S.; Park, J. H.; Chang, E. Y.; Baek, E. J.; Chang, J. S.; Friedman, M. Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. J. Agric. Food Chem. 2004, 52, 2832-2839.
7. Friedman, M.; Lee, K. R.; Kim, H. J.; Lee, I. S.; Kozukue, N. Anticarcinogenic effects of glycoalkaloids from potatoes against human cervical, liver, lymphoma, and stomach cancer cells. J. Aerie. Food Chem. 2005, 53, 6162-6169.
8. Thorne, H. V.; Clarke, G. F.; Skuce, R. The inactivation of herpes simplex virus by some Solanaceae glycoalkaloids. Antiviral Res. 1985, 5, 335-343.
9. Friedman, M.; Fitch, T. E.; Yokoyama, W. E. Lowering of plasma LDL cholesterol in hamsters by the tomato glycoalkaloid tomatine. Food Chem. Toxicol. 2000, 38, 549-553.
10. Friedman, M.; McDonald, G. M. Postharvest changes in glycoalkaloid content of potatoes. Adv. Exp. Med. Biol. 1999, 459, 121-143.
11. Grunenfelder, L. A.; Knowles, L. O.; HiUer, L. K.; Knowles, N. R. Glycoalkaloid development during greening of fresh market potatoes (Solanum tuberosum L.). J. Agric. Food Chem. 2006, 54, 5847-5854.
12. Friedman, M.; Levin, C. E. Dehydrotomatine content in tomatoes. J. Agric. Food Chem. 1998, 46, 4571-4576.
13. Kozukue, N; Han, J. S.; Lee, K. R.; Friedman, M. Dehydrotomatine and a-tomatine content in tomato fruits and vegetative plant tissues. J. Agric. Food Chem. 2004, 52, 2079-2083.
14. Sander, H. The formation and degradation of tomatine in the tomato plant. Planta 1956, 47, 374-400.
15. Ali, A.; Schloesser, E. Tomatine content of plant parts of tomatoes at different stages of development. Angew. Bot. 1977, 51, 143- 148.
16. Eltayeb, E.; Roddick, J. Biosynthesis and degradation of a-tomatine in developing tomato fruits. Phvtochemistrv 1984, 24, 253-257.
17. Eltayeb, E.; Roddick, J. Changes in the alkaloid content of developing fruits of tomato (Lycopersicon esculentum Mill.): I. Analyses of cultivars and mutants with different ripening characteristics. J. Exv. Bot. 1984, 35, 252-260.
18. Yahara, S.; Uda, N; Nohara, T. Lycoperoside A-C, three stereoisomeric 23-acetoxyspirosolan-3β-ol β-lycotetraosides from Lycopersicon esculentum. Phvtochemistrv 1996, 42, 169-172.
19. Yahara, S.; Uda, N; Yoshio, E.; Yae, E. Steroidal alkaloid glycosides from tomato (Lycopersicon esculentum). J. Nat. Med. 2004, 67, 500-502.
20. Fujiwara, Y.; Takai, A.; Uehara, Y.; Ikeda, T.; Okawa, M.; Yamauchi, K; Ono, M.; Yoshimitsu, H; Nohara, T. Tomato steroidal alkaloid glycosides, esculeosides A and B, from ripe fruits. Tetrahedron 2004, 60, 4915-4920.
21. Fujiwara, Y.; Yahara, S.; Ikeda, T.; Ono, M.; Nohara, T. Cytotoxic major saponin from tomato fruits. Chem. Pharm. Bull. 2003, 51, 234-235.
22. Iijima, Y.; Nakamura, Y.; Ogata, Y.; Tanaka, K.; Sakurai, N; Suda, K; Suzuki, T.; Suzuki, H.; Okazaki, K.; Kitayama, M.; Kanaya, S.; Aoki, K; Shibata, D. Metabolite annotations based on the integration of mass spectral information. Plant J. 2008, 54, 949-962.
23. Mintz-Oron, S.; Mandel, T.; Rogachev, I.; Feldberg, L.; Lotan, O.; Yativ, M.; Wang, Z.; Jetter, R.; Venger, I.; Adato, A.; Aharoni, A. Gene expression and metabolism in tomato fruit surface tissues. Plant Phvsiol. 2008, 147, 823-851.
24. Alexander, L.; Grierson, D. Ethylene biosynthesis and action in tomato: A model for climacteric fruit ripening. J. Exp. Bot. 2002, 53, 2039-2055.
25. Carrari, F.; Fernie, A. R. Metabolic regulation underlying tomato fruit development. J. EXP. Bot. 2006, 57, 1883-1897.
26. Tigchelaar, E. C; McGlasson, W. B.; Buescher, R. W. Genetic regulation of tomato fruit ripening. Gartenbauwissenschaft 1978, 13, 508-513.
27. Vrebalov, J.; Ruezinsky, D.; Padmanabhan, V.; White, R.; Medrano, D.; Drake, R.; Schuch, W.; Giovannoni, J. A MADS-box gene necessary for fruit ripening at the tomato ripening-inhibitor (rin) locus. Science 2002, 296, 343-346.
28. Lincoln, J. E.; Fischer, R. L. Regulation of gene expression by ethylene in wild-type and rin tomato (Lycopersicon esculentum) fruit. Plant Phvsiol. 1988, 88, 370-374.
29. Giovannoni, J. J. Genetic regulation of fruit development and ripening. Plant Cell 2004, 16, S170-S180.
30. Wilkinson, J. Q.; Lanahan, M. B.; Yen, H. C; Giovannoni, J. J.; Klee, H. J. An ethylene-inducible component of signal transduction encoded by never-ripe. Science 1995, 270, 1807-1809.
31. Alba, R.; Payton, P.; Fei, Z.; McQuinn, R.; Debbie, P.; Martin, G. B.; Tanksley, S. D.; Giovannoni, J. J. Transcriptome and selected metabolite analyses reveal multiple points of ethylene control during tomato fruit development. Plant Cell 2005, 17, 2954-2965.
32. Iijima, Y.; Suda, K.; Suzuki, T.; Aoki, K.; Shibata, D. Metabolic profiling of chalcones and flavanones in tomato fruit. J. Jpn. SOC. Hortic. Sci. 2007, 77, 94-102.
33. Eltayeb, E.; Roddick, J. Changes in the alkaloid content of developing fruits of tomato (Lycopersicon esculentum Mill.): II. J. EXD. Bot. 1984, 35, 261-267.
34. Moore, S.; Vrebalov, J.; Payton, P.; Giovannoni, J. Use of genomics tools to isolate key ripening genes and analyse fruit maturation in tomato. J. Exp. Bot. 2002, 53, 2023-2030.
35. Moco, S.; Capanoglu, E.; Tikunov, Y.; Bino, R. J.; Boyacioglu, D.; Hall, R. D.; Vervoort, J.; De Vos, R. C. Tissue specialization at the metabolite level is perceived during the development of tomato fruit. J. Exp. Bot. 2007, 58, 4131-4146.
36. Yamanaka, T.; Vincken, J. P.; de Waard, P.; Sanders, M.; Takada, N.; Gruppen, H. Isolation, characterization, and surfactant properties of the major triterpenoid glycosides from unripe tomato fruits. J. Agric. Food Chem. 2008, 56, 11432-11440.
37. Cataldi, T. R.; Lelario, F.; Bufo, S. A. Analysis of tomato glycoalkaloids by liquid chromatography coupled with electro-spray ionization tandem mass spectrometry. Rapid Commun. Mass S?ectrom. 2005, 19, 3103-3110.
38. Heftmann, E.; Schwimmer, S. Degradation of tomatine to 3ß-hydroxy-5a-pregn-16-en-20-one by ripe tomatoes. Phvtochemistrv 1972, 11, 2783-2787.
39. Fujiwara, Y.; Yoshizaki, M.; Matsushita, S.; Yahara, S.; Yae, E.; Ikeda, T.; Ono, M.; Nohara, T. A new tomato pregnane glycoside from the overripe fruits. Chem. Pharm. Bull. 2005, 53, 584-585.
40. Fujiwara, Y.; Kiyota, N.; Hori, M.; Matsushita, S.; Iijima, Y.; Aoki, K.; Shibata, D.; Takeya, M.; Ikeda, T.; Nohara, T.; Nagai, R. Esculeogenin A, a new tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in ApoE-deficient mice by inhibiting ACAT. Arterioscler. Thromb. Vasc. Biol. 2007, 27, 2400-2406.