Biosynthetic mechanism of 2-acetyl-1-pyrroline and its relationship with Δ1-pyrroline-5-carboxylic acid and methylglyoxal in aromatic rice (Oryza sativa L.) callus

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 16, 2008, Pages 7399-7404

  Huang, Tzou Chi ^a   Teng, Chia Shih ^a   Chang, Jia Lin ^a   Chuang, Hui Su ^a   Ho, Chi Tang ^b   Wu, Mei Li ^a  

^a NATIONAL PINGTUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

1 pyrroline 5 carboxylic acid; 2 acetyl 1 pyrroline; Aromatic rice; Biosynthetic pathway; Methylglyoxal

Indexed keywords

2 ACETYL 1 PYRROLINE; 2-ACETYL-1-PYRROLINE; DELTA 1 PYRROLINE 5 CARBOXYLATE; DELTA-1-PYRROLINE-5-CARBOXYLATE; METHYLGLYOXAL; PYRROLE DERIVATIVE;

ARTICLE; CHEMISTRY; ENZYMOLOGY; METABOLISM; ODOR; PLANT SEED; RICE;

ODORS; ORYZA SATIVA; PYRROLES; PYRUVALDEHYDE; SEEDS;

ORYZA SATIVA;

EID: 51649118419     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8011739     Document Type: Article

References (29)

1. Pinson, S. R. M. Inheritance of aroma in six rice cultivars. Crop Sci. 1994, 34, 1151-1157.
2. Buttery, R. G.; Ling, L. C.; Juliano, B. O.; Turnbaugh, J. G. Cooked rice aroma and 2-acetyl-1-pyrroline. J. Agric. Food Chem. 1983, 31, 823-828.
3. Yoshihashi, T. N.; Huong, T. T.; Inatomi, H. Precursors of 2-acetyl-1-pyrroline, a potent flavor compound of an aromatic rice variety. J. Agric. Food Chem. 2002, 50, 2001-2004.
4. Siddiq, E. A.; Sadananda, A. R.; Zaman, F. U. Use of primary trisomic of rice in genetic analysis. Rice Genetics, Proceedings of the International Rice Genetics Symposium, International Rice Research Institute, Manila, Philippines, 1986; pp 185-197.
5. Tomar, J. B.; Prassad, S. C. Genetic analysis of aroma in rice landraces. Oryza 1997, 34, 191-195.
6. Yano, M.; Shimosaka, E.; Sato, A.; Nakagahra, M. Linkage analysis of a gene for scent in indica rice variety, Surjamkhi, using restriction fragment length polymorphism makers (in Japanese). Jpn. J. Breed. 1991, 41, 338-339.
7. Ahn, S. N.; Bollich, C. N.; Tanksley, S. D. RFLP tagging of a gene for aroma in rice. Theor. Appl. Genet. 1992, 84, 825-828.
8. Lorieux, M.; Petrov, M.; Huang, N.; Guiderdoni, E.; Ghesquière, A. Aroma in rice: genetic analysis of a quantitative trait. Theor. Appl. Genet. 1996, 93, 1145-1151.
9. Münch, P.; Hofmann, T.; Schieberle, P. Comparison of key odorants generated by thermal treatment of commercial and self-prepared yeast extracts: influence of the amino acid composition on odorant formation. J. Agric. Food Chem. 1997, 45, 1338-1344.
10. Romanczyk, L. J.; McClell, C. A.; Post, L. S.; Aitken, W. M. Formation of 2-acetyl-1-pyrroline by several Bacillus cereus strains isolated from cocoa fermentation boxes. J. Agric. Food Chem. 1995, 43, 469-475.
11. Thimmaraju, R.; Bhagyalakshmi, N.; Narayan, M. S.; Venkatachalam, L.; Ravishankar, G. A. In vitro culture of Pandanus amaryllifolius and enhancement of 2-acetyl-1-pyrroline, the major flavouring compound of aromatic rice, by precursor feeding of L-proline. J. Sci. Food Agric. 2005, 85, 2527-2534.
12. Suprasanna, P.; Ganapathi, T. R.; Ramaswamy, N. K.; Surendranathan, K. K.; Rao, P. S. Aroma synthesis in cell and callus cultures of rice. In Rice Genetics, Proceedings of the International Rice Genetics Symposium, International Rice Research Institute, 1998; Vol. 15, pp 123-125.
13. Iyer, S.; Caplan, A. Products of proline catabolism can induce osmotically regulated genes in rice. Plant Physiol. 1998, 116, 203-211.
14. Hellmann, H.; Funck, D.; Rentsch, D.; Frommer, W. B. Hypersensitivity of an Arabidopsis sugar signaling mutant toward exogenous proline application. Plant Physiol. 2000, 123, 779-789.
15. Nomura, M.; Takagi, H. Role of the yeast acetyltransferase Mpr1 in oxidative stress: Regulation of oxygen reactive species caused by a toxic proline catabolism intermediate. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 12616-12621.
16. Maxwell, S. A.; Davis, G. E. Differential gene expression in p53-mediated apoptosis-resistant vs. apoptosis-sensitive tumor cell lines. Proc. Natl. Acad. Sci U. S. A. 2000, 97, 13009-13014.
17. 1-Pyrroline-5-carboxylic acid formed by proline dehydrogenase from the Bacillus subtilis ssp. natto expressed in Escherichia coli as a precursor for 2-acetyl-1-pyrroline. J. Agric. Food Chem. 2007, 55, 5097-5102.
18. Chu, C. C.; Wang, C. S.; Sun, C. C.; Hiu, C.; Yin, K. C.; Chu, C. Y. Establishment of an efficient medium for anther culture of rice through comparative experiment on the nitrogen source. Sci. Sin. 1975, 18, 659-668.
19. O'Donnell, J. J.; Sandman, R. P.; Martin, S. R. Assay of ornithine aminotransferase by high-performance liquid chromatography. Anal. Biochem. 1978, 90, 41-46.
20. Cordeiro, C.; Ponces Freire, A. Methylglyoxal assay in cells as 2-methylquinoxaline using 1,2-diaminobenzene as derivatizing reagent. Anal. Biochem. 1996, 234, 221-224.
21. Scarpulla, R. C.; Soffer, R. L. Membrane-bound proline dehydrogenase from Escherichia coli solubilization, purification, and characterization. J. Biol. Chem. 1978, 253, 5997-6001.
22. Mezl, V. A.; Knox, W. E. Properties and analysis of a stable derivative of pyrroline-5-carboxylic acid for use in metabolic studies. Anal. Biochem. 1976, 74, 430-440.
23. 1-pyrolline-5- carboxylate synthetase gene properties in three rice cultivars differing in salinity and drought tolerance. Plant Sci. 2003, 165, 1059-1068.
24. 1-pyrolline-5- carboxylate synthetase and correlation between the expression of the gene and salt tolerance in Oryza sativa L. Plant Mol. Biol. 1997, 33, 857-865.
25. Hur, J.; Jung, K. H.; Lee, C. H.; An, G. H. Stress-inducible OsP5CS2 gene is essential for salt and cold tolerance in rice. Plant Sci. 2004, 167, 417-426.
26. Yoshihashi, T.; Nguyen, T. T. H.; Kabaki, N. Area dependency of 2-acetyl-1-pyrroline content in an aromatic rice variety, Khao Dawk Mali 105. JARQ 2004, 38, 105-109.
27. Kavi Kishor, P. B.; Sangams, S.; Amrutha, R. N.; Srilaxmi, P.; Naidu, K. R.; Rao, K. R. S. S.; Rao, S.; Reddy, K. J.; Theriappan, P.; Sreenivasulu, N. Regulation of proline biosynthesis, degradation, uptake and transport in higher plants: Its implications in plant growth and abiotic stress tolerance. Curr. Sci. 2005, 88, 424-438.
28. Wu, M. L.; Chen, J. H.; Ho, C. T.; Huang, T. C. Synthesis of 1-piperideine-6-carboxylic acid produced by L-lysine-ε- aminotransferase from the Streptomyces clvuligerus gene expressed in Escherichia coli. J. Agric. Food Chem. 2007, 55, 1767-1772.
29. Schieberle, P. The role of free amino acids present in yeast as precursors of the odorants 2-acetyl-1-pyrroline and 2-acetyltetrahydropyridine in wheat bread crust. Z. Lebensm. - Unters. Forsch. 1990, 191, 206-209.