Oxidation products of α-farnesene associated with superficial scald development in d'Anjou pear fruits are conjugated trienols

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 9, 2007, Pages 3708-3712

  Whitaker, Bruce D ^a  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

Author keywords

farnesene oxidation; Conjugated trienols; Pear fruit; Pyrus communis; Storage disorder; Superficial scald

Indexed keywords

3,7,11 TRIMETHYLDODECA 1,3,5,10 TETRAEN 7 OL; 3,7,11-TRIMETHYLDODECA-1,3,5,10-TETRAEN-7-OL; ALPHA FARNESENE; ALPHA-FARNESENE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; FOOD PRESERVATION; FRUIT; OXIDATION REDUCTION REACTION; PEAR;

FOOD PRESERVATION; FRUIT; OXIDATION-REDUCTION; PYRUS; SESQUITERPENES;

MALUS X DOMESTICA; PYRUS; PYRUS COMMUNIS;

EID: 34249322677     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf063710i     Document Type: Article

References (25)

1. Bain, J. M.; Mercer, F. J. The submicroscopic cytology of superficial scald, a physiological disease of apples. Aust. J. Biol. Sci. 1963, 16, 442-449.
2. Huelin, F. E.; Coggiola, I. M. Superficial scald, a functional disorder of stored apples. VII. Effect of applied α-farnesene, temperature and diphenylamine on scald and the concentration and oxidation of α-farnesene in the fruit. J. Sci. Food Agric. 1970, 21, 584-589.
3. Anet, E. F. L. J. Superficial scald, a functional disorder of stored apples. IX. Effect of maturity and ventilation. J. Sci. Food Agric. 1972, 23, 763-769.
4. Chen, P. M.; Varga, D. M.; Mielke, E. A.; Facteau, T. J.; Drake, S. R. Control of superficial scald on 'd'Anjou' pears by ethoxyquin: Oxidation of α-farnesene and its inhibition. J. Food Sci. 1990, 55, 171-175, 180.
5. Rowan, D. D.; Hunt, M. B.; Fielder, S.; Norris, J.; Sherburn, M. S. Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples. J. Agric. Food Chem. 2001, 49, 2780-2787.
6. Lurie, S.; Lers, A.; Shacham, Z.; Sonego, L.; Burd, S.; Whitaker, B. Expression of α-farnesene synthase AFS1 and 3-hydroxy-3- methylglutaryl coenzyme A reductase HMG2 and HMG3 in relation to α-farnesene and conjugated trienols in 'Granny Smith' apples heat or 1-MCP treated to prevent superficial scald. J. Am. Soc. Hortic. Sci. 2005, 130, 232-236.
7. Pechous, S. W.; Watkins, C. B.; Whitaker, B. D. Expression of α-farnesene synthase gene AFS1 in relation to levels of α-farnesene and conjugated trienols in peel tissue of scald-susceptible 'Law Rome' and scald-resistant 'Idared' apple fruit. Postharvest Biol. Technol. 2005, 35, 125-132.
8. Gapper, N. E.; Bai, J.; Whitaker, B. D. Inhibition of ethylene-induced α-farnesene synthase gene PcAFS1 expression in 'd'Anjou' pears with 1-MCP reduces synthesis and oxidation of α-farnesene and delays development of superficial scald. Postharvest Biol. Technol. 2006, 41, 225-233.
9. Huelin, F. E.; Coggiola, I. M. Superficial scald, a functional disorder of stored apples. IV. Effect of variety, maturity, oiled wraps and diphenylamine on the concentration of α-farnesene in the fruit. J. Sci. Food Agric. 1968, 19, 297-301.
10. Whitaker, B. D.; Solomos, T.; Harrison, D. J. Quantification of α-farnesene and its conjugated trienol oxidation products from apple peel by C18-HPLC with UV detection. J. Agric. Food. Chem. 1997, 45, 760-765.
11. Bai, J. Comparison of CA, 1-MCP and ethoxyquin treatments in altering α-farnesene metabolism and reducing superficial scald of 'd'Anjou' pears. Acta Hortic. 2007, in press.
12. Rowan, D. D.; Allen, J. M.; Fielder, S.; Spicer, J. A.; Brimble, M. A. Identification of conjugated triene oxidation products of α-farnesene in apple skin. J. Agric. Food Chem. 1995, 43, 2040-2045.
13. Anet, E. F. L. J. Autoxidation of α-farnesene. Aust. J. Chem. 1969, 22, 2403-2410.
14. Whitaker, B. D. Oxidative stress and superficial scald of apple fruit. HortScience 2004, 39, 12-16.
15. Brimble, M. A.; Rowan, D. D.; Spicer, J. A. Synthesis of conjugated trienes and related oxidation products of α-farnesene. Aust. J. Chem. 1994, 47, 1979-1988.
16. Krings, U.; Hardebusch, B.; Albert, D.; Berger, R. G.; Maróstica, M., Jr.; Pastore, G. M. Odor-active alcohols from the fungal transformation of α-farnesene. J. Agric. Food Chem. 2006, 54, 9079-9084.
17. Rueda, A.; Zubía, E.; Ortega, M. J.; Salvá, J. New acyclic sesquiterpenes and norsesquiterpenes from the Caribbean gorgonian Plexaurella grisea. J. Nat. Prod. 2001, 64, 401-405.
18. Fielder, S.; Rowan, D. D.; Sherburn, M. S. Synthesis of sesquiterpene polyene hydroperoxides by region- and stereoselective transposition reactions. Tetrahedron 1998, 54, 1290712922.
19. Whitaker, B. D.; Saftner, R. A. Temperature-dependent autoxidation of conjugated trienols from apple peel yields 6-methyl-5-hepten-2-one, a volatile implicated in induction of scald. J. Agric. Food Chem. 2000, 48, 2040-2043.
20. Anet, E. F. L. J. Superficial scald, a functional disorder of stored apples. VIII. Volatile products of the autoxidation of α-farnesene. J. Sci. Food Agric. 1972, 23, 605-608.
21. Mir, N. A.; Perez, R.; Beaudry, R. M. A poststorage burst of 6-methyl-5-hepten-2-one (MHO) may be related to superficial scald development in 'Cortland' apples. J. Am. Soc. Hortic. Sci. 1999, 124, 173-176.
22. Wang, Z.; Dilley, D. R. Hypobaric storage removes scald-related volatiles during the low temperature induction of superficial scald of apples. Postharvest Biol. Technol. 2000, 18, 191-199.
23. Eshdat, Y.; Holland, D.; Faltin, Z.; Ben-Hayyim, G. Plant glutathione peroxidases. Physiol. Plant 1997, 100, 234-240.
24. Frova, C. The plant glutathione transferase gene family: Genomic structure, functions, expression and evolution. Physiol. Plant 2003, 119, 469-479.
25. Du, Z.; Bramlage, W. J. A modified hypothesis on the role of conjugated trienes in superficial scald development on stored apples. J. Am. Soc. Hortic. Sci. 1993, 118, 807-813.