Formation of damascenone derived from glycosidically bound precursors in green tea infusions

Food Chemistry

Volumn 123, Issue 3, 2010, Pages 601-606

  Kinoshita, Tomomi ^a   Hirata, Satoshi ^a   Yang, Ziyin ^a   Baldermann, Susanne ^a   Kitayama, Emiko ^a   Matsumoto, Shigetaka ^a   Suzuki, Masayuki ^a   Fleischmann, Peter ^b   Winterhalter, Peter ^b   Watanabe, Naoharu ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Damascenone; Glycosides; Green tea; Precursor

Indexed keywords

3 HYDROXY 7,8 DIDEHYDRO B IONOL; 3 O BETA DELTA GLUCOPYRANOSYL 3 HYDROXY 7,8 DIDEHYDRO BETA IONOL; 3 O BETA DELTA GLUCOPYRANOSYL MEGASTIGMA 6,7 DIEN 3,5,9 TRIOL; 9 O BETA DELTA GLUCOPYRANOSYL 3 HYDROXY 7,8 DIDEHYDRO BETA IONOL; 9 O BETA DELTA GLUCOPYRANOSYL MEGASTIGMA 6,7 DIEN 3,5,9 TRIOL; AGLYCONE; BETA DELTA GLUCOSYL; DAMASCENONE; FLAVORING AGENT; GLYCOSIDE; MEGASTIGMA 6,7 DIEN 3,5,9 TRIO; UNCLASSIFIED DRUG;

ARTICLE; BIOCHEMICAL COMPOSITION; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; DEHYDRATION; FRACTIONATION; GLYCOSIDATION; HEATING; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH TEMPERATURE; HYDROLYSIS; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NONHUMAN; PH; PHYTOCHEMISTRY; PRECURSOR; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY; TEA;

EID: 77954622147     PISSN: 03088146     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.foodchem.2010.04.077     Document Type: Article

References (23)

1. Baderschneider B., Skouroumounis G., Winterhalter P. Isolation of two glucosidic precursors of β-damascenone from Riesling wine. Natural Product Letters 1997, 10:111-114.
2. Bezman Y., Bilkis I., Winterhalter P., Fleischmann P., Rouseff R.L., Baldermann S., et al. Thermal oxidation of 9'-cis-neoxanthin in a model system containing peroxyacetic acid leads to the potent odorant β-damascenone. Journal of Agricultural and Food Chemistry 2005, 53:9199-9206.
3. Buttery R.G., Teranishi R., Ling L.C. Fresh tomato aroma volatiles: A quantitative study. Journal of Agricultural and Food Chemistry 1987, 35:540-544.
4. Buttery R.G., Teranishi R., Ling L.C., Turnbaugh J.G. Quantitative and sensory studies on tomato paste volatiles. Journal of Agricultural and Food Chemistry 1990, 38:336-340.
5. Chevance F., Guyot-Declerck C., Dupont J., Collin S. Investigation of the β-damascenone level in fresh and aged commercial beers. Journal of Agricultural and Food Chemistry 2002, 50:3818-3821.
6. 13-norisoprenoid precursors. Journal of Agricultural and Food Chemistry 2005, 53:6777-6783.
7. Demole E., Enggist P., Säuberli U., Stoll M., Kováts E.S. Structure and synthesis of damascenone [2,6,6-trimethyl-1-trans-crotonyl-1,3-cyclohexadiene], odorous constituent of Bulgarian rose oil (Rosa damascena). Helvetica Chimica Acta 1970, 53:541-551.
8. Huang F.C., Horváth G., Molnár P., Turcsi E., Deli J., Schrader J., et al. Substrate promiscuity of RdCCD1, a carotenoid cleavage oxygenase from Rosa damascena. Phytochemistry 2009, 70:457-464.
9. Isoe S., Katsumura S., Sakan T. The synthesis of damascenone and β-damascone and the possible mechanism of their formation from carotenoids. Helvetica Chimica Acta 1973, 56:1514-1516.
10. Kotseridis Y., Baumes R.L., Skouroumounis G.K. Quantitative determination of free and hydrolytically liberated β-damascenone in red grapes and wines using a stable isotope dilution assay. Journal of Chromatography A 1999, 849:245-254.
11. Kumazawa K., Masuda H. Identification of potent odorants in Japanese green tea (Sen-cha). Journal of Agricultural and Food Chemistry 1999, 47:5169-5172.
12. Kumazawa K., Masuda H. Change in the flavor of black tea drink during heat processing. Journal of Agricultural and Food Chemistry 2001, 49:3304-3309.
13. Masuda H. Flavor stability of tea drinks. Tea and tea products: Chemistry and health-promoting properties 2008, 275-300. CRC Press Taylor & Francis Group, Boca Raton. C.T. Ho, J.K. Lin, F. Shahidi (Eds.).
14. Näf R., Velluz A., Thommen W. Isolation of a glucosidic precursor of damascenone from Lycium halimifolium Mill. Tetrahedron Letters 1990, 31:6521-6522.
15. Puglisi C.J., Elsey G.M., Prager R.H., Skouroumounis G.K., Sefton M.A. Identification of a precursor to naturally occurring β-damascenone. Tetrahedron Letters 2001, 42:6937-6939.
16. Roberts D., Morehai A.P., Acree T.E. Detection and partial characterization of eight β-damascenone precursors in apples (Malus domestica Borkh. Cv. Empire). Journal of Agricultural and Food Chemistry 1994, 42:345-349.
17. Shure K.B., Acree T.E. Changes in the odor-active compounds in Vitis labruscana Cv. Concord during growth and development. Journal of Agricultural and Food Chemistry 1994, 42:350-353.
18. Skouroumounis G.K., Massy-Westropp R.A., Sefton M.A., Williams P.J. Precursors of damascenone in fruit juices. Tetrahedron Letters 1992, 33:3533-3536.
19. Skouroumounis G.K., Sefton M.A. Acid-catalyzed hydrolysis of alcohols and their β-d-glucopyranosides. Journal of Agricultural and Food Chemistry 2000, 48:2033-2039.
20. Straubinger M., Knapp H., Oka N., Watanabe N., Winterhalter P. Isolation of glucosidic β-damascenone precursor from rose petals. Journal of Agricultural and Food Chemistry 1997, 45:4053-4056.
21. Suzuki M., Matsumoto S., Mizoguchi M., Hirata S., Takagi K., Hashimoto I., et al. Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-β-d-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill. Bioscience, Biotechnology and Biochemistry 2002, 66:2692-2697.
22. Winterhalter P., Skouroumounis G.K. Glycoconjugated aroma compounds: Occurrence, role and biotechnological transformation. Advances in biochemical engineering/biotechnology (Vol. 55). Biotechnology of aroma compounds 1997, 73-105. Springer, Berlin, Heidelberg. R.G. Berger (Ed.).
23. Yamano Y., Watanabe Y., Watanabe N., Ito M. Stereocontrolled synthesis of glucosidic damascenone precursors. Journal of the Chemical Society, Perkin Transactions 1 2002, 2833-2844.