Conversion of citronellyl diphosphate and citronellyl β-D-glucoside into rose oxide by Pelargonium graveolens

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 4, 1999, Pages 1668-1672

  Wüst, Matthias ^a   Beck, Thomas ^a   Mosandl, Armin ^a  

^a GOETHE UNIVERSITY   (Germany)

Author keywords

Citronellyl D glucoside; Citronellyl diphosphate; Geraniaceae; Monoterpenes; Pelargonium graveolens; Rose oxide; Stable isotope labeling

Indexed keywords

DEUTERIUM; GLUCOSIDE; TERPENE; TERPENE DERIVATIVE; VOLATILE AGENT;

ARTICLE; GLYCOSYLATION; MASS FRAGMENTOGRAPHY; METABOLISM; NONHUMAN; PHOSPHORYLATION; PHYTOCHEMISTRY; PLANT; STEREOISOMERISM;

DEUTERIUM; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLUCOSIDES; PLANTS; STEREOISOMERISM; TERPENES;

GERANIACEAE; PELARGONIUM GRAVEOLENS;

EID: 0042058195     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980972e     Document Type: Article

References (19)

1. Bunton, C. A.; Hachey, D. L.; Leresche, J.-P. Deamination of Nerylamine and Geranylamine. J. Org. Chem. 1972, 37, 4036-4039.
2. Chubinidze, V. V.; Beriashvili, T. V.; Chubinidze, D. V. Metabolism of Volatile Oil and Citronellol in Geranium (Pelargonium roseum L.). Biochemistry (Moscow) 1993, 58, 591-595.
3. Croteau, R. Biosynthesis and Catabolism of Monoterpenes. Chem. Rev. 1987, 87, 929-954.
4. Croteau, R. In A World Perspective. Flavors and Fragrances; Lawrence, B. M., Mookherjee, B. D., Willis, B. J., Eds.; Elsevier Science Publishers: Amsterdam, The Netherlands, 1988; p 65-84.
5. Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. Phosphorylation of Isoprenoid Alcohols. J. Org. Chem. 1986, 51, 4768-4779.
6. Francis, M. J. O.; Allock, C. Geraniol β-D-glucoside; Occurrence and Synthesis in Rose Flowers. Phytochemistry 1969, 8, 1339-1347.
7. Günata, Y. Z.; Bayonove, C. L.; Tapiero, C.; Cordonnier, R. E. Hydrolysis of Grape Monoterpenyl β-D-Glucosides by various β-Glucosidases. J. Agric. Food Chem. 1990, 38, 1232-1236.
8. King, R. W.; Zeevaart, J. A. D. Enhancement of Phloem Exudation from Cut Petioles by Chelating Agents. Plant Physiol. 1974, 53, 96-103.
9. Matucha, M.; Jockisch, W.; Verner, P.; Anders, G. Isotope effect in gas-liquid chromatography of labelled compounds. J. Chromatogr. 1991, 588, 251-258.
10. Ney, I.; Jäger, E.; Herderich, M.; Schreier, P.; Schwab, W. Analysis of Phosphorylated Terpenes by Electrospray Ionization Liquid Chromatography-Tandem Mass Spectrometry. Phytochem. Anal. 1996, 7, 233-236.
11. Paulsen, H.; Lê-Nguyên, B.; Sinnwell, V.; Heemann, V.; Seehofer, F. Synthese von Glycosiden von Mono-, Sesquiund Diterpenalkoholen. Liebigs Ann. Chem. 1985, 1513-1536.
12. Schwab, W. Ph.D. Thesis, University of Würzburg, Germany, 1989.
13. Stahl-Biskup, E. Glycosidically bound Volatiles - A Review 1986-1991. Flavour Fragrance J. 1987, 2, 75-82.
14. Stahl-Biskup, E.; Intert, F.; Holthuijzen, J.; Stengele, M.; Schulz, G. Monoterpene Glycosides, State-of-the-Art. Flavour Fragrance J. 1993, 8, 61-80.
15. Winterhalter, P.; Skouroumounis, G. K. In Biotechnology of Aroma Compounds; Berger, R. G., Ed.; Springer-Verlag, Berlin, 1997; pp 73-105.
16. Wüst, M.; Beck, T.; Dietrich, A.; Mosandl, A. On the Biogenesis of Rose Oxide in Pelargonium graveolens L'Héritier and Pelargonium radens H.E. Moore. Enantiomer 1996, 1, 167-176.
17. Wüst, M.; Rexroth, A.; Beck, T.; Mosandl, A. Mechanistic Aspects of the Biogenesis of Rose Oxide in Pelargonium graveolens L'Héritier. Chirality 1998a, 9, 229-238.
18. Wüst, M.; Beck, T.; Mosandl, M. Biogenesis of Geranium Oil Compounds: On the Origin of Oxygen in cis-/trans-Rose Oxide. J. Agric. Food Chem. 1998b, 46, 3225-3229.
19. Wüst, M.; Fuchs, S.; Rexroth, A.; Beck, T.; Mosandl, A. Fragmentation Mechanism of Rose Oxide in Electron Impact Mass Spectrometry. Eur. Mass Spectrom. 1998c, 4, 163-166.