The Importance of Sulfur-Containing Compounds to Fruit Flavors

  • Karl-Heinz Engel

Abstract

Sulfur-containing volatiles are of outstanding importance in flavor chemistry (Boelens and van Gemert, 1993; Mussinan and Keelan, 1994). Thermally generated aromas are dominated by a broad spectrum of sulfur compounds ranging from aliphatic thioles (Werkhoff et al., 1996) to heterocycles (Güntert et al., 1990). Sulfur-containing volatiles are not only formed in the course of thermal processing of foods but they also constitute essential components of the biogenetically derived aroma patterns of biological systems such as fruits. Pineapple (Takeoka et al., 1991; Umano et al., 1992), grapefruit (Demole et al., 1982), black currant (Riguad et al., 1986) and durian (Wong and Tie, 1993; Fischer et al.,1995) are representatives of fruits exhibiting sensory properties which are strongly influenced by sulfur compounds.

Keywords

Fermentation Carotenoid Lactone Cyclodextrin Lyase 

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References

  1. Boelens, M. H.; van Gemert, L. J. Volatile character-impact sulfur compounds and their sensory properties. Perfum. Flavor. 18, 29–39 (1993)Google Scholar
  2. Demole, E.; Enggist, P.; Ohloff, G. 1-p-Menthene-8-thiol: a powerful impact constituent of grapefruit juice (Citrus paradisi Macfayden). HeIv. Chim. Acta 65, 1785–1794 (1982)CrossRefGoogle Scholar
  3. Engel, K.-H.; Heidlas, J.; Albrecht, W; Tressl, R. Biosynthesis of chiral flavor and aroma compounds in plants and microorganisms. In: Teranishi, R.; Buttery, R. G.; Shahidi, E (Eds.) Flavor Chemistry. Trends and Developments. American Chemical Society Symposium Series 388, Washington, D. C., 1989, p. 8–22CrossRefGoogle Scholar
  4. Engel, K.-H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passii lora edulis f. flavicarpa). J. Agric. Food Chem. 39, 2249–2252 (1991)CrossRefGoogle Scholar
  5. Fischer, N.; Hammerschmidt, F.-J.; Brunke, E.-J. Analytical investigation of the flavor of Cupuaçu (Theobroma grad florum Spreng.). In: Fruit Flavors. Biogenesis, Characterization, and Authentication. Russeff, R., Leahy, M. M. (Eds.); American Chemical Society: Washington, D.C., 1995, pp 8–20CrossRefGoogle Scholar
  6. Friedman, L.; Miller, J. G. Odor incongruity and chirality. Science 172, 1044 (1972)CrossRefGoogle Scholar
  7. Güntert, M.; Brüning, J.; Emberger, R.; Köpsel, M.; Kuhn, W; Thielmann, T.; Werkhoff, P. Identification and formation of some selected sulfur-containing flavor compounds in various meat model systems. J. Agric. Food Chem. 38, 2027–2041 (1990)CrossRefGoogle Scholar
  8. Heusinger, G.; Mosandl, A. Chirale, schwefelhaltige Aromastoffe der gelben Passionsfrucht (Pass flora edulis f. flavicarpa). Darstellung der Enantiomeren and absolute Konfiguration. Tetrahedron Lett. 25, 507–510 (1984)CrossRefGoogle Scholar
  9. Küntzel, H.; Frater, G. Enantioselective synthesis of (+)- and (–)-cis-and trans-2-methyl-4-propyl-1,3oxathianes. Sulfur Letters 10, 181–186 (1989)Google Scholar
  10. Leitereg, T. J.; Guadagni, D. G.; Harris, J.; Mon, T. R.; Teranishi, R. Chemical and sensory data supporting the difference between the odors of the enantiomeric carvones. J. Agric. Food Chem. 19, 785 (1971)CrossRefGoogle Scholar
  11. Maga, J. A. Lactones in Foods. CRC Crit. Rev. Food Sci. Nutr. 1–56 (1976)Google Scholar
  12. Mosandl, A. Enantioselective capillary gas chromatography and stable isotope ratio mass spectrometry in the authenticity control of flavors and essential oils. Food Rev. Int. 11, 597–664 (1995)CrossRefGoogle Scholar
  13. Mosandl, A.; Heusinger, G. 1,3-Oxathianes, chiral fruit flavor compounds. Liebigs Ann. Chem. 1185–1191 (1985)Google Scholar
  14. Mosandl, A.; Heusinger, G.; Wistuba, D.; Schurig, V. Analysis of a chiral aroma compound by complexation gas chromatography. Z Lebensm. Unters. Forsch. 179, 385–386 (1984)CrossRefGoogle Scholar
  15. Murray, K. E.; Shipton, J.; Whitfield, F. B. The chemistry of food flavor. I. Volatile constituents of passion fruit, Passii lora edulis. Aust. J. Chem. 25, 1921–1933 (1972)CrossRefGoogle Scholar
  16. Mussinan, C. J., Keelan, M. E. (Eds.) Sulfur Compounds in Foods. ACS Symposium Series 564; American Chemical Society, Washington, D.C., 1994CrossRefGoogle Scholar
  17. Ohlofï, G. Riechstoffe and Geruchssinn. Die molekulare Welt der Düfte. Springer Verlag, Berlin, 1990Google Scholar
  18. Pickenhagen, W. Enantioselectivity in odor perception. In: Teranishi, R.; Buttery, R. G.; Shahidi, F. (Eds.) Flavor Chemistry. Trends and Developments. American Chemical Society Symposium Series 388, Washington, D.C., 1989, p. 151–157CrossRefGoogle Scholar
  19. Pickenhagen, W; Brönner-Schindler, H. Enantioselective synthesis of (+)- and (–)-cis-2-methyl-4-propyl-1,3oxathiane and their olfactive properties. Helv. Chim. Acta 67, 947–952 (1984)CrossRefGoogle Scholar
  20. Rigaud, J.; Etievant, P.; Henry, R.; Latrasse, A. 4-Methoxy-2-methyl-2-mercaptobutane, a major constituent of the aroma of the black currant bud (Ribes nigrum L.). Sci. Aliments 6, 213–220 (1986)Google Scholar
  21. Roling, I.; Schmarr, H.-G.; Eisenreich, W; Engel, K.-H. Analytical and sensory characterization of γ-and δ-thiolactones. J. Agric. Food Chem. 46, 668–672 (1998)CrossRefGoogle Scholar
  22. Schieberle, P. Primary odorants in popcorn. J. Agric. Food Chem. 39, 1141–1144 (1991)CrossRefGoogle Scholar
  23. Schmarr, H.-G. Ph. D. Thesis, University Frankfurt/Main, Germany (1992)Google Scholar
  24. Schmarr, H.-G.; Schellenberg, A.; Engel, K.-H., manuscript in preparationGoogle Scholar
  25. Shibamoto, T.; Tang, C. S. Minor tropical fruits—mango, papaya, passion fruit and guava. In: Morton, I. D., MacLeod, A. J. (Eds.) Food Flavors. Part C. The Flavor of Fruits. Elsevier, Amsterdam, 1990, p. 221–280Google Scholar
  26. Singer, G., Heusinger, G., Fröhlich, O., Schreier, P.; Mosandl, A. Chirality evaluation of 2-methyl-4-propyl-1,3oxathiane from the yellow passion fruit. J. Agric. Food Chem. 34, 1029–1033 (1986)CrossRefGoogle Scholar
  27. Takeoka, G. R.; Buttery, R. G.; Teranishi, R.; Flath, R. A.; Güntert, M. Identification of additional pineapple volatiles. J. Agric. Food Chem. 39, 1848–1851 (1991)CrossRefGoogle Scholar
  28. Tominaga, T.; Darriet, P.; Dubourdieu, D. Identification de l’acétate de 3-mercaptohexanol, composé à forte odeur de buis, intervenant dans l’arôme des vins de Sauvignon. Vitis 35, 207–210 (1996)Google Scholar
  29. Tominaga, T.; Murat, M.-L.; Dubourdieu, D. Development of a method for analyzing the volatile thiols involved in the characteristic aroma of wines made from Vitis vinifera L. cv. Sauvignon blanc. J. Agric. Food Chem. 46, 1044–1048 (1998a)CrossRefGoogle Scholar
  30. Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon blanc wines. Flavor Fragr. J. 13, 159–162 (1998b)CrossRefGoogle Scholar
  31. Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. New type of flavor precursors in Vitis vinifera L. cv. Sauvignon blanc: S-cysteine conjugates. J. Agric. Food Chem. 46, 5215–5219 (1998c)CrossRefGoogle Scholar
  32. Tressl, R.; Engel, K.-H. Formation and analysis of optically active aroma compounds. In: Schreier, P. (Ed.) Analysis of Volatiles. Walter de Gruyter, Berlin, New York, 1984, p. 323–342Google Scholar
  33. Tressl, R.; Engel, K.-H. Biogenesis of chiral aroma components and their analytical characterization at trace level. In: Adda, J. (Ed.) Progress in Flavor Research 1984. Elsevier Science Publishers B.V., Amsterdam, 1985, p. 441–455Google Scholar
  34. Tressl, R.; Engel, K.-H.; Albrecht, W. Detection of Adulteration by Investigation of Aroma and Flavor Components. In: Nagy, S.; Attaway, J. A.; Rhodes, M. E. (Eds.) Adulteration of Fruit Juice Beverages. Marcel Dekker, Inc., New York, Basel, 1988, pp. 67–80Google Scholar
  35. Umano, K.; Hagi, Y.; Nakahara, K.; Shoji, A.; Shibamoto, T. Volatile constituents of green and ripened pineapple (Ananas comosus [L.] Merr.). J. Agric. Food Chem. 40, 599–603 (1992)CrossRefGoogle Scholar
  36. Weber, B.; Haag, H.-P; Mosandl, A. LIX. 3-Mercaptohexyl-und 3-Methylthiohexylalkanoate—Struktur und Eigenschaften der Enantiomere. Z. Lebensm. Unters. Forsch. 195, 426–428 (1992)CrossRefGoogle Scholar
  37. Weber, B.; Dietrich, A.; Maas, B.; Marx, A.; Olk, J.; Mosandl, A. LXVI. Enantiomeric distribution of the chiral sulphur-containing alcohols in yellow and purple passion fruits. Z. Lebensm. Unters. Forsch. 199, 48–50 (1994)CrossRefGoogle Scholar
  38. Weber, B.; Maas, B.; Mosandl, A. Stereoisomeric Flavor Compounds. 72. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits. J. Agric. Food Chem. 43, 2438–2441 (1995)CrossRefGoogle Scholar
  39. Werkhoff, P.; Güntert, M.; Krammer, G.; Sommer, H.; Kaulen, J. Vacuum headspace method in aroma research: flavor chemistry of yellow passion fruits. J. Agric. Food Chem. 46, 1076–1093 (1998)CrossRefGoogle Scholar
  40. Werkhoff, P.; Brüning, J.; Güntert, M.; Kaulen, J.; Krammer, G.; Sommer, H. Potent mercapto/methylthio-substituted aldehydes and ketones in cooked beef liver. Adv. Food Sci. 18, 19–27 (1996)Google Scholar
  41. Whitfield, F. B.; Last, J. H. The flavor of the passion fruit—a review. In: Brunke, E. J. (Ed.) Progress in Essen-tial Oil Research. De Gruyter, Berlin, 1986, p. 3–48Google Scholar
  42. Winter, M.; Klöti, R. Über das Aroma der gelben Passionsfrucht (Passiflora edulis f. flavicarpa). HeIv. Chim. Acta 55, 1916–1921 (1972)CrossRefGoogle Scholar
  43. Winter, M.; Furrer, A.; Willhalm, B.; Thommen, W. Identification and synthesis of two new organic sulfur compounds from the yellow passion fruit (Passiflora edulis f. flavicarpa). HeIv. Chim. Acta 59, 1613–1620 (1976)CrossRefGoogle Scholar
  44. Winter, M.; Willhalm, B. Ger. Offen 2,338,680 (1972)Google Scholar
  45. Winter, M. Ger. Offen. 2,534,162 (1976)Google Scholar
  46. Wong, K. C.; Tie, D. Y. Volatile constituents of durian (Dario zibethinus Murr.). Flavor Fragr. J. 10, 79–83 (1995)CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1999

Authors and Affiliations

  • Karl-Heinz Engel
    • 1
  1. 1.Lehrstuhl für Allgemeine LebensmitteltechnologieTechnische Universität MünchenFreising-WeihenstephanGermany

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