Summary
The configurations of free amino acids (AAs) in orange juice beverages (commercial products of satisfactory and unsatisfactory quality), an orange juice concentrate (bulk product suspected of being adulterated), and in an orange juice that has been contaminated by addition ofLactobacillus plantarum as a model for microbial spoilage, were determined, after derivatization, by means of gas-liquid chromatography (GC) using fused-silica capillary columns coated with Chirasil-L-Val or Chirasil-D-Val as stationary phases. AAs were isolated from juices by treatment with Dowex WX8 ion-exchanger and were investigated, by GC, as theirN(O)-pentafluoropropionylorN(O)-trifluoroacetyl 1-propyl esters. It was found that the high quality orange juice beverage contained L-AAs exclusively whereas this juice, after fermentation withLactobacillus, contained free D-Ala (32.7%), D-Val (62.3%), D-Phe (20.0%), D-Glu (24.3%), D-Ser (2.6%), D-Asp (0.8%), and significant amounts of D-Pro [% D=100 D/(D+L)]. D-Ala (8.8%) and D-Ser (4.2%) were found in a sensory and analytically unsatisfactory orange juice beverage, whilst D-Ala (27.5%) and D-Ser (14.3%) were detected in the orange juice concentrate suspected of being adulterated.
Although capillary GC on chiral stationary phases is regarded as being highly suitable for the determination of AA enantiomers in fruit juice beverages, detection of D-AAs is currently not considered as conclusive proof of fruit juice adulteration caused by addition of AA racemates since a non-microbial origin of D-AAs in the respective juice, or an original occurrence of D-AAs, in either the free, substituted, or peptide-bonded form in the fruits, cannot be excluded with certainty.
Similar content being viewed by others
References
For a comprehensive review see: “Adulteration of Fruit Juice Beverages”,S. Nagy, J. A. Attaway, M. E. Rhodes, eds., Marcel Dekker, New York; 1988.
J. Fry, in: “Production and Packaging of Non-Carbonated Fruit Juices and Fruit Beverages”,D. Hicks, ed., Blackie, Glasgow, and Van Nostrand Reinhold, New York, 1990; pp. 68–113.
W. Ooghe, H. Kasteleyn, I. Temmerman, P. Sandra, J. High Resol. Chromatogr. & Chromatogr. Commun.7, 284 (1984).
D. W. Kuneman, J. K. Braddock, L. L. McChesney, J. Agric. Food Chem.36, 6 (1988).
P. Marfey, Carlsberg Res. Comm.49, 591 (1984).
H. Brückner, C. Keller-Hoehl, Chromatographia30, 621 (1990).
A. Dyremark, M. Ericsson, Chromatographia29, 51 (1990).
H. J. Hofsommer, I. Klein, J. Grüning, H.-R. Höpker, Flüssig. Obst56, 646 (1989).
H. J. Hofsommer, I. Klein, J. Grüning, H.-R. Höpker, in: “UltroChrom '89,4. Würzburger Chromatographie-Gespräche, 4.–6. September 1989”,H.-R. Höpker, ed., Pharmacia-LKB, Freiburg, FRG, 1990; pp. 136–140.
S. Einarsson, B. Josefsson, P. Möller, D. Sanchez, Anal. Chem.59, 1191 (1987).
H. Brückner, M. Hausch, Chromatographia28, 487 (1989).
H. Brückner, M. Hausch, J. High Resol. Chromatogr.12, 680 (1989).
H. Brückner, M. Hausch, Milchwissenschaft45, 421 (1990).
H. Brückner, M. Hausch, in: “Amino Acids: Chemistry, Biology and Medicine”,G. Lubec, R. Rosenthal, eds., Escom, Leiden, 1990; pp. 1172–1182.
H. Frank, G. J. Nicholson, E. Bayer, J. Chromatogr. Sci.15, 174 (1977).
W. A. König, “The Practice of Enantiomer Separation by Capillary Gas Chromatography”, Hüthig, Heidelberg, FRG, 1987; pp. 9–15.
H. Brückner, R. Wittner, H. Godel, J. Chromatogr.476, 73 (1989).
H. Brückner, C. Keller-Hoehl, R. Wittner, H. Godel, in: “Peptides 1990, Proceedings of the 21st European Peptide Symposium”,E. Giralt, D. Andreu, eds., ESCOM, Leiden, The Netherlands, 1991; in press.
E. Bayer, H. Allmendinger, G. Enderle, B. Koppenhoefer, Fresenius' Z. Anal. Chem.321, 321 (1985).
C. E. Vandercook, D. C. Smolensky, J. Assoc. Offic. Anal. Chem.59, 1375 (1976).
A. K. Panezai, in: “Developments in Soft Drinks Technology-1”,L. F. Green, ed., Applied Science Publishers, London, 1978; pp. 209–227.
V. J. Bachelor, in: “Developments in Soft Drinks Technology-3”,H. W. Houghton, ed., Elsevier, London, 1984; pp. 167–210.
M. E. Parish, G. D. Sadler, L. Wicker, J. Food Sci.55, 1023 (1990), and references cited therein.
M. H. Zenk, H. Scherf, Biochim. Biophys. Acta71, 737 (1963).
M. H. Zenk, H. Scherf, Planta62, 350 (1964).
M. Fukuda, A. Tokumura, T. Ogawa, Phytochemistry12, 2593 (1973).
J. L. Frahn, R. J. Illman, Phytochemistry14, 1464 (1975).
T. Robinson, Life Sci.19, 1097 (1976).
T. Ogawa, K. Sasaoka, in: “Abstracts 5th International Congress of Food Science and Technology, Sept. 17–22, 1978, Kyoto (Japan)”, p. 218.
W. A. Aldag, W. L. Young, Agronomy62, 184 (1970).
G. E. Pollock, C.-N. Cheng, S. A. Cronin, Anal. Chem.49, 2 (1977).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Brückner, H., Lüpke, M. Determination of amino acid enantiomers in orange juices by chiral phase capillary gas chromatography. Chromatographia 31, 123–128 (1991). https://doi.org/10.1007/BF02274558
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02274558