Advertisement

Recent Advances in High-Performance Liquid Chromatography of Volatile Natural Products

  • Denis Barron
  • Anni Pabst
Part of the Recent Advances in Phytochemistry book series (RAPT, volume 25)

Abstract

Gas chromatography (GC) is considered to be the method of choice in the analysis of volatile compounds, because of its high resolving power and the availability of universal detection using flame ionization (FID) detectors. However, GC is mainly an analytical method and its application is limited when preparative isolation of volatile compounds is required. On the other hand, GC analysis of thermolabile and/or polar compounds is often difficult to achieve. Although these problems could be easily solved by the use of liquid chromatography, the latter technique has received limited application in the analysis of volatile constituents because of its poor resolution and the lack of a sensitive universal detector. In the past, the application of liquid chromatography in the analysis of volatiles has been mostly restricted to the prefractionation of crude extracts for GC analysis.

Keywords

Normal Phase Preparative Isolation Diol Column Aroma Constituent Raspberry Fruit 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    SCHMIT, J.A., WILLIAMS, R.C., HENRY, R.A. 1973. Applications of combined gel permeation chromatography and high speed liquid chromatography for the separation of complex flavor mixtures. J. Agric. Food Chem. 21: 551–556.CrossRefGoogle Scholar
  2. 2.
    RABEL, F. 1974. Increment gradient elution in liquid chromatography. Amer. Lab. 6: 33–34.Google Scholar
  3. 3.
    LARMANN, J.P., WILLIAMS, R.C., BAKER, D.R. 1975. Methods development for high-speed preparative liquid chromatography. Chromatographia 8: 92–96.CrossRefGoogle Scholar
  4. 4.
    KOMAE, H., HAYASHI, N. 1975. Separation of essential oils by liquid chromatography. J. Chromatogr. 114:258–260.CrossRefGoogle Scholar
  5. 5.
    ROSS, M.S.F. 1976. Analysis of cinnamon oils by high-pressure liquid chromatography. J. Chromatogr. 118: 273–275.CrossRefGoogle Scholar
  6. 6.
    WILLIAMS, A.T.R., SLAVIN, W. 1977. Determination of methyl anthranilate in grape beverages by high-pressure liquid chromatography and fluorescence. J. Agric. Food Chem. 25: 756–759.CrossRefGoogle Scholar
  7. 7.
    TEITELBAUM, C.L. 1977. A new strategy for the analysis of complex flavors. J. Agric. Food Chem. 25: 466–470.CrossRefGoogle Scholar
  8. 8.
    PETTEI, M.J., PILKIEWICZ, F.G., NAKANISHI, K. 1977. Preparative liquid chromatography applied to difficult separations. Tetrahedron Letters 24: 2083–2086.CrossRefGoogle Scholar
  9. 9.
    ROSS, M.S.F. 1978. Application of high-performance liquid chromatography to the analysis of volatile oils. J. Chromatogr. 160: 199–204.CrossRefGoogle Scholar
  10. 10.
    WULF, L.W., NAGEL, C.W., BRANEN, A.L. 1978. High-pressure liquid chromatographic separation of the naturally occurring toxicants myristicin, related aromatic ethers and falcarinol. J. Chromatogr. 161: 271–278.PubMedCrossRefGoogle Scholar
  11. 11.
    SHIBATA, 1978. On the constituents of an essential oil of Kudzu. Agric. Biol. Chem. 42: 195–197.CrossRefGoogle Scholar
  12. 12.
    JONES, B.B., CLARK, B.C., IACOBUCCI, G.A. 1979. Semi- preparative high-performance liquid chromatographic separation of a characterized flavor mixture of monoterpenes. J. Chromatogr. 178: 575–578.CrossRefGoogle Scholar
  13. 13.
    MCCLOUD, T.G., HEINSTEIN, P. 1979. Analysis of biosynthesized terpene alcohols facilitated by C18 phase-bonded silica. J. Chromatogr. 174: 461–464.CrossRefGoogle Scholar
  14. 14.
    BERGMAN, N.A., HALL, B. 1979. Small-scale preparative separation of (-)-menthone and (+)-isomenthone by high performance liquid chromatography. Acta Chem. Scand. B33: 148–156.CrossRefGoogle Scholar
  15. 15.
    SCOTT, R.P.W., KUCERA, P. 1979. Mode of operation and performance characteristics of microbore columns for use in liquid chromatography. J. Chromatogr. 169: 51–72.CrossRefGoogle Scholar
  16. 16.
    JONES, B.B., CLARK, B.C., IACOBUCCI, G.A. 1980. Semipreparative high-performance liquid chromatographic separation of singlet oxygen derived limonene hydroperoxides. J. Chromatogr. 202: 127–130.CrossRefGoogle Scholar
  17. 17.
    WARTHEN, J.D. Jr 1980. Preparative high-performance liquid chromatographic separation of natural farnesol isomers. J. Liq. Chromatogr. 3: 279–286.CrossRefGoogle Scholar
  18. 18.
    HARA, S., OHSAWA, A., ENDO, J., SASHIDA, Y., ITOKAWA, H. 1980. Liquid chromatographic resolution of the unsaturated sesquiterpene alcohol isomers using silica gel-binary solvent systems. Anal. Chem. 52: 428–430.CrossRefGoogle Scholar
  19. 19.
    MICALI, G., CURRO, P., CALABRO, G. 1980. Reversed-phase high-performance liquid chromatography for the determination of β-asarone. J. Chromatogr. 194: 245–250.CrossRefGoogle Scholar
  20. 20.
    VAN DEN BROUCKE, C.O., LEMLI, J.A. 1980. Chemical investigation of the essential oil of Origanum compactum. Planta Medica 38: 265–266.Google Scholar
  21. 21.
    STRACK, D., PROKSCH, P., GÜLZ, P.G. 1980. Reversed phase high performance liquid chromatography of essential oils. Z. Naturforsch. 35c: 675–681.Google Scholar
  22. 22.
    SOLINAS, V., GESSA, C., FALCHI DELITALA, L. 1981. High-performance liquid chromatographic analysis of carvacrol and thymol in the essential oil of Thymus capitatus. J. Chromatogr. 219: 332–337.CrossRefGoogle Scholar
  23. 23.
    HAUT, S.A., CORE, M.T. 1981. Separation of menthol isomers by normal phase high performance liquid chromatography. J. Liq. Chromatogr. 4: 1869–1874.CrossRefGoogle Scholar
  24. 24.
    SATO, H., KAGEYU, A., MIYASHITA, K., TANAKA, Y. 1982. Separation of farnesol isomers by liquid chromatography. J. Chromatogr. 237: 178–182.CrossRefGoogle Scholar
  25. 25.
    LINOSSIER, J.L., PEYRON, L., ROCCA, J.L. 1982. Chromatographie en phase liquide des concrètes de Jasmin. Analyse des éluats par spectrophotométrie UV-visible à détection parallèle. Analusis 10: 310–318.Google Scholar
  26. 26.
    NEWBERRY, J.E., LOPEZ DE HADDAD, M.P., CHARLWOOD, K.A. 1983. High-performance liquid chromatography of terpenoid alcohols in essential oils. Anal. Chim. Acta 147: 387–391.CrossRefGoogle Scholar
  27. 27.
    NEWBERRY, J.E., LOPEZ DE HADDAD, M.P. 1983. Terpenoid analysis II. The separation of some monoterpene alcohols by high-performance liquid chromatography with electrochemical detection. J. Chromatogr. 260: 173–176.CrossRefGoogle Scholar
  28. 28.
    TSUNEKA, T., ISHIHARA, M., SHIOTA, H., SHIGA, M. 1983. Volatile components of quince fruit (Cydonia oblonga Mill.). Agric. Biol. Chem. 47: 2495–2502.CrossRefGoogle Scholar
  29. 29.
    WISNEKI, H.H., YATES, R.L., DAVIS, H.M. 1983. High-performance liquid chromatographic-fluorometric determination of safrole in perfume, cologne and toilet water. J. Chromatogr. 255: 455–461.CrossRefGoogle Scholar
  30. 30.
    BICCHI, C., SANDRA, P., SCHELFAUT, M., VERZELE, M. 1983. Studies on the essential oil of Valeriana celtica L. J. High Resol. Chromatogr. Chromatogr. Commun. 6: 213–215.CrossRefGoogle Scholar
  31. 31.
    TOULEMONDE, B., BEAUVERD, D. 1984. Contribution à l’étude d’une camomille sauvage du Maroc: L’huile essentielle d’Ormenis mixta. Parfums, Cosmét. Arômes 60: 65–67.Google Scholar
  32. 32.
    SMITH, R.M., BECK, S. 1984. High-performance liquid chromatographic analysis of eugenol in pimento using ultraviolet and electrochemical detection. J. Chromatogr. 291: 424–427.CrossRefGoogle Scholar
  33. 33.
    PARKIN, J.E. 1984. High-performance liquid chromatographic assay of menthol using indirect photometric detection. J. Chromatogr. 303: 436–439.CrossRefGoogle Scholar
  34. 34.
    HAJJI, S., BELIVEAU, J., SIMON, D.Z., SALVADOR, R., AUBE, C., CONTI, A. 1984. A rapid method for the prefractionation of essential oils. Application to the essential oil of black spruce (Picea mariana, Mill. BSP.). J. Liq. Chromatogr. 7: 2671–2677.CrossRefGoogle Scholar
  35. 35.
    GALLI, C.L., GALLI, G., TRAGNI, E., CARUSO, D., FIECCHI, A. 1984. Quantitative analysis of α,β-thujone, pulegone, safrole, coumarin and β-asarone in alcoholic beverages by selected ion monitoring. J.Appl. Toxicol. 4: 273–276.PubMedCrossRefGoogle Scholar
  36. 36.
    CHAMBLEE, T.S., CLARK, B.C., RADFORD, T., IACOBUCCI, G.A. 1985. General method for the high-performance liquid chromatographic prefractionation of essential oils and flavor mixtures for gas chromatographic-mass spectrometric analysis. Identification of new constituents of lime oil. J. Chromatogr. 330: 141–151.CrossRefGoogle Scholar
  37. 37.
    MORIN, P., CAUDE, M., RICHARD, H., ROSSET, R. 1986. Semipreparative separation of terpenoids from essential oils by high-performance liquid chromatography and their subsequent identification by gas chromatography-mass spectrometry. J. Chromatogr. 363: 57–69.CrossRefGoogle Scholar
  38. 38.
    YAMASAKI, T., SAKAI, M., KANAMORI, T., SOGO, M. 1986. Low temperature liquid chromatographic separation of oxygenated terpenes from terpene hydrocarbons. Chromatographia 21: 478–479.CrossRefGoogle Scholar
  39. 39.
    BEYER, J., BECKER, H., MARINI, R. 1986. Separation of labile terpenoids by low temperature HPLC. J. Liq. Chromatogr. 9: 2433–2441.CrossRefGoogle Scholar
  40. 40.
    KAOUADJI, M., POUGET, C. 1986. Additional phthalide derivatives from Meum athamanticum. J. Nat. Prod. 49: 184–185.CrossRefGoogle Scholar
  41. 41.
    KAOUADJI, M., DE PACHTERE, F., POUGET, C., CHULIA, A.J., LAVAITTE, S. 1986. Three additional phthalide derivatives, an epoximonomer and two dimers, from Ligusticm wallichii rhizomes. J. Nat. Prod. 49: 872–877.CrossRefGoogle Scholar
  42. 42.
    FRIEDEL, H.D., MATUSCHI, R. 1987. Separation of non-polar sesquiterpene olefins from tolu balsam by high-performance liquid chromatography; silver Perchlorate impregnation of a prepacked preparative silica gel column. J. Chromatogr. 407: 343–348.CrossRefGoogle Scholar
  43. 43.
    CURRO, P., MICALI, G., LANUZZA, F. 1987. Determination of β-asarone, safrole, isosafrole and anethole in alcoholic drinks by high-performance liquid chromatography. J. Chromatogr. 404: 273–278.PubMedCrossRefGoogle Scholar
  44. 44.
    LEE, H.S., NAGY, S. 1987. HPLC of 2,5-dimethyl-4-hydroxy-3(2H)-furanone in pineapple and grapefruit juices. J. Food Sci. 52: 163–165.CrossRefGoogle Scholar
  45. 45.
    PIRKLE, W.H., Sowin, T.J. 1987. Synthesis and separation of dia-stereomeric imino alcohol derivatives of chiral phthalides: A method for assignment of phthalide absolute configurations. J. Org. Chem. 52:3011–3017.CrossRefGoogle Scholar
  46. 46.
    UHLIG, J.W., CHANG, A., JEN, J.J. 1987. Effects of phtalides on celery flavor. J. Food Sci 52: 658–660.CrossRefGoogle Scholar
  47. 47.
    CLARK, B.C., CHAMBLEE, T.S., IACOBUCCI, G.A. 1987. HPLC isolation of the sesquiterpene hydrocarbon germacrene B from lime peel oil and its characterization as an important flavor impact constituent. J. Agric. Food Chem. 35: 514–518.CrossRefGoogle Scholar
  48. 48.
    BITTEUR, S., ROSSET, R. 1987. Comparison of octadecyl-bonded silica and styrene-divinylbenzene copolymer sorbents for trace enrichment purposes. Fundamental aspects I. Calibration of the stationary phases in pure water. J. Chromatogr. 394: 279–293.CrossRefGoogle Scholar
  49. 49.
    BITTEUR, S., ROSSET, R. 1987. Comparison of octadecyl-bonded silica and styrene-divinylbenzene copolymer sorbents for trace enrichment purposes. Fundamental aspects II. Linear chromatographic behaviour of the extracting supports. Chromatographia 23: 163–168.CrossRefGoogle Scholar
  50. 50.
    BITTEUR, S., ROSSET, R. 1988. Use of an octadecyl-bonded silica and a styrene-divinylbenzene copolymer for the recovery of blackcurrant aroma compounds from a food plant waste water. J. Food Sci. 53: 141–147.CrossRefGoogle Scholar
  51. 51.
    ARCHER, A.W. 1988. Determination of safrole and myristicin in nutmeg and mace by high-performance liquid chromatography. J. Chromatogr. 438: 117–121.PubMedCrossRefGoogle Scholar
  52. 52.
    MCELDOWNEY, A.M., MENARY, R.C. 1988. Analysis of Pyrethrins in Pyrethrum extracts by high-performance liquid chromatography. J. Chromatogr. 447: 239–243.Google Scholar
  53. 53.
    KOIZUMI, H., SUZUKI, Y. 1988. High-performance liquid chroma tography of aliphatic aldehydes by means of post-column extraction with fluorometric detection. J. Chromatogr. 457: 299–307.CrossRefGoogle Scholar
  54. 54.
    TAKEUCHI, T., ISHII, D., NAKANISHI, A. 1988. Analysis of aldehydes by micro high-performance liquid chromatography with post-column derivatization on enzyme-immobilized glass beads. Chromatographia 25: 507–510.CrossRefGoogle Scholar
  55. 55.
    PEKIC, B., SLAVICA, B., LEPOJEVIC, Z. 1988. Determination and preparative isolation of chamazulene from essential oil of chamomile. Arh. Farm. 38: 177–182. (CA 110:2191669)Google Scholar
  56. 56.
    HOWELLS, J.S., JOHNSTON, D., 1988. An HPLC method employing diode-array detection for the identification of natural plant extracts tolu syrup and wild cherry syrup in a herbal cough remedy. Anal. Proc. (London) 25: 163–164.Google Scholar
  57. 57.
    YU, T.H., WU, G.M. 1989. Effects of pH on the formation of flavour compounds of disrupted garlic. J. Chromatogr. 462: 137–145.CrossRefGoogle Scholar
  58. 58.
    MOSANDL, A., HOLLNAGEL, A. 1989. Stereoisomeric flavour compounds XXXV: Chiral aroma compounds of sherry I. Optically pure stereoisomers of solerone and solerole. Chirality 1: 293–300.CrossRefGoogle Scholar
  59. 59.
    HÜNIG, S., KLAUNZER, N. 1989. Enantiomer separation of α-substituted γ-butyrolactones on the chiral Polyacrylamide resin ChiraSpher®. J. Chromatogr. 481: 387–390.CrossRefGoogle Scholar
  60. 60.
    ARCHER, A.W. 1989. Analysis of vanilla essences by high-performance liquid chromatography. J. Chromatogr. 462: 461–466.CrossRefGoogle Scholar
  61. 61.
    VAN BEEK, T.A., KLEIS, R., LELYVELD, G.P., DE GROOT, A. 1989. Preparative isolation of (+)-beta-eudesmol from Amyris balsamifera. Chromatographia 28: 126–128.CrossRefGoogle Scholar
  62. 62.
    LIU, S.H., NORRIS, D.M., LYNE, P. 1989. Volatiles from the foliage of soybeans, Glycine max, and lima beans, Phaseolus lunatus: Their behavioral effects on the insects Trichoplusia ni and Epilachna varivestis. J. Agric. Food Chem. 37: 496–501.CrossRefGoogle Scholar
  63. 63.
    SCHULZ, H., ALBROSCHEIT, G. 1989. Characterization of oakmoss products used in perfumery by high-performance liquid chromatography. J. Chromatogr. 466: 301–306.CrossRefGoogle Scholar
  64. 64.
    EBEL, S., FISCHER, A. 1989. HPLC determination of menthyl acetate in several peppermint oils by Polarimetric detection. Arch. Pharm. 322: 83–88.CrossRefGoogle Scholar
  65. 65.
    JARES, E.A., POMILIO, A.B. 1989. Isolation of sesquiterpenes from Senecio crassiflorus by combined dry column and high performance liquid chromatography. J. High Resolut Chromatogr. 12: 565–568.CrossRefGoogle Scholar
  66. 66.
    WERKHOFF, P., BRETSCHNEIDER, W., HERRMANN, H.J., SCHREIBER, K. 1989. Odor analysis. Part 8. Preparative gas chromatography and HPLC techniques. Labor-Praxis 13: 1121–1125.Google Scholar
  67. 67.
    IBERL, B., WINKLER, G., MÜLLER, B., KNOBLOCH, K. 1990. Quantitative determination of allicin and alliin from garlic by HPLC. Planta Medica 56: 320–326.PubMedCrossRefGoogle Scholar
  68. 68.
    IBERL, B., WINKLER, G., KNOBLOCH, K. 1990. Products of allicin transformation: ajoenes and dithiins, characterization and their determination by HPLC. Planta Medica 56: 202–211.PubMedCrossRefGoogle Scholar
  69. 69.
    SCHMARR, H.G., MOSANDL, A., GROB, K. 1990. Stereoisomeric flavour compounds XXXVIII: Direct chirospecific analysis of γ-lactones using on-line coupled LC-GC with a chiral separation column. Chromatographia 29: 125–130.CrossRefGoogle Scholar
  70. 70.
    MUNARI, F., DUGO, G., COTRONEO, A. 1990. Automated on-line HPLC-HRGC with gradient elution and multiple GC transfer applied to the characterization of citrus essential oils. J. High Resolut. Chromatogr. 13: 56–61.CrossRefGoogle Scholar
  71. 71.
    KATAMAYA, M., MUKAI, Y., TANIGUCHI, H. 1990. High performance liquid chromatographic determination of cinnamaldehyde. Analyst 115: 9–11.CrossRefGoogle Scholar
  72. 72.
    MORIN, P., CAUDE, M., RICHARD, H., ROSSET, R. 1985. Séparation des terpénoïdes par Chromatographie en phase liquide. Analusis 13: 196–217.Google Scholar
  73. 73.
    KUBECZKA, K.H. 1984. Progress in isolation techniques for essential oil constituents. Essent. Oils Aromat. Plants, Proc. Int. Symp. 15th, (A. Baerheim-Svendsen, U.C. Scheffer, eds.) Nijhoff/Jung, Dordrecht, pp. 107–126.Google Scholar
  74. 74.
    KUBECZKA, K.H. 1984. Progress in isolation techniques for essential oil constituents. Adv. Med. Plant Res., Plenary Lect. Int. Congr., 32nd, (A.J. Vlietick, R.A. Domisse, eds.) Wiss. Verlagsges, Stuttgart, pp. 197–224.Google Scholar
  75. 75.
    KUBECZKA, K.H. 1981. Application of HPLC for the separation of flavour compounds. Flavour’81: 3rd Weurmann Symposium, (P. Schreier, ed.), W. de Gruyter, Berlin-New York, pp. 345–359.Google Scholar
  76. 76.
    BITTEUR, S. 1984. Rôle de la Chromatographie en phase liquide dans la recherche sur les arômes. Analusis 12: 51–62.Google Scholar
  77. 77.
    ROUSSEFF, R.L. 1985. The use of high-performance liquid chromatography in flavor studies. ACS Symp. Ser. 289: 79–94.CrossRefGoogle Scholar
  78. 78.
    SANDRA, P., BICCHI, C., BELLIARDO, F. 1985. Possibilities and limitations of off-line HPLC-CGC and on-line selective sampling in flavour research. Top. Flavour Res., Proc. Int. Conf., (R.Q. Berger, S. Nitz, P. Schreier, eds.), H. Eichhorn, Marzling-Hangenham, pp. 27–42.Google Scholar
  79. 79.
    WILLIAMS, P.J., STRAUSS, C.R., WILSON, B., MASSY-WESTROPP, R.A. 1982. Use of C18 reversed-phase liquid chromatography for the isolation of monoterpene glycosides and nor-iso-prenoid precursors from grape juice and wines. J. Chromatogr. 235: 471–480.CrossRefGoogle Scholar
  80. 80.
    BITTEUR, S., GÜNATA, Z., BRILLOUET, J.M., BAYONOVE, C., CORDONNIER, R. 1989. GC and HPLC of grape monoterpenyl glycosides. J. Sci. Food Agric. 47: 341–352.CrossRefGoogle Scholar
  81. 81.
    GALLOIS, A. 1987. Collection of gas chromatographic fractions for NMR analysis. HRC & CC 10: 213–214.CrossRefGoogle Scholar
  82. 82.
    MURRAY, K.E., STANLEY, G. 1968. Class separation of flavour volatiles by liquid chromatography on silica gel at 1o. J. Chromatogr. 34: 174–179.PubMedCrossRefGoogle Scholar
  83. 83.
    PALMER, J.K. 1973. Separation of components of aroma concentrates on the basis of functional group and aroma quality. J. Agric. Food Chem. 21:923–925.CrossRefGoogle Scholar
  84. 84.
    BARRON, D., ETIEVANT, P. 1990. The volatile constituents of strawberry jam. Z. Lebensm. Unters. Forsch. 191: 279–285.CrossRefGoogle Scholar
  85. 85.
    BARRON, D. 1991. The use of HPLC using diol-bonded silica in the prefractionation of aroma extracts. J. Chromatogr. in press.Google Scholar
  86. 86.
    PABST, A., BARRON, D., ETIEVANT, P., SCHREIER, P. 1991. Studies on the enzymatic hydrolysis of bound aroma constituents from raspberry fruit pulp. J. Agric. Food Chem. in press.Google Scholar
  87. 87.
    PABST, A., BARRON, D., ADDA, J., SCHREIER, P. 1990. Phenyl-butan-2-one β-D-glucosides from raspberry fruit. Phytochemistry 29: 3853–3858.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1991

Authors and Affiliations

  • Denis Barron
    • 1
  • Anni Pabst
    • 2
  1. 1.Pharmacognosy Laboratory, School of PharmacyJoseph Fourier University-GrenobleLa Tronche CédexFrance
  2. 2.Lehrstuhl für LebensmittelchemieUniversität WürzburgWürzburgGermany

Personalised recommendations