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

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Modern Phytochemical Methods

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 25))

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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.

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References

  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.

    Article  CAS  Google Scholar 

  2. RABEL, F. 1974. Increment gradient elution in liquid chromatography. Amer. Lab. 6: 33–34.

    CAS  Google Scholar 

  3. LARMANN, J.P., WILLIAMS, R.C., BAKER, D.R. 1975. Methods development for high-speed preparative liquid chromatography. Chromatographia 8: 92–96.

    Article  CAS  Google Scholar 

  4. KOMAE, H., HAYASHI, N. 1975. Separation of essential oils by liquid chromatography. J. Chromatogr. 114:258–260.

    Article  CAS  Google Scholar 

  5. ROSS, M.S.F. 1976. Analysis of cinnamon oils by high-pressure liquid chromatography. J. Chromatogr. 118: 273–275.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  7. TEITELBAUM, C.L. 1977. A new strategy for the analysis of complex flavors. J. Agric. Food Chem. 25: 466–470.

    Article  CAS  Google Scholar 

  8. PETTEI, M.J., PILKIEWICZ, F.G., NAKANISHI, K. 1977. Preparative liquid chromatography applied to difficult separations. Tetrahedron Letters 24: 2083–2086.

    Article  Google Scholar 

  9. ROSS, M.S.F. 1978. Application of high-performance liquid chromatography to the analysis of volatile oils. J. Chromatogr. 160: 199–204.

    Article  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  11. SHIBATA, 1978. On the constituents of an essential oil of Kudzu. Agric. Biol. Chem. 42: 195–197.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  13. MCCLOUD, T.G., HEINSTEIN, P. 1979. Analysis of biosynthesized terpene alcohols facilitated by C18 phase-bonded silica. J. Chromatogr. 174: 461–464.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  17. WARTHEN, J.D. Jr 1980. Preparative high-performance liquid chromatographic separation of natural farnesol isomers. J. Liq. Chromatogr. 3: 279–286.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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. STRACK, D., PROKSCH, P., GÜLZ, P.G. 1980. Reversed phase high performance liquid chromatography of essential oils. Z. Naturforsch. 35c: 675–681.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  24. SATO, H., KAGEYU, A., MIYASHITA, K., TANAKA, Y. 1982. Separation of farnesol isomers by liquid chromatography. J. Chromatogr. 237: 178–182.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  Google Scholar 

  28. TSUNEKA, T., ISHIHARA, M., SHIOTA, H., SHIGA, M. 1983. Volatile components of quince fruit (Cydonia oblonga Mill.). Agric. Biol. Chem. 47: 2495–2502.

    Article  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  33. PARKIN, J.E. 1984. High-performance liquid chromatographic assay of menthol using indirect photometric detection. J. Chromatogr. 303: 436–439.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  39. BEYER, J., BECKER, H., MARINI, R. 1986. Separation of labile terpenoids by low temperature HPLC. J. Liq. Chromatogr. 9: 2433–2441.

    Article  CAS  Google Scholar 

  40. KAOUADJI, M., POUGET, C. 1986. Additional phthalide derivatives from Meum athamanticum. J. Nat. Prod. 49: 184–185.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  46. UHLIG, J.W., CHANG, A., JEN, J.J. 1987. Effects of phtalides on celery flavor. J. Food Sci 52: 658–660.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  51. ARCHER, A.W. 1988. Determination of safrole and myristicin in nutmeg and mace by high-performance liquid chromatography. J. Chromatogr. 438: 117–121.

    Article  PubMed  CAS  Google Scholar 

  52. MCELDOWNEY, A.M., MENARY, R.C. 1988. Analysis of Pyrethrins in Pyrethrum extracts by high-performance liquid chromatography. J. Chromatogr. 447: 239–243.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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)

    CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  59. HÜNIG, S., KLAUNZER, N. 1989. Enantiomer separation of α-substituted γ-butyrolactones on the chiral Polyacrylamide resin ChiraSpher®. J. Chromatogr. 481: 387–390.

    Article  Google Scholar 

  60. ARCHER, A.W. 1989. Analysis of vanilla essences by high-performance liquid chromatography. J. Chromatogr. 462: 461–466.

    Article  CAS  Google Scholar 

  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.

    Article  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  63. SCHULZ, H., ALBROSCHEIT, G. 1989. Characterization of oakmoss products used in perfumery by high-performance liquid chromatography. J. Chromatogr. 466: 301–306.

    Article  CAS  Google Scholar 

  64. EBEL, S., FISCHER, A. 1989. HPLC determination of menthyl acetate in several peppermint oils by Polarimetric detection. Arch. Pharm. 322: 83–88.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  71. KATAMAYA, M., MUKAI, Y., TANIGUCHI, H. 1990. High performance liquid chromatographic determination of cinnamaldehyde. Analyst 115: 9–11.

    Article  Google Scholar 

  72. MORIN, P., CAUDE, M., RICHARD, H., ROSSET, R. 1985. Séparation des terpénoïdes par Chromatographie en phase liquide. Analusis 13: 196–217.

    CAS  Google Scholar 

  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. 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. 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. BITTEUR, S. 1984. Rôle de la Chromatographie en phase liquide dans la recherche sur les arômes. Analusis 12: 51–62.

    CAS  Google Scholar 

  77. ROUSSEFF, R.L. 1985. The use of high-performance liquid chromatography in flavor studies. ACS Symp. Ser. 289: 79–94.

    Article  Google Scholar 

  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. 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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  81. GALLOIS, A. 1987. Collection of gas chromatographic fractions for NMR analysis. HRC & CC 10: 213–214.

    Article  CAS  Google Scholar 

  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.

    Article  PubMed  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  84. BARRON, D., ETIEVANT, P. 1990. The volatile constituents of strawberry jam. Z. Lebensm. Unters. Forsch. 191: 279–285.

    Article  CAS  Google Scholar 

  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. 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. PABST, A., BARRON, D., ADDA, J., SCHREIER, P. 1990. Phenyl-butan-2-one β-D-glucosides from raspberry fruit. Phytochemistry 29: 3853–3858.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Pharmacognosy Laboratory, School of Pharmacy, Joseph Fourier University-Grenoble, 38706, La Tronche Cédex, France

    Denis Barron

  2. Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 8700, Würzburg, Germany

    Anni Pabst

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  1. Louisiana State University, Baton Rouge, Louisiana, USA

    Nikolaus H. Fischer

  2. University of British Columbia, Vancouver, British Columbia, Canada

    Murray B. Isman

  3. Reed College, Portland, Oregon, USA

    Helen A. Stafford

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Barron, D., Pabst, A. (1991). Recent Advances in High-Performance Liquid Chromatography of Volatile Natural Products. In: Fischer, N.H., Isman, M.B., Stafford, H.A. (eds) Modern Phytochemical Methods. Recent Advances in Phytochemistry, vol 25. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-9060-2_2

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