Abstract
Terpenoids are widely distributed in living systems and they occur predominantly as plant products with an immense number of members. Despite their structural diversity, many of them are chemically and physically closely related to each other. Sophisticated techniques are therefore required to separate mixtures of them and to identify the particular components. Terpenoids are, with only a few exceptions, volatile compounds. Thus gas chromatography is the analytical method of choice and has the great advantage that it can easily be combined with mass spectrometry.
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References
Andersen NH, Falcone MS (1969) The identification of sesquiterpene hydrocarbons from gas-liquid chromatography retention data. J Chromatogr 44:52–59
Benecke R, Thieme H, Nyiredy SZ (1982) Retentionsverhalten der Hauptkomponenten der Lavendel-und Lavandinöle an verschiedenen stationären Phasen in Abhängigkeit von der Säulentemperatur. J Chromatogr 238:75–87
Bicchi C, D’Amato A, Nano GM, Frattini C (1983) Improved method for the analysis of small amounts of essential oils by microdistillation followed by capillary gas chromatography. J Chromatogr 279:409–416
Bicchi C, D’Amato A, Nano GM, Frattini C (1984) Capillary GLC controls of some alpine artemisiae and of the related liqueurs. Chromatographia 18:560–566
Bruins AP (1979) Negative ion chemical ionization mass spectrometry in the determination of components in essential oils. Anal Chem 51:967–972
Bünau v G, Schade G, Golnick K (1969) Massenspektrometrische Untersuchungen von Terpenen. III. Kohlenwasserstoffe der Caran-and der Menthanreihe. Z Anal Chem 244:7–17
Chialva F, Gabri G, Liddle PAP, Ulian F (1982) Qualitative evaluation of aromatic herbs dy direct headspace GC analysis. Applications of the method and comparison with the traditional analysis of essential oils. HRC and CC 5:182–188
Debrauwere J, Verzele M (1975) New constituents of the oxygenated fraction of pepper essential oil. J Sci Food Agric 26:1887–1894
De Pooter HL, Nor Omar M, Coolsaet BA, Schamp NM (1985) The essential oil of greater galanga (alpinia galanga) from malaysia. Phytochemistry 24:93–96
Enzell CR (1966) Mass spectrometric studies of diterpenes. 4 Aromatic diterpenes. Tetrahedron Lett 1966:2135–2143
Enzell CR, Ryhage R (1965) Mass spectrometric studies of diterpenes. 1 Carbodicyclic diterpenes. Ark Kemi 23:367–399
Enzell CR, Ryhage R (1967a) Mass spectrometric studies of diterpenes. 3 Aromatic diterpenes. Ark Kemi 26:425–434
Enzell CR, Ryhage R (1967b) Mass spectrometric studies of diterpenes. 5 Aromatic diter-penes. Ark Kemi 27:213–229
Enzell CR, Wahlberg I (1969) Mass spectrometric studies of diterpenes. 6 Aromatic diterpenes. Acta Chem Scand 23:871–891
Enzell CR, Wahlberg I (1980) Terpenes and terpenoids. In: Waller GR, Dermer OC (ed) Biochemical applications of mass spectrometry (1st suppl vol). Wiley-Interscience, New York, pp 311–406
Enzell CR, Appleton RA, Wahlberg I (1972) Terpenes and terpenoids. In: Waller GR (ed) Biochemical application of mass spectrometry. Wiley-Interscience, New York, pp 351–385
Enzell CR, Wahlberg I, Ryhage R (1984) Mass spectra of tobacco isoprenoids. Mass Spectrom Rev 3:395–438
Epstein WW, Gaudioso LA (1984) Volatile oil constituents of sagebrush. Phytochemistry 23:2257–2262
Gabri G, Chialva F (1981) Qualitative evaluation of aromatic herbs by direct head space (GC) analysis. Methodology and some preliminary applications. HRC and CC 4:215–217
Godefroot M, Sandra P, Verzele M (1981) New method for quantitative essential oil analysis. J Chromatogr 203:325–335
Harvey DJ (1977) Cyclic alkylboronates as derivatives for the characterization of cannabi- nolic acids by combined gas chromatography and mass spectrometry. BMS 4:88–93
Hendriks H, Bruins AP (1980) Study of three types of essential oil of valeriana officinalis L. s. 1 by combined gas chromatography-negative ion chemical ionization mass spectrometry. J Chromatogr 190:321–330
Hendriks H, Bruins AP (1983) A tentative identification of components in the essential oil of cannabis sativa L. by a combination of gas chromatography negative ion chemical ionization mass spectrometry and retention indices. BMS 10:377–381
Heupel RC, Phinney BO, Spray CR, Gaskin P, MacMillan J, Hedden P, Graebe JE (1985) Native gibberellins and the metabolism of [14C]gibberellin A53 and of [17–13C,17–3H2] gibberellin A20 in tassels of zea mays. Phytochemistry 24:47–53
Hill HC, Reed RI, Robert-Lopes MT (1968) Mass spectra and molecular structure. Part I. Correlation studies and meta-molecular structure. Part I. Correlation studies and metastable transitions. J Chem Soc C 1968:93–101
Hiltunen R, Vuorela H, Laakso I, v. Schantz M (1984) Application of headspace gas chromatography in essential oil analysis (IV). Quantitative analysis of a-bisabolol in volatiles of matricaria recutita L. Farm Tijdschr Belg 61:354–355
Hooper SN, Chandler RF, Lewis E, Jamieson WD (1982) Simultaneous determination of sonchus arvensis L. triterpenes by gas chromatography-mass spectrometry. Lipids 17:60–63
Ingram TJ, Reid JB, Murfet IC, Gaskin P, Willis CL, MacMillan J (1984) Internode length in pisum. The le gene controls the 3ß-hydroxylation of gibberellin A20 to gibberellin Al. Planta 160:455–463
Jennings W, Shibamoto T (1980) Qualitative analysis of flavor and fragrance volatiles by glass capillary gas chromatography. Academic, New York
Karlsen J, Siwon H (1975) Elution sequence as a function of temperature in the gas-liquid chromatography of monoterpene hydrocarbons. J Chromatogr 110:187–189
Kovâts E (1958) Gas-chromatographische Charakterisierung organischer Verbindungen Teil 1:Retentionsindices aliphatischer Halogenide, Alkohole, Aldehyde and Ketone. Helv Chim Acta 41:1915–1932
Lemberkovics É (1984) Gas chromatographic characterization of frequently occurring monoterpenes in essential oils. J Chromatogr 286:293–300
MacLeod AJ, Cave SJ (1975) Volatile flavor components of eggs. J Sci Food Agric 26:351–360
MacLeod AJ, Pieris NM (1982) Analysis of the volatile essential oils of murrays koenigii and pandanus latifolius. Phytochemistry 21:1653–1657
Majlât P, Erdös Z, Takâcs J (1974) Calculation and application of the retention indices in programmed-temperature gas chromatography. J Chromatogr 91:89–103
Maurer B, Grieder A (1977) Sesquiterpenoids from costus root oil (saussurea lappa Clarke). Helv Chim Acta 60:2177–2191
Mazza G (1983) Gas chromatographic-mass spectrometric investigation of the volatile components by myrtle berries (myrtus communis L.). J Chromatogr 264:304–311
Michaelis K, Vostrowsky O, Paulini H, Zintl R, Knobloch K (1982) On the essential oil components from blossoms of artemisia vulgaris L. Z Naturforsch 37c:152–158
Netting AG, Milborrow BV, Duffield AM (1982) Determination of abscisic acid in eucalyptus haemastoma leaves using gas chromatography-mass spectrometry and deuterated internal standards. Phytochemistry 21:385–389
Papageorgiou VP (1980) GLC-MS computer analysis of the essential oil of Thymus capitatus. Planta Med Suppl 1980:29–33
Perry NB, Weavers RT (1984) Kovats indices of diterpene hydrocarbons on fused-silica capillary columns. J Chromatogr 284:478–481
Roberts JB (1962) Elution sequence as a function of temperature in gas chromatography. Nature 193:1071–1072
Ryhage R, v. Sydow E (1963) Mass spectrometry of terpenes I. Monoterpene hydrocarbons. Acta Chem Scand 17:2025–2035
Saeed T, Redant G, Sandra P (1979) Kovats indices of monoterpene hydrocarbons on glass capillary columns. HRC and CC 2:75–76
Scheffer JJC, Baerheim Svendsen A (1975) Improved gas chromatographic analysis of naturally occurring monoterpene hydrocarbons following pre-fractionation by liquid-solid chromatography. J Chromatogr 115:607–611
Scheffer JJC, Koedam A, Baerheim Svendsen A (1976) Occurrence and prevention of isomerization of some monoterpene hydrocarbons from essential oils during liquid-solid chromatography on silica gel. Chromatographia 9:425–432
Shieh B, Matsubara Y (1981) Gas chromatography-mass spectrometry to the study of the sesquiterpenoids on the series of longifolanes, caryophyllanes, cadinanes, cedranes, longipinanes and thujopsanes. Shitsuryo Bunseki 29:97–111
Stahl E (1983) Pre-chromatographic procedure using mercury(II) acetate to separate satu-rated from unsaturated components in essential oil analysis. GIT Suppl 3:69–72
Stenhagen E, Abrahamsson S, McLafferty FW (1974) Registry of mass spectral data. Whi-ley-Interscience, New York
Thomas AF, Willhalm B (1964) Les spectres de masse dans l’analyse 3. Les spectres de masse des hydrocarbures monoterpeniques. Helv Chim Acta 47:475–488
v Sydow E (1963) Mass spectrometry of terpenes. II. Monoterpene alcohols. Acta Chem Scand 17:2504–2512
v Sydow E (1964) Mass spectrometry of terpenes. III. Monoterpene aldehydes and ketones. Acta Chem Scand 18:1099–1104
v Sydow E (1965) Mass spectrometry of terpenes. IV. Esters of monoterpene alcohols. Acta Chem Scand 19:2083–2088
Vostrowsky O, Brosche T, Ihm H, Zintl R, Knobloch K (1981) On the essential oil components from artemisia absinthium L. Z Naturforsch 36c:369–377
Weston RJ (1984) Composition of essential oil from leaves of eucalyptus delegatensis. Phytochemistry 23:1943–1945
Weyerstahl P, Kaul VK, Meier N, Weirauch M, Marschall H (1983) Volatile constituents of plectranthus rugosus leaf oil. Planta Med 48:99–102
Williams HJ, Strand MR, Bradleigh Vinson S (1981) Synthesis and purification of the allofarnesenes. Tetrahedron 37:2763–2767
Witte L, Berlin J, Wray V, Schubert W, Kohl W, Höfle G, Hammer J (1983) Mono-and diterpenes from cell cultures of thuja occidentalis. Planta Med 49:216–221
Yokouchi Y, Fujii T, Ambe Y, Fuwa K (1981) Determination of monoterpene hydrocar-bons in the atmosphere. J Chromatogr 209:293–298
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Witte, L. (1986). GC-MS Methods for Terpenoids. In: Linskens, H.F., Jackson, J.F. (eds) Gas Chromatography/Mass Spectrometry. Modern Methods of Plant Analysis, vol 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-82612-2_7
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DOI: https://doi.org/10.1007/978-3-642-82612-2_7
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