PROBLEMS OF QUALITATIVE AND QUANTITATIVE ANALYSIS OF PLANT VOLATILES
Abstract
Strategies for the analysis of plant volatiles have changed significantly over the past 15–20 years due to the introduction of new approaches to sample preparation and analysis, including approaches developed for other areas and currently applied to the analysis of plant metabolites. Any analysis of plant substances consists of two steps. The first step includes collection, primary processing, conservation, storage and extraction of plant material to prepare samples for research. The second step is the actual analysis of the samples by particular set of chromatographic, spectral and/or hybrid (hyphenated) techniques. Attention of scientific publications is usually focused on the second step, whereas the first step is "behind the scenes." However, it is at the first step that significant processes inside the biomaterial occur. It is impossible to correctly and adequately evaluate the final result of the research wthout regard to these processes. At both steps of research work, specific problems arise, the discussion of which is the subject of this review.
Wide distribution of the modern chromatographic instrumetns equipped with contemporary sofisticated software led to the fact that a significant part of the experiment is performed in an automatic mode. However, one must understand that improving the technique of the experiment does not change the basis of the method, and therefore does not eliminate the fundamental limitations of the method used. Therefore, to avoid errors in the publication of the results, all the experimental data obtained in an automatic mode should be subjected to an impartial revision by the experimenter taking into account all known limitations inherent in methods used for separation and detecting of components. In order to correctly interpret the data obtained, it is necessary to know the entire history of the sample under investigation, and for this, all manipulations with plant material — from collection of raw materials and to final sample preparation — must be carefully documented. Only in this case one can expect to receive meaningful research results.Downloads
Metrics
References
Bohlmann J. & Keeling C.I. The Plant Journal, 2008, vol. 54, No. 4, pp. 656–669. DOI: 10.1111/j.1365-313X.2008.03449.x
Schwab W., Davidovich-Rikanati R. & Lewinsohn E. The Plant Journal, 2008, vol. 54, no. 4, pp. 712–732. DOI: 10.1111/j.1365-313X.2008.03446.x
Morozov S.V., Tkacheva N.I., Tkachev A.V. Problemy kompleksnogo khimicheskogo profilirovaniia lekarstvennykh rastenii. Farmatsiia i farmakologiia. [Problems of complex chemical profiling of medicinal plants. Pharmacy and pharmacology]. 2017. (in press). (in Russ.).
Bicchi C., Cagliero C., Rubiolo P. Flavour and Fragrance Journal, 2011, vol. 26, no. 5, pp. 321–325. DOI: 10.1002/ffj.2059
Sgorbini B., Cagliero C., Boggia L., Liberto E., Reichenbach S. E., Rubiolo P., Cordero C., Bicchi C. Flavour and Fra-grance Journal, 2015, vol. 30, no. 5, pp. 366–380. DOI: 10.1002/ffj.3255
Harman-Ware A.E., Sykes R., Peter G.F., Davis M. Frontiers in Energy Research, 2016, vol. 4, pp. 2. DOI: 10.3389/fenrg.2016.00002
Tranchida P. Q., Franchina F. A. & Mondello L. Flavour and Fragrance Journal, 2017, vol. 32, no. 4, pp. 218–227. DOI: 10.1002/ffj.3383
Middleditch B.S. Analytical Artifacts: GC, MS, HPLC, TLC and PC. J. of Chromatography Library, vol. 44 Elsevier Sci-ence Ltd. 1989. 1033 p.
Jones W.P., Kinghorn A.D. Natural Products Isolation. Humana Press. 2005, pp. 323–351. DOI: 10.1385/1-59259-955-9:323
Tkachev A.V. Issledovanie letuchikh veshchestv rastenii. [Research of volatile substances of plants]. Novosibirsk, 2008, 969 p. (in Russ.).
Huopalahti R., Kesälahti E. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Es-sential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 179–184. DOI: 10.1007/978-94-009-5137-2_19
Tkachev A.V., Koroliuk E.A., Iusubov M.S., Gur'ev A.M. Khimiia rastitel'nogo syr'ia, 2002, no. 1, pp. 19–30. (in Russ.).
Utsumi S.A., Cibils A.F., Estell R.E., Wang Y.-F. Rangeland Ecology & Management, 2006, vol. 59, no. 6, pp. 668–673. DOI: 10.2111/06-010R1.1
Tkachev A.V., Prokusheva D.L., Domrachev D.V. Dikorastushchie efirnomaslichnye rasteniia Iuzhnoi Sibiri. [Wild-growing essential oil plants of Southern Siberia]. Novosibirsk, 2017, 575 p. (in Russ.).
Kubeczka K.-H. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 107–126. DOI: 10.1007/978-94-009-5137-2_9
Casteel D.A. Natural Product Reports, 1992, vol. 9, no. 4, pp. 289–312. DOI: 10.1039/NP9920900289
Casteel D.A. Natural Product Reports, 1999, vol. 16, no. 1, pp. 55–73. DOI: 10.1039/A705725C
Jung M., Kim H., Lee K., Park M. Mini Reviews in Medicinal Chemistry, 2003, vol. 3, no. 2, pp. 159–165. DOI: 10.2174/1389557033405313
Liu D.-Z., Liu J.-K. Natural Products and Bioprospecting, 2013. vol. 3, no. 5, pp. 161–206. DOI: 10.1007/s13659-013-0042-7
Bu M., Yang B.B., Hu L. Current medicinal chemistry, 2016, vol. 23, no. 4, pp. 383–405. DOI: 10.2174/0929867323666151127200949
Wolfenden R., Lu X., Young G. Journal of the American Chemical Society, 1998, vol. 120, no. 27, pp. 6814–6815. DOI: 10.1021/ja9813055
Zhang W.L., Chen J.-P., Lam K.Y.-C., Zhan J.Y.-X., Yao P., Dong T.T.-X., Tsim K.W.-K. Evidence-Based Complementary and Alternative Medicine, 2014, vol. 2014. DOI: 10.1155/2014/608721
Bolarinwa I.F., Oke M.O., Olaniyan S.A., Ajala A.S. Toxicology – New Aspects to This Scientific Conundrum. InTech, 2016, pp. 179–191. DOI: 10.5772/64886
Schmaus G., Kubeczka K.-H. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 127–134. DOI: 10.1007/978-94-009-5137-2_10
Baldermann S., Yang Z., Sakai M., Fleischmann P., Watanabe N. Floriculture and Ornamental Biotechnology, 2009, vol. 3, no. 1, pp. 89–97.
Jean F.-I., Garneau F.-X., Collin G.J., Bouhajib M., Zamir L.O. Journal of Essential Oil Research, 1993, vol. 5, no. 1, pp. 7–11. DOI: 10.1080/10412905.1993.9698163
Mastelić J., Miloš M., Kuštrak D., Radonić A. Croatica Chemica Acta, 1998. vol. 71, no. 1, pp. 147–154. URL: http://hrcak.srce.hr/132332
Mastelić J., Miloš M., Kuštrak D., Radonić A. Croatica Chemica Acta, 2000, vol. 73, no. 2, pp. 585–593. URL: http://hrcak.srce.hr/132073
Politeo O., Jukic M., Milos M. Journal of Food Biochemistry, 2010, vol. 34, no. 1, pp. 129–141. DOI: 10.1111/j.1745-4514.2009.00269.x
Sgorbini B., Cagliero C., Pagani A., Sganzerla M., Boggia L., Bicchi C., Rubiolo P. Phytochemistry, 2015, vol. 117, pp. 296–305. DOI: 10.1016/j.phytochem.2015.06.017
Tissier A. The Plant Journal, 2012, vol. 70, no. 1, pp. 51–68. DOI: 10.1111/j.1365-313X.2012.04913.x
Lange M.B., Turner G.W. Plant Biotechnology Journal, 2013, vol. 11, no. 1, pp. 2–22. DOI: 10.1111/j.1467-7652.2012.00737.x
Schilmiller A.L., Last R.L., Pichersky E. The Plant Journal, 2008, vol. 54, no. 4, pp. 702–711. DOI: 10.1111/j.1365-313X.2008.03432.x
Bicchi C., D' Amato A., Frattini C., Nano G. M., Cappelletti E., Caniato R. Journal of High Resolution Chromatography, 1985, vol. 8, no. 8, pp. 431–435. DOI: 10.1002/jhrc.1240080815
Fischer N., Nitz S., Drawert F. Flavour and Fragrance Journal, 1987, vol. 2, no. 2, pp. 55–61. DOI: 10.1002/ffj.2730020204
Toyota M., Koyama H., Mizutani M., Asakawa Y. Phytochemistry, 1996, vol. 41, no. 5, pp. 1347–1350. DOI: 10.1016/0031-9422(95)00798-9
Holloway P.J. The plant cuticle. Academic Press, London New York. 1982, pp. 45–84.
Boom A., Damsté J.S., de Leeuw J. Organic Geochemistry, 2005, vol. 36, no. 4, pp. 595–601. DOI: 10.1016/j.orggeochem.2004.10.017
Valkama E., Salminen J.-P., Koricheva J., Pihlaja K. Annals of Botany, 2003, vol. 91, no. 6, pp. 643–655. DOI: 10.1093/aob/mcg070
Guhling O., Kinzler C., Dreyer M., Bringmann G., Jetter R. Journal of Chemical Ecology, 2005, vol. 31, no. 10, pp. 2323–2341. DOI: 10.1007/s10886-005-7104-1
Can Baser K.H., Buchbauer G. Handbook of Essential Oils: Science, Technology, and Applications. Second Edition. CRC Press. 2016. 1095 p.
Matura M., Sköld M., Börje A., Andersen K.E., Bruze M., Frosch P., Goossens A., Johansen J.D., Svedman C., White I.R., Karlberg A.-T. Contact Dermatitis, 2005, vol. 52, no. 6, pp. 320–328. DOI: 10.1111/j.0105-1873.2005.00605.x
Christensson J.B., Matura M., Gruvberger B., Bruze M., Karlberg A.-T. Contact Dermatitis, 2010, vol. 62, no. 1, pp. 32–41. DOI: 10.1111/j.1600-0536.2009.01657.x
Bråred Christensson J., Andersen K.E., Bruze M., Johansen J.D., Garcia-Bravo B., Gimenez Arnau A., Goh C.-L., Nixon R., White I.R. Contact Dermatitis, 2012, vol. 67, no. 5, pp. 247–259. DOI: 10.1111/j.1600-0536.2012.02134.x
Bråred Christensson J., Karlberg A.-T., Andersen K.E., Bruze M., Johansen J.D., Garcia-Bravo B., Giménez Arnau A., Goh C.-L., Nixon R., White I.R. Contact Dermatitis, 2016, vol. 74, no. 5, pp. 273–280. DOI: 10.1111/cod.12545
Sköld M., Hagvall L., Karlberg A.-T. Contact Dermatitis, 2008, vol. 58, no. 1, pp. 9–14. DOI: 10.1111/j.1600-0536.2007.01262.x
Hagvall L., Berglund V., Bråred Christensson J. Contact Dermatitis, 2015, vol. 72, no. 4, pp. 216–223. DOI: 10.1111/cod.12350
Matura M., Goossens A., Bordalo O., Garcia-Bravo B., Magnusson K., Wrangsjö K., Karlberg A.-T. Contact Dermatitis, 2003, vol. 49, no. 1, pp. 15–21. DOI: 10.1111/j.0105-1873.2003.00135.x
Matura M., Sköld M., Börje A., Andersen K.E., Bruze M., Frosch P., Goossens A., Johansen J.D., Svedman C., White I.R., Karlberg A.-T. Contact Dermatitis, 2006, vol. 55, no. 5, pp. 274–279. DOI: 10.1111/j.1600-0536.2006.00939.x
Christensson J.B., Johansson S., Hagvall L., Jonsson C., Börje A. & Karlberg A.-T. Contact Dermatitis, 2008, vol. 59, no. 6, pp. 344–352. DOI: 10.1111/j.1600-0536.2008.01442.x
Bråred Christensson J., Andersen K.E., Bruze M., Johansen J.D., Garcia-Bravo B., Giménez-Arnau A., Goh C.-L., Nix-on R., White I.R. Contact Dermatitis, 2013, vol. 68, no. 4, pp. 214–223. DOI: 10.1111/cod.12036
Bråred Christensson J., Hellsén S., Börje A., Karlberg A.-T. Contact Dermatitis, 2014, vol. 70, no. 5, pp. 291–299. DOI: 10.1111/cod.12195
Niklasson I.B., Delaine T., Islam M.N., Karlsson R., Luthman K., Karlberg A.-T. Contact Dermatitis, 2013, vol. 68, no. 3, pp. 129–138. DOI: 10.1111/cod.12009
Rudbäck J., Hagvall L., Börje A., Nilsson U., Karlberg A.-T. Contact Dermatitis, 2014, vol. 70, no. 6, pp. 329–339. DOI: 10.1111/cod.12234
Hagvall L., Sköld M., Bråred-Christensson J., Börje A. & Karlberg A.-T. Contact Dermatitis, 2008, vol. 59, no. 3, pp. 143–150. DOI: 10.1111/j.1600-0536.2008.01402.x
Njoroge S.M., Ukeda H., Sawamura M. Journal of Agricultural and Food Chemistry, 1996, vol. 44, no. 2, pp. 550–556. DOI: 10.1021/jf950284k
Njoroge S.M., Ukeda H., Sawamura M. Journal of Agricultural and Food Chemistry, 2003, vol. 51, no. 14, pp. 4029–4035. DOI: 10.1021/jf021215q
Sun H., Ni H., Yang Y., Wu L., Cai H.-n., Xiao A.-f., Chen F. Journal of Agricultural and Food Chemistry, 2014, vol. 62, no. 49, pp. 11818–11830. DOI: 10.1021/jf504294g
Turek C., Stintzing F.C. Journal of Food Science, 2011, vol. 76, no. 9, pp. C1365–C1375. DOI: 10.1111/j.1750-3841.2011.02416.x
Turek C., Stintzing F.C. Comprehensive Reviews in Food Science and Food Safety, 2013, vol. 12, no. 1, pp. 40–53. DOI: 10.1111/1541-4337.12006
Kashiwagi T., Lan Phi N.T., Sawamura M. Food Science and Technology Research, 2010, vol. 16, no. 1, pp. 51–58. DOI: 10.3136/fstr.16.51
Takeda K., Horibe I., Minato H. J. Chem. Soc. D., 1971, no. 7, pp. 308. DOI: 10.1039/C29710000308
Reichardt P.B., Anderson B.J., Clausen T.P., Hoskins L.C. Canadian Journal of Chemistry, 1989, vol. 67, no. 7, pp. 1174–1177. DOI: 10.1139/v89-177
Garcia G., Charmillon J.-M., Roux E., Sutour S., Rakotozafy J. B., Désiré O., Paoli M., Tomi F., Rabehaja D.J.R. Journal of Essential Oil Research, 2017, vol. 29, no. 3, pp. 214–220. DOI: 10.1080/10412905.2016.1251982
Rabe P., Barra L., Rinkel J., Riclea R., Citron C.A., Klapschinski T.A., Janusko A., Dickschat J.S. Angewandte Chemie International Edition, 2015, vol. 54, no. 45, pp. 13448–13451. DOI: 10.1002/anie.201507615
Nilsson J., Carlberg J., Abrahamsson P., Hulthe G., Persson B.-A., Karlberg A.-T. Rapid Communications in Mass Spec-trometry, 2008, vol. 22, no. 22, pp. 3593–3598. DOI: 10.1002/rcm.3770
Valcárcel M., Cárdenas S., Simonet B., Carrillo-Carrión C. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 234–240. DOI: 10.1016/j.chroma.2007.03.034
Stashenko E.E., Martínez J.R. Gas Chromatography in Plant Science, Wine Technology, Toxicology and Some Specific Applications. InTech. 2012, pp. 247–270. DOI: 10.5772/32246
Chamorro E.R., Zambón S.N., Morales W.G., Sequeira A.F., Velasco G.A. Gas Chromatography in Plant Science, Wine Technology, Toxicology and Some Specific Applications. InTech. 2012, pp. 307–324. DOI: 10.5772/33201
Rubiolo P., Sgorbini B., Liberto E., Cordero C., Bicchi C. Flavour and Fragrance Journal, 2010, vol. 25, no. 5, pp. 282–290. DOI: 10.1002/ffj.1984
Jones C.E., Kato S., Nakashima Y., Kajii Y. Atmospheric Measurement Techniques, 2014, vol. 7, no. 5, pp. 1259–1275. DOI: 10.5194/amt-7-1259-2014
Kováts E. Helvetica Chimica Acta, 1958, vol. 41, no. 7, pp. 1915–1932. DOI: 10.1002/hlca.19580410703
Wick C.D., Siepmann J., Klotz W.L., Schure M.R. Journal of Chromatography A., 2002, vol. 954, no. 1, pp. 181–190. DOI: 10.1016/S0021-9673(02)00171-1
Héberger K. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 273–305. DOI: 10.1016/j.chroma.2007.03.108
van den Dool H., Kratz P.D. Journal of Chromatography, 1963, vol. 11, pp. 463–471. DOI: 10.1016/S0021-9673(01)80947-X
Bicchi C., Binello A., D'Amato A., Rubiolo P. Journal of Chromatographic Science, 1999, vol. 37, no. 8, pp. 288–294. DOI: 10.1093/chromsci/37.8.288
Analytical Methods Committee Application of Gas-Liquid Chromatography to the Analysis of Essential Oils. Part XVII. Fingerprinting of Essential Oils by Temperature-programmed Gas-Liquid Chromatography Using Capillary Columns With Non-polar Stationary Phases // Analyst. 1997, vol. 122, pp. 1167–1174. DOI: 10.1039/A704651K
Adams R.P. Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy, 4th Edition. Allured Publishing Corporation, Illinois, USA. 2007. 804 p.
Gonzalez F., Nardillo A. Journal of Chromatography A., 1999, vol. 842, no. 1, pp. 29–49. DOI: 10.1016/S0021-9673(99)00158-2
Ong R., Shellie R., Marriott P. Journal of Separation Science, 2001, vol. 24, no. 5, pp. 367–377. DOI: 10.1002/1615-9314(20010501)24:5<367::AID-JSSC367>3.0.CO;2-U
Western R.J., Marriott P.J. Journal of Separation Science, 2002, vol. 25, no. 13, pp. 831–838. DOI: 10.1002/1615-9314(20020901)25:13<831::AID-JSSC832>3.0.CO;2-R
Zenkevich I.G. 100 Let khromatografii. [100 Years of chromatography]. Ed. B.A. Rudenko. Moscow, 2003, pp. 311–336. (in Russ.).
Egolf L.M., Jurs P.C. Analytical Chemistry, 1993, vol. 65, no. 21, pp. 3119–3126. DOI: 10.1021/ac00069a027
Kaliszan R., Bączek T. Recent Advances in QSAR Studies: Methods and Applications. Springer Netherlands. 2010, pp. 223–259. DOI: 10.1007/978-1-4020-9783-6_8
Todeschini R., Consonni V. Handbook of Molecular Descriptors. WILEY-VCH Verlag GmbH. 2000. 667 p.
Beteringhe A., Radutiu A.C., Culita D.C., Mischie A., Spafiu F. QSAR & Combinatorial Science, 2008, vol. 27, no. 8, pp. 996–1005. DOI: 10.1002/qsar.200730097
Ausloos P., Clifton C., Lias S., Mikaya A., Stein S., Tchekhovskoi D., Sparkman O., Zaikin V., Zhu D. Journal of the American Society for Mass Spectrometry, 1999, vol. 10, no. 4, pp. 287–299. DOI: 10.1016/S1044-0305(98)00159-7
Lebedev A.T. Mass-spektrometriia v organicheskoi khimii. [Mass spectrometry in organic chemistry]. Moscow, 2003, 493 p. (in Russ.).
McAndrew B.A. Perfumer & Flavorist, 1992, vol. 17, no. 4, pp. 1–12.
Helmig D., Revermann T., Pollmann J., Kaltschmidt O., Hernández A. J., Bocquet F., David D. Journal of Chromatography A., 2003, vol. 1002, no. 1–2, pp. 193–211. DOI: 10.1016/S0021-9673(03)00619-8
Jacobsson U., Muddathir A.K. Phytochemistry, 1992, vol. 31, no. 12, pp. 4207–4211. DOI: 10.1016/0031-9422(92)80444-J
Zheng G.-Q., Kenney P.M., Lam L.K.T. Journal of Natural Products, 1992, vol. 55, no. 7, pp. 999–1003. DOI: 10.1021/np50085a029
Sabulal B., Dan M., Anil John J., Kurup R., Pradeep N.S., Valsamma R.K., George V. Phytochemistry, 2006, vol. 67, no. 22, pp. 2469–2473. DOI: 10.1016/j.phytochem.2006.08.003
Medeiros R., Passos G.F., Vitor C.E., Koepp J., Mazzuco T.L., Pianowski L.F., Campos M.M., Calixto J.B. British Journal of Pharmacology, 2007, vol. 151, no. 5, pp. 618–627. DOI: 10.1038/sj.bjp.0707270
Gertsch J., Leonti M., Raduner S., Racz I., Chen J.-Z., Xie X.-Q., Altmann K.-H., Karsak M., Zimmer A. Proceedings of the National Academy of Sciences, 2008, vol. 105, no. 26, pp. 9099–9104. DOI: 10.1073/pnas.0803601105
Langhasova L., Hanusova V., Rezek J., Stohanslova B., Ambroz M., Kralova V., Vanek T., Lou J. D., Yun Z. L., Yang J., Skalova L. Industrial Crops and Products, 2014, vol. 59, pp. 20–26. DOI: 10.1016/j.indcrop.2014.04.018
Klauke A.-L., Racz I., Pradier B., Markert A., Zimmer A., Gertsch J., Zimmer A. European Neuropsychopharmacology, 2014, vol. 24, no. 4, pp. 608–620. DOI: 10.1016/j.euroneuro.2013.10.008
Gubiani J.R., Zeraik M.L., Oliveira C.M., Ximenes V.F., Nogueira C.R., Fonseca L.M., Silva D.H.S., Bolzani V.S., Araujo A.R. Journal of Natural Products, 2014, vol. 77, no. 3, pp. 668–672. DOI: 10.1021/np400825s
Sarpietro M.G., Sotto A.D., Accolla M.L., Castelli F. Thermochimica Acta, 2015, vol. 600, pp. 28–34. DOI: 10.1016/j.tca.2014.11.029
Fidyt K., Fiedorowicz A., Strządała L., Szumny A. Cancer Medicine, 2016, vol. 5, no. 10, pp. 3007–3017. DOI: 10.1002/cam4.816
Joulain D., König W.A. Atlas of Spectral Data of Sesquiterpene Hydrocarbons. EB-Verlag. 2001. 658 p.
Lemberkovics É., Verzár-Petri G. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 103–105. DOI: 10.1007/978-94-009-5137-2_8
Sarker S.D., Nahar L. Natural Products Isolation. Humana Press. 2005, pp. 233–267. DOI: 10.1385/1-59259-955-9:233
Hubert J., Nuzillard J.-M., Renault J.-H. Phytochemistry Reviews, 2017, vol. 16, no. 1, pp. 55–95. DOI: 10.1007/s11101-015-9448-7
Marriott P.J., Massil T., Hügel H. Journal of Separation Science, 2004, vol. 27, no. 15-16, pp. 1273–1284. DOI: 10.1002/jssc.200401917
Pang T., Zhu S., Lu X., Xu G. Journal of Separation Science, 2007, vol. 30, no. 6, pp. 868–874. DOI: 10.1002/jssc.200600471
Shellie R., Marriott P., Cornwell C. Journal of Separation Science, 2001, vol. 24, no. 10-11, pp. 823–830. DOI: 10.1002/1615-9314(20011101)24:10/11<823::AID-JSSC823>3.0.CO;2-H
Cagliero C., Sgorbini B., Cordero C., Liberto E., Rubiolo P., Bicchi C. Israel Journal of Chemistry, 2016, vol. 56, no. 11-12, pp. 925–939. DOI: 10.1002/ijch.201600091
Tkachev A.V. Russian Chemical Reviews, 2007, vol. 76, no. 10, pp. 951–969. DOI: 10.1070/RC2007v076n10ABEH003728
de Juan A., Tauler R. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 184–195. DOI: 10.1016/j.chroma.2007.05.045
Baldovini N., Tomi F., Casanova J. Phytochemical Analysis, 2001, vol. 12, no. 1, pp. 58–63. DOI: 10.1002/1099-1565(200101/02)12:1<58::AID-PCA559>3.0.CO;2-9
Cavalli J.-F., Tomi F., Bernardini A.-F., Casanova J. Phytochemical Analysis, 2004, vol. 15, no. 5, pp. 275–279. DOI: 10.1002/pca.761
Blanc M.-C., Bradesi P., Casanova J. Phytochemical Analysis, 2005, vol. 16, no. 3, pp. 150–154. DOI: 10.1002/pca.834
Duquesnoy E., Castola V., Casanova J. Phytochemical Analysis, 2007, vol. 18, no. 4, pp. 347–353. DOI: 10.1002/pca.989
Ferrari B., Castilho P., Tomi F., Rodrigues A. I., do Ceu Costa M., Casanova J. Phytochemical Analysis, 2005, vol. 16, no. 2, pp. 104–107. DOI: 10.1002/pca.825
Duquesnoy E., Paoli M., Castola V., Bighelli A., Casanova J. Phytochemical Analysis, 2009, vol. 20, no. 3, pp. 246–252. DOI: 10.1002/pca.1121
Ratcliffe R.G., Roscher A., Shachar-Hill Y. Progress in Nuclear Magnetic Resonance Spectroscopy, 2001, vol. 39, no. 4, pp. 267–300. DOI: 10.1016/S0079-6565(01)00035-8
Lerche M.H., Jensen P.R., Karlsson M., Meier S. Analytical Chemistry, 2015, vol. 87, no. 1, pp. 119–132. DOI: 10.1021/ac501467x
Krishnan P., Kruger N. J., Ratcliffe R.G. Journal of Experimental Botany, 2005, vol. 56, no. 410, pp. 255–265. DOI: 10.1093/jxb/eri010
Kim H.K., Choi Y.H., Verpoorte R. Nature Protocols, 2010, vol. 5, pp. 536–549. DOI: 10.1038/nprot.2009.237
Bligny R., Douce R. Current Opinion in Plant Biology, 2001, vol. 4, no. 3, pp. 191–196. DOI: 10.1016/S1369-5266(00)00160-6
Eisenreich W., Bacher A. Phytochemistry, 2007, vol. 68, no. 22, pp. 2799–2815. DOI: 10.1016/j.phytochem.2007.09.028
Ristorcelli D., Tomi F., Casanova J. Flavour and Fragrance Journal, 1998, vol. 13, no. 3, pp. 154–158. DOI: 10.1002/(SICI)1099-1026(199805/06)13:3<154::AID-FFJ713>3.0.CO;2-2
Baldovini N., Tomi F., Casanova J. Phytochemical Analysis, 2003, vol. 14, no. 4, pp. 241–244. DOI: 10.1002/pca.710
Ravid U., Putievsky E., Weinstein V., Ikan R. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 135–138. DOI: 10.1007/978-94-009-5137-2_11
Lanfranchi D. A., Tomi F., Casanova J. Phytochemical Analysis, 2010, vol. 21, no. 6, pp. 597–601. DOI: 10.1002/pca.1240
Weinstein V., Ikan R., Ravid U., Putievsky E. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 139–143. DOI: 10.1007/978-94-009-5137-2_12
Wenzel T.J., Wilcox J.D. Chirality, 2003, vol. 15, no. 3, pp. 256–270. DOI: 10.1002/chir.10190
Wenzel T.J., Chisholm C.D. Chirality, 2011, vol. 23, no. 3, pp. 190–214. DOI: 10.1002/chir.20889
Silva M.S. Molecules, 2017, vol. 22, no. 2. DOI: 10.3390/molecules22020247
Guiochon G., Guillemin C. Quantitative Gas Chromatography for Laboratory Analyses and On-Line Process Control. Elsevier Science. 1988. 796 p.
Cuadros-Rodríguez L., Bagur-González M. G., Sánchez-Viñas M., González-Casado A., Gómez-Sáez A.M. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 33–46. DOI: 10.1016/j.chroma.2007.03.030
Ortiz M., Sarabia L. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 94–110. DOI: 10.1016/j.chroma.2007.04.047
Hibbert D.B. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 25–32. DOI: 10.1016/j.chroma.2007.03.021
Maroto A., Boqué R., Riu J., Rius F. TrAC Trends in Analytical Chemistry, 1999, vol. 18, no. 9–10, pp. 577–584. DOI: 10.1016/S0165-9936(99)00151-X
Maroto A., Riu J., Boqué R., Rius F.X. Analytica Chimica Acta, 1999, vol. 391, no. 2, pp. 173–185. DOI: 10.1016/S0003-2670(99)00111-7
Meyer V.R. Measurement uncertainty // Journal of Chromatography A. 2007, vol. 1158, no. 1–2, pp. 15–24. DOI: 10.1016/j.chroma.2007.02.082
González A.G., Herrador M.Á. TrAC Trends in Analytical Chemistryб 2007, vol. 26, no. 3, pp. 227–238. DOI: 10.1016/j.trac.2007.01.009
Feinberg M. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 174–183. DOI: 10.1016/j.chroma.2007.02.021
Vanatta L., Coleman D. Journal of Chromatography A., 2007, vol. 1158, no. 1–2, pp. 47–60. DOI: 10.1016/j.chroma.2007.02.040
Bicchi C., Liberto E., Matteodo M., Sgorbini B., Mondello L., Zellner B. d., Costa R., Rubiolo P. Flavour and Fragrance Journal, 2008, vol. 23, no. 6, pp. 382–391. DOI: 10.1002/ffj.1905
IOFI Working Group on Methods of Analysis Guidelines for the quantitative gas chromatography of volatile flavouring substances, from the Working Group on Methods of Analysis of the International Organization of the Flavor Industry (IOFI). Flavour and Fragrance Journal, 2011, vol. 26, no. 5, pp. 297–299. DOI: 10.1002/ffj.2061
Stoliarov B.V., Savinov I.M., Vitenberg A.G. Rukovodstvo k prakticheskim rabotam po gazovoi khromatografii. [A guide to practical work on gas chromatography]. Ed. B.V. Ioffe. Leningrad, 1988, 336 p. (in Russ.).
Sakodynskii K.I., Brazhnikov V.V., Volkov S.A., Zel'venskii V.Iu., Gankina E.S., Shatts V.D. Analiticheskaia khromatografiia. [Analytical chromatography]. Moscow, 1993, 464 p. (in Russ.).
Stoliarov B.V., Savinov I.M., Vitenberg A.G., Kartsova L.A., Zenkevich I.G., Kalmanovskii V.I., Kalambet Iu.A. Prakticheskaia gazovaia i zhidkostnaia khromatografiia. [Practical gas and liquid chromatography]. St. Petersburg, 2002, 616 p. (in Russ.).
Dietz W.A. Journal of Chromatographic Science, 1967, vol. 5, no. 2, pp. 68–71. DOI: 10.1093/chromsci/5.2.68
Raffa K.F., Steffeck R.J. Journal of Chemical Ecology, 1988, vol. 14, no. 5, pp. 1385–1390. DOI: 10.1007/BF01020142
Devaux P., Guiochon G. Journal of Chromatographic Science, 1969, vol. 7, no. 9, pp. 561–564. DOI: 10.1093/chromsci/7.9.561
Gislason J., Wharry S.M. Journal of Chromatographic Science, 2000, vol. 38, no. 3, pp. 129–132. DOI: 10.1093/chromsci/38.3.129
Brazhnikov V.V. Detektory dlia khromatografii. [Detectors for chromatography]. Moscow, 1992. 320 p. (in Russ.).
Goedert M., Guiochon G. Journal of Chromatographic Science, 1969, vol. 7, no. 6, pp. 323–339. DOI: 10.1093/chromsci/7.6.323
Hoffmann E.G. Analytical Chemistry, 1962, vol. 34, no. 10, pp. 1216–1222. DOI: 10.1021/ac60190a010
Herb S.F., Magidman P., Riemenschneider R.W. Journal of the American Oil Chemists' Society, 1967, vol. 44, no. 1, pp. 32–36. DOI: 10.1007/BF02908367
Liu F., Liang Y., Cao C. Chemometrics and Intelligent Laboratory Systems, 2006, vol. 81, no. 2, pp. 120–126. DOI: 10.1016/j.chemolab.2005.10.004
Tong H.Y., Karasek F.W. Analytical Chemistry, 1984, vol. 56, no. 12, pp. 2124–2128. DOI: 10.1021/ac00276a033
Ackman R.G. Journal of Chromatographic Science, 1968, vol. 6, no. 10, pp. 497–501. DOI: 10.1093/chromsci/6.10.497
Morvai M., Pályka I., Molnár-Perl I. Journal of Chromatographic Science, 1992, vol. 30, no. 11, pp. 448–452. DOI: 10.1093/chromsci/30.11.448
Ulberth F., Gabernig R.G., Schrammel F. Journal of the American Oil Chemists' Society, 1999, vol. 76, no. 2, pp. 263–266. DOI: 10.1007/s11746-999-0228-7
Kimball B.A., Russell J.H., Griffin D.L., Johnston J.J. Journal of Chromatographic Science, 2005, vol. 43, no. 5, pp. 253–258. DOI: 10.1093/chromsci/43.5.253
Scanlon J.T., Willis D.E. Journal of Chromatographic Science, 1985, vol. 23, no. 8, pp. 333–340. DOI: 10.1093/chromsci/23.8.333
Jones F.W. Journal of Chromatographic Science, 1998, vol. 36, no. 5, pp. 223–226. DOI: 10.1093/chromsci/36.5.223
Kállai M., Veres Z., Balla J. Chromatographia, 2001, vol. 54, no. 7, pp. 511–517. DOI: 10.1007/BF02491209
Slemr J., Slemr F., D'Souza H., Partridge R. Journal of Chromatography A., 2004, vol. 1061, no. 1, pp. 75–84. DOI: 10.1016/j.chroma.2004.10.037
Szulejko J.E., Kim Y.-H., Kim K.-H. Journal of Separation Science, 2013, vol. 36, no. 20, pp. 3356–3365. DOI: 10.1002/jssc.201300543
de Saint Laumer J.-Y., Cicchetti E., Merle P., Egger J., Chaintreau A. Analytical Chemistry, 2010, vol. 82, no. 15, pp. 6457–6462. DOI: 10.1021/ac1006574
Tissot E., Rochat S., Debonneville C., Chaintreau A. Flavour and Fragrance Journal, 2012, vol. 27, no. 4, pp. 290–296. DOI: 10.1002/ffj.3098
de Saint Laumer J.-Y., Leocata S., Tissot E., Baroux L., Kampf D. M., Merle P., Boschung A., Seyfried M., Chaintreau A. Journal of Separation Science, 2015, vol. 38, no. 18, pp. 3209–3217. DOI: 10.1002/jssc.201500106
Cao C., Huo P. Journal of Chromatographic Science, 2007, vol. 45, no. 6, pp. 360–368. DOI: 10.1093/chromsci/45.6.360
Jalali-Heravi M., Fatemi M. Journal of Chromatography A., 1998, vol. 825, no. 2, pp. 161–169. DOI: 10.1016/S0021-9673(98)00687-6
Balaban A.T. Chemical Physics Letters, 1982, vol. 89, no. 5, pp. 399–404. DOI: 10.1016/0009-2614(82)80009-2
Jalali-Heravi M., Fatemi M. Journal of Chromatography A., 2000, vol. 897, no. 1–2, pp. 227–235. DOI: 10.1016/S0021-9673(00)00793-7
Dojahn J.G., Wentworth W., Deming S.N., Stearns S.D. Journal of Chromatography A., 2001, vol. 917, no. 1–2, pp. 187–204. DOI: 10.1016/S0021-9673(01)00637-9
Khmel'nitskii R.A., Brodskii E.S. Khromato-mass-spektrometriia. [Chromato-mass spectrometry]. Moscow, 1984, 216 p. (in Russ.).
Ahn J.-W., Pandey S.K., Kim K.-H. Journal of Chromatographic Science, 2011, vol. 49, no. 1, pp. 19–28. DOI: 10.1093/chrsci/49.1.19
Göröcs N., Mudri D., Mátyási J., Balla J. Journal of Chromatographic Science, 2013, vol. 51, no. 2, pp. 138–145. DOI: 10.1093/chromsci/bms118
Jenke D., Odufu A. Journal of Chromatographic Science, 2012, vol. 50, no. 3, pp. 206–212. DOI: 10.1093/chromsci/bmr048
Davies S.R., Alamgir M., Chan B.K.H., Dang T., Jones K., Krishnaswami M., Luo Y., Mitchell P.S.R., Moawad M., Swan H., Tarrant G.J. Analytical and Bioanalytical Chemistry, 2015, vol. 407, no. 26, pp. 7983–7993. DOI: 10.1007/s00216-015-8971-0
Davies S.R., Jones K., Goldys A., Alamgir M., Chan B.K.H., Elgindy C., Mitchell P.S.R., Tarrant G.J., Krishnaswami M.R., Luo Y., Moawad M., Lawes D., Hook J.M. Analytical and Bioanalytical Chemistry, 2015, vol. 407, no. 11, pp. 3103–3113. DOI: 10.1007/s00216-014-7893-6
Guillemin C.L., Auricourt M.F., Du Crest J., Vermont J. Journal of Chromatographic Science, 1969, vol. 7, no. 8, pp. 493–499. DOI: 10.1093/chromsci/7.8.493
Estell R., Utsumi S., Cibils A. Animal Feed Science and Technology, 2010, vol. 158, no. 1–2, pp. 104–109. DOI: 10.1016/j.anifeedsci.2010.03.011
González-Bravo L., Marrero-Delange D., González-Guevara J. Journal of Chromatography A., 2000, vol. 888, no. 1–2, pp. 159–173. DOI: 10.1016/S0021-9673(00)00541-0
Pauli G.F. Phytochemical Analysis, 2001, vol. 12, no. 1, pp. 28–42. DOI: 10.1002/1099-1565(200101/02)12:1<28::AID-PCA549>3.0.CO;2-D
Singh S., Roy R. Expert Opinion on Drug Discovery, 2016, vol. 11, no. 7, pp. 695–706. DOI: 10.1080/17460441.2016.1189899
Chauthe S.K., Sharma R.J., Aqil F., Gupta R.C., Singh I.P. Phytochemical Analysis, 2012, vol. 23, no. 6, pp. 689–696. DOI: 10.1002/pca.2375
Simmler C., Napolitano J.G., McAlpine J.B., Chen S.-N., Pauli G.F. Current Opinion in Biotechnology, 2014, vol. 25, pp. 51–59. DOI: 10.1016/j.copbio.2013.08.004
Mo H., Harwood J., Zhang S., Xue Y., Santini R., Raftery D.R. Journal of Magnetic Resonance, 2009, vol. 200, no. 2, pp. 239–244. DOI: 10.1016/j.jmr.2009.07.004
Buschhaus C., Jetter R. Journal of Experimental Botany, 2011, vol. 62, no. 3, pp. 841–853. DOI: 10.1093/jxb/erq366
Sweeney E.G., Thompson R.E., Ford D.C. Journal of Chromatographic Science, 1970, vol. 8, no. 2, pp. 76–81. DOI: 10.1093/chromsci/8.2.76
Stuckey C.L. Journal of Chromatographic Science, 1978, vol. 16, no. 10, pp. 482–487. DOI: 10.1093/chromsci/16.10.482
Millar A.A., Smith M.A., Kunst L. Trends in Plant Science, 2000, vol. 5, no. 3, pp. 95–101. DOI: 10.1016/S1360-1385(00)01566-1
Walley J.W., Kliebenstein D.J., Bostock R.M., Dehesh K. Current Opinion in Plant Biology, 2013, vol. 16, no. 4, pp. 520–526. DOI: 10.1016/j.pbi.2013.06.011
Reina-Pinto J.J., Yephremov A. Plant Physiology and Biochemistry, 2009, vol. 47, no. 6, pp. 540–549. DOI: 10.1016/j.plaphy.2009.01.004
Ivankin A.N., Oliferenko G.L., Kulikovskii A.V., Chernukha I.M., Semenova A.A., Spiridonov K.I., Nasonova V.V. Journal of Analytical Chemistry, 2016, vol. 71, no. 11, pp. 1131–1137. DOI: 10.1134/S1061934816110046
Dodds E.D., McCoy M.R., Rea L.D., Kennish J.M. Lipids, 2005, vol. 40, no. 4, pp. 419–428. DOI: 10.1007/s11745-006-1399-8
Diehl J.W., DiSanzo F.P. Journal of Chromatographic Science, 2007, vol. 45, no. 10, pp. 690–693. DOI: 10.1093/chromsci/45.10.690
Sobrado L.A., Freije-Carrelo L., Moldovan M., Encinar J. R., Alonso J.I.G. Journal of Chromatography A., 2016, vol. 1457, pp. 134–143. DOI: 10.1016/j.chroma.2016.06.033
Cicchetti E., Merle P., Chaintreau A. Flavour and Fragrance Journal, 2008, vol. 23, no. 6, pp. 450–459. DOI: 10.1002/ffj.1906
Putievsky E., Ravid U., Husain S.Z. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 185–189. DOI: 10.1007/978-94-009-5137-2_20
Brunke E.-J., Hammerschmidt F.-J. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 145–150. DOI: 10.1007/978-94-009-5137-2_13
Verzár-Petri G., Then M., Mészáros S. Essential Oils and Aromatic Plants: Proceedings of the 15th International Symposium on Essential Oils, held in Noordwijkerhout, The Netherlands, July 19–21, 1984. Springer Netherlands. 1985, pp. 199–202. DOI: 10.1007/978-94-009-5137-2_22
Leocata S., Frank S., Wang Y., Calandra M.J., Chaintreau A. Flavour and Fragrance Journal, 2016, vol. 31, no. 4, pp. 329–335. DOI: 10.1002/ffj.3324
Rudbäck J., Islam N., Nilsson U., Karlberg A.-T. Journal of Separation Science, 2013, vol. 36, no. 8, pp. 1370–1378. DOI: 10.1002/jssc.201200855
Demyttenaere J.C.R. Flavour and Fragrance Journal, 2012, vol. 27, no. 1, pp. 3–12. DOI: 10.1002/ffj.2093
Cachet T., Brevard H., Chaintreau A., Demyttenaere J., French L., Gassenmeier K., Joulain D., Koenig T., Leijs H., Liddle P., Loesing G., Marchant M., Merle P., Saito K., Schippa C., Sekiya F., Smith T. Flavour and Fragrance Journal, 2016, vol. 31, no. 3, pp. 191–194. DOI: 10.1002/ffj.3311
Cachet T., Brevard H., Cantergiani E., Chaintreau A., Demyttenaere J., French L., Gassenmeier K., Joulain D., Koenig T., Leijs H., Liddle P., Loesing G., Marchant M., Saito K., Scanlan F., Schippa C., Scotti A., Sekiya F., Sherlock A., Smith T. Flavour and Fragrance Journal, 2015, vol. 30, no. 2, pp. 160–164. DOI: 10.1002/ffj.3222
Sousa J.P.B., Brancalion A.P., Souza A.B., Turatti I.C., Ambrósio S.R., Furtado N.A., Lopes N.P., Bastos J.K. Journal of Pharmaceutical and Biomedical Analysis, 2011, vol. 54, no. 4, pp. 653–659. DOI: 10.1016/j.jpba.2010.10.006
Zhu J.-J., An Y.-W., Hu G., Yin G.-P., Zhang Q.-W., Wang Z.-M. Molecules, 2013, vol. 18, no. 2, pp. 2110–2121. DOI: 10.3390/molecules18022110
Joó É., Dewulf J., Demarcke M., Amelynck C., Schoon N., Müller J.-F., Šimpraga M., Steppe K., Langenhove H.V. Inter-national Journal of Mass Spectrometry, 2010, vol. 291, no. 1–2, pp. 90–95. DOI: 10.1016/j.ijms.2010.01.018
Kang J.H., Kim M.E., Kim Y.D., Rhee Y.W., Lee S. Journal of Korean Society for Atmospheric Environment, 2016, vol. 32, no. 3, pp. 320–328. DOI: 10.5572/KOSAE.2016.32.3.320
Arh G., Klasinc L., Veber M., Pompe M. Journal of Chromatography A., 2011, vol. 1218, no. 11, pp. 1538–1543. DOI: 10.1016/j.chroma.2011.01.037
Faiola C.L., Erickson M.H., Fricaud V.L., Jobson B.T., VanReken T.M. Atmospheric Measurement Techniques, 2012, vol. 5, no. 8, pp. 1911–1923. DOI: 10.5194/amt-5-1911-2012
This work is licensed under a Creative Commons Attribution 4.0 International License.
The authors, which are published in this journal, agree to the following conditions:
1. Authors retain the copyright to the work and transfer to the journal the right of the first publication along with the work, at the same time licensing it under the terms of the Creative Commons Attribution License, which allows others to distribute this work with the obligatory indication of the authorship of this work and a link to the original publication in this journal .
2. The authors retain the right to enter into separate, additional contractual agreements for the non-exclusive distribution of the version of the work published by this journal (for example, to place it in the university depository or to publish it in a book), with reference to the original publication in this journal.
3. Authors are allowed to post their work on the Internet (for example, in a university repository or on their personal website) before and during the review process of this journal, as this may lead to a productive discussion, as well as more links to this published work.
