http://dx.doi.org/10.4322/sc.2012.004

 

GC-MS analysis of floral fragrance

Stashenko, Elena E.; Martínez, Jairo R.

Palavras-chave Floral scent, solid-phase microextraction, gas chromatography coupled to mass spectrometry, volatile organic compounds

ResumoThe diverse chemical features of floral fragrances are described and examples of the application of headspace, distillative and extraction methods most commonly used to isolate these mixtures of volatile organic compounds whose concentration varies between picograms and micrograms per liter are presented. Regarding the GC-MS analysis of floral fragrances, recommendations about their separation, detection and identification are presented together with examples.


Referências Bibliográficas

1. Dudareva NA, Pichersky E, editors. Biology of floral scent. Boca Raton: CRC, Taylor & Francis Group; 2006. 346 p.
2. Scopus. Base de datos. Elsevier; 2013. Consultada en 10-05-2013.
3. Stashenko EE, Martínez JR. Sampling flower scent for chromatographic analysis. Journal of Separation Science 2008; 31:2022-2031. http://dx.doi.org/10.1002/ jssc.200800151
4. Stashenko EE, Martínez JR. Sampling volatile compounds from natural products with headspace/ solid-phase micro-extraction. Journal of Biochemical and Biophysical Methods 2007; 70:235-242. http:// dx.doi.org/10.1016/j.jbbm.2006.08.011
5. Choi H-S. Characterization of Citrus unshiu (C. unshiu Marcov. Forma Miyagawa-wase) blossom aroma by solid-phase microextraction in conjunction with an electronic nose. Journal of Agricultural and Food Chemistry 2003; 51:418-423. http://dx.doi. org/10.1021/jf0114280
6. Knudsen JT, Eriksson R, Gershenzon J, Ståhl B. Diversity and distribution of floral scent. Botanical Review 2006.; 72:1-120. http://dx.doi.org/10.1663/0006- 8101.(2006)72[1:DADOFS]2.0.CO;2
7. Knudsen JT, Tollsten L, Bergstrom G. Floral scents – a checklist of volatile compounds isolated by headspace techniques. Phytochemistry 1993; 33:253-280. http://dx.doi.org/10.1016/0031-9422(93)85502-I
8. Knudsen JT, Gershenzon J. The chemical diversity of floral scent. In: Dudareva NA, Pichersky E, editors. Biology of floral scent. Boca Raton: CRC, Taylor & Francis Group; 2006. p. 40.
9. Tholl D, Boland W, Hansel A, Loreto F, Röse U, Schnitzler J-P. Practical approaches to plant volatile analysis. Plant Journal 2006; 45:540-560. http://dx.doi. org/10.1111/j.1365-313X.2005.02612.x
10. Augusto F, Leite e Lopes A, Zini C. Sampling and sample preparation for analysis of aromas and fragrances. Trends in Analytical Chemistry 2003; 22:160-169. http://dx.doi.org/10.1016/S0165-9936(03)00304-2
11. Barták P, Bednar P, Cáp L, Ondráková L, Stránský Z. SPME – A valuable tool for investigation of flower scent. Journal of Separation Science 2003; 26:715-721. http://dx.doi.org/10.1002/jssc.200301381
12. Flamini G, Cioni PL, Morelli I. Use of solid-phase micro-extraction as a sampling technique in the determination of volatiles emitted by flowers, isolated flower parts and pollen. Journal of Chromatography A 2003; 998:229-233. http://dx.doi.org/10.1016/ S0021-9673(03)00641-1
13. Fernando LN, Grün IU. Headspace-SPME analysis of volatiles of the ridge gourd (Luffa acutangula) and bitter gourd (Momordica charantia) flowers. Flavour and Fragrance Journal 2001; 16:289-293. http://dx.doi. org/10.1002/ffj.999
14. Xiang L, Milc JA, Pecchioni N, Chen L. Genetic aspects of floral fragrance in plants. Biochemistry (Moscow) 2007; 72:351-358. http://dx.doi.org/10.1134/ S0006297907040013
15. Bernhardt P, Sage T, Weston P, Azuma H, Lam M, Thiem L et al. The pollination of Trimenia moorei (Trimeniaceae): Floral volatiles, insect/wind pollen vectors and stigmatic self-incompatibility in a basal angiosperm. Annals of Botany 2003; 92:445-458. http://dx.doi.org/10.1093/aob/mcg157
16. Effmert U, Große J, Röse U, Ehrig F, Kägi R, Piechulla B. Volatile composition, emission pattern, and localization of floral scent emission in Mirabilis jalapa (Nyctaginaceae). American Journal of Botany 2005; 92:2-12. http://dx.doi.org/10.3732/ ajb.92.1.2
17. Granero AM, Egea Gonzalez FJ, Guerra Sanz JM, Martínez Vidal JL. Analysis of biogenic volatile organic compounds in zucchini flowers: identification of scent sources. Journal of Chemical Ecology 2005; 31:2309- 2322.. http://dx.doi.org/10.1007/s10886-005-7103-2
18. Stashenko EE, Torres W, Martínez JR. A study of the compositional variation of the essential oil of ylangylang (Cananga odorata Hook Fil. Et Thomson, forma genuina) during flower development. Journal of High Resolution Chromatography 1995; 18:101-104.
19. Stashenko EE, Quiroz N, Martínez JR. HRGC/FID/ NPD and HRGC/MSD study of Colombian ylangylang (Cananga odorata) oils obtained by different extraction techniques. Journal of High Resolution Chromatography 1996; 19:353-360. http://dx.doi. org/10.1002/jhrc.1240190609
20. Stashenko EE, Martínez JR, Macku C, Shibamoto T. HRGC and GC-MS Analysis of Essential Oil from Colombian Ylang-Ylang (Cananga odorata Hook Fil. et Thomson, forma genuina). Journal of High Resolution Chromatography 1993; 16:441-444. http:// dx.doi.org/10.1002/jhrc.1240160713
21. Schiestl FP, Ayasse M, Paulus HF, Lofstedt C, Hansson BS, Ibarra F et al. Orchid pollination by sexual swindle. Nature 1999; 399:421-422. http://dx.doi. org/10.1038/20829
22. Schiestl FP, Ayasse M. Post-pollination emission of a repellent compound in a sexually deceptive orchid: a new mechanism for maximizing reproductive success? Oecologia 2001; 126:531-534. http://dx.doi. org/10.1007/s004420000552
23. König WA. Chirality in the natural world—odours and tastes. In: Lough WJ, Wainer IW, editors. Chirality in Natural and Applied Sciences. Oxford: Blackwell Publishers; 2002. p. 261-84.
24. Acree TE, Barnard J. The analysis of odour-active volatiles in gas chromatographic effluents. In: Shreier P, editor. Analysis of Volatiles. Berlin: Gryter; 1984. p. 251-67.
25. Andersson S, Nilsson L A, Groth I, Bergström G. Floral scents in butterfly-pollinated plants: possible convergence in chemical composition. Botanical Journal of the Linnean Society 2002; 140:129-153. http://dx.doi.org/10.1046/j.1095-8339.2002.00068.x
26. Tollsten L, Bergström G. Fragrance chemotypes of Platanthera (Orchidaceae) – the result of adaptation to pollinating moths? Nordic Journal of Botany 1993; 13:607-613. http://dx.doi. org/10.1111/j.1756-1051.1993.tb00105.x
27. Surburg H, Güntert M, Schwarze B. Volatile constituents of European bird cherry flowers (Padus avium Mill.). Journal Essential Oil Research 1990; 2:307-316. http:// dx.doi.org/10.1080/10412905.1990.9697889
28. Dötterl S, Burkhardt D, Weißbecker B, Jürgens A, Schütz S, Mosandl A. Linalool and lilac aldehyde/ alcohol in flower scents. Electrophysiological detection of lilac aldehyde stereoisomers by a moth. Journal of Chromatography A 2006; 1113:231-238. http://dx.doi.org/10.1016/j.chroma.2006.02.011
29. Balao F, Herrera J, Talavera S, Dötterl S. Spatial and temporal patterns of floral scent emission in Dianthus inoxianus and electroantennographic responses of its hawkmoth pollinator. Phytochemistry 2011; 72:601-609. http://dx.doi. org/10.1016/j.phytochem.2011.02.001
30. Jennings W, Shibamoto T. Qualitative analysis of flavor and fragrance volátiles by glass capillary gas chromatography. New York: Academic Press; 1980.
31. Davies NW. Gas chromatographic retention indices of monoterpenes and sesquiterpenes on methyl silicon and Carbowax 20M phases. Journal of Chromatography A 1990; 503:1-24. http://dx.doi.org/10.1016/S0021- 9673.(01)81487-4
32. Adams RP. Identification of essential oil components by gas chromatography/quadrupole mass spectrometry. Carol Stream: Allured Publishing; 2001.
33. Joulain D, König WA. The atlas of spectral data of sesquiterpene hydrocarbons. Hamburg: E.-B. Verlag; 1998.
34. Acree T, Arn H. Flavornet and human odor space. Available from: http://www.flavornet.org.
35. Pherobase. Database of Pheromones and Semiochemicals. Available from: http://www. pherobase.com.
36. Stashenko EE, Martínez JR. Algunos aspectos prácticos para la identificación de analitos por cromatografía de gases acoplada a espectrometría de masas. Scientia Chromatographica 2010; 2:29-47.
37. Brokl M, Fauconnier M-L, Benini C, Lognay G, Du Jardin P, Focant J-F. Improvement of ylang-ylang essential oil characterization by GC×GC-TOFMS. Molecules 2013; 18:1783-1797. http://dx.doi. org/10.3390/molecules18021783.