Analytical and Bioanalytical Chemistry

, Volume 410, Issue 13, pp 3185–3196 | Cite as

Comprehensive 2D gas chromatography–time-of-flight mass spectrometry with 2D retention indices for analysis of volatile compounds in frankincense (Boswellia papyrifera)

Research Paper

Abstract

Frankincense gum resin secreted from Boswellia papyrifera was analysed by comprehensive 2D gas chromatography hyphenated with accurate mass time-of-flight mass spectrometry (GC×GC−accTOFMS). Direct multiple injection experiments with stepwise isothermal temperature programming were then performed to construct isovolatility curves for reference alkane series in GC×GC. This provides access to calculation of second dimensional retention indices (2I). More than 500 peaks were detected and 220 compounds mainly comprising monoterpenes, sesquiterpenes, diterpenes and oxygenated forms of these compounds were identified according to their 1I, 2I and accurate mass data. The study demonstrates the capability of GC×GC−accTOFMS with retention data on two separate column phases, as an approach for improved component identification. A greater number of identified and/or tentatively identified terpenoids in this traditional Chinese medicine allow for a more comprehensive coverage of the volatile composition of frankincense.

Keywords

Comprehensive 2D gas chromatography 2D index calculation Exact mass TOFMS Isovolatility Second dimension retention index 2D retention structure 

Abbreviations

GC

Gas chromatography

GC×GC

Comprehensive 2D gas chromatography

MS

Mass spectrometry

RI

Retention index

SPME

Solid-phase microextraction

TOF

Time-of-flight

Notes

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

216_2018_1012_MOESM1_ESM.pdf (949 kb)
ESM 1 (PDF 616 kb)

References

  1. 1.
    Al-Yasiry AR, Kiczorowska B. Frankincense—therapeutic properties. Postepy Hig Med Dosw (Online). 2016;70:380–91.CrossRefGoogle Scholar
  2. 2.
    Hosseini M, Hadjzadeh MA, Derakhshan M, Havakhah S, Rassouli FB, Rakhshandeh H, et al. The beneficial effects of olibanum on memory deficit induced by hypothyroidism in adult rats tested in Morris water maze. Arch Pharm Res. 2010;33:463–8.  https://doi.org/10.1007/s12272-010-0317-z.CrossRefGoogle Scholar
  3. 3.
    Sadhasivam S, Palanivel S, Ghosh S. Synergistic antimicrobial activity of Boswellia serrata Roxb. ex Colebr. (Burseraceae) essential oil with various azoles against pathogens associated with skin, scalp & nail infections. Lett Appl Microbiol. 2016;63:495–501.  https://doi.org/10.1111/lam.12683.CrossRefGoogle Scholar
  4. 4.
    Hartmann T. From waste products to ecochemicals: fifty years research of plant secondary metabolism. Phytochemistry. 2007;68:2831–46.  https://doi.org/10.1016/j.phytochem.2007.09.017.CrossRefGoogle Scholar
  5. 5.
    Anastasaki E, Kanakis C, Pappas C, Maggi L, del Campo CP, Carmona M, et al. Geographical differentiation of saffron by GC-MS/FID and chemometrics. Eur Food Res Technol. 2009;229:899–905.  https://doi.org/10.1007/s00217-009-1125-x.CrossRefGoogle Scholar
  6. 6.
    Jalali-Heravi M, Parastar H, Ebrahimi-Najafabadi H. Characterization of volatile components of Iranian saffron using factorial-based response surface modeling of ultrasonic extraction combined with gas chromatography-mass spectrometry analysis. J Chromatogr A. 2009;1216:6088–97.  https://doi.org/10.1016/j.chroma.2009.06.067.CrossRefGoogle Scholar
  7. 7.
    D’Auria M, Mauriello G, Rana GL. Volatile organic compounds from saffron. Flav Fragr J. 2004;19:17–23.  https://doi.org/10.1002/ffj.1266.CrossRefGoogle Scholar
  8. 8.
    Al-Harrasi A, Al-Saidi S. Phytochemical analysis of the essential oil from botanically certified oleogum resin of Boswellia sacra (Omani Luban). Molecules. 2008;13:2181–9.  https://doi.org/10.3390/molecules13092181.CrossRefGoogle Scholar
  9. 9.
    Hamm S, Lesellier E, Bleton J, Tchapla A. Optimization of headspace solid phase microextraction for gas chromatography/mass spectrometry analysis of widely different volatility and polarity terpenoids in olibanum. J Chromatogr A. 2003;1018:73–83.  https://doi.org/10.1016/j.chroma.2003.08.027.CrossRefGoogle Scholar
  10. 10.
    Niebler J, Buettner A. Frankincense revisited, part I: comparative analysis of volatiles in commercially relevant Boswellia species. Chem Biodivers. 2016;13:613–29.  https://doi.org/10.1002/cbdv.201500329.CrossRefGoogle Scholar
  11. 11.
    Niebler J, Buettner A. Identification of odorants in frankincense (Boswellia sacra Flueck.) by aroma extract dilution analysis and two-dimensional gas chromatography-mass spectrometry/olfactometry. Phytochemistry. 2015;109:66–75.  https://doi.org/10.1016/j.phytochem.2014.10.030.CrossRefGoogle Scholar
  12. 12.
    Hamm S, Bleton J, Connan J, Tchapla A. A chemical investigation by headspace SPME and GC-MS of volatile and semi-volatile terpenes in various olibanum samples. Phytochemistry. 2005;66:1499–514.  https://doi.org/10.1016/j.phytochem.2005.04.025.CrossRefGoogle Scholar
  13. 13.
    Marriott PJ, Chin S-T, Maikhunthod B, Schmarr H-G, Bieri S. Multidimensional gas chromatography. TrAC Trends Anal Chem. 2012;34:1–21.  https://doi.org/10.1016/j.trac.2011.10.013.CrossRefGoogle Scholar
  14. 14.
    Chin S-T, Marriott PJ. Multidimensional gas chromatography beyond simple volatiles separation. Chem Commun. 2014;50:8819–33.  https://doi.org/10.1039/c4cc02018a.CrossRefGoogle Scholar
  15. 15.
    Ochiai N, Ieda T, Sasamoto K, Takazawa Y, Hashimoto S, Fushimi A, et al. Stir bar sorptive extraction and comprehensive two-dimensional gas chromatography coupled to high-resolution time-of-flight mass spectrometry for ultra-trace analysis of organochlorine pesticides in river water. J Chromatogr A. 2011;1218:6851–60.  https://doi.org/10.1016/j.chroma.2011.08.027.CrossRefGoogle Scholar
  16. 16.
    Chin S-T, Novachai Y, Marriott PJ. Enantiomeric separation in comprehensive two-dimensional gas chromatography with accurate mass analysis. Chirality. 2014;26:747–53.  https://doi.org/10.1002/chir.22280.CrossRefGoogle Scholar
  17. 17.
    Mezcua M, Malato O, Garcia-Reyes JF, Molina-Diaz A, Fernandez-Alba AR. Accurate-mass databases for comprehensive screening of pesticide residues in food by fast liquid chromatography time-of-flight mass spectrometry. Anal Chem. 2009;81:913–29.  https://doi.org/10.1021/ac801411t.CrossRefGoogle Scholar
  18. 18.
    Mitrevski B, Marriott PJ. Evaluation of quadrupole-time-of-flight mass spectrometry in comprehensive two-dimensional gas chromatography. J Chromatogr A. 2014;1362:262–9.  https://doi.org/10.1016/j.chroma.2014.08.053.CrossRefGoogle Scholar
  19. 19.
    Wong YF, Perlmutter P, Marriott PJ. Untargeted metabolic profiling of eucalyptus spp. leaf oils using comprehensive two-dimensional gas chromatography with high resolution mass spectrometry: expanding the metabolic coverage. Metabolomics. 2017;13(5)  https://doi.org/10.1007/s11306-017-1173-3.
  20. 20.
    Wong YF, Marriott PJ. Approaches and challenges for analysis of flavor and fragrance volatiles. J Agric Food Chem. 2017;65:7305–7.  https://doi.org/10.1021/acs.jafc.7b03112.CrossRefGoogle Scholar
  21. 21.
    Jiang M, Kulsing C, Nolvachai Y, Marriott PJ. Two-dimensional retention indices improve component identification in comprehensive two-dimensional gas chromatography of saffron. Anal Chem. 2015;87:5753–61.  https://doi.org/10.1021/acs.analchem.5b00953.CrossRefGoogle Scholar
  22. 22.
    Kulsing C, Nolvachai Y, Zeng AX, Chin S-T, Mitrevski B, Marriott PJ. From molecular structures of ionic liquids to predicted retention of fatty acid methyl esters in comprehensive two-dimensional gas chromatography. ChemPlusChem. 2014;79:790–7.  https://doi.org/10.1002/cplu.201300410.CrossRefGoogle Scholar
  23. 23.
    Beens J, Tijssen R, Blomberg J. Prediction of comprehensive two-dimensional gas chromatographic separations. A theoretical and practical exercise. J Chromatogr A. 1998;822:233–51.  https://doi.org/10.1016/S0021-9673(98)00649-9.CrossRefGoogle Scholar
  24. 24.
    Nolvachai Y, Kulsing C, Marriott PJ. Thermally sensitive behavior explanation for unusual orthogonality observed in comprehensive two-dimensional gas chromatography comprising a single ionic liquid stationary phase. Anal Chem. 2015;87:538–44.  https://doi.org/10.1021/ac5030039.CrossRefGoogle Scholar
  25. 25.
    Bieri S, Marriott PJ. Generating multiple independent retention index data in dual-secondary column comprehensive two-dimensional gas chromatography. Anal Chem. 2006;78:8089–97.  https://doi.org/10.1021/ac060869l.CrossRefGoogle Scholar
  26. 26.
    Bieri S, Marriott PJ. Dual-injection system with multiple injections for determining bidimensional retention indexes in comprehensive two-dimensional gas chromatography. Anal Chem. 2008;80:760–8.  https://doi.org/10.1021/ac071367q.CrossRefGoogle Scholar
  27. 27.
    Marriott PJ, Massil T, Hügel H. Molecular structure based retention relationships in comprehensive two-dimensional gas chromatography. J Sep Sci. 2004;27:1273–84.  https://doi.org/10.1002/jssc.200401917.CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Ming Jiang
    • 1
  • Chadin Kulsing
    • 2
    • 3
  • Philip J. Marriott
    • 2
  1. 1.School of Pharmacy, Tongji Medical CollegeHuazhong University of Science & TechnologyWuhanChina
  2. 2.Australian Centre for Research on Separation Science, School of ChemistryMonash UniversityClaytonAustralia
  3. 3.Department of Chemistry, Faculty of ScienceChulalongkorn UniversityBangkokThailand

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