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Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS

Year 2025, , 63 - 71, 28.03.2025
https://doi.org/10.19159/tutad.1630871

Abstract

This study, the chemical composition of pine resin collected from three different locations (Kaburgediği, Karabucak and Mavisilifke) of Mersin province in the Mediterranean Region of Türkiye was investigated using headspace/GC-MS and direct injection/GC-MS techniques. A commercial essential oil was used as a control sample in the study. The analysis focused on key volatile compounds, including α-pinene, delta-3-carene, camphene, DL-limonene (mixture of D- and L-form), and caryophyllene. The headspace/GC-MS method was more effective for detecting compounds with higher volatility, such as α-pinene, which was more abundant in Karabucak (66.12% in headspace vs. 53.13% in direct injection). On the other hand, direct injection/GC-MS provided higher sensitivity for less volatile compounds, such as caryophyllene (4.82% in direct injection vs. 0.67% in headspace in Kaburgediği). The most significant difference between the methods was observed in the detection of DL-limonene, which showed higher concentrations in direct injection/GC-MS (3.76% in Mavisilifke) compared to headspace/GC-MS (1.51%). This suggests that direct injection/GC-MS is better for quantifying compounds with lower volatility, while headspace/GC-MS is more effective in capturing the overall aroma profile, especially for volatile compounds. This highlights the difference in efficiency and sensitivity based on the compound's volatility. Therefore, choosing the right method depends on the specific compounds of interest and their volatility characteristics. These findings highlight the unique volatile profiles of each resin, shaped by both the species and the analytical method used, with implications for their aromatic and potential pharmacological properties.

References

  • Alonso-Esteban, J.I., Carocho, M., Barros, D., Velho, M.V., Heleno, S., Barros, L., 2022. Chemical composition and industrial applications of Maritime pine (Pinus pinaster Ait.) bark and other non-wood parts. Reviews in Environmental Science and Bio/Technology, 21(3): 583-633.
  • Alves-Silva, J.M., Zuzarte, M., Girão, H., Salgueiro, L., 2021. The role of essential oils and their main compounds in the management of cardiovascular disease risk factors. Molecules, 26(12): 3506.
  • Ancuceanu, R., Anghel, A.I., Hovaneț, M.V., Ciobanu, A.M., Lascu, B.E., Dinu, M., 2024. Antioxidant activity of essential oils from Pinaceae species. Antioxidants, 13(3): 286.
  • Anonymous, 2024. Geography-Mersin Province. Republic of Turkey Ministry of Culture and Tourism, Mersin Cultural Center, (https://mersinkulturmerkezi.ktb.gov.tr/TR-162025/cografya.html), (Accessed: 24.01.2024). (In Turkish).
  • Antonelli, M., Donelli, D., Barbieri, G., Valussi, M., Maggini, V., Firenzuoli, F., 2020. Forest volatile organic compounds and their effects on human health: A state-of-the-art review. International Journal of Environmental Research and Public Health, 17(18): 6506.
  • Bleton, J., Tchapla, A., 2009. SPME/GC-MS in the characterisation of terpenic resins. In: M.P. Colombini and F. Modugno (Eds.), Organic Mass Spectrometry in Art and Archaeology, Wiley, pp. 261-302.
  • Clark, E.L., Pitt, C., Carroll, A.L., Lindgren, B.S., Huber, D.P., 2014. Comparison of lodgepole and jack pine resin chemistry: Implications for range expansion by the mountain pine beetle. Dendroctonus ponderosae (Coleoptera: Curculionidae). PeerJ, 2: e240.
  • Francezon, N., Stevanovic, T., 2018. Conifer resins and essential oils: Chemical composition and applications. In: T. Stevanovic (Ed.), Chemistry of Lignocellulosics: Current Trends, 1 st Edn., CRC Press, Boca Raton, pp. 231-252.
  • Górecki, T., Pawliszyn, J., 1995. Solid phase microextraction/isothermal GC for rapid analysis of complex organic samples. Journal of High Resolution Chromatography, 18(3): 161-166.
  • Gök, M., Başar, Y., 2023. Analysis of volatile components of the body, leave and flower parts of the fresh Ocimum basilicum plant growing in Siirt conditions by RSH-GC-MS. IV. International Siirt Conference on Scientific Research, Proceding Book, 17-18 November, Siirt University, Siirt, Türkiye, pp. 567-574.
  • Ioannou, E., Koutsaviti, A., Tzakou, O., Roussis, V., 2014. The genus Pinus: A comparative study on the needle essential oil composition of 46 pine species. Phytochemistry Reviews, 13: 741-768.
  • Jin, Q., O’Hair, J., Stewart, A.C., O’Keefe, S.F., Neilson, A.P., Kim, Y.T., McGuire, M., Lee, A., Wilder, G., Huang, H., 2019. Compositional characterization of different industrial white and red grape pomaces in Virginia and the potential valorization of the major components. Foods. 8(12): 667.
  • Kim, H., Choi, K.R., Yun, K.W., 2014. Analysis of the volatile components of three Pinus species by headspace/GC-MS. Journal of Essential Oil Bearing Plants, 17(6): 1241-1248.
  • Kristenson, E.M., Neidig, H.C., Vreuls, R.J., Brinkman, U.A.T., 2005. Fast miniaturised sample preparation for the screening and comprehensive two‐dimensional gas chromatographic determination of polychlorinated biphenyls in sludge. Journal of Separation Science, 28(11): 1121-1128.
  • Nakas, A., Virgiliou, C., Samara, D., Kechri, E., Assimopoulou, A.N., 2024. Exploring the effect of Pinus halepensis resin quality on the vinification of Retsina by untargeted profile analysis. Exploration of Foods and Foodomics, 2(5): 497-524.
  • Raber, A.G., Peachey-Stoner, R.J., Cessna, S.G., Siderhurst, M.S., 2021. Headspace GC-MS analysis of differences in intra- and interspecific terpene profiles of Picea pungens Engelm. and P. abies (L.) Karst. Phytochemistry, 181: 112541.
  • Ricardi, C., Barachini, S., Consoli, G., Marazziti, D., Polini, B., Chiellini, G., 2024. Beta-caryophyllene, a cannabinoid receptor type 2 selective agonist, in emotional and cognitive disorders. International Journal of Molecular Sciences, 25(6): 3203.
  • Ross, C.F., 2012. Headspace analysis. Comprehensive sampling and sample preparation. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2(02): 27-50.
  • Siddiqui, T., Sharma, V., Khan, M.U., Gupta, K., 2024. Terpenoids in essential oils: Chemistry, classification, and potential impact on human health and industry. Phytomedicine Plus, 4(2): 100549.
  • Swamy, M.K., Pullaiah, T., Dey, A., 2023. Frankincense (Olibanum): An aromatic resin with economic importance. In: M.K. Swamy, T. Pullaiah and A. Dey (Eds.), Frankincense (Olibanum), 1st Edn., Apple Academic Press, pp. 1-10.
  • Trapp, S., Croteau, R., 2001. Defensive resin biosynthesis in conifers. Annual Review of Plant Biology, 52(1): 689-724.
  • Velasco-García, M.V., Hernández-Hernández, A., 2024. Geographic and climatic variation in resin components and quality of Pinus oocarpa in Southern Mexico provenances. Plants, 13(13): 1755.
  • Wang, H.-Y., Guo, Y.-L., 2004. Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace‐gas chromatography-tandem mass spectrometry. Analytical Letters, 37(10): 2151-2161.
  • Wardencki, W., Chmiel, T., Dymerski, T., 2013. Gas chromatography-olfactometry (GC-O), electronic noses (e-noses) and electronic tongues (e-tongues) for in vivo food flavour measurement. In: D. Kilcast (Ed.), Instrumental Assessment of Food Sensory Quality: A Practical Guide, A Volume in Woodhead Publishing Series in Food Science, Technology and Nutrition, pp. 195-229.
  • Yu, J.J., Su, J., Li, F., Gao, J.L., Li, B., Pang, M.X., Lv, G.Y., Chen, S.H., 2017. Identification and quantification of pine needle essential oil from different habitats and species of china by GC-MS and GC method. African Journal of Traditional, Complementary and Alternative Medicines, 14(6): 1-9.
  • Zhang, P., Piergiovanni, M., Franceschi, P., Mattivi, F., Vrhovsek, U., Carlin, S., 2023. Application of comprehensive 2D gas chromatography coupled with mass spectrometry in beer and wine VOC analysis. Analytica, 4(3): 347-373.

Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS

Year 2025, , 63 - 71, 28.03.2025
https://doi.org/10.19159/tutad.1630871

Abstract

This study, the chemical composition of pine resin collected from three different locations (Kaburgediği, Karabucak and Mavisilifke) of Mersin province in the Mediterranean Region of Türkiye was investigated using headspace/GC-MS and direct injection/GC-MS techniques. A commercial essential oil was used as a control sample in the study. The analysis focused on key volatile compounds, including α-pinene, delta-3-carene, camphene, DL-limonene (mixture of D- and L-form), and caryophyllene. The headspace/GC-MS method was more effective for detecting compounds with higher volatility, such as α-pinene, which was more abundant in Karabucak (66.12% in headspace vs. 53.13% in direct injection). On the other hand, direct injection/GC-MS provided higher sensitivity for less volatile compounds, such as caryophyllene (4.82% in direct injection vs. 0.67% in headspace in Kaburgediği). The most significant difference between the methods was observed in the detection of DL-limonene, which showed higher concentrations in direct injection/GC-MS (3.76% in Mavisilifke) compared to headspace/GC-MS (1.51%). This suggests that direct injection/GC-MS is better for quantifying compounds with lower volatility, while headspace/GC-MS is more effective in capturing the overall aroma profile, especially for volatile compounds. This highlights the difference in efficiency and sensitivity based on the compound's volatility. Therefore, choosing the right method depends on the specific compounds of interest and their volatility characteristics. These findings highlight the unique volatile profiles of each resin, shaped by both the species and the analytical method used, with implications for their aromatic and potential pharmacological properties.

References

  • Alonso-Esteban, J.I., Carocho, M., Barros, D., Velho, M.V., Heleno, S., Barros, L., 2022. Chemical composition and industrial applications of Maritime pine (Pinus pinaster Ait.) bark and other non-wood parts. Reviews in Environmental Science and Bio/Technology, 21(3): 583-633.
  • Alves-Silva, J.M., Zuzarte, M., Girão, H., Salgueiro, L., 2021. The role of essential oils and their main compounds in the management of cardiovascular disease risk factors. Molecules, 26(12): 3506.
  • Ancuceanu, R., Anghel, A.I., Hovaneț, M.V., Ciobanu, A.M., Lascu, B.E., Dinu, M., 2024. Antioxidant activity of essential oils from Pinaceae species. Antioxidants, 13(3): 286.
  • Anonymous, 2024. Geography-Mersin Province. Republic of Turkey Ministry of Culture and Tourism, Mersin Cultural Center, (https://mersinkulturmerkezi.ktb.gov.tr/TR-162025/cografya.html), (Accessed: 24.01.2024). (In Turkish).
  • Antonelli, M., Donelli, D., Barbieri, G., Valussi, M., Maggini, V., Firenzuoli, F., 2020. Forest volatile organic compounds and their effects on human health: A state-of-the-art review. International Journal of Environmental Research and Public Health, 17(18): 6506.
  • Bleton, J., Tchapla, A., 2009. SPME/GC-MS in the characterisation of terpenic resins. In: M.P. Colombini and F. Modugno (Eds.), Organic Mass Spectrometry in Art and Archaeology, Wiley, pp. 261-302.
  • Clark, E.L., Pitt, C., Carroll, A.L., Lindgren, B.S., Huber, D.P., 2014. Comparison of lodgepole and jack pine resin chemistry: Implications for range expansion by the mountain pine beetle. Dendroctonus ponderosae (Coleoptera: Curculionidae). PeerJ, 2: e240.
  • Francezon, N., Stevanovic, T., 2018. Conifer resins and essential oils: Chemical composition and applications. In: T. Stevanovic (Ed.), Chemistry of Lignocellulosics: Current Trends, 1 st Edn., CRC Press, Boca Raton, pp. 231-252.
  • Górecki, T., Pawliszyn, J., 1995. Solid phase microextraction/isothermal GC for rapid analysis of complex organic samples. Journal of High Resolution Chromatography, 18(3): 161-166.
  • Gök, M., Başar, Y., 2023. Analysis of volatile components of the body, leave and flower parts of the fresh Ocimum basilicum plant growing in Siirt conditions by RSH-GC-MS. IV. International Siirt Conference on Scientific Research, Proceding Book, 17-18 November, Siirt University, Siirt, Türkiye, pp. 567-574.
  • Ioannou, E., Koutsaviti, A., Tzakou, O., Roussis, V., 2014. The genus Pinus: A comparative study on the needle essential oil composition of 46 pine species. Phytochemistry Reviews, 13: 741-768.
  • Jin, Q., O’Hair, J., Stewart, A.C., O’Keefe, S.F., Neilson, A.P., Kim, Y.T., McGuire, M., Lee, A., Wilder, G., Huang, H., 2019. Compositional characterization of different industrial white and red grape pomaces in Virginia and the potential valorization of the major components. Foods. 8(12): 667.
  • Kim, H., Choi, K.R., Yun, K.W., 2014. Analysis of the volatile components of three Pinus species by headspace/GC-MS. Journal of Essential Oil Bearing Plants, 17(6): 1241-1248.
  • Kristenson, E.M., Neidig, H.C., Vreuls, R.J., Brinkman, U.A.T., 2005. Fast miniaturised sample preparation for the screening and comprehensive two‐dimensional gas chromatographic determination of polychlorinated biphenyls in sludge. Journal of Separation Science, 28(11): 1121-1128.
  • Nakas, A., Virgiliou, C., Samara, D., Kechri, E., Assimopoulou, A.N., 2024. Exploring the effect of Pinus halepensis resin quality on the vinification of Retsina by untargeted profile analysis. Exploration of Foods and Foodomics, 2(5): 497-524.
  • Raber, A.G., Peachey-Stoner, R.J., Cessna, S.G., Siderhurst, M.S., 2021. Headspace GC-MS analysis of differences in intra- and interspecific terpene profiles of Picea pungens Engelm. and P. abies (L.) Karst. Phytochemistry, 181: 112541.
  • Ricardi, C., Barachini, S., Consoli, G., Marazziti, D., Polini, B., Chiellini, G., 2024. Beta-caryophyllene, a cannabinoid receptor type 2 selective agonist, in emotional and cognitive disorders. International Journal of Molecular Sciences, 25(6): 3203.
  • Ross, C.F., 2012. Headspace analysis. Comprehensive sampling and sample preparation. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2(02): 27-50.
  • Siddiqui, T., Sharma, V., Khan, M.U., Gupta, K., 2024. Terpenoids in essential oils: Chemistry, classification, and potential impact on human health and industry. Phytomedicine Plus, 4(2): 100549.
  • Swamy, M.K., Pullaiah, T., Dey, A., 2023. Frankincense (Olibanum): An aromatic resin with economic importance. In: M.K. Swamy, T. Pullaiah and A. Dey (Eds.), Frankincense (Olibanum), 1st Edn., Apple Academic Press, pp. 1-10.
  • Trapp, S., Croteau, R., 2001. Defensive resin biosynthesis in conifers. Annual Review of Plant Biology, 52(1): 689-724.
  • Velasco-García, M.V., Hernández-Hernández, A., 2024. Geographic and climatic variation in resin components and quality of Pinus oocarpa in Southern Mexico provenances. Plants, 13(13): 1755.
  • Wang, H.-Y., Guo, Y.-L., 2004. Rapid analysis of the volatile compounds in the rhizomes of Rhodiola sachalinensis and Rhodiola sacra by static headspace‐gas chromatography-tandem mass spectrometry. Analytical Letters, 37(10): 2151-2161.
  • Wardencki, W., Chmiel, T., Dymerski, T., 2013. Gas chromatography-olfactometry (GC-O), electronic noses (e-noses) and electronic tongues (e-tongues) for in vivo food flavour measurement. In: D. Kilcast (Ed.), Instrumental Assessment of Food Sensory Quality: A Practical Guide, A Volume in Woodhead Publishing Series in Food Science, Technology and Nutrition, pp. 195-229.
  • Yu, J.J., Su, J., Li, F., Gao, J.L., Li, B., Pang, M.X., Lv, G.Y., Chen, S.H., 2017. Identification and quantification of pine needle essential oil from different habitats and species of china by GC-MS and GC method. African Journal of Traditional, Complementary and Alternative Medicines, 14(6): 1-9.
  • Zhang, P., Piergiovanni, M., Franceschi, P., Mattivi, F., Vrhovsek, U., Carlin, S., 2023. Application of comprehensive 2D gas chromatography coupled with mass spectrometry in beer and wine VOC analysis. Analytica, 4(3): 347-373.
There are 26 citations in total.

Details

Primary Language English
Subjects Enzymes, Agricultural Biotechnology Diagnostics
Journal Section Research Article
Authors

Nurten Yılmaz 0000-0003-3867-509X

Mustafa Oğuzhan Kaya 0000-0002-8592-1567

Elif Coşkun Dağgeçen 0000-0003-4688-5855

Publication Date March 28, 2025
Submission Date January 31, 2025
Acceptance Date March 23, 2025
Published in Issue Year 2025

Cite

APA Yılmaz, N., Kaya, M. O., & Coşkun Dağgeçen, E. (2025). Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS. Türkiye Tarımsal Araştırmalar Dergisi, 12(1), 63-71. https://doi.org/10.19159/tutad.1630871
AMA Yılmaz N, Kaya MO, Coşkun Dağgeçen E. Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS. TÜTAD. March 2025;12(1):63-71. doi:10.19159/tutad.1630871
Chicago Yılmaz, Nurten, Mustafa Oğuzhan Kaya, and Elif Coşkun Dağgeçen. “Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS”. Türkiye Tarımsal Araştırmalar Dergisi 12, no. 1 (March 2025): 63-71. https://doi.org/10.19159/tutad.1630871.
EndNote Yılmaz N, Kaya MO, Coşkun Dağgeçen E (March 1, 2025) Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS. Türkiye Tarımsal Araştırmalar Dergisi 12 1 63–71.
IEEE N. Yılmaz, M. O. Kaya, and E. Coşkun Dağgeçen, “Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS”, TÜTAD, vol. 12, no. 1, pp. 63–71, 2025, doi: 10.19159/tutad.1630871.
ISNAD Yılmaz, Nurten et al. “Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS”. Türkiye Tarımsal Araştırmalar Dergisi 12/1 (March 2025), 63-71. https://doi.org/10.19159/tutad.1630871.
JAMA Yılmaz N, Kaya MO, Coşkun Dağgeçen E. Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS. TÜTAD. 2025;12:63–71.
MLA Yılmaz, Nurten et al. “Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS”. Türkiye Tarımsal Araştırmalar Dergisi, vol. 12, no. 1, 2025, pp. 63-71, doi:10.19159/tutad.1630871.
Vancouver Yılmaz N, Kaya MO, Coşkun Dağgeçen E. Comparative Analysis of Bioactive Compounds in Pine Resin: Headspace/GC-MS and Direct Injection/GC-MS. TÜTAD. 2025;12(1):63-71.

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