biologia plantarum

International journal on Plant Life established by Bohumil Němec in 1959

Biologia plantarum 68:97-106, 2024 | DOI: 10.32615/bp.2024.011

Metabolites profiling of five Eucalyptus species by gas chromatography-mass spectrometry and multivariate analysis

Alyaa NASR1, 2, Ming-Jie BIAN1, Xue-Fei CHEN1, Bin WEN1, Hui WANG1, Jian-Wen SHAO1, Guo-Ping ZHU1, *
1 Anhui Provincial Key Laboratory of Molecular Enzymology and Mechanism of Major Metabolic Diseases, College of Life Sciences, Anhui Normal University, Wuhu 241000, Anhui, China
2 Botany and Microbiology Department, Faculty of Science, Menoufia University, Shebin Elkoom 32511, Menoufia, Egypt

An untargeted metabolomic analysis of five Eucalyptus species was used to compare their chemical profiles. Gas chromatography-mass spectrometry (GC-MS) along with multivariate analyses including principal component analysis (PCA) and hierarchical cluster analysis (HCA) were applied to assess variations in the leaf chemical profiles of E. maidenii F. Muell, E. robusta Smith, E. citriodora Hook (syn Corymbia citriodora), E. tereticornis Smith and E. camaldulensis Dehnh. In total, 299 relevant metabolites were identified and subjected to statistical analyses in order to detect either the major common metabolites of the genus or the specific compounds contributing to the characteristic chemical composition of each species. Organic acids, nitrogenous compounds, and phenolic constituents were the main discriminatory groups between the investigated eucalypts. The cluster analysis revealed that fatty acids and fatty alcohols were more concentrated in the leaves of E. citriodora and distinguished it from other species, whereas sugars, polyols, and glycosides were characteristic to E. camaldulensis.

Keywords: Eucalyptus, gas chromatography-mass spectrometry, hierarchical cluster, metabolite profiling, multivariate analysis, principal component analysis.

Received: February 27, 2024; Revised: June 4, 2024; Accepted: June 18, 2024; Published online: July 10, 2024  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
NASR, A., BIAN, M., CHEN, X., WEN, B., WANG, H., SHAO, J., & ZHU, G. (2024). Metabolites profiling of five Eucalyptus species by gas chromatography-mass spectrometry and multivariate analysis. Biologia plantarum, 68, Article 97-106. https://doi.org/10.32615/bp.2024.011
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    Supplementary files

    Download file7142_Nasr_Suppl.pdf

    File size: 202.54 kB

    References

    1. Agunloye, O.M. & Oboh, G. (2018) Caffeic acid and chlorogenic acid: Evaluation of antioxidant effect and inhibition of key enzymes linked with hypertension. Journal of Food Biochemistry, 42, e12541. Go to original source...
    2. Al-Malki, A.L. (2019) Shikimic acid from Artemisia absinthium inhibits protein glycation in diabetic rats. International Journal of Biological Macromolecules, 122, 1212-1216. Go to original source...
    3. Amaefule, C.E., Drymoussi, Z., Dodds, J. et al. (2018) Effectiveness and acceptability of myo-inositol nutritional supplement in the prevention of gestational diabetes (EMmY): a protocol for a randomised, placebo-controlled, doubleblind pilot trial. BMJ Open, 8, e022831. Go to original source...
    4. Bai, J.-R., Wu, Y.-P., Elena, G., Zhong, K. & Gao H. (2019) Insight into the effect of quinic acid on biofilm formed by Staphylococcus aureus. RSC Advances, 9, 3938-3945. Go to original source...
    5. Becker, L.C., Akinsulie, A., Bergfeld, W.F. et al. (2023) Safety assessment of Eucalyptus globulus (Eucalyptus)-derived ingredients as used in cosmetics. International Journal of Toxicology, 42, 57S-92S. Go to original source...
    6. Ben Ghnaya, A., Hamrouni, L., Amri, I., Ahoues, H., Hanana, M. & Romane, A. (2016) Study of allelopathic effects of Eucalyptus erythrocorys L. crude extracts against germination and seedling growth of weeds and wheat. Natural Product Research, 30, 2058-2064. Go to original source...
    7. Bhuyan, D.J., Vuong, Q.V., Chalmers, A.C., van Altena, I.A., Bowyer, M.C. & Scarlett, C.J. (2015) Microwave-assisted extraction of Eucalyptus robusta leaf for the optimal yield of total phenolic compounds. Industrial Crops and Products, 69, 290-299. Go to original source...
    8. Bhuyan, D.J., Vuong, Q.V., Chalmers, A.C., van Altena, I.A., Bowyer, M.C. & Scarlett, C.J. (2016) Investigation of phytochemicals and antioxidant capacity of selected Eucalyptus species using conventional extraction. Chemical Papers, 70, 567-575. Go to original source...
    9. Bragunde, G., Groba, H.F., Lagurara, P., Martínez, G., González, A. & Rossini, C. (2023) Correlating Eucalyptus leaf metabolomics with preference of the bronze bug, Thaumastocoris peregrinus. Journal of Chemical Ecology, 49, 482-497. Go to original source...
    10. Cevallos-Cevallos, J.M., Reyes-De-Corcuera, J.I., Etxeberria, E., Danyluk, M.D. & Rodrick, G.E. (2009) Metabolomic analysis in food science: a review. Trends in Food Science & Technology, 20, 557-566. Go to original source...
    11. Chen, S., Tan, B., Xia, Y. et al. (2018) Effects of dietary gamma-aminobutyric acid supplementation on the intestinal functions in weaning piglets. Food & Function, 10, 366-378. Go to original source...
    12. Choubey, S., Varughese, L.R., Kumar, V. & Beniwal, V. (2015) Medicinal importance of gallic acid and its ester derivatives: a patent review. Pharmaceutical Patent Analyst, 4, 305-315. Go to original source...
    13. Correia, B., Hancock, R.D., Amaral, J., Gomez-Cadenas, A., Valledor, L. & Pinto, G. (2018) Combined drought and heat activates protective responses in Eucalyptus globulus that are not activated when subjected to drought or heat stress alone. Frontiers in Plant Science, 9, 819. Go to original source...
    14. Dludla, P.V., Nkambule, B.B., Jack, B. et al. (2019) Inflammation and oxidative stress in an obese state and the protective effects of gallic acid. Nutrients, 11, 23. Go to original source...
    15. Elangovan, S. & Mudgil, P. (2023) Antibacterial properties of Eucalyptus globulus essential oil against MRSA: a systematic review. Antibiotics, 12, 474. Go to original source...
    16. Fraire-Velázquez, S. & Balderas-Hernández, V.E. (2013) Abiotic stress in plants and metabolic responses. In: Vahdati, K. & Leslie, C. (Eds.) Abiotic Stress: Plant Responses and Applications in Agriculture. London: IntechOpen, pp. 25-48. Go to original source...
    17. Howlett, A., Ohlsson, A. & Plakkal, N. (2019) Inositol in preterm infants at risk for or having respiratory distress syndrome. Cochrane Database of Systematic Reviews, 2019, CD000366. Go to original source...
    18. Huang, H., Ho, Y., Lim, J., Chang, T., Ho, C. & Chang, T. (2015) Investigation of the anti-melanogenic and antioxidant characteristics of Eucalyptus camaldulensis flower essential oil and determination of its chemical composition. International Journal of Molecular Sciences, 16, 10470-10490. Go to original source...
    19. Jaroszyńska, J. (2003) The influence of solvent choice on the recovery of phytogenic phenolic compounds extracted from plant material. Polish Journal of Environmental Studies, 12, 481-484.
    20. Jolliffe, I.T. (2002) Principal Component Analysis. 2nd edition. New York: Springer, pp. 488.
    21. Khan, R.A., Khan, M.R., Sahreen, S. & Ahmed, M. (2012) Assessment of flavonoids contents and in vitro antioxidant activity of Launaea procumbens. Chemistry Central Journal, 6, 43. Go to original source...
    22. Kim, H.K., Choi, Y.H. & Verpoorte, R. (2011) NMR-based plant metabolomics: Where do we stand, where do we go? Trends in Biotechnology, 29, 267-275. Go to original source...
    23. Kim, M.J., Sim, D.Y., Lee, H.M., Lee, H.J. & Kim, S.H. (2019) Hypolipogenic effect of shikimic acid via inhibition of MID1IP1 and phosphorylation of AMPK/ACC. International Journal of Molecular Sciences, 20, 582. Go to original source...
    24. Kołodziejczyk, K., Sójka, M., Abadias, M., Viñas, I., Guyot, S. & Baron, A. (2013) Polyphenol composition, antioxidant capacity, and antimicrobial activity of the extracts obtained from industrial sour cherry pomace. Industral Crops and Products, 51, 279-288. Go to original source...
    25. Kosuru, R.Y., Roy, A., Das, S.K. & Bera, S. (2018) Gallic acid and gallates in human health and disease: Do mitochondria hold the key to success? Molecular Nutrition & Food Research, 62, 1700699. Go to original source...
    26. Lavergne, F.D., Broeckling, C.D., Cockrell, D.M. et al. (2018) GC-MS metabolomics to evaluate the composition of plant cuticular waxes for four Triticum aestivum cultivars. International Journal of Molecular Sciences, 19, 249. Go to original source...
    27. Lazar, A.G., Romanciuc, F., Socaciu, M.A. & Socaciu, C. (2015) Bioinformatics tools for metabolomic data processing and analysis using untargeted liquid chromatography coupled with mass spectrometry. Bulletin UASVM Animal Science Biotechnologies, 72, 103-115. Go to original source...
    28. Lou, S.-N., Lai, Y.-C., Hsu, Y.-S. & Ho, C.-T. (2016) Phenolic content, antioxidant activity and effective compounds of kumquat extracted by different solvents. Food Chemistry, 197, 1-6. Go to original source...
    29. Merchant, A., Richter, A., Popp, M. & Adams, M. (2006a) Targeted metabolic profiling provides a functional link among eucalypt taxonomy, physiology and evolution. Phytochemistry, 67, 403-408. Go to original source...
    30. Merchant, A., Tausz, M., Arndt, S.K. & Adams, M.A. (2006b) Cyclitols and carbohydrates in leaves and roots of 13 Eucalyptus species suggest contrasting physiological responses to water deficit. Plant Cell Environment, 29, 2017-2029. Go to original source...
    31. Mokochinski, J.B., Mazzafera, P., Sawaya, A.C.H.F., Mumm, R., de Vos, R.C.H. & Hall, R.D. (2018) Metabolic responses of Eucalyptus species to different temperature regimes. Journal of Integrated Plant Biology, 60, 397-411. Go to original source...
    32. Mubarak, E.E., Ali, L.Z., Ahmed, I.F.A., Ahmed A.B.A. & Taba R.M. (2015) Essential oil compositions and cytotoxicity from various organs of Eucalyptus camaldulensis. International Journal of Agriculture & Biology, 17, 320-326.
    33. Nasr, A., Khan, T.S. & Zhu, G.P. (2019b) Phenolic compounds and antioxidants from Eucalyptus camaldulensis as affected by some extraction conditions, a preparative optimization for GC-MS analysis. Preparative Biochemistry & Biotechnology, 49, 464-476. Go to original source...
    34. Nasr, A., Zhou, X., Huang, S.P., Wang, Y., Li, X. & Zhu, G.P. (2019a) Comparative effects of some extraction solvents on the antimicrobial activity of Eucalyptus camaldulensis leaf, bud, capsule and seed crude extracts. Natural Product Research, 33, 2560-2565. Go to original source...
    35. Nayeem, N., SMB, A., Salem, H. & AHEl-Alfqy, S. (2016) Gallic acid: A promising lead molecule for drug development. Journal of Applied Pharmacy, 8, 213. Go to original source...
    36. Otto, M.S.G., Francisco, J.G., Gonsalez, B.T. et al. (2017) Changes in γ-aminobutyric acid concentration, gas exchange, and leaf anatomy in Eucalyptus clones under drought stress and rewatering. Acta Physiologiae Plantarum, 39, 208. Go to original source...
    37. Pimenta, A.S., Fasciotti, M., Monteiro, T.V.C. & Lima, K.M.G. (2018) Chemical composition of pyroligneous acid obtained from Eucalyptus GG100 clone. Molecules, 23, 426. Go to original source...
    38. Rabelo, T.K., Guimarães, A.G., Oliveira, M.A. et al. (2016) Shikimic acid inhibits LPS-induced cellular pro-inflammatory cytokines and attenuates mechanical hyperalgesia in mice. International Immunopharmacology, 39, 97-105. Go to original source...
    39. Rajapaksha, C., Greaves, P. & Altaner, C.M. (2023) Economic potential of essential oil production from New Zealand-grown Eucalyptus bosistoana. Scientific Reports, 13, 14083. Go to original source...
    40. Regidor, P.-A., Schindler, A.E., Lesoine, B. & Druckman, R. (2018) Management of women with PCOS using myo-inositol and folic acid. New clinical data and review of the literature. Hormone Molecular Biology and Clinical Investigation, 34, 20170067. Go to original source...
    41. Rodrigues, V.H., de Melo, M.M.R., Portugal, I. &Silva, C.M. (2018) Extraction of Eucalyptus leaves using solvents of distinct polarity. Cluster analysis and extracts characterization. The Journal of Supercritical Fluids, 135, 263-274. Go to original source...
    42. Sastya, S., Kumar, R.R. & Vatsya, S. (2018) In vitro and in-vivo efficacy of Eucalyptus citriodora leaf in gastrointestinal nematodes of goats. Journal of Entomology and Zoology Studies, 6, 25-30. Go to original source...
    43. Sebei, K., Sakouhi, F., Herchi, W., Khouja, M.L. & Boukhchina, S. (2015) Chemical composition and antibacterial activities of seven Eucalyptus species essential oils leaves. Biological Research, 48, 7. Go to original source...
    44. Sharma, V., Ankita, Karnwal, A. et al. (2023) A comprehensive review uncovering the challenges and advancements in the in vitro propagation of Eucalyptus plantations. Plants, 12, 3018. Go to original source...
    45. Souza, J.G.S., Cordeiro, J.M., Lima, C.V. & Barão, V.A.R. (2019) Citric acid reduces oral biofilm and influences the electrochemical behavior of titanium: An in situ and in vitro study. Journal of Periodontology, 90, 149-158. Go to original source...
    46. Talhaoui, N., Gómez-Caravaca, A.M., Roldán, C. et al. (2015) Chemometric analysis for the evaluation of phenolic patterns in olive leaves from six cultivars at different growth stages. Journal of Agricultural and Food Chemistry, 63, 1722-1729. Go to original source...
    47. Taylor, M.J., Wilder, H., Bhagwagar, Z. & Geddes, J. (2004) Inositol for depressive disorders. Cochrane Database of Systematic Reviews, 2004, CD004049. Go to original source...
    48. Tugizimana, F., Piater, L. & Dubery, I. (2013) Plant metabolomics: A new frontier in phytochemical analysis. South African Journal of Science, 109, 11. Go to original source...
    49. Veach, D., Hosking, H., Thompson, K. & Santhakumar, A.B. (2016) Anti-platelet and anti-thrombogenic effects of shikimic acid in sedentary population. Food & Function, 7, 3609-3616. Go to original source...
    50. Vuong, V.Q., Chalmers, A.C., Bhuyan, D.J., Bowyer, M.C. & Scarlett, C.J. (2015) Botanical, phytochemical, and anticancer properties of the Eucalyptus species. Chemistry & Biodiversity, 12, 907-924. Go to original source...
    51. Warren C.R., Aranda I. & Cano F.J. (2012) Metabolomics demonstrates divergent responses of two Eucalyptus species to water stress. Metabolomics, 8, 186-200. Go to original source...
    52. Wong, Y.F., Perlmutter, P. & Marriott, P.J. (2017) Untargeted metabolic profiling of Eucalyptus spp. leaf oils using comprehensive two-dimensional gas chromatography with high resolution mass spectrometry: Expanding the metabolic coverage. Metabolomics, 13, 46. Go to original source...
    53. Zhang, T., Wei, X., Miao, Z., Hassan, H., Song, Y. & Fan, M. (2016) Screening for antioxidant and antibacterial activities of phenolics from Golden Delicious apple pomace. Chemistry Central Journal, 10, 47. Go to original source...

    Return to the content