Abstract
Background: Eucalyptus belongs to the Myrtaceae family. It is the most planted hardwood forest crop worldwide, representing a global renewable resource of fiber, pharmaceuticals and energy.
Objective: To compare the five species, E. maidenii, E. robusta, E. citriodora, E. tereticornis and E. camaldulensis, seeking for the richest source of nutrients and pharmaceuticals.
Methodology: Eucalyptus samples were subjected to some chemical determinations for both primary and secondary metabolites to verify their nutritional and pharmaceutical importance related to different extracts. GC-MS analysis was applied to detect the presence of some individual phenolic constituents in their leaves.
Results: E. robusta recorded the maximum contents of carbohydrates (40.07%) and protein (31.91%). While E. camaldulensis contained the highest contents of total phenolic compounds (46.56 mg/g), tannins (40.01 mg/g) and antioxidant activities assayed by the phosphomolybednum method (57.60 mg/g), followed by E. citridora. However, E. tereticornis exhibited the highest reducing power ability (151.23 mg/g). The GC-MS highlighted 20 phenolic constituents and antioxidants which varied in their abundance in Eucalyptus leaves, 8 individual phenolics (hydroquinone, hesperitin, pyrogallol, resorcinol, protocatechuic acid, naringenin, chlorogenic acid and catechin) were maximally recorded with E. camaldulensis and secondly, with E. citridora in case of at least 5 components. Nevertheless, gallic and quinic acids were more abundant in the leaves of E. tereticornis, which may explain its high corresponding reducing powers.
Conclusion: Acetone-water combination has enhanced phenolics extraction from Eucalyptus tissues. This is the first report aiming to compare between the aforementioned Eucalyptus species highlighting either their nutritional or medicinal importance.
Keywords: Eucalyptus, carbohydrates, protein, phenolic compounds, antioxidants, GC-MS.
Graphical Abstract
[1]
Leicach, S.R.; Grass, M.A.Y.; Chludil, H.D.; Garau, A.M.; Guarnaschelli, A.B.; Fernandez, P.C. 2012, Chemical Defenses in Eucalyptus
Species: A Sustainable Strategy Based on Antique Knowledge
to Diminish Agrochemical Dependency, New Advances and
Contributions to Forestry Research, Dr. Dr. Andrew A. OtengAmoako
(Ed.), ISBN: 978-953-51-0529-9. InTech,, 2012, 14, 225-
256.
[2]
Ohra-aho, T.; Gomes, F.J.B.; Colodette, J.L.; Tamminen, T. Carbohydrate composition in Eucalyptus wood and pulps – comparison between Py-GC/MS and acid hydrolysis. J. Anal. Appl. Pyrolysis, 2018, 129, 215-220. [http://dx.doi.org/10.1016/j.jaap.2017.11.010].
[3]
Khattab, H.; Khattab, I. Responses of eucalypt trees to the insect feeding (Gall-Forming Psyllid). Int. J. Agric. Biol., 2005, 7, 979-984.
[4]
Boulekbache-Makhlouf, L.; Meudec, E.; Mazauric, J.P.; Madani, K.; Cheynier, V. Qualitative and semi-quantitative analysis of phenolics in Eucalyptus globulus leaves by high-performance liquid chromatography coupled with diode array detection and electrospray ionisation mass spectrometry. Phytochem. Anal., 2013, 24(2), 162-170. [http://dx.doi.org/10.1002/pca.2396]. [PMID: 22930658].
[5]
Cheynier, V.; Comte, G.; Davies, K.M.; Lattanzio, V.; Martens, S. Plant phenolics: Recent advances on their biosynthesis, genetics, and ecophysiology. Plant Physiol. Biochem., 2013, 72, 1-20. [http://dx.doi.org/10.1016/j.plaphy.2013.05.009]. [PMID: 23774057].
[6]
Gharekhani, M.; Ghorbani, M.; Rasoulnejad, N. Microwave-assistedextraction of phenolic and flavonoid compounds from Eucalyptus camaldulensis Dehn leaves as compared with ultrasound-assisted extraction. Lat. Am. Appl. Res., 2012, 42, 305-310.
[7]
Gutmann, A.; Bungaruang, L.; Weber, H.; Leypold, M.; Breinbauer, R.; Nidetzky, B. Towards the synthesis of glycosylated dihydrochalcone natural products using glycosyltransferase catalysed cascade reactions. Green Chem., 2014, 16, 4417-4425. [http://dx.doi.org/10.1039/C4GC00960F].
[8]
Takahashi, T.; Kokubo, R.; Sakaino, M. Antimicrobial activities of eucalyptus leaf extracts and flavonoids from Eucalyptus maculata. Lett. Appl. Microbiol., 2004, 39(1), 60-64. [http://dx.doi.org/10.1111/j.1472-765X.2004.01538.x]. [PMID: 15189289].
[9]
Pengelly, A. Eucalyptus-herbal medicine and essential oil: Non-volatile constituents. Aroma Ther. Today, 2018, 71, 8-11.
[10]
Miguel, M.G.; Gago, C.; Antunes, M.D.; Lagoas, S.; Faleiro, M.L.; Megías, C.; Cortés-Giraldo, I.; Vioque, J.; Figueiredo, A.C. Antibacterial, antioxidant, and antiproliferative activities of Corymbia citriodora and the essential oils of eight Eucalyptus species. Medicines (Basel), 2018, 5(3), E61. [http://dx.doi.org/10.3390/medicines5030061]. [PMID: 29933560].
[11]
Ammer, M.R.; Zaman, S.; Khalid, M.; Bilal, M.; Erum, S.; Huang, D.; Che, S. Optimization of antibacterial activity of Eucalyptus tereticornis leaf extracts against Escherichia coli through response surface methodology. J. Rad. Res. App. Sci., 2016, 9, 376-385. [http://dx.doi.org/10.1016/j.jrras.2016.05.001].
[12]
Sastya, S.; Kumar, R.R.; Vatsya, S. In vitro and in-vivo efficacy of Eucalyptus citriodora Leaf in gastrointestinal nematodes of goats. J. Entomol. Zool. Stud., 2018, 6(5), 25-30.
[13]
Bencha, S.; Abdelkrim, M.H.H. Allelopathic effect of Eucalyptus citriodora essential oil and its potential use as bioherbicide. Chem. Biod., 2018, 15(8), e1800202. [http://dx.doi.org/10.1002/cbdv.201800202].
[14]
Muhammed, D.; Dada, E.O.; Alo, A.A. Antibacterial property of ethanolic leaf extract of Eucalyptus citriodora Hook on clinical and typed isolates of Escherichia coli. South Asian J. Res. Microbiol., 2018, 2(1), 1-8.
[15]
Üstüner, T.; Kordali, S.; Bozhüyük, A.U.; Kesdek, M. Investigation of pesticidal activities of essential oil of Eucalyptus camaldulensis Dehnh. Rec. Nat. Prod., 2018, 12(6), 557-568. [http://dx.doi.org/10.25135/rnp.64.18.02.088].
[16]
Nogueira, M.C.J.A.; De Araujo, V.A.; Vasconcelos, J.S.; Da Cruz, J.N.; Vasconcelos, J.C.S.; Prataviera, F.; Christoforo, A.L.; Lahr, F.A.R. Characterization of Eucalyptus maidenii timber for structural application: Physical and mechanical properties at two moisture conditions. South-east Eur. Forum, 2018, 9(2)Doi.org/10.15177/seefor.18-10
[17]
Vuong, Q.V.; Hirun, S.; Chuen, T.L.K.; Goldsmith, C.D.; Munro, B.; Bowyer, M.C.; Chalmers, A.C.; Sakoff, J.A.; Phillips, P.A.; Scarlett, C.J. Physicochemical, antioxidant and anti-cancer activity of a Eucalyptus robusta (Sm.) leaf aqueous extract. Ind. Crops Prod., 2015, 64, 167-174. [http://dx.doi.org/10.1016/j.indcrop.2014.10.061].
[18]
Fu, L.; Xu, B.T.; Xu, X.R.; Qin, X.S.; Gan, R.Y.; Li, H.B. Antioxidant capacities and total phenolic contents of 56 wild fruits from South China. Molecules, 2010, 15(12), 8602-8617. [http://dx.doi.org/10.3390/molecules15128602]. [PMID: 21116229].
[19]
Vuong, Q.V.; Chalmers, A.C.; Jyoti, B.D.; Bowyer, M.C.; Scarlett, C.J. Botanical, phytochemical, and anticancer properties of the Eucalyptus species, a review. Chem. Biodivers., 2015, 12(6), 907-924. [http://dx.doi.org/10.1002/cbdv.201400327]. [PMID: 26080737].
[20]
Ashraf, A.; Sarfraz, R.A.; Anwar, F.; Shahid, S.A.; Alkharfy, K.M. Chemical composition and biological activities of leaves of Ziziphus mauritiana L. native to Pakistan. Pak. J. Bot., 2015, 47, 367-376.
[21]
Bhuyan, D.J.; Vuong, Q.V.; Bond, D.R.; Chalmers, A.C.; Bowyer, M.C.; Scarlett, C.J. Eucalyptus microcorys leaf extract derived HPLC-fraction reduces the viability of MIA PaCa-2 cells by inducing apoptosis and arresting cell cycle. Biomed. Pharmacother., 2018, 105, 449-460. [http://dx.doi.org/10.1016/j.biopha.2018.05.150]. [PMID: 29879629].
[22]
Pengkumsri, N.; Chaiyasut, C.; Sivamaruthi, B.S.; Saenjum, C.; Sirilun, S.; Peerajan, S.; Sirisattha, P.S.; Chaiyasut, K.; Kesika, P. The influence of extraction methods on composition and antioxidant properties of rice bran oil. Food Sci. Technol. (Campinas), 2015, 35(3), 493-501. [http://dx.doi.org/10.1590/1678-457X.6730].
[23]
Sadasivam, S.; Manickam, A. Biochemical Methods for Agricultural Sciences; Wiley Eastern Limited: New Delhi, 1992.
[24]
Rausch, T. The estimation of micro-algal protein content and its meaning to the evaluation of algal biomass I. Comparison of methods for extracting protein. Hydrobiologia, 1981, 78, 237-251. [http://dx.doi.org/10.1007/BF00008520].
[25]
Hartree, E.F. Determination of protein: A modification of the Lowry method that gives a linear photometric response. Anal. Biochem., 1972, 48(2), 422-427. [http://dx.doi.org/10.1016/0003-2697(72)90094-2]. [PMID: 4115981].
[26]
Jindal, K.K.; Singh, R.N. Phenolic content in male and female Carica papaya: a possible physiological marker for sex identification of vegetable seedlings. Physiol. Plant., 1975, 33, 104-107. [http://dx.doi.org/10.1111/j.1399-3054.1975.tb03774.x].
[27]
Tambe, V.D.; Bhambar, S.R. Estimation of total phenol, tannin, alkaloid and flavonoid in Hibiscus tiliaceus Linn. wood extracts. Res. Rev.: J. Pharm. Phyto., 2014, 2(4), 2332-2347.
[28]
Chang, C.C.; Yang, M.H.; Wen, H.M.; Chern, J.C. Estimation of total flavonoid content in propolis by two complementary colorimetric methods. Food Drug. Anal., 2002, 10(3), 178-182.
[29]
Prieto, P.; Pineda, M.; Aguilar, M. Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Anal. Biochem., 1999, 269(2), 337-341. [http://dx.doi.org/10.1006/abio.1999.4019]. [PMID: 10222007].
[30]
Oyaizu, M. Studies on products of browning reactions: antioxidant activities of products of browning reaction prepared from glucosamine. J. Nutr., 1986, 44, 307-315.
[31]
Dewick, P.M. Medicinal Natural Products: A Biosynthetic Approach, 3rd ed; Wiley & Sons, 2009. [http://dx.doi.org/10.1002/9780470742761]
[32]
El-Moein, N.M.; Mahmoud, E.A.; Shalaby, E.A. Antioxidant
mechanism of active ingredients separated from Eucalyptus globulus.
Organic Chem. Curr. Res, 2012, 106
[33]
Coutinho, P.M.; Stam, M.; Blanc, E.; Henrissat, B. Why are there so many carbohydrate-active enzyme-related genes in plants? Trends Plant Sci., 2003, 8(12), 563-565. [http://dx.doi.org/10.1016/j.tplants.2003.10.002]. [PMID: 14659702].
[34]
Pinard, D.; Mizrachi, E.; Hefer, C.A.; Kersting, A.R.; Joubert, F.; Douglas, C.J.; Mansfield, S.D.; Myburg, A.A. Comparative analysis of plant carbohydrate active enZymes and their role in xylogenesis. BMC Genomics, 2015, 16(1), 402. [http://dx.doi.org/10.1186/s12864-015-1571-8]. [PMID: 25994181].
[35]
Wu, H.; McAlpine, C.A.; Seabrook, L.M. The dietary preferences of koalas, Phascolarctos cinereus, in southwest Queensland, Australia. Zoo Biol., 2012, 36(1), 52-58.
[36]
Wallis, I.R.; Nicolle, D.; Foley, W.J. Available and not total nitrogen in leaves explains key chemical differences between the eucalypt subgenera. For. Ecol. Manage., 2010, 260(5), 814-821. [http://dx.doi.org/10.1016/j.foreco.2010.05.040].
[37]
Jaroszyńska, J. The influence of solvent choice on the recovery of phytogenic phenolic compounds extracted from plant material. Pol. J. Environ. Stud., 2003, 12(4), 481-484.
[38]
Tugizimana, F.; Piater, L. Dubery, I. Plant metabolomics: A new frontier in phytochemical analysis. S. Afr. J. Sci., 2013, 109(5/6), 1-11. [http://dx.doi.org/10.1590/sajs.2013/20120005].
[39]
Koudoro, Y.A.; Dossa, C.P.A.; Yèhouénou, B.B.; Tchobo, F.P.; Alitonou, G.A.; Avlessi, F.; Sohounhloué, D.C.K. Phytochemistry,
antimicrobial and antiradical activities evaluation of essential oils,
ethanolic and hydroethanolic extracts of the leaves of Eucalyptus
citriodora HOOK from Benin. Sci.Study Res, 2014, 15 1), 059-
073.
[40]
Ashraf, A.; Sarfraz, R.A.; Mahmood, A.; Dina, M. Chemical composition and in vitro antioxidant and antitumor activities of Eucalyptus camaldulensis Dehn. leaves. Ind. Crops Prod., 2015, 74, 241-248. [http://dx.doi.org/10.1016/j.indcrop.2015.04.059].
[41]
Malik, B.; Sharma, N.R.; Soni, G. Influence of agro-climatic conditions on antioxidant potential of Mentha species. J. Pharm. Res., 2013, 7, 427-432. [http://dx.doi.org/10.1016/j.jopr.2013.05.014].
[42]
Proestos, C.; Komaitis, M. Analysis of naturally occurring phenolic compounds in aromatic plants by RP-HPLC coupled to diode array detector (DAD) and GC-MS after silylation. Foods, 2013, 2(1), 90-99. [http://dx.doi.org/10.3390/foods2010090]. [PMID: 28239100].
[43]
Maestri, D.M.; Nepote, V.; Lamarque, A.L.; Zygadlo, J.A. Natural products as antioxidants. Phytochemistry. Adv. Res., 2006, 105-135.
[44]
Kilulya, K.F.; Msagati, T.A.M.; Mamba, B.B.; Ngila, J.C.; Bush, T. Effect of site, species and tree size on the quantitative variation of lipophilic extractives in Eucalyptus woods used for pulping in South Africa. Ind. Crops Prod., 2014, 56, 166-174. [http://dx.doi.org/10.1016/j.indcrop.2014.02.017].
[45]
Kołodziejczyk, K.; Sójka, M.; Abadias, M.; Vióas, I.; Guyot, S.; Baron, A. Polyphenol composition, antioxidant capacity, and antimicrobial activity of the extracts obtained from industrial sour cherry pomace. Ind. Crops Prod., 2013, 51, 279-288. [http://dx.doi.org/10.1016/j.indcrop.2013.09.030].
[46]
Nasr, A.; Zhou, X.; Huang, S.P.; Wang, Y.; Li, X.; Zhu, G.P. Comparative effects of some extraction solvents on the antimicrobial activity of Eucalyptus camaldulensis leaf, bud, capsule and seed crude extracts. Nat. Prod. Res., 2018, 1-6. [http://dx.doi.org/10.1080/14786419.2018.1455049]. [PMID: 29577746].
[47]
Ghasemian, M.E. Camaldulensis extract as a preventive to the vibriosis in western white shrimp (Litopenaeus vannamei) in Bushehr Province. J Fisheries Livest Prod., 2018, 6, 268. [http://dx.doi.org/10.4172/2332-2608.1000268].
[48]
Vázquez, G.; Santos, J.; Freire, M.S.; Antorrena, G.; González-Álvarez, J. Extraction of antioxidants from eucalyptus (Eucalyptus globulus) bark. Wood Sci. Technol., 2012, 46, 443-457. [http://dx.doi.org/10.1007/s00226-011-0418-y].
[49]
Jadhav, V.; Deshmukh, S.; Mahadkar, S. Evaluation of antioxidant potential of Clitoria ternatea L. Int. J. Pharma Sci., 2013, 5, 595-599.
[50]
Santos, S.A.O.; Vilela, C.; Domingues, R.M.A.; Oliveira, C.S.D.; Villaverde, J.J.; Freire, C.S.R.; Neto, C.P.; Silvestre, A.J.D. Secondary metabolites from Eucalyptus grandis wood cultivated in Portugal, Brazil and South Africa. Ind. Crops Prod., 2017, 95, 357-364. [http://dx.doi.org/10.1016/j.indcrop.2016.10.044].
[51]
Singab, A.N.; Ayoub, N.; Al-Sayed, E.; Martiskainen, O.; Sinkkonen, J.; Pihlaja, K. Phenolic constituents of Eucalyptus camaldulensis Dehnh, with potential antioxidant and cytotoxic activities. Rec. Nat. Prod., 2011, 5(4), 271-280.
[52]
Lee, S.W.; Hung, W.J.; Chen, Z.T. A new flavonol from the kino of Eucalyptus citriodora. Nat. Prod. Res., 2017, 31(1), 37-42. [http://dx.doi.org/10.1080/14786419.2016.1209667]. [PMID: 27426624].
[53]
Hung, W.J.; Chen, Z.T.; Lee, S.W. Antioxidant and lipoxygenase inhibitory activity of the kino of Eucalyptus citriodora. Indian J. Pharm. Sci., 2018, 80(5), 955-959. [http://dx.doi.org/10.4172/pharmaceutical-sciences.1000444].
[54]
Santos, S.A.O.; Vilela, C.; Freire, C.S.R.; Neto, C.P.; Silvestre, A.J.D. Ultra-high performance liquid chromatography coupled to mass spectrometry applied to the identification of valuable phenolic compounds from Eucalyptus wood. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci., 2013, 938, 65-74. [http://dx.doi.org/10.1016/j.jchromb.2013.08.034]. [PMID: 24055752].
[55]
Boulekbache-Makhlouf, L.; Meudec, E.; Chibane, M.; Mazauric, J.P.; Cheynier, V.; Slimani, S.; Henry, M.; Madani, K. Analysis of phenolic compounds in fruit of Eucalyptus globulus cultivated in Algeria by high performance liquid chromatography-diode array detection mass spectrometry. J. Agric. Food Chem., 2010, 58, 12615-1262. [http://dx.doi.org/10.1021/jf1029509]. [PMID: 21121679].
[56]
Pero, R.W.; Lund, H.; Leanderson, T. Antioxidant metabolism induced by quinic acid. Increased urinary excretion of tryptophan and nicotinamide. Phytother. Res., 2009, 23(3), 335-346. [http://dx.doi.org/10.1002/ptr.2628]. [PMID: 18844285].
[57]
Inbathamizh, L.; Padmini, E. Quinic acid as a potent drug candidate for prostate cancer-a comparative pharmacokinetic approach. Asian J. Pharm. Clin. Res., 2013, 6(4), 106-112.
[59]
Marsh, K.B.; Boldingh, H.L.; Shilton, R.S.; Laing, W.A. Changes in quinic acid metabolism during fruit development in three kiwifruit species. Funct. Plant Biol., 2009, 36, 463-470. [http://dx.doi.org/10.1071/FP08240].
[60]
Makena, P.S.; Pierce, S.C.; Chung, K.T.; Sinclair, S.E. Comparative mutagenic effects of structurally similar flavonoids quercetin and taxifolin on tester strains Salmonella typhimurium TA102 and Escherichia coli WP-2 uvrA. Environ. Mol. Mutagen., 2009, 50(6), 451-459. [http://dx.doi.org/10.1002/em.20487]. [PMID: 19326464].
[61]
Luo, H.; Jiang, B.H.; King, S.M.; Chen, Y.C. Inhibition of cell growth and VEGF expression in ovarian cancer cells by flavonoids. Nutr. Cancer, 2008, 60(6), 800-809. [http://dx.doi.org/10.1080/01635580802100851]. [PMID: 19005980].
[62]
Hsu, Y.L.; Uen, Y.H.; Chen, Y.; Liang, H.L.; Kuo, P.L. Tricetin, a dietary flavonoid, inhibits proliferation of human breast adenocarcinoma mcf-7 cells by blocking cell cycle progression and inducing apoptosis. J. Agric. Food Chem., 2009, 57(18), 8688-8695. [http://dx.doi.org/10.1021/jf901053x]. [PMID: 19705844].
[63]
Puig, C.G.; Reigosa, M.J.; Valentão, P.; Andrade, P.B.; Pedro, N. Unravelling the bioherbicide potential of Eucalyptus globulus Labill:
biochemistry and effects of its aqueous extract. Plos One,, 2018, Doi.org/10.1371/journal.pone.0192872. [http://dx.doi.org/10.1371/journal.pone.0192872].
[64]
Ramkissoon, J.S.; Mahomoodally, M.F.; Ahmed, N.; Subratty, A.H. Relationship between total phenolic content, antioxidant potential, and antiglycation abilities of common culinary herbs and spices. J. Med. Food, 2012, 15(12), 1116-1123. [http://dx.doi.org/10.1089/jmf.2012.0113]. [PMID: 23134460].
[65]
Gomes, F.; Martins, N.; Barros, L.; Rodrigues, M.E.; Oliveira, M.B.P.P.; Henriques, M.; Ferreira, I.C.F.R. Plant phenolic extracts as an effective strategy to control Staphylococcus aureus, the dairy industry pathogen. Ind. Crops Prod., 2018, 112, 515-520. [http://dx.doi.org/10.1016/j.indcrop.2017.12.027].
Call for Papers in Thematic Issues
01 June, 2024
Artificial Intelligence in Bioinformatics
Bioinformatics is an interdisciplinary field that analyzes and explores biological data. This field combines biology and information system. Artificial Intelligence (AI) has attracted great attention as it tries to replicate human intelligence. It has become common technology for analyzing and solving complex data and problems and encompasses sub-fields of machine ...read more
Related Journals
Anti-Cancer Agents in Medicinal Chemistry
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry
Current Bioactive Compounds
Current Cancer Drug Targets
Combinatorial Chemistry & High Throughput Screening
Current Cancer Therapy Reviews
Current Diabetes Reviews
Current Drug Safety
Current Drug Targets
Current Drug Therapy
Related Books
Drug Addiction Mechanisms in the Brain
Software and Programming Tools in Pharmaceutical Research
Objective Pharmaceutics: A Comprehensive Compilation of Questions and Answers for Pharmaceutics Exam Prep
Medicinal Chemistry of Drugs Affecting Cardiovascular and Endocrine Systems
Research Methodology and Project Management in Biotechnology
Recent Progress in Pharmaceutical Nanobiotechnology: A Medical Perspective
Medicinal Plants, Phytomedicines and Traditional Herbal Remedies for Drug Discovery and Development against COVID-19
Advanced Pharmacy
Plant-derived Hepatoprotective Drugs
The Role of Chromenes in Drug Discovery and Development
Article Metrics
41
3