Investigations on the chemical composition of volatile oils extracted from the leaves of spontaneous and cultivated Taxus baccata L. trees
DOI:
https://doi.org/10.15835/nbha51413383Keywords:
GC/MS, hexahydrofarnesyl acetone, hydrosol, Taxus, volatile oilsAbstract
Taxus L. is accepted in the literature as natural resources of biologically active compounds and volatile oils, with applications in medicine, pharmaceuticals, food, cosmetics, and with ecological impact on the natural living environment. In this context, the present work aims to analyze by GS/MS techniques the chemical composition of volatile oil obtained by hydrodistillation of leaves harvested from spontaneous and cultivated female individuals of Taxus (dried and fresh plant material) and to spectrophotometrically evaluate the hydrosols resulting from their hydrodistillation. The compounds with the highest concentrations in the volatile oil obtained from the spontaneous taxon Taxus baccata L. were hexahydrofarnesyl acetone (33.03% fresh leaves; 20.09% dried leaves); ar-abietatriene (14.98% dried leaves; 3.03% fresh leaves); phthalic acid, hex-3-yl isobutyl ester (10.51% dried leaves); salicylic acid, benzyl ester (8.11% dried leaves). In the cultivated taxon Taxus baccata the compounds identified with the highest concentrations were 1-octen-3-ol (25.61% fresh leaves); phytol (12.50% dry leaves); geranyl acetone (11.90% dry leaves); manoyl oxide (11.85% dry leaves; 10.86% fresh leaves); 1,9-decadence (7.92% fresh leaves). The compounds with the highest concentrations in the oil extracted from the leaves of Taxus baccata ‘Robusta’ were hexahydrofarnesyl acetone (17.81% fresh leaves); pentacosane (11.28% dry leaves); heptacosane (11.27% fresh leaves); tetracosane (11.13% dry leaves); tricosane (8.45% fresh leaves). The chemical composition of volatile oils from yew is influenced by many exogenous factors such as soil, light, and endogenous factors such as age, DNA.
References
Ansari M, Emami S (2016). b-Ionone and its analogs as promising anticancer agents. European Journal of Medicinal Chemistry 1231:141-154. http://dx.doi.org/10.1016/j.ejmech.2016.07.037
Azhar MA, Rahaman NWA, Aziz MAA, Isa KM (2021). Identification of chemical compounds from agarwood hydrosol (Aquilaria malaccensis) fruits via LC-QTOF-MS/MS analysis, Earth and Environmental Science 765(012010):1-16. https://doi.org/10.1088/1755-1315/765/1/012010
Azmir J, Zaidul ISM, Rahman MM, Sharif KM, Mohamed A, Sahena F, Jahurul MHA, Ghafoor K, Norulaini NAN, Omar AKM (2013). Techniques for extraction of bioactive compounds from plant materials: A review. Journal of Food Engineering 117:426-436. https://doi.org/10.1016/j.jfoodeng.2013.01.014
Baciu A, Ranga F, Fetea F, Zavoi S, Socaciu C (2013). Fingerprinting Food supplements and their botanical ingredients by coupled UV/Vis/FTIR spectrometry. Bulletin UASVM Food Science and Technology 70(1):8-15.
Bajpai VK, Sharma A, Moon B, Baek KH (2013). Chemical composition analysis and antibacterial mode of action of Taxus cuspidata leaf essential oil against foodborne pathogens. Journal of Food Safety 1745-4565. https://doi.org/10.1111/jfs.12089
Bakkali F, Averbeck S, Averbeck D, Idaomar M (2008). Biological effects of essential oils-a review. Food and Chemical Toxicology 46:446-475. https://doi.org/10.1016/j.fct.2007.09.106
Barra A (2009). Factors affecting chemical variability of essential oils: a review of recent developments. Natural product communications 4(8):1147-1154. https://doi.org/10.1177/1934578X0900400827
Benlembarek K, Lograda T, Ramdani M, Figueredo G, Chalard P (2021). Chemical composition, antibacterial, antifungal, and antioxidant activities of Taxus baccata essential oil from Algeria. Biodiversitas 22(12):5475-5483. https://doi.org/10.13057/biodiv/d221231
Bhardwaj K, Islam MT, Jayasena V, Sharma B, Sharma S, Sharma P, Kuca K, Bhardwaj P (2020). Review on essential oils, chemical composition, extraction, and utilization of some conifers in Northwestern Himalayas. Phytotherapy Research 1-22. https://doi.org/10.1002/ptr.6736
Bîrsan C, Mardari C, Copoț O, Apăștinei L (2017). Development of Taxus baccata L. population under tree canopy in the Tudora Reservation. Acta Oecologica Carpatica 11:37-50.
Burzo I, Toma C (2012). Ţesuturile secretoare şi substanţe volatile din plante [Secretory tissues and volatile substances in plants]. Ed. Universităţii „Alexandru Ioan Cuza” din Iaşi, pp 148.
Butnariu M (2014). Detection of the polyphenolic components in Ribes nigrum L. Annals of Agricultural and Environmental Medicine 21(1):11-14.
Chen H, Yuan J, Hao J, Wen Y, Lv Y, Chen L, Yang X (2019). α-Humulene inhibits hepatocellular carcinoma cell proliferation and induces apoptosis through the inhibition of Akt signaling, Food and Chemical Toxicology 134:1-11. https://doi.org/10.1016/j.fct.2019.110830
Cordeiro L, Figueiredo P, Souza H, Sousa A, Júnior FA, Filho JB, Lima E (2020). Antibacterial and antibiofilm activity of myrtenol against Staphylococcus aureus. Pharmaceuticals 13(6):133. https://doi.org/10.3390/ph13060133
D’Amato S, Serio A, López CC, Paparella A (2018). Hydrosols biological activity and potential as antimicrobials for food application. Food Control 86:126-137. https://doi.org/10.1016/j.foodcont.2017.10.030
Dhakal S, Khosla PK, Getahun T (2022). Chemical compositions and biological activities of the oils from the genus Taxus and factors limiting the regeneration of endangered yews: a review. Turkish Journal of Chemistry 46(6):1776-1801. https://doi.org/10.55730/1300-0527.3480
Dhifi W, Bellili S, Jazi S, Bahloul N, Mnif W (2016). Essential oils’ chemical characterization and investigation of some biological activities: a critical review. Medicines 3(4):25. https://doi.org/10.3390/medicines3040025
ElGawad AMA, Gendy AENGE, Assaeed AM, Rowaily SLA, Alharthi AS, Mohamed TA, Nassar MI, Dewir YH, Elshamy AI (2021). Phytotoxic effects of plant essential oils: a systematic review and structure-activity relationship based on chemometric analyses. Plants 10(1):36. https://dx.doi.org/10.3390/plants10010036
Erdemoglu N, Sener B, Demirci B, Baser KHC (2003). The glycosidically bound volatile compounds of Taxus baccata. Chemistry of Natural Compounds 39(2):195-198.
Ferhat MA, Meklati BY, Smadja J, Chemat F (2006). An improved microwave Clevenger apparatus for distillation of essential oils from orange peel. Journal of Chromatography A 1112:121-126. https://doi.org/10.1016/j.chroma.2005.12.030
Figueiredo AC, Barroso JG, Pedro LG, Scheffer JJC (2008). Factors affecting secondary metabolite production in plants: volatile components and essential oils. Flavour and Fragrance Journal 23:213-226. https://doi.org/10.1002/ffj.1875
Gherman Ghe (2007). Vorniceni însemnată vatră strămoșească [Vorniceni, a significant ancestral home]. Ed. Agata pp 9-44.
Guan C, Liu W, Yue Y, Jin H, Wang X, Wang XJ (2014). Inhibitory effect of β-elemene on human breast cancer cells. International Journal of Clinical & Experimental Pathology 7(7):3948-3956.
Huong LT, Thuong NTH, Chac LD, Dai DN, Ogunwande IA (2020). Antimicrobial activity and chemical constituents of essential oils from the leaf and wood of Taxus chinensis (Rehder & E.H. Wilson) Rehder (Taxaceae) from Vietnam. Journal of Biologically Active Products from Nature 10(1):8-17. https://doi.org/10.1080/22311866.2020.1749128
Huong LT, Thuong TH, Chac LD, Dai DN, Ajeniya AOG, Ogunwande IA (2020). The stem essential oil of Taxus chinensis (Rehder & E.H. Wilson) Rehder (Taxaceae) from Vietnam. American Journal of Essential Oils and Natural Products 8(3):09-12.
Inouye S, Takahashi M, Abe S (2008). A comparative study on the composition of forty-four hydrosols and their essential oils. International Journal of Essential Oil Therapeutics 2:89-104.
Jean FI, Garneau FX, Collin GJ, Bouhajib M, Zamir LO (1993). The essential oil and glycosidically bound volatile compounds of Taxus canadensis Marsh. Journal of Essential Oil Research 5(1):7-11. https://doi.org/10.1080/10412905.1993.9698163
Jovanović B (1970). Taxus L. In: Josifović M (Ed). Flora of Serbia 1, SASA, Belgrade, pp 164-166.
Khan M, Verma SC, Srivastava SK, Shawl AS, Syamsundar KV, Khanuja SPS, Kumar T (2006). Essential oil composition of Taxus wallichiana Zucc. from the northern Himalayan region of India. Flavour and Fragrance Journal 21:772-775. https://doi.org/10.1002/ffj.1682
Kumar S, Abedin M, Singh AK, Das S (2020). Role of phenolic compounds in plant-defensive mechanisms. In: Lone R, Shuab R, Kamili AN (Eds). Plant phenolics in sustainable agriculture. Springer, Singapore, pp 517-532. https://doi.org/10.1007/978-981-15-4890-1.
Labbozzetta M, Poma P, Tutone M, McCubrey JA, Sajeva M, Notarbartolo M (2022). Phytol and heptacosane are possible tools to overcome multidrug resistance in an in vitro model of acute myeloid leukemia. Pharmaceuticals 15(36):1-19. https://doi.org/10.3390/ph15030356
Lefebvre T, Destandau E, Lesellier E (2020). Selective extraction of bioactive compounds from plants using recent extraction techniques: a review. Journal of Chromatography A 1-50. https://doi.org/10.1016/j.chroma.2020.461770
Legault J, Dahl W, Debiton E, Pichette, A., Madelmont JC (2003). Antitumor activity of balsam fir oil: production of reactive oxygen species induced by α-Humulene as possible mechanism of action. Planta Medica 69(5):402-407.
Milutinović MG, Stanković MS, Cvetković DM, Topuzović MD, Mihailović VB, Marković SD (2015). Antioxidant and anticancer properties of leaves and seed cones from European yew (Taxus baccata L.). Archives of Biological Sciences, Belgrade 67(2):525-534. 10.2298/ABS161021105E
Mohan Ghe, Ardelean A (2006). Parcuri și rezervații naturale din România [Natural parks and reserves in Romania]. Ed. Victor B Victor, București, pp 118-119.
Panzeri C, Bacis G, Ferri F, Rinaldi G, Persico A, Uberti F, Restani P (2010). Extracorporeal life support in a severe Taxus baccata poisoning. Clinical Toxicology 48:463-465. https://doi.org/10.3109/15563650.2010.487487
Paparella A, Harpaza LS, Ibdah M (2021). -Ionone: its occurrence and biological function and metabolic engineering. Plants 10(4):745. https://doi.org/10.3390/plants10040754
Pereira I, Severino P, Santos AC, Silva AM, Souto EB (2018). Linalool bioactive properties and potential applicability in drug delivery systems. Colloids and Surfaces B: Biointerfaces 171:566-578. https://doi.org/10.1016/j.colsurfb.2018.08.001
Politi M, Ferrante C, Menghini L, Angelini P, Flores GA, Muscatello B, Braca A, De Leo M (2022). Hydrosols from Rosmarinus officinalis, Salvia officinalis, and Cupressus sempervirens: Phytochemical analysis and bioactivity evaluation. Plants 11(3):349. https://doi.org/10.3390/plants11030349
Pretsch E, Bühlmann P, Badertscher M (2009). Structure determination of organic compounds, Tables of spectral data, Springer -Verlag Berlin Heidelberg.
Radulović N, Blagojević P, Palić R, Zlatković B (2010). Chemical composition of the essential oil hydrodistilled from Serbian Taxus baccata L. Journal of Essential Oil Research 22(5):458-461. https://doi.org/10.1080/10412905.2010.9700371
Rajeswara Rao, BR (2013). Hydrosols and water-soluble essential oils: medicinal and biological properties. Recent progress in medicinal plants. Essential oils I 36:119-140.
Reijnen G, Bethlehem C, Remmen JMBL, Smit HJM, Luin M, Reijnders UJL (2017). Post-mortem findings in 22 fatal Taxus baccata intoxications and a possible solution to its detection. Journal of Forensic and Legal Medicine 52:56-61. http://dx.doi.org/10.1016/j.jflm.2017.08.016
Robakowski P, Pers-Kamczyc E, Ratajczak E, Thomas PA, Ye ZP, Rabska M, Iszkulo G (2018). Photochemestry and antioxidative capacity of female and male Taxus baccata L. acclimated to different nutritional Environments. Frontiers in Plant Science 9:742. https://doi.org/10.3389/fpls.2018.00742.
Sadgrove NJ, Gonzalez GFP, Leuner O, Melnikovova I, Cusimamani EF (2021). Pharmacology of natural volatiles and essential oils in food, therapy, and disease prophylaxis. Frontiers in Pharmacology 1-16. https://doi.org/10.3389/fphar.2021.740302
Sharma A, Sharma A, Thakur S, Mutreja V, Bhardwaj G (2022). A brief review on phytochemistry and pharmacology of Taxus baccata L. Materials Today: Proceedings 48:1569-1574. https://doi.org/10.1016/j.matpr.2021.09.468
Shirmohammadli Y, Hosseinihashemi SK, Jalaligoldeh A, Efhamisisi D, Mousavinezhad SH, Lashgari A (2020). Chemical composition of Taxus baccata L. leaves and male cones water: methanol extracts. Celal Bayar University Journal of Science 16(3): 251-255. https://doi.org/10.18466/cbayarfbe.689482
Stefanović M, Ristić M, Popović Z, Matić R, Nikolić B, Vidaković V, Petković DO, Bojović S (2016). Chemical composition and interpopulation variability of essential oils of Taxus baccata L. from Serbia. Chemistry & Biodiversity 1-36. https://doi.org/10.1002/cbdv.201500326
Stevanović ZD, Neumüller JB, Lijaković IP, Raj J, Vasiljević M (2018). Essential oils as feed additives—Future Perspectives. Molecules 23:1717. https://doi.org/10.3390/molecules23071717
Timung R, Purohit S, Barik CR, Goud V (2016). Composition and anti-bacterial activity analysis, Industrial Crops and Products 94:178-188. http://dx.doi.org/10.1016/j.indcrop.2016.08.021
Turek C, Stintzing F (2013). Stability of essential oils: a review. Comprehensive Reviews in Food Science and Food Safety 12:40-53. https://doi.org/10.1111/1541-4337.12006
Ulusoy S, Tınaz GB, Canbay HS (2009). Tocopherol, carotene, phenolic contents and antibacterial properties of rose essential oil, hydrosol and absolute. Current Microbiology 59:554-558. https://doi.org/10.1007/s00284-009-9475-y
Wang T, Lingyu L, Qin Y, Lu B, Xu D, Zhuang W, Shu X, Zhang F, Wang N, Wang Z (2023). Effects of seasonal changes on chlorophyll fluorescence and physiological characteristics in the two Taxus species. Plants 12(2636):11-17. https://doi.org/10.3390/plants12142636
Wangkheirakpam SD, Laitonjam WS (2016). Studies on the uses of some plants for medicinal and dyeing properties. International Journal of Chemistry 5(1):93-102.
Wei Q, Yin CW (2019). Chemical Composition of Essential Oils from the Stems of Taxus chinensis var. mairei. Journal of Essential Oil-Bearing Plants 22(4):1144-1149. https://doi.org/10.1080/0972060X.2019.1668864
Zhang J, Yuan K, Jin Y (2012). Comparison of chemical composition and antimicrobial activities of the essential oil of Taxus media and Taxus chinensis var. mairei leaves, Advanced Materials Research 343-344:1092-1097. https://doi.org/10.4028/www.scientific.net/AMR.343-344.1092
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Copyright (c) 2023 Mădălina-Elena FRUNZETE, Tatiana RODIDEAL, Marius-Nicușor GRIGORE, Violeta A. ION, Liliana BĂDULESCU, Ramona M. CIOCAN, Maria-Magdalena ZAMFIRACHE
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