91
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Phytochemical analysis, antiproliferative, antibacterial, antifungal, and antiviral activities of bitter orange (Citrus aurantium) leaf essential oil

, ORCID Icon, , ORCID Icon, , , & show all
Pages 408-418 | Received 02 Sep 2023, Accepted 29 Jan 2024, Published online: 23 Feb 2024

References

  • Abderrezak M, Abaza I, Aburjai Kabouche A, Kabouche Z. 2014. Comparative compositions of essential oils of Citrus aurantium growing in different soils. J Mat Environ Sci. 5:1913–1918.
  • Abo Elgat WAA, Kordy AM, Böhm M, Cerny R, Abdel-Megeed A, Salem MZM. 2020. Eucalyptus camaldulensis, Citrus aurantium, and Citrus sinensis essential oils as antifungal activity against Aspergillus flavus, Aspergillus niger, Aspergillus terreus, and Fusarium culmorum. Process 8:1–16.
  • Adams RP. 2001. Identification of essential oil components by gas chromatography/quadrupole mass spectroscopy. Carol Stream (IL): Allured.
  • Almeida RN, Motta SC, Brito FC, Catallani B, Leite JR. 2004. Anxiolytic like effects of rose oil inhalation on the elevated plus maze test in rats. Pharmacol Biochem Behav. 77(2):361–364. doi: 10.1016/j.pbb.2003.11.004.
  • Arul S, Rajagopalan H, Ravi J, Dayalan H. 2020. Beta-caryophyllene suppresses ovarian cancer proliferation by inducing cell cycle arrest and apoptosis. Anticancer Agents Med Chem. 20(13):1530–1537. doi: 10.2174/1871520620666200227093216.
  • Astani A, Jürgen R, Schnitzler P. 2011. Screening for antiviral activities of isolated compounds from essential oils. Evid Based Complement Alternat Med. 2011:253643–253648. doi: 10.1093/ecam/nep187.
  • Azadi B, Nickavar B, Amin G. 2012. Volatile constituents of the peel and leaf of Citrus aurantium L. cultivated in the north of Iran. J Pharmaceut Health Sci. 1(3):37–41.
  • Azhdarzadeh F, Hojjati M. 2016. Chemical composition and antimicrobial activity of leaf, ripe and unripe peel of bitter orange (Citrus aurantium) essential oils. Nutr Food Sci Res. 3(1):43–50. doi: 10.18869/acadpub.nfsr.3.1.43.
  • Badawy M, Marei G, Rabea EI, Taktak NEM. 2019. Antimicrobial and antioxidant activities of hydrocarbon and oxygenated monoterpenes against some foodborne pathogens through in vitro and in silico studies. Pestic Biochem Physiol. 158:185–200. doi: 10.1016/j.pestbp.2019.05.008.
  • Banday JA, Rather Z-U-K, Yatoo GN, Hajam MA, Bhat SA, Santhanakrishnan VP, Farozi A, Rather MA, Rasool S. 2022. Rather gas chromatographic-mass spectrometric analysis, antioxidant, antiproliferative and antibacterial activities of the essential oil of Prangos pabularia. Microb Pathog. 166:105540. doi: 10.1016/j.micpath.2022.105540.
  • Baran EJ, Peterson LR, Finegold SM. 1994. Methods for testing antimicrobial effectiveness in Bailey and Scott’s diagnostic microbiology. Vol. 63146. 9th ed. St. Louis (MO): Mosby-Year Book Inc.; p. 168–188.
  • Ben Bnina E, Hajlaoui H, Chaieb I, Daami-Remadi M, Said MB, Jannet HB. 2019. Chemical composition, antimicrobial and insecticidal activities of the Tunisian Citrus aurantium essential oils. Czech J Food Sci. 37(2):81–92. doi: 10.17221/202/2017-CJFS.
  • Ben Mansour R, Chaouachi R, Falleh F, Pichette A, Legault J, Ksouri R. 2022. Powerful anti-inflammatory, anti-Herpes and anticancer capacities of Thymelaea microphylla L. and TLC phenolic identification. J Nat Prod Res Appl. 1(2):1–16.
  • Benencia F, Courrèges MC. 2000. In vitro and in vivo activity of eugenol on human herpesvirus. Phytother Res. 14(7):495–500. doi: 10.1002/1099-1573(200011)14:7<495::AID-PTR650>3.0.CO;2-8.
  • Bennadja S, Ounaissia K, Bouzaata C, Ailane L. 2019. Chemical composition and antibacterial activity of the essential oil of Citrus aurantium L. growing in Eastern Algeria. Int J Innov Approach Agricult Res. 3(1):81–86.
  • Bonesi M, Loizzo MR, Leporini M, Tenuta MC, Passalacqua NG, Tundis R. 2018. Comparative evaluation of petitgrain oils from six Citrus species alone and in combination as potential functional antiradicals and antioxidant agents. Plant Biosyst. 152(5):986–993. doi: 10.1080/11263504.2017.1403396.
  • Chang MY, Shieh DE, Chen CC, Yeh CS, Dong HP. 2015. Linalool induces cell cycle arrest and apoptosis in leukemia cells and cervical cancer cells through CDKIs. Int J Mol Sci. 16(12):28169–28179. doi: 10.3390/ijms161226089.
  • Crowell JA, Fraley RC, Shaver PR. 1999. Measurement of individual differences in adolescent and adult attachment. In: Cassidy J, Shaver PR, editors. Handbook of attachment: theory research and clinical applications; New York: Guilford; p. 434–465.
  • Dahham SS, Tabana Y, Asif M, Ahmed M, Babu D, Hassan LE, Ahamed MBK, Sandai D, Barakat K, Siraki A, et al. 2021. β-caryophyllene induces apoptosis and inhibits angiogenesis in colorectal cancer models. Int J Mol Sci. 22(19):10550. doi: 10.3390/ijms221910550.
  • Darjazi B. 2013. Comparison of leaf components of sweet orange and sour orange (Citrus sp.). Int J Adv Biol Biomed Res. 1(12):1558–1568.
  • De Lencastre H, Oliveira D, Tomasz A. 2007. Antibiotic resistant Staphylococcus aureus: a paradigm of adaptive power. Curr Opin Microbiol. 10(5):428–435. doi: 10.1016/j.mib.2007.08.003.
  • de Man P, Verhoeven BAN, Verbrugh HA, Vos MC, van den Anker JN. 2000. An antibiotic policy to prevent emergence of resistant bacilli. Lancet. 355(9208):973–978. doi: 10.1016/s0140-6736(00)90015-1.
  • Deans SG. 1990. Evaluation of antimicrobial activity of essential (volatile) oils. Essent Oils Waxes. 12:309–320.
  • Dugo G, Bonaccorsi I, Sciarrone D, Costa R, Dugo P, Mondello L, Santi L, Fakhry HA. 2011. Characterization of oils from the fruits, leaves and flowers of the bitter orange tree. J Essent Oil Res. 23(2):45–59. doi: 10.1080/10412905.2011.9700446.
  • Elbe H, Ozturk F, Yigitturk G, Baygar T, Cavusoglu T. 2022. Anticancer activity of linalool: comparative investigation of ultrastructural changes and apoptosis in breast cancer cells. Ultrastruct Pathol. 46(4):348–358. doi: 10.1080/01913123.2022.2091068.
  • El-Haci IA, Bekkara FA. 2011. Antioxidant activity of stems and leaves organic fractions of Ecballium elaterium L. Ann Biol Res. 2:327–332.
  • Ellouze I, Abderrabba M, Sabaou N, Mathieu F, Lebrihi A, Bouajila J. 2012. Season’s variation impact on Citrus aurantium leaves essential oil: chemical composition and biological activities. J Food Sci. 77(9):T173–T180.
  • Elson C. 1995. Suppression of mevalonate pathway activities by dietary isoprenoids: protective roles in cancer and cardiovascular disease. J Nutr. 125(6 Suppl):1666S–1672S.
  • Gholivand MB, Piryaei M, Abolghasemi MM. 2013. Analysis of volatile oil composition of Citrus aurantium L. by microwave-assisted extraction coupled to headspace solid-phase microextraction with nanoporous based fibers. J Sep Sci. 36(5):872–877. doi: 10.1002/jssc.201200674.
  • Graham DR, Dixon RE, Hughes JM, Thorns BC. 1985. Disk diffusion antimicrobial susceptibility testing for clinical and epidemiological purposes. Am J Infect Control. 13(6):241–249. doi: 10.1016/0196-6553(85)90024-0.
  • Guerrini A, Rossi D, Grandini A, Scalvenzi L, Noriega Rivera PF, Andreotti E, Tacchini M, Spagnoletti A, Poppi I, Maietti S, et al. 2014. Biological and chemo-diverse characterization of Amazonian (Ecuador) Citrus petitgrains. J Appl Bot Food Qual. 87:108–116.
  • Hajlaoui H, Mighri H, Aouni M, Gharsallah N, Kadri A. 2016. Chemical composition and in vitro evaluation of antioxidant, antimicrobial, cytotoxicity and anti-acetylcholinesterase properties of Tunisian Origanum majorana L. essential oil. Microb Pathog. 95:86–94. doi: 10.1016/j.micpath.2016.03.003.
  • Isabel M, Carvalho F, Osta M. 2002. Anxiolytic and sedative effects of extracts and essential oil from Citrus aurantium L. Pharm Soc Jpn. 25:1629–1633.
  • Iwasaki M, Zhao H, Jaffer T, Unwith S, Benzonana L, Lian Q, Sakamoto A, Ma D. 2016. Volatile anaesthetics enhance the metastasis related cellular signalling including CXCR2 of ovarian cancer cells. Oncotarget. 7(18):26042–26056. doi: 10.18632/oncotarget.8304.
  • Jing L, Lei Z, Li L, Xie R, Xi W, Guan Y, Sumner LW, Zhou Z. 2014. Antifungal activity of Citrus essential oils. J Agric Food Chem. 62(14):3011–3033. doi: 10.1021/jf5006148.
  • Jirovetz L, Buchbauer G, Stoilova I, Stoyanova A, Krastanov A, Schmidt E. 2006. Chemical composition and antioxidant properties of clove leaf essential oil. J Agric Food Chem. 54(17):6303–6307. doi: 10.1021/jf060608c.
  • Khalid KA. 2021. Growth sites and their impacts on sour orange ‘Citrus aurantium (Tournef.)ʼ essential oil. Biocat Agric Biotech. 31:101909. doi: 10.1016/j.bcab.2021.101909.
  • Khosravi M, Khakpour S, Adibi L, Hadipour Jahromy M. 2014. A study of the effect of Citrus aurantium L. essential oil on anxiety and its interaction with GABAergic pathways in male mice. JBBS. 4(10):470–476. doi: 10.4236/jbbs.2014.410046.
  • Lei J, Wang Q, Li G, Li Y, Zhang P, Xu G. 2021. β-Caryophyllene from chilli pepper inhibits the proliferation of non-small cell lung cancer cells by affecting miR-659-3p-targeted sphingosine kinase 1 (SphK1). Int J Gen Med. 14:9599–9613. doi: 10.2147/IJGM.S338513.
  • Lota ML, de Rocca Serra D, Jacquemond C, Tomi F, Casanova J. 2001. Chemical variability of peel and leaf essential oils of sour orange. Flavour Fragr J. 16(2):89–96. doi: 10.1002/1099-1026(200103/04)16:2<89::AID-FFJ950>3.0.CO;2-D.
  • Majnooni M, Mansouri K, Gholivand M, Mostafaie A, Mohammadi-Motlagh HR, Afnanzade NS, Abolghasemi MM, Piriyaei M. 2012. Chemical composition, cytotoxicity and antioxidant activities of the essential oil from the leaves of Citrus aurantium L. Afr J Biotech. 11(2):498–503.
  • Mejri H, Khetatfa T, Aidi Wannes W, Smaoui A, Saidani Tounsi M. 2022. Histochemistry, chemical composition and antioxidant activity of Citrus aurantium L. essential oil during leaf development. J Essent Oil Res. 34(4):329–338. doi: 10.1080/10412905.2022.2067255.
  • Metoui N, Gargouri S, Amri I, Fezzani T, Jamoussi B, Hamrouni L. 2015. Activity antifungal of the essential oils; aqueous and ethanol extracts from Citrus aurantium L. Nat Prod Res. 29(23):2238–2241. doi: 10.1080/14786419.2015.1007136.
  • Mishra NN, Prasad T, Sharma N, Payasi A, Prasad R, Gupta DK, Singh R. 2007. Pathogenicity and drug resistance in Candida albicans and other yeast species. A review. Acta Microbiol Immunol Hung. 54(3):201–235. doi: 10.1556/AMicr.54.2007.3.1.
  • Mohamed AA, Alotaibi BM. 2022. Essential oils of some medicinal plants and their biological activities: a mini review. JUmm Al-Qura Univ Appl Sci. 9(1):40–49. doi: 10.1007/s43994-022-00018-1.
  • Moo CL, Yang SK, Osman MA, Yuswan MH, Loh JY, Lim WM, Lim SHE, Lai KS. 2020. Antibacterial activity and mode of action of β-caryophyllene on Bacillus cereus. Pol J Microbiol. 69(1):1–6. doi: 10.33073/pjm-2020-007.
  • Okla MK, Alamri SA, MZM S, Ali HM, Behiry SI, Nasser RA, Alaraidh IA, Sm A-G, Soufan W. 2019. Yield, phytochemical constituents, and antibacterial activity of essential oils from the leaves/twigs, branches, branch wood, and branch bark of sour orange (Citrus aurantium L.). Process. 7:1–15.
  • Ouedrhiri W, Bouhdid S, Balouiri M, El Ouali Lalami A, Moja S, Ouazzani Chahdi F, Greche H. 2015. Chemical composition of Citrus aurantium L. leaves and zest essential oils, their antioxidant, antibacterial single and combined effects. J Chem Pharmaceut Res. 7(1):78–84.
  • Oulebsir C, Mefti-Korteby H, Djazouli ZE, Zebib B, Merah O. 2022. Essential oil of Citrus aurantium L. leaves: composition, antioxidant activity, elastase and collagenase inhibition. Agronomy. 12(6):1466. doi: 10.3390/agronomy12061466.
  • Pan G, Zhang W. 2019. Linalool monoterpene exerts potent antitumor effects in OECM 1 human oral cancer cells by inducing sub-G1 cell cycle arrest, loss of mitochondrial membrane potential and inhibition of PI3K/AKT biochemical pathway. J Buon. 24(1):323–328.
  • Pratama MD, Premjet S, Choopayak C, Premjet D. 2019. Chemical composition and antioxidant activities of essential oil from Somsa (Citrus aurantium L.) in Phitsanulok province Thailand. Asia Pac J Sci Technol. 24(1):1–8.
  • Rajesh D, Howard SP. 2003. Perillyl alcohol mediated radiosensitization via augmentation of the Fas pathway in prostate cancer cells. Prostate. 57(1):14–23. doi: 10.1002/pros.10269.
  • Randrianarivelo R, Sarter S, Odoux E, Brat P, Lebrun M, Romestand B, Menut C, Andrianoelisoa H, Raherimandimby M, Danthu P. 2009. Composition and antimicrobial activity of essential oils of Cinnamosma fragrans. Food Chem. 114(2):680–684. doi: 10.1016/j.foodchem.2008.10.007.
  • Rodenak-Kladniew B, Castro MA, Crespo R, Galle M, García de Bravo M. 2020. Anti-cancer mechanisms of linalool and 1,8-cineole in non-small cell lung cancer A549 cells. Heliyon. 6(12):e05639. doi: 10.1016/j.heliyon.2020.e05639.
  • Sandner G, Heckmann M, Weghuber J. 2020. Immunomodulatory activities of selected essential oils. Biomolecules. 10(8):1139. doi: 10.3390/biom10081139.
  • Sarrou E, Chatzopoulou P, Dimassi-Theriou K, Therios I. 2013. Volatile constituents and antioxidant activity of peel, flowers and leaf oils of Citrus aurantium L. growing in Greece. Molecules. 18(9):10639–10647. doi: 10.3390/molecules180910639.
  • Sherif AE, Marzouk AM, Zaghloul MG, Halim AF. 2015. Chemical composition and cytotoxic activity of petitgrain essential oil of Citrus aurantium L. “Russian colon”. J Am Sci. 11(8):64–68.
  • Sonboli A, Eftekhar F, Yousefzadi M, Kanani MR. 2005. Antibacterial activity and chemical composition of the essential oil of Grammosciadium platycarpum Boiss. from Iran. Z Naturforsch C J Biosci. 60(1–2):30–34. doi: 10.1515/znc-2005-1-206.
  • Sriti J, Haj Salem M, Aidi Wannes W, Bachrouch O, Mejri H, Belloumi S, Fares N, Jallouli S, Haoual H, Mediouni Ben Jemaa J, et al. 2023. Antioxidant, antibacterial and insecticidal activities of cypress (Cupressus sempervirens L.) essential oil Antioxidant, antibacterial and insecticidal activities of cypress (Cupressus sempervirens L.) essential oil. Int J Environ Health Res. 28:1–12. doi: 10.1080/09603123.2023.2207475.
  • Suryawanshi JAS. 2011. An overview of Citrus aurantium used in treatment of various diseases. Afr J Plant Sci. 5:390–395.
  • Trabelsi D, Haj Ammar A, Bouabdallah F, Zagrouba F. 2014. Antioxidant and antimicrobial activities of essential oils and methanolic extracts of Tunisian Citrus aurantium L. IOSR J Environ Sci Toxicol Food Technol. 8(5):18–27. doi: 10.9790/2402-08521827.
  • Yu X, Liao B, Zhu P, Cheng S, Du Z, Jiang G. 2021. β-caryophyllene induces apoptosis and inhibits cell proliferation by deregulation of STAT-3/mTOR/AKT signaling in human bladder cancer cells: an in vitro study. J Biochem Molecul Toxicol. 35(10):e22863.
  • Zawawi DD, Jăafar H, Ali MA. 2011. Total phenolic compounds and antioxidamt properties in different stage of B. racemosa and B. spicata leaf. Int Conf Biol Environ Chem. 24:100–105.
  • Zubaid-ul-khazir R, Yatoo GN, Wani H, Shah SA, Zargar MI, Rather MA, Banday JA. 2021. Gas chromatographic-mass spectrometric analysis, antibacterial, antioxidant and antiproliferative activities of the needle essential oil of Abies pindrow growing wild in Kashmir India. Microb Pathog. 158:105013. doi: 10.1016/j.micpath.2021.105013.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.