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Chitosan nanoparticles containing limonene and limonene-rich essential oils: potential phytotherapy agents for the treatment of melanoma and breast cancers

Alipanah, Hiva, Farjam, Mojtaba, Zarenezhad, Elham, Roozitalab, Ghazaal, Osanloo, Mahmoud·2021·BMC Complementary Medicine and Therapies
DOI 10.1186/s12906-021-03362-7PMC PMC8254332
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Abstract

Background: Melanoma and breast cancers are two common cancers worldwide. Due to the side effects of chemotherapy drugs and the occurring resistance against them, the development of green drugs has been received more attention. Methods: The anticancer effects of three essential oils from the Citrus family and their identified major constituents (limonene) were first investigated against melanoma and breast cancer cell lines (A-375 and MDA-MB-468). By preparing chitosan nanoparticles containing them, an attempt was then made to improve their effectiveness. Results: Chitosan nanoparticles containing Citrus sinensis and Citrus limon essential oils with IC 50 s of 0.03 and 0.124 μg/mL on A-375 cells, and 23.65 and 40.32 μg/mL on MDA-MB-468 showed distinct anticancer efficacies. Conclusion: The prepared formulations could thus be considered as green anticancer agents in complementary medicine and therapies.

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Fig. 1 Steps of preparation of chitosan nanoparticles containing EOs or limonene
Fig. 1 Steps of preparation of chitosan nanoparticles containing EOs or limoneneCC BY · PubMed Central
Fig. 2 Chitosan nanoparticles containing limonene and EOs of C. aurantium, C. limon, and C. sinensis: A) LimChiNPs 209 ± 13 nm, B) CAChiNPs 173 ± 6 nm, C) CLChiNPs 181 ± 4 nm, D) CSChiNPs 156 ± 8 nm
Fig. 2 Chitosan nanoparticles containing limonene and EOs of C. aurantium, C. limon, and C. sinensis: A) LimChiNPs 209 ± 13 nm, B) CAChiNPs 173 ± 6 nm, C) CLChiNPs 181 ± 4 nm, D) CSChiNPs 156 ± 8 nmCC BY · PubMed Central
Fig. 3 ATR-FTIR of samples; A) chitosan nanoparticles, B) limonene, C) ChiNPs containing limonene, D) C. aurantium EO, E) ChiNPs C. aurantium EO, F) C. limon EO, G) ChiNPs containing C. limon EO, H) C. sinensis EO, and I) ChiNPs containing C. sinensis EO
Fig. 3 ATR-FTIR of samples; A) chitosan nanoparticles, B) limonene, C) ChiNPs containing limonene, D) C. aurantium EO, E) ChiNPs C. aurantium EO, F) C. limon EO, G) ChiNPs containing C. limon EO, H) C. sinensis EO, and I) ChiNPs containing C. sinensis EOCC BY · PubMed Central
Fig. 4 Anticancer effect of limonene and EOs of C. aurantium, C. limon, and C. sinensis (CAEO, CLEO, and CSEO) and chitosan nanoparticles contained them (LimChiNPs, CAChiNPs, CLChiNPs, and CSChiNPs) against A-375 cells. Data are presented as mean ± standard deviation (n = 3).
Fig. 4 Anticancer effect of limonene and EOs of C. aurantium, C. limon, and C. sinensis (CAEO, CLEO, and CSEO) and chitosan nanoparticles contained them (LimChiNPs, CAChiNPs, CLChiNPs, and CSChiNPs) against A-375 cells. Data are presented as mean ± standard deviation (n = 3).CC BY · PubMed Central
Fig. 5 Anticancer effect of limonene and EOs of C. aurantium, C. limon, and C. sinensis (CAEO, CLEO, and CSEO) and chitosan nanoparticles contained them (LimChiNPs, CAChiNPs, CLChiNPs, and CSChiNPs) against MDA-MB-468. Data are presented as mean ± standard deviation (n = 3)
Fig. 5 Anticancer effect of limonene and EOs of C. aurantium, C. limon, and C. sinensis (CAEO, CLEO, and CSEO) and chitosan nanoparticles contained them (LimChiNPs, CAChiNPs, CLChiNPs, and CSChiNPs) against MDA-MB-468. Data are presented as mean ± standard deviation (n = 3)CC BY · PubMed Central

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Research works printed but not linked: 44

  1. Sharma GN, Dave R, Sanadya J, Sharma P, Sharma K. Various types and management of breast cancer: an overview. J Adv Pharm Technol Res. 2010;1(2):109–26. · DOI
  2. McGuire A, Brown JA, Kerin MJ. Metastatic breast cancer: the potential of miRNA for diagnosis and treatment monitoring. Cancer Metastasis Rev. 2015;34(1):145–55. https://doi.org/10.1007/s10555-015-9551-7. · DOI
  3. Gordon R: Skin cancer: an overview of epidemiology and risk factors. In: Semin Oncol Nurs: 2013: Elsevier; 2013: 160–169. · DOI
  4. Uong A, Zon LI. Melanocytes in development and cancer. J Cell Physiol. 2010;222(1):38–41. https://doi.org/10.1002/jcp.21935. · DOI
  5. Haider T, Pandey V, Banjare N, Gupta PN, Soni V. Drug resistance in cancer: mechanisms and tackling strategies. Pharmacol Rep. 2020;72(5):1125–51. https://doi.org/10.1007/s43440-020-00138-7. · DOI · Paper page
  6. Blowman K, Magalhães M, Lemos M, Cabral C, Pires I. Anticancer properties of essential oils and other natural products. Evid Based Complement Alternat Med. 2018;2018:1–12. https://doi.org/10.1155/2018/3149362. · DOI
  7. Pavithra PS, Mehta A, Verma RS. Essential oils: from prevention to treatment of skin cancer. Drug Discov Today. 2019;24(2):644–55. https://doi.org/10.1016/j.drudis.2018.11.020. · DOI
  8. Russo R, Corasaniti MT, Bagetta G, Morrone LA. Exploitation of cytotoxicity of some essential oils for translation in cancer therapy. Evid Based Complement Alternat Med. 2015;2015:397821. · DOI
  9. Dobetsberger C, Buchbauer G. Actions of essential oils on the central nervous system: an updated review. Flavour Fragr J. 2011;26(5):300–16. https://doi.org/10.1002/ffj.2045. · DOI
  10. Shen C-Y, Jiang J-G, Zhu W, Ou-Yang Q. Anti-inflammatory effect of essential oil from Citrus aurantium L. var. Amara Engl. J Agric Food Chem. 2017;65(39):8586–94. https://doi.org/10.1021/acs.jafc.7b02586. · DOI
  11. Suryawanshi JAS. An overview of Citrus aurantium used in treatment of various diseases. African J Plant Sci. 2011;5(7):390–5.
  12. Choi H-S, Song HS, Ukeda H, Sawamura M. Radical-scavenging activities of citrus essential oils and their components: detection using 1, 1-diphenyl-2-picrylhydrazyl. J Agric Food Chem. 2000;48(9):4156–61. https://doi.org/10.1021/jf000227d. · DOI
  13. González-Molina E, Domínguez-Perles R, Moreno D, García-Viguera C. Natural bioactive compounds of Citrus Limon for food and health. J Pharm Biomed Anal. 2010;51(2):327–45. https://doi.org/10.1016/j.jpba.2009.07.027. · DOI
  14. Ling APK, Chia JY, Hussein S, Harun AR. Physiological responses of Citrus sinensis to gamma irradiation. World Appl Sci J. 2008;5(1):12–9.
  15. Kammoun AK, Altyar AE, Gad HA. Comparative metabolic study of Citrus Sinensis leaves cultivars based on GC-MS and their cytotoxic activity. J Pharm Biomed Anal. 2021;198:113991. · DOI
  16. Najar B, Shortrede JE, Pistelli L, Buhagiar J. Chemical composition and in vitro cytotoxic screening of sixteen commercial essential oils on five Cancer cell lines. Chem Biodivers. 2020;17(1):e1900478. https://doi.org/10.1002/cbdv.201900478. · DOI · Paper page
  17. Sun J. D-limonene: safety and clinical applications. Altern Med Rev. 2007;12(3):259–64.
  18. Jia S-S, Xi G-P, Zhang M, Chen Y-B, Lei B, Dong X-S, et al. Induction of apoptosis by D-limonene is mediated by inactivation of Akt in LS174T human colon cancer cells. Oncol Rep. 2013;29(1):349–54. https://doi.org/10.3892/or.2012.2093. · DOI · Paper page
  19. Ciriminna R, Lomeli-Rodriguez M, Cara PD, Lopez-Sanchez JA, Pagliaro M. Limonene: a versatile chemical of the bioeconomy. Chem Commun. 2014;50(97):15288–96. https://doi.org/10.1039/C4CC06147K. · DOI
  20. Araújo-Filho HGd, Dos Santos JF, Carvalho MT, Picot L, Fruitier-Arnaudin I, Groult H, Quintans-Júnior LJ, Quintans JS. Anticancer activity of limonene: A systematic review of target signaling pathways. Phytother Res. 2021:1–14. https://doi.org/10.1002/ptr.7125. · DOI · Paper page
  21. de Vasconcelos Cerqueira Braz J, de Carvalho FO, de Vasconcelos Cerqueira Meneses D, Calixto FAF, Santana HSR, Almeida IB, de Aquino LAG, de Souza Araújo AA, Serafini MR. Mechanism of Action of Limonene in Tumor Cells: A Systematic Review and Metanalysis. Curr Pharm Des. 2020. https://doi.org/10.2174/1381612826666201026152902. · DOI
  22. Manuele MG, Barreiro Arcos ML, Davicino R, Ferraro G, Cremaschi G, Anesini C. Limonene exerts antiproliferative effects and increases nitric oxide levels on a lymphoma cell line by dual mechanism of the ERK pathway: relationship with oxidative stress. Cancer Investig. 2010;28(2):135–45. https://doi.org/10.3109/07357900903179583. · DOI
  23. Mukhtar YM, Adu-Frimpong M, Xu X, Yu J. Biochemical significance of limonene and its metabolites: future prospects for designing and developing highly potent anticancer drugs. Biosci Rep. 2018;38(6):BSR20181253. · DOI
  24. Abedinpour N, Ghanbariasad A, Taghinezhad A, Osanloo M. Preparation of Nanoemulsions of Mentha piperita Essential Oil and Investigation of Their Cytotoxic Effect on Human Breast Cancer Lines. BioNanoScience. 2021;11:428–36. · DOI
  25. Osanloo M, Sedaghat M, Sereshti H, Rahmanian M, Saeedi Landi F, Amani A. Chitosan nanocapsules of tarragon essential oil with low cytotoxicity and long-lasting activity as a green nano-larvicide. J Nanostruct. 2019;9(4):723–35.
  26. Abdollahi A, Mirzaei E, Amoozegar F, Moemenbellah-Fard MD, Zarenezhad E, Osanloo M. High Antibacterial Effect of Impregnated Nanofiber Mats with a Green Nanogel Against Major Human Pathogens. BioNanoScience. 2021;11:549–58. · DOI
  27. Venditti A, Frezza C, Maggi F, Lupidi G, Bramucci M, Quassinti L, et al. Phytochemistry, micromorphology and bioactivities of Ajuga chamaepitys (L.) Schreb. (Lamiaceae, Ajugoideae): two new harpagide derivatives and an unusual iridoid glycosides pattern. Fitoterapia. 2016;113:35–43. https://doi.org/10.1016/j.fitote.2016.06.016. · DOI
  28. Venditti A, Bianco A, Frezza C, Serafini M, Giacomello G, Giuliani C, et al. Secondary metabolites, glandular Trichomes and biological activity of Sideritis montana L. subsp. Montana from Central Italy. Chem Biodivers. 2016;13(10):1380–90. https://doi.org/10.1002/cbdv.201600082. · DOI
  29. Cianfaglione K, Blomme EE, Quassinti L, Bramucci M, Lupidi G, Dall'Acqua S, Maggi F. Cytotoxic Essential Oils from Eryngium campestre and Eryngium amethystinum (Apiaceae) Growing in Central Italy. Chem Biodivers. 2017;14:e1700096. · DOI
  30. Momtazi AA, Askari-Khorasgani O, Abdollahi E, Sadeghi-Aliabadi H, Mortazaeinezhad F, Sahebkar A. Phytochemical analysis and cytotoxicity evaluation of Kelussia odoratissima Mozaff. J Acupunct Meridian Stud. 2017;10(3):180–6. https://doi.org/10.1016/j.jams.2017.02.002. · DOI
  31. Ghanbariasad A, Osanloo M. Development of two stable green nanoformulations with potent anticancer properties. Nanomed Res J. 2020;5(3):234–44.
  32. Souza JM, Caldas AL, Tohidi SD, Molina J, Souto AP, Fangueiro R, et al. Properties and controlled release of chitosan microencapsulated limonene oil. Rev Bras Farmacogn. 2014;24(6):691–8. https://doi.org/10.1016/j.bjp.2014.11.007. · DOI
  33. Khoshakhlagh K, Koocheki A, Mohebbi M, Allafchian A. Development and characterization of electrosprayed Alyssum homolocarpum seed gum nanoparticles for encapsulation of d-limonene. J Colloid Interface Sci. 2017;490:562–75. https://doi.org/10.1016/j.jcis.2016.11.067. · DOI
  34. Karimirad R, Behnamian M, Dezhsetan S, Sonnenberg A. Chitosan nanoparticles-loaded Citrus aurantium essential oil: a novel delivery system for preserving the postharvest quality of Agaricus bisporus. J Sci Food Agric. 2018;98(13):5112–9. https://doi.org/10.1002/jsfa.9050. · DOI
  35. Karimirad R, Behnamian M, Dezhsetan S. Bitter orange oil incorporated into chitosan nanoparticles: preparation, characterization and their potential application on antioxidant and antimicrobial characteristics of white button mushroom. Food Hydrocoll. 2020;100:105387. https://doi.org/10.1016/j.foodhyd.2019.105387. · DOI
  36. Bento R, Pagán E, Berdejo D, de Carvalho RJ, García-Embid S, Maggi F, et al. Chitosan nanoemulsions of cold-pressed orange essential oil to preserve fruit juices. Int J Food Microbiol. 2020;331:108786. https://doi.org/10.1016/j.ijfoodmicro.2020.108786. · DOI
  37. Hasani S, Ojagh SM, Ghorbani M. Nanoencapsulation of lemon essential oil in chitosan-Hicap system. Part 1: study on its physical and structural characteristics. Int J Biol Macromol. 2018;115:143–51. https://doi.org/10.1016/j.ijbiomac.2018.04.038. · DOI
  38. Hajizadeh MR, Maleki H, Barani M, Fahmidehkar MA, Mahmoodi M, Torkzadeh-Mahani M. In vitro cytotoxicity assay of D-limonene niosomes: an efficient nano-carrier for enhancing solubility of plant-extracted agents. Res Pharm Sci. 2019;14(5):448–58. https://doi.org/10.4103/1735-5362.268206. · DOI
  39. Li P-H, Lu W-C. Effects of storage conditions on the physical stability of d-limonene nanoemulsion. Food Hydrocoll. 2016;53:218–24. https://doi.org/10.1016/j.foodhyd.2015.01.031. · DOI
  40. Navaei Shoorvarzi S, Shahraki F, Shafaei N, Karimi E, Oskoueian E. Citrus aurantium L. bloom essential oil nanoemulsion: Synthesis, characterization, cytotoxicity, and its potential health impacts on mice. J Food Biochem. 2020;44(5):e13181. · DOI
  41. Raimondo S, Naselli F, Fontana S, Monteleone F, Dico AL, Saieva L, et al. Citrus Limon-derived nanovesicles inhibit cancer cell proliferation and suppress CML xenograft growth by inducing TRAIL-mediated cell death. Oncotarget. 2015;6(23):19514–27. https://doi.org/10.18632/oncotarget.4004. · DOI
  42. Souto EB, Zielinska A, Souto SB, Durazzo A, Lucarini M, Santini A, et al. (+)-Limonene 1, 2-epoxide-loaded slns: Evaluation of drug release, antioxidant activity, and cytotoxicity in an HaCaT cell line. Int J Mol Sci. 2020;21(4):1449. · DOI
  43. Venditti A, Bianco A, Muscolo C, Zorzetto C, Sanchez-Mateo CC, Rabanal RM, et al. Bioactive secondary metabolites from Schizogyne sericea (Asteraceae) endemic to Canary Islands. Chem Biodivers. 2016;13(7):826–36. https://doi.org/10.1002/cbdv.201500222. · DOI
  44. Gambini V, Tilio M, Maina EW, Andreani C, Bartolacci C, Wang J, et al. In vitro and in vivo studies of gold(I) azolate/phosphane complexes for the treatment of basal like breast cancer. Eur J Med Chem. 2018;155:418–27. https://doi.org/10.1016/j.ejmech.2018.06.002. · DOI

Cited by

Metadata

Authors
Alipanah, H., Farjam, M., Zarenezhad, E., Roozitalab, G., & Osanloo, M.
Venue
BMC Complementary Medicine and Therapies
Publisher
Springer Science and Business Media LLC
Published
2021-07-02
Volume
21
Issue
1
ISSN
2662-7671
DOI
10.1186/s12906-021-03362-7
PMC
PMC8254332
Cited by
77
References
0
Language
en
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