Nanomedicine Research Journal

Nanomedicine Research Journal

Lemon Essential Oil Nanoemulsion containing Ascorbyl Tetraisopalmitate: Investigating the Relationship Between Surfactant HLB and Size

Document Type : Original Research Article

Authors
Aram Afkhami 1
Siavash Valizadeh 2
Yaser Yousefpoor 3
Alireza Valizadeh 4
1 Department of Research and Development, DNA Chemical Co., Tehran, Iran
2 Department of Industrial Engineering, Sharif University of Technology, Tehran, Iran
3 Department of Medical Biotechnology, School of Paramedical Sciences, Torbat Heydariyeh University of Medical Sciences, Iran
4 Department of Medical Nanotechnology, School of Advanced Technologies in Medicine, Tehran University of Medical Sciences, Tehran, Iran
10.22034/nmrj.2025.2045695.1675
Abstract
Vitamin C (Vit-C) and lemon essential oil have several notably benefits for human skin physiology such as stimulating the biosynthesis of collagen, reduce acne and dark spot. But, they poorly bypass the epidermis stratum corneum barrier. Also, lemon essential oil has high vapor pressure. To address these challenges, our aim was preparing and size optimizing a lipophilic version of Vit-C (Ascorbyl tetraisopalmitate) and lemon essential oil by encapsulation of them inside of nanoemulsion droplets (used as oil phase of nanoemulsion), for improving skin diffusion and delivery across the stratum corneum cells. Lemon essential oil was characterized with gas chromatography-mass spectroscopy. Multiple regression analysis was used for obtaining of the HLB required of mix Lemon essential oil and Vit-C. The results revealed that the concentration ratio of Tween 80 to Tween 85 is important for achieving nano-range particle size with good stability. Particle size was determined by Dynamic light scattering method. FT-IR showed encapsulation of Vit-C and lemon essential oil inside of nanoemulsion droplets. The pH of final formulation (F1) was 4.8. Current study indicated that the stable lemon essential oil nanoemulsion contain Vit-C is a good candidate for increasing dispersity and protection of lemon essential oil and Vit-C in water. 
Keywords
Ascorbyl Tetraisopalmitate
Vitamin C
Lemon Essential oil
Nanoemulsion
Topical Drug delivery
Topical Vitamin C

Subjects

1.    Carr, A.C. and S. Maggini, Vitamin C and Immune Function. Nutrients, 2017. 9(11): p. 1211. https://doi.org/10.3390/nu9111211
2.    Gref, R., et al., Vitamin C-squalene bioconjugate promotes epidermal thickening and collagen production in human skin. Scientific Reports, 2020. 10(1): p. 16883. https://doi.org/10.1038/s41598-020-72704-1
3.    Boo, Y.C., Ascorbic acid (vitamin C) as a cosmeceutical to increase dermal collagen for skin antiaging purposes: emerging combination therapies. Antioxidants, 2022. 11(9): p. 1663. https://doi.org/10.3390/antiox11091663
4.    Lis, D.M. and K. Baar, Effects of different vitamin C-enriched collagen derivatives on collagen synthesis. International journal of sport nutrition and exercise metabolism, 2019. 29(5): p. 526-531. https://doi.org/10.1123/ijsnem.2018-0385
5.    Boyera, N., I. Galey, and B.A. Bernard, Effect of vitamin C and its derivatives on collagen synthesis and cross-linking by normal human fibroblasts. International Journal of Cosmetic Science, 1998. 20(3): p. 151-158. https://doi.org/10.1046/j.1467-2494.1998.171747.x
6.    Lv, X., Z. Wu, and X. Qi, High skin permeation, deposition and whitening activity achieved by xanthan gum string vitamin c flexible liposomes for external application. International Journal of Pharmaceutics, 2022. 628: p. 122290. https://doi.org/10.1016/j.ijpharm.2022.122290
7.    Rozman, B. and M. Gasperlin, Stability of vitamins C and E in topical microemulsions for combined antioxidant therapy. Drug delivery, 2007. 14(4): p. 235-245. https://doi.org/10.1080/10717540601067786
8.    diligent, s. vitamin c serum in oil. 2023 [cited 2023 August 4]; Available from: https://skindiligent.com/products/vitamin-c-serum-in-oil
9.    Bastianini, M., M. Sisani, and A. Petracci, Ascorbyl Tetraisopalmitate Inclusion into Υ-Cyclodextrin and Mesoporous SBA-15: Preparation, Characterization and In Vitro Release Study. Cosmetics, 2017. 4(3): p. 21. https://doi.org/10.3390/cosmetics4030021
10.    Jeon, J.-S., et al., Simultaneous Detection of Glabridin, (−)-α-Bisabolol, and Ascorbyl Tetraisopalmitate in Whitening Cosmetic Creams Using HPLC-PAD. Chromatographia, 2016. 79(13): p. 851-860. https://doi.org/10.1007/s10337-016-3104-2
11.    Lin, L.-Y., et al., Lime (Citrus aurantifolia (Christm.) Swingle) Essential Oils: Volatile Compounds, Antioxidant Capacity, and Hypolipidemic Effect. Foods, 2019. 8(9): p. 398. https://doi.org/10.3390/foods8090398
12.    Misharina, T.A. and A.L. Samusenko, Antioxidant properties of essential oils from lemon, grapefruit, coriander, clove, and their mixtures. Applied Biochemistry and Microbiology, 2008. 44(4): p. 438-442. https://doi.org/10.1134/S0003683808040182
13.    Białoń, M., et al., The Influence of Chemical Composition of Commercial Lemon Essential Oils on the Growth of Candida Strains. Mycopathologia, 2014. 177(1): p. 29-39. https://doi.org/10.1007/s11046-013-9723-3
14.    Yazgan, H., Y. Ozogul, and E. Kuley, Antimicrobial influence of nanoemulsified lemon essential oil and pure lemon essential oil on food-borne pathogens and fish spoilage bacteria. International journal of food microbiology, 2019. 306: p. 108266. https://doi.org/10.1016/j.ijfoodmicro.2019.108266
15.    Arena, M.E., M.R. Alberto, and E. Cartagena, Potential use of Citrus essential oils against acute respiratory syndrome caused by coronavirus. Journal of Essential Oil Research, 2021. 33(4): p. 330-341. https://doi.org/10.1080/10412905.2021.1912839
16.    Valizadeh, A., et al., Preparation and Comparison of Effects of Different Herbal Oil Ointments as Wound-Healing Agents. Cells Tissues Organs, 2019. 207(3-4): p. 177-186. https://doi.org/10.1159/000503624
17.    Valizadeh, A., et al., Levofloxacin nanoemulsion gel has a powerful healing effect on infected wound in streptozotocin-induced diabetic rats. Drug Delivery and Translational Research, 2021. 11(1): p. 292-304. https://doi.org/10.1007/s13346-020-00794-5
18.    Keshvadi, M., et al., Comparative study of antibacterial inhibitory effect of silver nanoparticles and garlic oil nanoemulsion with their combination. Biointerface Res. Appl. Chem, 2019. 9(6): p. 4560-4566. https://doi.org/10.33263/BRIAC96.560566
19.    Valizadeh, A., et al., Increased antibacterial activity of Cinnamon Oil Microemulsionin Comparison with Cinnamon Oil Bulk and Nanoemulsion. Nanomedicine Research Journal, 2018. 3(1): p. 37-43.
20.    Yousefpoor, Y., et al., Current challenges ahead in preparation, characterization, and pharmaceutical applications of nanoemulsions. Wiley interdisciplinary reviews. Nanomedicine and nanobiotechnology, 2023. 15(6): p. e1920. https://doi.org/10.1002/wnan.1920
21.    Valizadeh, A., et al., Design and development of novel formulation of Aloe Vera nanoemulsion gel contained erythromycin for topical antibacterial therapy: In vitro and in vivo assessment. Journal of Drug Delivery Science and Technology, 2022. 74: p. 103519. https://doi.org/10.1016/j.jddst.2022.103519
22.    Yu, H. and Q. Huang, Improving the Oral Bioavailability of Curcumin Using Novel Organogel-Based Nanoemulsions. Journal of Agricultural and Food Chemistry, 2012. 60(21): p. 5373-5379. https://doi.org/10.1021/jf300609p
23.    Bertuzzi, G., et al., Antioxidative action of Citrus limonum essential oil on skin. Eur. J. Med. Plants, 2013. 3: p. 1-9. https://doi.org/10.9734/EJMP/2013/1987
24.    Mumtaz, S., et al., Aging and its treatment with vitamin C: a comprehensive mechanistic review. Molecular Biology Reports, 2021. 48(12): p. 8141-8153. https://doi.org/10.1007/s11033-021-06781-4
25.    Mumtaz, S., et al., Evaluation of antibacterial activity of vitamin C against human bacterial pathogens. Brazilian Journal of Biology, 2021. 83: p. e247165. https://doi.org/10.1590/1519-6984.247165
26.    Bazylińska, U., J. Kulbacka, and K.A. Wilk, Dicephalic ionic surfactants in fabrication of biocompatible nanoemulsions: Factors influencing droplet size and stability. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 2014. 460: p. 312-320. https://doi.org/10.1016/j.colsurfa.2013.12.042
27.    Ke, Z., X. Hou, and X.-B. Jia Design and optimization of self-nanoemulsifying drug delivery systems for improved bioavailability of cyclovirobuxine D. Drug design, development and therapy, 2016. 10, 2049-2060 DOI: https://doi.org/10.2147/dddt.s106356. https://doi.org/10.2147/DDDT.S106356
28.    Gurpreet, K. and S. Singh, Review of nanoemulsion formulation and characterization techniques. Indian Journal of Pharmaceutical Sciences, 2018. 80(5): p. 781-789. https://doi.org/10.4172/pharmaceutical-sciences.1000422
29.    Yadav, M.G., et al., Production of 6-O-l-Ascorbyl Palmitate by Immobilized Candida antarctica Lipase B. Applied Biochemistry and Biotechnology, 2018. 184(4): p. 1168-1186. https://doi.org/10.1007/s12010-017-2610-5
30.    Ali, H., K.D. Safa, and S. Rezazadeh, Nanoemulsion of Silybum marianum Seeds Extract: Evaluation of Stability, Antioxidant and Antibacterial Activity. Colloid Journal, 2023. 85(2): p. 287-297. https://doi.org/10.1134/S1061933X22600178
31.    Nunes, J.C., et al., Effect of green tea extract on gelatin-based films incorporated with lemon essential oil. Journal of Food Science and Technology, 2021. 58(1): p. 1-8. https://doi.org/10.1007/s13197-020-04469-4
32.    Hasani, S., S.M. Ojagh, and M. Ghorbani, Nanoencapsulation of lemon essential oil in Chitosan-Hicap system. Part 1: Study on its physical and structural characteristics. Int J Biol Macromol, 2018. 115(115): p. 143-151. https://doi.org/10.1016/j.ijbiomac.2018.04.038
33.    Permanasari, A.A., et al., The Potential of Waste Cooking Oil B20 Biodiesel Fuel with Lemon Essential Oil Bioadditive: Physicochemical Properties, Molecular Bonding, and Fuel Consumption. 2021, 2021. 16(3): p. 10. https://doi.org/10.9767/bcrec.16.3.10493.555-564
34.    Berechet, M.D., et al., Composition of the essential oil of Rosa damascena Mill. cultivated in Romania. Rev. Chim, 2015. 66(12): p. 1986-1991.
35.    Benoudjit, F., L. Maameri, and K. Ouared, Evaluation of the quality and composition of lemon (Citrus limon) peel essential oil from an Algerian fruit juice industry. Algerian Journal of Environmental Science and Technology, 2020. 6(4): p. 1575-1581.
36.    Bide, Y., M.A. Fashapoyeh, and S. Shokrollahzadeh, Structural investigation and application of Tween 80-choline chloride self-assemblies as osmotic agent for water desalination. Scientific Reports, 2021. 11(1): p. 17068. https://doi.org/10.1038/s41598-021-96199-6
37.    Batool, R., S. Ayub, and I. Akbar, Isolation of biosurfactant producing bacteria from petroleum contaminated sites and their characterization. Soil & Environment, 2017. 36(1): p. 35-44. https://doi.org/10.25252/SE/17/20992
38.    Li, X.-H., et al., Inhibition by tween-85 of the corrosion of cold rolled steel in 1.0 M hydrochloric acid solution. Journal of Applied Electrochemistry, 2009. 39(7): p. 1125-1135. https://doi.org/10.1007/s10800-008-9770-5
39.    Deng, M., et al., Tea saponins as natural emulsifiers and cryoprotectants to prepare silymarin nanoemulsion. LWT, 2022. 156(156): p. 113042. https://doi.org/10.1016/j.lwt.2021.113042
40.    Raina, N., et al., New Insights in Topical Drug Delivery for Skin Disorders: From a Nanotechnological Perspective. ACS omega, 2023. 8(22): p. 19145-19167. https://doi.org/10.1021/acsomega.2c08016
41.    Idrees, N., et al., Hemodialysis for treatment of levofloxacin-induced neurotoxicity. Hemodialysis International, 2019. 23(2): p. E40-E45. https://doi.org/10.1111/hdi.12687
42.    Ghiasi, Z., et al., Enhancing analgesic and anti-inflammatory effects of capsaicin when loaded into olive oil nanoemulsion: An in vivo study. International Journal of Pharmaceutics, 2019. 559: p. 341-347. https://doi.org/10.1016/j.ijpharm.2019.01.043
43.    Dragicevic, N. and H.I. Maibach, Percutaneous penetration enhancers physical methods in penetration enhancement. 1 ed. 2017: Springer. https://doi.org/10.1007/978-3-662-53273-7
44.    Raffaelli, V., et al., Levofloxacin-induced visual hallucina-tions: A case report and review of the literature. J Health Soc Sci, 2018. 3(1): p. 85-89.
45.    Ghanbariasad, A., et al., Nanoformulating Cinnamomum zeylanicum essential oil with an extreme effect on Leishmania tropica and Leishmania major. Journal of Drug Delivery Science and Technology, 2021. 63: p. 102436. https://doi.org/10.1016/j.jddst.2021.102436
46.    Osanloo, M., et al., Antibacterial potential of essential oils of Zataria multiflora and Mentha piperita, micro- and nano-formulated forms. Iran J Microbiol, 2020. 12(1): p. 43-51. https://doi.org/10.18502/ijm.v12i1.2517
47.    Proksch, E., pH in nature, humans and skin. The Journal of Dermatology, 2018. 45(9): p. 1044-1052. https://doi.org/10.1111/1346-8138.14489
48.    Garidel, P., C. Hoffmann, and A. Blume, A thermodynamic analysis of the binding interaction between polysorbate 20 and 80 with human serum albumins and immunoglobulins: A contribution to understand colloidal protein stabilisation. Biophysical Chemistry, 2009. 143(1): p. 70-78. https://doi.org/10.1016/j.bpc.2009.04.004
49.    Song, J., et al., Formulation and Evaluation of Celastrol-Loaded Liposomes. Molecules, 2011. 16(9): p. 7880-7892. https://doi.org/10.3390/molecules16097880
50.    Additives, E.P.o.F. and N.S.a.t. Food, Scientific Opinion on the re-evaluation of polyoxyethylene sorbitan monolaurate (E 432), polyoxyethylene sorbitan monooleate (E 433), polyoxyethylene sorbitan monopalmitate (E 434), polyoxyethylene sorbitan monostearate (E 435) and polyoxyethylene sorbitan tristearate (E 436) as food additives. EFSA Journal, 2015. 13(7): p. 4152. https://doi.org/10.2903/j.efsa.2015.4152
Nanomedicine Research Journal
Volume 9, Issue 3
Autumn 2024
Pages 251-263