α-MANGOSTIN/CLOVE OIL-INCORPORATED LAURIC ACID-BASED SOLVENT REMOVAL-INDUCED IN SITU FORMING MATRICES

Authors

  • Jongjan Mahadlek
  • Thawatchai Phaechamud
  • Prapansak Toungsuwan

DOI:

https://doi.org/10.55766/sujst-2023-05-e02594

Keywords:

α-mangostin, clove oil, in situ forming matrices, lauric acid, solvent removal

Abstract

Typically, the bacteria in periodontal pocket of periodontitis disease are capable of producing a number of virulence factors, which are directly toxic to host tissues or immune cells, or indirectly damage host tissues via induction of inflammatory cytokines. The eradication of these microbes from periodontal pocket is one of crucial processes of periodontitis treatment.  The α-mangostin from Garcinia mangostana Linn has the most potent antibacterial activity with less tendency to acquire resistance; therefore, it is interesting for using as active compound for periodontitis treatment. This study focuses on the development of in situ forming matrices (ISM) involving 50% w/w lauric acid, 5% w/w clove oil and different α-mangostin amount in NMP for periodontal drug delivery. Physicochemical properties of ISM were investigated including pH, density, viscosity, surface tension, in vitro matrix formation, and injectability. Antimicrobial activities of formulated ISM against three standard microbes were evaluated using agar cup diffusion methods. The pH and density of all α-mangostin and clove oil-loaded 50% w/w lauric acid matrices was 4.40 ± 0.04 to 4.78 ± 0.20 and 0.960 ± 0.000 to 0.963 ± 0.001 g/cm3, respectively. The increasing α-mangostin amounts significantly increased the viscosity of prepared formulation and injection force. All formulations had low viscosity that it was easy to injection and spreadable in the periodontal pockets. After contact PBS pH 6.8, they transformed as matrix and the hydrophobic manner of clove oil retarded a solvent exchange. These prepared formulations showed the antimicrobial activities against Staphylococcus aureus ATCC 6538, Escherichia coli ATCC 25922, and Candida albicans ATCC 17011. Hence, they are the potential systems for periodontal drug delivery.

References

Al-Massarani, S.M., El-Gamal, A.A., Al-Musayeib, N.M., Mothana, R.A., Basudan, O.A., Al-Rehaily, A.J., Farag, M., Assaf, M.H., El-Tahir, K.H., and Maes, L. (2013). Phytochemical, antimicrobial and antiprotozoal evaluation of Garcinia mangostana pericarp and α-mangostin, its major xanthone derivative. Molecules, 18(9):10,599-10,608. https://doi.org/10.3390/molecules180910599

Chantadee, T., Lertsuphovanit, N., and Phaechamud, T. (2019a). Application of fatty acid for pharmaceuticals. Thai Bulletin of Pharmaceutical Sciences, 14:1-11.

Chantadee, T., Santimaleeworagun, W., Phorom, Y., and Phaechamud, T. (2020). Saturated fatty acid-based in situ forming matrices for localized antimicrobial delivery. Pharmaceutics, 12(9):808. https://doi.org/10.3390/pharmaceutics12090808

Chantadee, T., Santimaleeworagun, W., Phorom, Y., and Phaechmud, T. (2019b). Mixed solvent-lauric acid solvent-exchange induced in situ forming gel. Key Eng Mater, 819:195-201. https://doi.org/10.4028/www.scientific.net/KEM.819.195

Fei, X., Jo, M., Lee, B., Han, S.B., Lee, K., Jung, J.K., Seo, S.Y., and Kwak, Y.S. (2014). Synthesis of xanthone derivatives based on α-mangostin and their biological evaluation for anti-cancer agents. Bioorganic and Medicinal Chemistry Letters, 24(9):2062-2065. https://doi.org/10.1016/j.bmcl.2014.03.047.

Ghasemzadeh, A., Jaafar, H.Z.E., Baghdadi, A., and Tayebi-Meigooni, A. (2018). Alpha-mangostin-rich extracts from mangosteen pericarp: optimization of green extraction protocol and evaluation of biological activity. Molecules, 23(8):1852. https://doi.org/10.3390/molecules23081852

Ibrahim, M.Y., Hashim, N.M., Mariod, A.A., Mohan, S., Abdulla, M.A., Abdelwahab, S.I., and Arbab, I.A. (2014). α-Mangostin from Garcinia mangostana Linn: An updated review of its pharmacological properties. Arabian Journal of Chemistry, 9(3):317-329. https://doi.org/10.1016/j.arabjc.2014.02.011

Kahwaji, S., Johnson, M.B., Kheirabadi, A.C., Groulx, D., and White, M.A. (2017). Fatty acids and related phase change materials for reliable thermal energy storage at moderate temperatures. Solar Energy Materials and Solar Cells, 167:109-120. https://doi.org/10.1016/j.solmat.2017.03.038

Kheawfu, K., Pikulkaew, S., Rades, T., Müllertz, A., Gersdorff, L.V., Jørgensen, L., and Okonogi, S. (2021). Design and optimization of self-nanoemulsifying drug delivery systems of clove oil for efficacy enhancement in fish anesthesia. Journal of Drug Delivery Science and Technology, 61:102241. https://doi.org/10.1016/j.jddst.2020.102241

Li, G.L., Zheng, L.Q., and Xiao, J.X. (2009). Synthesis and surface activities of organic solvent-soluble fluorinated surfactants. Journal of Fluorine Chemistry, 130(7):674-681. https://doi.org/10.1016/j.jfluchem.2009.05.006

Mei, L., Huang, X., Xie, Y., Chen, J., Huang, Y., Wang, B., Wang, H., Pan, X., and Wu, C. (2017). An injectable in situ gel with cubic and hexagonal nanostructures for local treatment of chronic periodontitis. Drug Delivery, 24(1):1,148-1,158. https://doi.org/10.1080/10717544.2017.1359703

Narasimhan, S., Maheshwaran, S., Abu-Yousef, I.A., Majdalawieh, A.F., Rethavathi, J., Das, P.E., and Poltronieri, P. (2017). Anti-bacterial and anti-fungal activity of xanthones obtained via semi-synthetic modification of α-mangostin from Garcinia mangostana. Molecules, 22(2):275. https://doi.org/10.3390/molecules22020275

Nisar, T., Yang, X., Alim, A., Iqbal, M., Wang, Z.C., and Guo, Y. (2019). Physicochemical responses and microbiological changes of bream (Megalobrama ambycephala) to pectin based coatings enriched with clove essential oil during refrigeration. International Journal of Biological Macromolecules, 124:1,156-1,166. https://doi.org/10.1016/j.ijbiomac.2018.12.005

Ovalle-Magallanes, B., Eugenio-Pérez, D., and Pedraza-Chaverri, J. (2017). Medicinal properties of mangosteen (Garcinia mangostana L.): A comprehensive update. Food and Chemical Toxicology, 109(1):102-122.

Phaechamud, T. and Setthajindalert, O. (2018). Antimicrobial in-situ forming gels based on bleached shellac and different solvents. Journal of Drug Delivery Science and Technology, 46:285-293. https://doi.org/10.1016/j.jddst.2018.05.035

Phaechamud, T., Thurein, S.M., and Chantadee, T. (2018). Role of clove oil in solvent exchange-induced doxycycline hyclate-loaded Eudragit RS in situ forming gel. Asian Journal of Pharmaceutical Sciences, 13(2):131-142. https://doi.org/10.1016/j.ajps.2017.09.004

Phitaktim, S., Chomnawang, M., Sirichaiwetchakoon, K., Dunkhunthod, B., Hobbs, G., and Eumkeb, G. (2016). Synergism and the mechanism of action of the combination of α-mangostin isolated from Garcinia mangostana L. And oxacillin against an oxacillin- resistant Staphylococcus saprophyticus. BMC Microbiology, 16(1): 195. https://doi.org/10.1186/s12866-016-0814-4

Rungseevijitprapa, W. and Bodmeier, R. (2009). Injectability of biodegradable in situ forming microparticle systems (ISM). European Journal of Pharmaceutical Sciences, 36(4-5):524-531. https://doi.org/10.1016/j.ejps.2008.12.003

Sanghvi, R., Narazaki, R., Machatha, S.G., Yalkowsky, S.H. (2008). Solubility improvement of drugs using N-methyl pyrrolidone. AAPS PharmSciTech, 9(2):366-376. https://doi.org/10.1208/s12249-008-9050-z

Senarat, S., Chantadee, T., Santimaleeworagun, W., Phorom, Y., and Phaechamud, T. (2019). Alpha-mangostin phase inversion induced in situ forming gel. Key Engineering Materials, 819:202-208. https://doi.org/10.4028/www.scientific.net/KEM.819.202

Shuai, C., Yang, W., Feng, P., Peng, S., and Pan, H. (2020). Accelerated degradation of HAP/PLLA bone scaffold by PGA blending facilitates bioactivity and osteoconductivity. Bioactive Materials, 6(2):490-502. https://doi.org/10.1016/j.bioactmat.2020.09.001

Sivaranjani, M., Leskinen, K., Aravindraja, C., Saavalainen, P., Pandian, S.K., Skurnik, M., and Ravi, A.V. (2019). Deciphering the antibacterial mode of action of alpha-mangostin on Staphylococcus epidermidis RP62A through an integrated transcriptomic and proteomic approach. Frontiers in Microbiology, 10:150. https://doi.org/10.3389/fmicb.2019.00150

Thakur, R.R., McMillan, H.L., and Jones, D.S. (2014). Solvent induced phase inversion-based in situ forming controlled release drug delivery implants. Journal of Controlled Release, 176:8-23. https://doi.org/10.1016/j.jconrel.2013.12.020

Torrungruang, K., Vichienroj, P., and Chutimaworapan, S. (2007). Antibacterial activity of mangosteen pericarp extract against periodontal pathogens. Journal of the Dental Association of Thailand, 57(5):240-246.

Walker, C.B., Karpinia, K., and Baehni, P. (2004). Chemotherapeutics: antibiotics and other antimicrobials. Periodontology 2000, 36(1):146-165. https://doi.org/10.1111/j.1600-0757.2004.03677.x

Yiemwattana, I. and Kaomongkolgit, R. (2015). Alpha-mangostin suppresses IL-6 and IL-8 expression in P. gingivalis LPS-stimulated human gingival fibroblasts. Odontol, 103(3):348-355. https://doi.org/10.1007/s10266-014-0160-7

Zou, H., Koh, J.J., Li, J., Qiu, S., Aung, T.T., Lin, H., Lakshminarayanan, R., Dai, X., Tang, C., Lim, F.H., Zhou, L., Tan, A.L., Verma, C., Tan, D.T.H., Chan, H.S.O., Saraswathi, P., Cao, D., Liu, S., and Beuerman, R.W. (2013). Design and synthesis of amphiphilic xanthone-based, membrane-targeting antimicrobials with improved membrane selectivity. Journal of Medicinal Chemistry, 56(6):2,359-2,373. https://doi.org/10.1021/jm301683j

Downloads

Published

2023-11-15

How to Cite

Mahadlek, J., Phaechamud, T., & Toungsuwan, P. (2023). α-MANGOSTIN/CLOVE OIL-INCORPORATED LAURIC ACID-BASED SOLVENT REMOVAL-INDUCED IN SITU FORMING MATRICES. Suranaree Journal of Science and Technology, 30(5), 030136(1–7). https://doi.org/10.55766/sujst-2023-05-e02594

Issue

Section

Research Article

Categories