SINTESIS DAN KARAKTERISASI BORNEOL DARI α-PINENA GETAH PINUS (Pinus merkusii Jungh. & de Vriese)
Main Article Content
Abstract
Pine resin is obtained from a process of tapping the pine tree (Pinus merkusii Jungh. & de Vriese). After processing, pine
resin will produce gondorukem and turpentine. Currently, the utilization of turpentine is mainly for cosmetic, paint, a mixture of
solvents, antiseptics, and pharmaceuticals. Due to an increase in the added value of the turpentine product, turpentine was
synthesized into borneol. This study aimed to analyze the characteristics of borneol produced from the synthesis of α-pinene using
NaOH and KOH bases. The method was carried out by synthesized α-pinene into borneol through sodium reduction using two
alkali e.i KOH and NaOH. The compounds were characterized by FTIR, NMR and GCMS. The results showed that on
FTIR analysis of 12 samples of the borneol synthesized showed fairly similar absorption peaks with peaks appearing on standard
borneol FTIRs. The NMR analysis of both HNMR and CNMR, compared with the standard NMR compounds α-pinene,
champor and borneol, show that the peaks still show differences. The GCMS result showed the formation of the compound of
borneol compound with the percentage of 0.12 to 2.2% relatives. The type of base and origin of the turpentine used did not show
any difference in borneol yield.
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References
Amilia, N., Siadi, K., & Latifah. (2015). Pengaruh temperatur pada reaksi hidrasi α-pinena menjadi α- terpineol terkatalis zeolit alam teraktivasi. Jurnal MIPA, 38(1), 38–48.
Armaka, M., Papanikolaou, E., Sivropoulou, A., & Arsenakis, M. (1999). Antiviral properties of isoborneol, a potent inhibitor of herpes simplex virus type 1. Antiviral Research, 43, 79–92.
Bao, S., Zhang, D., & Meng, E. (2019). Improving biosynthetic production of pinene through plasmid recombination elimination and pathway optimization. Plasmid 105,1-7 doi: 10.1016/j.plasmid.2019.102431.
Besari, I., Sulistyowati, E., & Ishak, M. (1982). Kimia organik untuk universitas. Bandung: Penerbit ARMICO.
Bhatia, S. P., Letizia, C. S., & Api, A. M. (2008). Fragrance material review on borneol. Food and Chemical Toxicology Journal, 46, 577–580. doi: 10.1016/j.fct.2008.06.031.
Bouzenna, H., Hfaiedh, N., & Giroux-metges, M. (2017). Science direct potential protective effects of alpha-pinene against cytotoxicity caused by aspirin in the IEC-6 cells. Biomedicine et Pharmacotherapy, 93, 961–968. doi: 10.1016/j.biopha.2017.06.031.
Cao, B., Ni, H., Li, J., Zhou, Y., Bian, X., Tao, Y., … Zhu, D. (2017). Biochemical and biophysical research communications (þ) -Borneol suppresses conditioned fear recall and anxiety-like behaviors in mice. Biochemical and Biophysical Research Communications, 1–6. doi: 10.1016/j.bbrc.2017.12.025.
Cao, W., Li, Y., Hou, Y., Yang, M., Fu, X., & Zhao, B. (2019). Biomedicine & pharmacotherapy enhanced anticancer efficiency of doxorubicin against human glioma by natural borneol through triggering ROS-mediated signal. Biomedicine & Pharmacotherapy, 118(July), 109261. doi: 10.1016/ j.biopha. 2019.109261.
Chandra, G., & Murthy, S. S. N. (2018). Dielectric and thermodynamic study of camphor and borneol enantiomers and their binary systems. Thermochimica Acta, 666(241-252) doi: 10.1016/j.tca.2018.04.014
Daryono, E. D. (2015). Sintesis α - pinene menjadi α -terpineol menggunakan katalis h 2 so 4 dengan variasi suhu reaksi dan volume etanol. Jurnal Teknik Kimia USU, 4(2), 1–6.
Diana & Budiman, A. (2018). Asetosilasi terpentin Indonesia menggunakan katalis asam sulfat. Teknoin, 24(1), 21-28.
Dong, T., Chen, N., Ma, X., Wang, J., Wen, J., Xie, Q., & Ma, R. (2018). Biomedicine & pharmacotherapy the protective roles of L- borneolum, D-borneolum and synthetic borneol in cerebral ischaemia via modulation of the neurovascular unit. Biomedicine & Pharmacotherapy, 102(January), 874–883. doi: 10.1016/j.biopha.2018.03.087.
Duke, S. (2005). Phytochemical and ethnobotanical databases. Institute for Traditional Medicine. Dalam Plants containing Borneol. Portland, Oregon. National Agriculture Library. US Department of Agriculture.
Fessenden, R. J., & Fessenden, J. S. (1986). Organic chemistry. (Third Edition). California: Wadsworth, Inc.
Frattini, L., Isaacs, M. A., Parlett, C. M. A., Wilson, K., Kyriakou, G., & Lee, A. F. (2017). Support enhanced alpha pinene isomerization over HPW / SBA-15. “Applied Catalysis B, Environmental,”200, 10–18. doi: 10.1016/j.apcatb.2016.06.064.
Gusmailina. (2015). Review-borneol potensi minyak atsiri masa depan. Prosiding Seminar Nasional Masyarakat Biodiversitas Indonesia, 1(2), 259-264. doi://doi org/ 10.13057/psnmbi/ m010215.
Ho, T., Hung, C., & Shih, T. (2016). Investigation of borneols sold in Taiwan by chiral gas chromatography. Journal of Food and Drug Analysis, 26(1), 348–352. doi: 10.1016/j.jfda. 2016.10.012.
Ho, T., Hung, C., & Shih, T. (2018). Investigation of borneols sold in Taiwan by chiral gas chromatography. Journal of Food and Drug Analysis, 26, 348–352. doi: 10.1016 /j.jfda. 2016.10.012.
Hong, L., Li, X., Bao, Y., Duvall, C. L., Zhang, C., Chen, W., & Peng, C. (2019). Preparation, preliminary pharmacokinetic and brain targeting study of metformin encapsulated W/O/W composite submicron emulsions promoted by borneol Lufeng. European Journal of Pharmaceutical Sciences, 133(160-166) doi: 10.1016/j.ejps.2019.03.019.
Hu, X., Cheng, N., Zhao, J., Piao, X., Yan, Y., Zhang, Q., … Feng, N. (2019). Percutaneous absorption and brain distribution facilitation of borneol on tetramethylpyrazine in a microemulsion-based transdermal thera-peutic system. Asian Journal of Pharmaceutical Sciences, 14(3), 305–312. doi: 10. 1016/j.ajps. 2018.06.003.
Jiang, J., Shen, Y. Y., Li, J., Lin, Y. H., Luo, C. X., & Ya, D. (2015). ( þ ) -Borneol alleviates mechanical hyperalgesia in models of chronic in fl ammatory and neuropathic pain in mice. European Journal of Pharmacology, 757, 53–58. doi: 10.1016/j.ejphar.2015.03.056.
Jin, D., Wang F., & Qu L. (2011). The distribution and expression of claudin-5 and occludin at the rat blood-optic nerve barrier after borneol treatment. Molecular Biology Report, 38, 913–20. doi: 10.1007/s11033-010-0184-1.
Kim, M., Sowndhararajan, K., Jin, S., & Kim, S. (2018). Effect of inhalation of isomers, (+) - α -pinene and (+) - β -pinene on human electroencephalographic activity according to gender di ff erence. European Journal of Integrative Medicine, 17(October 2017), 33–39. doi: 10.1016/j.eujim.2017.11.005.
Li, G., Zhao, H., Hong, J., Quan, K., Yuan, Q., & Wang, X. (2017). Antifungal graphene oxide-borneol composite. Colloids and Surfaces B: Biointerfaces. doi: 10.1016/j.colsur fb.2017. 09.023.
Liang, S-y, Zeng, Y-C, Jiang, Q-q, Wu, J-H, & Wu, Z-z. (2020). Pharmacokinetic studies of multi-bioactive components in rat plasma after oral administration of Xintiantai extract and effects of guide drug borneol on pharmacokinetics. Chinese Herbal Medicines 12(1), 79-87 doi: 10.1016/j.chmed.2019.06. 003.
Liu, Y., Zhao, Y., Guo, D., Liu, W., & Liu, Y. (2017). Synergistic antimicrobial activity of berberine hydrochloride, baicalein and borneol against Candida albicans. Chinese Herbal Medicines, 9(4), 353–357. doi: 10.1016/S1674-63 84(17) 60115-1.
Lo, K., Jurgita, Š., Pa, A., & Raudonien, V. (2018). Influence of plant origin natural α -pinene with different enantiomeric composition on bacteria, yeasts and fungi. Fitoterapia, 127(February), 20–24. doi: 10. 1016/j.fitote. 2018.04.013.
Madhuri, K., & Ramachandra, P. (2017). Ameliorative effect of borneol, a natural bycyclic monoterpene against hyperglycemia, hyperlipidemia and oxidative stress in streptozotocin- induced diabetic Wistar rats. Biomedicine & Pharmacotherapy, 96(August), 336–347. doi: 10.1016/j.biopha. 20 17.09. 122.
Masruri, Rahman, M. F., & Prasosjo, T. I. (2007). Identifikasi dan uji aktivitas antibakteri senyawa volatil terpenoid minyak terpentin. Jurnal Ilmu-Ilmu Hayati (Life Sciences), 19(1), 32–35.
National Institute of Advanced Industrial Science and Technology (AIST), Japan. (2018). Spectral Database for Organic Compounds (SDBS) https://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi, diakses pada tanggal 15 Juni 2020.
Ndongou, F. J., Selka, A., Fabiano-tixier, A., Foucher, D., Clarisse, O., Chemat, F., & Touaibia, M. (2018). Highly selective solvent-free hydrogenation of pinenes toadded-valuecis-pinane. Comptes Rendus - Chimie, 1–8. doi: 10.1016/j.crci.2018.09.002.
Niu, F., Huang, Y., Ji, L., & Liu, J. (2019). Genomic and transcriptional changes in response to pinene tolerance and overproduction in evolved Escherichia coli. Synthetic and Systems Biotechnology, 4(3), 113–119. doi: 10. 1016/j. synbio.2019.05.001.
Pavia, D.L., Kriz, GS., Gary, M., L. (2005). A small scale approach to organic laboratory technique 4th edition. USA: Cengage Learning.
Peng, T. H. X. L. C. (2017). Borneol enhances the antidepressant effects of asiaticoside by promoting its distribution into the brain. Neuroscience Letters. doi: 10.1016/j.neulet. 2017.02.068.
Perum_Perhutani. (2015). Laporan tahunan 2014. Perum Perhutani. Diakses dari http: //www.bumn.go.id/perhutani/halaman/148 pada 25 Juni 2020
Perum Perhutani. (2019). Annual report Perum Per-hutani 2018. Jakarta.
Ponomarev, D., & Mettee, H. (2016). Camphor and its industrial s ynthesis. Chemical Education Journal (CEJ), 18(18), 2–5.
Qi, H., Gao, X., Zhang, L., Wei, S., & Bi, S. (2013). In vitro evaluation of enhancing effect of borneol on transcorneal permeation of compounds with different hydrophilicities and molecular sizes. European Journal of Pharmacology, 705(1–3), 20–25. doi: 10.1016/ j.ejphar.2013.02.031.
Qun-Lin Zhang, Bingmei M. Fu & Zhang-Jin Zhang. (2017) Borneol, a novel agent that improves central nervous system drug delivery by enhancing blood–brain barrier permeability, Drug Delivery, 24,1, 1037-1044. doi: 10.1080 /10717544.2017.1346002
Ren, J., Hu, C., Zhang, Z., Chen, R., Yang, S., Miao, Z., Wang, Y. (2019). Development and validation an LC-MS/MS method to quantify (+)-borneol in rat plasma: Application to a pharmacokinetic study. Journal of Chromatography, B 1109, 121-127 doi: 10.1016 / j.jchromb.2019.01.023.
Ribeiro, C. J. A., Pereira, M. M., Kozhevnikova, E. F., Kozhevnikov, I. V, Gusevskaya, E. V, Kelly, A., & Rocha, S. (2018). Heteropoly acid catalysts in upgrading of biorenewables : Synthesis of para - menthenic fragrance compounds from α -pinene oxide. Catalysis Today, (May), 0–1. doi: 10.1016/j.cattod. 2018.12.023.
Roma’n-Aguirre, M., Gochi, Y. P., Sanchez, A. R., Torre, L. de la, & Aguilar-Elguezabal, A. (2008). Synthesis of camphene from a -pinene using SO 32 À functionalized MCM-41 as catalyst. Synthesis of Camphene from a-Pinene Using SO3 2 Functionalized MCM-41 as Catalyst, 334, 59–64. doi: 10.1016/ j.apcata. 2007.09.031.
Sánchez-velandia, J. E., Gelves, J., Dorkis, L., Márquez, M., & Villa, A. (2019). Microporous and mesoporous materials ring-opening of β-pinene epoxide into high-added value products over Colombian natural zeolite. Microporous and Mesoporous Materials, 287(December 2018), 114–123. doi: 10.1016 /j.micromeso.2019.05.053.
Shanghe, C., Meyu, J., & Xing, H. (2010). Application of B/ Ti-based composite catalyst in synthetic borneol production. Biomass Chemical Engineering, 44(3), 5–8.
Wang, L., Liang, Q., Lin, A., Wu, Y., Min, H., Song, S., Gao, Q. (2019). Borneol alleviates brain injury in sepsis mice by blocking neuronal effect of endotoxin. Life Sciences, 232(March), 116647. doi: 10.1016/j.lfs.2019. 116647.
Wiyono, B., Tachibana, S., & Tinambunan, D. (2006). Chemical composition of Indonesian Pinus merkusii turpentine oil, gum oleoresins and resins from Sumatra and Java. Pakistan Journal of Biological Sciences, 9(1), 7–14.
Wu, J., Wang, L., Chen, X., Wei, X., Liang, J., & Yao, G. (2019). Thermochimica acta measurement and correlation of vapor – liquid equilibrium data for binary cymene , and α-pinene at 101.33 kPa. Thermochimica Acta, 679(June), 178318. doi: 10.1016/j.tca.2019.178318.
Zhang, Q-L., Fu, B.M & Zhang, Z-J (2017). Borneol, a novel agent that improves central nervous system drug delivery by enhancing blood–brain barrier permeability. Drug Delivery, 24(1), 1037-1044. doi: 10.1080/10717544. 2017.1346002.
