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http://dx.doi.org/10.20307/nps.2021.27.3.208

𝛽-Patchoulene: Conversion from Patchouli Alcohol by Acid Catalysts and its In silico Anti-inflammatory Study  

Firdaus, Firdaus (Department of Chemistry, Hasanuddin University)
Soekamto, Nunuk Hariani (Department of Chemistry, Hasanuddin University)
Firdausiah, Syadza (Department of Chemistry, Hasanuddin University)
Rasyid, Herlina (Department of Chemistry, Hasanuddin University)
Rifai, Akhmad (Department of Chemical Engineering, Politeknik Negeri Ujung Pandang)
Publication Information
Natural Product Sciences / v.27, no.3, 2021 , pp. 208-215 More about this Journal
Abstract
𝛽-Patchoulene (𝛽-PAE) is a tricyclic sesquiterpene which performed many potential bioactivities and can be found in patchouli oil but in very low concentration. This study aimed to obtained 𝛽-PAE in high concentration by conversion of patchouli alcohol (PA) in patchouli oil under acid catalyzed reaction. Patchouli oil was fractinated by vacuum distillation at 96 kPa to get the fraction with the highest PA content. H2SO4 and ZnCl2 were used respectively as homogeneous and heterogeneous acid catalysts in the conversion reaction of the selected fraction. Patchouli oil, the fractions and the products were analysed by using GC-MS and FTIR instruments. Moreover, the interaction of 𝛽-PAE to COX-2 protein was studied to understand the antiinflammation activity of 𝛽-PAE. The results showed that patchouli oil contains 25.3% of PA. The selected fraction which has the highest PA content (70.3%) was distilled at 151 - 152 ℃. The application of ZnCl2 catalyst in conversion reaction did not succeed. In contrast, H2SO4 as a catalyst in acetic acid solvent succeeded in converting the overall fraction of PA to 𝛽-PAE. Furthermore, the molecular docking study of 𝛽-PAE against COX-2 enzyme showed van der Waals and alkyl-alkyl stacking interactions on ten amino acid residues.
Keywords
${\beta}$-patchoulene; molecular docking; patchouli oil; patchouli alcohol; sulphuric acid catalyst; conversion mechanism;
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1 Hariyani; Widaryanto, E.; Herlina, N. J. Produksi Tanam. 2015, 3, 205-211.
2 Yahya, A.; Yunus, R. M. Procedia Eng. 2013, 53, 1-6.   DOI
3 Kusuma, H. S.; Mahfud, M. Int. Food Res. J. 2017, 24, 1525-1528.
4 Xu, X.; Tang, Z.; Liang, Y. Anal. Methods 2010, 2, 359-367.   DOI
5 Ravindra, N. S.; Ramesh, S. I.; Gupta, M. K.; Jhang, T.; Shukla, A. K.; Darokar, M. P.; Kulkarni, R. N. J. Crop Sci. Biotechnol. 2012, 15, 33-39.   DOI
6 Xian, Y. F.; Li, Y. C.; Ip, S. P.; Lin, Z. X.; Lai, X. P.; Su, Z. R. Exp. Ther. Med. 2011, 2, 545-550.   DOI
7 Chakrapani, P.; Venkatesh, K.; Chandra Sekhar Singh, B.; Arun Jyothi, B.; Kumar, P.; Amareshwari, P.; Roja Rani, A. Int. J. Pharm. Sci. Rev. Res. 2013, 21, 7-15.
8 Chen, W. K.; Tseng, H. H.; Wei, M. C.; Su, E. C.; Chiu, I. C. Int. J. Hydrogen Energy 2014, 39, 19555-19562.   DOI
9 Karimi, A. Adv. Environ. Biol. 2014, 8, 2301-2309.
10 Swamy, M. K.; Sinniah, U. R. Molecule 2015, 20, 8521-8547.   DOI
11 Zhang, Z.; Chen, X.; Chen, H.; Wang, L.; Liang, J.; Luo, D.; Liu, Y.; Yang, H.; Li, Y.; Xie, J.; Su, Z. Eur. J. Pharmacol. 2016, 781, 229-238.   DOI
12 Yang, W. H.; Liu, Y. H.; Liang, J. L.; Lin, Z. X.; Kong, Q. L.; Xian, Y. F.; Guo, D. Q.; Lai, Z. Q.; Su, Z. R.; Huang, X. Q. Eur. J. Inflamm. 2017, 15, 136-141.   DOI
13 Dechayont, B.; Ruamdee, P.; Poonnaimuang, S.; Mokmued, K.; Chunthorng-Orn, J. J. Bot. 2017, 2017, 8310275.
14 Leong, W.; Huang, G.; Khan, I.; Xia, W.; Li, Y.; Liu, Y.; Li, X.; Han, R.; Su, Z.; Hsiao, W. L. W. Front. Pharmacol. 2019, 10, 1229.   DOI
15 Singh, B. R.; Sinha, D. K.; Vinodh Kumar, O. R.; Abhijit, M. P.; Ujjwal Kumar, D. E.; Gupta, V. K. World J. Pharm. Sci. 2019, 7, 47-65.
16 Wu, J. Z.; Liu, Y. H.; Liang, J. L.; Huang, Q. H.; Dou, Y. X.; Nie, J.; Zhuo, J. Y.; Wu, X.; Chen, J. N.; Su, Z. R.; Wu, Q. D. Phytomedicine 2018, 39, 111-118.   DOI
17 Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. J. Comput. Chem. 2009, 30, 2785-2791.   DOI
18 Pettersen, E. F.; Goddard, T. D.; Huang, C. C.; Couch, G. S.; Greenblatt, D. M.; Meng, E. C.; Ferrin, T. E. J. Comput. Chem. 2004, 25, 1605-1612.   DOI
19 Hanwell, M. D.; Curtis, D. E.; Lonie, D. C.; Vandermeersch, T.; Zurek, E.; Hutchison, G. R. J. Cheminform. 2012, 4, 17.   DOI
20 Munda, S.; Dutta, S.; Pandey, S. K.; Sarma, N.; Lal, M. J. Essent. Oil Bearing Plants 2019, 22, 105-119.   DOI
21 Hardjo, P. H.; Susanto, D. P. S.; Savitri, W. D.; Purwanto, M. G. M. Nusant. Biosci. 2019, 11, 123-127.   DOI
22 Miyazawa, M.; Shimabayashi, H.; Hayashi, S.; Hashimoto, S.; Nakamura, S. I.; Kosaka, H.; Kameoka, H. J. Agric. Food Chem. 2000, 48, 5406-5410.   DOI
23 Kusuma, H. S.; Mahfud, M. Period. Polytech. Chem. Eng. 2017, 61, 82-92.
24 Pu, Q.; Liang, J.; Shen, Q.; Fu, J.; Pu, Z.; Liu, J.; Wang, X.; Wang, Q. Genes (Basel) 2019, 10, 441.   DOI
25 Sundaresan, V.; Singh, S. P.; Mishra, A. N.; Shasany, A. K.; Darokar, M. P.; Kalra, A.; Naqvi, A. A. J. Essent. Oil Res. 2009, 21, 220-222.   DOI
26 Ma'mun; Maryadhi, A. Bul. Littro 2008, XIX, 95-99.
27 Asnawi, T. M.; Alam, P. N.; Husin, H.; Zaki, M. IOP Conf. Ser. Mater. Sci. Eng. 2018, 345.
28 Chen, Y.; Wu, Y. G.; Xu, Y.; Zhang, J. F.; Song, X. Q.; Zhu, G. P.; Hu, X. W. Rev. Bras. Farmacogn. 2014, 24, 626-634.   DOI
29 Chen, X. Y.; Dou, Y. X.; Luo, D. D.; Zhang, Z. B.; Li, C. L.; Zeng, H. F.; Su, Z. F.; Xie, J. H.; Lai, X. P.; Li, Y. C. Int. Immunopharmacol. 2017, 50, 270-278.   DOI
30 Hu, G.; Peng, C.; Xie, X.; Zhang, S.; Cao, X. Evid. Based Complement. Altern. Med. 2017, 2017, 4850612.   DOI
31 Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. J. Comput. Chem. 1998, 19, 1639-1662.   DOI
32 Liang, J. L.; Wu, J. Z.; Liu, Y. H.; Zhang, Z. B.; Wu, Q. D.; Chen, H. B.; Huang, Y. F.; Dou, Y. X.; Zhou, J. T.; Su, Z. R.; Zhan, J. Y. X. Mediators Inflamm. 2017, 2017, 1089028.
33 Liu, Y.; Liang, J.; Wu, J.; Chen, H.; Zhang, Z.; Yang, H.; Chen, L.; Chen, H.; Su, Z.; Li, Y. Sci. Rep. 2017, 7, 5591.   DOI
34 Zhang, F. B.; Wang, J. P.; Zhang, H. X.; Fan, G. M.; Cui, X. Exp. Ther. Med. 2019, 17, 3335-3342.
35 Ambrose, D. C. P.; Annamalai, S. J. K.; Naik, R. Indian J. Sci. Technol. 2013, 6, 5559-5562.
36 Su, Z. Q.; Wu, X. L.; Bao, M. J.; Li, C. W.; Kong, S. Z.; Su, Z. R.; Lai, X. P.; Li, Y. C.; Chen, J. N. Trop. J. Pharm. Res. 2014, 13, 359-363.   DOI
37 Dassault Systemes. Biovia Discovery Studio Visualizer; Dassault Systemes: San Diego, 2019.
38 Kusuma, H. S.; Mahfud, M. J. Appl. Res. Med. Aromat. Plants 2017, 4, 46-54.   DOI
39 Lal, M.; Pandey, S. K.; Dutta, S.; Munda, S.; Baruah, J.; Paw, M. J. Essent. Oil Bearing Plants 2018, 21, 131-138.   DOI
40 Bergonzi, M. C.; Bilia, A. R.; Gallori, S.; Guerrini, D.; Vincieri, F. F. Drug Dev. Ind. Pharm. 2001, 27, 491-497.   DOI
41 Cornwell, C. P. J. Essent. Oil Res. 2010, 22, 360-364.   DOI
42 Singh, M.; Sharma, S.; Ramesh, S. Ind. Crops Prod. 2002, 16, 101-107.   DOI
43 Arpi, N.; Erika, C.; Ermaya, D. Proceedings of The Annual International Conference Syiah Kuala University 2011, 2011, 22-27.
44 Muyassaroh.; Daryono, E. D.; Hudha, M. I. Int. J. ChemTech Res. 2016, 9, 108-116.
45 Harunsyah.; Yunus, M. Proc. 2nd Annu. Int. Conf. Syiah Kuala Univ. 2012 8th IMT-GT Uninet Biosci. Conf. 2012, 2, 149-153.
46 Zhao, Z.; Lu, J.; Leung, K.; Chan, C. L.; Jiang, Z. H. Chem. Pharm. Bull (Tokyo). 2005, 53, 856-860.   DOI
47 Swamy, M. K.; Mohanty, S. K.; Sinniah, U. R.; Maniyam, A. J. Essent. Oil Bear. Plants 2015, 18, 826-832.   DOI