Andy Suryadi, Siswandono Siswodihardjo, Tri Widiandani, Retno Widyowati
Andy Suryadi1,3, Siswandono Siswodihardjo2, Tri Widiandani2, Retno Widyowati2*
1Department of Pharmacy, Faculty of Sports and Health, Gorontalo State University, Gorontalo 96128 Indonesia.
2Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Nanizar Zaman Joenoes Building, Campus C UNAIR, Mulyorejo, Surabaya 60115, Indonesia.
3Department of Pharmacognosy and Phytochemistry, Faculty of Pharmacy, Universitas Airlangga, Nanizar Zaman Joenoes Building, Campus C UNAIR, Mulyorejo, Surabaya 60115 Indonesia.
Volume - 14,
Issue - 4,
Year - 2021
Temu kunci (Boesenbergia pandurata ROXB. SCHLECHT) is one of Indonesia medicinal plants which contains essential oils and flavonoids and it has interesting pharmacological activities, such as antifungal, antibacterial, antioxidant, anti-inflammatory and anti-cancer. It also contains pinostrobin which potent as anti-inflammatory and analgesic activities through inhibition of COX-2 enzymes. This research was to obtain pinostrobin derivatives of acylation reactions between pinostrobin and acyl chloride derivatives. The structure modifications of pinostrobin were obtained by Schotten-Baumann method through nucleophilic substitution reactions between pinostrobin and acyl chloride derivatives. Their structure had analyzed using the spectrophotometric analysis (NMR, IR, and GC/MS). The investigation of structure modifications of pinostrobin (1) from this plant has demonstrated the presence of pinostrobin acetate (2) and new pinostrobin propionate (3). The 2 and 3 are derivatives of pinostrobin that can be synthesized using the Schotten-Baumann method to yield 84.3% and 73.9%, respectively. The results of in silico study between pinostrobin and pinostrobin acyl derivatives on the COX-2 receptor with a PDB code: 1PXX showed that pinostrobin RS value was -87.18kcal/mol, while pinostrobin propionate had a RS value of -98.61 kcal/mol. It can be predicted that the pinostrobin acyl derivative has greater analgesic activity than pinostrobin, so it is feasible to be developed and carried out research on its analgesic activity in vivo.
Cite this article:
Andy Suryadi, Siswandono Siswodihardjo, Tri Widiandani, Retno Widyowati. Structure Modifications of Pinostrobin from Temu Kunci (Boesenbergia pandurata ROXB. SCHLECHT) and Their Analgesic Activity Based on in Silico Studies. Research Journal of Pharmacy and Technology. 2021; 14(4):2089-4. doi: 10.52711/0974-360X.2021.00370
Andy Suryadi, Siswandono Siswodihardjo, Tri Widiandani, Retno Widyowati. Structure Modifications of Pinostrobin from Temu Kunci (Boesenbergia pandurata ROXB. SCHLECHT) and Their Analgesic Activity Based on in Silico Studies. Research Journal of Pharmacy and Technology. 2021; 14(4):2089-4. doi: 10.52711/0974-360X.2021.00370 Available on: https://rjptonline.org/AbstractView.aspx?PID=2021-14-4-46
1. Siswandono and Soekardjo B. Kimia Medisinal: Metode modifikasi struktur molekul obat dalam. Ed. 2. Surabaya: Airlangga University Press. 2016.
2. Fathima MZ, Shanmugarajan TS, Kumar SS and Yadav BVN. Comparative in silico docking studies of Hinokitiol with Sorafenib and Nilotinib against Proto-Oncogene Tyrosine-Protein Kinase (ABL1) and Mitogen-activated Protein Kinase (MAPK) to target hepatocellular C. Research Journal of Pharmacy and Technology. 2017; 10(1): 257–262.
3. Hyun JM, Mee HK, Hoonjoeng K, Jaeng-kwa H and Hasan M. Induction of apoptosis and cell cycle arrest by a chalcone Panduratin A isolated from Kaempferia rotunda in androgen independent human prostat cancer cells PC3 and DU145. Carcinogenesis. 2006; 27: 1454–64.
4. Karyantini VADW. Senyawa penanda analitik dari rimpang temu kunci (Boesenbergia pandurata (Roxb.) Schlecht), Yogyakarta: Universitas Gadjah Mada. 2008.
5. Fadilah F, Wiyono L, Edina BC, Rahmawati RA, Erlina L, Tedjo A and Paramita RI. In silico study and in vitro test of extract Kaempferia pandurata Roxb. as anti ER (+) breast cancer cell line MCF-7. Research Journal of Pharmacy and Technology. 2019; 12(5): 2391–2395.
6. Patel NK and Bhutani KK. Pinostrobin and Cajanus lactone isolated from Cajanus cajan (L.) leaves inhibits TNF-α and IL-1β production: in vitro and in vivo experimentation. Phytomedicine. 2014; 21(7): 946–53.
7. Gomez BI, Benjumea D, Patino A, Jimenez N and Osorio E. Inhibition of the toxic effects of Bothrops asper venom by pinostrobin, a flavanone isolated from Renealmia alpinia (Rottb.) MAAS. J. Ethnopharmacol. 2014; 155(3), 1609–15.
8. Lewis WH and Elvin-Lewis MPF. Medical Botany: Plant Affecting Human Health, Denver: John Willey and Sons. 2003.
9. Hinz B, Dormann H and Brune K. More pronounced inhibition of cyclooxygenase 2, increase in blood pressure, and reduction of heart rate by treatment with diclofenac compared with celecoxib and rofecoxib. Arthritis Rheum. 2006; 54(1): 282–291.
10. Otera J. Esterification methods, reactions, and applications. Weinheim: Wiley-VCH. 2003.
11. Gilles V, Vieira MA, Lacerda JV, Castro EVR, Santos RB, Orestes E, Carneiro JWM and Greco SJ. A new, simple and efficient method of Steglich esterification of Juglone with long-chain fatty acids: Synthesis of a new class of non-polymeric wax deposition inhibitors for crude oil. J. Braz. Chem. Suc. 2015; 26(1): 74–83.
12. Clayden J, Greeves N, Warren S and Wothers P. Organic Chemistry. New York: Oxford University Press. 2005.
13. Zubrich JW. The organic chem lab survival manual: A student guide to techniques. Denver: John Wiley & Sons Ltd p. 88-95. 2011.
14. Buvana C, Sumathy A and Sukumar M. In silico identification of potential xanthine oxidase inhibitors for the treatment of gout and cardiovascular disease. Asian Journal of Research in Chemistry. 2013 6(11): 1049–1053.
15. Rani V and Lal N. In silico drug designing for jaundice. Research Journal of Science and Technology. 2017; 9(1): 155–159.
16. Hemalatha K, Selvin J and Girija K. Synthesis, In silico molecular docking study and anti-bacterial evaluation of some novel 4-anilino quina. Asian Journal of Pharmaceutical Research. 2018; 8(3): 125–132.
17. Otuokere IE, Amaku FJ and Alisa CO. In silico geometry optimization, excited – state properties of (2E)-N-hydroxy-3-[3-(phenylsulfamoyl) phenyl] prop-2-enamide (belinostat) and its molecular docking studies with ebola virus glycoprotein. Asian Journal of Pharmaceutical Research. 2015; 5(3): 131–137.
18. Meeran SB, Subburaya U and Narasimhan G. In Silico and In Vitro Screening of Ethanolic Extract of Fruits of Withania Coagulans against Diabetes. Research Journal of Pharmacy and Technology. 2020; 13(2): 631–635.
19. Zadorozhnii PV, Kiselev VV, Teslenko NO, Kharchenko AV, Pokotylo IO, Okhtina OV and Kryshchyk OV. In silico prediction and molecular docking studies of N-Amidoalkylated derivatives of 1,3,4-Oxadiazole as COX-1 and COX-2 potential inhibitors. Research Journal of Pharmacy and Technology. 2017; 10(11): 3957–3963.
20. Chinchole PP and Wankhede SB. Comparative in silico drug likeness and in vitro study of some Schiff’s bases as potent COX-II Inhibitors. Research Journal of Pharmacy and Technology. 2019; 12(10): 4973–4980.
21. Bitencourt-Ferreira G and de Azevedo WF. Molegro virtual docker for docking. Methods Mol. Biol. 2019; 2053: 149–167.
22. Kiefer JR, Rowlinson SW, Prusakiewicz JJ, Pawlitz JL, Kozak KR, Kalgutkar AS, Stallings WC, Marnett LJ and Kurumbail RG. Crystal structure of diclofenac bound to the cyclooxygenase active site of COX-2. PDB Deposition. 2003.
23. Bhasker S, Sandeep G and Ranganath YS. Future of cancer therapy-COX-2 inhibitors: A review. Research Journal of Pharmacy and Technology. 2009; 2(4): 617–620.
24. Kumaresan GD and Dhanraj M. Efficacy of Cox-2 inhibitors in the clinical management of TMJ arthritis: A review. Research Journal of Pharmacy and Technology. 2017; 10(12): 4439–44441.