Aporphine alkaloids from piper erecticaule and acetylcholinesterase inhibitory activity

Wan Mohd Nuzul Hakimi Wan Salleh

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Type :	article
Subject :	Q Science (General)
Main Author :	Wan Mohd Nuzul Hakimi Wan Salleh
Additional Authors :	Norkamilah Abdullah Nur Athirah Hashim Heng, Yen Khong Shamsul Khamis
Title :	Aporphine alkaloids from piper erecticaule and acetylcholinesterase inhibitory activity

Place of Production :	Tanjong Malim
Publisher :	Fakulti Sains dan Matematik
Year of Publication :	2019
Corporate Name :	Universiti Pendidikan Sultan Idris
PDF Full Text :	Login required to access this item.

Abstract : Universiti Pendidikan Sultan Idris

Chemical constituents and biological activities of the aerial parts of Piper erecticaule C.DC. have been studied for the first time. Fractionation and purification of the extracts afforded aristolactam AII (1), aristolactam BII (2), piperolactam A (3), piperolactam C (4),piperolactam D (5), together with terpenoids of β-sitosterol, β-sitostenone, taraxerol, and lupeol. The structures of these compounds were obtained by analysis of their spectroscopic data, as well as the comparison with that of reported data. Acetylcholinesterase inhibitory activity revealed that compounds 1 and 3 showed strong AChE inhibitory effects with the percentage inhibition of 75.8% and 74.8%, respectively

References

1. Amin SA, Bhattacharya P, Basak S, Gayen S, Nandy A, Saha, A. 2017. Pharmacoinformatics study of Piperolactam A from Piper betle root as the new lead for nonsteroidal anti fertility drug development. Comput Biol Chem 67:213 - 224. https://doi.org/10.1016/j.compbiolchem.2017.01.004

2. Chen Y, Chen JC, Chang Y, Teng C, Lin W, Wu C, Chen, I. 2004. A new aristolactam alkaloid and anti-platelet aggregation constituents from Piper taiwanense. Planta Med 70: 174 - 177. https://doi.org/10.1055/s-2004-815497

3. Ee GCL, Lim SK, Lim CM, Dzulkefly K. 2008. Alkaloids and carboxylic acids from Piper nigrum. Asian J Chem 20: 5931 - 5940.

4. Kato MJ, Furlan M. 2007. Chemistry and evolution of Piperaceae. Pure Appl Chem 79: 529 -538. https://doi.org/10.1351/pac200779040529

5. Kim SR, Sung SH, Kang SY, Koo KA, Kim SH, Ma CJ, Lee HS, Park MJ, Kim YC. 2004. Aristolactam BII of Saururus chinensis attenuates glutamate-induced neurotoxicity in rat cortical cultures probably by inhibiting nitric oxide production. Planta Med 70: 391-396. https://doi.org/10.1055/s-2004-818964

6. Kumar V, Poonam, Prasad AK, Parmar VS. 2003. Naturally occurring aristolactams, aristolochic acids, and dioxoaporphines and their biological activities. Nat Prod Rep 20: 565 - 583. https://doi.org/10.1039/b303648k

7. Levrier C, Balastrier M, Beattie KD, Carroll AR, Martin F, Choomuenwai V, Davis RA. 2013. Pyridocoumarin, aristolactam, and aporphine alkaloids from the Australian rainforest plant Goniothalamus australis. Phytochemistry 86: 121 - 126. https://doi.org/10.1016/j.phytochem.2012.09.019

8. Lin CF, Hwang TL, Chien CC, Tu HY, Lay HL. 2013. A new hydroxychavicol dimer from the roots of Piper betle. Molecules 18: 2563-2570. https://doi.org/10.3390/molecules18032563

9. Loizzo MR, Tundis R, Menichini F. Menichini F. 2008. Natural products and their derivatives as cholinesterase inhibitors in the treatment of neurodegenerative disorders: an update. Curr Med Chem 15: 1209 - 1228. https://doi.org/10.2174/092986708784310422

10. Michle J, Ingrouille MJ, Simmonds MSJ, Heinrich M. 2014. Naturally occurring aristolochic acid analogues and their toxicities. Nat Prod Rep 31: 676 - 693. https://doi.org/10.1039/c3np70114j

11. Park SY. 2010. Potential therapeutic agents against Alzheimer’s disease from natural sources. Arch Pharm Res 33: 1589 - 1609. https://doi.org/10.1007/s12272-010-1010-y

12. Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE, Boll PM. 1997. Phytochemistry of the genus Piper. Phytochemistry 46: 597 - 673. https://doi.org/10.1016/S0031-9422(97)00328-2

13. Salleh WMNHW, Ahmad F, Khong HY. 2014a. Chemical compositions and antimicrobial activity of the essential oils of Piper abbreviatum, P. erecticaule and P. lanatum (Piperaceae). Nat Prod Comm 9: 1795 - 1798.

14. Salleh WMNHW, Hashim NA, Ahmad F, Khong HY. 2014b. Anticholinesterase and antityrosinase activities of ten Piper species from Malaysia. Adv Pharm Bull 4: 527-531. https://doi.org/10.5681/apb.2014.078

15. Salleh WMNHW, Ahmad F, Khong HY. 2014c. Antioxidant and anti-tyrosinase activities from Piper officinarum C.DC (Piperaceae). JAppl Pharm Sci 4: 87 - 91. https://doi.org/10.7324/JAPS.2014.40516

16. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM, Chen JJ, Nahar L, Wansi JD, Sarker SD. 2016a. Beilschglabrines A and B: Two new bioactive phenanthrene alkaloids from the stem bark of Beilschmiedia glabra. Phytochem Lett 16: 192 - 196. https://doi.org/10.1016/j.phytol.2016.04.013

17. Salleh WMNHW, Ahmad F, Khong HY, Zulkifli RM, Sarker SD. 2016b. Madangones A and B: Two new neolignans from the stem bark of Beilschmiedia madang and their bioactivities. Phytochem Lett 15: 168 - 173. https://doi.org/10.1016/j.phytol.2016.01.004

18. Tawan CS, Ipor IB, Fasihuddin BA, Sani H. 2002. A brief account on the wild Piper (Piperaceae) of the Crocker Range, Sabah. ASEAN Review of Biodiversity and Environmental Conservation (ARBEC), Universiti Malaysia Sarawak.

19. Tsai IL, Lee FP, Wu CC, Duh CY, Ishikawa T, Chen JJ, Chen YC, Seki H, Chen IS. 2005. New cytotoxic cyclobutanoid amides, a new furanoid lignan and anti-platelet aggregation constituents from Piper arborescens. Planta Med 71: 535 - 542. https://doi.org/10.1055/s-2005-864155

20. Zhang YN, Zhong XG, Zheng ZP, Hu XD, Zuo JP, Hu LH. 2007. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr. Bioorg Med Chem 15: 988 - 996. https://doi.org/10.1016/j.bmc.2006.10.034

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