UPSI Digital Repository (UDRep)
Start | FAQ | About

QR Code Link :

Type :article
Subject :Q Science (General)
Main Author :Wan Mohd Nuzul Hakimi Wan Salleh
Additional Authors :Nur Athirah Hashim
Farediah Ahmad
Shamsul Khamis
Title :Phytochemicals and tyrosinase inhibitory activity from piper caninum and piper magnibaccum
Place of Production :Tanjong Malim
Publisher :Fakulti Sains dan Matematik
Year of Publication :2019
Corporate Name :Universiti Pendidikan Sultan Idris
PDF Guest :Click to view PDF file

Abstract : Universiti Pendidikan Sultan Idris
Background: Piper species are aromatic plants used as spices in the kitchen, but their secondary metabolites have also shown biological effects on human health. In traditional medicine, Piper species have been used worldwide to treat several diseases such as urological problems, skin, liver and stomach ailments, for wound healing, and as antipyretic and anti-inflammatory agents. In the present study, we attempted to isolate the phytochemicals from Piper caninum and Piper magnibaccum and evaluate their tyrosinase inhibitory activity. Methods: Phytochemical constituents of the extract were investigated using various chromatographic and spectroscopic methods. The structures of the isolated phytochemicals were established by analysis of their spectroscopic data, as compared to that of reported data. Tyrosinase inhibitory activity was also tested on the extracts and selected compounds using mushroom tyrosinase as the enzyme. Results: Fractionation and purification of the extracts of Piper caninum and Piper magnibaccum afforded nine known compounds which are cepharanone A (1), cepharadione A (2), aristolactam AII (3), 5,7-dimethoxyflavone (4), 24-methylenecycloartan-3-one (5), βsitosterol (6), piperumbellactam A (7), 24S-ethylcholesta-5,22,25-trien-3β-ol (8) and stigmast-3,6-dione (9). Ethyl acetate extracts from leaves of P. magnibaccum gave the highest inhibition value at 48.35%, while the tested compounds displayed weak tyrosinase activity compared to the positive control, kojic acid. Conclusion: These phytochemical results suggest that the extracts could assist as a potential source of bioactive compounds. Further research is needed in which the extract could possibly be exploited for pharmaceutical use.

References

1. Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, et al. Phytochemistry of the genus Piper. Phytochemistry. 1997;46(4):597-673. doi:10.1016/S0031-9422(97)00328-2

2. Wu QL, Wang SP, Tu GZ, Feng YX, Yang JS. Alkaloids from Piper puberullum. Phytochemistry. 1997;44(4):727-30. doi:10.1016/S0031-9422(96)00585-7

3. Prabhu BR, Mulchandani NB. Lignans from Piper cubeba. Phytochemistry. 1985;24(2):329-31. doi:10.1016/s0031-9422(00)83546-3

4. Salleh WM, Kamil F, Ahmad F, Sirat HM. Antioxidant and anti-inflammatory activities of essential oil and extracts of Piper miniatum. Nat Prod Commun. 2015;10(11):2005-2008. doi:10.1177/193 4578x1501001151

5. Bodiwala HS, Singh G, Singh R, Dey CS, Sharma SS, Bhutani KK, et al. Antileishmanial amides and lignans from Piper cubeba and Piper retrofractum. J Nat Med.2007;61(4):418-21. doi:10.1007/s11418-007-0159-2

6. Salleh WM, Hashim NA, Ahmad F, Khong HY. Anticholinesterase and antityrosinase activities of ten Piper species from Malaysia. Adv Pharm Bull. 2014;4(2):527-31. doi:10.5681/apb.2014.078

7. Salleh WM, Ahmad F, Khong HY. Evaluation of antioxidant, anticholinesterase and antityrosinase activities of five Cinnamomum species. Dhaka Univ J Pharm Sci. 2016;14(2):125-32. doi:10.3329/dujps.v 14i2.28500

8. Salleh WM, Ahmad F, Khong HY. Chemical constituents from Piper caninum and antibacterial activity. J Appl Pharm Sci. 2015;5(6):20-5. doi:10.7324/JAPS.2015.50604

9. Ahmad F, Jamil S, Read RW. Isobutylamides from Piper ridleyi. Phytochemistry. 1995;40(4):1163-5. doi:10.1016/0031-9422(95)92654-Q

10. Setzer WN, Setzer MC, Bates RB, Nakkiew P, Jackes BR, Chen L, et al. Antibacterial hydroxycinnamic esters from Piper caninum from Paluma, North Queensland, Australia: The crystal and molecular structure of (+)-bornyl coumarate. Planta Med. 1999;65(8):747-9. doi:10.1055/s-2006-960855

11. Ma J, Jones SH, Hecht SM. Phenolic acid amides: A new type of DNA strand scission agent from Piper caninum. Bioorg Med Chem. 2004;12(14):3885-9. doi:10.1016/j.bmc.2004.05.007

12. Ma J, Jones HS, Marshall R, Johnson RK, Hecht SM. A DNA damaging oxoaporphine alkaloid from Piper caninum. J Nat Prod. 2004;67(7):1162-4. doi:10.1021/np040056x

13. Suwanphakdee C, Masuthon S, Chantaranothai P, Chayamarit K, Chansuvanich N. Notes on the genus Piper L. (Piperaceae) in Thailand. Thai For Bull. 2006;34:206-14.

14. Ahmad F, Sohana AB, Roger RW. Benzofurans from the leaves of Piper magnibacum C.DC. ACGC Chem Res Commun. 1998;7:33-7.

15. Emrizal, Ahmad F, Sirat HM, Jamaludin F, Mustapha NM, Ali RM, et al. Anti- inflammatory activity of Piper magnibaccum (Piperaceae). Nat Prod Commun. 2008;3(10):1719-21.

16. Salleh WM, Ahmad F. Preliminary investigations of antioxidant, antityrosinase, acetylcholinesterase and anti-inflammatory activities of Actinodaphne species. Marmara Pharm J. 2016;20(2):137-43. doi:10.12991/mpj.20162048388

17. Salleh WM, Sazali NS, Ahmad F, Taher M. Biflavonoids from the leaves and stem bark of Garcinia griffithii and their biological activities. Marmara Pharm J. 2017;21(4):889-97. doi:10.12991/ mpj.2017.27

18. Tang GH, Chen DM, Qiu BY, Sheng L, Wang YH, Hu GW, et al. Cytotoxic amide alkaloids from Piper boehmeriaefolium. J Nat Prod. 2011;74(1):45-9. doi:10.1021/np100606u

19. Lin CF, Hwang TL, Chien CC, Tu HY, Lay HL. A new hydroxychavicol dimer from the roots of Piper betle. Molecules. 2013;18(3):2563-70. doi:10.3390/molecules18032563

20. Ee GC, Lim SK, Lim CM, Dzulkefly K. Alkaloids and carboxylic acids from Piper nigrum. Asian J Chem. 2008;20(8):5931-40.

21. Wei A, Zhou D, Ruan J, Cai Y, Xiong C, Wu G, etal. Study on the contents of aristololactams in Piper wallichii and their renal cytotoxicities. J Food Drug Anal. 2011;19(3):349-54.

22. Ahmad F, Emrizal, Sirat HM, Jamaludin F, Mustapha NM, Ali RM, et al. Antimicrobial and antiinflammatory activities of Piper porphyrophyllum (Fam. Piperaceae). Arabian J Chem. 2014;7(6):1031-3. doi:10.1016/j.arabjc.2010.12.032

23. Tabopda TK, Ngoupayo J, Liu J, Mitaine-Offer AC, Tanoli SA, Khan SN, et al. Bioactive aristolactams from Piper umbellatum. Phytochemistry. 2008;69(8):1726-31. doi:10.1016/j.phytochem.2008.02.018

24. Ke Z, Wei N, Changxiang C, Tianran C. Chemical constituents of Piper boehmeriaefolium var. Tonkinense Chanwu Yanjiu Yu Kaifa. 1999;11:44-47.[Chinese]

25. Diaz A, Diaz PP, Nathan PJ. Dioxoaporphine alkaloid and flavone from Piper manausense YUNK. Rev. Colomb. Quim. 1990;19(2):63-6. [Spanish]

26. Iqbal E, Lim LBL, Salim KA, Faizi S, Ahmed A, Mohamed AJ. Isolation and characterization of aristolactam alkaloids from the stem bark of Goniothalamus velutinus (Airy Shaw) and their biological activities. J King Saud Univ Sci. 2018;30(1):41-8. doi:10.1016/j.jksus.2016.12.008

27. Pena LA, Avella E, Puentes DAM. Prenylated benzoquinone and hydroquinone and other isolated constituents of Piper bogotense C.DC. Rev Colomb Quim. 2000;29:25-37. [Spanish]

28. Barla A, Birman B, Kultur S, Oksuz S. Secondary metabolites from Euphorbia helioscopia. Turkish J Chem. 2006;30:325-32.

29. Salleh WM, Faredaih A, Khong HY, Zulkifli RM. Anticholinesterase and anti-inflammatory constituents from Beilschmiedia pulverulenta Kosterm. Nat. Prod. Sci. 2016;22(4):225-30. doi:10.20307/nps.2016.22.4. 225

30. Gaspar H, Brito Palma FMS, de la Torre MC, Rodriguez B. Sterols from Teucrium abutiloides and T. betonicum. Phytochemistry. 1996;43(3):613-5. doi:10.1016/0031-9422(96)00337-8

31. Wei K, Li W, Koike K, Pei Y, Chen Y, Nikaido T. Complete 1H and 13C NMR assignments of two phytosterols from roots of Piper nigrum. Magn Reson Chem. 2004;42(3):355-9. doi:10.1002/mrc.1347

32. Azami F, Tazikeh Lemeski E, Mahmood Janlou MA. Kojic acid effect on the inhibitory potency of tyrosinase. J Chem Health Risks. 2017;7(2):147-55. doi:10.22034/JCHR.2017.544176

33. Kashima Y, Miyazawa M. Synthesis and biological evaluation of bergenin analogues as mushroom tyrosinase inhibitors. Arch Pharm Res. 2012;35(9):1533-41. doi:10.1007/s12272-012-0903-3

34. Kim YM, Yun J, Lee CK, Lee H, Min KR, Kim Y. Oxyresveratrol and hydroxystilbene compound: Inhibitory effect on tyrosinase and mechanism of action. J Biol Chem. 2002;277(18):16340-4. doi:10.1 074/jbc.M200678200

35. Khanom H, Kayahara H, Tadasa K. Tyrosinase inhibitory activity of Bangladeshi indigenous medicinal plants. Biosci Biotechnol Biochem. 2000;64(9):1967-9. doi:10.1271/bbb.64.1967

36. Mukherjee PK, Badami S, Wahile AM, Rajan S, Suresh B. Evaluation of tyrosinase inhibitory activity of some Indian spices. J Nat Rem. 2001;1(2):125-9. doi:10.18311/jnr/2001/20

37. Kim KS, Kim JA, Eom SY, Lee SH, Min KR, Kim Y. Inhibitory effect of piperlonguminine on melanin production in melanoma B16 cell line by downregulation of tyrosinase expression. Pigment Cell Res. 2005;19(1):90-8. doi:10.1111/j.1600-0749.2005.00281.x

38. Masuoka C, Ono M, Ito Y, Nohara T. Antioxidative, antihyaluronidase and antityrosinase activities of some constituents from the aerial part of Piper elongatum Vahl. Food Sci Technol Res. 2003;9(2):197-201. doi:10.3136/fstr.9.197

 

 


This material may be protected under Copyright Act which governs the making of photocopies or reproductions of copyrighted materials.
You may use the digitized material for private study, scholarship, or research.

Back to previous page

Installed and configured by Bahagian Automasi, Perpustakaan Tuanku Bainun, Universiti Pendidikan Sultan Idris
If you have enquiries with this repository, kindly contact us at pustakasys@upsi.edu.my or Whatsapp +60163630263 (Office hours only)