Purification of Cinnamic Acid and Aporphine Alkaloids from Enicosanthellum pulchrum Twig Extract and their Biological Activities

Author(s): Noraziah Nordin*, Noor Shafifiyaz Mohd Yazid, Asdren Zajmi, Marjanu Hikmah Elias.

Journal Name: The Natural Products Journal

Volume 9 , Issue 2 , 2019

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Abstract:

Background: Various methods of isolating compounds from plants have been described previously, which include conventional or modern techniques. A preparative-HPLC (prep-HPLC) system has become one of the most convenient methods, with high purity compound as well as consumes less purification time.

Objective: This study is intended to purify compounds from E. pulchrum twig extract using prep- HPLC technique and to test all compounds in several biological activities.

Methods: Prior to purification using prep-HPLC, the twig extract was injected onto HPLC to develop the method through its chromatograms. The established method from HPLC was used to separate the constituents using prep-HPLC. Purified compounds were elucidated through NMR and MS methods as well as through comparison with previously reported data. Three different biological activities were then conducted on the compounds, including cytotoxicity, DPPH, FRAP, and disc diffusion assays.

Results: Cinnamic acid (1) and two aporphine alkaloids (liridine (2) and lysicamine (3)) have been successfully purified and identified. These compounds were first isolated from Enicosanthellum pulchrum using prep-HPLC. Cytotoxic activity revealed that liridine (2) showed strong inhibition against WEHI-3B leukaemic cells of 8.7 µM after 24 h of treatment. In contrast, cinnamic acid (1) and lysicamine (3) exhibited strong inhibitions in antibacterial activity against Staphylococcus aureus, S. epidermidis, Bacillus cereus, Pasteurella multocida and B. subtilis with more than 15 mm of inhibition zone.

Conclusion: These phytochemical findings exhibit three isolated compounds from twig extract of E. pulchrum with diverse biological potential to be developed as new agents.

Keywords: Cinnamaic acid, liridine, lysicamine, preparative-HPLC, cytotoxicity, DPPH, FRAP, disc diffusion.

[1]
Lavault, M.; Guinaudeau, H.; Bruneton, J.; Sevenet, T.; Hadi, A.H.A. (-)-Thaipetaline, a tetrahydroproto berberine from a Malayan Annonaceae. Phytochemistry, 1990, 29, 3845-3847.
[2]
Nordin, N.; Majid, N.A.; Mohan, S.; Dehghan, F.; Karimian, H.; Rahman, M.A.; Ali, H.M.; Hashim, N.M. Cleistopholine isolated from Enicosanthellum pulchrum exhibits apoptogenic properties in human ovarian cancer cells. Phytomedicine, 2016, 23(4), 406-416.
[3]
Nordin, N.; Jalil, J.; Jantan, I.; Murad, S. Platelet-Activating Factor (PAF) receptor binding activity of the roots of Enicosanthellum pulchrum. Pharm. Biol., 2012, 50(3), 284-290.
[4]
Nordin, N.; Majid, N.A.; Othman, R.; Omer, F.A.A.; Nasharuddin, M.N.A.; Hashim, N.M. Plagioneurin B, a potent isolated compound induces apoptotic signalling pathways and cell cycle arrest in ovarian cancer cells. Apoptosis, 2018, 23(2), 152-169.
[5]
Nordin, N.; Fadaeinasab, M.; Mohan, S.; Hashim, N.M.; Othman, R.; Karimian, H.; Iman, V.; Ramli, N.; Ali, H.M.; Majid, N.A. Pulchrin a, a new natural coumarin derivative of Enicosanthellum pulchrum, induces apoptosis in ovarian cancer cells via intrinsic pathway. PLoS One, 2016, 11(5), e0154023.
[6]
Matusheski, N.V.; Wallig, M.A.; Juvik, J.A.; Klein, B.P.; Kushad, M.M.; Jeffery, E.H. Preparative HPLC method for the purification of sulforaphane and sulforaphane nitrile from Brassica oleracea. J. Agric. Food Chem., 2001, 49(4), 1867-1872.
[7]
Hamada, J.S.; Spanier, A.M.; Bland, J.M.; Diack, M. Preparative separation of value added peptides from rice bran proteins by high- performance liquid chromatography. J. Chromatogr. A, 1998, 827, 319-327.
[8]
Zeng, L.; Burton, L.; Yung, K.; Sushan, B.; Kassel, D.B. Automated analytical/preparative high-performance liquid chromatography mass spectrometry system for rapid characterization and purification of compound libraries. J. Chromatogr. A, 1998, 794, 3-13.
[9]
Nordin, N.; Mohan, S.; Hashim, N.M.; Zajmi, A.; Yazid, N.S.M.; Rahman, M.A.; Omer, F.A.A.; Omar, H. Antioxidant, anticancer and antimicrobial activities of methanolic extracts from Enicosanthellum pulchrum (King) Heusden. Sains Malays., 2014, 43(10), 1515-1521.
[10]
Liu, R.; Li, A.; Sun, A. Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the Chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography. J. Chromatogr. A, 2004, 1052(1-2), 217-221.
[11]
Guinaudeau, H. Aporphinoid alkaloids III. J. Nat. Prod., 1983, 46(6), 761-835.
[12]
Omar, H.; Hashim, N.M.; Zajmi, A.; Nordin, N.; Abdelwahab, S.I.; Azizan, A.H.S.; Hadi, A.H.A.; Ali, H.M. Aporphine alkaloids from the leaves of Phoebe grandis (Nees) Mer. (Lauraceae) and their cytotoxic and antibacterial activities. Molecules, 2013, 18, 8994-9009.
[13]
Cheah, S.C.; Appleton, D.R.; Lee, S.T.; Lam, M.L.; Hadi, A.H.; Mustafa, M.R. Panduratin A inhibits the growth of A549 cells through induction of apoptosis and inhibition of NF-Kappa B translocation. Molecules, 2011, 16, 2583-2598.
[14]
Orhan, I.; Kartal, M.; Naz, Q.; Ejaz, A.; Yilmaz, G.; Kan, Y.; Konuklugil, B.; Sener, B.; Choudhary, M.I. Antioxidant and anticholinesterase evaluation of selected Turkishn Salvia species. Food Chem., 2007, 103, 1247-1254.
[15]
Brem, B.; Seger, C.; Pacher, T.; Harti, M.; Hadacek, F.; Hofer, O.; Vajrodaya, S.; Greger, H. Antioxidant dehydrotocopherols as a new chemical character of Stemona species. Phytochemistry, 2004, 65, 2719-2729.
[16]
Benzine, I.F.F. Ferric reducing/antioxidant power assay: Direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol., 1999, 299, 15-27.
[17]
Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis. Annu. Rev. Plant Biol., 2003, 54, 519-546.
[18]
Ekmekcioglu, C.; Feyertag, J.; Marktl, W. Cinnamic acid inhibits proliferation and modulates brush border membrane enzyme activities in Caco-2 cells. Cancer Lett., 1998, 128, 137-144.
[19]
Liu, L.; Hudgins, W.R.; Shack, S.; Yin, M.Q.; Samid, D. Cinnamic acid: A natural product with potential use in cancer intervention. Int. J. Cancer, 1995, 62, 345-350.
[20]
Yen, G.C.; Duh, P.D.; Chuang, D.Y. Antioxidant activity of anthraquinones and anthrone. Food Chem., 2000, 70, 437-441.
[21]
Costa, E.V.; Pinheiro, M.L.B.; Barison, A.; Campos, F.R.; Salvador, M.J.; Maia, B.H.L.N.S.; Cabral, E.C.; Eberlin, M.N. Alkaloids from the bark of Guatteria hispida and their evaluation as antioxidant and antimicrobial agents. J. Nat. Prod., 2010, 73, 1180-1183.


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Article Details

VOLUME: 9
ISSUE: 2
Year: 2019
Page: [125 - 132]
Pages: 8
DOI: 10.2174/2210315508666181009111805
Price: $58

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