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Cytotoxic Effect of Damnacanthal, Nordamnacanthal, Zerumbone and Betulinic Acid Isolated from Malaysian Plant Sources

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Cytotoxic Effect of Damnacanthal, Nordamnacanthal, Zerumbone and Betulinic Acid Isolated from Malaysian Plant Sources International Food Research Journal 17: 711-719 (2010) Cytotoxic effect of damnacanthal, nordamnacanthal, zerumbone and betulinic acid isolated from Malaysian plant sources 1,*Alitheen, N.B., 2Mashitoh, A.R., 1Yeap, S.K., 3Shuhaimi, M., 4Abdul Manaf, A. and 2Nordin, L. 1Department of Cell and Molecular Biology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia 2Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia 3Department. of Microbiology, Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400, Serdang, Selangor, Malaysia 4Faculty of Agriculture and Biotechnology, Universiti Darul Iman Malaysia, 20400 Kuala Terengganu, Terengganu, Malaysia Abstract: The present study was to evaluate the toxicity of damnacanthal, nordamnacanthal, betulinic acid and zerumbone isolated from local medicinal plants towards leukemia cell lines and immune cells by using MTT assay and flow cytometry cell cycle analysis. The results showed that damnacanthal significantly inhibited HL- 60 cells, CEM-SS and WEHI-3B with the IC50 value of 4.0 µg/mL, 8.0 µg/mL and 3.3 µg/mL, respectively. Nordamnacanthal and betulinic acid showed stronger inhibition towards CEM-SS and HL-60 cells with the IC50 value of 5.7 µg/mL and 5.0 µg/mL, respectively. In contrast, Zerumbone was demonstrated to be more toxic towards those leukemia cells with the IC50 value less than 10 µg/mL. Damnacanthal, nordamnacanthal and betulinic acid were not toxic towards 3T3 and PBMC compared to doxorubicin which showed toxicity effects towards 3T3 and PBMC with the IC50 value of 3.0 µg/mL and 28.0 µg/mL, respectively. The cell cycle analysis exhibited that damnacanthal exerted its toxicity effect towards HL-60 cells by inducing apoptosis with value of 25% after 72 hours treatment. Thus, these compounds could be the potential anticancer drug with less toxic side effect. Keywords: Betulinic acid, cytotoxic, damnacanthal, nordamnacanthal, zerumbone Introduction methoxyanthraquinone-2-carboxaldehyde (C16H10O5), occurs as pale yellow crystals with a melting point of 210-211°C whereas nordamnacanthal Malaysia is a tropical rainforest country and or 2-formyl-1,3-dihydroxyanthraquinone (C15H8O5), stores the most biologically diverse environment are orange yellow crystals with melting point of 214- in the world (Lee and Houghton, 2005). The huge 218°C. Both these naturally occurring quinone are diversity of the Malaysian forest means that we present widely in the Morinda species. Damnacanthal can expect well diverse chemical structure from and nordamnacanthal have some unique chemical their secondary metabolite and chemical diversity and biological properties. Ali et al. (2000) reported for searching the new agent or novel drug which that damnacanthal and nordamnacanthal isolated suite with the current demand particularly in curing from M. elliptica were cytotoxic towards the MCF-7 various chronic diseases. It is believed that forest (breast carcinoma) and CEM-SS (T-lymphoblastic dwellers in Southeast Asia particularly in Malaysia leukemia) cell lines. use 6,500 different plants to treat illness. These same Zerumbone is a monocyclic sesquiterpene can rain forests have supplied the western world with be found abundantly in rhizomes particularly from herbs and spices for centuries. Zingiber zerumbet Smith and Zingiber aromaticum Damnacanthal and nordamnacanthal (Murakami et al., 2002). Its molecular formula comprise a general class of athraquinone is C H O. Zerumbone is a food phytochemical derivatives. Damnacanthal or 3-hydroxy-1- 15 22 *Corresponding author. Email: [email protected] © All Rights Reserved Tel: + 603-8946 7471; Fax: +603-8946 7510 712 Alitheen, N.B., Mashitoh, A.R., Yeap, S.K., Shuhaimi, M., Abdul Manaf, A. and Nordin, L. possessing great potential for use in chemoprevention Materials and Methods and chemotherapy strategies against cancers. Based on the extensive research done previously, Cells zerumbone has shown very potent anticancer and The cancerous and non-cancerous cell lines antitumor activity. Takada et al. (2005) found that (suspension and anchorage-dependent cells) zerumbone suppressed the activation NF-KappaB were obtained from the American Type Culture and NF-KappaB-regulated gene expression induced Collection (ATCC), the National Cancer Institute by carcinogens, and reported that this inhibition (NCI) and the RIKEN Cell Bank (RCB). The may provide molecular basis for the prevention cancerous cell lines used were CEM-SS (Human and treatment of cancer. In the same year as well, T-lymphoblastic leukemia) (RCB), HL-60 (Human Huang et al. (2005) identified that zerumbone acute promyelocytic leukemia) (ATCC) and WEHI- inhibited the growth of P-388D cells and induced 3B (Mouse myelomonocyte leukemia) (NCI). The DNA fragmentation in culture and significantly non-cancerous cell line and normal cells were 3T3 prolonged the life of P-388D(1)-bearing CDF(1) (Mouse embryo fibroblast) (ATCC) and human mice. Furthermore, it also inhibited the growth of peripheral blood mononuclear cells (PBMC). PBMC human leukemia cell line (HL-60 cell) and human were kindly supplied by Mr. Yeap Swee Keong, colon cancer (HT-29) in vitro (Kirana et al., 2003). Mr. Teo Guan Young, Ms. Haszalina Md. Isa and Betulinic acid [3β-hydroxy-lup-20(19) lupean- Ms. Rohaya Ibrahim from Institute of Biosciences 28-carbonic acid] is a lupine-type triterpene which and Faculty of Biotechnology and Biomolecular was first isolated in 1948 from bark of the London Sciences, UPM. Blood (20-25mL) was taken from plane tree (Platanus acerifolia) (Jung and Duclos, four donors by using the 25 mL syringe. The blood 2006). It can be found abundantly in the bark of the sample was diluted with same volume of PBS. After white birch (Betula alba) or can also be chemically that, the diluted blood sample was carefully layered derived from betulin (Rene et al., 2006). Betulin on Ficoll-Paque Plus (Amersham Biosciences, USA) is an abundant naturally occurring triterpene and it the ratio of 2:1. The mixture was centrifuged at 400 is found predominantly in bushes and trees. Both x g for 40 minutes at 18-20oC. The undisturbed betulin and betulinic acid possess a wide spectrum lymphocyte layer was carefully transferred out. The of biological and pharmacological activities (Sami et lymphocyte was washed and pelleted down with al., 2006). Betulinic acid and its derivatives showed three volume of Phosphate buffer saline (PBS) for cytotoxicity against variety of tumor and cancer cell twice and resuspended in DMEM media (Flowlab, lines comparable to some clinically used drug. For Australia) with 100 IU/mL of penicillin, 100 µg/mL instant, Jeremias et al. (2004) found that in vitro of streptomycin (Flowlab, Australia), 10% v/v Fetal betulinic acid induced specific cell death of more Bovine Serum (FBS) (PAA, Austria). Cell counting than 75% in primary glioblastoma multiforme cells was performed to determine the PBMC cell number at substantially higher rate than established cytotoxic in equal volume of trypan blue. PBMC was used as a drugs vincristine. When betulinic acid was compared normal positive. for in vitro efficiency against several leukemia cell lines with conventionally used cytotoxic drugs, Compounds betulinic acid was more active than 9 out of standard The damnacanthal and nordamnacanthal which therapeutic such as L-asparaginase, dexamethasone, were kindly supplied by Prof. Nordin Haji Lajis from prednisolone and 6-thioguanine (Ehrhardt et al., Institute of Bioscience were isolated from the roots of 2004). Morinda elliptica (Ismail et al., 1997). The zerumbone Although the cytotoxicity of these compounds which was isolated from the rhizome of Zingiber which derived from local plant source has been zerumbet was obtained from Prof. Dr. Hasnah Siraj, studied intensively, they have not been tested and Universiti Teknology Malaysia (UTM). Betulinic compared yet. Besides, the effect of the compounds acid which was extracted from the bark of Melaleuca on the cell cycle progression of HL60 also not been cajuputi was kindly supplied by Associate Prof. fully discovered yet. Thus, this study was carried out Dr. Faujan Ahmad, from Department of Chemistry, to investigate the cytotoxicity of these compounds Faculty of Science, Universiti Putra Malaysia. All the and their effect towards the cell cycle progression of compounds were isolated from the natural resources HL60. as stated above. The powdered-form compounds (damnacanthal, nordamnacanthal, zerumbone and betulinic acid) were dissolved in dimethylsulphoxide (DMSO) (Sigma, USA) to get a stock solution of 10 International Food Research Journal 17: 711-719 Cytotoxic effect of damnacanthal, nordamnacanthal, zerumbone and betulinic acid isolated from Malaysian plant sources 713 mg/mL. The substock solution of 0.06 mg/mL was was treated for 24, 48 and 72 h with damnacanthal, prepared by diluting 6 µl of the stock solution into betulinic acid, zerumbone and doxorubicin at their 994 µL serum-free culture medium, RPMI 1640 respective IC50 value. (the percentage of DMSO in the experiment should In this study, 1 mL of HL-60 cells with a density not exceed 0.5). The stock and substock solutions 1 x 106 cells/mL, respectively were treated with 1 were both stored at 40C. Doxorubicin was used as a mL of damnacanthal, betulinic acid, zerumbone, positive control. This commercial drug was prepared doxorubicin and PWM according to their IC50 value by dissolving it with RPMI medium. The stock and (for cytotoxicity study). The treatment was carried substock solutions were prepared as above. out in the 6 well plates (Nunc) with the total working volume of 2 mL for each well. The treated cells were Cytotoxicity Assay than incubated for 24, 48 and 72 h and harvested Varying concentrations of 0.46, 0.93, 1.87, by centrifugation at 1000 rpm (200 x g) for 10 min. 3.75, 7.5, 15 and 30 µg/mL of damnacanthal, Subsequently, the treated cells were fixed with 80% nordamnacanthal, zerumbone and betulinic acid ethanol at 4oC for 2 h. Then, the cells were spun were prepared from the substock solutions by serial down and washed twice with PBS pH 7.5.
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