Cytotoxic Activity of 2-O-β-glucopyranosil Cucurbitacin D from Benalu Batu (Begonia sp.) Growing in Morowali, Central Sulawesi

https://doi.org/10.22146/ijc.43626

Muhammad Sulaiman Zubair(1*), Walied Mohamed Alarif(2), Mohamed Ali Ghandourah(3), Syariful Anam(4), Ibrahim Jantan(5)

(1) Department of Pharmacy, Science Faculty, Tadulako University, Jl. Soekarno Hatta Tondo, Palu 94118, Indonesia
(2) Department of Marine Chemistry, Marine Science Faculty, King Abdul Aziz University, Jeddah 21589, Saudi Arabia
(3) Department of Marine Chemistry, Marine Science Faculty, King Abdul Aziz University, Jeddah 21589, Saudi Arabia
(4) Department of Pharmacy, Science Faculty, Tadulako University, Jl. Soekarno Hatta Tondo, Palu 94118, Indonesia
(5) School of Pharmacy, Taylor’s University, Lakeside Campus, Jl. Taylors No. 1, Subang Jaya 47500, Selangor, Malaysia
(*) Corresponding Author

Abstract


Benalu batu (Begonia sp.) had been used traditionally as an anticancer medicinal plant by Wana tribe in Morowali, Central Sulawesi, This study aims to evaluate the cytotoxic activity of 2-O-β-glucopyranosil cucurbitacin D, isolated from the ethyl acetate soluble fraction of Benalu batu (Begonia sp.) and to determine its action on apoptosis induction. Benalu batu (Begonia sp.) herb was extracted by maceration using ethanol 96% as a solvent. Vacuum liquid column chromatography and preparative thin layer chromatography have been applied on fractionation and isolation of the compound. The structure elucidation was performed by extensive analysis of 1D/2D nuclear magnetic resonance (NMR) and Mass Spectrophotometer (MS). Cytotoxic activity against human breast adenocarcinoma (MCF-7) and human colon colorectal carcinoma (HCT-116) cell lines were performed by 5-diphenyltetrazolium bromide (MTT) method. Annexin V-FITC assay was employed to determine the apoptosis induction. 2-O-β-glucopyranosil cucurbitacin D showed potent cytotoxic activity against MCF-7 and HCT-116 with the IC50 of 19.913 and 0.002 μg/mL, respectively. Annexin V-FITC assay clearly exhibited the cytotoxic mechanism on MCF-7 and HCT-116 via apoptosis induction with a significant percentage of early and late apoptosis of 75.8 and 78.4%, respectively. This study reveals the potential cytotoxic activity of 2-O-β-glucopyranosil cucurbitacin D isolated from Benalu batu and its mechanism via apoptosis induction.

Keywords


Begonia sp.; 2-O-β-glucopyranosil cucurbitacin D; cytotoxic; MCF-7; HCT-116

Full Text:

Full Text PDF


References

[1] Harvey, A.L., Eldrada-Ebel, R., and Quinn, R.J., 2015, The re-emergence of natural products for drug discovery in the genomics era, Nat. Rev. Drug Discovery, 14 (2), 111–129.

[2] Dias, D.A., Urban, S., and Roessner, U.A., 2012, Historical overview of natural products in drug discovery, Metabolites, 2 (2), 303–333.

[3] Newman, D.J., and Cragg, G.M., 2012, Natural product as sources of new drugs over the 30 years from 1981 to 2010, J. Nat. Prod., 75 (3), 311–335.

[4] Ding, B., Nakamura, K., Kono, Y., Ho, M.J., and Peng, C.I., 2014, Begonia jinyunensis (Begoniaceae, section Platycentrum), a new palmately compound leaved species from Chongqing, China, Bot. Stud., 55, 62.

[5] Zubair, M.S., Anam, S., Khumaidi, A., Susanto, Y., Hidayat, M., and Ridhay, A., 2016, Molecular docking approach to identify potential anticancer compound from Benalu batu (Begonia sp.), AIP Conf. Proc., 1755 (1), 080005.

[6] Ramesh, N., Viswanathan, M.B., Saraswathy, A., Balakrishna, K., Brindha, P., and Lakshmanaperumalsamy, P., 2002, Phytochemical and antimicrobial studies of Begonia malabarica, J. Ethnopharmacol., 79 (1), 129–132.

[7] Jeeva, S., and Antonisamy, J.M., 2012, Anti-bacterial and phytochemical studies on methanolic extracts of Begonia floccifera Bedd. flower, Asian Pac. J. Trop. Biomed., 2 (1), S151–S154.

[8] Kalpanadevi, V., and Mohan, V.R., 2012, In vitro antioxidant studies of Begonia malabarica Lam. and Begonia floccifera Bedd, Asian Pac. J. Trop. Biomed., 2 (3), S1572–1577.

[9] Pandikumar, P., Babu, N.P., and Ignacimuthu, S., 2009, Hypoglycemic and antihyperglycemic effect of Begonia malabarica Lam. in normal and streptozotocin induced diabetic rats, J. Ethnopharmacol., 124 (1), 111–115.

[10] Doskotch, R.W., and Hufford, C.D., 1970, Hexanor-cucurbitacin D, a degraded cucurbitacin from Begonia tuberhybrida var. alba, Can. J. Chem., 48, 1787–1788.

[11] Frei, B., Heinrich, M., Herrmann, D., Orjala, J.E., Schmitt, J., and Sticher, O., 1998, Phytochemical and biological investigation of Begonia heracleifolia, Planta Med., 64 (4), 385–386.

[12] Wu, P.L., Lin, F.W., Wu, T.S., Kuoh, C.S., Lee, K.H., and Lee, S.J., 2004, Cytotoxic and anti-HIV principles from the rhizomes of Begonia nantoensis, Chem. Pharm. Bull., 52 (3), 345–349.

[13] Anam, S., Yuliet, Ritna, A., Dwimurti, F., Rismayanti, D., and Zubair, M.S., 2014, Aktivitas sitotoksik ekstrak metanol Benalu batu (Begonia sp.): Ethnomedicine suku Wana Sulawesi Tengah, Indones. J. Pharm. Sci., 12 (1), 10–16.

[14] Zubair, M.S., Anam, S., and Lallo, S., 2016, Cytotoxic activity and phytochemical standardization of Lunasia amara Blanco wood extract, Asian Pac. J. Trop. Biomed., 6 (11), 962–966.

[15] Theodore, C.M., Lorig-Roach, N., Still, P.C., Johnson, T.A., Draskovic, M., Schwochert, J.A., Naphen, C.N., Crews, M.S., Barker, S.A., Valeriote, F.A., Lokey, R.S., and Crews, P., 2015, Biosynthetic products from a nearshore-derived gram negative bacterium enable reassessment of the kailuin depsipeptides, J. Nat. Prod., 78 (3), 441–452.

[16] Duangmano, S., Sae-Lim, P., Suksamrarn, A., Domann, F.E., and Patmasiriwat, P., 2012, Cucurbitacin B inhibits human breast cancer cell proliferation through disruption of microtubule polymerization and nucleophosmin/B23 trans location, BMC Complement. Altern. Med., 12, 185.

[17] Lopez-Haber, C., and Kazanietz, M.G., 2013, Cucurbitacin I inhibits Rac1 activation in breast cancer cells by a reactive oxygen species-mediated mechanism and independently of Janus tyrosine kinase 2 and P-Rex1, Mol. Pharmacol., 83 (5), 1141–1154.

[18] Kong, Y., Chen, J., Zhou, Z., Xia, H., Qiu, M.H., and Chen, C., 2014, Cucurbitacin E induces cell cycle G2/M phase arrest and apoptosis in triple negative breast cancer, PLoS One, 9 (7), e103760.

[19] Ayyad, S.E.N., Abdel-Lateff, A., Basaif, S.A., and Shier, T., 2011, Cucurbitacins-type triterpene with potent activity on mouse embryonic fibroblast from Cucumis prophetarum, cucurbitaceae, Pharmacogn. Res., 3 (3), 189–193.

[20] Ayyad, S.E.N., Abdel-Lateff, A., Alarif, W.M., Patacchioli, F.R., Badria, F.A., and Ezmirly, S.T., 2012, In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma, Environ. Toxicol. Pharmacol., 33 (2), 245–251.

[21] Ku, J.M., Hong, S.H., Kim, H.I., Lim, Y.S., Lee, S.J., Kim, M., Seo, H.S., Shin, Y.C., and Ko, SG., 2018, Cucurbitacin D exhibits its anti-cancer effect in human breast cancer cells by inhibiting Stat3 and Akt signaling, Eur. J. Inflammation, 16, 1–9.

[22] Thoennissen, N.H., Iwanski, G.B., Doan, N.B., Okamoto, R., Lin, P., Abbasi, S., Song, J.H., Yin, D., Toh, M., Xie, W.D., Said, J.W., and Koeffler, H.P., 2009, Cucurbitacin B induces apoptosis by inhibition of the JAK/STAT pathway and potentiates antiproliferative effects of gemcitabine on pancreatic cancer cells, Cancer Res., 69 (14), 5876–5884.



DOI: https://doi.org/10.22146/ijc.43626

Article Metrics

Abstract views : 966 | views : 637


Copyright (c) 2019 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 / 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.