Phytoconstituents profiling of Cissus rotundifolia (Forssk.) Vahl. by HPLC-MS/MS, and evaluation of its free radical scavenging activity (DPPH) and cytotoxicity

Subject Areas : Phytochemistry: Isolation, Purification, Characterization

Ataa Said ¹ , Elsayed Ali Aboutabl ² , Farouk Rasmy Melek ³ , Gehad Abdel Jaleel Raheem Abdel Jaleel ⁴ , Mona Raslan ⁵

1 - Pharmacognosy Department, National Research Centre, Dokki, 12622 Giza, Egypt
2 - Pharmacognosy Department, Faculty of Pharmacy, Cairo University, Kasr-el-Aini Street, 11562 Cairo, Egypt
3 - Chemistry of Natural Compounds Department, National Research Centre, Dokki, 12622 Giza, Egypt
4 - Pharmacology Department, National Research Centre, Dokki, 12622 Giza, Egypt
5 - Pharmacognosy Department, National Research Centre, Dokki, 12622 Giza, Egypt

Received: 2018-01-01 Accepted : 2018-05-25 Published : 2018-06-01

Keywords: Cytotoxicity, HPLC-ESI-MS, Tandem mass, Free radical scavenging activity, <i>Cissus rotundifolia</i> (Forssk.) Vahl,

Abstract :

Characterization of phytoconstituents in the 70% methanolic extract of Cissus rotundifolia (Forssk.) Vahl. was performed using high-performance liquid chromatography coupled with electrospray ionization mass spectrometry. Furthermore, tandem mass spectrometry (MS/MS) was performed to assist in the structural elucidation of compounds. Twenty-seven compounds were identified. The identified compounds were four acids, sixteen phenolics, two steroidal saponins, two coumarins, two stilbenoids and one triterpene. Astragalin 1, β-amyrin 2 and 1β-hydroxy-kryptogenin-1-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside 3 were isolated by column chromatography and their structures were identified by spectral analysis including 1D and 2D NMR. The plant extract and the isolated compounds 1-3 were evaluated for their radical scavenging activity. Compounds 1 and 2 showed significant activity relative to that of ascorbic acid as a standard. The cytotoxicity of the plant extract, the isolated compounds and the standard doxorubicin was evaluated using the three human tumor cell lines HT116, MCF-7 and PC-3. The plant extract exhibited significant cytotoxicity against MCF-7 while showing no activity against the other cell lines. The isolated compounds 1-3 showed no activity against the used cell lines.

References:

Abu-Reidah, I.M., Arráez-Román, D., Segura-Carretero, A., Fernández-Gutiérrez, A., 2013.Profiling of phenolic and other polar constituents from hydro-methanolic extract of watermelon (Citrullus lanatus) by means of accurate-mass spectrometry (HPLC-ESI-QTOF-MS). Food Res. Int. 51(1), 354-362.

Al-Fatimi, M., Wurster, M., Schröder, G., Lindequist, U., 2007. Antioxidant, antimicrobial and cytotoxic activities of selected medicinal plants from Yemen. J. Ethnopharmacol. 111(3), 657-666.

Al-Mamary, M.A., 2002. Antioxidant activity of commonly consumed vegetables in Yemen. Malays. J. Nutr. 8(2), 179-189.

Alzoreky, N.S., Nakahara, K., 2003. Antibacterial activity of extracts from some edible plants commonly consumed in Asia. Int. J. Food Microbiol. 80(3), 223-230.

Ara, K., Rahman, M.S., Rahman, A.H.M.M., Hasan, C.M., Rashid, M.A., 2009. Terpenoids and coumarin from Bursera serrata Wall. Dhaka Univ. J. Pharm. Sci. 8(2), 107-110.

Beltrame, F.L., Ferreira, A.G., Cortez, D.A., 2002. Coumarin glycoside from Cissus Sicyoides. Nat. Prod. Lett. 16(4), 213-216.

Beltrame, F.L., Pessini, G.L., Doro, D.L., Filho, B.P., Bazotte, R.B., Cortez, D.A.G., 2002. Evaluation of the antidiabetic and antibacterial activity of Cissus sicyoides. Braz. Arch. Biol. Technol. 45(1), 21-25.

Blazics, B., Alberti, Á., Béni, S., Kursinszki, L., Tölgyesi, L., Kéry, Á., 2011. Identification and LC-MS-MS determination of acteoside, the main antioxidant compound of Euphrasia rostkoviana, using the isolated target analyte as external standard. J. Chromatogr. Sci. 49(3), 203-208.

Braca, A., Tommasi, N.D., Bari, L.D., Pizza, C., Politi, M., Morelli, I., 2001. Antioxidant principles from Bauhinia terapotensis. J. Nat. Prod. 64, 892-895.

Castro, C., Mura, F., Valenzuela, G.; Figueroa, C., Salina, R., Carolina, Z.M.,Torres, J. L., Fugue, E., Delporte, C., 2014. Identification of phenolic compounds by HPLC-ESI-MS/MS and antioxidant activity from Chilean propolis. Food Res. Int. 64, 873-879.

Cho, I.H., Choi, Y.J., Gong, J.H., Shin, D., Kang, M.K., Kang, Y.H., 2015. Astragalin inhibits autophagy-associated airway epithelial fibrosis. Respir. Res.16, 51-64.

Choi, J., Kang, H.J., Kim, S.Z., Kwon, T.O., Jeong, S.I., Jang, S.I., 2013. Antioxidant effect of astragalin isolated from the leaves of Morus alba L. against free radical-induced oxidative hemolysis of human red blood cells. Arch. Pharm. Res. 36(7), 912-917.

Fingolo, C.E., de S. Santos, T., Filho, M.D.M.V., Kaplan, M.A.C., 2013. Triterpene esters: Natural products from Dorstenia arifolia (Moraceae). Molecules 18(4), 4247-4256.

Gold-Smith, F., Fernandez, A., Bishop, K., 2016. Mangiferin and Cancer: Mechanisms of Action.

Gómez-Romero, M., Zurek, G., Schneider, B., Baessmann, C., Segura-Carretero, A., Fernández-Gutiérrez, A., 2011. Automated identification of phenolics in plant-derived foods by using library search approach. Food Chem. 124, 379-386.

Han, J., Bang, M., Chun, O., Kim, D., Lee, C., Baek, N., 2004. Flavonol glycosides from the aerial parts of Aceriphyllum rossii and their antioxidant activities. Arch. Pharm. Res. 27(4), 390-395.

Horai, H., Arita, M., Kanaya, S., Nihei, Y., Ikeda, T., Suwa, K., Ojima, Y., Tanaka, K., Tanaka, S., Aoshima, K., Oda, Y., Kakazu, Y., Kusano, M., Tohge, T., Matsuda, F., Sawada, Y., Yokota, H.M., Nakanishi, H., Ikeda, K., Akimoto, N., Maoka, T., Takahashi, H., Ara, T., Sakurai, N., Suzuki, H., Shibata, D., Neumann, S., Iida, T., Tanaka, K., Funatsu, K., Matsuura, F., Soga, T., Taguchi, R., Saito, K., Nishioka, T., 2010. MassBank: A public repository for sharing mass spectral data for life sciences. J. Mass Spectrom. 45(7), 703-714.

Jia, M., Lib, Q., Jic, H., Lua, H., 2014. Investigation of the distribution and season regularity of resveratrol in Vitis amurensis via HPLC-DAD-MS/MS. Food Chem. 142, 61-65.

Kang, J.G., Hick, L.A., Price, W.E., 2007. A fragmentation study of isoflavones in negative electrospray ionization by MSn ion trap mass spectrometry and triple quadrupole mass spectrometry. Rapid Commun. Mass Spectrom. 21(6), 857-568.

Kawase, M., Sakagami, H., Motohashi, N., Hauer, H., Chatterjee, S.S., Spengler, G., Vigyikanne, A.V., Molnar, A., Molnar, J., 2005. Coumarin derivatives with tumor-specific cytotoxicity and multidrug resistance reversal activity. In vivo 19, 705-712.

Kıvrak, İ., Kıvrak, Ş., Harmandar, M., Çetintaş, Y., 2013. Phenolic compounds of Pinus brutia Ten.: chemical investigation and quantitative analysis using an ultra-performance liquid chromatography tandem mass spectrometry with electrospray ionization source. Rec. Nat. Prod. 7(4), 313-319.

Kumar, M., Rawat, P., Dixit, P., Mishra, D., Gautam, A.K., Pandey, R., Singh, D., Chattopadhyay, N., Maurya, R., 2010. Anti-osteoporotic constituents from Indian medicinal plants. Phytomedicine 17(13), 993-999.

Lin, C.F., Hwang, T.L., Lin, S.Y., Huang, Y.L., 2012. Bioactive isocoumarins from Cissus pteroclada. J. Chin. Med. 23(1), 41-49.

Lopez-Lazaro, M., Galvez, M., Martin-Cordero, C., Ayuso, M.J., 2002. Cytotoxicity of flavonoids on cancer cell lines. Structure-activity relationship. Stud. Nat. Prod. Chem. 27(H), 891-932.

Marín, C., Ramírez-Macías, I., López-Céspedes, A., Olmo, F., Villegas, N., Díaz, J. G., Rosales, M. J., Gutiérrez-Sánchez, R., Sánchez-Moreno, M., 2011. In vitro and in vivo trypanocidal activity of flavonoids from Delphinium staphisagria against Chagas disease. J. Nat. Prod. 74(4), 744-750.

Mena, P., Calani, L., Dall’Asta, C., Galaverna, G., García-Viguera, C., Bruni, R.,Crozier A., Del Rio, D., 2012. Rapid and comprehensive evaluation of (poly)phenolic compounds in pomegranate (Punica granatum L.) juice by UHPLC-MSⁿ. Molecules 17(12), 14821-14840.

Pan, G.Y., Li, W.F., Luo, P., Qin, J.K., Su, G.F., 2013. Study on steroidal and triterpenoid constituents from Cissus pteroclada. Zhong Yao Cai 36(8), 1274-1277.

Pietta, P.G., 2000. Flavonoids as antioxidants. J. Nat. Prod. 63(7), 1035-1042.

Podolak, I. Galanty, A., Sobolewska, D., 2010. Saponins as cytotoxic agents: a review. Phytochem. Rev. 9(3), 425-474.

Quílez, A.M., Saenz, M.T., Garcia, M.D., de la Puerta, R., 2004. Phytochemical analysis and anti-allergic study of Agave intermixta Trel. and Cissus sicyoides L. J. Pharm. Pharmacol. 56(9), 1185-1189.

Reed, K. A., 2009. Identification of Phenolic Compounds from Peanut Skin Using HPLC-MSⁿ. PhD. Faculty of the Virginia Polytechnic Institute and State University, USA.

Said, A., Aboutabl, E.A., El Awdan, S., Raslan, M., 2015a. Proximate analysis, phytochemical screening and bioactivities evaluation of Cissus rotundifolia (Forssk.) Vahl. (Fam. Vitaceae) and Sansevieria cylindrica Bojer ex Hook. (Fam. Dracaenaceae) growing in Egypt. Egypt. Pharm. J. 14(3), 180-186.

Said, A., Aboutabl, E.A., Melek, F.R., Abdel Jaleel, G.A., Raslan, M.,2015b. Steroidal saponins and homoisoflavanone from the aerial parts of Sansevieria cylindrica Bojer ex Hook. Phytochem. Lett. 12, 113-118.

Sánchez-Rabaneda, F., Jáuregui, O., Casals, I., Andrés-Lacueva, C., Izquierdo-Pulido, M., Lamuela-Raventós, R.M., 2003. Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). J. Mass Spectrom. 38(1), 35-42.

Schieber, A., Berardini, N., Carle, R., 2003. Identification of flavonol and xanthone glycosides from mango (Mangifera indica L. CV. “tommy atkins”) peels by high-performance liquid chromatography-electrospray ionization mass spectrometry. J. Agric. Food Chem. 51(17), 5006-5011.

Simirgiotis, M.J., Bórquez, J., Schmeda-Hirschmann, G., 2013. Antioxidant capacity, polyphenolic content and tandem HPLC-DAD-ESI/MS profiling of phenolic compounds from the South American berries Luma apiculata and L. chequen. Food Chem. 139(1-4), 289-299.

Singh, G., Rawat, P., Maurya, R., 2007. Constituents of Cissus quadrangularis. Nat. Prod. Res. 21(6), 522-528.

Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J.T., Bokesch, H., Kenney, S., Boyd, M.R., 1990. New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst. 82(13), 1107-1112.

Spinola, V., Pinto, J., Castilho, P.C., 2015. Identification and quantification of phenolic compounds of selected fruits from Madeira Island by HPLC-DAD-ESI-MSⁿ and screening for their antioxidant activity. Food Chem. 173, 14-30.

Sunil, C., Irudayaraj, S. S., Duraipandiyan, V., Al-Dhabi, N. A., Agastian, P., Ignacimuthua, S., 2014. Antioxidant and free radical scavenging effects of β-amyrin isolated from S. cochinchinensis Moore. leaves. Ind. Crops Prod. 61, 510-516.

Vázquez, H. L., Palazon, J., Navarro-Ocaña, A., 2012. The Pentacyclic Triterpenes, α-, β-Amyrins: A Review of Sources and Biological Activities. Phytochemicals: A Global Perspective of Their Role in Nutrition and Health, Intech. pp. 487-502.

Walczak, K., Browski, D., Langner, E., Zgrajka, W., Pi, A. J., Kocki, T., Rzeski, W., Turski, W. A., 2011. Kynurenic acid synthesis and kynurenine aminotransferases expression in colon-derived normal and cancer cells. Scand. J. Gastroenterol. 46(7-8), 903-912.

Wang, Y., Zhang, Z., He, H., Gao, S., Kong, N., Ding, M., Hao, X., 2006. Lignans and triterpenoids from Cissus repens (Vitaceae). Acta Bot. Yunnanica 28(4), 433-437.

Weber, J.F.F., Thomas, N.F., Abdul Wahab, I., Feroz, F., Buniyamin, I., 2008. Mass spectrometry of unnatural stilbene dimers. MJAS 12(3), 633-637.

Wu, B., Qu, H., Cheng, Y., 2008. Cytotoxicity of new stilbenoids from Pholidota chinensis and their spin-labelled derivatives. Chem. Biodivers. 5(9), 1803-1810.

Wu, Q., Wang, M., Simon, J.E., 2003. Determination of isoflavones in red clover and related species by high-performance liquid chromatography combined with ultraviolet and mass spectrometric detection. J. Chromatogr. A 1016(2), 195-209.

Xiao, K., Zhang, H. J., Xuan, L. J., Zhang, J., Y. Xu, M., Bai, D. L., 2008. Stilbenoids: Chemistry and bioactivities. Stud. Nat. Prod. Chem. 34, 453-646.

Xue, Y.Q., Di, J.M., Luo, Y., Cheng, K.J., Wei, X., Shi, Z., 2014. Resveratrol oligomers for the prevention and treatment of cancers. Oxid.Med. Cell. Longev. vol. 2014, doi:10.1155/2014/765832.

Zhang, T., Liu, H., Liu, X.T., Xu, D., Chen, X., Wang, Q., 2010. Qualitative and quantitative analysis of steroidal saponins in crude extracts from Paris polyphylla var. yunnanensis and P. polyphylla var. chinensis by high-performance liquid chromatography coupled with mass spectrometry. J. Pharm. Biomed. Anal. 51(1), 114-124.