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Cytotoxic Effects of Compounds Isolated from Ricinodendron Heudelotii

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Cytotoxic Effects of Compounds Isolated from Ricinodendron Heudelotii molecules Article Cytotoxic Effects of Compounds Isolated from Ricinodendron heudelotii Omolara F. Yakubu 1,2, Abiodun H. Adebayo 1,*, Titilope M. Dokunmu 1 , Ying-Jun Zhang 2,* and Emeka E.J. Iweala 1 1 Department of Biochemistry, College of Science and Technology, Covenant University, Canaan Land, Ota PMB 1023, Ogun State, Nigeria; [email protected] (O.F.Y.); [email protected] (T.M.D.); [email protected] (E.E.J.I.) 2 State Key Laboratory of Phytochemistry and Plant Resources of West China, Kunming Institute of Botany, Chinese Academy of Sciences. #132, Lanhei Road, Heilongtan, Kunming 650201, China * Correspondence: [email protected] (A.H.A.); [email protected] (Y.-J.Z.); Tel.: +234-80-3635-7197 (A.H.A.); +86-871-6522-3235 (Y.-J.Z.) Received: 10 August 2018; Accepted: 22 November 2018; Published: 2 January 2019 Abstract: This study was designed to explore the in vitro anticancer effects of the bioactive compounds isolated from Ricinodendron heudelotii on selected cancer cell lines. The leaves of the plant were extracted with ethanol and partitioned in sequence with petroleum ether, ethyl acetate, and n-butanol. The ethyl acetate fraction was phytochemically studied using thin layer chromatography (TLC) and column chromatography (CC). Structural elucidation of pure compounds obtained from the ethyl acetate fraction was done using mass spectra, 1H-NMR, and 13C-NMR analysis. The isolated compounds were subsequently screened using five different cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7, SW-480, and normal lung epithelial cell line, BEAS-2B, to assess their cytotoxic effects. Nine compounds were isolated and structurally elucidated as gallic acid, gallic acid ethyl ester, corilagin, quercetin-3-O-rhamnoside, myricetin-3-O-rhamnoside, 1,4,6-tri-O-galloyl glucose, 3,4,6-tri-O-galloyl glucose, 1,2,6-tri-O-galloyl glucose, and 4,6-di-O-galloyl glucose. Corilagin exhibited the most cytotoxic activity with an IC50 value of 33.18 µg/mL against MCF-7 cells, which were comparable to cisplatin with an IC50 value of 27.43 µg/mL. The result suggests that corilagin isolated from R. heudelotii has the potential to be developed as an effective therapeutic agent against the growth of breast cancer cells. Keywords: anticancer; Ricinodendron heudelotii; chemoprevention 1. Introduction Cancer is a major cause of death across the globe, affecting all age groups [1]. The World Health Organization has predicted that cancer cases will increase from 14 million in 2012 to 22 million in the next four decades [2]. It has caused a great sense of burden both to individual lives and the society at large [3]. The absolute cure of cancer remains a big challenge despite available anticancer agents, awareness campaigns, and prevention strategies. Breast and prostate cancer have the highest incidence in women and men, respectively [4]. It is therefore pertinent to keep exploring for novel chemotherapeutic agents that can evade drug-resistant cancer cells. Natural or natural based anti-cancer drugs, such as vincristine, paclitaxel, bleomycin, and others, have been clinically used over the years [5]. Ricinodendron heudelotii (family: Euphorbiceae) plant parts have been used in traditional medicine to treat cough, stomach ailments, and pain related to child birth. Decoctions and infusions are mostly prepared from the leaves and stem bark. Traditional practitioners prescribe it for women suffering from miscarriages [6]. Phytochemical screening of the leaf extract revealed the Molecules 2019, 24, 145; doi:10.3390/molecules24010145 www.mdpi.com/journal/molecules Molecules 2019, 24, 145 2 of 11 presence of tannins, terpenoids, glycosides, and alkaloids, and it exhibited antimicrobial effects [7]. Two dinorditerpenoids, 1,2-dihydroheudelotinol and heudelotinone, and three other compounds, lupeol, E-ferullic acid octacosylate, and 3-methylmethylorsellinate, have been isolated from the stem bark and roots of R. heudelotii [8]. Seven new tetracyclic triterpenoids ricinodols with potential as 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitors has also been reported to be isolated from R. heudelotii [9]. Yakubu et al. [10] also reported the leaf extract to have regulatory effects on artemisinin toxicity when co-administered with artemisinin. This study aims to identify the chemical structure of isolated bioactive compounds in R. heudelotii as well as evaluate the compoundsfor in vitro cytotoxic activity against human leukemia (HL-60), human hepatocellular carcinoma (SMMC-7721), human lung adenocarcinoma (A549), human breast cancer cell (MCF-7), and colon adenocarcinoma (SW480) cell lines. 2. Results Nine compounds were isolated from the ethyl acetate fraction of R. heudelotii by employing column chromatography, including Sephadex LH-20 and MCI CHP20P gel. 2.1. Structural Elucidation of Isolated Compounds Structure elucidation of the isolated compounds was carried out using spectroscopic techniques: 1H- (600 MHz) and 13C-NMR (150 MHz) and DEPT along with 2D-NMR for some compounds (Figure1). Compound 1 was obtained as an off-white amorphous powder, showing a molecular − ion peak at m/z 170 [M] in the negative ESI-MS. The molecular formula, C7H6O5, was deduced from the combination of 1H-, 13C-NMR and DEPT spectroscopic data. Compound 1 was identified as gallic acid when the data was compared with those in the literature [11,12]. Compound 2, an off-white powder, showed a quasi-molecular ion peak at m/z 198 [M]− in the negative ESI-MS. 1 13 Combining with the H-, C-NMR and DEPT spectroscopic data, a molecular formula, C9H10O5, was deduced. Comparing the data with those in the literature, compound 2 was identified as gallic acid ethyl ester [13]. Compound 3 was obtained as a yellow amorphous powder, showing a molecular ion peak at m/z 633 [M]− in the negative ESI-MS. From 1H-, 13C-NMR, and DEPT spectroscopic data, the molecular formula of C27H22O18 was deduced. Comparing the data with those in the literature, compound 3 was identified as corilagin [14]. Compound 4 was obtained as a yellow amorphous powder. It showed a molecular ion peak at m/z 447 [M − H]− in the negative 1 13 ESI-MS while the molecular formula of C21H20O11, was deduced from the H-, C-NMR, and DEPT spectroscopic data. Likewise, by comparing the data with those in the literature, compound 4 was quercetin-3-O-rhamnoside [15,16]. Compound 5 was obtained as a pale yellow amorphous powder showing a quasi-molecular ion peak at m/z 463 [M − H]− in the negative ESI-MS, and the molecular 1 13 formula of C21H20O12, was deduced from H-, C-NMR, and DEPT spectroscopic data. By comparing the data with those in the literature, compound 5 was identified as myricetin-3-O-rhamnoside [12,17]. Compound 6 was obtained as an off white powder, showing a quasi-molecular ion peak at m/z 635 [M − H]− in the negative ESI-MS. Combining with the 1H-, 13C-NMR, and DEPT spectroscopic data, a molecular formula of C27H24O18 was deduced. By comparing the data with those in literature, compound 6 was identified as 1,4,6-tri-O-galloyl-β-D-glucose [18]. Compound 7 was obtained as a white amorphous powder. It showed a molecular ion peak at m/z 636 [M − H]− in the negative ESI-MS. Combining the 1H-, 13C-NMR, and DEPT spectroscopic data, a molecular formula of C27H24O18 was deduced. The data obtained correlates with those in the literature and compound 7 was identified as 3,4,6-tri-O-galloyl-D-glucose [19]. Compound 8, an off-white amorphous powder with a molecular ion peak at m/z 635 [M − H]− in the negative ESI-MS. A molecular formula of 1 13 C27H24O18, was deduced from the H-, C-NMR, and DEPT spectroscopic data. Comparing the data with those in the literature, compound 8 was identified as 1,2,6-tri-O-galloyl-β-D-glucose [20,21]. Compound 9 was obtained as a white amorphous powder showing a molecular ion peat at m/z 483 [M − H]− in the negative ESI-MS. A molecular formula was deduced from the 1H-, 13C-NMR, Molecules 2019, 24, 145 3 of 11 and DEPT spectroscopic data. By comparing the data with those in the literature, compound 9 was identified as 4,6-di-O-galloyl-D-glucose [22,23]. 2.2. Spectroscopic DataMolecules of Compounds 2018, 23, x FOR1–9 PEER REVIEW 3 of 11 − 1 Gallic acid (1): Off-white2.2.Spectroscopic amorphous Data of Compounds powder, C 17–H9 6O5, negative ESI-MS m/z: 170 [M] , H-NMR 13 (600 MHz, acetone-d6): δ 7.10Gallic (2H, acid s,(1 H-2,6),): Off-whiteC-NMR amorphous (150 powder, MHz, acetone-C7H6O5, negatived6): 121.0 ESI (C-1),-MS m/z 109.0: 170 (C-2,6),[M]−, 1H-NMR 145.9 (C-3,5), 138.3 (C-4),(600MHz, 168.0 acetone (C-7).-d6): δ 7.10 (2H, s, H-2,6), 13C-NMR (150MHz, acetone-d6): 121.0 (C-1), 109.0 (C-2,6), 145.9 (C-3,5), 138.3 (C-4), 168.0 (C-7). Gallic acid ethyl ester (2): Off-white amorphous powder, C9H10O5, negative ESI-MS m/z: − 198 [M]−, 1H-NMR (600 MHz,Gallic acetone-acid ethyld ester): δ (2):0.84Off-white (3H, t,amorphousJ = 7.1 Hz, powder, H-20), C 3.829H10O (2H,5, negative q, J = 7.1ESI- Hz,MS m/z H-1: 1980) [M] , 1 6 H 13 H-NMR (600MHz, acetone-d6): δH 0.84 (3H, t, J = 7.1 Hz, H-2′), 3.82 (2H, q, J = 7.1 Hz, H-1′) 7.05 (2H, 7.05 (2H, s, H-3,5); C-NMR (150 MHz, acetone-d6): δC 120.7 (C-1); 109.4 (C-2,6), 138.0 (C-4), 144.9 s, H-3,5); 13C-NMR (150 MHz, acetone-d6): δC 120.7(C-1); 109.4 (C-2,6), 138.0 (C-4), 144.9 (C-3, 5), 166.8 0 0 (C-3,5), 166.8 (C-7), 60.6(C-7), (C-1 60.6), (C 14.1-1′), (C-214.1 (C).-2′).
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