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Phytochemical and Biological Investigation of the Leaves Of Journal of Pharmacognosy and Phytochemistry 2015; 4(1): 72-78 E-ISSN: 2278-4136 Phytochemical and biological investigation of the leaves P-ISSN: 2349-8234 JPP 2015; 4(1): 72-78 of Ravenea rivularis (Arecaceae) Received: 11-03-2015 Accepted: 16-04-2015 Mohamed R. Elgindi, Abdel Nasser Singab, Ibrahim M. Mahmoud, Mohamed R. Elgindi Sherouk H. Abdullah Department of Pharmacognosy, Faculty of Pharmacy, Egyptian Russian University, Helwan Abstract University, Cairo, Egypt. Background: The main objective of this work is isolation and characterization of chemical compounds with biological studies from the leaves of Ravenea rivularis (Arecaceae). Materials and Methods: The air Abdel Nasser Singab dried plants extracted with70% methanol, n-hexane, ethyl acetate and n-butanol. The compounds were Department of Pharmacognosy, isolated by column chromatography, TLC, PTLC and paper chromatography. The isolated compounds 1 Faculty of Pharmacy, Ain Shams were identified by spectroscopic methods as H NMR, UV and MS. Results: The compounds identified University, Cairo, Egypt. are Lupeol acetate, Betulinic acid, Apigenin, Luteolin, luteolin-7-O-β-D-glucopyranoside, ferulic acid, caffeic acid and chlorogenic acid. The leave extracts from Ravenea rivularis exhibited antioxidant Ibrahim M. Mahmoud activity, anti-inflammatory and cytotoxicity against Hep-G2. All those compounds are been reported for Department of Pharmacognosy, the first time in Ravenea rivularis. Faculty of Pharmacy, AlAhram Canadian University, Cairo, Keywords: Ravenea rivularis, Arecaceae, triterpenoids, flavonoids, Phenolic acid. Egypt. 1. Introduction Sherouk H. Abdullah The Arecaceae family is one of the biggest vegetal families of the world and by its Department of Pharmacognosy, morphological aspects is the most characteristic of the tropical flora [1]. This family comprises Faculty of Pharmacy, Egyptian 1500 species distributed in 200 genera [2]. The chemical composition of the Arecaceae plants Russian University, Cairo, includes: diterpenes, triterpenes and their methyl esters, steroids, proantocianidines, Egypt. flavonoids, saponins and rarely alkaloids [3-7]. The Ravenea is a genus of solitaire, dioecious palms belonging to the subfamily Ceroxyloideae, tribe Ceroxyleae. The species Ravenea [8] rivularis (also called majesty palm in horticulture) is large palm tree, up to 22 m tall [9] distributed throughout south central Madagascar, Mangoky and Onilahy river systems . The literature reviews not record the phytochemical and biological studies on Ravenea rivularis. 2. Material and Methods 2.1.1 Plant Material Leaves of Ravenea rivularis were collected from the Egyptian Orman garden, Giza, Egypt from august 2011. The plant was kindly identified by Agricultural Engineer Terese Labib, El Orman Botanical Garden. The fresh plant leaves were washed with dist. water, completely dried in shade place at room temperature and then powdered by electric mill. The dried powders were kept in a dark place until subjected to the extraction process. 2.1.2 Material for biology DPPH (1, 1-diphenyl-2-picrylhydrazyl, ascorbic acid, acidified isopropanol, MTT {3-[4, 5- dimethylthiazol-2-yl]-2, 5 diphenyltetrazolium bromide} solution and Hepatocellular Carcinoma (Hep-G2) and Human Breast Adenocarcinoma (MCF-7). Griess reagent, Cells were cultured in RPMI-1640 and Dexamethasone (50mg/ml) as a potent anti-inflammatory. 2.2 Methods 2.2.1 Extraction and Isolation The powdered leaves of Ravenea rivularis (3 Kg) were extracted with 70% methanol at room Correspondence: temperature and the solvent was removed under reduced pressure to give (300 g). The Mohamed R. Elgindi methanolic extract was defatted with petroleum ether. The defatted residue was dissolved in Department of Pharmacognosy, distilled water and the aqueous filtrate was successively extracted with n-hexane followed with Faculty of Pharmacy, Egyptian ethyl acetate and finally with n-butanol. The three fractions; n-hexane, ethyl acetate and Russian University, Helwan butanol were evaporated until dryness to give 35g, 40g and 4 g respectively. The n-hexane University, Cairo, Egypt. ~ 72 ~ Journal of Pharmacognosy and Phytochemistry extract was chromatographed on silica gel column. Elution (C-5), δ 98.84 (C-6), δ 164.25 (C-7), δ 93.95 (C-8), δ 157.3 was achieved with gradient of petroleum ether: ethyl acetate (C-9), δ 103.625 (C-10), δ 121.15 (C-1'), δ 128.42 (C-2'), δ (100% petroleum ether ~ 100% ethyl acetate). Similar 115.94 (C-3'), δ 161.16 (C-4'), δ 115.94 (C-5'), δ 128.42 (C-6'). fractions were collected. Two major fractions eluted from the column was subjected to silica gel column and sephadex Compound (4): Fine powders. EI/MS m/z 194 [M+] (100%). [10, 1 column, followed by PTLC to gave two lupine triterpenoids H-NMR (400 MHz, CD3OD) at δ: 7.18 (1H, d, J=2.0 Hz, H- 11], Lupeol acetate (1) and Betulinic acid (2). The ethyl acetate 2), δ 9.59 (OH, S, H-4), δ 6.81 (1H, d, J=8.0 Hz, H-5), δ 7.07 extract was divided into two portions A and B. Ethyl Acetate (1H, dd, J=8.0, 2.0 Hz, H-6), δ 7.61 (1H, d, J=16.0 Hz, H-7), δ extract portion A was fractionated by silica gel column with 6.31 (1H, d, J=16.0 Hz, H-8), δ 9.15 (1H, S, H-9), δ 3.95 (3H, 13 solvent system ethyl acetate in n-hexane followed by PTLC S, O-Me). C-NMR (100 MHz, CD3OD) at δ: 127.8 (C-1), δ which afforded three compounds, Apigenin (3), Ferulic acid 111.8 (C-2), δ 149.4 (C-3), δ 150.5 (C-4), δ 116.0 (C-5), δ (4) and Luteolin (5). Ethyl Acetate extract portion B was 124.0 (C-6), δ 146.9 (C-7), δ 116.5 (C-8), δ 171.0 (C-9), δ 56.5 fractionated by silica gel column with solvent system methanol (O-Me). in chloroform, followed by PPC which afforded two compounds, Luteolin-7-O-β-D-glucoside (6) and Caffeic acid Compound (5): Yellow powders. UV (λmax in MeOH): gives (7). N-Butanol extract was fractionated by silica gel column bands at 349 and 253 nm for band I and II, addition of with solvent system methanol in chloroform followed by PPC NaOMe; 402, 330 and 265, NaOAc; 390, 325 and 269, H3BO3; which afford one phenolic acid compound, Chlorogenic acid 430, 370, 301 and 262, AlCl3; 426, 328, 300 and 274, while (8). HCl; 388, 356, 296 and 275. EI/MS m/z 286 [M+] (75%). 1H- NMR (400 MHz, DMSO-d6) at δ: 6.67 (1H, S,H-3), δ 12.97 Compound (1): White needle crystals. EI/MS m/z 468 [M+] (1H, S, 5-OH), δ 6.18 (1H, d, J=2.0 Hz, H-6), δ 6.44 (1H, d, 1 (17.2%). H-NMR (400 MHz, CDCl3) at δ: 1.66 (3H, s, H-30), J=2.0 Hz, H-8), δ 7.39 (1H, m, H-2'), δ 6.89 (1H, d, J=8.0 Hz, 13 1.43 (3H, s, H-25) 1.21 (3H, s, H-28), 1.01 (3H, s, H-23), 0.95 H-5'), δ 7.42 (1H, m, H-6'). C-NMR (100 MHz, DMSO-d6) at (3H, s, H-24), 0.87 (3H, s, H-26), 0.81 (3H, s, H-27), δ 4.50 δ : 163.87 (C-2), δ 102.85 (C-3), δ 181.62 (C-4), δ 161.46 (C- and 4.61 (2H, s, H-29a and H-29b), and the acetate methyl at δ 5), δ 98.82 (C-6), δ 164.14 (C-7), δ 93.82 (C-8), δ 157.28 (C- 2.065 (3H, H-2’), and δ 4.46 (1H, dd, J=4.4, 12.8 Hz, H- 9), δ 103.67 (C-10), δ 121.49 (C-1'), δ 113.35 (C-2'), δ 145.72 13 3). C-NMR (100 MHz, CDCl3) at δ: 38.57(C-1), δ 27.53(C- (C-3'), δ 149.69 (C-4'), δ 116.00 (C-5'), δ 118.96 (C-6'). 2), δ 81.19(C-3), δ 40.19(C-4), δ 55.57(C-5), δ 18.39(C-6), δ 34.39(C-7), δ 41.04(C-8), δ 50.53(C-9), δ 37.27(C-10), δ Compound (6): Yellow needles. UV (λmax in MeOH): gives 21.13(C-11), δ 25.28(C-12), δ 38.23(C-13), δ 43.02(C-14), δ bands at 348 and 255 nm for band I and II, addition of 27.53(C-15),δ 35.76(C-16), δ 43.19(C-17), δ 48.47(C-18), δ NaOMe; 392, 300 and 262, NaOAc; 405, 364, 266 and 259, 48.20(C-19), δ 151.21(C-20), δ 29.98(C-21),δ 40.19(C-22), δ H3BO3; 370 and 259, AlCl3; 430, 329, 299 and 274, while 28.14(C-23), δ 16.69(C-24), δ 16.38(C-25), δ 16.16(C-26), δ HCl; 387, 358, 295 and 273. EI/MS m/z 286 [aglycone 1 14.70(C-27), δ 18.19(C-28), δ 109.54(C-29), δ 19.54(C-30), δ fragment]. H-NMR (400 MHz, DMSO-d6) at δ: 6.74 (1H,S, 171.26(C-1'), δ 28.14(C-2'). H-3), δ 12.97 (1H, br, s, H-5), δ 6.43 (1H, d, J= 2.1 Hz, H-6), δ 6.78 (1H, d, J=2.1 Hz, H-8), δ 7.44 (1H, d, J=2.1 Hz, H-2'), Compound (2): White powders. EI-MS m/z (rel. Int.): m/z 12.97 (1H, brs, H-3'), δ 12.97 (1H, brs, H-4'), δ 6.9 (1H, d, [M+] 456 (5%).
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