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Inflammatory Activities of Extracts from the Fruits Ofziziphus Jujuba Mill

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Inflammatory Activities of Extracts from the Fruits Ofziziphus Jujuba Mill _ Food Science and Technology Research, 23 (3), 417 426, 2017 Copyright © 2017, Japanese Society for Food Science and Technology doi: 10.3136/fstr.23.417 http://www.jsfst.or.jp Original paper Study on the Bioactive Constituents and in vitro Antioxidant and in vivo Anti- inflammatory Activities of Extracts from the Fruits ofZiziphus Jujuba Mill. cv. Jinsixiaozao Hort 1 1 1 2 1,2* 1 Xuejiao LI , Xia LI , Bin ZHOU , Shuli MAN , Wenyuan GAO and Songsong JING 1Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China 2Tianjin Key Laboratory of Industry Microbiology, College of Biotechnology, Tianjin University of Science & Technology, Tianjin 300457, China Received January 15, 2015 ; Accepted May 7, 2015 The aims of this study were to investigate the antioxidant and anti-inflammatory effects of extracts from fruits of Ziziphus jujuba Mill. cv. jinsixiaozao Hort (ZJMH) and its active chemical constituents. For antioxidant activity, reducing power, DPPH and β-carotene bleaching inhibition assay were used. Ethyl acetate extract exhibited the strongest antioxidant potential in all the models. For anti-inflammatory activity, petroleum ether extract showed the strongest inhibition (32.86%) against carrageenan-induced paw edema, which also displayed potent anti- inflammatory activity against xylene-induced ear edema (41.52%). The contents of phenolic acids, flavonoids, triterpenes, anthocyanins, triterpenoid saponins of different extracts were also observed. Moreover, seven compounds were first isolated from petroleum ether extract and showed considerable anti-inflammatory activity, especially alphitolic acid and stigmasterol. The results showed that ZJMH can be a natural antioxidant and anti- inflammatory agent. Keywords: Ziziphus jujuba Mill. cv. jinsixiaozao Hort., chemical constituents, antioxidative activity, anti-inflammatory activity, alphitolic acid, stigmasterol. Introduction Inflammation is a protective mechanism of organisms to foods such as fruits and vegetables act as antioxidant and anti- remove injurious stimuli from the tissues, and is involved in the inflammatory agents by quenching free radicals, increasing development of several diseased conditions or disorders. Long- antioxidant defenses, or inhibiting the release of pro-inflammatory term administration of nonsteroidal anti-inflammatory drugs mediators (Chou et al., 2012). Studies focused on finding (NSAIDs) may induce numerous adverse effects, including gastro- antioxidant and anti-inflammatory agents with selective intestinal ulcers, bleeding, and renal disorders because of their pharmacology and less toxicity from natural plants have becomes a nonselective inhibition of both constitutive cyclooxygenase-1 major focus of scientific research worldwide. (COX-1) and inducible (COX-2) isoforms of the enzymes (Pendota The jujube fruits are known as a predominantly nutritious food et al., 2014). Moreover, new clinical and epidemiological data due to their biologically active components such as triterpenic consider the oxidative stress as an important determinant in the acids, flavonoids, phenolic acids, and vitamins (Gao et al., 2013). development of chronic inflammation (Bekir et al., 2013). Natural Various parts of the jujube plant have been traditionally used for *To whom correspondence should be addressed. E-mail: [email protected] 418 X. LI et al. the treatment of different kinds of diseases. The fruits and seeds ethanol to give the crude extract (CE) at a temperature below 45℃. have been traditionally applied to treat various diseases such as The CE was suspended in distilled water (10 L) and partitioned anorexia, lassitude, insomnia, anxiety, loose stools, insufficiency of successively with petroleum ether (PE, bp 60 _ 90℃, 5×10 L), the spleen, and fatigue in women (Mahajan et al., 2009; Guo et al., ethyl acetate (EtOAc or EA, 6×10 L), and water-saturated n-butanol 2011; Yu et al., 2012). (n-BuOH, 7×10 L) to obtain PE extract (151.0 g), EA extract Numerous previous studies have focused on different jujube (212.0 g), and n-BuOH (1036.0 g) fraction, respectively. The species and revealed that the antioxidant capacities of jujube can be extracts were stored at 4℃ for further analysis. attributed to the high level of polyphenols, flavonoids, and Separation and isolation of the active compounds The PE anthocyanins; and this activity differs with cultivars, tissues, fraction (125.0 g) was subjected to silica gel column ripening stages. The predominant phenolic acid in jujube was chromatography (CC) and eluted with a gradient of PE-EtOAc shown to be protocatechuic acid, followed by gallic acid, (100:0 to 0:100, V/V) to yield 20 fractions (Fr.A-Fr.T). Using re- chlorogenic acid and caffeic acid (Zhang et al., 2010; Zozio et al., chromatography on a silica gel CC, fraction G (5.8 g) was separated 2014). Jujube is usually used as an antidote in a traditional Chinese by PE-EtOAc (100:6 to 80:20, V/V) on a silica gel CC to give 33 formula, Shi Zao decoction, to relieve the drastic inflammatory fractions. Subsequently, fraction 3 and fractions 8 _ 15 were irritant nature of Euphorbia species. Previous study (Yu et al., submitted to recrystallization with EtOAc to obtain compound 7 2012) demonstrated that the triterpene acids fraction is the most (ursonic acid, 90 mg) and compound 1 (stigmasterol, 257 mg), active part causing the inhibitory effects on the inflamed cells after respectively. Fraction I (5.5 g) was chromatographed on a silica gel activation by Euphorbia kansui and prostratin. CC eluted with a stepwise system PE-EtOAc (95:5 to 70:30, V/V) As we know, previous studies of Ziziphus jujuba Mill. cv. to obtain compound 3 (betulinic acid, 272 mg). Fraction K (3.2 g) jinsixiaozao Hort. (ZJMH), widely cultivated in China, were was further subjected to a silica gel CC, eluted with PE-EtoAc mainly focused on its polysaccharides. Therefore, the objectives of (100:6 to 80:20, V/V) to obtain fractions 19 _ 27, which was this study were to investigate the antioxidant and anti-inflammatory further chromatographed on Sephadex LH-20 CC by elution with capacities and their active constituents (phenolic acids, flavonoids, CH2Cl2:methanol (1:1, V/V) to yield pure compound 4 (ursolic triterpenes, anthocyanins, triterpenoid saponins) of different acid, 83 mg). Fraction P (4.9 g) was chromatographed on a silica extracts. Moreover, the anti-inflammatory activities of the gel CC eluted with PE-EtOAc (80:20 to 70:30, V/V, stepwise) to compounds isolated from this fruit were also evaluated. give 2 fractions, then these 2 fractions were further chromatographed to yield a white powder (compound 6, alphitolic Material and Methods acid, 230 mg). compound 2 (oleanonic acid, 730 mg) was obtained Material and reagents The fruits of ZJMH were purchased in as a colorless needle crystal from fraction H by recrystallization Cangzhou City, Hebei Province of China, and identified by from methanol, while compound 5 (ceanothic acid, 30 mg) was Professor Wenyuan Gao (School of Pharmaceutical Science and from fraction N by recrystallization by EtOAc. Technology, Tianjin University, Tianjin, China). The voucher The isolated compounds were identified on the basis of their specimens were deposited at 4℃ in a laboratory of Tianjin spectroscopic data (1H-NMR, 13C-NMR, and LC–MS) (Online University. Resource ESM_1), allied to their physical characteristics, compared Ascorbic acid, gallic acid (Nr. 110831-200803), rutin (Nr. to previous publications. 100080-200707), oleanolic acid, and jujuboside B were purchased Animals Kunming mice (6 _ 8 weeks, about 18 _ 22 g) were from the National Institute for the Control of Pharmaceutical and procured from the Institute of Tianjin Laboratory Animal Center, Biological Products (Beijing, China). Carrageenan (Nr. C1867), Tianjin. They were fed with a rodent standard pellet diet with free β-carotene (reference standard, purity ≥99.0%), and 1,1-diphenyl- access to water ad libitum and kept at 25 ± 1℃ under a 12 h light/ 2-picrylhydrazyl (DPPH) were obtained from Sigma Chemical Co. dark cycle condition. The Animal Ethics Committees of the Faculty (St. Louis, Mo., USA). Linoleic acid, Twain 20, and Folin- of Medicine approved all experimental protocols, in accordance Ciocalteu’s reagent were provided by Guangfu Fine Chemical with ‘Principles of Laboratory Animal Care and Use in Research’ Research Inst. (Tianjin, China). Xylene was purchased from Tanjin (Ministry of Health, Beijing, China). Yingda Rare Chemical Reagents Factory (Tianjin, China). Analyses of functional components Dexamethasone (DEX) was obtained from Lisheng Pharmaceutical Determination of total polyphenols The total polyphenols Co., Ltd (Tianjin, China). Other chemicals used in the experiment (TPs) content in the PE, EA, and n-BuOH extracts of the JZMH were of analytical grade. was determined using Folin–Ciocalteu’s reagent (Zhang et al., Extraction and solvent fraction The air-dried fruits of ZJMH 2013). The TPs content was calculated from the calibration curve (24.1 kg) with the seeds were chipped and extracted with 95% (1:8, of gallic acid ranged from 20 to 100 μg. w/v) and 65% (1:8, w/v) ethanol three times (each for 2 h) under Determination of total flavonoids The total flavonoids (TFs) reflux. The combined extract was evaporated in vacuo to remove content was measured using the aluminum chloride colorimetric Biological Phytochemical Study of Jujube Fruits 419 method outlined by Zhang et al. (2013) with
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