JOURNAL OF SHANDONG UNIVERSITY (HEALTH SCIENCES) ›› 2017, Vol. 55 ›› Issue (8): 35-41.doi: 10.6040/j.issn.1671-7554.0.2017.070

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Isolation and identification of phenolic constituents from Viscum coloratum and the antiproliferative effects on A549 cells

HUANG Zhuqing, WU Xuewei, REN Dongmei   

  1. Key Lab of Chemical Biology(Ministry of Education), School of Pharmaceutical Sciences, Shandong University, Jinan 250012, Shandong, China
  • Received:2017-01-18 Online:2017-08-10 Published:2017-08-10

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Abstract: Objective To isolate and purify the chemical constituents of the active fraction from Viscum coloratum, and to evaluate the apoptotic effects on A549 cells. Methods Various chromatographic methods including silica gel, sephadex LH-20 column chromatography were used for the purification of chemical constituents from the extracts of Viscum coloratum. Spectroscopic methods including NMR and MS were used for the structural elucidation of the compounds. The antiproliferative effects were evaluated by MTT assay. Flow cytometry was used for the determination of cell cycle, apoptosis and intracellular reactive oxygen species(ROS)level. Western blotting analysis was carried out for the detection of protein expression. Results Ten phenolic compounds were obtained from Viscum coloratum. Compound 1 was identified as 1,7-di-(4-hydroxyphenyl)-4E,6E-heptadiene-3-ketone. This compound exerted cytotoxicity on A549 cells dose-dependently(F=196.768, P=0.001). It increased the cell number in G2/M phase(P<0.05)and decreased the cell number in S phase(P<0.05). The intracellular ROS level induced by compound 1 increased significantly(P<0.05). The compound also induced apoptosis of A549 cells. The expressions of Caspase-9, Caspase-3 and PARP were changed under the treatment(F: 19.340, 4.388, 194.571; P: 0.001, 0.042, 0.001). Conclusion Diphenylheptanes and flavonoids are the main phenolic components of Viscum coloratum, and diphenylheptanes are the main active ingredients of Viscum coloratum against lung cancer cell proliferation.

Key words: 1,7-di-(4-hydroxyphenyl)-4E,6E-heptadiene-3-ketone, Viscum coloratum, Lung neoplasm, A549 cells

CLC Number: 

  • R734.2
[1] 陶明煊, 吴国荣. 槲寄生的研究与开发利用[J]. 中国野生植物资源, 2002, 20(6): 14-15. TAO Mingxuan, WU Guorong. The research and development of Viscum coloratum(Kom.)Nakai[J]. Chinese Wild Plant Resources, 2002, 20(6): 14-15.
[2] 关玥, 孙长波, 李慧萍, 等. 槲寄生的化学成分及药理作用研究进展[J]. 上海中医药杂志, 2016, 50(5): 102-105. GUAN Yue, SUN Changbo, LI Huiping, et al. Advances on chemical constituent and pharmacology of Viscum coloratum(Kom.)Nakai[J]. Shanghai Journal of Traditional Chinese Medicine, 2016, 50(5): 102-105.
[3] 夏超, 郑马庆, 刘媛, 等. 槲寄生抗肿瘤有效成份提取及其对乳腺癌细胞的抑制作用[J]. 南京医科大学学报(自然科学版), 2016, 36(11): 1313-1315. XIA Chao, ZHEN Maqing, LIU Yuan, et al. Effective anti-tumor component separation of Viscum coloratum(kom)Nakai and its antitumor activity in breast cancer cells[J]. Acta Universitatis Medicinalis Nanjing(Natural Science), 2016, 36(11): 1313-1315.
[4] Tröger W, Galun D, Reif M, et al. Viscum album[L.] extract therapy in patients with locally advanced or metastatic pancreatic cancer: a randomised clinical trial on overall survival[J]. Eur J Cancer, 2013, 49(18): 3788-3797.
[5] Chai Y, Zhao M. Purification, characterization and anti-proliferation activities of polysaccharides extracted from Viscum coloratum (Kom.)Nakai[J]. Carbohydr Polym, 2016, 149: 121-130. doi: 10.1016/j.carbpol.2016.04.090.
[6] Kang SN. Ethanol extracts from mistletoe(Viscum album L.)act as natural antioxidants and antimicrobial agents in uncooked pork patties during refrigerated storage[J]. Asian-Australas J Anim Sci, 2016, 29(1): 109-118.
[7] Kim JJ, Hwang YH, Kang KY, et al. Enhanced dendritic cell maturation by the B-chain of Korean mistletoe lectin(KML-B), a novel TLR4 agonist[J]. Int Immunopharmacol, 2014, 21(2): 309-319.
[8] 吴金义, 张爽, 张秀梅, 等. 槲寄生抗实验性心律失常的作用[J]. 中国老年学杂志, 2011, 15(31): 2933-2935.
[9] Ali MS, Tezuka Y, Awale S, et al. Six new diarylheptanoids from the seeds of Alpinia blepharocalyx[J]. J Nat Prod, 2001, 64(3): 289-293.
[10] Zhao YL, Wang XY, Sun LX, et al. Cytotoxic constituents of Viscum coloratum[J]. Z Naturforsch C, 2012, 67(3-4): 129-134.
[11] Dong SH, Nikolic D, Simmler C, et al. Diarylheptanoids from Dioscorea villosa(Wild Yam)[J]. J Nat Prod, 2012, 75(12): 2168-2177.
[12] Shin D, Kinoshita K, Koyama K, et al. Antiemetic principles of Alpinia officinarum[J]. J Nat Prod, 2002, 65(9): 1315-1318.
[13] 杨小唯, 黄敏珠, 赵卫权, 等. 中药鬼针草化学成分的研究[J]. 解放军药学学报, 2009, 25(4): 283-286. YANG Xiaowei, HUANG Minzhu, ZHAO Weiquan, et al. Studies on chemical constituents of Bidens Bipinnata[J]. Pharmaceutical Journal of Chinese Peoples Liberation Army, 2009, 25(4): 283-286.
[14] 孙永慧, 凌勇, 任美荣, 等. 红果槲寄生的化学成分研究[J]. 中草药, 2010, 41(9): 1418-1420. SUN Yonghui, LING Yong, REN Meirong, et al. Chemical constituents of Viscum coloratum f. rubroaurantiacum[J]. Chinese Traditional and Herbal Drugs, 2010, 41(9): 1418-1420.
[15] 谢春英, 林乐维. 猴耳环化学成分研究[J]. 中药材, 2011, 34(7): 1060-1062. XIE Chunying, LIN Lewei. Study on the chemical constituents of Pithecellobium clypearia[J]. Journal of Chinese Medicinal Materials, 2011, 34(7): 1060-1062.
[16] Ibrahim AR, Galal AM, Ahmed MS, et al. O-demethylation and sulfation of 7-methoxylated flavanones by Cunninghamella elegans[J]. Chem Pharm Bull, 2003, 51(2): 203-206.
[17] Xue Y, Xu XM, Yan JF, et al. Chemical constituents from Astilbe chinensis[J]. J Asian Nat Prod Res, 2011, 13(2): 188-191.
[18] 汪琼, 罗士德, 徐永艳. 桂火绳中化学成分的研究[J]. 天然产物研究与开发, 2012, 24(3): 285-290. WANG Qiong, LUO Shide, XU Yongyan. Chemical constituents of Eriolaena kwangsiensis Hand.-Mazz.[J]. Nat Prod Res Dev, 2012, 24(3): 285-290.
[19] 曹朵, 翁志洁, 李建其, 等. 槲寄生属植物化学成分及药理活性研究进展[J]. 中草药, 2015, 46(10): 1562-1570. CAO Duo, WENG Zhijie, LI Jianqi, et al. Research progress on chemical constituents in plants from Viscum L. and their pharmacological activities[J]. Chinese Traditional and Herbal Drugs, 2015, 46(10): 1562-1570.
[20] 孔凡青, 吕学谦, 杨艳红. 槲寄生抗肿瘤作用研究[J]. 科技信息, 2010, 2010(19): 820-821.
[21] 孙莉, 姚俊涛, 王一羽, 等. 槲寄生碱抑制肺癌细胞增殖作用初步观察[J]. 中华肿瘤防治杂志, 2013, 20(21): 1653-1656. SUN Li, YAO Juntao, WANG Yiyu, et al. Inhibitory effects of mistletoe alkali on human lung adenocarcinoma SPC-A1 and squamous SK-MES-1 cells[J]. 2013, 20(21): 1653-1656.
[22] Kim WH, Park WB, Gao B, et al. Critical role of reactive oxygen species and mitochondrial membrane potential in Korean mistletoe lectin-induced apoptosis in human hepatocarcinoma cells[J]. Mol Pharmacol, 2004, 66(6): 1383-1396.
[23] 孔景临, 杜秀宝, 范崇旭, 等. 一种槲寄生多肽的一级结构分析和抗肿瘤活性[J]. 药学学报, 2004, 39(10): 813-817. KONG Jinglin, DU Xiubao, FAN Chongxu, et al. Determination of primary structure of a novel peptide from mistletoe and its antitumor activity[J]. Acta Pharmaceutica Sinica, 2004, 39(10): 813-817.
[24] Zhao L, Wen Q, Yang G, et al. Apoptosis induction of dehydrobruceine B on two kinds of human lung cancer cell lines through mitochondrial-dependent pathway[J]. Phytomedicine, 2016, 23(2): 114-122.
[25] Thannickal VJ, Fanburg BL. Reactive oxygen species in cell signaling[J]. Am J Physiol-Lung C, 2000, 279(6): L1005-1028.
[26] Vakifahmetoglu-Norberg H, Ouchida AT, Norberg E. The role of mitochondria in metabolism and cell death[J]. Biochem Biophys Res Commun, 2017, 482(3): 426-431.
[27] 赵瑞杰, 李引乾, 王会, 等. Caspase家族与细胞凋亡的关系[J]. 中国畜牧杂志, 2010, 46(17): 73-78.
[28] Fiandalo MV, Kyprianou N. Caspase control: protagonists of cancer cell apoptosis[J]. Exp Oncol, 2012, 34(3): 165-175.
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