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Chemical constituents from Phyllanthus emblica and the cytoprotective effects on H2O2-induced PC12 cell injuries

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Abstract

Two new compounds (1–2), including a bisabolane-type sesquiterpenoid (1), one new diphenyl ether derivative (2), together with 23 known compounds (3–25), were isolated from the fruits of Phyllanthus emblica. Their structures were elucidated by detailed spectroscopic analysis. All the isolated compounds were screened for the DPPH scavenging effects and cytoprotective effects against H2O2 induced PC12 cells injury. Compounds 12–15 showed significant DPPH scavenging effects with the IC50 values in the range of 3.25–4.18 μM. Among these potential antioxidants, compound 14 improved the survival of PC12 cells after H2O2 exposure without showing any cytotoxicity at the tested concentrations.

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References

  • Adil, M.D., P. Kaiser, N.K. Satti, A.M. Zargar, R.A. Vishwakarma, and S.A. Tasduq. 2010. Effect of Emblica officinalis (fruit) against UVB-induced photo-aging in human skin fibroblasts. Journal of Ethnopharmacology 132: 109–114.

    Article  PubMed  Google Scholar 

  • Akhtar, M.S., A. Ramzan, A. Ali, and M. Ahmad. 2011. Effect of Amla fruit (Emblica officinalis Gaertn.) on blood glucose and lipid profile of normal subjects and type 2 diabetic patients. International Journal of Food Sciences and Nutrition 62: 609–616.

    Article  CAS  PubMed  Google Scholar 

  • Bajpai, M., A. Pande, S.K. Tewari, and D. Prakash. 2005. Phenolic contents and antioxidant activity of some food and medicinal plants. International Journal of Food Sciences and Nutrition 56: 287–291.

    Article  CAS  PubMed  Google Scholar 

  • Crispo, J.A., M. Piche, D.R. Ansell, J.K. Eibl, I.T. Tai, A. Kumar, G.M. Ross, and T.C. Tai. 2010. Protective effects of methyl gallate on H2O2-induced apoptosis in PC12 cells. Biochemical and Biophysical Research Communications 393: 773–778.

    Article  CAS  PubMed  Google Scholar 

  • Dang, G.K., R.R. Parekar, S.K. Kamat, A.M. Scindia, and N.N. Rege. 2011. Antiinflammatory activity of Phyllanthus emblica, Plumbago zeylanica and Cyperus rotundus in acute models of inflammation. Phytotherapy Research 25: 904–908.

    Article  CAS  PubMed  Google Scholar 

  • Deng, C.B., Q.J. Xie, and Z.T. Qu. 2009. Chemical composition of Phyllanthius emblica. China Pharmacy 20: 2120–2121.

    CAS  Google Scholar 

  • Ding, L.Q., and Q.Z. Du. 2011. Separation and identification of two functional components in purple sweet potato. Food Science 32: 74–77.

    CAS  Google Scholar 

  • El-Desouky, S.K., S.Y. Ryu, and Y.K. Kim. 2008. A new cytotoxic acylated apigenin glucoside from Phyllanthus emblica L. Natural Product Research 22: 91–95.

    Article  CAS  PubMed  Google Scholar 

  • Ito, J., F.R. Chang, H.K. Wang, Y.K. Park, M. Ikegaki, N. Kilgore, and K.H. Lee. 2001. Anti-AIDS agents. 48. 1 Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis. Journal of Natural Products 64: 1278–1281.

    Article  CAS  PubMed  Google Scholar 

  • Jenner, P. 2003. Oxidative stress in Parkinson’s disease. Annals of Neurology 53(Suppl 3): S26–S36. discussion S36-8.

    Article  CAS  PubMed  Google Scholar 

  • Jiang, T., Z. Huang, Y. Lin, Z. Zhang, D. Fang, and D.D. Zhang. 2010. The protective role of Nrf2 in streptozotocin-induced diabetic nephropathy. Diabetes 59: 850–860.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Jindal, A., D. Soyal, A. Sharma, and P.K. Goyal. 2009. Protective effect of an extract of Emblica officinalis against radiation-induced damage in mice. Integrative Cancer Therapies 8: 98–105.

    Article  PubMed  Google Scholar 

  • Kim, H.J., T. Yokozawa, H.Y. Kim, C. Tohda, T.P. Rao, and L.R. Juneja. 2005. Influence of amla (Emblica officinalis Gaertn.) on hypercholesterolemia and lipid peroxidation in cholesterol-fed rats. Journal of Nutritional Science and Vitaminology 51: 413–418.

    Article  CAS  PubMed  Google Scholar 

  • Komai, S.I., T. Hosoe, T. Itabashi, K. Nozawa, T. Yaguchi, K. Fukushima, and K.-I. Kawai. 2006. New penicillide derivatives isolated from Penicillium simplicissimum. Journal of Natural Medicines 60: 185–190.

    Article  CAS  Google Scholar 

  • Kuo, Y.H., and C.I. Chang. 2000. Six new compounds from the heartwood of Diospyros maritima. Chemical & Pharmaceutical Bulletin 48: 1211–1214.

    Article  CAS  Google Scholar 

  • Luo, W., M. Zhao, B. Yang, G. Shen, and G. Rao. 2009. Identification of bioactive compounds in Phyllenthus emblica L. fruit and their free radical scavenging activities. Food Chemistry 114: 499–504.

    Article  CAS  Google Scholar 

  • Martin, K.R. 2006. Targeting apoptosis with dietary bioactive agents. Experimental Biology and Medicine 231: 117–129.

    CAS  PubMed  Google Scholar 

  • Matsuda, N., and M. Kikuchi. 1996. Studies on the constituents of Lonicera species. X. Neolignan glycosides from the leaves of Lonicera gracilipes var. glandulosa MAXIM. Chemical & Pharmaceutical Bulletin 44: 1676–1679.

    Article  CAS  Google Scholar 

  • Na, C.S., S.S. Hong, Y.H. Choi, Y.H. Lee, S.H. Hong, J.Y. Lim, B.H. Kang, S.Y. Park, and D. Lee. 2010. Neuroprotective effects of constituents of Eragrostis ferruginea against Abeta-induced toxicity in PC12 cells. Archives of Pharmacal Research 33: 999–1003.

    Article  CAS  PubMed  Google Scholar 

  • Nain, P., V. Saini, S. Sharma, and J. Nain. 2012. Antidiabetic and antioxidant potential of Emblica officinalis Gaertn. Leaves extract in streptozotocin-induced type-2 diabetes mellitus (T2DM) rats. Journal of Ethnopharmacology 142: 65–71.

    Article  CAS  PubMed  Google Scholar 

  • Nampoothiri, S.V., A. Prathapan, O.L. Cherian, K.G. Raghu, V.V. Venugopalan, and A. Sundaresan. 2011. In vitro antioxidant and inhibitory potential of Terminalia bellerica and Emblica officinalis fruits against LDL oxidation and key enzymes linked to type 2 diabetes. Food and Chemical Toxicology 49: 125–131.

    Article  CAS  PubMed  Google Scholar 

  • Nawwar, M.A.M., and A.M.A. Souleman. 1984. 3,4,8,9,10-Pentahydroxy-dibenzo[b,d]pyran-6-one from Tamarix nilotica. Phytochemistry 23: 2966–2967.

    Article  CAS  Google Scholar 

  • Park, J.A., H.J. Kim, C. Jin, K.T. Lee, and Y.S. Lee. 2003. A new pterocarpan, (-)-maackiain sulfate, from the roots of Sophora subprostrata. Archives of Pharmacal Research 26: 1009–1013.

    Article  CAS  PubMed  Google Scholar 

  • Park, J.B. 2011. Protective effects of veskamide, enferamide, becatamide, and oretamide on H2O2-induced apoptosis of PC-12 cells. Phytomedicine 18: 843–847.

    Article  CAS  PubMed  Google Scholar 

  • Poltanov, E.A., A.N. Shikov, H.J.D. Dorman, O.N. Pozharitskaya, V.G. Makarov, V.P. Tikhonov, and R. Hiltunen. 2009. Chemical and antioxidant evaluation of Indian gooseberry (Emblica officinalis gaertn., syn. phyllanthus emblica L.) supplements. Phytotherapy Research 23: 1309–1315.

    Article  CAS  PubMed  Google Scholar 

  • Proksa, B., D. Uhrin, J. Adamcova, and J. Fuska. 1992. Vermixocins A and B, two novel metabolites from Penicillium vermiculatum. The Journal of Antibiotics 45: 1268–1272.

    Article  CAS  PubMed  Google Scholar 

  • Ren, D., N.F. Villeneuve, T. Jiang, T. Wu, A. Lau, H.A. Toppin, and D.D. Zhang. 2011. Brusatol enhances the efficacy of chemotherapy by inhibiting the Nrf2-mediated defense mechanism. Proceedings of the National Academy of Sciences of the United States of America 108: 1433–1438.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • She, G., R. Cheng, L. Sha, Y. Xu, R. Shi, L. Zhang, and Y. Guo. 2013. A novel phenolic compound from Phyllanthus emblica. Natural Product Communications 8: 461–462.

    CAS  PubMed  Google Scholar 

  • Singh, I., D. Soyal, and P.K. Goyal. 2006. Emblica officinalis (Linn.) fruit extract provides protection against radiation-induced hematological and biochemical alterations in mice. Journal of Environmental Pathology, Toxicology and Oncology 25: 643–654.

    Article  PubMed  Google Scholar 

  • Srirama, R., H.B. Deepak, U. Senthilkumar, G. Ravikanth, B.R. Gurumurthy, M.B. Shivanna, C.V. Chandrasekaran, A. Agarwal, and R.U. Shaanker. 2012. Hepatoprotective activity of Indian Phyllanthus. Pharmaceutical Biology 50: 948–953.

    Article  CAS  PubMed  Google Scholar 

  • Sun, Y., Y. Ding, and W.H. Lin. 2009. Isolation and identification of compounds from marine mangrove plant Avicennia marina. Beijing Da Xue Xue Bao 41: 221–225.

    CAS  PubMed  Google Scholar 

  • Takara, K., D. Matsui, K. Wada, T. Ichiba, and Y. Nakasone. 2002. New antioxidative phenolic glycosides isolated from Kokuto non-centrifuged cane sugar. Bioscience, Biotechnology, and Biochemistry 66: 29–35.

    Article  CAS  PubMed  Google Scholar 

  • Thilakchand, K.R., R.T. Mathai, P. Simon, R.T. Ravi, M.P. Baliga-Rao, and M.S. Baliga. 2013. Hepatoprotective properties of the Indian gooseberry (Emblica officinalis Gaertn): a review. Food & Function 4: 1431–1441.

    Article  CAS  Google Scholar 

  • Ting, Y.C., H.H. Ko, H.C. Wang, C.F. Peng, H.S. Chang, P.C. Hsieh, and I.S. Chen. 2014. Biological evaluation of secondary metabolites from the roots of Myrica adenophora. Phytochemistry 103: 89–98.

    Article  CAS  PubMed  Google Scholar 

  • Tiwari, V., A. Kuhad, and K. Chopra. 2011. Emblica officinalis corrects functional, biochemical and molecular deficits in experimental diabetic neuropathy by targeting the oxido-nitrosative stress mediated inflammatory cascade. Phytotherapy Research 25: 1527–1536.

    Article  PubMed  Google Scholar 

  • Usharani, P., N. Fatima, and N. Muralidhar. 2013. Effects of Phyllanthus emblica extract on endothelial dysfunction and biomarkers of oxidative stress in patients with type 2 diabetes mellitus: a randomized, double-blind, controlled study. Diabetes, Metabolic Syndrome and Obesity 6: 275–284.

    PubMed  PubMed Central  Google Scholar 

  • Wang, L., X.J. Gong, X. Zhou, C. Xian, S.L. Yang, and Z.N. Yang. 2012. Chemical constituents of Psammosilene tunicoides and bacteriostatic activity. Zhongguo Zhong Yao Za Zhi 37: 3577–3580.

    CAS  PubMed  Google Scholar 

  • Wang, Q., and F.H. Xu. 2013. Chemical constituents of ethyl acetate fraction from Aeschynanthus bracteatus. Journal of Chinese Medicinal Materials 36: 414–415.

    CAS  PubMed  Google Scholar 

  • Wang, X.J., Z. Sun, W. Chen, K.E. Eblin, J.A. Gandolfi, and D.D. Zhang. 2007. Nrf2 protects human bladder urothelial cells from arsenite and monomethylarsonous acid toxicity. Toxicology and Applied Pharmacology 225: 206–213.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Wang, Y.C., Y.W. Zhang, L.H. Zheng, Y.L. Bao, Y. Wu, C.L. Yu, Y.X. Huang, L.G. Sun, Y. Zhang, and X.J. Jia. 2013. Four new alkaloids from the fermentation broth of Armillaria mellea. Helvetica Chimica Acta 96: 330–337.

    Article  Google Scholar 

  • Xia, X.K., F. Liu, Z.G. She, L.G. Yang, M.F. Li, L.L.P. Vrijmoed, and Y.C. Lin. 2008. 1H and 13C NMR assignments for 6-demethylvermistatin and two penicillide derivatives from the mangrove fungus Guignardia sp. (No. 4382) from the South China Sea. Magnetic Resonance in Chemistry 46: 693–696.

    Article  CAS  PubMed  Google Scholar 

  • Xiao, H.T., X.Y. Hao, X.W. Yang, Y.H. Wang, Y. Lu, Y. Zhang, S. Gao, H.P. He, and X.J. Hao. 2007. Bisabolane-type sesquiterpenoids from the rhizomes of Glochidion coccineum. Helvetica Chimica Acta 90: 164–170.

    Article  CAS  Google Scholar 

  • Yao, H.K., J.Y. Duan, Y. Li, J.H. Wang, X.X. Yin, and H.Q. Duan. 2011. Studies on the chemical constituents from the roots of Kalopanax septemlobus. Zhong Yao Cai 34: 716–718.

    CAS  PubMed  Google Scholar 

  • Yu, M., Z. Li, N. Li, and X. Li. 2008a. Chemical constituents of the aerial parts of Polygonum capitatum. Journal of Shenyang Pharmaceutical University 25: 633–635.

    CAS  Google Scholar 

  • Yu, Y., J.R. Du, C.Y. Wang, and Z.M. Qian. 2008b. Protection against hydrogen peroxide-induced injury by Z-ligustilide in PC12 cells. Experimental Brain Research 184: 307–312.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Y.J., T. Abe, T. Tanaka, C.R. Yang, and I. Kouno. 2001a. Phyllanemblinins A-F, new ellagitannins from Phyllanthus emblica. Journal of Natural Products 64: 1527–1532.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Y.J., T. Abe, T. Tanaka, C.R. Yang, and I. Kouno. 2002. Two new acylated flavanone glycosides from the leaves and branches of Phyllanthus emblica. Chemical & Pharmaceutical Bulletin 50: 841–843.

    Article  CAS  Google Scholar 

  • Zhang, Y.J., T. Tanaka, Y. Iwamoto, C.R. Yang, and I. Kouno. 2000. Novel norsesquiterpenoids from the roots of Phyllanthus emblica. Journal of Natural Products 63: 1507–1510.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Y.J., T. Tanaka, Y. Iwamoto, C.R. Yang, and I. Kouno. 2001b. Novel sesquiterpenoids from the roots of Phyllanthus emblica. Journal of Natural Products 64: 870–873.

    Article  CAS  PubMed  Google Scholar 

  • Zhang, Y.J., T. Tanaka, C.R. Yang, and I. Kouno. 2001c. New phenolic constituents from the fruit juice of Phyllanthus emblica. Chemical & Pharmaceutical Bulletin 49: 537–540.

    Article  CAS  Google Scholar 

  • Zhao, X.X., C.J. Zheng, and L.P. Qin. 2012. Chemical constituents from fruits of Vitex negundo. Chinese Traditional and Herbal Drugs 43: 2346–2350.

    CAS  Google Scholar 

  • Zhou, X., Y. Zhang, H. Liang, S. Huang, C. Wang, and A. Ping. 2012. Chemical constituents of Rhododendron lepidotum. Zhongguo Zhong Yao Za Zhi 37: 483–489.

    CAS  PubMed  Google Scholar 

  • Zhou, Y.Z., H. Chen, L. Qiao, D.F. Hao, H.M. Hua, and Y.H. Pei. 2007. Chemical constituents from Carthamus tinctorius L. Chinese Journal of Medicinal Chemistry 17: 380–382.

    CAS  Google Scholar 

  • Zuo, G., Z. Zhang, L. Chen, and X. Xu. 2005. Chemical constituents of Tibetan herbal medicine Saxifraga melanocentra. Acta Botanica Yunnanica 27: 691–694.

    CAS  Google Scholar 

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Acknowledgments

Financial support

Financial support from the National Natural Science Foundation of China (No. 81173528) and the Independent Innovation Foundation of Shandong University (No. 2012TS203) is gratefully acknowledged

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Authors and Affiliations

  1. Department of Natural Products Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 Wenhuaxi Road, Jinan, 250012, People’s Republic of China

    Yao Zhang, Lijuan Zhao, Xiaojiang Guo, Chao Li, Haizhen Li, Hongxiang Lou & Dongmei Ren

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  1. Yao Zhang
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  2. Lijuan Zhao
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  3. Xiaojiang Guo
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Correspondence to Dongmei Ren.

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Zhang, Y., Zhao, L., Guo, X. et al. Chemical constituents from Phyllanthus emblica and the cytoprotective effects on H2O2-induced PC12 cell injuries. Arch. Pharm. Res. 39, 1202–1211 (2016). https://doi.org/10.1007/s12272-014-0433-2

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