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Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
Bioorg Med Chem. 2014 Apr 01; 22(7):2236-43.BM

Abstract

The high mutation rate of RNA viruses has resulted in limitation of vaccine effectiveness and increased emergence of drug-resistant viruses. New effective antivirals are therefore needed to control of the highly mutative RNA viruses. The n-butanol fraction of the stem bark of Mangifera indica exhibited inhibitory activity against influenza neuraminidase (NA) and coxsackie virus 3C protease. Bioassay guided phytochemical study of M. indica stem bark afforded two new compounds including one benzophenone C-glycoside (4) and one xanthone dimer (7), together with eleven known compounds. The structures of these isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Anti-influenza and anti-coxsackie virus activities were evaluated by determining the inhibition of anti-influenza neuraminidase (NA) from pandemic A/RI/5+/1957 H2N2 influenza A virus and inhibition of coxsackie B3 virus 3C protease, respectively. The highest anti-influenza activity was observed for compounds 8 and 9 with IC50 values of 11.9 and 9.2μM, respectively. Compounds 8 and 9 were even more potent against coxsackie B3 virus 3C protease, with IC50 values of 1.1 and 2.0μM, respectively. Compounds 8 and 9 showed weak cytotoxic effect against human hepatocellular carcinoma and human epithelial carcinoma cell lines through MTT assay.

Authors+Show Affiliations

CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China; Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, PR China.Protein Research Chair, Department of Biochemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi Arabia.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China; School of Life Sciences, Anhui University, Hefei 230601, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China. Electronic address: liuxueting_cn@hotmail.com.Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. Electronic address: hanaa.sayed@gmail.com.CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China. Electronic address: zhanglixin@im.ac.cn.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24613627

Citation

Abdel-Mageed, Wael M., et al. "Benzophenone C-glucosides and Gallotannins From Mango Tree Stem Bark With Broad-spectrum Anti-viral Activity." Bioorganic & Medicinal Chemistry, vol. 22, no. 7, 2014, pp. 2236-43.
Abdel-Mageed WM, Bayoumi SA, Chen C, et al. Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorg Med Chem. 2014;22(7):2236-43.
Abdel-Mageed, W. M., Bayoumi, S. A., Chen, C., Vavricka, C. J., Li, L., Malik, A., Dai, H., Song, F., Wang, L., Zhang, J., Gao, G. F., Lv, Y., Liu, L., Liu, X., Sayed, H. M., & Zhang, L. (2014). Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. Bioorganic & Medicinal Chemistry, 22(7), 2236-43. https://doi.org/10.1016/j.bmc.2014.02.014
Abdel-Mageed WM, et al. Benzophenone C-glucosides and Gallotannins From Mango Tree Stem Bark With Broad-spectrum Anti-viral Activity. Bioorg Med Chem. 2014 Apr 1;22(7):2236-43. PubMed PMID: 24613627.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity. AU - Abdel-Mageed,Wael M, AU - Bayoumi,Soad A H, AU - Chen,Caixia, AU - Vavricka,Christopher J, AU - Li,Li, AU - Malik,Ajamaluddin, AU - Dai,Huanqin, AU - Song,Fuhang, AU - Wang,Luoqiang, AU - Zhang,Jingyu, AU - Gao,George F, AU - Lv,Yali, AU - Liu,Lihong, AU - Liu,Xueting, AU - Sayed,Hanaa M, AU - Zhang,Lixin, Y1 - 2014/02/20/ PY - 2013/12/08/received PY - 2014/01/30/revised PY - 2014/02/11/accepted PY - 2014/3/12/entrez PY - 2014/3/13/pubmed PY - 2014/12/15/medline KW - Anacardiaceae KW - Benzophenone C-glucosides KW - Coxsackie protease inhibitors KW - Cytotoxic effect KW - Gallotannins KW - Mangifera indica KW - Mangiferin dimmer KW - Neuraminidase inhibitors KW - Xanthones SP - 2236 EP - 43 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 22 IS - 7 N2 - The high mutation rate of RNA viruses has resulted in limitation of vaccine effectiveness and increased emergence of drug-resistant viruses. New effective antivirals are therefore needed to control of the highly mutative RNA viruses. The n-butanol fraction of the stem bark of Mangifera indica exhibited inhibitory activity against influenza neuraminidase (NA) and coxsackie virus 3C protease. Bioassay guided phytochemical study of M. indica stem bark afforded two new compounds including one benzophenone C-glycoside (4) and one xanthone dimer (7), together with eleven known compounds. The structures of these isolated compounds were elucidated on the basis of spectroscopic evidences and correlated with known compounds. Anti-influenza and anti-coxsackie virus activities were evaluated by determining the inhibition of anti-influenza neuraminidase (NA) from pandemic A/RI/5+/1957 H2N2 influenza A virus and inhibition of coxsackie B3 virus 3C protease, respectively. The highest anti-influenza activity was observed for compounds 8 and 9 with IC50 values of 11.9 and 9.2μM, respectively. Compounds 8 and 9 were even more potent against coxsackie B3 virus 3C protease, with IC50 values of 1.1 and 2.0μM, respectively. Compounds 8 and 9 showed weak cytotoxic effect against human hepatocellular carcinoma and human epithelial carcinoma cell lines through MTT assay. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/24613627/Benzophenone_C_glucosides_and_gallotannins_from_mango_tree_stem_bark_with_broad_spectrum_anti_viral_activity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(14)00120-5 DB - PRIME DP - Unbound Medicine ER -