title: Benzophenone C-glucosides and gallotannins from mango tree stem bark with broad-spectrum anti-viral activity.
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.affiliation: 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.
authors.forename: Wael M
authors.initials: WM
authors.lastname: Abdel-Mageed
authors.affiliation: Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt.
authors.forename: Soad A H
authors.initials: SA
authors.lastname: Bayoumi
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Caixia
authors.initials: C
authors.lastname: Chen
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Vavricka
authors.affiliation: Department of Medicinal Chemistry, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, PR China.
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.affiliation: Protein Research Chair, Department of Biochemistry, College of Sciences, King Saud University, Riyadh 11451, Saudi Arabia.
authors.forename: Ajamaluddin
authors.initials: A
authors.lastname: Malik
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Huanqin
authors.initials: H
authors.lastname: Dai
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Fuhang
authors.initials: F
authors.lastname: Song
authors.affiliation: 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.
authors.forename: Luoqiang
authors.initials: L
authors.lastname: Wang
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: Jingyu
authors.initials: J
authors.lastname: Zhang
authors.affiliation: CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100190, PR China.
authors.forename: George F
authors.initials: GF
authors.lastname: Gao
authors.affiliation: Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.
authors.forename: Yali
authors.initials: Y
authors.lastname: Lv
authors.affiliation: Beijing Chao-Yang Hospital Affiliated with Beijing Capital Medical University, Beijing 100020, PR China.
authors.forename: Lihong
authors.initials: L
authors.lastname: Liu
authors.affiliation: 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.
authors.forename: Xueting
authors.initials: X
authors.lastname: Liu
authors.affiliation: Pharmacognosy Department, Faculty of Pharmacy, Assiut University, Assiut 71526, Egypt. Electronic address: hanaa.sayed@gmail.com.
authors.forename: Hanaa M
authors.initials: HM
authors.lastname: Sayed
authors.affiliation: 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.
authors.forename: Lixin
authors.initials: L
authors.lastname: Zhang
mesh_terms: D000086042:3C Viral Proteases; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D001577:Benzophenones / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D003546:Cysteine Endopeptidases / Q000378:metabolism; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D029822:Enterovirus B, Human / Q000201:enzymology; D006367:HeLa Cells; D056945:Hep G2 Cells; D006801:Humans; D047348:Hydrolyzable Tannins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D009980:Influenza A virus / Q000187:drug effects*; D031022:Mangifera / Q000737:chemistry*; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011480:Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014764:Viral Proteins / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D000998:Antiviral Agents; D001577:Benzophenones; D047348:Hydrolyzable Tannins; D011480:Protease Inhibitors; D014764:Viral Proteins; D003546:Cysteine Endopeptidases; D000086042:3C Viral Proteases
keywords: Anacardiaceae; Benzophenone C-glucosides; Coxsackie protease inhibitors; Cytotoxic effect; Gallotannins; Mangifera indica; Mangiferin dimmer; Neuraminidase inhibitors; Xanthones