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Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases.
Hou, Bo; Liu, Ze; Yang, Xiao-Bei; Zhu, Wen-Fei; Li, Jin-Yu; Yang, Liu; Reng, Fu-Cai; Lv, Yong-Feng; Hu, Jiang-Miao; Liao, Guo-Yang; Zhou, Jun.
Afiliación
  • Hou B; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People
  • Liu Z; The Fifth Department of Biological Products, Institute of Medical Biology, Chinese Academy of Medical Science and Peking Union Medical College, Kunming, People's Republic of China.
  • Yang XB; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People
  • Zhu WF; National Institute for Viral Disease Control and Prevention, Chinese Centre for Disease Control and Prevention, China.
  • Li JY; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People
  • Yang L; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China.
  • Reng FC; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People
  • Lv YF; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People
  • Hu JM; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China. Electronic address: hujiangmiao@mail.kib.ac.cn.
  • Liao GY; The Fifth Department of Biological Products, Institute of Medical Biology, Chinese Academy of Medical Science and Peking Union Medical College, Kunming, People's Republic of China. Electronic address: mybelieze@126.com.
  • Zhou J; State Key Laboratory of Phytochemistry and Plant Resources in West China, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People' s Republic of China. Electronic address: jzhou@mail.kib.ac.cn.
Bioorg Med Chem ; 27(17): 3846-3852, 2019 09 01.
Article en En | MEDLINE | ID: mdl-31324565
The stems of Dryopteris crassirhizoma, one of the main components of Lianhua-Qingwen Formula (LQF) was traditionally used for heat-clearing and detoxifying. Dryocrassin ABBA is a key antiviral component in the herbal medicine while the compound is hard to get in large amounts with the features of homologous compounds, polyphenol groups, and low contents. Therefore, the present work aims to seek influenza H7N9 virus inhibitors from natural source by synthesis of dryocrassin ABBA and its analogues. As a result, total synthesis of the compound was achieved in nine steps with an over-all yield of 4.6%. Neuraminidases (NAs) inhibitory activities of the synthesized product and its analogues were evaluated afterward. Comparing with the positive control, OSV (9.6 µM), it was very exciting that dryocrassin ABBA and its analogues (b5 and e2) showed better NAs inhibitory activity against Anhui H7N9 with IC50 values of 3.6 µM, 2.5 µM and 1.6 µM. For the highly resistant Shanghai N9, these compounds can also show medium inhibitory activities. Docking results indicated the direct interaction of synthesized 3 hits with the key K294 by hydrogen bonds, but no direct interaction of OSV with the key K294 was observed in Shanghai N9. This study suggested that dryocrassin ABBA and its analogues especially AB, which consisted of polyphenol groups may have beneficial effects on treating avian influenza H7N9 virus.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / Compuestos de Bencilideno / Ciclohexanonas / Farmacorresistencia Viral / Inhibidores Enzimáticos / Subtipo H7N9 del Virus de la Influenza A / Neuraminidasa Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Antivirales / Compuestos de Bencilideno / Ciclohexanonas / Farmacorresistencia Viral / Inhibidores Enzimáticos / Subtipo H7N9 del Virus de la Influenza A / Neuraminidasa Idioma: En Revista: Bioorg Med Chem Asunto de la revista: BIOQUIMICA / QUIMICA Año: 2019 Tipo del documento: Article Pais de publicación: Reino Unido