Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases
Hou, Bo1,2,5; Liu, Ze3,4; Yang, Xiao-Bei1,2,5; Zhu, Wen-Fei6; Li, Jin-Yu1,2,5; Yang, Liu1,2; Reng, Fu-Cai1,2,5; Lv, Yong-Feng1,2,5; Hu, Jiang-Miao1,2; Liao, Guo-Yang3,4; Zhou, Jun1,2
Corresponding AuthorHu, Jiang-Miao(hujiangmiao@mail.kib.ac.cn) ; Liao, Guo-Yang(mybelieze@126.com) ; Zhou, Jun(jzhou@mail.kib.ac.cn)
2019-09-01
Source PublicationBIOORGANIC & MEDICINAL CHEMISTRY
ISSN0968-0896
Volume27Issue:17Pages:3846-3852
AbstractThe 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 mu M), 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 mu M, 2.5 mu M and 1.6 mu M. 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.
KeywordDryocrassin ABBA Neuraminidase Total synthesis Shanghai H7N9 Anhui H7N9
DOI10.1016/j.bmc.2019.07.013
Indexed BySCI
Language英语
WOS Research AreaBiochemistry & Molecular Biology ; Pharmacology & Pharmacy ; Chemistry
WOS SubjectBiochemistry & Molecular Biology ; Chemistry, Medicinal ; Chemistry, Organic
WOS IDWOS:000477773100010
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/68197
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorHu, Jiang-Miao; Liao, Guo-Yang; Zhou, Jun
Affiliation1.Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming Inst Bot, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China
3.Chinese Acad Med Sci, Inst Med Biol, Dept Biol Prod 5, Kunming, Yunnan, Peoples R China
4.Peking Union Med Coll, Kunming, Yunnan, Peoples R China
5.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
6.Chinese Ctr Dis Control & Prevent, Natl Inst Viral Dis Control & Prevent, Beijing, Peoples R China
Recommended Citation
GB/T 7714
Hou, Bo,Liu, Ze,Yang, Xiao-Bei,et al. Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2019,27(17):3846-3852.
APA Hou, Bo.,Liu, Ze.,Yang, Xiao-Bei.,Zhu, Wen-Fei.,Li, Jin-Yu.,...&Zhou, Jun.(2019).Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases.BIOORGANIC & MEDICINAL CHEMISTRY,27(17),3846-3852.
MLA Hou, Bo,et al."Total synthesis of dryocrassin ABBA and its analogues with potential inhibitory activity against drug-resistant neuraminidases".BIOORGANIC & MEDICINAL CHEMISTRY 27.17(2019):3846-3852.
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