Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations
Lv, Jun-Jiang1,2; Yu, Shan1,2; Wang, Ya-Feng3; Wang, Dong1; Zhu, Hong-Tao1; Cheng, Rong-Rong1; Yang, Chong-Ren1; Xu, Min1; Zhang, Ying-Jun1; Xu,M (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Peoples R China.; minxu@mail.kib.ac.cn; zhangyj@mail.kib.ac.cn
2014-06-20
发表期刊JOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
卷号79期号:12页码:5432-5447
摘要Nineteen new highly oxygenated norbisabolane sesquiterpenoids, phyllanthacidoid acid methyl ester (1), and C-T (4-21), were isolated from Phyllanthus acidus Skeels, together with two known ones, phyllanthusols A (2) and B (3), whose sugar moiety was revised as glucosamine-N-acetate, rather than the previously assigned mannosamine-N-acetate. Compounds 2 and 3 were renamed respectively as phyllanthacidoids A (2) and B (3) to avoid confusion. All of the isolates except for 1 are glycosides, whose saccharide moieties possess a pentaoxy cyclohexane (scyllo quercitol) connecting with glucosamine-N-acetate or glucosyl moieties, which are first examples in natural products. Phyllanthacidoids N-R (15-19) with 8R configurations and/or 5,8-diketal skeleton, are unprecedented structures among norbisabolane sesquiterpenoids. Phyllanthacidoids S (20) and T (21) have the unusual tricyclo [3.1.1.1] oxygen bridge skeleton formed by a diketal system, of which the relative configurations of the aliphatic chain were assigned on the basis of heteronuclear coupling constants. The absolute configurations of compounds (1-21) were established by means of calculated electronic circular dichroism (ECD) and coupling constants. Compounds 1-5, 7-9, 10, and 14 displayed potential anti-hepatitis B virus (HBV) activities, with IC50 values of 0.8-36 mu M against HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg), and the results indicated that the S-ketal group and sugar moieties had contributions to the selectivity of HBsAg and HBeAg.
关键词Antineoplastic Agents Acuminatus Vahl Glycosides Emblica Roots Secretion Norsesquiterpenoids Pyrimidine Inhibitors
资助信息NSFC [21002105];973 Program of Ministry of Science and Technology of P. R. China [2011CB915503];12th Five Year National Science & Technology Supporting Program [2012BAI29B06];Fourteenth Candidates of the Young Academic Leaders of Yunnan Province [2011CI044];West Light Foundation of the Chinese Academy of Sciences
学科领域Chemistry, Organic
DOI10.1021/jo5004604
收录类别SCI ; IC
语种英语
WOS研究方向Chemistry
WOS类目Chemistry, Organic
WOS记录号WOS:000337871100005
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/18192
专题植物化学与西部植物资源持续利用国家重点实验室
通讯作者Xu,M (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Peoples R China.; minxu@mail.kib.ac.cn; zhangyj@mail.kib.ac.cn
作者单位1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Zhengzhou Univ, Sch Pharmaceut Sci, Zhengzhou 450001, Peoples R China
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Lv, Jun-Jiang,Yu, Shan,Wang, Ya-Feng,et al. Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations[J]. JOURNAL OF ORGANIC CHEMISTRY,2014,79(12):5432-5447.
APA Lv, Jun-Jiang.,Yu, Shan.,Wang, Ya-Feng.,Wang, Dong.,Zhu, Hong-Tao.,...&zhangyj@mail.kib.ac.cn.(2014).Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations.JOURNAL OF ORGANIC CHEMISTRY,79(12),5432-5447.
MLA Lv, Jun-Jiang,et al."Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations".JOURNAL OF ORGANIC CHEMISTRY 79.12(2014):5432-5447.
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