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题名: Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations
作者: Lv, Jun-Jiang1, 2; Yu, Shan1, 2; Wang, Ya-Feng3; Wang, Dong1; Zhu, Hong-Tao1; Cheng, Rong-Rong1; Yang, Chong-Ren1; Xu, Min1; null(张颖君)1
刊名: JOURNAL OF ORGANIC CHEMISTRY
关键词: ANTINEOPLASTIC AGENTS ; ACUMINATUS VAHL ; GLYCOSIDES ; EMBLICA ; ROOTS ; SECRETION ; NORSESQUITERPENOIDS ; PYRIMIDINE ; INHIBITORS
英文摘要: 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.
出版日期: 2014-06-20
卷号: 79, 期号:12, 页码:5432-5447
语种: 英语
收录类别: SCI ; IC
学科分类: Chemistry, Organic
ISSN号: 0022-3263
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/18192
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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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

Recommended Citation:
Lv,Jun-Jiang;Yu,Shan;Wang,Ya-Feng;Wang,Dong;Zhu,Hong-Tao;Cheng,Rong-Rong;Yang,Chong-Ren;Xu,Min;Zhang,Ying-Jun.Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations,JOURNAL OF ORGANIC CHEMISTRY,2014,79(12):5432-5447
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