Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations

doi:10.1021/jo5004604

	Anti-Hepatitis B Virus Norbisabolane Sesquiterpenoids from Phyllanthus acidus and the Establishment of Their Absolute Configurations Using Theoretical Calculations
	Lv, Jun-Jiang 1,2; Yu, Shan1,2 ; Wang, Ya-Feng 3; Wang, Dong1 ; Zhu, Hong-Tao 1; Cheng, Rong-Rong1 ; Yang, Chong-Ren 1; Xu, Min 1; 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
ISSN	0022-3263
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
学科领域	Chemistry, Organic
DOI	10.1021/jo5004604
收录类别	SCI ; IC
语种	英语
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
推荐引用方式 GB/T 7714	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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