Stereochemistry of cleistanthane diterpenoid glucosides from Phyllanthus emblica
Lv, Jun-Jiang1,3; Yu, Shan1,2; Xin, Ying1,2; Zhu, Hong-Tao1; Wang, Dong1; 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.
2015
Source PublicationRSC ADVANCES
Volume5Issue:37Pages:29098-29107
AbstractTime-dependent density functional theory (TDDFT) calculated electronic circular dichroism (ECD) and Mosher's method were applied to establish the absolute configurations of six new highly oxygenated cleistanthane diterpenoid glucosides, phyllanembloids A-F (1-6), isolated from the roots of Phyllanthus emblica. Compounds 1-5 featured a carboxyl group at C-13 adjacent to the hydroxyl group at C-12, and are the first examples of cleistanthane diterpenoids with a salicylic acid fragment. The carboxyl group at C-13 can significantly affect the CD spectrum of cleistanthane diterpenoids, and make the excitations of phenylethylene dominate the Cotton effects (240 and 280 nm), rather than the benzene ring excitations dominating the Cotton effects at 220 and 240 nm as in the 13-methyl analogues. The characteristic Cotton effects of cleistanthane diterpenoids were summarized according to the experimental and calculated ECD curves, which can be applied as a common method to determine the absolute configurations of this type of diterpenoid.
Subject AreaChemistry, Multidisciplinary
DOI10.1039/c4ra16624h
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Multidisciplinary
WOS IDWOS:000352091600034
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/20596
Collection植物化学与西部植物资源持续利用国家重点实验室
Corresponding AuthorXu,M (reprint author),Chinese Acad Sci,Kunming Inst Bot,State Key Lab Phytochem & Plant Resources West Ch,Kunming 650201,Peoples R China.
Affiliation1.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.Chongqing Univ, Coll Chem & Chem Engn, Chongqing 400030, Peoples R China
Recommended Citation
GB/T 7714
Lv, Jun-Jiang,Yu, Shan,Xin, Ying,et al. Stereochemistry of cleistanthane diterpenoid glucosides from Phyllanthus emblica[J]. RSC ADVANCES,2015,5(37):29098-29107.
APA Lv, Jun-Jiang.,Yu, Shan.,Xin, Ying.,Zhu, Hong-Tao.,Wang, Dong.,...&Xu,M .(2015).Stereochemistry of cleistanthane diterpenoid glucosides from Phyllanthus emblica.RSC ADVANCES,5(37),29098-29107.
MLA Lv, Jun-Jiang,et al."Stereochemistry of cleistanthane diterpenoid glucosides from Phyllanthus emblica".RSC ADVANCES 5.37(2015):29098-29107.
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