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Density Functional Theory Calculations in Stereochemical Determination of Terpecurcumins J-W, Cytotoxic Terpene-Conjugated Curcuminoids from Curcuma longa L.
Lin, Xionghao1; Ji, Shuai1; Qiao, Xue1; Hu, Hongbo2; Chen, Ni2; Dong, Yinhui2; Huang, Yun1; Guo, Dean1; Tu, Pengfei1; Ye, Min1
刊名JOURNAL OF ORGANIC CHEMISTRY
2013-12-06
DOI10.1021/jo401859u
78期:23页:11835-11848
收录类别SCI ; IC
文章类型Article
WOS标题词Science & Technology
类目[WOS]Chemistry, Organic
研究领域[WOS]Chemistry
关键词[WOS]CHEMICAL-SHIFTS ; RHIZOMES ; COMPONENTS ; SHORTAGES
英文摘要

Fourteen novel terpene-conjugated curcuminoids, terpecurcumins J-W (1-14), have been isolated from the rhizomes of Curcuma longa L. Among them, terpecurcumins J-Q and V represent four unprecedented skeletons featuring an unusual core of hydrobenzannulated[6,6]-spiroketal (1 and 2), bicyclo[2.2.2]octene (3-7), bicyclo[3.1.3]octene (8), and spiroepoxide (13), respectively. The structures of compounds 1-14 were elucidated by extensive spectroscopic analysis, and their absolute configurations were established by electronic circular dichroism, vibrational circular dichroism, and C-13 NMR spectroscopic data analysis, together with density functional theory calculations. The structure and configuration of 1 was further confirmed by single-crystal X-ray diffraction (Cu K alpha). The biogenetic pathways of 1-14 were proposed, involving Michael addition, condensation, Diels-Alder cycloaddition, and electrophilic substitution reactions. Terpecurcumins showed more potent cytotoxic activities than curcumin and ar-/beta-turmerone. Among them, terpecurcumin Q (8) exhibited IC50 of 3.9 mu M against MCF-7 human breast cancer cells, and mitochondria-mediated apoptosis played an important role in the overall growth inhibition. Finally, LC/MS/MS quantitative analysis of five representative terpecurcumins indicated these novel compounds were present in C. longa at parts per million level.

语种英语
WOS记录号WOS:000328231600023
项目编号81222054 ; NCET-11-0019 ; 201307002
资助机构National Natural Science Foundation of China ; Program for New Century Excellent Talents in University from Chinese Ministry of Education ; China State Administration of TCM
引用统计
被引频次:19[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.bjmu.edu.cn/handle/400002259/55126
专题北京大学药学院
北京大学药学院_天然药物学系
作者单位1.Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
2.China Agr Univ, Coll Food Sci & Nutr Engn, Beijing 100083, Peoples R China
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GB/T 7714
Lin, Xionghao,Ji, Shuai,Qiao, Xue,et al. Density Functional Theory Calculations in Stereochemical Determination of Terpecurcumins J-W, Cytotoxic Terpene-Conjugated Curcuminoids from Curcuma longa L.[J]. JOURNAL OF ORGANIC CHEMISTRY,2013,78(23):11835-11848.
APA Lin, Xionghao.,Ji, Shuai.,Qiao, Xue.,Hu, Hongbo.,Chen, Ni.,...&Ye, Min.(2013).Density Functional Theory Calculations in Stereochemical Determination of Terpecurcumins J-W, Cytotoxic Terpene-Conjugated Curcuminoids from Curcuma longa L..JOURNAL OF ORGANIC CHEMISTRY,78(23),11835-11848.
MLA Lin, Xionghao,et al."Density Functional Theory Calculations in Stereochemical Determination of Terpecurcumins J-W, Cytotoxic Terpene-Conjugated Curcuminoids from Curcuma longa L.".JOURNAL OF ORGANIC CHEMISTRY 78.23(2013):11835-11848.
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