Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

doi:10.1007/s13659-020-00273-x

应用天然产物 ›› 2021, Vol. 11 ›› Issue (1): 73-79.DOI: 10.1007/s13659-020-00273-x

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Yi Chen^2,3, Song-Wei Li¹, Fang-Zhou Yin¹, Min Yang¹, Xia-Juan Huan¹, Ze-Hong Miao¹, Xiao-Ming Wang^2,3, Yue-Wei Guo^1,4

1 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;
2 Hunan Academy of Forestry, 658 South Shao shan Road, Changsha 410004, Hunan, China;
3 Changsha Engineering Technology Research Center of Woody Flower, 658 South shao shan Road, Changsha 410004, Hunan, China;
4 College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shao shan Road, Changsha 410004, Hunan, China

收稿日期:2020-08-13 修回日期:2020-10-12 出版日期:2021-02-24 发布日期:2021-03-11
通讯作者: Xiao-Ming Wang, Yue-Wei Guo
基金资助:
This research work was financially supported by the National Natural Science Foundation of China (NSFC) (Nos. 81991521, 41676073), the National Key Research and Development Program of China (No. 2018YFC0310903), the Drug Innovation Major Project (No. 2018ZX09711-001-001-009), and the SKLDR/ SIMM Project (No. SIMM1903ZZ-04). Changsha Engineering Technology Research Center of Woody flower (kq1907081).

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Yi Chen^2,3, Song-Wei Li¹, Fang-Zhou Yin¹, Min Yang¹, Xia-Juan Huan¹, Ze-Hong Miao¹, Xiao-Ming Wang^2,3, Yue-Wei Guo^1,4

1 State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, China;
2 Hunan Academy of Forestry, 658 South Shao shan Road, Changsha 410004, Hunan, China;
3 Changsha Engineering Technology Research Center of Woody Flower, 658 South shao shan Road, Changsha 410004, Hunan, China;
4 College of Materials Science and Engineering, Central South University of Forestry and Technology, 498 South Shao shan Road, Changsha 410004, Hunan, China

Received:2020-08-13 Revised:2020-10-12 Online:2021-02-24 Published:2021-03-11
Contact: Xiao-Ming Wang, Yue-Wei Guo
Supported by:
This research work was financially supported by the National Natural Science Foundation of China (NSFC) (Nos. 81991521, 41676073), the National Key Research and Development Program of China (No. 2018YFC0310903), the Drug Innovation Major Project (No. 2018ZX09711-001-001-009), and the SKLDR/ SIMM Project (No. SIMM1903ZZ-04). Changsha Engineering Technology Research Center of Woody flower (kq1907081).

摘要/Abstract

摘要： A phytochemical investigation of the EtOH extract of the flowers of Lagerstroemia indica L. led to the isolation and characterization of a new pyrrole alkaloid, named lagerindicine (1), along with four known compounds (2-5). Their structures were elucidated by the detailed spectroscopic analysis and comparison with literature data, whereas the structure, in particularly, the absolute configuration (AC) of 1, was firmly determined by total synthesis. All the isolates were evaluated for their cytotoxic effects against human colon cancer cell (HCT-116), and compound 3 exhibited weak cytotoxicity with IC₅₀ value of 28.4 μM.

关键词: Lagerstroemia indica Linnaeus, Pyrrole alkaloid, Total synthesis, Stereochemistry, Cytotoxicity

Abstract: A phytochemical investigation of the EtOH extract of the flowers of Lagerstroemia indica L. led to the isolation and characterization of a new pyrrole alkaloid, named lagerindicine (1), along with four known compounds (2-5). Their structures were elucidated by the detailed spectroscopic analysis and comparison with literature data, whereas the structure, in particularly, the absolute configuration (AC) of 1, was firmly determined by total synthesis. All the isolates were evaluated for their cytotoxic effects against human colon cancer cell (HCT-116), and compound 3 exhibited weak cytotoxicity with IC₅₀ value of 28.4 μM.

Key words: Lagerstroemia indica Linnaeus, Pyrrole alkaloid, Total synthesis, Stereochemistry, Cytotoxicity

Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus[J]. 应用天然产物, 2021, 11(1): 73-79.

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Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus

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