Citation: Li Da-Wei, Guo Qing-Lan, Meng Xian-Hua, Zhu Cheng-Gen, Xu Cheng-Bo, Shi Jian-Gong. Two pairs of unusual scalemic enantiomers from Isatis indigotica leaves[J]. Chinese Chemical Letters, ;2016, 27(12): 1745-1750. doi: 10.1016/j.cclet.2016.08.006 shu

Two pairs of unusual scalemic enantiomers from Isatis indigotica leaves

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China

Corresponding author: Shi Jian-Gong, shijg@imm.ac.cn
Received Date: 29 June 2016
Revised Date: 23 July 2016
Accepted Date: 16 August 2016
Available Online: 3 December 2016

Figures(4)

Two pairs of unusual scalemic enantiomers with a novel carbon skeleton of 2-[1'-(4"-hydroxy-3",5"-dimethoxyphenyl)ethyl]-2-methoxyindolin-3-one, named isatidifoliumindolinones A-D (1-4), were isolated from an aqueous extract of Isatis indigotica leaves (da qing ye). Their structures including absolute configurations were determined by spectroscopic data analysis combined with comparison of their experimental CD and calculated ECD spectra. Validity of the ECD spectra calculation to assign the absolute configurations is discussed. Plausible biosynthetic pathways of 1-4 are proposed. Stereochemistry-dependent activity against LPS-induced NO production in BV2 cells was observed, and among the stereoisomers compound 4 is most active.
- Isatis indigotica,
- Cruciferae,
- 2-[1'-(4"-Hydroxy-3",5"-dimethoxyphenyl)ethyl]-2-methoxyindolin-3-one,
- Scalemic enantiomer,
- Isatidifoliumindolinones A-D,
- Bioactivity
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