Three pairs of alkaloid enantiomers from the root of Isatis indigotica.
10.1016/j.apsb.2016.01.003
- Author:
Yufeng LIU
1
;
Xiaoliang WANG
2
;
Minghua CHEN
3
;
Sheng LIN
2
;
Li LI
2
;
Jiangong SHI
2
Author Information
1. 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; Department of Pharmacy, Jining Medical University, Jining 272067, China.
2. 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.
3. 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
- Publication Type:Journal Article
- Keywords:
2-Oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid;
3-Thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one;
Alkaloid enantiomer;
Chiral separation;
Cruciferae;
Indolo[2,1-b]quinazolinone;
Isatis indigotica
- From:
Acta Pharmaceutica Sinica B
2016;6(2):141-147
- CountryChina
- Language:English
-
Abstract:
Three pairs of enantiomerically pure alkaloids with diverse structure features, named isatindigoticoic acid A and epiisatindigoticoic acid A [(-)-1 and (+)-1], phaitanthrin A and epiphaitanthrin A [(-)-2 and (+)-2], and isatindopyrromizol A and epiisatindopyrromizol A [(-)-3 and (+)-3], respectively, were isolated from an aqueous extract of the roots of Isatis indigotica. Racemic and scalemic mixtures of these enantiomers were separated by HPLC on a chiral semi-preparative column. Their structures including absolute configurations were determined by extensive spectroscopic analysis in conjunction with the calculation of electronic circular dichroism (ECD) spectra. The enantiomer pairs possess parent structures of 2-oxo-1,2,3,4-tetrahydroquinoline-4-carboxylic acid, indolo[2,1-b]quinazolinone, and 3-thioxohexahydro-1H-pyrrolo[1,2-c]imidazol-1-one, respectively. Except for phaitanthrin A [(-)-2] which the configuration was previously undetermined, these compounds are new enantiomeric natural products.
