Abstract
Five pairs of alkaloid enantiomers (1a/1b–5a/5b) were obtained from Isatis indigotica (I. indigotica) roots. Among them, 1a/1b, 2a/2b and 3a/3b were determined as three pairs of new alkaloid enantiomers. Their structures were elucidated by physicochemical properties and spectroscopic methods. The absolute configurations were deduced by comparison of their experimental circular dichroism (CD) and calculated electronic circular dichroism (ECD) spectra, as well as by single-crystal X-ray crystallography using anomalous scattering of Cu Kα radiation. Alkaloids 1a and 1b possess an unpresented carbon skeleton and their putative biosynthetic pathways are discussed. Moreover, all of the alkaloids were tested for their nitric oxide (NO) inhibitory effects in RAW 264.7 cells, and 4a and 4b showed inhibitory effects with IC50 values of 76.97 μM and 65.88 μM, respectively.
Highlights
As one of the most famous traditional Chinese medicines (TCMs), ban lan gen is usually used for the treatment of various kinds of diseases, such as influenza, fever, epidemic hepatitis and infections [4,5,6]
For our continuous project to explore more bioactive components from I. indigotica [8,9], five pairs of alkaloid enantiomers were isolated from the 80% alcohol exact of I. indigotica roots
This pharmacological with the use of forepidemic the treatment of prompted us to test the inhibitory effects on nitric oxide (NO)
Summary
“Ban lan gen”, widely distributed and cultivated in the North of China, is the roots of Isatis indigotica. 1a/1b, 2a/2b and 3a/3b were determined as three pairs of new enantiomers, whose structures and absolute configurations were determined by extensive spectroscopic data analysis, including 1D, 2D-NMR and HRESIMS data, optical rotation data, comparison of their experimental circular dichroism (CD). This pharmacological action, together action, with thetogether traditional use fortraditional the treatment hepatitis, effects [1,2,3,4,5,6,7,8,9,10]. Production of all the isolated alkaloids epidemic hepatitis, prompted us to test the inhibitory effects on nitric oxide (NO) production of all (1a/1b–5a/5b). Biosynthetic pathways the NO inhibitoryare activities of these enantiomers are presented
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