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. 2019 Aug 29;24(17):3140.
doi: 10.3390/molecules24173140.

Alkaloid Enantiomers from the Roots of Isatis indigotica

Dongdong Zhang  1 , Yanhong Shi  2 , Rui Xu  1 , Kang Du  1 , Fujiang Guo  1 , Kaixian Chen  1   3 , Yiming Li  4 , Rui Wang  5
Affiliations

Alkaloid Enantiomers from the Roots of Isatis indigotica

Dongdong Zhang et al. Molecules. .

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.

Keywords: Isatis indigotica; alkaloid enantiomers; anti-inflammatory activity; structure deduction.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Structures of compounds 1a/1b–5a/5b.
Figure 2
Figure 2
Key 1H-1H COSY and HMBC correlations of compounds 1a/1b–3a/3b.
Figure 3
Figure 3
Experimental and calculated electronic circular dichroism (ECD) spectra of compounds 1a/1b–3a/3b.
Figure 4
Figure 4
Putative biosynthetic pathway of compound 1.
Figure 5
Figure 5
ORTEP darning of (+)-(2′S)-isatisindigoticanine C (2b).
See this image and copyright information in PMC

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