Journal
MOLECULES
Volume 24, Issue 17, Pages -Publisher
MDPI
DOI: 10.3390/molecules24173140
Keywords
Isatis indigotica; alkaloid enantiomers; structure deduction; anti-inflammatory activity
Funding
- National Natural Science Foundation of China [81573571, 81673570]
- Excellent Academic Leaders Program of Shanghai [16XD1403500]
- programs of the High Level University Innovation Team
- Shanghai E-Research Institute of Bioactive Constituents in Traditional Chinese Medicine
- Shanghai Scientific and Technological Innovation Program [18401931100]
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Five pairs of alkaloid enantiomers (1a/1b-5a/5b) were obtained from Isatis indigotica (I. indigotica) roots. Amongthem, 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 K alpha 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 mu M and 65.88 mu M, respectively.
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