Sulfur-enriched alkaloids from the root of Isatis indigotica

• Published in: Acta pharmaceutica Sinica. B Vol. 8; no. 6; pp. 933 - 943
• Main Authors: Guo, Qinglan, Xu, Chengbo, Chen, Minghua, Lin, Sheng, Li, Yuhuan, Zhu, Chenggen, Jiang, Jiandong, Yang, Yongchun, Shi, Jiangong
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier 01-10-2018
• Subjects: Original article; Isogoitrin; Cruciferae; Isatis indigotica; Isatithiopyrins A and B; Antiviral activity; Isoepigoitrin; Isatithioetherins A–E; Sulfur-containing alkaloids
• ISSN: 2211-3835; 2211-3843
• DOI: 10.1016/j.apsb.2018.08.005

Five new sulfur-enriched alkaloids isatithioetherins A-E (
-
), and two pairs of scalemic enantiomers (+)- and (-)-isatithiopyrin B (
and
) and isoepigoitrin and isogoitrin
and
), along with the known scalemic enantiomers epigoitrin and goitrin (
and
), were isolated and characterized from an aqueous extract of the
roots. Their structures were determined by extensive spectroscopic data analysis, including 2D NMR and theoretical calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory (TDDFT). Compounds
-
represent a novel group of sulfur-enriched alkaloids, biogenetically originating from stereoselective assemblies of epigoitrin-derived units. Isolation and structure characterization of
and
support the postulated biosynthetic pathways for the diastereomers
and
a rare thio-Diels-Alder reaction. Compounds
and
showed antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2, IC
0.60 and 1.92 μmol/L) and the herpes simplex virus 1 (HSV-1, IC
3.70 and 2.87 μmol/L), and
also inhibited Coxsackie virus B3 (IC
0.71 μmol/L).