Sulfur-enriched alkaloids from the root of .
10.1016/j.apsb.2018.08.005
- Author:
Qinglan GUO
1
;
Chengbo XU
1
;
Minghua CHEN
1
;
Sheng LIN
1
;
Yuhuan LI
2
;
Chenggen ZHU
1
;
Jiandong JIANG
1
;
Yongchun YANG
1
;
Jiangong SHI
1
Author Information
1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
2. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China.
- Publication Type:Journal Article
- Keywords:
Antiviral activity;
Cruciferae;
Isatis indigotica;
Isatithioetherins A–E;
Isatithiopyrins A and B;
Isoepigoitrin;
Isogoitrin;
Sulfur-containing alkaloids
- From:
Acta Pharmaceutica Sinica B
2018;8(6):933-943
- CountryChina
- Language:English
-
Abstract:
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).
