title: Antiviral glycosidic bisindole alkaloids from the roots of Isatis indigotica.
abstract: Seven new glycosidic bisindole alkaloids, isatindigobisindolosides A-G (1-7), were isolated from an aqueous extract of the Isatis indigotica roots. Their structures including absolute configurations were determined by spectroscopic and chemical methods, together with calculations of electronic circular dichroism (ECD) spectra based on the quantum-mechanical time-dependent density functional theory. In the NMR spectra of 1-3, it is found that integration of H-2 and intensity of C-2 are affected not only by a substitution group at C-2 but also by solvents. Influences of the glucopyranosyloxy on the calculated ECD spectra of the glycosidic bisindole alkaloids are discussed. Compounds 2, 5, and 6 showed antiviral activity against both the influenza virus A/Hanfang/359/95 (H3N2) and Coxsackie virus B3 with IC50 values of 8.4-100.0 μM.
authors.affiliation: a State Key Laboratory of Bioactive Substance and Function of Natural Medicines , Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050 , China.
authors.forename: Yu-Feng
authors.initials: YF
authors.lastname: Liu
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Chen
authors.forename: Qing-Lan
authors.initials: QL
authors.lastname: Guo
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Cheng-Bo
authors.initials: CB
authors.lastname: Xu
authors.forename: Yue-Ping
authors.initials: YP
authors.lastname: Jiang
authors.forename: Yu-Huan
authors.initials: YH
authors.lastname: Li
authors.forename: Jian-Dong
authors.initials: JD
authors.lastname: Jiang
authors.forename: Jian-Gong
authors.initials: JG
authors.lastname: Shi
mesh_terms: D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects; D031219:Isatis / Q000737:chemistry*; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry
chemical_list: D000998:Antiviral Agents; D006027:Glycosides; D026121:Indole Alkaloids
keywords: Cruciferae; Influences of the glucopyranosyloxy on the calculated ECD spectra; Isatis indigotica; antiviral activity; bisindole alkaloid glucoside; isatindigobisindolosides A–G