title: Enantiomers of an indole alkaloid containing unusual dihydrothiopyran and 1,2,4-thiadiazole rings from the root of Isatis indigotica.
abstract: A pair of enantiomers (1a and 1b) of an indole alkaloid containing dihydrothiopyran and 1,2,4-thiadiazole rings was isolated from an aqueous extract of the root of Isatis indigotica. The structures and absolute configurations of the enantiomers were determined by extensive spectroscopic analysis, especially 2D NMR, modified Mosher's method, and electronic CD (ECD). The proposed biosynthetic pathway and preliminary investigations of the biological activity of compounds 1a and 1b against influenza virus A/Hanfang/359/95 (H3N2) and HSV-1 are also discussed.
authors.affiliation: 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, People's Republic of China.
authors.forename: Minghua
authors.initials: M
authors.lastname: Chen
authors.forename: Sheng
authors.initials: S
authors.lastname: Lin
authors.forename: Li
authors.initials: L
authors.lastname: Li
authors.forename: Chenggen
authors.initials: C
authors.lastname: Zhu
authors.forename: Xiaoliang
authors.initials: X
authors.lastname: Wang
authors.forename: Yanan
authors.initials: Y
authors.lastname: Wang
authors.forename: Bingya
authors.initials: B
authors.lastname: Jiang
authors.forename: Sujuan
authors.initials: S
authors.lastname: Wang
authors.forename: Yuhuan
authors.initials: Y
authors.lastname: Li
authors.forename: Jiandong
authors.initials: J
authors.lastname: Jiang
authors.forename: Jiangong
authors.initials: J
authors.lastname: Shi
mesh_terms: D018259:Herpesvirus 1, Human / Q000187:drug effects; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D053122:Influenza A Virus, H3N2 Subtype / Q000187:drug effects*; D031219:Isatis / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D018517:Plant Roots / Q000737:chemistry; D013237:Stereoisomerism; D013830:Thiadiazoles / Q000737:chemistry*
chemical_list: D026121:Indole Alkaloids; D013830:Thiadiazoles