title: IR and Vibrational Circular Dichroism Spectroscopy of Matrine- and Artemisinin-Type Herbal Products: Stereochemical Characterization and Solvent Effects.
abstract: Five Chinese herbal medicines--matrine, oxymatrine, sophoridine, artemisinin, and dihydroartemisinin--were investigated using vibrational circular dichroism (VCD) experiments and density functional theory calculations to extract their stereochemical information. The three matrine-type alkaloids are available from the dry roots of Sophora flavescens and have long been used in various traditional Chinese herbal medicines to combat diseases such as cancer and cardiac arrhythmia. Artemisinin and the related dihydroartemisinin, discovered in 1979 by Professor Youyou Tu, a 2015 Nobel laureate in medicine, are effective drugs for the treatment of malaria. The VCD measurements were carried out in CDCl3 and DMSO-d6, two solvents with different dielectric constants and hydrogen-bonding characteristics. A "clusters-in-a-liquid" approach was used to model both explicit and implicit solvent effects. The studies show that effectively accounting for solvent effects is critical to using IR and VCD spectroscopy to provide unique spectroscopic features to differentiate the potential stereoisomers of these Chinese herbal medicines.
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Yuefei
authors.initials: Y
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: M Reza
authors.initials: MR
authors.lastname: Poopari
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Xiaoli
authors.initials: X
authors.lastname: Cai
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Aliaksandr
authors.initials: A
authors.lastname: Savin
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Zahra
authors.initials: Z
authors.lastname: Dezhahang
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Joseph
authors.initials: J
authors.lastname: Cheramy
authors.affiliation: Department of Chemistry, University of Alberta , Edmonton, Alberta, Canada , T6G 2G2.
authors.forename: Yunjie
authors.initials: Y
authors.lastname: Xu
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D037621:Artemisinins / Q000737:chemistry*; D002942:Circular Dichroism; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification*; D006860:Hydrogen Bonding; D008288:Malaria / Q000188:drug therapy; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D029909:Sophora / Q000737:chemistry*; D000093842:Matrines
chemical_list: D000470:Alkaloids; D037621:Artemisinins; D004365:Drugs, Chinese Herbal; D011807:Quinolizines; C039060:artenimol; C037573:oxymatrine; C031327:artemisinin; D000093842:Matrines