Abstract
As chemical drugs, separation and quantification of the specific enantiomer from the chiral compounds in herbal medicines are becoming more important. To clarify the chemical characterization of chiral glucosinolates—the antiviral active ingredients of Radix Isatidis, an optimized efficient method of HPLC-UV-CD was developed to simultaneously separate and quantify the four main chiral glucosinolates: progoitrin, epiprogoitrin, and R,S-goitrin. The first step was to determine progoitrin, epiprogoitrin, and R,S-goitrin using HPLC-UV, and then determine the R-goitrin and S-goitrin by coupling with CD detection. Subsequently, through the linear relations between anisotropy factor (g factor) and the percent optical purity of R-goitrin, the contents of R-goitrin and S-goitrin from the R,S-goitrin mixture were calculated separately. Furthermore, the chemical composition features of the four chiral glucosinolates in 37 samples from crude drugs, decoction pieces, and granules of R. Isatidis were conducted. The total content of the four glucosinolates was obviously higher in crude drugs, and the variance character of each glucosinolate contents was different. In summary, the accurate measurement method reported here allows for better control of the internal quality of R. Isatidis and its granules and provides a powerful approach for the analysis of other chiral components in traditional Chinese medicines.
Highlights
Natural products from traditional Chinese medicines (TCMs) represent a major part of today’s pharmaceutical market as they possess a number of biological activities, such as antimicrobial, antitumor, anti-inflammatory, antiviral, cardiovascular activities, and so on [1]
Comparison with different compositions of acetonitrile/methanol–water, methanol–water with different modifiers including formic acid and ammonium acetate showed the combination of methanol and 30 mM ammonium acetate gave an optimal mobile phase system for glucosinolates separation
The recoveries of five glucosinolates were measured from 99.1 to 103.3%, and the RSD values were less than 3.0% (Table 3)
Summary
Natural products from traditional Chinese medicines (TCMs) represent a major part of today’s pharmaceutical market as they possess a number of biological activities, such as antimicrobial, antitumor, anti-inflammatory, antiviral, cardiovascular activities, and so on [1]. S-ibuprofen, the first chiral drugs of the non-steroidal anti-inflammatory drug approved in 1994, was over a 100-fold more potent as an inhibitor of cyclooxygenase 1 enzyme than R-ibuprofen [3]. 45 new drugs approved by the US food and Drug Administration in 2015 were single enantiomers, except for lesinurad [4]. For this reason, investigating the biological activities of specific enantiomers of chiral compounds in TCMs is becoming more important. Chiral analysis of the chemical constituents in TCMs is urgent and desired
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