Abstract
Dehydrocorydaline (DHC), a quaternary alkaloid from Corydalis yanhusuo, has been demonstrated to be the active constituent in the treatment of coronary heart disease. In this study, a high-performance liquid chromatography–electrospray ionization–triple quadrupole linear ion trap mass spectrometry (HPLC–ESI–QTRAP MS) technique was used to identify DHC metabolites in plasma and bile after oral administration of DHC to rats. A total of 18 metabolites (M1 to M18) were identified and characterized by LC–MS/MS in the positive ion mode. These 18 metabolites were all present in rat bile, while only 9 were detected in plasma. O-demethylation, hydroxylation, di-hydroxylation, glucuronidation of O-demethyl DHC, sulfation of O-demethyl DHC and di-hydroxylation of dehydro-DHC were the major metabolic pathways of DHC. This is the first time that these metabolites of DHC have been identified in rat plasma and bile, which provides useful information for further analysis of the biotransformation of DHC and other quaternary protoberberine-type alkaloids.
Highlights
Through the previously established fingerprint-efficacy relationship between chemical fingerprints of quaternary ammonium alkaloids from C. yanhusuo and its cardioprotection efficiency, we found that DHC is one of the main effective components of this traditional Chinese medicine (TCM) and can be adopted as a reference component for quality control of C. yanhusuo [6]
The observed metabolites were generated by O-demethylation, OO-demethylation, O-demethylation followed by glucuronidation, O-demethylation followed by demethylation followed by glucuronidation, O-demethylation followed by sulfation, disulfation, di-hydroxylation and dehydrogenation, di-hydroxylation and hydroxylation
A total of 18 metabolites were identified using the MRM–IDA–EPI mode, and their structures were elucidated on the basis of the retention times of reference standards and characteristic fragment ions
Summary
Through the previously established fingerprint-efficacy relationship between chemical fingerprints of quaternary ammonium alkaloids from C. yanhusuo and its cardioprotection efficiency, we found that DHC is one of the main effective components of this TCM and can be adopted as a reference component for quality control of C. yanhusuo [6]. The in vivo metabolism of C. yanhusuo extract in rat plasma was analyzed by high-performance liquid chromatography coupled to mass spectrometry (HPLC–MS), which revealed that 10 bioactive components of C. yanhusuo were present in the blood [9]. To further evaluate the in vivo metabolism of DHC and to obtain more information for pharmacological research, a high-performance liquid chromatography–electrospray ionization–triple quadrupole linear ion trap mass spectrometry (HPLC-ESI-QTRAP MS) method was developed to analyze the metabolites of DHC in rat plasma and bile. A total of 18 metabolites were identified using the multiple reaction monitoring–information-dependent acquisition–triggering enhanced product ion (MRM-IDA-EPI) mode
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