Analysis of scopolamine and its eighteen metabolites in rat urine by liquid chromatography-tandem mass spectrometry

Chen, Huaixia; Chen, Yong; Wang, Hong; Du, Peng; Han, Fengmei; Zhang, Hua‐Shan

doi:10.1016/j.talanta.2005.04.026

Cited by 37 publications

(20 citation statements)

References 14 publications

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“…The MS/MS spectrum of scopolamine is shown in Figure 2A and the fragmentation pathway was shown in Supporting Information Figure S1. The protonated ion was at m/z 304 and four main product ions at m/z 156, 138, 121 and 103 were consistent with the reported data [20]. The most abundant ion at m/z 138 was formed by a neutral loss of tropic acid (C 9 H 10 O 3 , 166 Da) and the loss of C 9 H 8 O 2 (148 Da) led to the fragment at m/z 156.…”

Section: Fragmentation Of Tropane Alkaloidssupporting

confidence: 89%

“…HPLC–MS/MS has been applied in the identification of compounds in a variety of TCMs, such as anthocyanins in Lycium ruthenicum Murray , alkaloids in Piper longum L ., phenolic amides in Cortex Lycii , etc . Additionally, the fragmentation of atropine analogs and cinnamamide alkaloids has been studied in some earlier research . Based on these works, it is feasible and practical to identify more potential alkaloids including tropanes and cinnamamide ones from S. tangutica .…”

Section: Introductionmentioning

confidence: 99%

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Characterization of tropane and cinnamamide alkaloids from Scopolia tangutica by high‐performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

Zhou

Jin

et al. 2019

J of Separation Science

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Scopolia tangutica is a traditional Chinese medicine used for antispasmodic, anesthesia, analgesia, and sedation. Its medicinal activity is associated to alkaloid constituents, including tropane and cinnamamide types. Low content of alkaloids in plant makes them difficult to be isolated and identified. The present work developed an effective method to quickly characterize alkaloids from Scopolia tangutica by high‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry. Thirteen reference compounds were studied for their fragmentation pathways, including five tropane alkaloids and eight cinnamamide ones. Alkaloid constituent was analyzed by an optimized high‐performance liquid chromatography method and mass spectrometry analysis to achieve systematic characterization of alkaloids from Scopolia tangutica. As a result, 53 compounds were identified, including 21 tropane alkaloids (eight new ones), 18 caffeoyl ones (ten new ones) and 14 dicaffeoyl ones (seven new ones). It was important to provide rich information in phytochemical study and structure‐guided isolation of important compounds from this plant.

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Section: Fragmentation Of Tropane Alkaloidssupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Characterization of tropane and cinnamamide alkaloids from Scopolia tangutica by high‐performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

Zhou

Jin

et al. 2019

J of Separation Science

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“…Among them, two glucuronide conjugated scopolamine analogs ( 8 and 12 ) are similar to metabolites of scopolamine and anisodine, and 7 is one of the metabolites of scopolamine3150, implicating that the metabolites of muscarinic receptor antagonists may also contribute to their in vivo effects. Of note, there are a great number of other minor or trace compounds remaining as a mixture of isomers or homologues and in low quantity in S. tangutica .…”

Section: Discussionmentioning

confidence: 99%

Discovery of new muscarinic acetylcholine receptor antagonists from Scopolia tangutica

Liu

Zhang

et al. 2017

Sci Rep

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Scopolia tangutica (S. tangutica) is a traditional Chinese medicinal plant used for antispasmodics, anesthesia, analgesia and sedation. Its pharmacological activities are mostly associated with the antagonistic activity at muscarinic acetylcholine receptors (mAchRs) of several known alkaloids such as atropine and scopolamine. With our recent identification of four hydroxycinnamic acid amides from S. tangutica, we hypothesized that this plant may contain previously unidentified alkaloids that may also contribute to its in vivo effect. Herein, we used a bioassay-guided multi-dimension separation strategy to discover novel mAchR antagonists from S. tangutica. The core of this approach is to use label-free cell phenotypic assay to first identify active fractions, and then to guide purification of active ligands. Besides four tropanes and six cinnamic acid amides that have been previously isolated from S. tangutica, we recently identified two new tropanes, one new cinnamic acid amide, and nine other compounds. Six tropane compounds purified from S. tangutica for the first time were confirmed to be competitive antagonists of muscarinic receptor 3 (M3), including the two new ones 8 and 12 with IC50 values of 1.97 μM and 4.47 μM, respectively. Furthermore, the cinnamic acid amide 17 displayed 15-fold selectivity for M1 over M3 receptors. These findings will be useful in designing lead compounds for mAchRs and elucidating mechanisms of action of S. tangutica.

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“…The metabolites were products of ester hydrolysis, N-demethylation, hydroxylation of the aromatic acid moiety, sulfation, and glucuronidation. Similarly, scopolamine metabolism was monitored in rat urine [86] and later in rat faeces, urine, and blood plasma samples [87]. Eight metabolites resulting from similar metabolism as observed for atropine (N-demethylated norscopolamine, dehydrated aposcopolamine, aponorscopolamine, hydroxyscopolamine, hydroxyscopolamine N-oxide, norscopine, scopine, and tropic acid) were found together with the parent drug in the faeces or in plasma.…”

Section: Therapeutic Drug Monitoring and Pharmacokinetic Investigationsmentioning

confidence: 92%

Tropane alkaloid analysis by chromatographic and electrophoretic techniques: An update

Aehle

Dräger

2010

Journal of Chromatography B

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Analysis of scopolamine and its eighteen metabolites in rat urine by liquid chromatography-tandem mass spectrometry

Cited by 37 publications

References 14 publications

Characterization of tropane and cinnamamide alkaloids from Scopolia tangutica by high‐performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

Characterization of tropane and cinnamamide alkaloids from Scopolia tangutica by high‐performance liquid chromatography with quadrupole time‐of‐flight tandem mass spectrometry

Discovery of new muscarinic acetylcholine receptor antagonists from Scopolia tangutica

Tropane alkaloid analysis by chromatographic and electrophoretic techniques: An update

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