Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity
Protosappanoside D (PTD) is a new component isolated from the extract of <i>Caesalpinia decapetala</i> for the first time. Its structure was identified as protosappanin B-3-<i>O</i>-<i>β</i>-D-glucoside by <sup>1</sup>H-NMR, <sup>13</sup>C-...
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MDPI AG
2022-09-01
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| author | Yueting Li Wensha Meng Li Yuan Li Jiang Zuying Zhou Mingyan Chi Zipeng Gong Xue Ma Yong Huang Lin Zheng |
| author_facet | Yueting Li Wensha Meng Li Yuan Li Jiang Zuying Zhou Mingyan Chi Zipeng Gong Xue Ma Yong Huang Lin Zheng |
| author_sort | Yueting Li |
| collection | DOAJ |
| description | Protosappanoside D (PTD) is a new component isolated from the extract of <i>Caesalpinia decapetala</i> for the first time. Its structure was identified as protosappanin B-3-<i>O</i>-<i>β</i>-D-glucoside by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 2D-NMR and MS techniques. To date, the pharmacological activities, metabolism or pharmacokinetics of PTD has not been reported. Therefore, this research to study the anti-inflammatory activity of PTD was investigated via the LPS-induced RAW264.7 cells model. At the same time, we also used the UHPLC/Q Exactive Plus MS and UPLC-MS/MS methods to study the metabolites and pharmacokinetics of PTD, to calculate its bioavailability for the first time. The results showed that PTD could downregulate secretion of the pro-inflammatory cytokines. In the metabolic study, four metabolites were identified, and the primary degradative pathways in vivo involved the desaturation, oxidation, methylation, alkylation, dehydration, degradation and desugarization. In the pharmacokinetic study, PTD and its main metabolite protosappanin B (PTB) were measured after oral and intravenous administration. After oral administration of PTD, its T<sub>max</sub> was 0.49 h, t<sub>1/2z</sub> and MRT<sub>(0–t)</sub> were 3.47 ± 0.78 h and 3.06 ± 0.63 h, respectively. It shows that PTD was quickly absorbed into plasma and it may be eliminated quickly in the body, and its bioavailability is about 0.65%. |
| first_indexed | 2024-03-09T22:59:56Z |
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| language | English |
| last_indexed | 2024-03-09T22:59:56Z |
| publishDate | 2022-09-01 |
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| series | Molecules |
| spelling | doaj.art-4f9ca8478dcc45559aa8968b316be0a32023-11-23T18:04:05ZengMDPI AGMolecules1420-30492022-09-012718609010.3390/molecules27186090Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological ActivityYueting Li0Wensha Meng1Li Yuan2Li Jiang3Zuying Zhou4Mingyan Chi5Zipeng Gong6Xue Ma7Yong Huang8Lin Zheng9State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaEngineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaEngineering Research Center for the Development and Application of Ethnic Medicine and TCM (Ministry of Education), Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang 550004, ChinaProtosappanoside D (PTD) is a new component isolated from the extract of <i>Caesalpinia decapetala</i> for the first time. Its structure was identified as protosappanin B-3-<i>O</i>-<i>β</i>-D-glucoside by <sup>1</sup>H-NMR, <sup>13</sup>C-NMR, 2D-NMR and MS techniques. To date, the pharmacological activities, metabolism or pharmacokinetics of PTD has not been reported. Therefore, this research to study the anti-inflammatory activity of PTD was investigated via the LPS-induced RAW264.7 cells model. At the same time, we also used the UHPLC/Q Exactive Plus MS and UPLC-MS/MS methods to study the metabolites and pharmacokinetics of PTD, to calculate its bioavailability for the first time. The results showed that PTD could downregulate secretion of the pro-inflammatory cytokines. In the metabolic study, four metabolites were identified, and the primary degradative pathways in vivo involved the desaturation, oxidation, methylation, alkylation, dehydration, degradation and desugarization. In the pharmacokinetic study, PTD and its main metabolite protosappanin B (PTB) were measured after oral and intravenous administration. After oral administration of PTD, its T<sub>max</sub> was 0.49 h, t<sub>1/2z</sub> and MRT<sub>(0–t)</sub> were 3.47 ± 0.78 h and 3.06 ± 0.63 h, respectively. It shows that PTD was quickly absorbed into plasma and it may be eliminated quickly in the body, and its bioavailability is about 0.65%.https://www.mdpi.com/1420-3049/27/18/6090Protosappanoside Dstructure elucidationmetabolitespharmacokineticsanti-inflammation |
| spellingShingle | Yueting Li Wensha Meng Li Yuan Li Jiang Zuying Zhou Mingyan Chi Zipeng Gong Xue Ma Yong Huang Lin Zheng Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity Molecules Protosappanoside D structure elucidation metabolites pharmacokinetics anti-inflammation |
| title | Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity |
| title_full | Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity |
| title_fullStr | Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity |
| title_full_unstemmed | Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity |
| title_short | Identification of Protosappanoside D from <i>Caesalpinia decapetala</i> and Evaluation of Its Pharmacokinetic, Metabolism and Pharmacological Activity |
| title_sort | identification of protosappanoside d from i caesalpinia decapetala i and evaluation of its pharmacokinetic metabolism and pharmacological activity |
| topic | Protosappanoside D structure elucidation metabolites pharmacokinetics anti-inflammation |
| url | https://www.mdpi.com/1420-3049/27/18/6090 |
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