Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids
Nardosinone, a predominant bioactive product from <i>Nardostachys jatamansi</i> DC, is well-known for its promising therapeutic applications, such as being used as a drug on anti-inflammatory, antidepressant, cardioprotective, anti-neuroinflammatory, anti-arrhythmic, anti-periodontitis,...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-07-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/14/5382 |
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| author | Bian-Xia Xue Tian-Tian Yang Ru-Shang He Wen-Ke Gao Jia-Xin Lai Si-Xia Liu Cong-Yan Duan Shao-Xia Wang Hui-Juan Yu Wen-Zhi Yang Li-Hua Zhang Qi-Long Wang Hong-Hua Wu |
| author_facet | Bian-Xia Xue Tian-Tian Yang Ru-Shang He Wen-Ke Gao Jia-Xin Lai Si-Xia Liu Cong-Yan Duan Shao-Xia Wang Hui-Juan Yu Wen-Zhi Yang Li-Hua Zhang Qi-Long Wang Hong-Hua Wu |
| author_sort | Bian-Xia Xue |
| collection | DOAJ |
| description | Nardosinone, a predominant bioactive product from <i>Nardostachys jatamansi</i> DC, is well-known for its promising therapeutic applications, such as being used as a drug on anti-inflammatory, antidepressant, cardioprotective, anti-neuroinflammatory, anti-arrhythmic, anti-periodontitis, etc. However, its stability under varying environmental conditions and its degradation products remain unclear. In this study, four main degradation products, including two previously undescribed compounds [2–deoxokanshone M (64.23%) and 2–deoxokanshone L (1.10%)] and two known compounds [desoxo-narchinol A (2.17%) and isonardosinone (3.44%)], were firstly afforded from the refluxed products of nardosinone in boiling water; their structures were identified using an analysis of the extensive NMR and X–ray diffraction data and the simulation and comparison of electronic circular dichroism spectra. Compared with nardosinone, 2–deoxokanshone M exhibited potent vasodilatory activity without any of the significant anti-neuroinflammatory activity that nardosinone contains. Secondly, UPLC–PDA and UHPLC–DAD/Q–TOF MS analyses on the degradation patterns of nardosinone revealed that nardosinone degraded more easily under high temperatures and in simulated gastric fluid compared with the simulated intestinal fluid. A plausible degradation pathway of nardosinone was finally proposed using nardosinonediol as the initial intermediate and involved multiple chemical reactions, including peroxy ring-opening, keto–enol tautomerization, oxidation, isopropyl cleavage, and pinacol rearrangement. Our findings may supply certain guidance and scientific evidence for the quality control and reasonable application of nardosinone-related products. |
| first_indexed | 2024-03-11T00:46:37Z |
| format | Article |
| id | doaj.art-17ba3d51d891426a9402416c67c6c2eb |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T00:46:37Z |
| publishDate | 2023-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-17ba3d51d891426a9402416c67c6c2eb2023-11-18T20:41:19ZengMDPI AGMolecules1420-30492023-07-012814538210.3390/molecules28145382Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal FluidsBian-Xia Xue0Tian-Tian Yang1Ru-Shang He2Wen-Ke Gao3Jia-Xin Lai4Si-Xia Liu5Cong-Yan Duan6Shao-Xia Wang7Hui-Juan Yu8Wen-Zhi Yang9Li-Hua Zhang10Qi-Long Wang11Hong-Hua Wu12National Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNational Key Laboratory of Chinese Medicine Modernization, State Key Laboratory of Component-Based Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, ChinaNardosinone, a predominant bioactive product from <i>Nardostachys jatamansi</i> DC, is well-known for its promising therapeutic applications, such as being used as a drug on anti-inflammatory, antidepressant, cardioprotective, anti-neuroinflammatory, anti-arrhythmic, anti-periodontitis, etc. However, its stability under varying environmental conditions and its degradation products remain unclear. In this study, four main degradation products, including two previously undescribed compounds [2–deoxokanshone M (64.23%) and 2–deoxokanshone L (1.10%)] and two known compounds [desoxo-narchinol A (2.17%) and isonardosinone (3.44%)], were firstly afforded from the refluxed products of nardosinone in boiling water; their structures were identified using an analysis of the extensive NMR and X–ray diffraction data and the simulation and comparison of electronic circular dichroism spectra. Compared with nardosinone, 2–deoxokanshone M exhibited potent vasodilatory activity without any of the significant anti-neuroinflammatory activity that nardosinone contains. Secondly, UPLC–PDA and UHPLC–DAD/Q–TOF MS analyses on the degradation patterns of nardosinone revealed that nardosinone degraded more easily under high temperatures and in simulated gastric fluid compared with the simulated intestinal fluid. A plausible degradation pathway of nardosinone was finally proposed using nardosinonediol as the initial intermediate and involved multiple chemical reactions, including peroxy ring-opening, keto–enol tautomerization, oxidation, isopropyl cleavage, and pinacol rearrangement. Our findings may supply certain guidance and scientific evidence for the quality control and reasonable application of nardosinone-related products.https://www.mdpi.com/1420-3049/28/14/5382nardosinone<i>Nardostachys jatamansi</i> DC.simulated gastric fluidsimulated intestinal fluiddegradation2–deoxokanshone M |
| spellingShingle | Bian-Xia Xue Tian-Tian Yang Ru-Shang He Wen-Ke Gao Jia-Xin Lai Si-Xia Liu Cong-Yan Duan Shao-Xia Wang Hui-Juan Yu Wen-Zhi Yang Li-Hua Zhang Qi-Long Wang Hong-Hua Wu Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids Molecules nardosinone <i>Nardostachys jatamansi</i> DC. simulated gastric fluid simulated intestinal fluid degradation 2–deoxokanshone M |
| title | Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids |
| title_full | Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids |
| title_fullStr | Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids |
| title_full_unstemmed | Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids |
| title_short | Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids |
| title_sort | degradation profiling of nardosinone at high temperature and in simulated gastric and intestinal fluids |
| topic | nardosinone <i>Nardostachys jatamansi</i> DC. simulated gastric fluid simulated intestinal fluid degradation 2–deoxokanshone M |
| url | https://www.mdpi.com/1420-3049/28/14/5382 |
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