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- Title
Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids.
- Authors
Xue, Bian-Xia; Yang, Tian-Tian; He, Ru-Shang; Gao, Wen-Ke; Lai, Jia-Xin; Liu, Si-Xia; Duan, Cong-Yan; Wang, Shao-Xia; Yu, Hui-Juan; Yang, Wen-Zhi; Zhang, Li-Hua; Wang, Qi-Long; Wu, Hong-Hua
- Abstract
Nardosinone, a predominant bioactive product from Nardostachys jatamansi 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.
- Subjects
HIGH temperatures; PINACOL rearrangement; INTESTINES; FLUIDS; CIRCULAR dichroism
- Publication
Molecules, 2023, Vol 28, Issue 14, p5382
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28145382