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Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids

Authors :
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
Source :
Molecules, Vol 28, Iss 14, p 5382 (2023)
Publication Year :
2023
Publisher :
MDPI AG, 2023.

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.

Details

Language :
English
ISSN :
14203049
Volume :
28
Issue :
14
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.17ba3d51d891426a9402416c67c6c2eb
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules28145382