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

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 s...

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Autores principales: 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
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10385092/
https://www.ncbi.nlm.nih.gov/pubmed/37513256
http://dx.doi.org/10.3390/molecules28145382
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author 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
author_facet 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
author_sort Xue, Bian-Xia
collection PubMed
description 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.
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spelling pubmed-103850922023-07-30 Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids 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 Molecules Article 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. MDPI 2023-07-13 /pmc/articles/PMC10385092/ /pubmed/37513256 http://dx.doi.org/10.3390/molecules28145382 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
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
Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids
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 Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10385092/
https://www.ncbi.nlm.nih.gov/pubmed/37513256
http://dx.doi.org/10.3390/molecules28145382
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