Cargando…
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...
Autores principales: | , , , , , , , , , , , , |
---|---|
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 |
_version_ | 1785081318153912320 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10385092 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT xuebianxia degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT yangtiantian degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT herushang degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT gaowenke degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT laijiaxin degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT liusixia degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT duancongyan degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT wangshaoxia degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT yuhuijuan degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT yangwenzhi degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT zhanglihua degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT wangqilong degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids AT wuhonghua degradationprofilingofnardosinoneathightemperatureandinsimulatedgastricandintestinalfluids |