Degradation Profiling of Nardosinone at High Temperature and in Simulated Gastric and Intestinal Fluids
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Published:2023-07-13
Issue:14
Volume:28
Page:5382
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ISSN:1420-3049
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Container-title:Molecules
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language:en
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Short-container-title:Molecules
Author:
Xue Bian-Xia1, Yang Tian-Tian1, He Ru-Shang1, Gao Wen-Ke1, Lai Jia-Xin1, Liu Si-Xia1, Duan Cong-Yan1, Wang Shao-Xia1, Yu Hui-Juan1, Yang Wen-Zhi1, Zhang Li-Hua1, Wang Qi-Long1ORCID, Wu Hong-Hua12ORCID
Affiliation:
1. National 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, China 2. Tianjin Key Laboratory of Therapeutic Substance of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, 10 Poyanghu Road, West Area, Tuanbo New Town, Jinghai District, Tianjin 301617, China
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.
Funder
Tianjin Committee of Science and Technology of China National Key Research and Development Program of China Important Drug Development Fund, Ministry of Science and Technology of China
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference33 articles.
1. Nardostachys chinensis Batalin: A review of traditional uses, phytochemistry, and pharmacology;Rehman;Phytother. Res.,2019 2. A review on traditional uses, phytochemistry, pharmacology, toxicology and the analytical methods of the genus Nardostachys;Wang;J. Ethnopharmacol.,2021 3. Determination of the content of nardosinone in Nardostachys chinensis Batal;Liu;Chin. J. Tradit. Chin. Med. Pharm.,2015 4. A simple and rapid UPLC-PDA method for quality control of Nardostachys jatamansi;Zhang;Planta Med.,2018 5. Simultaneous determination of chlorogenic acid and nardosinone in Nardostachys chinensis DC. from different producing areas by HPLC;Li;J. Inf. Tradit. Chin. Med.,2015
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