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      Characterization and quantitation of aristolochic acid analogs in different parts of Aristolochiae Fructus, using UHPLC-Q/TOF-MS and UHPLC-QqQ-MS

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          Abstract

          Aristolochiae Fructus, a Chinese herbal medicine derived from the fruit of Aristolochia contorta Bge., contains nephrotoxic aristolochic acid analogues (AAAs). According to ancient medical texts, various medicinal parts of the fruit of A. contorta were ever used. In order to reveal which part could be safely and effectively used, it is necessary to analyze the chemical profiles of different medicinal parts. Herein we compared the chemical compositions and determined aristolochic acid I (AA-I) and aristolochic acid II (AA-II) in the four parts viz. outer pericarp, inner pericarp, septum, and seed. Ultra-high performance liquid chromatography equipped with quadrupole time-of-flight mass spectrometry (UHPLC-QTOF-MS) was applied for chemical profiling. Ultra-high performance liquid coupled with triple quadrupole mass spectrometry (UHPLC-QqQ-MS) was employed to quantify AA-I and AA-II in different parts. It was found that the chemical compositions of the four parts varied both qualitatively and quantitatively. A total of 10 AAAs, including 5 aristolochic acids and 5 aristolactams, together with 3 alkaloids, were unambiguously or tentatively identified by UHPLC-QTOF-MS. The quantitatively analytical results obtained by UHPLC-QqQ-MS showed that AA-I and AA-II exclusively accumulate in the seeds of A. contorta. These findings provide supporting data for the rational selection of medicinal parts.

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          Most cited references 13

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          Aristolochic acid nephropathy: a worldwide problem.

          Aristolochic acid nephropathy (AAN), a progressive renal interstitial fibrosis frequently associated with urothelial malignancies, was initially reported in a Belgian cohort of more than 100 patients after the intake of slimming pills containing a Chinese herb, Aristolochia fangchi. Although botanicals known or suspected to contain aristolochic acid (AA) were no longer permitted in many countries, several AAN cases were regularly observed all around the world. The incidence of AAN is probably much higher than initially thought, especially in Asia and the Balkans. In Asian countries, where traditional medicines are very popular, the complexity of the pharmacopoeia represents a high risk for AAN because of the frequent substitution of the botanical products by AA-containing herbs. In the Balkan regions, the exposure to AA found in flour obtained from wheat contaminated with seeds of Aristolochia clematitis could be responsible for the so-called Balkan-endemic nephropathy. Finally, despite the Food and Drug Administration's warnings concerning the safety of botanical remedies containing AA, these herbs are still sold via the Internet.
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            Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities.

            Aristolactams, having a phenanthrene chromophore are a small group of compounds mainly found in the Aristolochiaceae together with the aristolochic acids and 4,5-dioxoaporphines. In this report, these three important classes of natural products are reviewed and classified on the basis of their oxygenation pattern. In addition the biological activities of these compounds and their general chemistry are discussed.
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              Naturally occurring aristolochic acid analogues and their toxicities.

              Covering: 1960 to 2013. Aristolochic acids are known for causing aristolochic acid nephropathy, a renal fibrosis often associated with urothelial carcinoma. Aristolochic acid I and II are considered to be the cause of these nephrotoxic and carcinogenic effects. However a variety of aristolochic acid analogues, including aristolactams and 4,5-dioxoaporphines have been reported. Their implications in aristolochic acid nephropathy have possibly been overlooked. In this report, in vivo and in vitro toxicity and mutagenicity of these three classes of compounds are discussed. Furthermore, the review gives an update of aristolochic acids, aristolactams and 4,5-dioxoaporphines reported between 2003 and 2013 and their biological activities.
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                Author and article information

                Journal
                CJNM
                Chinese Journal of Natural Medicines
                Elsevier
                1875-5364
                20 May 2017
                : 15
                : 5
                : 392-400
                Affiliations
                1State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China
                2School of Chinese Medicine, Hong Kong Baptist University, Kowloon, Hong Kong, China
                Author notes
                *Corresponding author: LI Hui-Jun, Tel/Fax: 86-25-83271379, E-mail: cpuli@ 123456163.com ; ZHAO Zhong-Zhen, Tel: 852-34112424, Fax: 852-34112461, E-mail: zzzhao@ 123456hkbu.edu.hk

                These authors have no conflict of interest to declare.

                Article
                S1875-5364(17)30060-2
                10.1016/S1875-5364(17)30060-2
                Copyright © 2017 China Pharmaceutical University. Published by Elsevier B.V. All rights reserved.
                Funding
                Funded by: National Natural Science Foundation of China
                Award ID: 81322051
                Funded by: Central Universities
                Award ID: G140026
                This work was financially supported by the National Natural Science Foundation of China (No. 81322051), the Project Funded by the Priority Academic Program Development (PAPD) of Jiangsu Higher Education Institutions and the Fundamental Research Funds for the Central Universities (No. G140026).

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