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Developmental Changes in the Composition of Five Anthraquinones from Rheum palmatum as Quantified by 1H-NMR

Authors

  • Zhi-Wei Wang,

    1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China
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  • Jun-Song Wang,

    1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China
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  • Ming-Hua Yang,

    1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China
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  • Jian-Guang Luo,

    1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China
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  • Ling-Yi Kong

    Corresponding author
    • State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing, People's Republic of China
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Correspondence to: L.-Y. Kong, State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People's Republic of China. Email: cpu_lykong@126.com

ABSTRACT

Introduction

Rheum palmatum is an important traditional Chinese medicine featuring anthraquinones with several activities. Generally, rhein, emodin, aloe-emodin, physcion and chrysophanol are used as chemical markers for the quality control of rhubarb products.

Objective

To develop a simple protocol for the quantification of rhein, emodin, aloe-emodin, physcion and chrysophanol in R. palmatum collected at different developmental stages.

Methods

1H-NMR spectra were measured on samples dissolved in acetone-d6, quantification was carried out using the signals of H-4 of rhein (δH 8.36), H-7 of emodin (δH 6.68), CH2OH of aloe-emodin (δH 4.81), OCH3 of physcion (δH 4.02) and CH3 of chrysophanol (δH 2.50), which were well separated from other signals. Quantitative analysis was based on the relative ratio of the intensity of each compound to the known amount of internal standard maleic acid.

Results

The quantitative 1H-NMR (qHNMR) method developed showed good precision, trueness, linearity, repeatability and stability for the quantification of rhein, emodin, aloe-emodin, physcion and chrysophanol. This method was applied successfully to explore the seasonal variations of the five major anthraquinones in R. palmatum, and provided quantitative results in reasonable agreement with those obtained by the HPLC–UV method.

Conclusion

Compared with the conventional HPLC-based methods, the qHNMR analysis is rapid, reference-free and convenient with less sample pre-treatment. This technique should be a feasible choice for the quality control of R. palmatum. Copyright © 2013 John Wiley & Sons, Ltd.

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