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New acylated flavonol glycosides with antibacterial activity from root barks of Sophora japonica

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Abstract

The root barks of Sophora japonica L., a plant widely used in traditional Chinese medicine, were extracted with 70 % Me2CO. The antibacterial activity of the crude extracts and fractions from the subsequent purification was evaluated against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Klebsiella pneumonia and Escherichia coli). Further purification of the EtOAc fraction, which exhibited the strongest bacterial inhibitory activity among the resultant fractions, led to the isolation of three new acylated flavonol glycosides, quercetin 3-O-(4″-(E)-caffeoyl)-α-rhamnopyranoside (1), quercetin 3-O-(4″-(Z)-caffeoyl)-α-rhamnopyranoside (2) and kaempferol 3-O-(4″-galloyl)-α-rhamnopyranoside (3), as well as a known flavonol glycoside, kaempferol 3-O-α-arabinofuranoside (4). Structures of the isolated compounds were elucidated by spectroscopic techniques such as 1D and 2D NMR, and other chemical methods. Acylated flavonol glycosides 1–3 are new natural compounds, and their structures were elucidated here for the first time. Antibacterial study indicated that compounds 1–3 showed bacteria inhibitory effects, especially against S. aureus. Compound 3 was the most potent one, with MIC values of 25, 0.78, 6.25 and 50 μg/mL against B. subtilis, S. aureus, K. pneumonia and E. coli, respectively, while compound 4 did not exhibit antibacterial capability.

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Acknowledgments

This project was financially supported by the State Key Laboratory of Tree Genetics and Breeding (Northeast Forestry University) (K2013101), Natural Science Foundation of Tianjin City (13JCZDJC29400, 13JCZDJC33700), State Key Laboratory of Pulp & Paper Engineering (201503, 201359), Innovation Foundation for Young Teachers in Tianjin University of Science & Technology (2014CXLG14) and Foundation (201405) of Tianjin Key Laboratory of Marine Resources & Chemistry (Tianjin University of Science & Technology), P.R. China.

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Authors and Affiliations

  1. Tianjin Key Laboratory of Pulp and Paper, College of Paper Making Science and Technology, Tianjin University of Science and Technology, Tianjin, 300457, People’s Republic of China

    Chuan-Ling Si, Liang-Liang An, Dan-Ni Xie, Cui-Yun Liu, Xiao-Qian Chen, Guan-Hua Wang, Dan Huo, Qiu-Lin Yang & Yi-Mei Hong

  2. State Key Laboratory of Tree Genetics and Breeding, Northeast Forestry University, Harbin, 150040, People’s Republic of China

    Chuan-Ling Si

  3. Tianjin Key Laboratory of Marine Resources and Chemistry, Tianjin University of Science and Technology, Tianjin, 300457, People’s Republic of China

    Guan-Hua Wang

  4. State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, 510640, People’s Republic of China

    Chuan-Ling Si, Guan-Hua Wang & Qiu-Lin Yang

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  1. Chuan-Ling Si
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  2. Liang-Liang An
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Correspondence to Chuan-Ling Si.

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Si, CL., An, LL., Xie, DN. et al. New acylated flavonol glycosides with antibacterial activity from root barks of Sophora japonica . Wood Sci Technol 50, 645–659 (2016). https://doi.org/10.1007/s00226-016-0809-1

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  • DOI: https://doi.org/10.1007/s00226-016-0809-1

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