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Article

Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents

by
Xiang Yu
1,†,
Xun Song
2,3,†,
Yi Zhang
1,†,
Yemeng Yang
2,†,
Jianghai Ye
1,
Yahua Liu
1,
Lutai Pan
1,* and
Hongjie Zhang
2,*
1
The Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China
2
School of Chinese Medicine, Hong Kong Baptist University, Hong Kong 999077, China
3
College of Pharmacy, Shenzhen Technology University, Shenzhen 518118, China
*
Authors to whom correspondence should be addressed.
†
These authors contribute equally to this work.
Molecules 2022, 27(20), 6836; https://doi.org/10.3390/molecules27206836
Submission received: 20 September 2022 / Revised: 10 October 2022 / Accepted: 10 October 2022 / Published: 12 October 2022
(This article belongs to the Special Issue Discovery of Bioactive Ingredients from Natural Products, 3rd Edition)
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Abstract

In order to discover more promising antifungal and antibacterial agents, a series of new derivatives were designed and synthesized by structure modification based on the naturally occurring antimicrobial compound lophanic acid. The structures of all the target compounds were well characterized by spectroscopic data. The stereochemistry of these compounds was further determined through the X-ray diffraction analysis of 6a. The synthetic compounds were evaluated for their antimicrobial activities against filamentous fungi (T. rubrum, T. mentagrophytes), yeasts (C. neoformans, C. albicans) and Gram-positive and Gram-negative bacteria (MRSA, S. mutans, S. sobrinus, and E. coli). Among them, 3d and 3i are found as the most promising leads that showed potent inhibitory effects against all the tested fungal and bacterial strains except for E. coli. The presence of the C-20 carboxylic ester groups and the free hydroxy group at C-13 was found to be essential for the antifungal and antibacterial activities of the lophanic acid derivatives.
Keywords: lophanic acid; antifungal activity; antibacterial activity; structural modification lophanic acid; antifungal activity; antibacterial activity; structural modification

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MDPI and ACS Style

Yu, X.; Song, X.; Zhang, Y.; Yang, Y.; Ye, J.; Liu, Y.; Pan, L.; Zhang, H. Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents. Molecules 2022, 27, 6836. https://doi.org/10.3390/molecules27206836

AMA Style

Yu X, Song X, Zhang Y, Yang Y, Ye J, Liu Y, Pan L, Zhang H. Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents. Molecules. 2022; 27(20):6836. https://doi.org/10.3390/molecules27206836

Chicago/Turabian Style

Yu, Xiang, Xun Song, Yi Zhang, Yemeng Yang, Jianghai Ye, Yahua Liu, Lutai Pan, and Hongjie Zhang. 2022. "Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents" Molecules 27, no. 20: 6836. https://doi.org/10.3390/molecules27206836

APA Style

Yu, X., Song, X., Zhang, Y., Yang, Y., Ye, J., Liu, Y., Pan, L., & Zhang, H. (2022). Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents. Molecules, 27(20), 6836. https://doi.org/10.3390/molecules27206836

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