Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents
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 sp...
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| Format: | Article |
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MDPI AG
2022-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/20/6836 |
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| author | Xiang Yu Xun Song Yi Zhang Yemeng Yang Jianghai Ye Yahua Liu Lutai Pan Hongjie Zhang |
| author_facet | Xiang Yu Xun Song Yi Zhang Yemeng Yang Jianghai Ye Yahua Liu Lutai Pan Hongjie Zhang |
| author_sort | Xiang Yu |
| collection | DOAJ |
| description | 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 (<i>T. rubrum, T. mentagrophytes</i>), yeasts (<i>C. neoformans, C. albicans</i>) and Gram-positive and Gram-negative bacteria (<i>MRSA, S. mutans, S. sobrinus,</i> and <i>E. coli</i>). 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 <i>E. coli</i>. 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. |
| first_indexed | 2024-03-09T19:43:07Z |
| format | Article |
| id | doaj.art-20c3157172374850811bffbe3c983495 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T19:43:07Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-20c3157172374850811bffbe3c9834952023-11-24T01:32:02ZengMDPI AGMolecules1420-30492022-10-012720683610.3390/molecules27206836Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial AgentsXiang Yu0Xun Song1Yi Zhang2Yemeng Yang3Jianghai Ye4Yahua Liu5Lutai Pan6Hongjie Zhang7The Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Chinese Medicine, Hong Kong Baptist University, Hong Kong 999077, ChinaThe Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Chinese Medicine, Hong Kong Baptist University, Hong Kong 999077, ChinaThe Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaThe Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaThe Key Laboratory of Miao Medicine of Guizhou Province, School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, ChinaSchool of Chinese Medicine, Hong Kong Baptist University, Hong Kong 999077, ChinaIn 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 (<i>T. rubrum, T. mentagrophytes</i>), yeasts (<i>C. neoformans, C. albicans</i>) and Gram-positive and Gram-negative bacteria (<i>MRSA, S. mutans, S. sobrinus,</i> and <i>E. coli</i>). 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 <i>E. coli</i>. 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.https://www.mdpi.com/1420-3049/27/20/6836lophanic acidantifungal activityantibacterial activitystructural modification |
| spellingShingle | Xiang Yu Xun Song Yi Zhang Yemeng Yang Jianghai Ye Yahua Liu Lutai Pan Hongjie Zhang Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents Molecules lophanic acid antifungal activity antibacterial activity structural modification |
| title | Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents |
| title_full | Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents |
| title_fullStr | Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents |
| title_full_unstemmed | Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents |
| title_short | Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents |
| title_sort | design synthesis and biological evaluation of lophanic acid derivatives as antifungal and antibacterial agents |
| topic | lophanic acid antifungal activity antibacterial activity structural modification |
| url | https://www.mdpi.com/1420-3049/27/20/6836 |
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