TY - JOUR
T1 - Design, Synthesis and Biological Evaluation of Lophanic Acid Derivatives as Antifungal and Antibacterial Agents
AU - Yu, Xiang
AU - Song, Xun
AU - Zhang, Yi
AU - Yang, Yemeng
AU - Ye, Jianghai
AU - Liu, Yahua
AU - Pan, Lutai
AU - Zhang, Hongjie
N1 - Funding Information:
The work described in this study was financially supported by the Research Grant Council of the Hong Kong Special Administrative Region, China (Project No. HKBU12102219), the Tip-top Talent Foundation [grant number KY (2021)034]; National Key R&D Program of China (2019YFC1712501); Guizhou Provincial Natural Science Foundation (QKH-J(2020)1Y070); the University stability support program of Shenzhen (20200813201847001); Guangdong Basic and Applied Basic Research Foundation (2020A1515111169); the Technology Fund of Guizhou Administration of Traditional Chinese Medicine [grant number QZYY-2022-019].
Publisher Copyright:
© 2022 by the authors.
PY - 2022/10/12
Y1 - 2022/10/12
N2 - 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.
AB - 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.
KW - antibacterial activity
KW - antifungal activity
KW - lophanic acid
KW - structural modification
UR - http://www.scopus.com/inward/record.url?scp=85140888832&partnerID=8YFLogxK
U2 - 10.3390/molecules27206836
DO - 10.3390/molecules27206836
M3 - Journal article
C2 - 36296430
SN - 1420-3049
VL - 27
JO - Molecules
JF - Molecules
IS - 20
M1 - 6836
ER -