Institute of Biomolecule Reconstruction (iBR), Department of Life Science and Biochemical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, Korea.
Department of Biotechnology and Pharmaceutical Engineering, Sun Moon University, 70 Sun Moon-ro 221, Tangjeong-myeon, Asan-si 31460, Chungnam, Korea.
Molecules. 2022 Aug 29;27(17):5554. doi: 10.3390/molecules27175554.
Anthraquinone and its derivatives show remarkable biological properties such as anticancer, antibacterial, antifungal, and antiviral activities. Hence, anthraquinones derivatives have been of prime interest in drug development. This study developed a recombinant Escherichia coli strain to modify chrysazin to chrysazin-8-O-α-l-rhamnoside (CR) and chrysazin-8-O-α-l-2′-O-methylrhamnoside (CRM) using rhamnosyl transferase and sugar-O-methyltransferase. Biosynthesized CR and CRM were structurally characterized using HPLC, high-resolution mass spectrometry, and various nuclear magnetic resonance analyses. Antimicrobial effects of chrysazin, CR, and CRM against 18 superbugs, including 14 Gram-positive and 4 Gram-negative pathogens, were investigated. CR and CRM exhibited antimicrobial activities against nine pathogens, including methicillin-resistant Staphylococcus aureus (MRSA) and methicillin-sensitive Staphylococcus aureus (MSSA) in a disk diffusion assay at a concentration of 40 µg per disk. There were MIC and MBC values of 7.81−31.25 µg/mL for CR and CRM against methicillin-sensitive S. aureus CCARM 0205 (MSSA) for which the parent chrysazin is more than >1000 µg/mL. Furthermore, the anti-proliferative properties of chrysazin, CR, and CRM were assayed using AGS, Huh7, HL60, and HaCaT cell lines. CR and CRM showed higher antibacterial and anticancer properties than chrysazin.
蒽醌及其衍生物具有显著的生物活性，如抗癌、抗菌、抗真菌和抗病毒活性。因此，蒽醌衍生物一直是药物开发的重点。本研究利用糖基转移酶和糖-O-甲基转移酶，构建了一株重组大肠杆菌，将色满酮修饰为色满酮-8-O-α-L-鼠李糖苷（CR）和色满酮-8-O-α-L-2′-O-甲基鼠李糖苷（CRM）。采用 HPLC、高分辨质谱和各种核磁共振分析对生物合成的 CR 和 CRM 进行了结构表征。研究了色满酮、CR 和 CRM 对 18 种超级细菌（包括 14 种革兰氏阳性菌和 4 种革兰氏阴性菌）的抗菌作用。在药敏纸片扩散试验中，CR 和 CRM 在浓度为 40µg/片时对 9 种病原体（包括耐甲氧西林金黄色葡萄球菌（MRSA）和甲氧西林敏感金黄色葡萄球菌（MSSA））具有抗菌活性。CR 和 CRM 对甲氧西林敏感金黄色葡萄球菌 CCARM 0205（MSSA）的 MIC 和 MBC 值分别为 7.81-31.25µg/mL，而色满酮对其 MIC 值大于>1000µg/mL。此外，还采用 AGS、Huh7、HL60 和 HaCaT 细胞系检测了色满酮、CR 和 CRM 的抗增殖特性。CR 和 CRM 显示出比色满酮更高的抗菌和抗癌特性。
