Natural Products Research Institute, College of Pharmacy, Seoul National University, Seoul 08826, Korea.
Department of Agriculture Biotechnology, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Korea.
Mar Drugs. 2022 Jan 18;20(2):83. doi: 10.3390/md20020083.
sp. GET02.ST and sp. GET02.AC were isolated together from the gut of the wharf roach, , inhabiting the intertidal zone of the west coast of Korea. The co-cultivation of these two strains significantly induced the production of two new metabolites, ligiamycins A () and B (), which were barely detected in the single culture of sp. GET02.ST. The planar structures of ligiamycins A () and B () were elucidated as new decalins coupled with amino-maleimides by the analysis of various spectroscopic data, including nuclear magnetic resonance (NMR), ultraviolet (UV), and mass (MS) data. The assignment of two nitrogen atoms in amino-maleimide in was accomplished based on H-N heteroatom single quantum coherence spectroscopy (HSQC) NMR experiments. The relative configurations of the ligiamycins were determined using rotating frame Overhauser effect spectroscopy (ROESY) NMR data, and their absolute configurations were deduced by comparing their experimental and calculated optical rotations. Ligiamycin A () displayed antibacterial effects against and , while ligiamycin B () exhibited mild cell cytotoxicity against human colorectal cancer cells.
sp. GET02.ST 和 sp. GET02.AC 是从码头蟑螂的肠道中一起分离出来的,栖息在韩国西海岸的潮间带。这两种菌株的共培养显著诱导产生了两种新的代谢产物,ligiamycins A()和 B(),在 sp. GET02.ST 的单一培养中几乎检测不到。通过分析各种光谱数据,包括核磁共振 (NMR)、紫外线 (UV) 和质谱 (MS) 数据,阐明了 ligiamycins A()和 B()的平面结构是新的十氢化萘与氨基马来酰亚胺偶联而成。通过 H-N 杂原子单量子相干光谱 (HSQC) NMR 实验完成了氨基马来酰亚胺中两个氮原子的分配。通过旋转框架 Overhauser 效应光谱 (ROESY) NMR 数据确定了 ligiamycins 的相对构型,并通过比较实验和计算的旋光来推断它们的绝对构型。Ligiamycin A()对和具有抗菌作用,而 ligiamycin B()对人结肠直肠癌细胞表现出轻微的细胞细胞毒性。