Natural Products Research Institute, College of Pharmacy , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
Department of Agricultural Biotechnology, College of Agriculture & Life Sciences , Seoul National University , 1 Gwanak-ro , Gwanak-gu , Seoul 08826 , Republic of Korea.
J Nat Prod. 2020 Feb 28;83(2):277-285. doi: 10.1021/acs.jnatprod.9b00678. Epub 2020 Feb 19.
The cultivation of a sp. SD53 strain isolated from the gut of the silkworm produced two macrolactam natural products, piceamycin () and bombyxamycin C (). The planar structures of and were identified by a combination of NMR, MS, and UV spectroscopic analyses. The absolute configurations were assigned based on chemical and chromatographic methods as well as ECD calculations. A new chromatography-based experimental method for determining the configurations of stereogenic centers β to nitrogen atoms in macrolactams was established and successfully applied in this report. These compounds exhibited significant bioactivities against the silkworm entomopathogen and various human pathogens as well as human cancer cell lines. In particular, piceamycin potently inhibited and with MIC values of 0.083 μg/mL and 0.025 μg/mL, respectively. The biosynthetic pathway involved in the formation of the cyclopentenone moiety in piceamycin is discussed.
从家蚕肠道中分离得到的一株 sp. SD53 菌株培养生产了两种大环内酯类天然产物，即皮沙霉素（）和桑黄素 C（）。通过 NMR、MS 和 UV 光谱分析相结合的方法确定了 和 的平面结构。根据化学和色谱方法以及 ECD 计算确定了绝对构型。建立了一种新的基于色谱的实验方法，用于确定β-氮原子立体中心构型的大环内酯化合物，该方法在本报告中得到了成功应用。这些化合物对家蚕昆虫病原体 和各种人类病原体以及人类癌细胞系表现出显著的生物活性。特别是，皮沙霉素对 和 的抑制作用较强，MIC 值分别为 0.083 μg/mL 和 0.025 μg/mL。讨论了皮沙霉素中环戊烯酮部分形成的生物合成途径。
