April 21, 2020  |  

Isarubrolones Containing a Pyridooxazinium Unit from Streptomyces as Autophagy Activators.

Authors: Li, Linli and Li, Shufen and Jiang, Bingya and Zhang, Miaoqing and Zhang, Jingpu and Yang, Beibei and Li, Li and Yu, Liyan and Liu, Hongyu and You, Xuefu and Hu, Xinxin and Wang, Zhen and Li, Yuhuan and Wu, Linzhuan

Isarubrolones are bioactive polycyclic tropoloalkaloids from Streptomyces. Three new isarubrolones (2-4), together with the known isarubrolone C (1) and isatropolones A (5) and C (6, 3( R)-hydroxyisatropolone A), were identified from Streptomyces sp. CPCC 204095. The structures of these compounds were determined using a combination of mass spectrometry, 1D and 2D NMR spectroscopy, and ECD. Compounds 3 and 4 feature a pyridooxazinium unit, which is rarely seen in natural products. Compound 6 could conjugate with amino acids or amines to expand the structural diversity of isarubrolones with a pentacyclic or hexacyclic core. Importantly, 1 and 3-6 were found to induce complete autophagy.

Journal: Journal of natural products
DOI: 10.1021/acs.jnatprod.8b00857
Year: 2019

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