Isolation and Total Synthesis of Bromoiesol sulfates, Antitrypanosomal arylethers from a <i>Salileptolyngbya</i> sp. Marine Cyanobacterium
Akira Ebihara, Arihiro Iwasaki, Youhei Miura, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga
Abstract
Bromoiesol sulfates A ( 1 ) and B ( 2 ), new polyhalogenated aryl sulfates, were isolated from a Salileptolyngbya sp. marine cyanobacterium along with their hydrolyzed compounds, bromoiesols A ( 3 ) and B ( 4 ). To pick up the candidates of their structures, we used Small Molecule Accurate Recognition Technology (SMART), an artificial intelligence-based structure-prediction tool, and their structures were elucidated on the basis of single-crystal X-ray diffraction analysis of bromoiesols ( 3 and 4 ). In addition, to verify the structures, the total synthesis of bromoiesol A sulfate ( 1 ) and bromoiesol A ( 3 ) was achieved. The bromoiesol family, especially bromoiesols ( 3 and 4 ), selectively inhibited the growth of the bloodstream form of Trypanosoma brucei rhodesiense, the causative agent of human African sleeping sickness.