Isolation and Total Synthesis of Bromoiesol sulfates, Antitrypanosomal arylethers from a Salileptolyngbya sp. Marine Cyanobacterium

Akira Ebihara, Arihiro Iwasaki, Youhei Miura, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish
Pages (from-to)11763-11770
Number of pages8
JournalJournal of Organic Chemistry
Volume86
Issue number17
DOIs
Publication statusPublished - 2021 Sep 3

ASJC Scopus subject areas

  • Organic Chemistry

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