Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

Naoaki Kurisawa; Keisuke Otomo; Arihiro Iwasaki; Ghulam Jeelani; Tomoyoshi Nozaki; Kiyotake Suenaga

doi:10.1021/acs.joc.1c00817

Isolation and Total Synthesis of Kinenzoline, an Antitrypanosomal Linear Depsipeptide Isolated from a Marine Salileptolyngbya sp. Cyanobacterium

J Org Chem. 2021 Sep 17;86(18):12528-12536. doi: 10.1021/acs.joc.1c00817. Epub 2021 Aug 31.

Authors

Naoaki Kurisawa¹, Keisuke Otomo¹, Arihiro Iwasaki¹, Ghulam Jeelani², Tomoyoshi Nozaki², Kiyotake Suenaga¹

Affiliations

¹ Department of Chemistry, Faculty of Science and Technology, Keio University, 3-14-1 Hiyoshi, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan.
² Department of Biomedical Chemistry, Graduate School of Medicine, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 34463094
DOI: 10.1021/acs.joc.1c00817

Abstract

Kinenzoline (1), a new linear depsipeptide, was isolated from a marine Salileptolyngbya sp. cyanobacterium. Its structure was elucidated by spectroscopic analyses and degradation reactions. In addition, we achieved a total synthesis of 1 and confirmed its structure. Kinenzoline (1) showed highly selective antiproliferative activity against the causative organism of sleeping sickness, Trypanosoma brucei rhodesiense (IC₅₀ 4.5 μM), compared to normal human cells (WI-38, IC₅₀ > 100 μM). Kinenzoline (1) is a promising lead compound for the development of new antitrypanosomal drugs.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antiprotozoal Agents* / pharmacology
Cyanobacteria*
Depsipeptides* / pharmacology
Humans
Trypanocidal Agents* / pharmacology
Trypanocidal Agents* / therapeutic use
Trypanosomiasis, African* / drug therapy

Substances

Antiprotozoal Agents
Depsipeptides
Trypanocidal Agents