Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium

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

doi:10.1021/acs.jnatprod.0c00250

Iheyamides A-C, Antitrypanosomal Linear Peptides Isolated from a Marine Dapis sp. Cyanobacterium

J Nat Prod. 2020 May 22;83(5):1684-1690. doi: 10.1021/acs.jnatprod.0c00250. Epub 2020 Apr 30.

Authors

Naoaki Kurisawa¹, 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: 32352773
DOI: 10.1021/acs.jnatprod.0c00250

Abstract

Iheyamides A (1), B (2), and C (3), new linear peptides, were isolated from a marine Dapis sp. cyanobacterium. Their structures were elucidated by spectroscopic analyses and degradation reactions. Iheyamide A (1) showed moderate antitrypanosomal activities against Trypanosoma brucei rhodesiense and Trypanosoma brucei brucei (IC₅₀ = 1.5 μM), but the other two analogues, iheyamides B (2) and C (3), did not (IC₅₀ > 20 μM, respectively). The structure-activity relationship clarified that an isopropyl-O-Me-pyrrolinone moiety was necessary for the antitrypanosomal activity. Furthermore, the cytotoxicity of 1 against normal human cells, WI-38, was 10 times weaker than its antitrypanosomal activity (IC₅₀ = 18 μM).

Publication types

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

MeSH terms

Antiprotozoal Agents / chemistry
Antiprotozoal Agents / pharmacology*
Cell Line
Cyanobacteria / chemistry*
Peptides / chemistry
Peptides / isolation & purification
Peptides / pharmacology*
Structure-Activity Relationship
Trypanosoma brucei brucei / drug effects*
Trypanosoma brucei rhodesiense / drug effects*

Substances

Antiprotozoal Agents
Peptides