Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium

Keitaro Iwasaki; Arihiro Iwasaki; Shimpei Sumimoto; Teruhiko Matsubara; Toshinori Sato; Tomoyoshi Nozaki; Yumiko Saito-Nakano; Kiyotake Suenaga

doi:10.1021/acs.jnatprod.9b01147

Ikoamide, an Antimalarial Lipopeptide from an Okeania sp. Marine Cyanobacterium

J Nat Prod. 2020 Feb 28;83(2):481-488. doi: 10.1021/acs.jnatprod.9b01147. Epub 2020 Feb 10.

Authors

Keitaro Iwasaki¹, Arihiro Iwasaki¹, Shimpei Sumimoto¹, Teruhiko Matsubara², Toshinori Sato², Tomoyoshi Nozaki³, Yumiko Saito-Nakano⁴, 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 Biosciences and Informatics, Faculty of Science and Technology , Keio University , 3-14-1 Hiyoshi , Kohoku-ku, Yokohama , Kanagawa 223-8522 , Japan.
³ Department of Biomedical Chemistry, Graduate School of Medicine , The University of Tokyo , 7-3-1 Hongo , Bunkyo-ku, Tokyo 113-0033 , Japan.
⁴ Department of Parasitology , National Institute of Infectious Diseases , 1-23-1 Toyama , Shinjuku-ku, Tokyo 162-8640 , Japan.

PMID: 32040324
DOI: 10.1021/acs.jnatprod.9b01147

Abstract

An antimalarial lipopeptide, ikoamide, was isolated from an Okeania sp. marine cyanobacterium. Its gross structure was established by spectroscopic analyses, and the absolute configuration was clarified based on a combination of chiral-phase HPLC analyses, spectroscopic analyses, and derivatization reactions. Ikoamide showed strong antimalarial activity with an IC₅₀ value of 0.14 μM without cytotoxicity against human cancer cell lines at 10 μM.

Publication types

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

MeSH terms

Antimalarials / chemistry
Antimalarials / pharmacology*
Chromatography, High Pressure Liquid
Cyanobacteria / chemistry*
Humans
Lipopeptides / chemistry*
Lipopeptides / isolation & purification
Molecular Structure
Structure-Activity Relationship

Substances

Antimalarials
Lipopeptides