New antimalarial fusarochromanone analogs produced by the fungal strain Fusarium sp. FKI-9521

Yoshihiro Watanabe; Emi Arakawa; Naozumi Kondo; Kenichi Nonaka; Akari Ikeda; Tomoyasu Hirose; Toshiaki Sunazuka; Rei Hokari; Aki Ishiyama; Masato Iwatsuki

doi:10.1038/s41429-023-00617-y

New antimalarial fusarochromanone analogs produced by the fungal strain Fusarium sp. FKI-9521

J Antibiot (Tokyo). 2023 Jul;76(7):384-391. doi: 10.1038/s41429-023-00617-y. Epub 2023 Apr 12.

Authors

Yoshihiro Watanabe^#^{1

2}, Emi Arakawa^#², Naozumi Kondo², Kenichi Nonaka^{1

2}, Akari Ikeda^{1

2}, Tomoyasu Hirose^{1

2}, Toshiaki Sunazuka^{1

2}, Rei Hokari^{1

2}, Aki Ishiyama^{3

4}, Masato Iwatsuki^{5

6}

Affiliations

¹ Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
² Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
³ Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. ishiyama@lisci.kitasato-u.ac.jp.
⁴ Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. ishiyama@lisci.kitasato-u.ac.jp.
⁵ Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. iwatuki@lisci.kitasato-u.ac.jp.
⁶ Graduate School of Infection Control Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. iwatuki@lisci.kitasato-u.ac.jp.

^# Contributed equally.

PMID: 37041319
DOI: 10.1038/s41429-023-00617-y

Abstract

Two new antimalarial compounds, named deacetyl fusarochromene (1) and 4'-O-acetyl fusarochromanone (2), were discovered from the static fungal cultured material of Fusarium sp. FKI-9521 isolated from feces of a stick insect (Ramulus mikado) together with three known compounds fusarochromanone (3), 3'-N-acetyl fusarochromanone (4), and 5 (fusarochromene or banchromene). The structures of 1 and 2 were elucidated as new analogs of 3 by MS and NMR analyses. The absolute configurations of 1, 2, and 4 were determined by chemical derivatization. All five compounds showed moderate in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, with IC₅₀ values ranging from 0.08 to 6.35 µM.

Publication types

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

MeSH terms

Antimalarials* / chemistry
Antimalarials* / pharmacology
Chloroquine / pharmacology
Chromones
Fusarium*
Plasmodium falciparum

Substances

Antimalarials
fusarochromanone
Chloroquine
Chromones