Kozupeptins, Antimalarial Agents Produced by Paracamarosporium Species: Isolation, Structural Elucidation, Total Synthesis, and Bioactivity

Yumi Hayashi; Wataru Fukasawa; Tomoyasu Hirose; Masato Iwatsuki; Rei Hokari; Aki Ishiyama; Masahiro Kanaida; Kenichi Nonaka; Akira Take; Kazuhiko Otoguro; Satoshi Omura; Kazuro Shiomi; Toshiaki Sunazuka

doi:10.1021/acs.orglett.9b00483

Kozupeptins, Antimalarial Agents Produced by Paracamarosporium Species: Isolation, Structural Elucidation, Total Synthesis, and Bioactivity

Yumi Hayashi, Wataru Fukasawa, Tomoyasu Hirose, Masato Iwatsuki, Rei Hokari, Aki Ishiyama, Masahiro Kanaida, Kenichi Nonaka, Akira Take, Kazuhiko Otoguro, Satoshi Omura, Kazuro Shiomi^*, Toshiaki Sunazuka

^*Corresponding author for this work

Research Organization for Nano & Life Innovation

Research output: Contribution to journal › Article › peer-review

14 Citations (Scopus)

Abstract

Kozupeptins A and B, novel antimalarial lipopeptides, were isolated from the culture broths of Paracamarosporium sp. FKI-7019. They exhibited potent antimalarial activity against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. The structural elucidation was accomplished by a combination of spectroscopic analyses and chemical approaches including a total synthesis of kozupeptin A. Synthetic kozupeptin A demonstrated a therapeutic effect in vivo, and an intermediate exhibited much higher antimalarial activity than kozupeptin A.

Original language	English
Journal	Organic Letters
DOIs	https://doi.org/10.1021/acs.orglett.9b00483
Publication status	Published - 2019 Jan 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Hayashi, Y., Fukasawa, W., Hirose, T., Iwatsuki, M., Hokari, R., Ishiyama, A., Kanaida, M., Nonaka, K., Take, A., Otoguro, K., Omura, S., Shiomi, K., & Sunazuka, T. (2019). Kozupeptins, Antimalarial Agents Produced by Paracamarosporium Species: Isolation, Structural Elucidation, Total Synthesis, and Bioactivity. Organic Letters. https://doi.org/10.1021/acs.orglett.9b00483

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T2 - Isolation, Structural Elucidation, Total Synthesis, and Bioactivity

AU - Hayashi, Yumi

AU - Fukasawa, Wataru

AU - Hirose, Tomoyasu

AU - Iwatsuki, Masato

AU - Hokari, Rei

AU - Ishiyama, Aki

AU - Kanaida, Masahiro

AU - Nonaka, Kenichi

AU - Take, Akira

AU - Otoguro, Kazuhiko

AU - Omura, Satoshi

AU - Shiomi, Kazuro

AU - Sunazuka, Toshiaki

PY - 2019/1/1

Y1 - 2019/1/1

N2 - Kozupeptins A and B, novel antimalarial lipopeptides, were isolated from the culture broths of Paracamarosporium sp. FKI-7019. They exhibited potent antimalarial activity against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. The structural elucidation was accomplished by a combination of spectroscopic analyses and chemical approaches including a total synthesis of kozupeptin A. Synthetic kozupeptin A demonstrated a therapeutic effect in vivo, and an intermediate exhibited much higher antimalarial activity than kozupeptin A.

AB - Kozupeptins A and B, novel antimalarial lipopeptides, were isolated from the culture broths of Paracamarosporium sp. FKI-7019. They exhibited potent antimalarial activity against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. The structural elucidation was accomplished by a combination of spectroscopic analyses and chemical approaches including a total synthesis of kozupeptin A. Synthetic kozupeptin A demonstrated a therapeutic effect in vivo, and an intermediate exhibited much higher antimalarial activity than kozupeptin A.

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Kozupeptins, Antimalarial Agents Produced by Paracamarosporium Species: Isolation, Structural Elucidation, Total Synthesis, and Bioactivity

Abstract

ASJC Scopus subject areas

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