New potentiators of amphotericin B activity, shodoamides A to C produced by Pseudophialophora sp. BF-0158

Akiho Yagi; Masahiro Kashima; Hiroyuki Ishijima; Hiroshi Tomoda; Ryuji Uchida

doi:10.1038/s41429-023-00642-x

New potentiators of amphotericin B activity, shodoamides A to C produced by Pseudophialophora sp. BF-0158

J Antibiot (Tokyo). 2023 Oct;76(10):579-584. doi: 10.1038/s41429-023-00642-x. Epub 2023 Jul 21.

Authors

Akiho Yagi¹, Masahiro Kashima², Hiroyuki Ishijima², Hiroshi Tomoda^{3

4}, Ryuji Uchida⁵

Affiliations

¹ Division of Natural Product Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan.
² Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
³ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.
⁴ Drug Discovery Laboratory, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. tomodah@pharm.kitasato-u.ac.jp.
⁵ Division of Natural Product Chemistry, Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, Miyagi, 981-8558, Japan. uchidar@tohoku-mpu.ac.jp.

PMID: 37479741
DOI: 10.1038/s41429-023-00642-x

Abstract

During our screening program for new potentiators of amphotericin B activity against Candida albicans, shodoamides A to C (1-3) were isolated from a culture broth of the fungus Pseudophialophora sp. BF-0158 fermented under shaking conditions. A known congener named shodoamide D (4) in this paper was obtained from a culture broth of the BF-0158 strain fermented under static conditions. The structures of 1-4 were assigned based on spectroscopic analyses, including NMR and MS, and were found to have a common N-(2´,3´,4´-trihydroxybutyl)-6-methyl-2,4-tetradecadienamide structure. Compounds 1-3 exhibited no antifungal activity, but they induced up to 32-fold increases in amphotericin B activity against C. albicans by a microdilution method.