Paranazzamides A and B, new cyclic dipeptides containing a C7-prenylated tryptophan, produced by pathogenic reptile fungi Paranannizziopsis sp. UH-21

Keisuke Kobayashi; Rio Tejima; Kenichiro Nagai; Reiko Seki; Tsuyoshi Hosoya; Yumi Une; Satoru Shigeno; Hiroshi Tomoda; Taichi Ohshiro

doi:10.1038/s41429-024-00725-3

Paranazzamides A and B, new cyclic dipeptides containing a C7-prenylated tryptophan, produced by pathogenic reptile fungi Paranannizziopsis sp. UH-21

J Antibiot (Tokyo). 2024 May 15. doi: 10.1038/s41429-024-00725-3. Online ahead of print.

Authors

Keisuke Kobayashi^#^{1

2}, Rio Tejima^#¹, Kenichiro Nagai², Reiko Seki², Tsuyoshi Hosoya³, Yumi Une⁴, Satoru Shigeno^{1

2}, Hiroshi Tomoda¹, Taichi Ohshiro^{5

6}

Affiliations

¹ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
² Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
³ Department of Botany, National Museum of Nature and Science, 4-4-1 Amakubo, Tsukuba, Ibaraki, 305-0005, Japan.
⁴ Laboratory of Veterinary Pathology, Okayama University of Science, 1-3 Ikoinooka, Imabari, Ehime, Japan.
⁵ Department of Microbial Chemistry, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. ohshirot@pharm.kitasato-u.ac.jp.
⁶ Medicinal Research Laboratories, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan. ohshirot@pharm.kitasato-u.ac.jp.

^# Contributed equally.

PMID: 38750250
DOI: 10.1038/s41429-024-00725-3

Abstract

Two new cyclic dipeptides, paranazzamides A (1) and B (2) containing a C7-prenylated tryptophan, were isolated from a culture broth of snake fungal disease-isolate Paranannizziopsis sp. UH-21. This is the first report on the new secondary metabolites from Paranannizziopsis sp. The planar structures of 1 and 2 were elucidated using various spectroscopic techniques including MS and 1D/2D NMR. The absolute configuration of 1 was assigned by comparison with the synthesized compound. Compounds 1 and 2 exhibited no antifungal activity, no antibacterial activity, and no cytotoxic activity even at a concentration of 128 µg ml^-1, whereas 1 and 2 exhibited amphotericin B potentiating activity against Candida auris in combination treatment.