Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213

Hirotaka Matsuo, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Mayuka Higo, Kenichi Nonaka, Yuriko Nagano, Yōko Takahashi, Satoshi Ōmura, Takuji Nakashima

Research output: Contribution to journalArticlepeer-review

Abstract

Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicilliumsteckii FKJ-0213 together with the known compounds tanzawaic acid B (3) and trichodermamide C (4) by physicochemical (PC) screening. The structures of 1 and 2 were determined as a tanzawaic acid B-trichodermamide C hybrid structure and a new analog of aspergillazines, respectively. The absolute configuration of 1 was determined by comparing the values of tanzawaic acid B and trichodermamide C in the literatures, such as 1H-nuclear magnetic resonance (1H-NMR) data and optical rotation, after hydrolysis of 1. Compounds 1-4 were evaluated for cytotoxicity and anti-malarial activities. Compounds 1 and 3 exhibited weak anti-malarial activity at half-maximal inhibitory concentration (IC50) values of 27.2 and 78.5 µM against the K1 strain, and 27.9 and 79.2 µM against the FCR3 strain of Plasmodium falciparum, respectively. Furthermore, 1 exhibited cytotoxicity against HeLa S3, A549, Panc1, HT29 and H1299 cells, with IC50 values of 15.0, 13.7, 12.9, 6.8, and 18.7 μM, respectively.

Original languageEnglish
JournalMarine Drugs
Volume18
Issue number10
DOIs
Publication statusPublished - 2020 Oct 12

Keywords

  • anti-malarial activity
  • anti-tumor activity
  • deep-sea-derived fungus
  • hatsusamides A and B
  • tanzawaic acid B
  • trichodermamide C

ASJC Scopus subject areas

  • Drug Discovery

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