Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain <i>Penicillium steckii</i> FKJ-0213
Hirotaka Matsuo,
Rei Hokari,
Aki Ishiyama,
Masato Iwatsuki,
Mayuka Higo,
Kenichi Nonaka,
Yuriko Nagano,
Yōko Takahashi,
Satoshi Ōmura,
Takuji Nakashima
Affiliations
Hirotaka Matsuo
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Rei Hokari
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Aki Ishiyama
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Masato Iwatsuki
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Mayuka Higo
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Kenichi Nonaka
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Yuriko Nagano
Department of Marine Biodiversity Research, Japan Agency for Marine-Earth Science and Technology, 2-15 Natsushima-cho, Yokosuka, Kanagawa 237-0061, Japan
Yōko Takahashi
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Satoshi Ōmura
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
Takuji Nakashima
Ōmura Satoshi Memorial Institute, Kitasato University, 5-9-1 Shirokane, Minatok-ku, Tokyo 108-8641, Japan
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.
