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

Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicillium steckii 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 deter...

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Autores principales: Matsuo, Hirotaka, Hokari, Rei, Ishiyama, Aki, Iwatsuki, Masato, Higo, Mayuka, Nonaka, Kenichi, Nagano, Yuriko, Takahashi, Yōko, Ōmura, Satoshi, Nakashima, Takuji
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7601204/
https://www.ncbi.nlm.nih.gov/pubmed/33053770
http://dx.doi.org/10.3390/md18100513
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author Matsuo, Hirotaka
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Higo, Mayuka
Nonaka, Kenichi
Nagano, Yuriko
Takahashi, Yōko
Ōmura, Satoshi
Nakashima, Takuji
author_facet Matsuo, Hirotaka
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Higo, Mayuka
Nonaka, Kenichi
Nagano, Yuriko
Takahashi, Yōko
Ōmura, Satoshi
Nakashima, Takuji
author_sort Matsuo, Hirotaka
collection PubMed
description Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicillium steckii 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 (1)H-nuclear magnetic resonance ((1)H-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 (IC(50)) 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 IC(50) values of 15.0, 13.7, 12.9, 6.8, and 18.7 μM, respectively.
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spelling pubmed-76012042020-11-01 Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213 Matsuo, Hirotaka Hokari, Rei Ishiyama, Aki Iwatsuki, Masato Higo, Mayuka Nonaka, Kenichi Nagano, Yuriko Takahashi, Yōko Ōmura, Satoshi Nakashima, Takuji Mar Drugs Article Two new nitrogen-containing metabolites, designated hatsusamide A (1) and B (2), were isolated from a culture broth of Penicillium steckii 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 (1)H-nuclear magnetic resonance ((1)H-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 (IC(50)) 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 IC(50) values of 15.0, 13.7, 12.9, 6.8, and 18.7 μM, respectively. MDPI 2020-10-12 /pmc/articles/PMC7601204/ /pubmed/33053770 http://dx.doi.org/10.3390/md18100513 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Matsuo, Hirotaka
Hokari, Rei
Ishiyama, Aki
Iwatsuki, Masato
Higo, Mayuka
Nonaka, Kenichi
Nagano, Yuriko
Takahashi, Yōko
Ōmura, Satoshi
Nakashima, Takuji
Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title_full Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title_fullStr Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title_full_unstemmed Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title_short Hatsusamides A and B: Two New Metabolites Produced by the Deep-Sea-Derived Fungal Strain Penicillium steckii FKJ-0213
title_sort hatsusamides a and b: two new metabolites produced by the deep-sea-derived fungal strain penicillium steckii fkj-0213
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7601204/
https://www.ncbi.nlm.nih.gov/pubmed/33053770
http://dx.doi.org/10.3390/md18100513
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