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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2020
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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. |
format | Online Article Text |
id | pubmed-7601204 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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