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Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus
New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were...
Autores principales: | , , , , , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10455474/ https://www.ncbi.nlm.nih.gov/pubmed/37623712 http://dx.doi.org/10.3390/md21080431 |
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author | Zhuravleva, Olesya I. Chingizova, Ekaterina A. Oleinikova, Galina K. Starnovskaya, Sofya S. Antonov, Alexandr S. Kirichuk, Natalia N. Menshov, Alexander S. Popov, Roman S. Kim, Natalya Yu. Berdyshev, Dmitrii V. Chingizov, Artur R. Kuzmich, Alexandra S. Guzhova, Irina V. Yurchenko, Anton N. Yurchenko, Ekaterina A. |
author_facet | Zhuravleva, Olesya I. Chingizova, Ekaterina A. Oleinikova, Galina K. Starnovskaya, Sofya S. Antonov, Alexandr S. Kirichuk, Natalia N. Menshov, Alexander S. Popov, Roman S. Kim, Natalya Yu. Berdyshev, Dmitrii V. Chingizov, Artur R. Kuzmich, Alexandra S. Guzhova, Irina V. Yurchenko, Anton N. Yurchenko, Ekaterina A. |
author_sort | Zhuravleva, Olesya I. |
collection | PubMed |
description | New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect. |
format | Online Article Text |
id | pubmed-10455474 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-104554742023-08-26 Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus Zhuravleva, Olesya I. Chingizova, Ekaterina A. Oleinikova, Galina K. Starnovskaya, Sofya S. Antonov, Alexandr S. Kirichuk, Natalia N. Menshov, Alexander S. Popov, Roman S. Kim, Natalya Yu. Berdyshev, Dmitrii V. Chingizov, Artur R. Kuzmich, Alexandra S. Guzhova, Irina V. Yurchenko, Anton N. Yurchenko, Ekaterina A. Mar Drugs Article New anthraquinone derivatives acruciquinones A–C (1–3), together with ten known metabolites, were isolated from the obligate marine fungus Asteromyces cruciatus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A–C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds 1–4 and 6–13 showed a significant antimicrobial effects against Staphylococcus aureus growth, and acruciquinone A (1), dendryol B (4), coniothyrinone B (7), and ω-hydroxypachybasin (9) reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding 4, inhibited urease activity. We studied the effects of anthraquinones 1, 4, 7, and 9 and coniothyrinone D (6) in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with S. aureus. Anthraquinones significantly reduce the negative impact of S. aureus on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A (1) revealed the most pronounced effect. MDPI 2023-07-29 /pmc/articles/PMC10455474/ /pubmed/37623712 http://dx.doi.org/10.3390/md21080431 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Zhuravleva, Olesya I. Chingizova, Ekaterina A. Oleinikova, Galina K. Starnovskaya, Sofya S. Antonov, Alexandr S. Kirichuk, Natalia N. Menshov, Alexander S. Popov, Roman S. Kim, Natalya Yu. Berdyshev, Dmitrii V. Chingizov, Artur R. Kuzmich, Alexandra S. Guzhova, Irina V. Yurchenko, Anton N. Yurchenko, Ekaterina A. Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title | Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title_full | Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title_fullStr | Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title_full_unstemmed | Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title_short | Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus |
title_sort | anthraquinone derivatives and other aromatic compounds from marine fungus asteromyces cruciatus kmm 4696 and their effects against staphylococcus aureus |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10455474/ https://www.ncbi.nlm.nih.gov/pubmed/37623712 http://dx.doi.org/10.3390/md21080431 |
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