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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...

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Autores principales: 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.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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