Anthraquinone Derivatives and Other Aromatic Compounds from Marine Fungus Asteromyces cruciatus KMM 4696 and Their Effects against Staphylococcus aureus
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Published:2023-07-29
Issue:8
Volume:21
Page:431
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ISSN:1660-3397
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Container-title:Marine Drugs
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language:en
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Short-container-title:Marine Drugs
Author:
Zhuravleva Olesya I.12ORCID, Chingizova Ekaterina A.1, Oleinikova Galina K.1, Starnovskaya Sofya S.1, Antonov Alexandr S.1, Kirichuk Natalia N.1, Menshov Alexander S.1, Popov Roman S.1ORCID, Kim Natalya Yu.1, Berdyshev Dmitrii V.1, Chingizov Artur R.1, Kuzmich Alexandra S.1, Guzhova Irina V.3ORCID, Yurchenko Anton N.1ORCID, Yurchenko Ekaterina A.1ORCID
Affiliation:
1. G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Vladivostok 690022, Russia 2. Institute of High Technologies and Advanced Materials, Far Eastern Federal University, 10 Ajax Bay, Russky Island, Vladivostok 690922, Russia 3. Institute of Cytology Russian Academy of Sciences, Tikhoretskiy Ave. 4, St. Petersburg 194064, Russia
Abstract
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.
Funder
Russian Science Foundation
Subject
Drug Discovery,Pharmacology, Toxicology and Pharmaceutics (miscellaneous),Pharmaceutical Science
Reference43 articles.
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