New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities
Two new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus <i>Penicillium antarcticum</i> KMM 4670, which was re-identified based on phylogenetic inference from ITS, <i>BenA</i&...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/21/11/584 |
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| author | Anton N. Yurchenko Olesya I. Zhuravleva Olga O. Khmel Galina K. Oleynikova Alexandr S. Antonov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovsky Dmitry V. Berdyshev Natalya Y. Kim Roman S. Popov Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Ekaterina A. Yurchenko |
| author_facet | Anton N. Yurchenko Olesya I. Zhuravleva Olga O. Khmel Galina K. Oleynikova Alexandr S. Antonov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovsky Dmitry V. Berdyshev Natalya Y. Kim Roman S. Popov Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Ekaterina A. Yurchenko |
| author_sort | Anton N. Yurchenko |
| collection | DOAJ |
| description | Two new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus <i>Penicillium antarcticum</i> KMM 4670, which was re-identified based on phylogenetic inference from ITS, <i>BenA</i>, <i>CaM</i>, and <i>RPB2</i> gene regions. The absolute stereostructures of the isolated cyclopianes were determined using modified Mosher’s method and quantum chemical calculations of the ECD spectra. The isolation from the natural source of two biosynthetic precursors of cladosporin from a natural source has been reported for the first time. The antimicrobial activities of the isolated compounds against <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> as well as the inhibition of staphylococcal sortase A activity were investigated. Moreover, the cytotoxicity of the compounds to mammalian cardiomyocytes H9c2 was studied. As a result, new cyclopiane diterpene 13-<i>epi</i>-conidiogenone F was found to be a sortase A inhibitor and a promising anti-staphylococcal agent. |
| first_indexed | 2024-03-09T16:39:35Z |
| format | Article |
| id | doaj.art-e1194dfb9b7a44258c4cff478ab6321f |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T16:39:35Z |
| publishDate | 2023-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-e1194dfb9b7a44258c4cff478ab6321f2023-11-24T14:53:13ZengMDPI AGMarine Drugs1660-33972023-11-01211158410.3390/md21110584New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological ActivitiesAnton N. Yurchenko0Olesya I. Zhuravleva1Olga O. Khmel2Galina K. Oleynikova3Alexandr S. Antonov4Natalya N. Kirichuk5Viktoria E. Chausova6Anatoly I. Kalinovsky7Dmitry V. Berdyshev8Natalya Y. Kim9Roman S. Popov10Ekaterina A. Chingizova11Artur R. Chingizov12Marina P. Isaeva13Ekaterina A. Yurchenko14G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaInstitute of High Technologies and Advanced Materials, Far Eastern Federal University, 10 Ajax Bay, Russky Island, Vladivostok 690922, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Prospect 100-Letiya Vladivostoka, 159, Russky Island, Vladivostok 690022, RussiaTwo new cyclopiane diterpenes and a new cladosporin precursor, together with four known related compounds, were isolated from the marine sediment-derived fungus <i>Penicillium antarcticum</i> KMM 4670, which was re-identified based on phylogenetic inference from ITS, <i>BenA</i>, <i>CaM</i>, and <i>RPB2</i> gene regions. The absolute stereostructures of the isolated cyclopianes were determined using modified Mosher’s method and quantum chemical calculations of the ECD spectra. The isolation from the natural source of two biosynthetic precursors of cladosporin from a natural source has been reported for the first time. The antimicrobial activities of the isolated compounds against <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> as well as the inhibition of staphylococcal sortase A activity were investigated. Moreover, the cytotoxicity of the compounds to mammalian cardiomyocytes H9c2 was studied. As a result, new cyclopiane diterpene 13-<i>epi</i>-conidiogenone F was found to be a sortase A inhibitor and a promising anti-staphylococcal agent.https://www.mdpi.com/1660-3397/21/11/584<i>Penicillium antarcticum</i>phylogenyre-identificationcyclopianespolyketidesantimicrobial activity |
| spellingShingle | Anton N. Yurchenko Olesya I. Zhuravleva Olga O. Khmel Galina K. Oleynikova Alexandr S. Antonov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovsky Dmitry V. Berdyshev Natalya Y. Kim Roman S. Popov Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Ekaterina A. Yurchenko New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities Marine Drugs <i>Penicillium antarcticum</i> phylogeny re-identification cyclopianes polyketides antimicrobial activity |
| title | New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities |
| title_full | New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities |
| title_fullStr | New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities |
| title_full_unstemmed | New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities |
| title_short | New Cyclopiane Diterpenes and Polyketide Derivatives from Marine Sediment-Derived Fungus <i>Penicillium antarcticum</i> KMM 4670 and Their Biological Activities |
| title_sort | new cyclopiane diterpenes and polyketide derivatives from marine sediment derived fungus i penicillium antarcticum i kmm 4670 and their biological activities |
| topic | <i>Penicillium antarcticum</i> phylogeny re-identification cyclopianes polyketides antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/21/11/584 |
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