Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747
The marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin <i>Scaphechinus mirabilis</i> as a natural fungal complex were identified as <i>Penicillium sajarovii</i> and <i>Aspergillus protuberus</i> based on Internal Transcribed Spacer (<i...
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MDPI AG
2023-11-01
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| author | Elena V. Leshchenko Dmitrii V. Berdyshev Ekaterina A. Yurchenko Alexandr S. Antonov Gleb V. Borkunov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovskiy Roman S. Popov Yuliya V. Khudyakova Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Anton N. Yurchenko |
| author_facet | Elena V. Leshchenko Dmitrii V. Berdyshev Ekaterina A. Yurchenko Alexandr S. Antonov Gleb V. Borkunov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovskiy Roman S. Popov Yuliya V. Khudyakova Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Anton N. Yurchenko |
| author_sort | Elena V. Leshchenko |
| collection | DOAJ |
| description | The marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin <i>Scaphechinus mirabilis</i> as a natural fungal complex were identified as <i>Penicillium sajarovii</i> and <i>Aspergillus protuberus</i> based on Internal Transcribed Spacer (<i>ITS</i>), partial β-tubulin (<i>BenA</i>), and calmodulin (<i>CaM</i>) molecular markers as well as an ribosomal polymerase two, subunit two (<i>RPB2</i>) region for KMM 4747. From the ethyl acetate extract of the co-culture, two new polyketides, sajaroketides A (<b>1</b>) and B (<b>2</b>), together with (2′S)-7-hydroxy-2-(2′-hydroxypropyl)-5-methylchromone (<b>3</b>), altechromone A (<b>4</b>), norlichexanthone (<b>5</b>), griseoxanthone C (<b>6</b>), 1,3,5,6-tetrahydroxy-8-methylxanthone (<b>7</b>), griseofulvin (<b>8</b>), 6-O-desmethylgriseofulvin (<b>9</b>), dechlorogriseofulvin (<b>10</b>), and 5,6-dihydro-4-methyl-2H-pyran-2-one (<b>11</b>) were identified. The structures of the compounds were elucidated using spectroscopic analyses. The absolute configurations of the chiral centers of sajaroketides A and B were determined using time-dependent density functional theory (TDDFT)-based calculations of the Electronic Circular Dichroism (ECD) spectra. The inhibitory effects of these compounds on urease activity and the growth of <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> were observed. Sajaroketide A, altechromone A, and griseofulvin showed significant cardioprotective effects in an in vitro model of <i>S. aureus</i>-induced infectious myocarditis. |
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| spelling | doaj.art-03eae8136a7649d1816c7cc0954b4f712023-12-08T15:16:21ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-11-0124231656810.3390/ijms242316568Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747Elena V. Leshchenko0Dmitrii V. Berdyshev1Ekaterina A. Yurchenko2Alexandr S. Antonov3Gleb V. Borkunov4Natalya N. Kirichuk5Viktoria E. Chausova6Anatoly I. Kalinovskiy7Roman S. Popov8Yuliya V. Khudyakova9Ekaterina A. Chingizova10Artur R. Chingizov11Marina P. Isaeva12Anton N. Yurchenko13G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaG.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok 690022, RussiaThe marine-derived fungal strains KMM 4718 and KMM 4747 isolated from sea urchin <i>Scaphechinus mirabilis</i> as a natural fungal complex were identified as <i>Penicillium sajarovii</i> and <i>Aspergillus protuberus</i> based on Internal Transcribed Spacer (<i>ITS</i>), partial β-tubulin (<i>BenA</i>), and calmodulin (<i>CaM</i>) molecular markers as well as an ribosomal polymerase two, subunit two (<i>RPB2</i>) region for KMM 4747. From the ethyl acetate extract of the co-culture, two new polyketides, sajaroketides A (<b>1</b>) and B (<b>2</b>), together with (2′S)-7-hydroxy-2-(2′-hydroxypropyl)-5-methylchromone (<b>3</b>), altechromone A (<b>4</b>), norlichexanthone (<b>5</b>), griseoxanthone C (<b>6</b>), 1,3,5,6-tetrahydroxy-8-methylxanthone (<b>7</b>), griseofulvin (<b>8</b>), 6-O-desmethylgriseofulvin (<b>9</b>), dechlorogriseofulvin (<b>10</b>), and 5,6-dihydro-4-methyl-2H-pyran-2-one (<b>11</b>) were identified. The structures of the compounds were elucidated using spectroscopic analyses. The absolute configurations of the chiral centers of sajaroketides A and B were determined using time-dependent density functional theory (TDDFT)-based calculations of the Electronic Circular Dichroism (ECD) spectra. The inhibitory effects of these compounds on urease activity and the growth of <i>Staphylococcus aureus</i>, <i>Escherichia coli</i>, and <i>Candida albicans</i> were observed. Sajaroketide A, altechromone A, and griseofulvin showed significant cardioprotective effects in an in vitro model of <i>S. aureus</i>-induced infectious myocarditis.https://www.mdpi.com/1422-0067/24/23/16568<i>Penicillium sajarovii</i><i>Aspergillus protuberus</i><i>ITS</i><i>beta-tubulin</i><i>calmodulin</i><i>RPB2</i> |
| spellingShingle | Elena V. Leshchenko Dmitrii V. Berdyshev Ekaterina A. Yurchenko Alexandr S. Antonov Gleb V. Borkunov Natalya N. Kirichuk Viktoria E. Chausova Anatoly I. Kalinovskiy Roman S. Popov Yuliya V. Khudyakova Ekaterina A. Chingizova Artur R. Chingizov Marina P. Isaeva Anton N. Yurchenko Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 International Journal of Molecular Sciences <i>Penicillium sajarovii</i> <i>Aspergillus protuberus</i> <i>ITS</i> <i>beta-tubulin</i> <i>calmodulin</i> <i>RPB2</i> |
| title | Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 |
| title_full | Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 |
| title_fullStr | Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 |
| title_full_unstemmed | Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 |
| title_short | Bioactive Polyketides from the Natural Complex of the Sea Urchin-Associated Fungi <i>Penicillium sajarovii</i> KMM 4718 and <i>Aspergillus protuberus</i> KMM 4747 |
| title_sort | bioactive polyketides from the natural complex of the sea urchin associated fungi i penicillium sajarovii i kmm 4718 and i aspergillus protuberus i kmm 4747 |
| topic | <i>Penicillium sajarovii</i> <i>Aspergillus protuberus</i> <i>ITS</i> <i>beta-tubulin</i> <i>calmodulin</i> <i>RPB2</i> |
| url | https://www.mdpi.com/1422-0067/24/23/16568 |
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