New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078
As part of our continuing efforts to discover new bioactive compounds from microbial sources, a reinvestigation of extracts of scaled-up cultures of the marine-derived <i>Streptomyces</i> sp. strain CA-271078 resulted in the isolation and structural elucidation of four new napyradiomycin...
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2019-12-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/1/22 |
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| author | Daniel Carretero-Molina Francisco Javier Ortiz-López Jesús Martín Daniel Oves-Costales Caridad Díaz Mercedes de la Cruz Bastien Cautain Francisca Vicente Olga Genilloud Fernando Reyes |
| author_facet | Daniel Carretero-Molina Francisco Javier Ortiz-López Jesús Martín Daniel Oves-Costales Caridad Díaz Mercedes de la Cruz Bastien Cautain Francisca Vicente Olga Genilloud Fernando Reyes |
| author_sort | Daniel Carretero-Molina |
| collection | DOAJ |
| description | As part of our continuing efforts to discover new bioactive compounds from microbial sources, a reinvestigation of extracts of scaled-up cultures of the marine-derived <i>Streptomyces</i> sp. strain CA-271078 resulted in the isolation and structural elucidation of four new napyradiomycins (<b>1</b>−<b>3</b>, <b>5</b>). The known napyradiomycin SC (<b>4</b>), whose structural details had not been previously described in detail, and another ten related known compounds (<b>6</b>−<b>15</b>). The structures of the new napyradiomycins were characterized by HRMS and 1D- and 2D-NMR spectroscopies and their relative configurations were established through a combination of molecular modelling with <i>nOe</i> and coupling constants NMR analysis. The absolute configuration of each compound is also proposed based on biosynthetic arguments and the comparison of specific rotation data with those of related compounds. Among the new compounds, <b>1</b> was determined to be the first non-halogenated member of napyradiomycin A series containing a functionalized prenyl side chain, while <b>2</b>−<b>4</b> harbor in their structures the characteristic chloro-cyclohexane ring of the napyradiomycin B series. Remarkably, compound <b>5</b> displays an unprecedented 14-membered cyclic ether ring between the prenyl side chain and the chromophore, thus representing the first member of a new class of napyradiomycins that we have designated as napyradiomycin D1. Anti-infective and cytotoxic properties for all isolated compounds were evaluated against a set of pathogenic microorganisms and the HepG2 cell line, respectively. Among the new compounds, napyradiomycin D1 exhibited significant growth-inhibitory activity against methicillin-resistant <i>Staphylococcus aureus</i>, <i>Mycobacterium tuberculosis</i>, and HepG2. |
| first_indexed | 2024-04-11T18:25:36Z |
| format | Article |
| id | doaj.art-aabed86dd04e4745abb4d917123f8973 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-04-11T18:25:36Z |
| publishDate | 2019-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-aabed86dd04e4745abb4d917123f89732022-12-22T04:09:37ZengMDPI AGMarine Drugs1660-33972019-12-011812210.3390/md18010022md18010022New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078Daniel Carretero-Molina0Francisco Javier Ortiz-López1Jesús Martín2Daniel Oves-Costales3Caridad Díaz4Mercedes de la Cruz5Bastien Cautain6Francisca Vicente7Olga Genilloud8Fernando Reyes9Fundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainFundación MEDINA, Centro de Excelencia en Investigación de Medicamentos Innovadores en Andalucía, Avda. del Conocimiento 34, 18016 Armilla (Granada), SpainAs part of our continuing efforts to discover new bioactive compounds from microbial sources, a reinvestigation of extracts of scaled-up cultures of the marine-derived <i>Streptomyces</i> sp. strain CA-271078 resulted in the isolation and structural elucidation of four new napyradiomycins (<b>1</b>−<b>3</b>, <b>5</b>). The known napyradiomycin SC (<b>4</b>), whose structural details had not been previously described in detail, and another ten related known compounds (<b>6</b>−<b>15</b>). The structures of the new napyradiomycins were characterized by HRMS and 1D- and 2D-NMR spectroscopies and their relative configurations were established through a combination of molecular modelling with <i>nOe</i> and coupling constants NMR analysis. The absolute configuration of each compound is also proposed based on biosynthetic arguments and the comparison of specific rotation data with those of related compounds. Among the new compounds, <b>1</b> was determined to be the first non-halogenated member of napyradiomycin A series containing a functionalized prenyl side chain, while <b>2</b>−<b>4</b> harbor in their structures the characteristic chloro-cyclohexane ring of the napyradiomycin B series. Remarkably, compound <b>5</b> displays an unprecedented 14-membered cyclic ether ring between the prenyl side chain and the chromophore, thus representing the first member of a new class of napyradiomycins that we have designated as napyradiomycin D1. Anti-infective and cytotoxic properties for all isolated compounds were evaluated against a set of pathogenic microorganisms and the HepG2 cell line, respectively. Among the new compounds, napyradiomycin D1 exhibited significant growth-inhibitory activity against methicillin-resistant <i>Staphylococcus aureus</i>, <i>Mycobacterium tuberculosis</i>, and HepG2.https://www.mdpi.com/1660-3397/18/1/22napyradiomycinsmarine actinomycetesstructural elucidationantimicrobial activitycytotoxicity |
| spellingShingle | Daniel Carretero-Molina Francisco Javier Ortiz-López Jesús Martín Daniel Oves-Costales Caridad Díaz Mercedes de la Cruz Bastien Cautain Francisca Vicente Olga Genilloud Fernando Reyes New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 Marine Drugs napyradiomycins marine actinomycetes structural elucidation antimicrobial activity cytotoxicity |
| title | New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 |
| title_full | New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 |
| title_fullStr | New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 |
| title_full_unstemmed | New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 |
| title_short | New Napyradiomycin Analogues from <i>Streptomyces</i> sp. Strain CA-271078 |
| title_sort | new napyradiomycin analogues from i streptomyces i sp strain ca 271078 |
| topic | napyradiomycins marine actinomycetes structural elucidation antimicrobial activity cytotoxicity |
| url | https://www.mdpi.com/1660-3397/18/1/22 |
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