Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula
Three new diterpene alkaloids, (+)-8-epiagelasine T (<b>1</b>), (+)-10-epiagelasine B (<b>2</b>), and (+)-12-hydroxyagelasidine C (<b>3</b>), along with three known compounds, (+)-<i>ent</i>-agelasine F (<b>4</b>), (+)-agelasine B (<b>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-04-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/5/298 |
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| author | Dawrin Pech-Puch Abel M. Forero Juan Carlos Fuentes-Monteverde Cristina Lasarte-Monterrubio Marta Martinez-Guitian Carlos González-Salas Sergio Guillén-Hernández Harold Villegas-Hernández Alejandro Beceiro Christian Griesinger Jaime Rodríguez Carlos Jiménez |
| author_facet | Dawrin Pech-Puch Abel M. Forero Juan Carlos Fuentes-Monteverde Cristina Lasarte-Monterrubio Marta Martinez-Guitian Carlos González-Salas Sergio Guillén-Hernández Harold Villegas-Hernández Alejandro Beceiro Christian Griesinger Jaime Rodríguez Carlos Jiménez |
| author_sort | Dawrin Pech-Puch |
| collection | DOAJ |
| description | Three new diterpene alkaloids, (+)-8-epiagelasine T (<b>1</b>), (+)-10-epiagelasine B (<b>2</b>), and (+)-12-hydroxyagelasidine C (<b>3</b>), along with three known compounds, (+)-<i>ent</i>-agelasine F (<b>4</b>), (+)-agelasine B (<b>5</b>), and (+)-agelasidine C (<b>6</b>), were isolated from the sponge <i>Agelas citrina</i>, collected on the coasts of the Yucatán Peninsula (Mexico). Their chemical structures were elucidated by 1D and 2D NMR spectroscopy, HRESIMS techniques, and a comparison with literature data. Although the synthesis of (+)-<i>ent</i>-agelasine F (<b>4</b>) has been previously reported, this is the first time that it was isolated as a natural product. The evaluation of the antimicrobial activity against the Gram-positive pathogens <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Enterococcus faecalis</i> showed that all of them were active, with (+)-10-epiagelasine B (<b>2</b>) being the most active compound with an MIC in the range of 1–8 µg/mL. On the other hand, the Gram-negative pathogenes <i>Acinetobacter baumannii</i>, <i>Pseudomonas aeruginosa</i>, and <i>Klebsiella pneumoniae</i> were also evaluated, and only (+)-agelasine B (<b>5</b>) showed a moderate antibacterial activity with a MIC value of 16 μg/mL. |
| first_indexed | 2024-03-10T03:31:57Z |
| format | Article |
| id | doaj.art-7eaa83cc356f4d17b5478926e3a1cff0 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T03:31:57Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-7eaa83cc356f4d17b5478926e3a1cff02023-11-23T11:54:10ZengMDPI AGMarine Drugs1660-33972022-04-0120529810.3390/md20050298Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán PeninsulaDawrin Pech-Puch0Abel M. Forero1Juan Carlos Fuentes-Monteverde2Cristina Lasarte-Monterrubio3Marta Martinez-Guitian4Carlos González-Salas5Sergio Guillén-Hernández6Harold Villegas-Hernández7Alejandro Beceiro8Christian Griesinger9Jaime Rodríguez10Carlos Jiménez11Departamento de Química, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade de A Coruña, 15071 A Coruña, SpainDepartamento de Química, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade de A Coruña, 15071 A Coruña, SpainDepartment of NMR Based Structural Biology, Max Planck Institute (MPI) for Multidisciplinary Sciences, Am Fassberg 11, 37077 Göttingen, GermanyMicrobiology Department of the University Hospital A Coruña (CHUAC), Institute of Biomedical Research of A Coruña (INIBIC), Centro de Investigación Biomédica en Red (CIBER) Infec., 15006 A Coruña, SpainMicrobiology Department of the University Hospital A Coruña (CHUAC), Institute of Biomedical Research of A Coruña (INIBIC), Centro de Investigación Biomédica en Red (CIBER) Infec., 15006 A Coruña, SpainDepartamento de Biología Marina, Universidad Autónoma de Yucatán, Km. 15.5, Carretera Mérida-Xmatkuil, A.P. 4-116 Itzimná, Merida C.P. 97100, Yucatán, MexicoDepartamento de Biología Marina, Universidad Autónoma de Yucatán, Km. 15.5, Carretera Mérida-Xmatkuil, A.P. 4-116 Itzimná, Merida C.P. 97100, Yucatán, MexicoDepartamento de Biología Marina, Universidad Autónoma de Yucatán, Km. 15.5, Carretera Mérida-Xmatkuil, A.P. 4-116 Itzimná, Merida C.P. 97100, Yucatán, MexicoMicrobiology Department of the University Hospital A Coruña (CHUAC), Institute of Biomedical Research of A Coruña (INIBIC), Centro de Investigación Biomédica en Red (CIBER) Infec., 15006 A Coruña, SpainDepartment of NMR Based Structural Biology, Max Planck Institute (MPI) for Multidisciplinary Sciences, Am Fassberg 11, 37077 Göttingen, GermanyDepartamento de Química, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade de A Coruña, 15071 A Coruña, SpainDepartamento de Química, Facultade de Ciencias e Centro de Investigacións Científicas Avanzadas (CICA), Universidade de A Coruña, 15071 A Coruña, SpainThree new diterpene alkaloids, (+)-8-epiagelasine T (<b>1</b>), (+)-10-epiagelasine B (<b>2</b>), and (+)-12-hydroxyagelasidine C (<b>3</b>), along with three known compounds, (+)-<i>ent</i>-agelasine F (<b>4</b>), (+)-agelasine B (<b>5</b>), and (+)-agelasidine C (<b>6</b>), were isolated from the sponge <i>Agelas citrina</i>, collected on the coasts of the Yucatán Peninsula (Mexico). Their chemical structures were elucidated by 1D and 2D NMR spectroscopy, HRESIMS techniques, and a comparison with literature data. Although the synthesis of (+)-<i>ent</i>-agelasine F (<b>4</b>) has been previously reported, this is the first time that it was isolated as a natural product. The evaluation of the antimicrobial activity against the Gram-positive pathogens <i>Staphylococcus aureus</i>, <i>Streptococcus pneumoniae</i>, <i>Enterococcus faecalis</i> showed that all of them were active, with (+)-10-epiagelasine B (<b>2</b>) being the most active compound with an MIC in the range of 1–8 µg/mL. On the other hand, the Gram-negative pathogenes <i>Acinetobacter baumannii</i>, <i>Pseudomonas aeruginosa</i>, and <i>Klebsiella pneumoniae</i> were also evaluated, and only (+)-agelasine B (<b>5</b>) showed a moderate antibacterial activity with a MIC value of 16 μg/mL.https://www.mdpi.com/1660-3397/20/5/298diterpene alkaloidsagelasinesagelasidinesmarine sponge<i>Agelas citrina</i>antibacterial |
| spellingShingle | Dawrin Pech-Puch Abel M. Forero Juan Carlos Fuentes-Monteverde Cristina Lasarte-Monterrubio Marta Martinez-Guitian Carlos González-Salas Sergio Guillén-Hernández Harold Villegas-Hernández Alejandro Beceiro Christian Griesinger Jaime Rodríguez Carlos Jiménez Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula Marine Drugs diterpene alkaloids agelasines agelasidines marine sponge <i>Agelas citrina</i> antibacterial |
| title | Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula |
| title_full | Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula |
| title_fullStr | Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula |
| title_full_unstemmed | Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula |
| title_short | Antimicrobial Diterpene Alkaloids from an <i>Agelas citrina</i> Sponge Collected in the Yucatán Peninsula |
| title_sort | antimicrobial diterpene alkaloids from an i agelas citrina i sponge collected in the yucatan peninsula |
| topic | diterpene alkaloids agelasines agelasidines marine sponge <i>Agelas citrina</i> antibacterial |
| url | https://www.mdpi.com/1660-3397/20/5/298 |
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