Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor
The demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications. However, there remain many challenges that need to be addressed in order to make dinoflagellate bioactives a commercial reality. In this article, we...
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MDPI AG
2021-07-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/19/8/432 |
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| author | Adrián Morales-Amador Alejandro Molina-Miras Lorenzo López-Rosales Asterio Sánchez-Mirón Francisco García-Camacho María L. Souto José J. Fernández |
| author_facet | Adrián Morales-Amador Alejandro Molina-Miras Lorenzo López-Rosales Asterio Sánchez-Mirón Francisco García-Camacho María L. Souto José J. Fernández |
| author_sort | Adrián Morales-Amador |
| collection | DOAJ |
| description | The demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications. However, there remain many challenges that need to be addressed in order to make dinoflagellate bioactives a commercial reality. In this article, we describe the technical feasibility of producing and recovering amphidinol analogues (AMs) excreted into a culture broth of <i>Amphidinium carterae</i> ACRN03, successfully cultured in an LED-illuminated pilot-scale (80 L) bubble column photobioreactor operated in fed-batch mode with a pulse feeding strategy. We report on the isolation of new structurally related AMs, amphidinol 24 (<b>1</b>, AM24), amphidinol 25 (<b>2</b>, AM25) and amphidinol 26 (<b>3</b>, AM26), from a singular fraction resulting from the downstream processing. Their planar structures were elucidated by extensive NMR and HRMS analysis, whereas the relative configuration of the C-32→C-47 bis-tetrahydropyran core was confirmed to be antipodal in accord with the recently revised configuration of AM3. The hemolytic activities of the new metabolites and other related derivatives were evaluated, and structure–activity conclusions were established. Their isolation was based on a straightforward and high-performance bioprocess that could be suitable for the commercial development of AMs or other high-value compounds from shear sensitive dinoflagellates. |
| first_indexed | 2024-03-10T08:39:24Z |
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| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T08:39:24Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-c03923716c954de192ccabc2979fa5562023-11-22T08:25:35ZengMDPI AGMarine Drugs1660-33972021-07-0119843210.3390/md19080432Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale PhotobioreactorAdrián Morales-Amador0Alejandro Molina-Miras1Lorenzo López-Rosales2Asterio Sánchez-Mirón3Francisco García-Camacho4María L. Souto5José J. Fernández6Instituto Universitario de Bio-Orgánica Antonio González (IUBO AG), Universidad de La Laguna (ULL), Avda. Astrofísico F. Sánchez 2, 38206 La Laguna, SpainChemical Engineering Department, University of Almería, 04120 Almería, SpainChemical Engineering Department, University of Almería, 04120 Almería, SpainChemical Engineering Department, University of Almería, 04120 Almería, SpainChemical Engineering Department, University of Almería, 04120 Almería, SpainInstituto Universitario de Bio-Orgánica Antonio González (IUBO AG), Universidad de La Laguna (ULL), Avda. Astrofísico F. Sánchez 2, 38206 La Laguna, SpainInstituto Universitario de Bio-Orgánica Antonio González (IUBO AG), Universidad de La Laguna (ULL), Avda. Astrofísico F. Sánchez 2, 38206 La Laguna, SpainThe demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications. However, there remain many challenges that need to be addressed in order to make dinoflagellate bioactives a commercial reality. In this article, we describe the technical feasibility of producing and recovering amphidinol analogues (AMs) excreted into a culture broth of <i>Amphidinium carterae</i> ACRN03, successfully cultured in an LED-illuminated pilot-scale (80 L) bubble column photobioreactor operated in fed-batch mode with a pulse feeding strategy. We report on the isolation of new structurally related AMs, amphidinol 24 (<b>1</b>, AM24), amphidinol 25 (<b>2</b>, AM25) and amphidinol 26 (<b>3</b>, AM26), from a singular fraction resulting from the downstream processing. Their planar structures were elucidated by extensive NMR and HRMS analysis, whereas the relative configuration of the C-32→C-47 bis-tetrahydropyran core was confirmed to be antipodal in accord with the recently revised configuration of AM3. The hemolytic activities of the new metabolites and other related derivatives were evaluated, and structure–activity conclusions were established. Their isolation was based on a straightforward and high-performance bioprocess that could be suitable for the commercial development of AMs or other high-value compounds from shear sensitive dinoflagellates.https://www.mdpi.com/1660-3397/19/8/432amphidinol<i>Amphidinium carterae</i>dinoflagellate microalgaephotobioreactorhemolysis |
| spellingShingle | Adrián Morales-Amador Alejandro Molina-Miras Lorenzo López-Rosales Asterio Sánchez-Mirón Francisco García-Camacho María L. Souto José J. Fernández Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor Marine Drugs amphidinol <i>Amphidinium carterae</i> dinoflagellate microalgae photobioreactor hemolysis |
| title | Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor |
| title_full | Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor |
| title_fullStr | Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor |
| title_full_unstemmed | Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor |
| title_short | Isolation and Structural Elucidation of New Amphidinol Analogues from <i>Amphidinium carterae</i> Cultivated in a Pilot-Scale Photobioreactor |
| title_sort | isolation and structural elucidation of new amphidinol analogues from i amphidinium carterae i cultivated in a pilot scale photobioreactor |
| topic | amphidinol <i>Amphidinium carterae</i> dinoflagellate microalgae photobioreactor hemolysis |
| url | https://www.mdpi.com/1660-3397/19/8/432 |
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