Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i>
Gracilioether M (<b>6</b>) and 11,12-dihydrogracilioether M (<b>7</b>), two polyketides with a [2(5H)-furanylidene]ethanoate moiety, along with known plakortone G (<b>9</b>) and its new naturally occurring derivative 9,10-dihydroplakortone G (<b>8</b>)...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-12-01
|
| Series: | Applied Sciences |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2076-3417/14/1/281 |
| _version_ | 1797359069118332928 |
|---|---|
| author | Luis A. Amador Abimael D. Rodríguez Lesly Carmona-Sarabia Emilee E. Colón-Lorenzo Adelfa E. Serrano |
| author_facet | Luis A. Amador Abimael D. Rodríguez Lesly Carmona-Sarabia Emilee E. Colón-Lorenzo Adelfa E. Serrano |
| author_sort | Luis A. Amador |
| collection | DOAJ |
| description | Gracilioether M (<b>6</b>) and 11,12-dihydrogracilioether M (<b>7</b>), two polyketides with a [2(5H)-furanylidene]ethanoate moiety, along with known plakortone G (<b>9</b>) and its new naturally occurring derivative 9,10-dihydroplakortone G (<b>8</b>), were isolated from the Caribbean marine sponge <i>Plakortis halichondrioides</i>. The structures and absolute configuration of <b>6</b>, <b>7</b>, and <b>8</b> were characterized by analysis of HRESIMS and NMR spectroscopic data, chemical derivatization, and side-by-side comparisons with published NMR data of related analogs. Compounds <b>6</b> and <b>7</b> and a mixture of <b>8</b> and <b>9</b> were evaluated for cytotoxicity against MCF-7 human breast cancer cells. In addition, the in vitro antiplasmodial activity against <i>Plasmodium berghei</i> of these compounds was scrutinized using a drug luminescence assay. |
| first_indexed | 2024-03-08T15:11:34Z |
| format | Article |
| id | doaj.art-50f2e052fbe84ec9b7a207a714a58c38 |
| institution | Directory Open Access Journal |
| issn | 2076-3417 |
| language | English |
| last_indexed | 2024-03-08T15:11:34Z |
| publishDate | 2023-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Applied Sciences |
| spelling | doaj.art-50f2e052fbe84ec9b7a207a714a58c382024-01-10T14:51:36ZengMDPI AGApplied Sciences2076-34172023-12-0114128110.3390/app14010281Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i>Luis A. Amador0Abimael D. Rodríguez1Lesly Carmona-Sarabia2Emilee E. Colón-Lorenzo3Adelfa E. Serrano4Molecular Sciences Research Center, University of Puerto Rico, 1390 Ponce de León Avenue, San Juan 00926, Puerto RicoMolecular Sciences Research Center, University of Puerto Rico, 1390 Ponce de León Avenue, San Juan 00926, Puerto RicoMolecular Sciences Research Center, University of Puerto Rico, 1390 Ponce de León Avenue, San Juan 00926, Puerto RicoDepartment of Microbiology and Medical Zoology, University of Puerto Rico School of Medicine, San Juan 00921, Puerto RicoDepartment of Microbiology and Medical Zoology, University of Puerto Rico School of Medicine, San Juan 00921, Puerto RicoGracilioether M (<b>6</b>) and 11,12-dihydrogracilioether M (<b>7</b>), two polyketides with a [2(5H)-furanylidene]ethanoate moiety, along with known plakortone G (<b>9</b>) and its new naturally occurring derivative 9,10-dihydroplakortone G (<b>8</b>), were isolated from the Caribbean marine sponge <i>Plakortis halichondrioides</i>. The structures and absolute configuration of <b>6</b>, <b>7</b>, and <b>8</b> were characterized by analysis of HRESIMS and NMR spectroscopic data, chemical derivatization, and side-by-side comparisons with published NMR data of related analogs. Compounds <b>6</b> and <b>7</b> and a mixture of <b>8</b> and <b>9</b> were evaluated for cytotoxicity against MCF-7 human breast cancer cells. In addition, the in vitro antiplasmodial activity against <i>Plasmodium berghei</i> of these compounds was scrutinized using a drug luminescence assay.https://www.mdpi.com/2076-3417/14/1/281<i>Plakortis halichondrioides</i>polyketidegracilioethermarine sponges |
| spellingShingle | Luis A. Amador Abimael D. Rodríguez Lesly Carmona-Sarabia Emilee E. Colón-Lorenzo Adelfa E. Serrano Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> Applied Sciences <i>Plakortis halichondrioides</i> polyketide gracilioether marine sponges |
| title | Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> |
| title_full | Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> |
| title_fullStr | Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> |
| title_full_unstemmed | Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> |
| title_short | Two Gracilioethers Containing a [2(5H)-Furanylidene]ethanoate Moiety and 9,10-Dihydroplakortone G: New Polyketides from the Caribbean Marine Sponge <i>Plakortis halichondrioides</i> |
| title_sort | two gracilioethers containing a 2 5h furanylidene ethanoate moiety and 9 10 dihydroplakortone g new polyketides from the caribbean marine sponge i plakortis halichondrioides i |
| topic | <i>Plakortis halichondrioides</i> polyketide gracilioether marine sponges |
| url | https://www.mdpi.com/2076-3417/14/1/281 |
| work_keys_str_mv | AT luisaamador twogracilioetherscontaininga25hfuranylideneethanoatemoietyand910dihydroplakortonegnewpolyketidesfromthecaribbeanmarinespongeiplakortishalichondrioidesi AT abimaeldrodriguez twogracilioetherscontaininga25hfuranylideneethanoatemoietyand910dihydroplakortonegnewpolyketidesfromthecaribbeanmarinespongeiplakortishalichondrioidesi AT leslycarmonasarabia twogracilioetherscontaininga25hfuranylideneethanoatemoietyand910dihydroplakortonegnewpolyketidesfromthecaribbeanmarinespongeiplakortishalichondrioidesi AT emileeecolonlorenzo twogracilioetherscontaininga25hfuranylideneethanoatemoietyand910dihydroplakortonegnewpolyketidesfromthecaribbeanmarinespongeiplakortishalichondrioidesi AT adelfaeserrano twogracilioetherscontaininga25hfuranylideneethanoatemoietyand910dihydroplakortonegnewpolyketidesfromthecaribbeanmarinespongeiplakortishalichondrioidesi |