Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp.
A chemical investigation of a methanol extract of <i>Spongia</i> sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids—scalimides A–L (<b>1</b>–<b>12</b>)—together with two previously described scalarin derivatives....
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-11-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/11/726 |
| _version_ | 1797464795981545472 |
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| author | A-Young Shin Hyi-Seung Lee Jihoon Lee |
| author_facet | A-Young Shin Hyi-Seung Lee Jihoon Lee |
| author_sort | A-Young Shin |
| collection | DOAJ |
| description | A chemical investigation of a methanol extract of <i>Spongia</i> sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids—scalimides A–L (<b>1</b>–<b>12</b>)—together with two previously described scalarin derivatives. The elucidation of the structure of the scalaranes based on the interpretation of their NMR and HRMS data revealed that <b>1</b>–<b>12</b> featured a <i>β</i>-alanine-substituted E-ring but differed from each other through variations in their oxidation states and substitutions occurring at C16, C24, and C25. Evaluation of the antimicrobial activity of <b>1</b>–<b>12</b> against several Gram-positive and Gram-negative bacteria showed that <b>10</b> and <b>11</b> were active against <i>Micrococcus luteus</i> and <i>Bacillus subtilis,</i> respectively, with MIC values ranging from 4 to 16 μg/mL. |
| first_indexed | 2024-03-09T18:13:14Z |
| format | Article |
| id | doaj.art-dce494e79c6f4cf2bdc64d3b48db5341 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T18:13:14Z |
| publishDate | 2022-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-dce494e79c6f4cf2bdc64d3b48db53412023-11-24T09:00:15ZengMDPI AGMarine Drugs1660-33972022-11-01201172610.3390/md20110726Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp.A-Young Shin0Hyi-Seung Lee1Jihoon Lee2Korea Institute of Ocean Science & Technology (KIOST), Busan 49111, Republic of KoreaKorea Institute of Ocean Science & Technology (KIOST), Busan 49111, Republic of KoreaKorea Institute of Ocean Science & Technology (KIOST), Busan 49111, Republic of KoreaA chemical investigation of a methanol extract of <i>Spongia</i> sp., a marine sponge collected from the Philippines, identified 12 unreported scalarane-type alkaloids—scalimides A–L (<b>1</b>–<b>12</b>)—together with two previously described scalarin derivatives. The elucidation of the structure of the scalaranes based on the interpretation of their NMR and HRMS data revealed that <b>1</b>–<b>12</b> featured a <i>β</i>-alanine-substituted E-ring but differed from each other through variations in their oxidation states and substitutions occurring at C16, C24, and C25. Evaluation of the antimicrobial activity of <b>1</b>–<b>12</b> against several Gram-positive and Gram-negative bacteria showed that <b>10</b> and <b>11</b> were active against <i>Micrococcus luteus</i> and <i>Bacillus subtilis,</i> respectively, with MIC values ranging from 4 to 16 μg/mL.https://www.mdpi.com/1660-3397/20/11/726scalarane sesterterpenescalimide<i>Spongia</i> sp.marine spongeantimicrobial activity |
| spellingShingle | A-Young Shin Hyi-Seung Lee Jihoon Lee Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. Marine Drugs scalarane sesterterpene scalimide <i>Spongia</i> sp. marine sponge antimicrobial activity |
| title | Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. |
| title_full | Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. |
| title_fullStr | Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. |
| title_full_unstemmed | Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. |
| title_short | Isolation of Scalimides A–L: <i>β</i>-Alanine-Bearing Scalarane Analogs from the Marine Sponge <i>Spongia</i> sp. |
| title_sort | isolation of scalimides a l i β i alanine bearing scalarane analogs from the marine sponge i spongia i sp |
| topic | scalarane sesterterpene scalimide <i>Spongia</i> sp. marine sponge antimicrobial activity |
| url | https://www.mdpi.com/1660-3397/20/11/726 |
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