Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity
Eighteen scalarane sesterterpenoids (<b>1</b>–<b>18</b>), including eight new derivatives (<b>1</b>–<b>8</b>), were isolated from the sponge <i>Hyrtios erectus</i> (family Thorectidae), the extract of which showed cytotoxicity against the H...
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| Format: | Article |
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MDPI AG
2022-09-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/20/10/604 |
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| author | Huynh Nguyen Khanh Tran Min Jin Kim Yeon-Ju Lee |
| author_facet | Huynh Nguyen Khanh Tran Min Jin Kim Yeon-Ju Lee |
| author_sort | Huynh Nguyen Khanh Tran |
| collection | DOAJ |
| description | Eighteen scalarane sesterterpenoids (<b>1</b>–<b>18</b>), including eight new derivatives (<b>1</b>–<b>8</b>), were isolated from the sponge <i>Hyrtios erectus</i> (family Thorectidae), the extract of which showed cytotoxicity against the HeLa and MCF-7 cell lines. Of the new derivatives, six compounds (<b>1</b>–<b>6</b>) were found to contain a γ-hydroxybutenolide moiety capable of reversible stereoinversion at the hydroxylated carbon center. Under the influence of other adjacent functional groups, each derivative exhibited a different stereochemical behavior, which was fully deduced by ROESY experiments. All the isolated compounds were examined for their cytotoxicity by MTS assay using staurosporine as a positive control (IC<sub>50</sub> 0.18 and 0.13 μΜ against HeLa and MCF-7 cells, respectively), and they were found to show weak growth inhibitory activities against HeLa and MCF-7 cells, with a minimal IC<sub>50</sub> value of 20.0 μΜ. The compounds containing a γ-hydroxybutenolide moiety (<b>1</b>–<b>3</b>, <b>10</b>, <b>12</b>) showed cytotoxicity, with IC<sub>50</sub> values ranging from 24.3 to 29.9 μΜ, and the most potent derivative was heteronemin (<b>16</b>). Although the cytotoxicities of isolated compounds were insufficient to discuss the structure–activity relationship, this research could contribute to expanding the structural diversity of scalaranes and understanding the stereochemical behavior of γ-hydroxybutenolides. |
| first_indexed | 2024-03-09T09:45:43Z |
| format | Article |
| id | doaj.art-57efa173f71f47d1b1904a99aa3b75f5 |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-09T09:45:43Z |
| publishDate | 2022-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-57efa173f71f47d1b1904a99aa3b75f52023-12-02T00:36:18ZengMDPI AGMarine Drugs1660-33972022-09-01201060410.3390/md20100604Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their CytotoxicityHuynh Nguyen Khanh Tran0Min Jin Kim1Yeon-Ju Lee2Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyangro, Busan 49111, KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyangro, Busan 49111, KoreaMarine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyangro, Busan 49111, KoreaEighteen scalarane sesterterpenoids (<b>1</b>–<b>18</b>), including eight new derivatives (<b>1</b>–<b>8</b>), were isolated from the sponge <i>Hyrtios erectus</i> (family Thorectidae), the extract of which showed cytotoxicity against the HeLa and MCF-7 cell lines. Of the new derivatives, six compounds (<b>1</b>–<b>6</b>) were found to contain a γ-hydroxybutenolide moiety capable of reversible stereoinversion at the hydroxylated carbon center. Under the influence of other adjacent functional groups, each derivative exhibited a different stereochemical behavior, which was fully deduced by ROESY experiments. All the isolated compounds were examined for their cytotoxicity by MTS assay using staurosporine as a positive control (IC<sub>50</sub> 0.18 and 0.13 μΜ against HeLa and MCF-7 cells, respectively), and they were found to show weak growth inhibitory activities against HeLa and MCF-7 cells, with a minimal IC<sub>50</sub> value of 20.0 μΜ. The compounds containing a γ-hydroxybutenolide moiety (<b>1</b>–<b>3</b>, <b>10</b>, <b>12</b>) showed cytotoxicity, with IC<sub>50</sub> values ranging from 24.3 to 29.9 μΜ, and the most potent derivative was heteronemin (<b>16</b>). Although the cytotoxicities of isolated compounds were insufficient to discuss the structure–activity relationship, this research could contribute to expanding the structural diversity of scalaranes and understanding the stereochemical behavior of γ-hydroxybutenolides.https://www.mdpi.com/1660-3397/20/10/604sponge<i>Thorectidae</i><i>Hyrtios erectus</i>sesterterpenescalaraneγ-hydroxybutenolide |
| spellingShingle | Huynh Nguyen Khanh Tran Min Jin Kim Yeon-Ju Lee Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity Marine Drugs sponge <i>Thorectidae</i> <i>Hyrtios erectus</i> sesterterpene scalarane γ-hydroxybutenolide |
| title | Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity |
| title_full | Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity |
| title_fullStr | Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity |
| title_full_unstemmed | Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity |
| title_short | Scalarane Sesterterpenoids Isolated from the Marine Sponge <i>Hyrtios erectus</i> and their Cytotoxicity |
| title_sort | scalarane sesterterpenoids isolated from the marine sponge i hyrtios erectus i and their cytotoxicity |
| topic | sponge <i>Thorectidae</i> <i>Hyrtios erectus</i> sesterterpene scalarane γ-hydroxybutenolide |
| url | https://www.mdpi.com/1660-3397/20/10/604 |
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