New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp.
Continuing chemical investigation of the Red Sea sponge <i>Spongia</i> sp. led to the isolation of four new 3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactones, secodinorspongins A−D (<b>1</b>−<b>4</b>), along with a classical spongian diterpenoid...
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MDPI AG
2023-01-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/24/2/1252 |
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| author | Chi-Jen Tai Chih-Hua Chao Atallah F. Ahmed Chia-Hung Yen Tsong-Long Hwang Fang-Rong Chang Yusheng M. Huang Jyh-Horng Sheu |
| author_facet | Chi-Jen Tai Chih-Hua Chao Atallah F. Ahmed Chia-Hung Yen Tsong-Long Hwang Fang-Rong Chang Yusheng M. Huang Jyh-Horng Sheu |
| author_sort | Chi-Jen Tai |
| collection | DOAJ |
| description | Continuing chemical investigation of the Red Sea sponge <i>Spongia</i> sp. led to the isolation of four new 3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactones, secodinorspongins A−D (<b>1</b>−<b>4</b>), along with a classical spongian diterpenoid lactone, sponginolide (<b>5</b>). The chemical structures, including the absolute configurations of these compounds, were elucidated using the extensive spectroscopic study composed of 1D and 2D NMR data analyses, and a comparison between calculated-electronic-circular-dichroism (ECD) and experimental-circular-dichroism (CD) spectra. A plausible biosynthetic pathway of <b>1</b>−<b>4</b> was also proposed. Furthermore, the cytotoxicity, antibacterial and anti-inflammatory activities of <b>1</b>−<b>5</b> were evaluated. Compound <b>1</b> was found to exhibit inhibitory activity against the growth of <i>Staphylococcus aureus</i> (<i>S. aureus</i>), and <b>4</b> and <b>5</b> exhibited suppression of superoxide-anion generation and elastase release in fMLF/CB-induced human neutrophils. |
| first_indexed | 2024-03-09T12:24:01Z |
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| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-09T12:24:01Z |
| publishDate | 2023-01-01 |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-af44a4c5ef5f44b89e1f5214be07106f2023-11-30T22:37:37ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672023-01-01242125210.3390/ijms24021252New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp.Chi-Jen Tai0Chih-Hua Chao1Atallah F. Ahmed2Chia-Hung Yen3Tsong-Long Hwang4Fang-Rong Chang5Yusheng M. Huang6Jyh-Horng Sheu7Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, TaiwanSchool of Pharmacy, China Medical University, Taichung 40604, TaiwanDepartment of Pharmacognosy, College of Pharmacy, King Saud University, Riyadh 11451, Saudi ArabiaGraduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, TaiwanGraduate Institute of Natural Products, College of Medicine, Chang Gung University, Taoyuan 333, TaiwanGraduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 80708, TaiwanDepartment of Marine Recreation, National Penghu University of Science and Technology, Magong 88046, TaiwanDepartment of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung 80424, TaiwanContinuing chemical investigation of the Red Sea sponge <i>Spongia</i> sp. led to the isolation of four new 3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactones, secodinorspongins A−D (<b>1</b>−<b>4</b>), along with a classical spongian diterpenoid lactone, sponginolide (<b>5</b>). The chemical structures, including the absolute configurations of these compounds, were elucidated using the extensive spectroscopic study composed of 1D and 2D NMR data analyses, and a comparison between calculated-electronic-circular-dichroism (ECD) and experimental-circular-dichroism (CD) spectra. A plausible biosynthetic pathway of <b>1</b>−<b>4</b> was also proposed. Furthermore, the cytotoxicity, antibacterial and anti-inflammatory activities of <b>1</b>−<b>5</b> were evaluated. Compound <b>1</b> was found to exhibit inhibitory activity against the growth of <i>Staphylococcus aureus</i> (<i>S. aureus</i>), and <b>4</b> and <b>5</b> exhibited suppression of superoxide-anion generation and elastase release in fMLF/CB-induced human neutrophils.https://www.mdpi.com/1422-0067/24/2/1252Red Sea sponge<i>Spongia</i> sp.3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactonesspongian diterpenesecodinorspongins A−Dantibacterial assay |
| spellingShingle | Chi-Jen Tai Chih-Hua Chao Atallah F. Ahmed Chia-Hung Yen Tsong-Long Hwang Fang-Rong Chang Yusheng M. Huang Jyh-Horng Sheu New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. International Journal of Molecular Sciences Red Sea sponge <i>Spongia</i> sp. 3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactones spongian diterpene secodinorspongins A−D antibacterial assay |
| title | New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. |
| title_full | New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. |
| title_fullStr | New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. |
| title_full_unstemmed | New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. |
| title_short | New 3,4-<i>seco</i>-3,19-Dinor- and Spongian-Based Diterpenoid Lactones from the Marine Sponge <i>Spongia</i> sp. |
| title_sort | new 3 4 i seco i 3 19 dinor and spongian based diterpenoid lactones from the marine sponge i spongia i sp |
| topic | Red Sea sponge <i>Spongia</i> sp. 3,4-<i>seco</i>-3,19-dinorspongian diterpenoid lactones spongian diterpene secodinorspongins A−D antibacterial assay |
| url | https://www.mdpi.com/1422-0067/24/2/1252 |
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