Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities
Two new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4<i>a</i>-hydroxy-chatancin (<b>1</b>) and sarcotoroid (<b>2</b>), together with two known related ones (<b>3</b> and <b>4</b>), were isolated from th...
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2024-12-01
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| author | Min Sun Songwei Li Jianang Zeng Yuewei Guo Changyun Wang Mingzhi Su |
| author_facet | Min Sun Songwei Li Jianang Zeng Yuewei Guo Changyun Wang Mingzhi Su |
| author_sort | Min Sun |
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| description | Two new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4<i>a</i>-hydroxy-chatancin (<b>1</b>) and sarcotoroid (<b>2</b>), together with two known related ones (<b>3</b> and <b>4</b>), were isolated from the soft coral <i>Sarcophyton tortuosum</i> collected off Ximao Island in the South China Sea. The structures of the new compounds were elucidated by extensive spectroscopic analysis, a quantum mechanical nuclear magnetic resonance (QM-NMR) method, a time-dependent density functional theory electronic circular dichroism (TDDFT-ECD) calculation, X-ray diffraction analysis, and comparison with the reported data in the literature. A plausible biosynthetic pathway of compounds <b>1</b>–<b>4</b> was proposed, involving undergoing a transannular Diels–Alder cycloaddition. In the bioassay, the new compound <b>1</b> displayed significant inhibitory activities against the fish pathogens <i>Streptococcus parauberis</i> KSP28, oxytetracycline-resistant <i>Streptococcus parauberis</i> SPOF3K, and <i>Photobacterium damselae</i> FP2244, with MIC values of 9.1, 9.1, and 18.2 μg/mL, respectively. Furthermore, by conducting a luciferase reporter assay on rat liver Ac2F cells, compounds <b>1</b>, <b>3</b>, and <b>4</b> were evaluated for peroxisome proliferator-activated receptor (PPAR) transcriptional activity, and compound <b>3</b> showed selective PPAR-β agonist activity at a concentration of 10 μΜ. |
| format | Article |
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| language | English |
| publishDate | 2024-12-01 |
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| series | Marine Drugs |
| spelling | doaj-art-c33f4dc0436d431eb22d3a6e12bec0722025-08-20T02:57:02ZengMDPI AGMarine Drugs1660-33972024-12-01221255310.3390/md22120553Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist ActivitiesMin Sun0Songwei Li1Jianang Zeng2Yuewei Guo3Changyun Wang4Mingzhi Su5MOE Key Laboratory of Marine Drugs and Key Laboratory of Evolution and Marine Biodiversity, Institute of Evolution & Marine Biodiversity, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaSchool of Medicine, Shanghai University, Shanghai 200444, ChinaShandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, ChinaShandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, ChinaMOE Key Laboratory of Marine Drugs and Key Laboratory of Evolution and Marine Biodiversity, Institute of Evolution & Marine Biodiversity, School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, ChinaShandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, ChinaTwo new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4<i>a</i>-hydroxy-chatancin (<b>1</b>) and sarcotoroid (<b>2</b>), together with two known related ones (<b>3</b> and <b>4</b>), were isolated from the soft coral <i>Sarcophyton tortuosum</i> collected off Ximao Island in the South China Sea. The structures of the new compounds were elucidated by extensive spectroscopic analysis, a quantum mechanical nuclear magnetic resonance (QM-NMR) method, a time-dependent density functional theory electronic circular dichroism (TDDFT-ECD) calculation, X-ray diffraction analysis, and comparison with the reported data in the literature. A plausible biosynthetic pathway of compounds <b>1</b>–<b>4</b> was proposed, involving undergoing a transannular Diels–Alder cycloaddition. In the bioassay, the new compound <b>1</b> displayed significant inhibitory activities against the fish pathogens <i>Streptococcus parauberis</i> KSP28, oxytetracycline-resistant <i>Streptococcus parauberis</i> SPOF3K, and <i>Photobacterium damselae</i> FP2244, with MIC values of 9.1, 9.1, and 18.2 μg/mL, respectively. Furthermore, by conducting a luciferase reporter assay on rat liver Ac2F cells, compounds <b>1</b>, <b>3</b>, and <b>4</b> were evaluated for peroxisome proliferator-activated receptor (PPAR) transcriptional activity, and compound <b>3</b> showed selective PPAR-β agonist activity at a concentration of 10 μΜ.https://www.mdpi.com/1660-3397/22/12/553soft coral<i>Sarcophyton tortuosum</i>polycyclic diterpenestransannular Diels–Alder cycloadditionantibacterial activityPPAR-β agonist activity |
| spellingShingle | Min Sun Songwei Li Jianang Zeng Yuewei Guo Changyun Wang Mingzhi Su Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities Marine Drugs soft coral <i>Sarcophyton tortuosum</i> polycyclic diterpenes transannular Diels–Alder cycloaddition antibacterial activity PPAR-β agonist activity |
| title | Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities |
| title_full | Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities |
| title_fullStr | Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities |
| title_full_unstemmed | Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities |
| title_short | Two New Diterpenoids Formed by Transannular Diels–Alder Cycloaddition from the Soft Coral <i>Sarcophyton tortuosum</i>, and Their Antibacterial and PPAR-β Agonist Activities |
| title_sort | two new diterpenoids formed by transannular diels alder cycloaddition from the soft coral i sarcophyton tortuosum i and their antibacterial and ppar β agonist activities |
| topic | soft coral <i>Sarcophyton tortuosum</i> polycyclic diterpenes transannular Diels–Alder cycloaddition antibacterial activity PPAR-β agonist activity |
| url | https://www.mdpi.com/1660-3397/22/12/553 |
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