Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i>
The chemical investigation of the culture filtrate of endophyte <i>Alternaria</i> sp. W-1 associated with <i>Laminaria japonica</i> provided a new tricycloalternarene compound, 2H-(2<i>E</i>)-tricycloalternarene 12a (<b>1</b>), together with five known...
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MDPI AG
2018-10-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/16/11/402 |
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| author | Li Shen Shu-Juan Tian Hui-Liang Song Xi Chen Hao Guo Dan Wan Yu-Rou Wang Feng-Wu Wang Li-Jun Liu |
| author_facet | Li Shen Shu-Juan Tian Hui-Liang Song Xi Chen Hao Guo Dan Wan Yu-Rou Wang Feng-Wu Wang Li-Jun Liu |
| author_sort | Li Shen |
| collection | DOAJ |
| description | The chemical investigation of the culture filtrate of endophyte <i>Alternaria</i> sp. W-1 associated with <i>Laminaria japonica</i> provided a new tricycloalternarene compound, 2H-(2<i>E</i>)-tricycloalternarene 12a (<b>1</b>), together with five known analogs: (2<i>E</i>)-tricycloalternarene 12a (<b>2</b>), tricycloalternarene 3a (<b>3</b>), tricycloalternarene F (<b>4</b>), 15-hydroxyl tricycloalternarene 5b (<b>5</b>), and ACTG-Toxin D (<b>6</b>). In vitro cytotoxicity against the human hepatocellular carcinoma cell line SMMC-7721 and the human gastric carcinoma cell line SGC-7901 was evaluated by the MTT method. Compounds <b>1</b>, <b>3</b>, and <b>4</b> inhibited the growth of SMMC-7721 cells with IC<sub>50</sub> values of 49.7 ± 1.1, 45.8 ± 4.6, and 80.3 ± 3.8 μg/mL, respectively, while the IC<sub>50</sub> value of the positive control cisplatin was 6.5 ± 0.5 μg/mL. Compounds <b>3</b> and <b>6</b> also showed moderate anti-proliferation activity against SGC-7901 cells with IC<sub>50</sub> values of 53.2 ± 2.9 and 35.1 ± 0.8 μg/mL, respectively, while the IC<sub>50</sub> value of cisplatin was 4.5 ± 0.6 μg/mL. Further studies revealed that the in vitro anticancer activity of compound <b>3</b> to SMMC-7721 cells was related to G1 phase cell cycle arrest and cell apoptosis, and the induced apoptosis was involved in both the mitochondrial pathway and the death receptor pathway. This is the first report on the anticancer mechanism of tricycloalternarene compounds. |
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| spelling | doaj.art-2d633b7229d649a18d93f00e7894cda72022-12-22T02:55:24ZengMDPI AGMarine Drugs1660-33972018-10-01161140210.3390/md16110402md16110402Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i>Li Shen0Shu-Juan Tian1Hui-Liang Song2Xi Chen3Hao Guo4Dan Wan5Yu-Rou Wang6Feng-Wu Wang7Li-Jun Liu8Institute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaCollege of Food Science and Engineering, Qingdao Agricultural University, Qingdao 266109, ChinaInstitute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaInstitute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaInstitute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaInstitute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaInstitute of Translational Medicine, Medical College, Yangzhou University, Yangzhou 225001, ChinaCollege of Food Science and Engineering, Qingdao Agricultural University, Qingdao 266109, ChinaJiangsu Co-Innovation Center for Modern Production Technology of Grain Crops/Jiangsu Key Laboratory of Crop Genetics and Physiology, Yangzhou University, Yangzhou 225009, ChinaThe chemical investigation of the culture filtrate of endophyte <i>Alternaria</i> sp. W-1 associated with <i>Laminaria japonica</i> provided a new tricycloalternarene compound, 2H-(2<i>E</i>)-tricycloalternarene 12a (<b>1</b>), together with five known analogs: (2<i>E</i>)-tricycloalternarene 12a (<b>2</b>), tricycloalternarene 3a (<b>3</b>), tricycloalternarene F (<b>4</b>), 15-hydroxyl tricycloalternarene 5b (<b>5</b>), and ACTG-Toxin D (<b>6</b>). In vitro cytotoxicity against the human hepatocellular carcinoma cell line SMMC-7721 and the human gastric carcinoma cell line SGC-7901 was evaluated by the MTT method. Compounds <b>1</b>, <b>3</b>, and <b>4</b> inhibited the growth of SMMC-7721 cells with IC<sub>50</sub> values of 49.7 ± 1.1, 45.8 ± 4.6, and 80.3 ± 3.8 μg/mL, respectively, while the IC<sub>50</sub> value of the positive control cisplatin was 6.5 ± 0.5 μg/mL. Compounds <b>3</b> and <b>6</b> also showed moderate anti-proliferation activity against SGC-7901 cells with IC<sub>50</sub> values of 53.2 ± 2.9 and 35.1 ± 0.8 μg/mL, respectively, while the IC<sub>50</sub> value of cisplatin was 4.5 ± 0.6 μg/mL. Further studies revealed that the in vitro anticancer activity of compound <b>3</b> to SMMC-7721 cells was related to G1 phase cell cycle arrest and cell apoptosis, and the induced apoptosis was involved in both the mitochondrial pathway and the death receptor pathway. This is the first report on the anticancer mechanism of tricycloalternarene compounds.https://www.mdpi.com/1660-3397/16/11/402<i>Laminaria japonica</i>endophyte<i>Alternaria</i> sp.tricycloalternarene compoundcytotoxicity |
| spellingShingle | Li Shen Shu-Juan Tian Hui-Liang Song Xi Chen Hao Guo Dan Wan Yu-Rou Wang Feng-Wu Wang Li-Jun Liu Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> Marine Drugs <i>Laminaria japonica</i> endophyte <i>Alternaria</i> sp. tricycloalternarene compound cytotoxicity |
| title | Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> |
| title_full | Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> |
| title_fullStr | Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> |
| title_full_unstemmed | Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> |
| title_short | Cytotoxic Tricycloalternarene Compounds from Endophyte <i>Alternaria</i> sp. W-1 Associated with <i>Laminaria japonica</i> |
| title_sort | cytotoxic tricycloalternarene compounds from endophyte i alternaria i sp w 1 associated with i laminaria japonica i |
| topic | <i>Laminaria japonica</i> endophyte <i>Alternaria</i> sp. tricycloalternarene compound cytotoxicity |
| url | https://www.mdpi.com/1660-3397/16/11/402 |
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