Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18
Eight new cytochalasins <b>1</b>–<b>8</b> and ten known analogs <b>9</b>–<b>18</b> were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds <b&g...
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MDPI AG
2021-10-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/21/6505 |
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| author | Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu |
| author_facet | Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu |
| author_sort | Guichon Huang |
| collection | DOAJ |
| description | Eight new cytochalasins <b>1</b>–<b>8</b> and ten known analogs <b>9</b>–<b>18</b> were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds <b>1</b>, <b>2</b>, <b>9</b> and <b>10</b> were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds <b>3</b> and <b>4</b> had conjugated diene structures in the macrocycle; and compound <b>6</b> had a β,γ-unsaturated ketone. The absolute configuration of 6 was confirmed for the first time by the octant rule. The acid-free purification process proved that the pentacyclic system was a natural biosynthetic product and not an acid-mediated intramolecular cyclized artifact. The new compounds did not exhibit activities against human cancer cell lines in cytotoxicity bioassays or antipathogenic fungal activity, but compounds <b>1</b>, <b>3</b> and <b>4</b> showed moderate antibacterial activity in disk diffusion assays. |
| first_indexed | 2024-03-10T05:56:10Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:56:10Z |
| publishDate | 2021-10-01 |
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| series | Molecules |
| spelling | doaj.art-c42dc5aaf08448b287a887722217fa0d2023-11-22T21:22:20ZengMDPI AGMolecules1420-30492021-10-012621650510.3390/molecules26216505Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18Guichon Huang0Weiwen Lin1Hanpeng Li2Qian Tang3Zhiyu Hu4Huiying Huang5Xianming Deng6Qingyan Xu7State Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaState Key Laboratory of Cellular Stress Biology, School of Life Sciences, Xiamen University, Xiamen 361102, ChinaEight new cytochalasins <b>1</b>–<b>8</b> and ten known analogs <b>9</b>–<b>18</b> were isolated from the endophytic fungus Phomopsis sp. xz-18. The planar structures of the cytochalasins were determined by HR-ESI-MS and NMR analysis. Compounds <b>1</b>, <b>2</b>, <b>9</b> and <b>10</b> were 5/6/6/7/5-fused pentacyclic cytochalasins; compounds <b>3</b> and <b>4</b> had conjugated diene structures in the macrocycle; and compound <b>6</b> had a β,γ-unsaturated ketone. The absolute configuration of 6 was confirmed for the first time by the octant rule. The acid-free purification process proved that the pentacyclic system was a natural biosynthetic product and not an acid-mediated intramolecular cyclized artifact. The new compounds did not exhibit activities against human cancer cell lines in cytotoxicity bioassays or antipathogenic fungal activity, but compounds <b>1</b>, <b>3</b> and <b>4</b> showed moderate antibacterial activity in disk diffusion assays.https://www.mdpi.com/1420-3049/26/21/6505cytochalasinspentacyclic systemoctant ruleantibacterial activity |
| spellingShingle | Guichon Huang Weiwen Lin Hanpeng Li Qian Tang Zhiyu Hu Huiying Huang Xianming Deng Qingyan Xu Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 Molecules cytochalasins pentacyclic system octant rule antibacterial activity |
| title | Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 |
| title_full | Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 |
| title_fullStr | Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 |
| title_full_unstemmed | Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 |
| title_short | Pentacyclic Cytochalasins and Their Derivatives from the Endophytic Fungus <i>Phomopsis</i> sp. xz-18 |
| title_sort | pentacyclic cytochalasins and their derivatives from the endophytic fungus i phomopsis i sp xz 18 |
| topic | cytochalasins pentacyclic system octant rule antibacterial activity |
| url | https://www.mdpi.com/1420-3049/26/21/6505 |
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