New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti
Abstract Two novel compounds including a cyclohelminthol type polyketide (namely oxaleimide K, 1) and a maleimide derivative (namely peniroquefortine A, 2), and a new natural product (namely 2-(acetylamino)-N-[(1E)-2-phenylethenyl]-acetamide, 3), together with four known compounds (4–7), were isolat...
| Main Authors: | , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
SpringerOpen
2023-06-01
|
| Series: | Natural Products and Bioprospecting |
| Subjects: | |
| Online Access: | https://doi.org/10.1007/s13659-023-00381-4 |
| _version_ | 1797811217813733376 |
|---|---|
| author | Shuyuan Mo Ziming Zhao Zi Ye Zhihong Huang Yaxin Zhang Wanqi Yang Jianping Wang Zhengxi Hu Yonghui Zhang |
| author_facet | Shuyuan Mo Ziming Zhao Zi Ye Zhihong Huang Yaxin Zhang Wanqi Yang Jianping Wang Zhengxi Hu Yonghui Zhang |
| author_sort | Shuyuan Mo |
| collection | DOAJ |
| description | Abstract Two novel compounds including a cyclohelminthol type polyketide (namely oxaleimide K, 1) and a maleimide derivative (namely peniroquefortine A, 2), and a new natural product (namely 2-(acetylamino)-N-[(1E)-2-phenylethenyl]-acetamide, 3), together with four known compounds (4–7), were isolated and identified from fungus Penicillium roqueforti, which was separated from the root soil of Hypericum beanii N. Robson collected from the Shennongjia Forestry District, Hubei Province. Their structures including absolute configurations were mainly established by the NMR spectroscopy analyses and single-crystal X-ray diffraction experiment. Compound 1 represents the second example of a cyclohelminthol type polyketide, which features a rare 6/6/5/5 tetracyclic system and a branched aliphatic chain containing a terminal olefin (oct-1-en-3-yl) moiety, and compound 2 possesses an unprecedented carbon skeleton that is uniquely defined by a maleimide moiety linked to the respective 4-methylene-2-(3-methylbut-2-en-1-yl)-phenol and para-substituted aromatic moieties via the carbon-carbon bonds. Remarkably, the absolute configuration of a cyclohelminthol type polyketide as exemplified by compound 1 is determined by the single-crystal diffraction analysis for the first time, highlighting an E-configuration for the linkage of a succinimide moiety and a tetrahydrofuran moiety for 1 rather than a Z-configuration as previously reported in the biosynthesis study, which gives a new insight into the structural elucidation of this category of polyketides. Additionally, compound 1 exhibited significant cytotoxic activity against multiple tumor cells, especially against the Farage and SU-DHL-2 cells (IC50 < 20 µM, 48 h). Further mechanism study revealed that compound 1 significantly induced cell cycle arrest in Farage and SU-DHL-2 cells by causing abnormal ROS level and triggering oxidative stress. Graphical Abstract |
| first_indexed | 2024-03-13T07:20:22Z |
| format | Article |
| id | doaj.art-a8a1c842fa5b41f395002b05b7a862ca |
| institution | Directory Open Access Journal |
| issn | 2192-2195 2192-2209 |
| language | English |
| last_indexed | 2024-03-13T07:20:22Z |
| publishDate | 2023-06-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Natural Products and Bioprospecting |
| spelling | doaj.art-a8a1c842fa5b41f395002b05b7a862ca2023-06-04T11:42:01ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092023-06-011311810.1007/s13659-023-00381-4New secondary metabolites with cytotoxicity from fungus Penicillium roquefortiShuyuan Mo0Ziming Zhao1Zi Ye2Zhihong Huang3Yaxin Zhang4Wanqi Yang5Jianping Wang6Zhengxi Hu7Yonghui Zhang8Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyHubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and TechnologyAbstract Two novel compounds including a cyclohelminthol type polyketide (namely oxaleimide K, 1) and a maleimide derivative (namely peniroquefortine A, 2), and a new natural product (namely 2-(acetylamino)-N-[(1E)-2-phenylethenyl]-acetamide, 3), together with four known compounds (4–7), were isolated and identified from fungus Penicillium roqueforti, which was separated from the root soil of Hypericum beanii N. Robson collected from the Shennongjia Forestry District, Hubei Province. Their structures including absolute configurations were mainly established by the NMR spectroscopy analyses and single-crystal X-ray diffraction experiment. Compound 1 represents the second example of a cyclohelminthol type polyketide, which features a rare 6/6/5/5 tetracyclic system and a branched aliphatic chain containing a terminal olefin (oct-1-en-3-yl) moiety, and compound 2 possesses an unprecedented carbon skeleton that is uniquely defined by a maleimide moiety linked to the respective 4-methylene-2-(3-methylbut-2-en-1-yl)-phenol and para-substituted aromatic moieties via the carbon-carbon bonds. Remarkably, the absolute configuration of a cyclohelminthol type polyketide as exemplified by compound 1 is determined by the single-crystal diffraction analysis for the first time, highlighting an E-configuration for the linkage of a succinimide moiety and a tetrahydrofuran moiety for 1 rather than a Z-configuration as previously reported in the biosynthesis study, which gives a new insight into the structural elucidation of this category of polyketides. Additionally, compound 1 exhibited significant cytotoxic activity against multiple tumor cells, especially against the Farage and SU-DHL-2 cells (IC50 < 20 µM, 48 h). Further mechanism study revealed that compound 1 significantly induced cell cycle arrest in Farage and SU-DHL-2 cells by causing abnormal ROS level and triggering oxidative stress. Graphical Abstracthttps://doi.org/10.1007/s13659-023-00381-4Hypericum beanii N. RobsonRoot soil-derived fungusPenicillium roquefortiStructural elucidationCytotoxicity |
| spellingShingle | Shuyuan Mo Ziming Zhao Zi Ye Zhihong Huang Yaxin Zhang Wanqi Yang Jianping Wang Zhengxi Hu Yonghui Zhang New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti Natural Products and Bioprospecting Hypericum beanii N. Robson Root soil-derived fungus Penicillium roqueforti Structural elucidation Cytotoxicity |
| title | New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti |
| title_full | New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti |
| title_fullStr | New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti |
| title_full_unstemmed | New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti |
| title_short | New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti |
| title_sort | new secondary metabolites with cytotoxicity from fungus penicillium roqueforti |
| topic | Hypericum beanii N. Robson Root soil-derived fungus Penicillium roqueforti Structural elucidation Cytotoxicity |
| url | https://doi.org/10.1007/s13659-023-00381-4 |
| work_keys_str_mv | AT shuyuanmo newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT zimingzhao newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT ziye newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT zhihonghuang newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT yaxinzhang newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT wanqiyang newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT jianpingwang newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT zhengxihu newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti AT yonghuizhang newsecondarymetaboliteswithcytotoxicityfromfunguspenicilliumroqueforti |