Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5
Abstract Two novel koninginin derivatives, koningipyridines A and B (1 and 2), along with four known compounds (3˗6) were isolated from the EtOAc extract of the endophytic fungus Trichoderma koningiopsis SC-5. Among them, koningipyridine A featured an unprecedented pentacyclic ketal skeleton with th...
| Main Authors: | , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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SpringerOpen
2024-01-01
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| Series: | Natural Products and Bioprospecting |
| Subjects: | |
| Online Access: | https://doi.org/10.1007/s13659-024-00429-z |
| _version_ | 1797355442545885184 |
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| author | Weiwei Peng Qi Huang Xin Ke Wenxuan Wang Yan Chen Zihuan Sang Chen Chen Siyu Qin Yuting Zheng Haibo Tan Zhenxing Zou |
| author_facet | Weiwei Peng Qi Huang Xin Ke Wenxuan Wang Yan Chen Zihuan Sang Chen Chen Siyu Qin Yuting Zheng Haibo Tan Zhenxing Zou |
| author_sort | Weiwei Peng |
| collection | DOAJ |
| description | Abstract Two novel koninginin derivatives, koningipyridines A and B (1 and 2), along with four known compounds (3˗6) were isolated from the EtOAc extract of the endophytic fungus Trichoderma koningiopsis SC-5. Among them, koningipyridine A featured an unprecedented pentacyclic ketal skeleton with the formation of a fascinating 6/6/5/6/5 fused ring system and shared a characteristic pyridine core, which represents the first example of nitrogen-containing koninginin-type natural product. Moreover, koningipyridine B was the first member in the koninginin family sharing a unique 6/6/5 dihydropyridine skeleton, and it was suggested to be the critical biosynthetic precursor of koningipyridine A. The structures of 1 and 2 were elucidated by the interpretation of 1D and 2D NMR spectroscopy, HRESIMS data, as well as theoretical calculations of 13C NMR and electronic circular dichroism (ECD). Moreover, all isolates were screened for antimicrobial activities against Staphylococcus aureus, MRSA, and Escherichia coli as well as the cytotoxic effects against three cancer cell lines (A549, Hela, and HepG2). Graphical Abstract |
| first_indexed | 2024-03-08T14:11:18Z |
| format | Article |
| id | doaj.art-817cb022f6594b6eabbc2d7189ab2139 |
| institution | Directory Open Access Journal |
| issn | 2192-2195 2192-2209 |
| language | English |
| last_indexed | 2024-03-08T14:11:18Z |
| publishDate | 2024-01-01 |
| publisher | SpringerOpen |
| record_format | Article |
| series | Natural Products and Bioprospecting |
| spelling | doaj.art-817cb022f6594b6eabbc2d7189ab21392024-01-14T12:42:36ZengSpringerOpenNatural Products and Bioprospecting2192-21952192-22092024-01-0114111310.1007/s13659-024-00429-zKoningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5Weiwei Peng0Qi Huang1Xin Ke2Wenxuan Wang3Yan Chen4Zihuan Sang5Chen Chen6Siyu Qin7Yuting Zheng8Haibo Tan9Zhenxing Zou10Xiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityXiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South UniversityAbstract Two novel koninginin derivatives, koningipyridines A and B (1 and 2), along with four known compounds (3˗6) were isolated from the EtOAc extract of the endophytic fungus Trichoderma koningiopsis SC-5. Among them, koningipyridine A featured an unprecedented pentacyclic ketal skeleton with the formation of a fascinating 6/6/5/6/5 fused ring system and shared a characteristic pyridine core, which represents the first example of nitrogen-containing koninginin-type natural product. Moreover, koningipyridine B was the first member in the koninginin family sharing a unique 6/6/5 dihydropyridine skeleton, and it was suggested to be the critical biosynthetic precursor of koningipyridine A. The structures of 1 and 2 were elucidated by the interpretation of 1D and 2D NMR spectroscopy, HRESIMS data, as well as theoretical calculations of 13C NMR and electronic circular dichroism (ECD). Moreover, all isolates were screened for antimicrobial activities against Staphylococcus aureus, MRSA, and Escherichia coli as well as the cytotoxic effects against three cancer cell lines (A549, Hela, and HepG2). Graphical Abstracthttps://doi.org/10.1007/s13659-024-00429-zTrichoderma koningiopsisEndophytic fungiSecondary metabolitesKoningipyridineCytotoxic activity |
| spellingShingle | Weiwei Peng Qi Huang Xin Ke Wenxuan Wang Yan Chen Zihuan Sang Chen Chen Siyu Qin Yuting Zheng Haibo Tan Zhenxing Zou Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 Natural Products and Bioprospecting Trichoderma koningiopsis Endophytic fungi Secondary metabolites Koningipyridine Cytotoxic activity |
| title | Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 |
| title_full | Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 |
| title_fullStr | Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 |
| title_full_unstemmed | Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 |
| title_short | Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5 |
| title_sort | koningipyridines a and b two nitrogen containing polyketides from the fungus trichoderma koningiopsis sc 5 |
| topic | Trichoderma koningiopsis Endophytic fungi Secondary metabolites Koningipyridine Cytotoxic activity |
| url | https://doi.org/10.1007/s13659-024-00429-z |
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