Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5

doi:10.1007/s13659-024-00429-z

Natural Products and Bioprospecting ›› 2024, Vol. 14 ›› Issue (1): 8-8.DOI: 10.1007/s13659-024-00429-z

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Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5

Weiwei Peng^1,3, Qi Huang^1,4, Xin Ke^1,3, Wenxuan Wang¹, Yan Chen^1,3, Zihuan Sang^1,3, Chen Chen^1,3, Siyu Qin¹, Yuting Zheng¹, Haibo Tan^1,2,3, Zhenxing Zou¹

1. Xiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, 410013, People's Republic of China;
2. National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou, 341000, People's Republic of China;
3. Key Laboratory of National Forestry and Grassland Administration on Plant Conservation and Utilization in Southern China, State Key Laboratory of Plant Diversity and Specialty Crops, Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, 510650, People's Republic of China;
4. Department of Pharmacy, Xiangya Hospital, Central South University, Changsha, 410013, People's Republic of China

Received:2023-12-07 Online:2024-02-19 Published:2024-02-24
Contact: Haibo Tan,E-mail:tanhaibo@scbg.ac.cn;Zhenxing Zou,E-mail:zouzhenxing@csu.edu.cn
Supported by:
Financial support for this research was provided by the National Natural Science Foundation of China (Nos. 82173711 and 82003929), Youth Innovation Promotion Association of CAS (2020342), Natural Science Foundation of Hunan Province (Nos. 2021JJ30917 and 2021JJ40993), Key Research and Development Project of Hainan Province (No. ZDYF2022SHFZ048), and the Central South University postgraduate independent exploration and innovation project (No. 2022zzts0899).

Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5

Weiwei Peng^1,3, Qi Huang^1,4, Xin Ke^1,3, Wenxuan Wang¹, Yan Chen^1,3, Zihuan Sang^1,3, Chen Chen^1,3, Siyu Qin¹, Yuting Zheng¹, Haibo Tan^1,2,3, Zhenxing Zou¹

1. Xiangya School of Pharmaceutical Sciences, Hunan Key Laboratory of Diagnostic and Therapeutic Drug Research for Chronic Diseases, Central South University, Changsha, 410013, People's Republic of China;
2. National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou, 341000, People's Republic of China;
3. Key Laboratory of National Forestry and Grassland Administration on Plant Conservation and Utilization in Southern China, State Key Laboratory of Plant Diversity and Specialty Crops, Key Laboratory of South China Agricultural Plant Molecular Analysis and Genetic Improvement, Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou, 510650, People's Republic of China;
4. Department of Pharmacy, Xiangya Hospital, Central South University, Changsha, 410013, People's Republic of China

通讯作者: Haibo Tan,E-mail:tanhaibo@scbg.ac.cn;Zhenxing Zou,E-mail:zouzhenxing@csu.edu.cn
基金资助:
Financial support for this research was provided by the National Natural Science Foundation of China (Nos. 82173711 and 82003929), Youth Innovation Promotion Association of CAS (2020342), Natural Science Foundation of Hunan Province (Nos. 2021JJ30917 and 2021JJ40993), Key Research and Development Project of Hainan Province (No. ZDYF2022SHFZ048), and the Central South University postgraduate independent exploration and innovation project (No. 2022zzts0899).

Abstract

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).

Key words: Trichoderma koningiopsis, Endophytic fungi, Secondary metabolites, Koningipyridine, Cytotoxic activity

摘要： 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).

关键词: Trichoderma koningiopsis, Endophytic fungi, Secondary metabolites, Koningipyridine, Cytotoxic activity

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[J]. Natural Products and Bioprospecting, 2024, 14(1): 8-8.

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Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5

Koningipyridines A and B, two nitrogen-containing polyketides from the fungus Trichoderma koningiopsis SC-5

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