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Front. Plant Sci.
Sec. Plant Metabolism and Chemodiversity
Volume 14 - 2023 | doi: 10.3389/fpls.2023.1161420

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

 Zhenxing Zou1*, Weiwei Peng1,  Qi Huang1, Xin Ke1,  Wen-Xuan Wang1, Yan Chen1,  Zihuan Sang1, Chen Chen1, Siyu Qin1, Yuting Zheng1 and  Haibo Tan2
  • 1Central South University, China
  • 2South China Botanical Garden, Chinese Academy of Sciences (CAS), China

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Two novel koninginin derivatives, koningipyridines A (1) and B (2), together 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, the koningipyridine B was evidenced to be the first member in koninginin family sharing a unique 6/6/5 dihydropyridine skeleton, and it was chemo-logically suggested to be critical biosynthetic precursor of koningipyridine A. Their structures and absolute configurations were extensively established on the basis of NMR, HRESIMS, 13C NMR, and theoretical electronic circular dichroism (ECD) calculations. Moreover, all isolates were evaluated for their antimicrobial and cytotoxic activities, and all compounds showed weak activities against a panel of human cancer cell lines including A549, Hela, and HepG2.

Keywords: Trichoderma koningiopsis, endophytic fungi, secondary metabolites, koningipyridine, cytotoxic activity

Received: 08 Feb 2023; Accepted: 09 Mar 2023.

Copyright: © 2023 Zou, Peng, Huang, Ke, Wang, Chen, Sang, Chen, Qin, Zheng and Tan. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.

* Correspondence: Mx. Zhenxing Zou, Central South University, Changsha, China