Peniciriols A and B, two new citrinin derivatives from an endophytic fungus Penicillum citrinum TJNZ-27

Shanshan Wei; Zihuan Sang; Yanjiang Zhang; Huan Wang; Yan Chen; Hongxin Liu; Sasa Wang; Haibo Tan

doi:10.1016/j.fitote.2023.105572

Peniciriols A and B, two new citrinin derivatives from an endophytic fungus Penicillum citrinum TJNZ-27

Fitoterapia. 2023 Sep:169:105572. doi: 10.1016/j.fitote.2023.105572. Epub 2023 Jun 12.

Authors

Shanshan Wei¹, Zihuan Sang², Yanjiang Zhang³, Huan Wang⁴, Yan Chen², Hongxin Liu⁵, Sasa Wang⁶, Haibo Tan⁷

Affiliations

¹ 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; Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University for Nationalities, Nanning 530006, People's Republic of China; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
² 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.
³ 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; University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China.
⁴ 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; National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou, People's Republic of China.
⁵ State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Culture Collection and Application, Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou 510070, People's Republic of China.
⁶ Key Laboratory of Chemistry and Engineering of Forest Products, Guangxi University for Nationalities, Nanning 530006, People's Republic of China. Electronic address: wgsasa@163.com.
⁷ 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; National Engineering Research Center of Navel Orange, Gannan Normal University, Ganzhou, People's Republic of China. Electronic address: tanhaibo@scbg.ac.cn.

PMID: 37315718
DOI: 10.1016/j.fitote.2023.105572

Abstract

Two undescribed citrinin derivatives, named peniciriols A-B (1-2), together with six known compounds were isolated from endophytic fungus Penicillum citrinum TJNZ-27. The structures of two new compounds were well established by the detail interpretation of NMR and HRESIMS data as well as ECD measurement powered by molecular calculation. Among them, compound 1 shared an unprecedented dimerized citrinin skeleton with the formation of an intriguing 9H-xanthene ring system, whereas compound 2 possess a highly substituted phenylacetic acid skeleton, which was rarely-occurring in natural secondary metabolites. Moreover, these novel compounds were tested for cytotoxic and antibacterial activities, whereas these novel compounds did not exhibit any noticeable cytotoxic or antibacterial activities.

Keywords: Biological activity; Citrinin derivatives; Penicillum citrinum; Peniciriols A-B.

MeSH terms

Anti-Bacterial Agents
Citrinin*
Fungi
Molecular Structure
Penicillium* / chemistry

Substances

Citrinin
Anti-Bacterial Agents