Pegriseofamines A-E: Five cyclopiazonic acid related indole alkaloids from the fungus Penicillium griseofulvum

Yu Liang; Hong Liao; Xuanni Chen; Qiwei Wang; Qin Li; Yong Shen; Yuyi Zheng; Xiao-Nian Li; Hucheng Zhu; Dongyan Li; Weiguang Sun; Chunmei Chen; Yonghui Zhang

doi:10.1016/j.bioorg.2023.106553

Pegriseofamines A-E: Five cyclopiazonic acid related indole alkaloids from the fungus Penicillium griseofulvum

Bioorg Chem. 2023 Jul:136:106553. doi: 10.1016/j.bioorg.2023.106553. Epub 2023 Apr 20.

Authors

Yu Liang¹, Hong Liao¹, Xuanni Chen¹, Qiwei Wang¹, Qin Li¹, Yong Shen¹, Yuyi Zheng¹, Xiao-Nian Li², Hucheng Zhu¹, Dongyan Li³, Weiguang Sun⁴, Chunmei Chen⁵, Yonghui Zhang⁶

Affiliations

¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China.
² State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, People's Republic of China.
³ Department of Pharmacy, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address: lidongyan2016@sina.com.
⁴ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China. Electronic address: weiguang_sun@hust.edu.cn.
⁵ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China. Electronic address: chenchunmei@hust.edu.cn.
⁶ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China. Electronic address: zhangyh@mails.tjmu.edu.cn.

PMID: 37119783
DOI: 10.1016/j.bioorg.2023.106553

Abstract

Five new cyclopiazonic acid related indole alkaloids, pegriseofamines A-E (1-5), were isolated from the fungus Penicillium griseofulvum. Their structures and absolute configurations were determined by NMR, HRESIMS, quantum-chemical calculation, and X-ray diffraction experiments. Among them, pegriseofamine A (1) possesses an undescribed 6/5/6/7 tetracyclic ring system generated by the fusion of an azepine and an indole unit via a cyclohexane, and the postulated biosynthetic origin of 1 was discussed. Compound 4 could relieve liver injury and prevent hepatocyte apoptosis in ConA-induced autoimmune liver disease.

Keywords: Alkaloid; Cyclopiazonic acid; Immunosuppression activity; Penicillium griseofulvum.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Fungi
Indole Alkaloids* / chemistry
Molecular Structure
Penicillium* / chemistry

Substances

cyclopiazonic acid
Indole Alkaloids

Supplementary concepts

Penicillium griseofulvum