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

• Published in: Bioorganic chemistry Vol. 136; p. 106553
• Main Authors: Liang, Yu, Liao, Hong, Chen, Xuanni, Wang, Qiwei, Li, Qin, Shen, Yong, Zheng, Yuyi, Li, Xiao-Nian, Zhu, Hucheng, Li, Dongyan, Sun, Weiguang, Chen, Chunmei, Zhang, Yonghui
• Format: Journal Article
• Language: English
• Published: SAN DIEGO Elsevier Inc 01.07.2023; Elsevier
• Subjects: Alkaloid; Biochemistry & Molecular Biology; Chemistry; Chemistry, Organic; Cyclopiazonic acid; Fungi; Immunosuppression activity; Indole Alkaloids - chemistry; Life Sciences & Biomedicine; Molecular Structure; Penicillium - chemistry; Penicillium griseofulvum; Physical Sciences; Science & Technology; Alkaloid; Cyclopiazonic acid; Penicillium griseofulvum; Immunosuppression activity
• ISSN: 0045-2068; 1090-2120
• DOI: 10.1016/j.bioorg.2023.106553

Five new cyclopiazonic acid related indole alkaloids, pegriseofamines A−E (1–5), were isolated from the fungus Penicillium griseofulvum. 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 pegriseofamine D (4) could relieve liver injury and prevent hepatocyte apoptosis in ConA-induced autoimmune liver disease. [Display omitted] •Five new cyclopiazonic acid indole alkaloids (1–5) were isolated from Penicillium griseofulvum.•Their configurations were elucidated by crystallography and quantum-chemical analyses.•Compound 1 possesses an undescribed 6/5/6/7 tetracyclic ring system.•Compound 4 could relieve liver injury and prevent hepatocyte apoptosis in ConA-induced autoimmune liver disease. 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.