Prenylated quinolinone alkaloids and prenylated isoindolinone alkaloids from the fungus Aspergillus nidulans

Qin Li; Chunmei Chen; Yan He; Mengsha Wei; Li Cheng; Xin Kang; Jianping Wang; Xincai Hao; Hucheng Zhu; Yonghui Zhang

doi:10.1016/j.phytochem.2019.112177

Prenylated quinolinone alkaloids and prenylated isoindolinone alkaloids from the fungus Aspergillus nidulans

Phytochemistry. 2020 Jan:169:112177. doi: 10.1016/j.phytochem.2019.112177. Epub 2019 Nov 8.

Authors

Qin Li¹, Chunmei Chen¹, Yan He², Mengsha Wei¹, Li Cheng³, Xin Kang¹, Jianping Wang¹, Xincai Hao⁴, Hucheng Zhu⁵, 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, People's Republic of China.
² Department of Pharmacy, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China.
³ Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy, Hubei University of Medicine, Shiyan, 442000, People's Republic of China.
⁴ Hubei Key Laboratory of Wudang Local Chinese Medicine Research, Hubei Engineering Technology Center for Comprehensive Utilization of Medicinal Plants, College of Pharmacy, Hubei University of Medicine, Shiyan, 442000, People's Republic of China. Electronic address: [email protected].
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, People's Republic of China. Electronic address: [email protected].
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, People's Republic of China. Electronic address: [email protected].

PMID: 31707275
DOI: 10.1016/j.phytochem.2019.112177

Abstract

Two undescribed prenylated quinolinone alkaloids, aspoquinolones E and F, and three undescribed prenylated isoindolinone alkaloids aspernidines F-H, were isolated from the fungus Aspergillus nidulans. Their structures and configurations were elucidated based on spectroscopic analyses and ECD spectra. Aspoquinolones E and F possess a C₁₀ moiety with an unusual 2,2,4-trimethyl-3oxa-bicyclo[3.1.0]hexane unit, and aspernidines F-H own a C₁₅ side chain. These compounds were evaluated for cytotoxic activities against five human cancer cell lines, compounds 1 and 5 exhibited strong inhibitory activities against A-549 and SW-480 cells with IC₅₀ values of 3.50 and 4.77 μM, respectively.

Keywords: Aspergillus nidulans (Trichocomaceae); Cytotoxic activities; Isoindolinone; Quinolinone.

MeSH terms

Alkaloids / chemistry
Alkaloids / isolation & purification
Alkaloids / pharmacology*
Antineoplastic Agents / chemistry
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Aspergillus nidulans / chemistry*
Cell Line, Tumor
Cell Proliferation / drug effects
Cell Survival / drug effects
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Molecular Structure
Phthalimides / chemistry
Phthalimides / isolation & purification
Phthalimides / pharmacology*
Prenylation
Quinolones / chemistry
Quinolones / isolation & purification
Quinolones / pharmacology*
Structure-Activity Relationship

Substances

Alkaloids
Antineoplastic Agents
Phthalimides
Quinolones
phthalimidine