Pesimquinolones produced by Penicillium simplicissimum and their inhibitory activity on nitric oxide production

Chong Dai; Chunmei Chen; Danyingzi Guan; Hailun Chen; Fuxin Wang; Wenjing Wang; Yi Zang; Qin Li; Mengsha Wei; Xiaoxin Li; Xiaotian Zhang; Jianping Wang; Qun Zhou; Hucheng Zhu; Yonghui Zhang

doi:10.1016/j.phytochem.2020.112327

Pesimquinolones produced by Penicillium simplicissimum and their inhibitory activity on nitric oxide production

Phytochemistry. 2020 Jun:174:112327. doi: 10.1016/j.phytochem.2020.112327. Epub 2020 Mar 26.

Authors

Chong Dai¹, Chunmei Chen¹, Danyingzi Guan¹, Hailun Chen², Fuxin Wang¹, Wenjing Wang¹, Yi Zang¹, Qin Li¹, Mengsha Wei¹, Xiaoxin Li¹, Xiaotian Zhang¹, Jianping Wang¹, Qun Zhou³, Hucheng Zhu⁴, Yonghui Zhang⁵

Affiliations

¹ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China.
² Faculty of Medicine, Dentistry and Health, University of Sheffield, South Yorkshire, Sheffield, United Kingdom.
³ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China. Electronic address: zqtcm@163.com.
⁴ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China. Electronic address: zhuhucheng@hust.edu.cn.
⁵ Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, China. Electronic address: zhangyh@mails.tjmu.edu.cn.

PMID: 32222549
DOI: 10.1016/j.phytochem.2020.112327

Abstract

Eight undescribed quinolone alkaloids, pesimquinolones A-H, as well as six known compounds, were isolated from the solid culture broth of the fungus Penicillium simplicissimum. Their chemical structures were characterized by combined analyses of NMR spectroscopy and single-crystal X-ray crystallography. Pesimquinolones A-G are the first examples of naturally occurring quinolone alkaloids possessing a limonene moiety. Their anti-inflammatory activities on LPS-induced nitric oxide (NO) production in adherent cells were evaluated. Pesimquinolones A, E, G, and H showed promising suppressive effect on the production of NO with IC₅₀ values of 1.94, 1.29, 1.20, and 1.23 μM, respectively.

Keywords: Inhibitory activity on NO production; Penicillium simplicissimum; Quinolone alkaloids; Trichocomaceae.

MeSH terms

Alkaloids*
Anti-Inflammatory Agents
Molecular Structure
Nitric Oxide
Penicillium*

Substances

Alkaloids
Anti-Inflammatory Agents
Nitric Oxide