Quadristerols A-G: Seven undescribed ergosterols from Aspergillus quadrilineata

Mengsha Wei; Xiaoxin Li; Hong Liao; Linlin Liu; Qin Li; Weiguang Sun; Chunmei Chen; Hucheng Zhu; Yonghui Zhang

doi:10.1016/j.phytochem.2023.113785

Quadristerols A-G: Seven undescribed ergosterols from Aspergillus quadrilineata

Phytochemistry. 2023 Sep:213:113785. doi: 10.1016/j.phytochem.2023.113785. Epub 2023 Jun 30.

Authors

Mengsha Wei¹, Xiaoxin Li¹, Hong Liao¹, Linlin Liu¹, Qin Li¹, Weiguang Sun¹, Chunmei Chen², Hucheng Zhu³, Yonghui Zhang⁴

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 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: chenchunmei@hust.edu.cn.
³ 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: zhuhucheng@hust.edu.cn.
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, People's Republic of China. Electronic address: zhangyh@mails.tjmu.edu.cn.

PMID: 37393972
DOI: 10.1016/j.phytochem.2023.113785

Abstract

Quadristerols A-G, seven undescribed ergosterols, were obtained from Aspergillus quadrilineata. Their structures and absolute configurations were determined based on HRESIMS, NMR, quantum-chemical calculations, and single-crystal X-ray diffraction analyses. Quadristerols A-G featured ergosterol skeletons with different attachments; quadristerols A-C were three diastereoisomers possessing a 2-hydroxy-propionyloxy group at C-6, and quadristerols D-G were two pairs of epimers with a 2,3-butanediol group at C-6. All of these compounds were evaluated for their immunosuppressive activities in vitro. Quadristerols B and C showed excellent inhibitory effects against concanavalin A-induced T lymphocyte proliferation with IC₅₀ values of 7.43 and 3.95 μM, respectively, and quadristerols D and E strongly inhibited lipopolysaccharide-induced B lymphocyte proliferation with IC₅₀ values of 10.96 and 7.47 μM, respectively.

Keywords: Aspergillus quadrilineata; Ergosterols; Immunosuppressive activity; Trichocomaceae.

MeSH terms

Aspergillus* / chemistry
Crystallography, X-Ray
Ergosterol* / pharmacology
Magnetic Resonance Spectroscopy
Molecular Structure

Substances

Ergosterol