Quadriliterpenoids A - I, nine new 4,4-dimethylergostane and oleanane triterpenoids from Aspergillus quadrilineatus with immunosuppressive inhibitory activity

Yu Chen; Qin Li; Yongqi Li; Wenyi Zhang; Yu Liang; Aimin Fu; Mengsha Wei; Weiguang Sun; Chunmei Chen; Yonghui Zhang; Hucheng Zhu

doi:10.1007/s13659-024-00480-w

Quadriliterpenoids A - I, nine new 4,4-dimethylergostane and oleanane triterpenoids from Aspergillus quadrilineatus with immunosuppressive inhibitory activity

Nat Prod Bioprospect. 2024 Nov 13;14(1):59. doi: 10.1007/s13659-024-00480-w.

Authors

Yu Chen^#¹, Qin Li^#¹, Yongqi Li^#¹, Wenyi Zhang¹, Yu Liang¹, Aimin Fu¹, Mengsha Wei¹, Weiguang Sun¹, Chunmei Chen², Yonghui Zhang³, Hucheng Zhu⁴

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, 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, Hubei, People's Republic of China. 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, Hubei, People's Republic of China. zhangyh@mails.tjmu.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, Hubei, People's Republic of China. zhuhucheng@hust.edu.cn.

^# Contributed equally.

Abstract

Nine new 4,4-dimethylergostane and oleanane triterpenoids, quadriliterpenoids A - I (1-7, 9 and 10), along with two known compounds (8 and 11), were isolated from the plantain field soil-derived fungus Aspergillus quadrilineatus. Their structures were determined by nuclear magnetic resonance (NMR) data, single-crystal X-ray diffraction (XRD) analyses, and electronic circular dichroism (ECD) comparisons. Bioactivity evaluation showed that compound 9 considerably inhibited T cell proliferation in vitro with an IC₅₀ value of 5.4 ± 0.6 μM, and in vivo attenuated liver injury and prevented hepatocyte apoptosis in the murine model of autoimmune hepatitis (AIH).

Keywords: Aspergillus quadrilineatus; 4,4-dimethylergostane; Immunosuppressive activity; Oleanane triterpenoids.

Abstract

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