2. Academic Validation
  3. New secondary metabolites with immunosuppressive activity from the phytopathogenic fungus Bipolaris maydis

New secondary metabolites with immunosuppressive activity from the phytopathogenic fungus Bipolaris maydis

  • Bioorg Chem. 2020 Jun;99:103816. doi: 10.1016/j.bioorg.2020.103816.
Xueyan Duan 1,  Xiaosheng Tan 2,  Lianghu Gu 1,  Junjun Liu 1,  Xincai Hao 3,  Li Tao 1,  Hao Feng 2,  Yunfang Cao 1,  Zhengyi Shi 1,  Yulin Duan 1,  Mengyi Deng 1,  Gang Chen 4,  Changxing Qi 5,  Yonghui Zhang 6
Affiliations

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 Institute of Organ Transplantation, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China; Key Laboratory of Organ Transplantation, Ministry of Education, People's Republic of China; NHC Key Laboratory of Organ Transplantation, People's Republic of China; Key Laboratory of Organ Transplantation, Chinese Academy of Medical Sciences, 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 Institute of Organ Transplantation, Tongji Hospital, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China; Key Laboratory of Organ Transplantation, Ministry of Education, People's Republic of China; NHC Key Laboratory of Organ Transplantation, People's Republic of China; Key Laboratory of Organ Transplantation, Chinese Academy of Medical Sciences, People's Republic of China. Electronic address: gchen@tjh.tjmu.edu.cn.
  • 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: qichangxing@hust.edu.cn.
  • 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: zhangyh@mails.tjmu.edu.cn.
PMID: 32305693 DOI: 10.1016/j.bioorg.2020.103816
Abstract

Three previously undescribed compounds, including a meroterpenoid, guignardone T (1), and two ophiobolin-type sesterterpenoids, maydispenoids A and B (2 and 3), along with four known compounds (4-7), were isolated from the phytopathogenic fungus Bipolaris maydis collected from Anoectochilus roxburghii (Wall.) Lindl leaves. The structures of all undescribed compounds were elucidated by spectroscopic analysis, electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction. Structurally, maydispenoids A was characterized by a fascinating decahydro-3-oxacycloocta[cd]pentalene fragment. It is notable that the compounds 2 and 3 exhibited potential inhibitory activity in anti-CD3/anti-CD28 monoclonal Antibodies (mAbs) stimulated murine splenocytes proliferation, with IC50 values of 5.28 and 9.38 μM, respectively, and also suppress the murine splenocytes proliferation activated by lipopolysaccharide (LPS), with IC50 values of 7.25 and 16.82 μM, respectively. This is the first report of ophiobolin-type sesterterpenoids as immunosuppressor, and may provide new chemical templates for the development of new immunosuppressive drugs for autoimmune disease treatment.

Keywords

Bipolaris maydis; Immunosuppressive; Meroterpenoid; Murine splenocytes; Sesterterpene.

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