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Tytuł:
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New secondary metabolites with immunosuppressive activity from the phytopathogenic fungus Bipolaris maydis.
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Autorzy:
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Duan X; 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.
Tan X; 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.
Gu L; 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.
Liu J; 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.
Hao X; 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.
Tao L; 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.
Feng H; 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.
Cao Y; 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.
Shi Z; 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.
Duan Y; 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.
Deng M; 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.
Chen G; 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: .
Qi C; 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: .
Zhang Y; 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: .
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Źródło:
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Bioorganic chemistry [Bioorg Chem] 2020 Jun; Vol. 99, pp. 103816. Date of Electronic Publication: 2020 Apr 09.
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Typ publikacji:
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Journal Article; Research Support, Non-U.S. Gov't
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Język:
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English
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Imprint Name(s):
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Publication: Amsterdam : Elsevier
Original Publication: New York, London, Academic Press.
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MeSH Terms:
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Bipolaris/*chemistry
Immunosuppressive Agents/*pharmacology
Sesterterpenes/*pharmacology
Animals ; Bipolaris/metabolism ; Cell Proliferation/drug effects ; Dose-Response Relationship, Drug ; Immunosuppressive Agents/chemistry ; Immunosuppressive Agents/metabolism ; Lipopolysaccharides/antagonists & inhibitors ; Lipopolysaccharides/pharmacology ; Male ; Mice ; Mice, Inbred C57BL ; Molecular Structure ; Orchidaceae/chemistry ; Orchidaceae/metabolism ; Plant Leaves/chemistry ; Plant Leaves/metabolism ; Sesterterpenes/chemistry ; Sesterterpenes/metabolism ; Spleen/drug effects ; Structure-Activity Relationship
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Contributed Indexing:
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Keywords: Bipolaris maydis; Immunosuppressive; Meroterpenoid; Murine splenocytes; Sesterterpene
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Substance Nomenclature:
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0 (Immunosuppressive Agents)
0 (Lipopolysaccharides)
0 (Sesterterpenes)
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Entry Date(s):
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Date Created: 20200420 Date Completed: 20210302 Latest Revision: 20210302
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Update Code:
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20240104
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DOI:
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10.1016/j.bioorg.2020.103816
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PMID:
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32305693
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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 IC 50 values of 5.28 and 9.38 μM, respectively, and also suppress the murine splenocytes proliferation activated by lipopolysaccharide (LPS), with IC 50 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.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2020 Elsevier Inc. All rights reserved.)
