title: Meroterpenes with toll-like receptor 3 regulating activity from the endophytic fungus Guignardia mangiferae.
abstract: The endophytic fungus Guignardia mangiferae isolated from Ilex cornuta leaves was shown to produce a family of meroterpenes with toll-like receptor 3 regulating activity (1-9), of which 1-3 possessed new structures. The absolute stereochemistry of 1-3 was assigned through a combination of nuclear magnetic resonance experiments, chemical derivation, CD spectra, and single-crystal X-ray diffraction analyses (CuK α ). The precursor labeled cultivation suggests that these meroterpenes are most likely assembled through terpenoid-shikimate pathways. Moreover, meroterpenes 1-3, 5-7, and 9 selectively upregulate, but 4 and 8 downregulate the toll-like receptor 3 expression in mouse dendritic cells at 10.0 µM.
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Wen Bo
authors.initials: WB
authors.lastname: Han
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Huan
authors.initials: H
authors.lastname: Dou
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Wei Hua
authors.initials: WH
authors.lastname: Yuan
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Wei
authors.initials: W
authors.lastname: Gong
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Ya Yi
authors.initials: YY
authors.lastname: Hou
authors.affiliation: Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia and Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
authors.forename: Seik Weng
authors.initials: SW
authors.lastname: Ng
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing, P. R. China.
authors.forename: Ren Xiang
authors.initials: RX
authors.lastname: Tan
mesh_terms: D001203:Ascomycota / Q000737:chemistry*; D060026:Endophytes; D005786:Gene Expression Regulation; D030017:Ilex / Q000382:microbiology*; D015394:Molecular Structure; D018515:Plant Leaves / Q000382:microbiology; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D051196:Toll-Like Receptor 3 / Q000737:chemistry / Q000378:metabolism*
chemical_list: C495344:TLR3 protein, human; D013729:Terpenes; D051196:Toll-Like Receptor 3