Meroterpenes with Toll-Like Receptor 3 Regulating Activity from the Endophytic Fungus Guignardia mangiferae

 

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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.

^* These authors contributed equally to the work.

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