Secondary Metabolites of the Lichen-Associated Fungus Apiospora montagnei

Research paper by Hao Wang, Blessing O. Umeokoli, Peter Eze, Christian Heering, Christoph Janiak, Werner E.G. Müller, Raha S. Orfali, Rudolf Hartmann, Haofu Dai, Wenhan Lin, Zhen Liu, Peter Proksch

Indexed on: 23 Mar '17Published on: 19 Mar '17Published in: Tetrahedron Letters


The endolichenic fungus Apiospora montagnei isolated from the lichen Cladonia sp. was cultured on solid rice medium, yielding the new diterpenoid libertellenone L (1), the new pyridine alkaloid, 23-O-acetyl-N-hydroxyapiosporamide (2) and the new xanthone derivative 8-hydroxy-3-hydroxymethyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ether (3) together with 19 known compounds (4–22). The structures of the new compounds were elucidated by 1D and 2D NMR spectra as well as by HRESIMS data. The absolute configuration of the new 6,7-seco-libertellenone derivative 1 was determined by single-crystal X-ray diffraction. Four additional known compounds 23–26 were isolated when NaCl or NH4Cl were added to solid rice medium. Compounds 7–9, 18 and 26 exhibited significant cytotoxicity against the L5178 murine lymphoma cell line with IC50 values of 2.6, 0.2, 2.1, 2.7 and 1.7 μM, respectively.

Graphical abstract 10.1016/j.tetlet.2017.03.052.jpg
Figure 10.1016/j.tetlet.2017.03.052.0.jpg
Figure 10.1016/j.tetlet.2017.03.052.1.jpg
Figure 10.1016/j.tetlet.2017.03.052.2.jpg
Figure 10.1016/j.tetlet.2017.03.052.3.jpg
Figure 10.1016/j.tetlet.2017.03.052.4.jpg