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Pyrazine Derivatives with Osteoclast Differentiation Inhibitory Activities from the Endophytic Fungus Alternaria sp.
Dongliang Xiao1,2, Shiqi Ai1,2, Xuefei Li1,2
1College of Life and Health, Dalian University, Dalian 116622, P. R. China.
None:
Four new pyrazine derivatives, namely (S,E)-1-((5-(3-hydroxy-2-(hydroxymethyl)styryl)-3,6-dimethylpyrazin-2-yl)methyl)-1,3-dihydroisobenzofuran-4-ol (1), (S,E)-1-((5-(3-hydroxy-2-(methoxymethyl)styryl)-3,6-dimethylpyrazin-2-yl)methyl)-1,3-dihydroisobenzofuran-4-ol (2), (S,Z)-1-((5-(3-hydroxy-2-(methoxymethyl)styryl)-3,6-dimethylpyrazin-2-yl)methyl)-1,3-dihydroisobenzofuran-4-ol (3), and (S)-1-((5-(3-hydroxy-2-(methoxymethyl)phenethyl)-3,6-dimethylpyrazin-2-yl)methyl)-1,3-dihydroisobenzofuran-4-ol (4), together with one new 1,3-dihydroisobenzofuran derivative, (S)-2-(4-hydroxy-1,3-dihydroisobenzofuran-1-yl)acetamide (5), were isolated from the endophytic fungus Alternaria sp. HJT-Y7 collected from the leaves of Rhodiola tibetica. Their structures were determined based on extensive spectroscopic analysis and comparison of experimental and calculated electronic circular dichroism (ECD) curves. 1, 4, and 5 significantly inhibited osteoclast differentiation in RANKL-induced RAW264.7 cells and markedly restored bone mineralization in a dexamethasone-induced zebrafish osteoporosis model. These results highlight the potential of 1, 4, and 5 as promising candidates for osteoporosis therapy.
