Aspergilfuranones A-D, four norlignanolides from the Peucedanum praeruptorum endophytic fungus Aspergillus udagawae

• Published in: Tetrahedron Vol. 82; pp. 131951 - 131956
• Main Authors: Wang, Guo-Kai, Li, Yuan, Liu, Hai-Tao, Su, Jie-Li, Luo, Lan, Zhu, Jian-Yong, Wang, Kou, Liu, Jin-Song
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.02.2021; Elsevier
• Subjects: Aspergillus udagawe; Chemistry; Chemistry, Organic; Cytotoxicity; Endophytic fungus; Norlignanolide; Physical Sciences; Science & Technology; Cytotoxicity; Aspergillus udagawe; Endophytic fungus; Norlignanolide
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2021.131951

Aspergilfuranones A-D, four unpredicted norlignanolides (1–4), along with eight known compounds (5–12) were isolated from the endophytic fungus Aspergillus udagawae which was cultured on solid rice medium isolated from Peucedanum praeruptorum. The structures of these new compounds (1–4) were elucidated via comprehensive 1D/2D NMR, HRESIMS data analysis and the absolute configuration were determined by ECD calculations. New compounds were evaluated for their in vitro cytotoxic activity and aspergilfuranone A (1) exhibited a potent cytotoxic effect on human malignant melanoma A375 cells, with an IC50 value of 10.8 μM, being more active than the positive control, 5-FU (IC50 = 16.2 μM). Morphological features of apoptosis activities were evaluated in 1-treated melanoma A375 cells. Morphological changes analysis showed that aspergilfuranone A significantly induced A375 cell apoptosis in a dose-dependent manner. [Display omitted] •Four unpredicted norlignanolides have been isolated from endophytic fungus Aspergillus udagawae.•The absolute configuration of new compounds were determined by ECD calculations.•Compound 1 exhibited a potent cytotoxic against A375 human melanoma cells.