Sulfur-Containing Phenolic Compounds from the Cave Soil-Derived Aspergillus fumigatus GZWMJZ-152

作者：Yanchao Xu, Wen Liu, Dan Wu, Wenwen He, Mingxing Zuo, Dongyang Wang, Peng Fu, Liping Wang, Weiming Zhu · 发表于：Journal of Natural Products · 年份：2022 · DOI：10.1021/acs.jnatprod.1c01158 · 被引用次数：19 · 研究领域：Microbial Natural Products and Biosynthesis、Sulfur-Based Synthesis Techniques、Fungal Biology and Applications

Six new sulfur-containing phenolic compounds ( 1 – 6 ) and their putative metabolic precursors ( 7 – 9 ) were isolated from the cave soil-derived fungus Aspergillus fumigatus GZWMJZ-152. Compound 1 represents an unusual benzophenone–diketopiperazine hybrid via a thioether linker, while compound 2 contains a naturally rare sulfoxide group. Both compounds 2 and 3 were initially isolated as racemic mixtures and then purified as the enantiomerically pure (+)- 2, (−)- 2, (+)- 3, and (−)- 3, respectively. Their structures, including absolute configurations, were elucidated by spectroscopic analysis, X-ray diffraction, and the calculations of electronic circular dichroism. The antioxidant activity of compounds 1 – 9 was evaluated based on oxygen radical absorbance capacity, 2,2-diphenyl-1-picrylhydrazyl radical scavenging, and the protective effect on the PC12 cell line against H 2 O 2 -induced damage. Compounds 5 – 7 and 9 showed radical-scavenging activity against 2,2-diphenyl-1-picrylhydrazyl free radicals with the IC 50 values of 3.45 ± 0.02, 23.73 ± 0.08, 18.90 ± 0.16, and 17.27 ± 0.15 μM, respectively. Compounds (±)- 2, 4, 7, and 8 exhibited potent antioxidant capacity with oxygen radical absorbance capacity values of 1.73 ± 0.13, 1.65 ± 0.03, 6.14 ± 0.35, and 1.55 ± 0.04 μmol TE/μmol, respectively. Compounds (±)- 2 and (±)- 3 also exhibited protective effects on oxidative injury of PC12 cells induced by H 2 O 2 .