Spectasterols, Aromatic Ergosterols with 6/6/6/5/5, 6/6/6/6, and 6/6/6/5 Ring Systems from <i>Aspergillus spectabilis</i>
Mengsha Wei, Liping Huang, Qin Li, Xinyi Qiao, Ziming Zhao, Jie Yin, Aimin Fu, Jieru Guo, Xincai Hao, Lianghu Gu, Jianping Wang, Chunmei Chen, Hucheng Zhu, Yonghui Zhang
Abstract
Spectasterols A–E ( 1 – 5 ), aromatic ergosterols with unique ring systems, were isolated from Aspergillus spectabilis . Compounds 1 and 2 possess a 6/6/6/5/5 ring system with an additional cyclopentene, while 3 and 4 have an uncommon 6/6/6/6 ring system generated by the D-ring expansion via 1,2-alkyl shifts. Compound 3 exhibited cytotoxic activity (IC 50 6.9 μM) and induced cell cycle arrest and apoptosis in HL60 cells. Compound 3 was anti-inflammatory; it decreased COX-2 levels at the transcription and protein levels and inhibited the nuclear translocation of NF-κB p65.
Topics & Concepts
CyclopenteneStereochemistryRing (chemistry)ChemistryCytotoxic T cellApoptosisAspergillus nidulansBiologyBiochemistryIn vitroOrganic chemistryGeneMutantCatalysisNatural product bioactivities and synthesisMicrobial Natural Products and BiosynthesisSesquiterpenes and Asteraceae Studies