DOI: 10.1021/acs.orglett.6c03809 ISSN: 1523-7060
Fluoindeneacids A and B: Antioxidant Cyclopentane-Containing Molecules with Enzyme-Triggered Nonenzymatic Skeletal Rearrangement
Chunfang Yang, Xin Pang, Yuchan Chen, Wei Liu, Weilin Chen, Sinan Cao, Weimin Zhang, Changsheng Zhang, Wenjun ZhangAbstract
Fluoindeneacids A and B (5 and 6, respectively), featuring an unprecedented indene core linked to a 2,3-dihydroxybenzoyl moiety, were isolated from the FlsO1-catalyzed reaction of prejadomycin (1). Their structures were established by spectroscopic analysis and ECD calculations. Biochemical and isotopic labeling studies indicate their formation via an enzyme-triggered, nonenzymatic skeletal rearrangement of putative precursor 10. Both compounds exhibited potent in vitro antioxidant activity and cytoprotection against H2O2-induced damage.