Citrifurans A–D, Four Dimeric Aromatic Polyketides with New Carbon Skeletons from the Fungus Aspergillus sp.

Lipopolysaccharides Molecular Structure Cell Survival Pigments, Biological Nitric Oxide 01 natural sciences 0104 chemical sciences Mice Aspergillus RAW 264.7 Cells Polyketides Animals Benzopyrans Furans Dimerization
DOI: 10.1021/acs.orglett.7b01823 Publication Date: 2017-07-20T15:39:18Z
ABSTRACT
Citrifurans A-D (1-4), metabolized by an Aspergillus sp., are unusual dimers of azaphilone and furanone derivatives. Michael addition was thought to be the pivotal procedure in their biosynthesis, and different addition sites generated two new different carbon skeletons. Their structures were elucidated on the basis of spectroscopic methods, single-crystal X-ray diffraction, chemical conversion, and electronic circular dichroism analyses. Compounds 1-3 showed moderate inhibitory activities against LPS-induced NO production in RAW 264.7 macrophages with IC50 values of 18.3, 22.6, and 25.3 μM, respectively.
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