Oxepinamides: Novel Liver X Receptor Agonists from Aspergillus puniceus

• Published in: European Journal of Organic Chemistry Vol. 2011; no. 4; pp. 802 - 807
• Main Authors: Lu, Xin-Hua, Shi, Qing-Wen, Zheng, Zhi-Hui, Ke, Ai-Bing, Zhang, Hua, Huo, Chang-Hong, Ma, Ying, Ren, Xiao, Li, Ye-Ying, Lin, Jie, Jiang, Qin, Gu, Yu-Cheng, Kiyota, Hiromasa
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.02.2011; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: Aspergillus puniceus; Biological activity; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocycles; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Natural products; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Structure elucidation; Heterocycles; METABOLITES; FUNGUS; Natural products; NUCLEAR RECEPTORS; Aspergillus puniceus; Structure elucidation; Biological activity; LXRS; Agonist; Configuration; Molecular structure; Nitrogen heterocycle; Liver; NMR spectrometry; Natural compound; Oxygen heterocycle; X ray diffraction; Fungi; Aspergillus; Pyrimidine derivatives; Fungi Imperfecti; Spectrophotometry; Mass spectrometry; Structural analysis; Biological receptor; Crystalline structure
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201000812

Four novel oxepin‐containing pyrimidines, namely oxepinamides D–G (1–4), were isolated from cultures of Aspergillus puniceus F02Z‐1744. The structures of 1–4 were elucidated by analyzing their spectroscopic data generated by 1D and 2D NMR and MS methods. The configurations of 1 and 2 were established based on single‐crystal X‐ray crystallographic analysis. All four compounds 1–4 showed transcriptional activation on Liver X Receptor α (LXRα) with EC50 values of 10.6, 12.8, 13.6, and 12.1 μM, respectively. Oxepinamides D–G, which are four novel oxepin‐containing pyrimidines, were isolated from cultures of Aspergillus puniceus F02Z‐1744. All four compounds showed moderate transcriptional activation on LXRα (Liver X Receptor), whereas no effects were observed on FXRα, PPARα, PPARβ, PPARγ, RARα, RXRα, or ERα at concentrations of 30 μM.