Title
Acronyrones A–C, unusual prenylated acetophenones from Acronychia pedunculata
Author
Li-Xia Lv, Yan Wu, Hao-Xuan He, Ni-Ping Li, Wei Zhao, Yun-Qi Fan, Xia Wei, Jun-Cheng Su, Qi Wang, Ji-Hong Gu
Year
2022
Journal
Fitoterapia
Abstract
Two novel prenylated acetophenones with new carbon skeletons, acronyrones A and B (1 and 2), and a new analogue, acronyrone C (3), together with two known compounds (4 and 5) were isolated from the leaves of Acronychia pedunculata. Their structures with absolute configurations were identified by interpretation of spectroscopic data, single crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compounds 1 and 2 represent the first example of prenylated acetophenones possessed a C7 (1) and a C6 (2) side chain, forming a 4-isobutylchroman-2-one unit and a 3-(2-methylpropylidene)benzofuran-2(3H)-one moiety with the acetophenone core, respectively. In addition, compound 4 exhibited significant dose-dependent transcriptional activation effect against retinoid X receptor-α (RXRα), and could be regarded as a new type of non-classical RXR ligand.
Instrument
FT/IR-480 plus, V-550, P-1020
Keywords
Acronyrones, acetophenones, Acronychia pedunculata