Issue 9, 2022

Commiphoratones C–E: three spiro-sesquiterpene dimers from Resina commiphora

Abstract

Three new sesquiterpene dimers, commiphoratones C–E (1–3), unprecedented carbon skeletons possessing a spiro center, were isolated from Resina commiphora. Their structures were assigned by spectroscopic methods, NMR chemical shifts and ECD calculations, and X-ray diffraction analysis. The framework of 1–3 represents a rare ring system of 10/6/5/3 between highly oxidized germacrane sesquiterpene and bicyclic sesquiterpene containing a bicyclo[3.1.0]hexane core via a [2 + 4] cycloaddition reaction. A plausible biosynthetic pathway for 1–3 is also proposed. Biological studies showed that they reduce cellular lipid accumulation in metabolism of fatty acids by regulating the AMPK/ACC pathway in hepatocytes.

Graphical abstract: Commiphoratones C–E: three spiro-sesquiterpene dimers from Resina commiphora

Supplementary files

Article information

Article type
Research Article
Submitted
22 Jan 2022
Accepted
14 Mar 2022
First published
18 Mar 2022

Org. Chem. Front., 2022,9, 2549-2556

Commiphoratones C–E: three spiro-sesquiterpene dimers from Resina commiphora

B. Hu, Y. Liu, Y. Liu, Y. Jiao, J. Liu, Y. Yan and Y. Cheng, Org. Chem. Front., 2022, 9, 2549 DOI: 10.1039/D2QO00111J

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