Cadinane Sesquiterpenoids and Their Glycosides from Alangium chinense That Inhibit Spontaneous Calcium Oscillations

J Nat Prod. 2022 Mar 25;85(3):599-606. doi: 10.1021/acs.jnatprod.1c00978. Epub 2021 Dec 26.

Abstract

Nine new cadinane sesquiterpenoids, alanenses A-I (1-9), were isolated from the leaves of Alangium chinense together with three previously reported analogues (10-12). The structures of these molecules were elucidated by interpretation of spectroscopic and spectrometric data. Absolute configurations were established by the comparison of experimental and calculated ECD data, chemical degradation studies for sugar moieties, and a single-crystal X-ray diffraction analysis. Compounds 1 and 2 were isolated as racemates, and enantiopurification was achieved by chiral HPLC. Compounds 3-5 are glycosylated cadinanes bearing a β-d-glucose unit, while compounds 6-9 incorporate a hydroxymethyl group in either the free form or additional ring fusion. The structure of compound 11 was originally misassigned and later revised using additional NMR data. The corrected structure is here supported by X-ray single-crystal analysis. Compounds 1 and 2 inhibit spontaneous calcium channel oscillations at low micromolar concentrations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alangiaceae* / chemistry
  • Calcium Signaling
  • Glycosides / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes* / chemistry

Substances

  • Glycosides
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • cadinane