Isoxerophilusins A and B, Two Novel Polycyclic Asymmetric Diterpene Dimers from Isodon xerophilus: Structural Elucidation, Modification, and Inhibitory Activities against α-Glucosidase

Org Lett. 2024 Jul 26;26(29):6203-6208. doi: 10.1021/acs.orglett.4c02095. Epub 2024 Jul 14.

Abstract

Isoxerophilusins A (1) and B (2), two unprecedented diterpene heterodimers biogenetically from ent-atisanes and abietanes, were isolated from the rhizomes of Isodon xerophilus. Their structures were determined by extensive spectroscopic analysis and single-crystal X-ray diffraction. Selective esterification of 1 generated 11 new derivatives. All derivatives showed excellent α-glucosidase inhibitory activity in comparison to acarbose. Compounds 12 and 13 demonstrated significant inhibition against α-glucosidase with IC50 values of 4.92 and 3.83 μM, respectively.

MeSH terms

  • Crystallography, X-Ray
  • Dimerization
  • Diterpenes* / chemistry
  • Diterpenes* / isolation & purification
  • Diterpenes* / pharmacology
  • Glycoside Hydrolase Inhibitors* / chemistry
  • Glycoside Hydrolase Inhibitors* / isolation & purification
  • Glycoside Hydrolase Inhibitors* / pharmacology
  • Isodon* / chemistry
  • Molecular Structure
  • Rhizome / chemistry
  • Structure-Activity Relationship
  • alpha-Glucosidases* / metabolism

Substances

  • Glycoside Hydrolase Inhibitors
  • Diterpenes
  • alpha-Glucosidases