Discovery of a new series of jatrophane and lathyrane diterpenes as potent and specific P-glycoprotein modulators

Org Biomol Chem. 2008 May 21;6(10):1756-62. doi: 10.1039/b800485d. Epub 2008 Mar 28.

Abstract

A new series of diterpenes, the jatrophanes euphoscopin M (1), euphoscopin N (2) and euphornin L (3), and the lathyrane euphohelioscopin C (7) were isolated from plants of Euphorbia helioscopia L., together with four other known analogues, euphoscopin C (4), euphornin (5), epieuphoscopin B (6) and euphohelioscopin A (8). The new compound stereostructures were elucidated by NMR analysis and computational data. The resulting isolated diterpenes were found to be potent inhibitors of P-glycoprotein (ABCB1), while showing an absence of significant activity against BCRP (ABCG2), despite the high substrate overlapping of these transporters, thus including them in the third-generation class of specific multidrug transporter modulators.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • ATP Binding Cassette Transporter, Subfamily B, Member 1 / chemistry*
  • Animals
  • Diterpenes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mice
  • Models, Molecular
  • Molecular Structure
  • NIH 3T3 Cells
  • Stereoisomerism

Substances

  • ATP Binding Cassette Transporter, Subfamily B, Member 1
  • Diterpenes
  • jatrophane
  • lathyrane