Constituents from the stem wood of Euphorbia quinquecostata with phorbol dibutyrate receptor-binding inhibitory activity

J Nat Prod. 1996 Nov;59(11):1051-5. doi: 10.1021/np960412e.

Abstract

Bioassay-guided fractionation of an EtOAc extract of the stem wood of Euphorbia quinquecostata using a phorbol dibutyrate receptor-binding assay system as a monitor yielded four inhibitory isolates (1-4), inclusive of one new compound, 17-hydroxyingenol 20-hexadecanoate (1), and three previously known compounds, ingenol 20-hexadecanoate (2), ent-16 alpha,17-dihydroxyatisan-3-one (3), and ent-3 beta,16 alpha,17-trihydroxyatisane (4). Also isolated from this extract were 10 constituents inactive in this bioassay, namely, 2,2'-dihydroxy-4,6-dimethoxy-3-methylacetophenone (5), a new structure, and nine known compounds identified as ent-13S-hydroxyatis-16-ene-3, 14-dione; 2-hydroxy-4,6-dimethoxyacetophenone (xanthoxylin); 2-hydroxy-4,6-dimethoxy-3-methylacetophenone; 6-hydroxy-7-methoxycoumarin; lupeol acetate; beta-sitosterol; sitosterol beta-D-glucopyranoside; 6,7,8-trimethoxycoumarin; and 3,3',4'-tri-O-methyl-4-O-[alpha-L-rhamnopyranosyl (1"'-->6")-beta-D-glucopyranosyl]ellagic acid. The structures of compounds 1 and 5 were established by chemical and spectroscopic methods.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Brain Chemistry / physiology
  • Caenorhabditis elegans Proteins*
  • Carrier Proteins
  • Cattle
  • Magnetic Resonance Spectroscopy
  • Phorbol 12,13-Dibutyrate / metabolism*
  • Plants, Medicinal / chemistry*
  • Protein Kinase C / metabolism*
  • Receptors, Drug / metabolism*
  • Spectrometry, Mass, Fast Atom Bombardment
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Wood*

Substances

  • Caenorhabditis elegans Proteins
  • Carrier Proteins
  • Receptors, Drug
  • phorbol ester binding protein
  • phorbol ester receptor
  • Phorbol 12,13-Dibutyrate
  • Protein Kinase C