Constituents from the stem wood of Euphorbia quinquecostata with phorbol dibutyrate receptor-binding inhibitory activity.
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.
Mbwambo
Z H
ZH
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago 60612, USA.
Lee
S K
SK
Mshiu
E N
EN
Pezzuto
J M
JM
Kinghorn
A D
AD
D000818:Animals; D001923:Brain Chemistry / Q000502:physiology; D029742:Caenorhabditis elegans Proteins; D002352:Carrier Proteins; D002417:Cattle; D009682:Magnetic Resonance Spectroscopy; D015240:Phorbol 12,13-Dibutyrate / Q000378:metabolism*; D010946:Plants, Medicinal / Q000737:chemistry*; D011493:Protein Kinase C / Q000378:metabolism*; D011955:Receptors, Drug / Q000378:metabolism*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014934:Wood
D029742:Caenorhabditis elegans Proteins; D002352:Carrier Proteins; D011955:Receptors, Drug; C083141:phorbol ester binding protein; C027776:phorbol ester receptor; D015240:Phorbol 12,13-Dibutyrate; D011493:Protein Kinase C