Isolation and structure elucidation of new PKCalpha inhibitors from Pinus flexilis.
Bioassay-guided fractionation of the CH2Cl2-MeOH extract of Pinus flexilis using an assay for protein kinase C (PKC) inhibitory activity led to the isolation of the two new bioactive diarylheptanoids (3R)-1,7-bis(3, 4-dihydroxyphenyl)-3-(beta-D-glucopyranosyl)heptan-3-ol (1) and its aglycon (3R)-1,7-bis(3,4-dihydroxyphenyl)heptan-3-ol (2), together with the three known bioactive compounds, hirsutenone (3), oregonin (4), and hirsutanonol (5). The IC50 values of compounds 1-5 in the PKC assay were 1.4, 1.6, 1.4, 8.6, and 4.6 microg/mL, respectively.
Lee
K K
KK
Department of Chemistry, Virginia Polytechnic and State University, Blacksburg, Virginia 24061-0212, USA.
Bahler
B D
BD
Hofmann
G A
GA
Mattern
M R
MR
Johnson
R K
RK
Kingston
D G
DG
D002942:Circular Dichroism; D036381:Diarylheptanoids; D004791:Enzyme Inhibitors / Q000302:isolation & purification* / Q000494:pharmacology; D005947:Glucose / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D019850:Heptanol / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D007527:Isoenzymes / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D010946:Plants, Medicinal / Q000737:chemistry*; D011493:Protein Kinase C / Q000037:antagonists & inhibitors*; D051571:Protein Kinase C-alpha; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
C117181:1,7-bis(3,4-dihydroxyphenyl)heptan-3-ol; D036381:Diarylheptanoids; D004791:Enzyme Inhibitors; D007527:Isoenzymes; D019850:Heptanol; C496628:PRKCA protein, human; D011493:Protein Kinase C; D051571:Protein Kinase C-alpha; D005947:Glucose