Bioassay-guided fractionation of the CH2Cl2-MeOH extract of Pinus flexilis
using an assay for protein kinase C (PKC) inhibitory activity led to the is
olation of the two new bioactive diarylheptanoids (3R)-1,7-bis(3,4-dihydrox
yphenyl)-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 bioa
ctive compounds, hirsutenone (3), oregonin (4), and hirsutanonol (5). The I
C50 values of compounds 1-5 in the PKC assay were 1.4, 1.6, 1.4, 8.6, and 4
.6 mu g/mL, respectively.