Cell suspension cultures of the scab-resistant apple (Malus x domestic
a) cultivar Liberty were challenged with yeast extract to mimic the ef
fect of biological stress such as fungal invasion. The cells responded
to the challenge by production of novel compounds. Suspension culture
s of the scab-susceptible cultivar McIntosh, when similarly challenged
, showed no detectable response. The major compound produced by scab-r
esistant cells in response to the challenge has been identified as the
2,4-methoxy -3-hydroxy-9-O-beta-D-glucosyloxydibenzofuran by UV, mass
spectrometry, H-1-nuclear magnetic resonance (NMR), and C-13-NMR spec
troscopy. We suggest the trivial name malusfuran for the compound. Mal
usfuran production was initiated approximately 24 h after being challe
nged. Malusfuran inhibited spore germination and growth of Venturia in
aequalis at millimolar concentrations, indicating its role as a possib
le phytoalexin. The aglycone of malusfuran, 2,4-methoxy-3,9-hydroxy-di
benzofuran, showed higher toxicity to V. inaequalis than to the parent
malusfuran. In vitro cultures of V. inaequalis produced a beta-glucos
idase that hydrolyzed ortho- and para-substituted nitrophenyl-beta-glu
cosides, suggesting that the aglycone may act as the actual phytoalexi
n.