T. Kokubun et Jb. Harborne, PHYTOALEXIN INDUCTION IN THE SAPWOOD OF PLANTS OF THE MALOIDEAE (ROSACEAE) - BIPHENYLS OR DIBENZOFURANS, Phytochemistry, 40(6), 1995, pp. 1649-1654
Following fungal inoculation or natural infection, five biphenyl phyto
alexins (aucuparin and its 2' and 4' oxygenated derivatives) were indu
ced variously in the sapwood of Aronia, Chaenomeles, Eriobotrya, Malus
(three spp.) and of Sorbus aucuparia. By contrast, 14 dibenzofuran ph
ytoalexins were induced variously in sapwood of Cotoneaster (7 spp.),
Crateagus, Cydonia, Mespilus, Photinia, Pseudocydonia, Pyracantha, Pyr
us and two Sorbus spp. (S. chamaemespilum and S. domestica). These wer
e five cotonefurans, three eriobofurans, five pyrufurans and a 2,3,4,7
,8-pentaoxygenated dibenzofuran trimethyl ether. No plant has yet been
found to produce both types of phytoalexin, although o-hydroxybipheny
ls are theoretically precursors of the dibenzofurans. The ability to s
ynthesize either biphenyls or dibenzofurans appears to be genus-specfi
c, except in the case of Sorbus. In 18 of the 38 species tested, these
phytoalexins were accompanied by constitutive antifungal phenolics, m
ost of which appeared to be released from bound (glycosidic) forms dur
ing the infection process. These were identified variously as hydroqui
none, p-hydroxyacetophenone, acetovanillone, 5,7-dihydroxychromone, ch
rysin, sakuranetin and naringenin. Woody members of the subfamilies Pr
unoideae and Spiraeoideae failed to yield any phytoalexins on inductio
n, but did contain constitutive antifungal compounds. The limited freq
uency of the phytoalexin response within the family as a whole is cons
idered in relation to the accumulation of constitutive antifungal agen
ts in these plants.