TY - JOUR
T1 - Elicited cell suspension cultures of apple (Malus x domestica) cv. Liberty produce biphenyl phytoalexins
AU - Borejsza-Wysocki, W.
AU - Lester, C.
AU - Attygalle, A. B.
AU - Hrazdina, G.
PY - 1999/1/26
Y1 - 1999/1/26
N2 - Yeast extract treated cell suspension cultures from a scab (Venturia inaequalis) resistant apple cultivar, Malus x domestica cv. Liberty produce dibenzofuran and biphenyl compounds as part of their defense system against fungal invasion. We have isolated and identified three biphenyl derivatives, 4-hydroxy-3,5-dimethoxybiphenyl (aucuparin), 2',4,-dihydroxy-3,5- dimethoxybiphenyl (2'-hydroxy-aucuparin) and 2'-O-β-D-glucopyranosyl-4- hydroxy-3,5-methoxybiphenyl (2'-o-β-D-glucopyranosylaucuparin) from the cells and the medium and show here their chemical properties. Although this is the first identification of 2'-glucopyranosylaucuparin, its aglycone, 2'- hydroxyaucuparin, and aucuparin have been reported previously [Kokubun, T., Harborne, J.B., Phytochemistry, 1995, 40, 1649-1654.] from fungus infected wood of Malus species. Production of an array of dibenzofuran and biphenyl derivatives in response to fungal attack may be an important part of the disease resistance mechanism of scab resistant apple cultivars.
AB - Yeast extract treated cell suspension cultures from a scab (Venturia inaequalis) resistant apple cultivar, Malus x domestica cv. Liberty produce dibenzofuran and biphenyl compounds as part of their defense system against fungal invasion. We have isolated and identified three biphenyl derivatives, 4-hydroxy-3,5-dimethoxybiphenyl (aucuparin), 2',4,-dihydroxy-3,5- dimethoxybiphenyl (2'-hydroxy-aucuparin) and 2'-O-β-D-glucopyranosyl-4- hydroxy-3,5-methoxybiphenyl (2'-o-β-D-glucopyranosylaucuparin) from the cells and the medium and show here their chemical properties. Although this is the first identification of 2'-glucopyranosylaucuparin, its aglycone, 2'- hydroxyaucuparin, and aucuparin have been reported previously [Kokubun, T., Harborne, J.B., Phytochemistry, 1995, 40, 1649-1654.] from fungus infected wood of Malus species. Production of an array of dibenzofuran and biphenyl derivatives in response to fungal attack may be an important part of the disease resistance mechanism of scab resistant apple cultivars.
KW - 2',4-dihydroxy-3,5-dimethoxybiphenyl
KW - 2'-O-β-D- Glucopyranosyl-4-hydroxy-3,5-dimethoxybiphenyl
KW - 2'-O-β-D- Glucopyranosylacuparin
KW - 2'-hydroxyaucuparin
KW - 4-hydroxy-3,5- dimethoxybiphenyl
KW - Apple
KW - Aucuparin
KW - Biphenyl
KW - Cell suspension
KW - Elicitation
KW - Malus x domestica
KW - Phytoalexin
KW - Rosaceae
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UR - http://www.scopus.com/inward/citedby.url?scp=0032894002&partnerID=8YFLogxK
U2 - 10.1016/S0031-9422(98)00509-3
DO - 10.1016/S0031-9422(98)00509-3
M3 - Article
AN - SCOPUS:0032894002
SN - 0031-9422
VL - 50
SP - 231
EP - 235
JO - Phytochemistry
JF - Phytochemistry
IS - 2
ER -