ABSTRACT
Lignin and lignans share monolignols as common precursors and are both potentially involved in plant defence against pathogens. In this study, we investigated the effects of fungal elicitors on lignin and lignan metabolism in flax (Linum usitatissimum) cell suspensions. Cell suspension cultures of flax were treated with elicitor preparations made from mycelium extracts of Botrytis cinerea, Phoma exigua and Fusarium oxysporum F ssp lini. Elicitors induced a rapid stimulation of the monolignol pathway, as confirmed by the increase in PAL (phenylalanine ammonia-lyase, EC 4.1.3.5), CCR (cinnamoyl-CoA reductase EC 1.2.1.44) and CAD (cinnamyl alcohol dehydrogenase EC 1.1.1.195) gene expression and PAL activity. At the same time, CCR activity only increased significantly in F. oxysporum-treated cells 24 h post elicitation. On the other hand, CAD activity measured for coniferyl alcohol formation was transiently decreased but a substrate-specific activation of CAD activity was observed in F. oxysporum-treated cells when using sinapyl alcohol as substrate. The accumulation of monolignol-derived products varied according to the elicitor used. B. cinerea or P. exigua-elicited cell cultures were characterised by a reinforcement of the cell wall by a deposit of 8-O-4'-linked non-condensed lignin structures and phenolic monomers, while at the same time no stimulation of 8-8'-linked lignan or 8-5'-linked phenylcoumaran lignan accumulation was observed. Additionally, elicitation of cell cultures with F. oxysporum extracts even triggered a strong incorporation of monolignols in the non condensed labile ether-linked lignin fraction concomitantly with a decrease in lignan and phenylcoumaran lignan accumulation. Several hypotheses are proposed to explain the putative role of these compounds in the defence response of flax cells against pathogens.
Subject(s)
Biological Factors/pharmacology , Coumaric Acids/metabolism , Flax/metabolism , Lignans/metabolism , Lignin/metabolism , Ascomycota/chemistry , Ascomycota/physiology , Botrytis/chemistry , Botrytis/physiology , Butylene Glycols/metabolism , Cell Wall/metabolism , Cells, Cultured , Flax/drug effects , Flax/microbiology , Fusarium/chemistry , Fusarium/physiology , Glucosides/metabolism , Lignans/biosynthesis , Mycelium/chemistry , Phenols/metabolism , Spectroscopy, Fourier Transform InfraredABSTRACT
The opening of ortho-substituted phenyl oxiranes by borohydrides is described both in aqueous and solid phases. Some remarkable differences in the regioselectivity and inversion of enantioselectivity of oxirane ring-opening are reported. The results obtained are compared with previous studies and have allowed some factors governing the reactivity, the regio- and stereoselectivity of this reaction to be evaluated. Preferential orientations of the substrate included inside the cyclodextrin are proposed from these results. Copyright 1999 Wiley-Liss, Inc.
