Coniferin dimerisation in lignan biosynthesis in flax cells.
[(13)C(2)]-Coniferin was provided to a flax (Linum usitatissimum L.) cell suspension to monitor subsequent dimerisation by MS and NMR. The label was mainly incorporated into a 8-8'-linked lignan, lariciresinol diglucoside, a 8-5'-linked neolignan, dehydrodiconiferyl alcohol glucoside and a diastereoisomeric mixture of a 8-O-4'-linked neolignan, guaiacylglycerol-beta-coniferyl alcohol ether glucoside. This latter compound is reported for the first time in flax. The strong and transient increase in these compounds in fed cells was concomitant with the observed peak in coniferin content. These results suggest (i) a rapid metabolisation of coniferin into lignans and neolignans and indicate the capacity of flax cells to operate different types of couplings, and (ii) a continuous synthesis and subsequent metabolisation of coniferin-derived dimers all over the culture period.
Beejmohun
Vickram
V
Laboratoire de Phytotechnologie EA 3900, Faculté de Pharmacie, Université de Picardie Jules Verne, 1 Rue des Louvels, 80037 Amiens, France.
Fliniaux
Ophélie
O
Hano
Christophe
C
Pilard
Serge
S
Grand
Eric
E
Lesur
David
D
Cailleu
Dominique
D
Lamblin
Frédéric
F
Lainé
Eric
E
Kovensky
José
J
Fliniaux
Marc-André
MA
Mesnard
François
F
D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000737:chemistry* / Q000378:metabolism*; D019281:Dimerization; D019597:Flax / Q000737:chemistry* / Q000378:metabolism*; D007700:Kinetics; D017705:Lignans / Q000096:biosynthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D021241:Spectrometry, Mass, Electrospray Ionization
D002934:Cinnamates; D017705:Lignans; C016316:coniferin