Induction of the biosynthesis of agatharesinol, a norlignan, in sapwood sticks of Cryptomeria japonica under humidity-regulated circumstances

To establish an experimental approach for studying the biosynthetic pathway of agatharesinol, a norlignan, induction of the formation of agatharesinol in Cryptomeria japonica (Japanese cedar, sugi) was attempted. Wood sticks were prepared from the sapwood immediately after cutting a sugi tree down, and they were allowed to stand in desiccators in which the humidity was adjusted to 76% and 88%, and in a room. When the wood sticks were allowed to stand in 76% humidity and in a room, they dried rapidly and no formation of agatharesinol was demonstrated by gas chromatography-mass spectrometry. These results suggest that in the sapwood dried rapidly, the cells that were biologically active in the sapwood, probably ray parenchyma cells, die rapidly and completely before the biosyntheses of secondary metabolites including agatharesinol was wholly established. The wood sticks allowed to stand in 88% humidity, on the other hand, dried gradually compared with the sticks placed in 76% humidity and in a room, and agatharesinol was formed as one of the predominant ethyl acetate extractives. These results suggest that delaying the drying of the sapwood sticks can control the dying period to an appropriate length for the ray parenchyma cells, during which the biosynthesis of agatharesinol is induced. Part of this study was presented at the 54th Annual Meeting of the Japan Wood Research Society, Sapporo, August 2004     

Studies on the immunolabeling of heartwood extractives: characterization of anti-agatharesinol antiserum

The reactivity of previously prepared antiserum against agatharesinol, a norlignan, was determined by competitive inhibition–ELISA (enzyme-linked immunosorbent assay) using several natural compounds that are representative of plant extractives as competitive inhibitors. The antiserum strongly reacted with some norlignans (i.e., agatharesinol, hinokiresinol, and metasequirin C), each of which has a common chemical-structural unit. This result suggests that the antiserum recognizes the specific chemical-structural unit composing those norlignans. Moreover, differences in the reactivities of the antiserum with agatharesinol derivatives and synthetic chalcones propose the trans-3-p-hydroxyphenyl-1-phenylpropene structural unit as the major antigenic determinant for the antiserum.Part of this paper was presented at the 45th Lignin Symposium, Matsuyama, October 2000 and the 51th Annual Meeting of the Japan Wood Research Society, Tokyo, April 2001