Localization of ferruginol, a diterpene phenol, in Cryptomeria japonica heartwood by time-of-flight secondary ion mass spectrometry

Abstract

Time-of-flight secondary ion mass spectrometry (TOF-SIMS) was applied to the investigation of heartwood extractives in Sugi (Cryptomeria japonica). Sugi heartwood tissue generated secondary ions that were not produced from sapwood tissue by TOF-SIMS. Among the peculiar ions generated from heartwood, two positive ions of m/z 285 and 301 were remarkable due to their appearance in a larger mass range and with a high intensity. These two ions were not generated from heartwood tissue preextracted with n-hexane, and the nhexane extract of Sugi heartwood produced both ions. Gas chromatography-mass spectrometry of the n-hexane extract demonstrated that ferruginol, a diterpene phenol, the molecular weight of which is 286, constituted one of the predominant constituents of the extract. Authentic ferruginol also generated both ions by TOF-SIMS. The molecular formula of the m/z 285 ion generated from Sugi heartwood tissue was estimated to be C 20 H 29 O, which corresponds well with that of ferruginol, i.e. C 20 H 30 O, by peak identification. All these results strongly suggest that the m/z 285 ion generated from Sugi heartwood tissue originated significantly from ferruginol in Sugi heartwood. By TOF-SIMS imaging, the m/z 285 ion was detected uniformly in the tracheid cell walls, in the cell walls of the axial parenchyma cells and ray parenchyma cells, and also inside these parenchyma cells. These results indicate that ferruginol was distributed almost evenly in Sugi heartwood tissue.

Differences in patterns of cell death between ray parenchyma cells and ray tracheids in the conifers Pinus densiflora and Pinus rigida

“…This observation indicates that ray tracheids are not involved in the synthesis of polyphenols during the process of cell death. In contrast, ray parenchyma cells synthesize heartwood extractives, such as polyphenols, prior to their death (Imai et al 2005;Nobuchi and Harada 1985). In the present study, potassium permanganate strongly stained the ray parenchyma cells that were not in contact with ray tracheids in the 31st and 32nd annual rings from the cambium in Pinus densiflora and from the 19th to the 21st annual ring from the cambium in Pinus rigida (Fig.…”

Direct profiling and imaging of plant metabolites in intact tissues by using colloidal graphite‐assisted laser desorption ionization mass spectrometry

“…Recently, localization of phenolic compounds from wood stems has been examined by time-of-flight (TOF) SIMS (Imai et al, 2005;Saito et al, 2008). However, most studies by LDI MS imaging have been done on animal tissue sections such as rat brain slices.…”

A Quinone Isolated from the Nest of Vespa simillima and Its Growth-Inhibitory Effect on Rat Liver Cancer Cells

“…18) In these woods, a variety of biologically active abietane-type and two pimarane-type diterpenoids have been isolated. [22][23][24][25][26][27][28][29][30][31] These reports are indicative that yellow hornets utilize these woods not only for building material for the nest but also as a chemical tool to protect the nest from microorganisms.…”

“…[22][23][24][25][26][27][28][29][30][31] However, these molecular mechanisms have not been well examined. Ross reported that an anticancer quinone classified as an abietane terpenoid exhibited apoptosis, based on morphological changes in the cancer cells.…”