Identification of Thuja occidentalis lignans and its biosynthetic relationship
1999
Kawai, S. | Sugishita, K. | Ohashi, H.
Five lignans, (8R,8'R)-(-)-matairesinol, (8R,8'R)-(-)-thujaplicatin methyl ether, (8S,8'S)-(-)-wikstromol, 8-hydroxy-thujaplicatin methyl ether and epi-pinoresinol were isolated from Thuja occidentalis branch xylem, besides the previously identified (8R,8'R)-(-)-4-O-demethylyatein. Chiral HPLC analyses of matairesinol, thujaplicatin methyl ether, wikstromol and 4-O-demethylyatein indicated that these compounds were optically pure. A neolignan, dihydrodehydrodiconiferyl alcohol, was isolated from the acid-hydrolyzed extracts of T. occidentalis leaves. The lignans pinoresinol and secoisolariciresinol were also identified by GC-MS analysis of the extracts of xylem and leaves, respectively. Feeding experiments of [9-(2)H(2), OC(2)H(3)]coniferyl alcohol into T. occidentalis young shoots showed that two molecules of coniferyl alcohol were incorporated into pinoresinol and lariciresinol.
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