Identification of Thuja occidentalis lignans and its biosynthetic relationship

• Published in: Phytochemistry (Oxford) 1999-05, Vol.51 (2), p.243-247
• Main Authors: Kawai, Shingo, Sugishita, Kazuhiro, Ohashi, Hideo
• Format: Article
• Language: English
• Subjects: 3,5-Dimethoxy-4-hydroxyphenyl group; Agronomy. Soil science and plant productions; Biological and medical sciences; biosynthesis; branches; chemical constituents of plants; chemical structure; Cupressaceae; Economic plant physiology; Fundamental and applied biological sciences. Psychology; Gymnosperm lignin; leaves; Lignan biosynthesis; lignans; lignin; Metabolism; Metabolism. Physicochemical requirements; Nitrogen metabolism and other ones (excepting carbon metabolism); Nutrition. Photosynthesis. Respiration. Metabolism; Plant physiology and development; shoots; Stereochemistry; Thuja occidentalis; xylem
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/S0031-9422(99)00004-7

Five lignans, (8 R,8′ R)-(−)-matairesinol, (8 R,8′ R)-(−)-thujaplicatin methyl ether, (8 S,8′ S)-(−)-wikstromol, 8-hydroxy-thujaplicatin methyl ether and epi-pinoresinol were isolated from Thuja occidentalis branch xylem, besides the previously identified (8 R,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 2H 3]coniferyl alcohol into T. occidentalis young shoots showed that two molecules of coniferyl alcohol were incorporated into pinoresinol and lariciresinol.