Journal
JOURNAL OF WOOD SCIENCE
Volume 47, Issue 6, Pages 476-482Publisher
SPRINGER JAPAN KK
DOI: 10.1007/BF00767901
Keywords
lignan; stereochemistry; Chamaecyparis obtusa; Chamaecyparis obtusa cv. Breviramea; heartwood
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Heartwood of Chamaecyparis obtusa contains significant amounts of a dibenzylbutyrolactone lignan, hinokinin (8). This investigation demonstrated that the contents of 8 and a norlignan, hinokiresinol (12), were higher in the heartwood region than in the sapwood, indicating their nature of being heartwood extractives. Eleven lignans - xanthoxylol (1), 7-oxohinokinin (2), savinin (3), dihydrosesamin (4), isoactifolin (5), sesamin (6), piperitol (7), hinokinin (8), pluviatolide (9), haplomyrfolin (10), and matairesinol (11) - were isolated from young shoots of Chamaecyparis obtusa cv. Breviramea, Fight lignans (1, 2, 4, 5, 7, 9, 10, and 11) were isolated front this plant for the first time. Chiral high-performance liquid chromatographic analysis showed that 8, 9, 10, and It, were found to be levorotatory and optically pure (> 99% e.e.). Based on the chemical structures of the isolated lignans, possible biosynthetic pathways of 8 are discussed.
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