Terpenoids of the Heartwood of Chamaecyparis Nootkatensis

Two monoterpenes and two sesquiterpene diols were isolated and identified for the first time from the methanol extract of the heartwood of Alaska yellow cedar (AYC) tree. The two monoterpenes were identified as (1S)-2-oxo-3-p-menthenol (1) and (4R)-4-hydroxy-4-isopropylcyclohex-1-enecarboxylic acid (2). The two sesquiterpenes were identified as (5S, 7R, 10R, 11R)-eudesm-4(14)-ene-11, 12-diol (kudtdiol, 3) and (4R, 5S, 7R)-1(10)-eremophilene- 11,12-diol (tedonodiol, 4). Structures for these compounds were confirmed on the basis of spectroscopic data and in comparison with related known compounds. In addition, 10 other previously known AYC constituents were also isolated from the methanol extract of the heartwood of AYC including nootkatin, chamic acid, chaminic acid, carvacrol, methyl carvacrol, chanootin, nootkatene, nootkatone, valencene and valencene-13-ol.