3310-97-2Relevant academic research and scientific papers
Synthesis and characterization of abietadiene, levopimaradiene, palustradiene, and neoabietadiene: Hydrocarbon precursors of the abietane diterpene resin acids
Lee, Hyung-Jae,Ravn, Matthew M.,Coates, Robert M.
, p. 6155 - 6167 (2007/10/03)
The abietane diterpenes - abietadiene, levopimaradiene, palustradiene, and neoabietadiene (1b-4b) - were prepared from the corresponding resin acids by diazomethane esterifications, LiAlH4 reductions, tosylations, and Zn/NaI reductions. Abietadiene was also obtained less efficiently by catechol borane reduction of abietadienal tosylhydrazone and Li/NH3 reduction of its 18-phenylthio derivative. These conjugated dienes were characterized by chromatographic properties (HPLC, TLC, GC), MS fragmentation patterns, optical rotations, and UV, IR, 1H NMR, and 13C NMR data. Assignments for the 1H and 13C NMR spectra were made by COSY, DEPT, HMQC, HMBC, NOE data, H-H coupling analysis, and comparisons with literature data. The four diterpenes were identified as cyclization products of recombinant abietadiene synthase, supporting their likely role in the biosynthesis of the abietane resin acids in conifer oleoresin.
Labdane acids and other components of the needles of Pinus pumila
Raldugin, V. A.,Demenkova, L. I.,Pentegova, V. A.
, p. 192 - 197 (2007/10/02)
The terpenoid and aliphatic components of an ethereal extract of the oleoresin of the Japanese stone pine have been investigated.Among them, 33 compounds have been identified, ten of which were isolated in the individual state.The labdane acids of the oleoresin investigated were represented by 19-O-succinylagatholic and 3β-hydroxy-, 3β-acetoxy, and 3-ketoanticopalic acids.
