Two new diterpenoid acids from Pinus koraiensis
Introduction
Pinus koraiensis is an economically important conifer and is indigenous to the southwest region of China. We have focused our attention on the biologically active compounds of the cones of coniferous trees which have been treated as wastes in the forestry industry and have recently reported volatile oils and diterpenes from the pine cones of Pinaceae [1], [2]. During this investigation two new diterpenoid acids 1 and 2 (PK-A and PK-B) from the EtOAc extract of the cones of P. koraiensis have been isolated. In this paper, the isolation and structural elucidation of these diterpenoids are described.
Section snippets
Generals
UV: Shimadzu UV-260. IR: Perkin Elmer 68. 1H and 13C NMR: Inova-500. EI-MS: Autospec-UltimaETOF.
Plant material
Pinus koraiensis (Pinaceae), cones collected from Heilongjiang province of the People's Republic of China in September 2005 was identified by Professor Wang Zhen-Yu, Northeast Forestry University. The voucher specimen (No. 050916) has been deposited in the Herbarium of School of Food Science and Engineer, Harbin Institute of Technology.
Extraction and purification
The cones of P. koraiensis (4.5 kg) were extracted three times
Results and discussion
Pk-A (1), C20H30O5 M+ at m/z 350.3892 [M]+ (Calc. 350.3903 ) showed the presence of hydroxyl groups (IR max at 3400 cm− 1), an α,β-unsaturated ketone (1695 cm− 1), a trisubstituted double bond (1618 and 831 cm− 1) and a carboxyl group (1718) cm− 1). The 1H and 13C NMR spectrum of 1 (Table 1) revealed signals for two tertiary methyl groups, a hydroxyisopropyl group, six methylenes, two methines, two sp3 quaternary carbons, two tertiary hydroxyl group (δC 72.0 and 74.2 ppm), an α,β-unsaturated ketone
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