Oligolignans in the wood of Picea obovata Ledeb.

Resumo

We studied the chemical composition of the phenolic complex and the structure of oligomeric lignans in Siberian spruce (Picea obovata Ledeb.). We used the wood of Siberian spruce collected near the city of Irkutsk. The extractives were isolated from ground wood (particle size: 10–15 mm; humidity: 5.9%) by three-stage acetone extraction. The extract was separated by consecutive treatment with the solvents with increasing polarity: hexane, ethyl acetate and n-butanol. The main amount of phenolic compounds (lignans) was concentrated in the ethyl acetate fraction and it was 0.7% in absolutely dry wood (adw).

The ethyl acetate fraction of spruce wood extract was separated by silica gel column; a chloroform-acetone mixture was used as the eluent (the concentration of acetone in the mixture was increased from 0 to 100%). Monomeric lignans (~60–65% of the ethyl acetate fraction of spruce wood extract), oligomeric lignans (~20–25%), and polymer lignans (~12–15%) were isolated.

We also obtained ¹³C nuclear magnetic resonance (NMR) spectra for the main monomeric, oligomeric and polymeric lignan compounds of phenolic complexes. It was found that oligomeric and polymeric fractions contain monomeric lignan units with the butyrolactone cycle, primarily, the fragments with hydroxymatairesinol structure. Oligomeric lignans contain the fragments with a pinoresinol and lariciresinol structure. All the monomeric structural units are characterized by the guaiacyl substitution type of the aromatic cycles.

A preliminary study has been performed on the antiviral and antioxidant activity of the ethyl acetate fraction of acetone extract of Siberian spruce wood. It was found that the lignan complex is active against Coxsackie B4 virus in cell culture and in the pancreatitis model in white mice, reducing the activity of enteroviruses in the cell culture approximately 100 times. The antioxidant activity rate of polyphenol complex of Siberian spruce wood is comparable to that of a known antioxidant dihydroquercetin.