OLIGOLIGNANS OF PICEA OBOVATA LEDEB. WOOD
Abstract
The chemical composition of phenolic complex of Siberian Spruce (Picea obovata Ledeb.) wood and the compositions of its oligomeric lignan compounds have been investigated.
The Siberian spruce wood was sampled close to Irkutsk city. The extractives were isolated from grinded wood (particle sizes is 10–15 mm, humidity is 5,9%) by threefold extraction with acetone. The yield of extractives was 1,5% of absolutely dry wood weight (in a.d.w.). The extract was separated by the consecutive extract treatment with the solvents ranged by increasing polarity - hexane, ethyl acetate, n-butanol. The main amount of phenolic compounds (lignans) – was concentrated in ethyl acetate fraction and it was 0,7% in a.d.w..
Ethyl acetate fraction of spruce wood extract was separated by silica gel column using chloroform-acetone mixture as the eluent (with the increase of the latter content in mixture from 0 to 100%). Monomeric lignans (~60–65% of ethyl acetate fraction of spruce wood extract), oligomeric lignans (~20–25%), and polymer lignans (~12–15%) were isolated.
The 13C NMR spectra for the main monomeric, oligomeric and polymeric lignan compounds of phenolic complexes have been recorded. It is found, that the structure of oligomeric and polymeric fractions includes monomeric lignan units with butyrolactone cycle, primarily, the fragments with oxymatairesinol structure. It has been shown, that the fragments with pinoresinol and lariciresinol are presented in oligomeric structures. It is noticed, that all of the monomeric structural units are characterized by guaiacyl substitution type of the aromatic cycles.
A preliminary study of antiviral and antioxidant activity of the ethyl acetate fraction of acetone extract of Siberian spruce wood have been carried out. It is shown, that lignan complex exhibits the activity against Coxsackie B4 virus in cell culture and in pancreatitis model in white mice, reducing the activity of enteroviruses about in 100 times in cell culture. The magnitude of antioxidant activity of polyphenol spruce complex is comparable to those of a known antioxidant dihydroquercetin.
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