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. 2022 Nov 25;11(12):2338.
doi: 10.3390/antiox11122338.

Comprehensive Characterization of Chemical Composition and Antioxidant Activity of Lignan-Rich Coniferous Knotwood Extractives

Nikolay V Ul'yanovskii  1 , Aleksandra A Onuchina  1 , Anna V Faleva  1 , Natalia S Gorbova  1   2 , Dmitry S Kosyakov  1
Affiliations

Comprehensive Characterization of Chemical Composition and Antioxidant Activity of Lignan-Rich Coniferous Knotwood Extractives

Nikolay V Ul'yanovskii et al. Antioxidants (Basel). .

Abstract

A knotwood of coniferous trees containing large amounts of polyphenolic extractives is considered a promising industrial-scale source of lignans possessing antioxidant properties and other bioactivities. The present study is aimed at a detailed characterization of the chemical composition and antioxidant activity of lignan-rich extractives obtained from the knotwood of the Norway spruce, Scotch pine, Siberian fir, and Siberian larch growing in the European North of Russia as a region with a highly developed forest industry. To achieve this, a comprehensive approach based on a combination of two-dimensional NMR spectroscopy with high-performance liquid chromatography-high-resolution Orbitrap mass spectrometry, and the determination of antioxidant activity by the three complementary methods were proposed. The studied knotwood samples contained from 3.9 to 17% of extractive substances and were comparable to Trolox's antioxidant activity in the single-electron transfer processes and superoxide radical scavenging, which is associated with the predominance of polyphenolic compounds. The latter was represented by 12 tentatively identified monolignans and 27 oligolignans containing 3-5 phenylpropane units in their structure. The extracts were characterized by an identical set of lignans and differed only in the ratios of their individual compounds. Other components of the knotwood were flavonoids taxifolin, quercetin (Siberian larch), and three stilbenes (pinosylvin, its methyl ester, and pterostilbene), which were identified in the Scotch pine extractives. Sesquiterpene juvabione and its derivatives were found in extracts of Siberian larch knotwood.

Keywords: antioxidant activity; coniferous knotwood; extractives; lignans; non-target screening.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Antioxidant activity (AOA) of the knotwood and stemwood extractives determined in amperometric (A), DPPH (B), and PCL (C) assays. The AOA values are represented in gallic acid (GA), ascorbic acid (AA), and Trolox equivalents, respectively.
Figure 2
Figure 2
Two-dimensional (HSQC) 1H-13C NMR spectra of the Picea abies, Pinus sylvestris, Abies sibirica, and Larix sibirica knotwood extractives and cross-peaks assignment.
Figure 3
Figure 3
Structural formulas of the lignans identified in coniferous knotwood extracts.
Figure 4
Figure 4
Tandem mass spectrum of the lignan C20H24O7 identified as olivil.
See this image and copyright information in PMC

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