Search Results (7)

The current work represents a comparative study of the phenolic profiles of three under-explored Onosma (Boraginaceae) species from Greece—Onosma leptantha (OL), Onosma erecta (OE), and Onosma graeca (OG). Although Onosma spp. have ethnopharmacological significance, previous phytochemical studies have focused primarily on roots. Methanolic extracts of the aerial parts were analyzed using qualitative LC-MS enhanced by molecular networking-based dereplication, annotating 94 phenolics categorized into hydroxybenzoic acids (7), hydroxycinnamic acids (24), lignans (14), neolignans (14), stilbenes (4), coumarins (5), and flavonoids (26). OG exhibited the broadest distribution of flavonoid glycosides. OL contained the greatest number of hydroxycinnamic and neolignan derivatives, and OE was notably abundant in lignans. Total phenolic (TPC) and total flavonoid (TFC) contents were quantified, and the antioxidant capacity and enzyme inhibition against cholinesterases, α-amylase, and α-glucosidase were assessed. OL showed a high TPC (69.03 mg GAE/g extract) and strong antioxidant activity, while OG exhibited a high TFC (45.80 mg RE/g extract). All extracts demonstrated stronger AChE inhibition than BChE, with OG showing the highest AChE inhibition (2.35 mg GALAE/g). Additionally, OL was the most active against both α-glucosidase (5.69 mmol ACAE/g) and α-amylase (0.48 mmol ACAE/g). This study improved our understanding of the chemical diversity within these species, providing a more comprehensive insight into their longstanding ethnopharmacological potential. Full article

In our preliminary study, a hot water extract from the fruits of Morus alba (mulberry) inhibited the secretion of metalloproteinase-1 (MMP-1) against tumor necrosis factor-α (TNF-α)-stimulated human dermal fibroblasts (HDFs), and therefore we researched its active compounds. In the present study, a new phenolic glycoside (oddioside A, 1) and 21 known compounds (2−22) were isolated from the hot water extract from the fruits of M. alba by repeated chromatography. The chemical structure of the new compound 1 was elucidated by its spectroscopic data (1D− and 2D−NMR and HRMS) measurement and by acidic hydrolysis. The presence of sargentodoside E (2), eugenyl glucoside (6), 2-O-β-d-glucopyranosyl-4,6-dihydroxybenzaldehyde (7), 7S,8R-erythro-7,9,9’-trihydroxy-3,3’-dimethoxy-8-O-4’-neolignan-4-O-β-d-glucopyranoside (11), pinoresinol-4-O-β-d-glucopyranoside (12), taxifolin-7-O-β-d-glucopyranoside (20), and pinellic acid (21) were reported from M. alba for the first time in this study. The new compound oddioside A (1) suppressed the secretion of MMP-1 and increased collagen in TNF-α-stimulated HDFs. In addition, the phosphorylation of mitogen-activated protein kinases (MAPKs) was inhibited by oddioside A. In conclusion, the extract from fruits of M. alba and its constituent oddioside A may be a potential agent to prevent inflammation-related skin aging and other skin disorders. Full article

In vitro culture of flax (Linum usitatissimum L.) was exposed to chitosan oligosaccharides (COS) in order to investigate the effects on the growth and secondary metabolites content in roots and shoots. COS are fragments of chitosan released from the fungal cell wall during plant–pathogen interactions. They can be perceived by the plant as pathogen-associated signals, mediating local and systemic innate immune responses. In the present study, we report a novel COS oligosaccharide fraction with a degree of polymerization (DP) range of 2–10, which was produced from fungal chitosan by a thermal degradation method and purified by an alcohol-precipitation process. COS was dissolved in hydroponic medium at two different concentrations (250 and 500 mg/L) and applied to the roots of growing flax seedlings. Our observations indicated that the growth of roots and shoots decreased markedly in COS-treated flax seedlings compared to the control. In addition, the results of a metabolomics analysis showed that COS treatment induced the accumulation of (neo)lignans locally at roots, flavones luteolin C-glycosides, and chlorogenic acid in systemic responses in the shoots of flax seedlings. These phenolic compounds have been previously reported to exhibit a strong antioxidant and antimicrobial activities. COS oligosaccharides, under the conditions applied in this study (high dose treatment with a much longer exposure time), can be used to indirectly trigger metabolic response modifications in planta, especially secondary metabolism, because during fungal pathogen attack, COS oligosaccharides are among the signals exchanged between the pathogen and host plant. Full article

In vitro cultures of scarlet flax (Linum grandiflorum L.), an important ornamental flax, have been established as a new possible valuable resource of lignans and neolignans for antioxidant and anti-inflammatory applications. The callogenic potential at different concentrations of α-naphthalene acetic acid (NAA) and thidiazuron (TDZ), alone or in combinations, was evaluated using both L. grandiflorum hypocotyl and cotyledon explants. A higher callus induction frequency was observed on NAA than TDZ, especially for hypocotyl explants, with a maximum frequency (i.e., 95.2%) on 1.0 mg/L of NAA. The presence of NAA (1.0 mg/L) in conjunction with TDZ tended to increase the frequency of callogenesis relative to TDZ alone, but never reached the values observed with NAA alone, thereby indicating the lack of synergy between these two plant growth regulators (PGRs). Similarly, in terms of biomass, NAA was more effective than TDZ, with a maximum accumulation of biomass registered for medium supplemented with 1.0 mg/L of NAA using hypocotyls as initial explants (DW: 13.1 g). However, for biomass, a synergy between the two PGRs was observed, particularly for cotyledon-derived explants and for the lowest concentrations of TDZ. The influence of these two PGRs on callogenesis and biomass is discussed. The HPLC analysis confirmed the presence of lignans (secoisolariciresinol (SECO) and lariciresinol (LARI) and neolignan (dehydrodiconiferyl alcohol [DCA]) naturally accumulated in their glycoside forms. Furthermore, the antioxidant activities performed for both hypocotyl- and cotyledon-derived cultures were also found maximal (DPPH: 89.5%, FRAP 866: µM TEAC, ABTS: 456 µM TEAC) in hypocotyl-derived callus cultures as compared with callus obtained from cotyledon explants. Moreover, the anti-inflammatory activities revealed high inhibition (COX-1: 47.4% and COX-2: 51.1%) for extract of hypocotyl-derived callus cultures at 2.5 mg/L TDZ. The anti-inflammatory action against COX-1 and COX-2 was supported by the IC₅₀ values. This report provides a viable approach for enhanced biomass accumulation and efficient production of (neo)lignans in L. grandiflorum callus cultures. Full article

This study aimed to identify and quantify phenolic and resin acid extractive compounds in Scots pine stemwood and sawmill residues in four climatic regions of Finland to evaluate their most optimal sources for bio-based chemical biorefining and bioenergy products. The sample consisted of 140 trees from 28 stands, and sawdust lots from 11 log stands. NMR for the overall extractive analysis and HPLC for the quantitative estimation of phenolic and resin acid compounds were employed. Correlation analysis, multivariate factor analysis, principle component analysis and multiple linear regression modelling were applied for statistical analysis. HPLC identified 12 extractive compounds and NMR five more resin acids. Pinosylvin (PS), pinosylvin monomethyl ether (PSMME), and partly neolignans/lignans occurred in the largest concentrations. Wood type caused the most variation, heartwood having larger concentrations than sapwood (sawdust between them). Regional differences in the concentrations were smaller, but factor analysis distinguished the northern and the southern regions into their own groups. The results indicated higher concentrations of PS, PSMME, and vanillic acid in southern regions and those of, e.g., PSMME glycoside, lignan 2, and neolignan 1 in northern regions. The rather low concentrations of extractives in stemwood and sawdust imply value-added products, efficient sorting and/or large raw material volumes. Full article

A new neolignan glycoside, (7R,8R)-7,8-dihydro-9′-hydroxyl-3′-methoxyl- 8-hydroxymethyl-7-(4-hydroxy-3-methoxyphenyl)-1′-benzofuranpropanol 9′-O-β-D- glucopyranoside (1) was isolated from the leaves of Acer truncatum along with (7R,8R)-7,8-dihydro-9′-hydroxyl-3′-methoxyl-8-hydroxymethyl-7-(4-O-α-L-rhamno- pyranosyloxy-3-methoxyphenyl)-1′-benzofuranpropanol (2), schizandriside (3), lyoniresinol (4), berchemol (5), (-)-pinoresinol-4-O-β-D-glucopyranoside (6), hecogenin (7), chlorogenic acid (8) and neochlorogenic acid (9). Their structures were elucidated on the basis of extensive spectroscopic data. The absolute configuration of compounds 1 was established by its CD spectrum. The antibacterial activities of compounds 1-7 were evaluated. Full article