Amounts Of Lignans Research Articles

Patterns and roles of lignan and terpenoid accumulation in the reaction zone compartmentalizing pathogen-infected heartwood of Norway spruce

Main conclusionLignan impregnation of the reaction zone wood protects against oxidative degradation by fungi. Traumatic resin canals may play roles in the underlying signal transduction, synthesis, and translocation of defense compounds.Tree defense against xylem pathogens involves both constitutive and induced phenylpropanoids and terpenoids. The induced defenses include compartmentalization of compromised wood with a reaction zone (RZ) characterized by polyphenol deposition, whereas the role of terpenoids has remained poorly understood. To further elucidate the tree–pathogen interaction, we profiled spatial patterns in lignan (low-molecular-weight polyphenols) and terpenoid content in Norway spruce (Picea abies) trees showing heartwood colonization by the pathogenic white-rot fungus Heterobasidion parviporum. There was pronounced variation in the amount and composition of lignans between different xylem tissue zones of diseased and healthy trees. Intact RZ at basal stem regions, where colonization is the oldest, showed the highest level and diversity of these compounds. The antioxidant properties of lignans obviously hinder oxidative degradation of wood: RZ with lignans removed by extraction showed significantly higher mass loss than unextracted RZ when subjected to Fenton degradation. The reduced diversity and amount of lignans in pathogen-compromised RZ and decaying heartwood in comparison to intact RZ and healthy heartwood suggest that α-conindendrin isomer is an intermediate metabolite in lignan decomposition by H. parviporum. Diterpenes and diterpene alcohols constituted above 90% of the terpenes detected in sapwood of healthy and diseased trees. A significant finding was that traumatic resin canals, predominated by monoterpenes, were commonly associated with RZ. The findings clarify the roles and fate of lignan during wood decay and raise questions about the potential roles of terpenoids in signal transduction, synthesis, and translocation of defense compounds upon wood compartmentalization against decay fungi.

Lignans dramatically enhance the resistance of Fraxinus velutina Torr. by adjusting the dominant bacterium group of Agrilus planipennis Fairmaire

Velvet ash (Fraxinus velutina Torr.) is an important wood and ornamental tree species. Emerald ash borer (EAB), Agrilus planipennis Fairmaire, is a major wood borer of velvet ash. The aim of this study was to identify the secondary metabolites of velvet ash involved in regulating the dominant bacterium group of EAB. The amount of lignans in the phloem of infested trees had increased by 290.96% because of A. planipennis infection. The addition of lignans to the artificial diet significantly reduced the weight of the larvae and decreased the dominant bacterial group in the larval midgut, such as Pseudomonadaceae, Xanthomonadaceae, and Enterobacteriaceae. The FvPLR1, a key gene for lignan synthesis, was obtained based on the phloem transcriptome of velvet ash. The expression of FvPLR1 in the phloem of the infested tree was significantly higher than that in the noninfested tree. Meanwhile, FvPLR1 silenced by virus-induced gene silencing showed that its expression level and the lignan content were decreased by 69.91% and 31.65%, respectively. Interestingly, silencing FvPLR1 induced alterations in the dominant bacteria group in the larvae, with the reverse trend in the lignan-fed treatment. The evidence showed that FvPLR1 was a positive regulator. The increasing synthesis of lignans leads to resistance improvement in velvet ash, which will provide comprehensive insights into the tree defense system to wood borer infestation. © 2021 Society of Chemical Industry.

Lignans in triticale grain and triticale products

This study determined the lignan content of seven varieties of triticale grain and compared these values with wheat and rye grain, with triticale milling fractions (bran, shorts, and refined flour), and triticale products (sprouted grain, malt, fermented bread dough, baked dough, dried pasta and cooked pasta). Acid hydrolysis and enzymatic hydrolysis were used to release the lignans in extracts. We carried out qualitative and quantitative analysis of secoisolariciresinol, matairesinol, lariciresinol, syringaresinol, and pinoresinol levels using an Acquity UPLC liquid chromatograph with photodiode and mass Acquity TQD detectors. The most abundant lignan in all samples was syringaresinol, which made up 80% of all lignans. The lignan content of triticale grain varied from 392 to 792 μg·100gd·m−1 (acid hydrolysis) and from 685 to 1189 μg·100gd·m−1(enzymatic hydrolysis), depending on the variety. The lignan levels in triticale bran were almost three times those found in the grain; in flour, there was one fifth or even one tenth as much, whereas the shorts had similar levels as the grain. After three days of germination, the amount of lignans in the triticale grain increased by 17%–32%. A greater increase in lignan content (by factors of 1.4 and 2.3) was found in triticale after extrusion cooking. Fermentation led to lignan concentrations increasing slightly (2–14%), but this was then reduced in the baking process. Extracts from dry pasta contained similar or lower amounts than did the raw material, but the concentration was higher in cooked pasta (14%–47%). The enzymatic hydrolyzed extracts contained on average 36% higher lignan content than did the acid hydrolyzed samples.

STUDY ON ACTIVE INGREDIENTS OF LIGNANS FROM SCHISANDRA CHINENSIS BASED ON HOLLOW FIBER LIQUID PHASE MICROEXTRACTION

Hollow fiber liquid phase microextraction combined with high performance liquid chromatography (HFLPME with HPLC) is a simple, rapid, and sensitive method for the study on the pharmacokinetics of the active ingredients of lignans (i.e., schisandrol A, schisantherin A, schizandrin A, schizandrin B, and schizandrin C) from Schisandra chinensis after oral administration to rats. Several important HFLPME parameters, such as type of hollow fiber and extraction solvent, pH of sample phase, ionic strength, centrifugation speed, extraction time, and sample volume, were carefully investigated and optimized. Under optimal conditions, the enrichment factors for the five lignans in urine and plasma were within the ranges from 42.7 to 99.5 and 42.3 to 189.0, respectively. The linear ranges, limits of detection and quantification, precisions, and the mean recoveries and stabilities were satisfactory during the determination of five lignans in urine and plasma. The pharmacokinetics of five lignans was simultaneously studied in rats following intragastric administration of S. chinensis; the pharmacokinetic parameters were also estimated. The validated HFLPME with HPLC is suitable for the preconcentration and determination of trace amount of lignans in biological fluid. The method can also be used in research on the pharmacokinetics of active constituents in traditional Chinese medicines.

Lignan Content of the Flaxseed Influences Its Biological Effects in Healthy Men and Women

Objective: The omega-3 polyunsaturated fatty acid (n-3 PUFA) as well as lignan components of flaxseed (FLX) can have beneficial effects. In this 6-week-long, randomized, double-blinded, placebo-controlled study, we investigated the effects of FLX lignans on cardiovascular risk factors. Methods: Thirty-seven subjects (13 men and 24 women, age: 54 ± 7 years, body mass index [BMI]: 29.7 ± 1 kg/m2) consumed nutrition bars with similar macronutrient contents. The fatty acid composition and the lignan contents of the bars differed significantly. Two FLX bars both contained 3.0 g of alpha linolenic acid (ALA: 18:3 n-3) but different amount of lignans (0.15 g vs. 0.41 g). Results: High-lignan FLX decreased total cholesterol (C) by 12% (p = 0.044), LDL-C by 15% (p = 0.022), and oxidized (Ox)-LDL by 25% (p = 0.035). Regular FLX tended to increase Ox-LDL by 13% (p = 0.051). The difference between the effects of high-lignan vs. regular lignan FLX on Ox-LDL was highly significant (p = 0.004). Conclusion: High-lignan FLX has the unique property of decreasing Ox-LDL, which is an independent risk factor for cardiovascular disease.

Lignan Content in Cereals, Buckwheat and Derived Foods.

Cereal foods are a fundamental part of a balanced diet and several studies have assigned to wholemeal cereal products a protective role in human health, due to their content of bioactive compounds. Within the phytochemicals, lignans are of increasing interest for their potential anticarcinogenic, antioxidant, estrogenic and antiestrogenic activities. The aim of this work is to contribute to the updating of food lignan databases by providing the profile and the amount of lignans in cereals, buckwheat and several cereal based foods commonly consumed in human diets. Values were taken from published papers. Items were divided in different groups, namely grains, brans and flours, bread, cereal staple foods, breakfast cereals and other cereal products, and values for secoisolariciresinol, matairesinol, pinoresinol, lariciresinol are given. For example, the total average values for the mentioned lignans in grains ranged between 23 μg/100 g and 401 μg/100 g dry weight. The contribution of each single lignan molecule to the total value of lignans appears to be different for every cereal species. Lignan content and typology in processed foods depends on the raw materials used, their degree of refinement and on processing conditions.

Seasonal Alteration in Amounts of Lignans and Their Glucosides and Gene Expression of the Relevant Biosynthetic Enzymes in the <i>Forsythia suspense</i> Leaf

Lignans of Forsythia spp. are essential components of various Chinese medicines and health diets. However, the seasonal alteration in lignan amounts and the gene expression profile of lignan-biosynthetic enzymes has yet to be investigated. In this study, we have assessed seasonal alteration in amounts of major lignans, such as pinoresinol, matairesinol, and arctigenin, and examined the gene expression profile of pinoresinol/lariciresinol reductase (PLR), pinoresinol-glucosylating enzyme (UGT71A18), and secoisolariciresinol dehydrogenase (SIRD) in the leaf of Forsythia suspense from April to November. All of the lignans in the leaf continuously increased from April to June, reached the maximal level in June, and then decreased. Ninety percent of pinoresinol and matairesinol was converted into glucosides, while approximately 50% of arctigenin was aglycone. PLR was stably expressed from April to August, whereas the PLR expression was not detected from September to November. In contrast, the UGT71A18 expression was found from August to November, but not from April to July. The SIRD expression was prominent from April to May, not detected in June to July, and then increased again from September to November. These expression profiles of the lignan-synthetic enzymes are largely compatible with the alteration in lignan contents. Furthermore, such seasonal lignan profiles are in good agreement with the fact that the Forsythia leaves for Chinese medicinal tea are harvested in June. This is the first report on seasonal alteration in lignans and the relevant biosynthetic enzyme genes in the leaf of Forsythia species.

Production of podophyllotoxin in Linum linearifolium in vitro cultures

For the first time, callus and suspension cultures of Linum linearifolium were initiated. Podophyllotoxin (PTOX), a strong antitumor precursor, was isolated from the calli and suspension, as a main lignan besides smaller amount of 6-methoxypodophyllotoxin (6MPTOX). L. linearifolium is now the third Linum species of section Syllinum, with PTOX as the main lignan. The amounts of lignans, especially PTOX, found in L. linearifolium cell cultures are quite high within the studied Linum species until now. The antiproliferative effects of extracts were tested in a panel of human tumor cell lines, using the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide]-dye reduction assay. The lignan mixtures caused concentration-dependent inhibition of malignant cell proliferation and showed moderate cytotoxic activity. The results clearly demonstrate that the lignan mixture of L. linearifolium exerts inhibitory effects against malignant cells.

Dibenzocyclooctadiene lignan production in Schisandra chinensis embryogenic culture

The quantitative determination of lignans was based on extraction with organic solvents, solid phase extraction and quantitative HPLC analysis (Slanina and Glatz, 2004). Interestingly, we have observed selectivity of absorption of individual lignans from culture media by different polymeric resins. This fact may significantly facilitate the isolation of lignans adsorbed onto resins. The amount of lignans produced by culture increased several time under amberlite influence. According our results, addition of polymeric adsorbents seems to be very useful tool for achievement of lignans of special interest from embryogenic in vitro culture of S. chinensis. Thus lignans acquired (in sufficient amounts and purity) can be subsequently used for more detailed studies of their pharmacological effects, for analytical purposes, or can be utilised in clinical practice.

Lignan contents in sesame seeds and products

AbstractSesame seed (Sesamum indicum L.) is a rich source of furofuran lignans with a wide range of potential biological activities. The major lignans in sesame seeds are the oil‐soluble sesamin and sesamolin, as well as glucosides of sesaminol and sesamolinol that reside in the defatted sesame flour. Upon refining of sesame oil, acid‐catalyzed transformation of sesamin to episesamin and of sesamolin to epimeric sesaminols takes place, making the profile of refined sesame oils different from that of virgin oils. In this study, the total lignan content of 14 sesame seeds ranged between 405 and 1178 mg/100 g and the total lignan content in 14 different products, including tahini, ranged between 11 and 763 mg/100 g. The content of sesamin and sesamolin in ten commercial virgin and roasted sesame oils was in the range of 444–1601 mg/100 g oil. In five refined sesame oils, sesamin ranged between 118 and 401 mg/100 g seed, episesamin between 12 and 206 mg/100 g seed, and the total contents of sesaminol epimers between 5 and 35 mg/100 g seed, and no sesamolin was found. Thus, there is a great variation in the types and amounts of lignans in sesame seeds, seed products and oils. This knowledge is important for nutritionists working on resolving the connection between diet and health. Since the consumption of sesame seed products is increasing steadily in Europe and USA, it is important to include sesame seed lignans in databases and studies pertinent to the nutritional significance of antioxidants and phytoestrogens. It is also important to differentiate between virgin, roasted and refined sesame oils.

Antioxidant activity of polyphenols from the far-east plant Taxus cuspidata

Phenolic components of the wood and roots of far-east yew (Taxus cuspidata) have been isolated and investigated. Four lignans [(+)-taxiresinol, (+)-isotaxiresinol, (+)-isolariciresinol, (−)-secoisolariciresinol] and two catechins [(+)-catechin, (−)-epicatechin] were identified using spectroscopic techniques. HPLC data showed that wood, bark, roots, stems, and needles of the plant contain different amounts of lignans and catechins. The antioxidant and radical-scavenging activities of the polyphenols were evaluated on two in vitro model systems.

Formation of lignans in plant cell culture of Schisandra chinensis

The fruit of Schisandra chinensis, a woody liana, has been used for centuries in traditional Chinese medicine. The fruit is prescribed for the treatment of hepatitis in China. The active principles are lignans with unusual structures derived from dibenzo[a,c]cyclooctadiene. These lignans have been shown to possess a broad range of biological activities. Recently, it has been found that lignan gamma-schizandin strongly inhibits P-glycoprotein, the overexpression of which is the most frequent cause for cancer multidrug resistance. S. chinensis cultures derived from immature zygotic embryos were developed on Murashige and Skoog and VW5 medium. Embryogenic cultures were established on the medium containing thidiazuron, 2,4-dichlorophenoxyacetic acid and benzylaminopurine. An analytical method based on HPLC-UV was used for the determination of six lignans in plant cell cultures. Our previous results showed that the concentration of lignans in plant cell cultures was mostly lower than that in fruit and leaves. We also detected the lignans in liquid culture media, but the amount of lignans inside the cells was substantially higher. In order to release the lignans stored within the cells, we explored the cultivation of five cell lines with neutral polymeric resin, Amberlite XAD2. We found that the addition of Amberlite XAD2 not only notably enlarged portions of extracellular lignans, but also greatly enhanced the production of lignan deoxyschizandrin, whereas the formation of other lignans was increased only moderately (less than 5fold). Importantly, Amberlite XAD-2 did not reduce the growth of cell cultures. Deoxyschizandrin adsorbed on the polymeric resin can be easily recovered and purified without destruction of the cells.

Lignans in selected wines

Wines have been studied a lot and several different groups of phenolic compounds have been analysed in wine samples, but lignans in wines have been only preliminary studied. In this study, we analysed 10 different wines of which eight were red wines and two white wines. Samples were selected among the most consumed wines in Finland in year 1999. Eight different lignans were analysed with HPLC using coulometric electrode array detector. The amount of lignans in red wines ranged from 0.812 to 1.406 mg/l. The main lignan in all studied wines was isolariciresinol and percentage amount of mammalian lignan precursors varied from 34 to 43% in the red wines. The amount of lignans was much lower in the studied white wines compared with the red wines.

Lignans and Lipophilic Extractives in Norway Spruce Knots and Stemwood

Summary The hydrophilic and lipophilic extractives in the heartwood of knots from 7 Norway spruce trees were analysed by GC, GC-MS and HPSEC. The knots contained extremely large amounts of lignans, 6–24% (w/w), with hydroxymatairesinol comprising 65–85% of the lignans. Even the knots of the young trees contained 4–8% (w/w) of lignans. The variation in the amount of lignans was large among knots, both within a single tree and between trees. In addition to the lignans, knots also contained 2–6% (w/w) of a complex mixture of lignan-like compounds with 3, 4 and even up to 6 phenyl propane units, here called oligolignans. The amounts of lignans in the knots were similar in the radial direction from the pith into the outer branch, but decreased dramatically outwards in the branch, almost disappearing after 10–20 cm. The ratio of the 2 epimers of hydroxymatairesinol differed between different knots and even within the knot. A new spruce lignan, nortrachelogenin, or its enantiomer, wikstromol, was detected in knots from trees in northern Finland as opposed to samples from southern Finland. The amount of lipophilic extractives was small compared to the amount of hydrophilic extractives in the knots. Five of the dead knots contained more resin acids and free diterpenyl alcohols than ordinary stemwood. In the other knots, the amount of lipophilic extractives was on the same level as stem heartwood. The stem sapwood contained larger amounts of esterified fatty acids than the knots.

The cellular distribution of lignans in Tsuga heterophylla wood

Western hemlock heartwood contains patches of tracheids with large amounts of cellular inclusions. Microscopic and chemical examination of the wood showed several types of deposits containing the lignans matairesinol, hydroxymatairesinol and conidendrin. The deposits, which were often relatively pure individual lignans, frequently assumed different physical forms and chemical composition. A check in the wood contained three distinct forms of deposits each of which was a different lignan. Rays contained deposits physically similar to those in adjacent tracheids but, while lignans were present in the tracheids, they were not detected in the rays. Lignans lined tracheid walls as surface films and often encrusted the bordered pits. The amount of lignans in the wood was not related to wet wood zones although surface films and pit encrustations should have an influence on physical properties. The location and physical nature of lignan deposits in western hemlock heartwood indicates their biosynthesis has probably taken place at the heartwood periphery in the vicinity of the half-bordered pit.