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1
Sefkow, M., M. Raschke, and C. Steiner. "Enantioselective synthesis and biological evaluation of a-hydroxylated lactone lignans." Pure and Applied Chemistry 75, no. 2-3 (January 1, 2003): 273–78. http://dx.doi.org/10.1351/pac200375020273.
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A short and efficient synthesis of enantiomerically pure α-hydroxylated lactone lignans starting from commercially available diisopropyl malate is presented. Stereoselective alkylation with various benzyl bromides and saponification yielded the corresponding succinic acids. Acetalization afforded the dioxolanones, which were stereoselectively alkylated. Reduction (and deprotection, where required) yielded the lactone lignans in up to 30 % overall yield. The inhibition of the proliferation of HT29 colon cancer cells was investigated. One lignane, bis-2,4,6 trimethylbenzyllactone lignan, was active (IC50 = 35 μM), whereas all other tested lignans were inactive within the investigated concentration range.
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Monties, Bernard. "Composition chimique des bois de chêne: composés phénoliques, relations avec quelques propriétés physiques et chimiques susceptibles d'influencer la qualité des vins et des eaux-de-vie." OENO One 21, no. 3 (September 30, 1987): 169. http://dx.doi.org/10.20870/oeno-one.1987.21.3.1282.
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<p style="text-align: justify;">Les polyphénols du bois de chêne, extractibles et composés liés à la paroi végétale = lignines, lignanes, tanins et aldéhydes phénoliques, ont été envisagés au niveau moléculaire de leurs relations avec les propriétés physico-chimiques des bois : retrait, porosité, propriétés mécaniques.</p><p style="text-align: justify;">Des résultats originaux ont été aussi présentés concernant le fractionnement des polyphénols pariétaux, l'incrustation des parois par les tanins hydrolysables: acide ellagique associé à des fractions de lignine, ainsi que la formation d'aldéhydes phénoliques (vanilline, syringaldéhyde, aldéhydes coniférylique et sinapylique) par pyrolyse douce de la lignine. Des mécanismes réactionnels hypothétiques ont été suggérés.</p><p style="text-align: justify;">+++</p><p style="text-align: justify;">Oak wood phenolics, extractives and cell wall linked compounds : lignins, lignans, tanins and phenolic aldehydes have been discussed, at the molecular level, in their relations with physico-chemical properties of wood = shrinking, permeability and mechanical properties.</p><p style="text-align: justify;">Unpublished results have been also reported concerning fractionnation of cell wall phenolics, incrustation of cell wall by tanins: ellagic acid associated with lignins fractions and formation of phenolic aldehydes (vanillin, syringaldehyde, coniferaldehyde, sinapaldehyde) during mild pyrolysis of lignin in oak wood. Hypotherical reaction mechanism have been suggested.</p>
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Bolvig, Anne Katrine, Herman Adlercreutz, Peter Kappel Theil, Henry Jørgensen, and Knud Erik Bach Knudsen. "Absorption of plant lignans from cereals in an experimental pig model." British Journal of Nutrition 115, no. 10 (March 22, 2016): 1711–20. http://dx.doi.org/10.1017/s0007114516000829.
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AbstractPlant lignans are diphenolic compounds ingested with whole grains and seeds and converted to enterolignans by the colonic microbiota. In the present study, we investigated absorption and metabolism of plant lignans and enterolignansin vivoafter consumption of cereal-based diets. Six pigs fitted with catheters in the mesenteric artery and portal vein and with a flow probe attached to the portal vein along with twenty pigs for quantitative collection of urine were used for this study. The animals were fed bread based on wheat flour low in plant lignans and three lignan-rich breads based on whole-wheat grain, wheat aleurone flour or rye aleurone flour. Plant lignans and enterolignans in plasma were monitored daily at fast after 0–3 d of lignan-rich intake, and on the 4th day of lignan-rich intake a 10-h profile was completed. Urine samples were collected after 11 d of lignan-rich diet consumption. The concentrations of plant lignans were low at fast, and was 1·2–2·6 nmol/l after switching from the low-lignan diet to the lignan-rich diets. However, on the profile day, the concentration and quantitative absorption of plant lignans increased significantly from 33 nmol/h at fast to 310 nmol/h 0–2·5 h after ingestion with a gradual increase in the following periods. Quantitatively, the absorption of plant lignans across diets amounted to 7 % of ingested plant lignans, whereas the urinary excretion of plant lignans was 3 % across diets. In conclusion, there is a substantial postprandial uptake of plant lignans from cereals, suggesting that plant lignans are absorbed from the small intestine.
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Andargie, Mebeaselassie, Maria Vinas, Anna Rathgeb, Evelyn Möller, and Petr Karlovsky. "Lignans of Sesame (Sesamum indicum L.): A Comprehensive Review." Molecules 26, no. 4 (February 7, 2021): 883. http://dx.doi.org/10.3390/molecules26040883.
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Major lignans of sesame sesamin and sesamolin are benzodioxol--substituted furofurans. Sesamol, sesaminol, its epimers, and episesamin are transformation products found in processed products. Synthetic routes to all lignans are known but only sesamol is synthesized industrially. Biosynthesis of furofuran lignans begins with the dimerization of coniferyl alcohol, followed by the formation of dioxoles, oxidation, and glycosylation. Most genes of the lignan pathway in sesame have been identified but the inheritance of lignan content is poorly understood. Health-promoting properties make lignans attractive components of functional food. Lignans enhance the efficiency of insecticides and possess antifeedant activity, but their biological function in plants remains hypothetical. In this work, extensive literature including historical texts is reviewed, controversial issues are critically examined, and errors perpetuated in literature are corrected. The following aspects are covered: chemical properties and transformations of lignans; analysis, purification, and total synthesis; occurrence in Seseamum indicum and related plants; biosynthesis and genetics; biological activities; health-promoting properties; and biological functions. Finally, the improvement of lignan content in sesame seeds by breeding and biotechnology and the potential of hairy roots for manufacturing lignans in vitro are outlined.
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Huh, Jungmoo, Chang-Min Lee, Seoyoung Lee, Soeun Kim, Namki Cho, and Young-Chang Cho. "Comprehensive Characterization of Lignans from Forsythia viridissima by UHPLC-ESI-QTOF-MS, and Their NO Inhibitory Effects on RAW 264.7 Cells." Molecules 24, no. 14 (July 22, 2019): 2649. http://dx.doi.org/10.3390/molecules24142649.
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Lignans are known to be an important class of phenylpropanoid secondary metabolites. In the course of our studies on the chemodiversity of lignans, the necessity arose to develop a method for the fast detection and identification of bioactive lignan subclasses. In this study, we detected 10 lignan derivatives of different extracts of F. viridissima by UHPLC-ESI-QTOF-MS. Lignan glycosides (1 and 2), lignans (3 and 4), and lignan dimers (5–10) were identified by analysis of their exact masses and MSe spectra along with the characteristic mass fragmentation patterns and molecular formulas. We further investigated NO inhibitory effects of F. viridissima fractions and their major lignan derivatives to evaluate those anti-inflammatory effects. The methylene chloride fraction of F. viridissima as well as compounds 8 and 10 showed potent dose-dependent NO inhibitory effects on RAW 264.7 cells. Corresponding to the NO inhibition by compounds 8 and 10, lipopolysaccharide (LPS)-induced inducible nitric oxide synthase (iNOS) expression was notably reduced by both compounds. Our combined data with the bioactive results and the component analysis by UHPLC-ESI-QTOF-MS suggest that the methylene chloride fraction of F. viridissima roots could be potential anti-inflammatory agents and these are related to major lignans including dimeric dibenzylbutyrolactone lignans.
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Liu, Zhaomin, Bailing Chen, Baolin Li, Cheng Wang, Guoyi Li, Wenting Cao, Fangfang Zeng, and Yuming Chen. "Greater Consumption of Total and Individual Lignans and Dietary Fibers Were Significantly Associated with Lowered Risk of Hip Fracture—A 1:1 Matched Case–Control Study among Chinese Elderly Men and Women." Nutrients 14, no. 5 (March 5, 2022): 1100. http://dx.doi.org/10.3390/nu14051100.
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The study aims to examine the association of dietary intake of lignans with the risk of hip fractures in Chinese older adults. This was a 1:1 age- and gender- matched case–control study. Dietary survey was conducted by face-to-face interviews using a 79-item validated food frequency questionnaire. Habitual intake of total and individual lignans (matairesinol, secoisolariciresinol, pinoresinol, and lariciresinol) was estimated based on the available lignans databases. Conditional logistic regression was used to examine the relationship of dietary total and individual lignans, lignan-rich foods (vegetables, fruits, nuts, and cereals) and dietary fibers with the risk of hip fracture. A total of 1070 pairs of hip fracture incident cases and controls were recruited. Compared with the lowest quartile, the highest quartile group showed a reduced hip fracture risk by 76.3% (0.237, 95% CI: 0.103–0.544, Ptrend < 0.001) for total lignans, and 62.5% (0.375, 95% CI: 0.194–0.724, Ptrend = 0.001) for dietary fibers. Similar findings were observed for individual lignans, the estimated enterolactone level, as well as lignans from vegetables and nuts. We concluded that greater consumption of total and individual lignans, and lignan-rich foods were significantly associated with decreased risk of hip fracture.
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Muir, Alister D. "Flax LignansAnalytical Methods and How They Influence Our Understanding of Biological Activity." Journal of AOAC INTERNATIONAL 89, no. 4 (July 1, 2006): 1147–57. http://dx.doi.org/10.1093/jaoac/89.4.1147.
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Abstract Flaxseed (Linum usitatissimum L.) is a major source of dietary intake of lignans by virtue of the high concentrations (0.71.5) that are present in the seed. The principal lignan present in flaxseed is secoisolariciresinol diglucoside (SDG), which occurs as a component of a linear ester-linked complex in which the C6-OH of the glucose of SDG is esterified to the carboxylic acid of hydroxymethylglutaric acid. Also present in flaxseed and in resulting lignan extracts are significant quantities of 2 cinnamic acid glycosides. Our emerging understanding of the biological activity of flax lignans is based on studies using a variety of materials ranging from whole ground seed to pure SDG. The underlying assumption of most of these studies is that the biological activity of flax lignans results from their conversion to the mammalian lignans enterolactone (EL) and enterodiol (ED). There are, however, several intermediate compounds generated during the digestion and metabolism of flax lignans, including SDG and its aglycones and secoisolariciresinol (Seco), that are good candidates to be the principal bioactive molecule. This review will document the history of the development of lignan analytical methods and illustrate how analytical methods have influenced the interpretation of animal and human trials and our understanding of the biological activity of flax lignans.
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Willför, S., L. Nisula, J. Hemming, M. Reunanen, and B. Holmbom. "Bioactive phenolic substances in industrially important tree species. Part 1: Knots and stemwood of different spruce species." Holzforschung 58, no. 4 (July 7, 2004): 335–44. http://dx.doi.org/10.1515/hf.2004.052.
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Abstract Knots (i.e., branch bases inside tree stems) in spruce trees contained remarkably higher concentrations of lignans and oligolignans than the adjacent stemwood. The amount of lignans in some knots exceeded 10% (w w−1) and some knots contained hundreds of times more lignans than the heartwood in the same tree. However, there were large variations between different species and even between different knots in the same tree. 7-Hydroxymatairesinol was the predominant lignan in knots of Picea abies, P. glauca, P. koraiensis, P. mariana, and P. omorika, while liovil and secoisolariciresinol dominated in P. sitchensis and P. pungens. The lignans occur in free form in knots and are easily extracted with polar solvents. In addition to the true lignans, especially the knots contained large amounts of lignan-related oligomeric aromatic substances, here called oligolignans, consisting of three or four phenylpropane units. 7-Hydroxymatairesinol, but also other lignans, could be extracted in large scale from spruce knots at pulp and paper mills. Other potentially important lignans could be produced from 7-hydroxymatairesinol by semisynthesis. The ready availability of large amounts of lignans and oligolignans now enables research to assess their bioactivity and provide the basis for applications in medicine and nutrition or as natural antioxidants and antimicrobial agents in a variety of technical products.
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Petit, Hélène V. "Antioxidants and dairy production: the example of flax." Revista Brasileira de Zootecnia 38, spe (July 2009): 352–61. http://dx.doi.org/10.1590/s1516-35982009001300035.
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This manuscript reports on the main problems decreasing productivity of dairy cows (e.g. fatty liver syndrome and poor fertility) and how antioxidants could enhance it. High producing dairy cows are prone to oxidative stress, and the situation can be exacerbated under certain environmental, physiological, and dietary conditions. Antioxidants have important effects on the expression of genes involved in the antioxidant status, which may enhance animal health and reproduction. Moreover, antioxidants may contribute to decrease the incidence of spontaneous oxidized flavour in milk enriched in polyunsaturated fatty acids. Plant lignans are strong antioxidants and flax is the richest source of plant lignans. Flax lignans are converted in the mammalian lignans enterolactone and enterodiol. The main mammalian lignan in milk is enterolactone and flax lignans are converted in enterolactone mainly under the action of ruminal microbiota. Therefore, ruminal microbiota may be the most important flora to target for plant lignan metabolism in order to increase concentration of mammalian lignan antioxidants in milk of dairy cows. However, more research is required to improve our knowledge on metabolism of other antioxidants in dairy cows and how they can contribute in decreasing milk oxidation.
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M.K. Al-Ani, Widad, and Fitua M. Aziz. "Antimicrobial Activity of Hydroxymatairesinol (HMR) Lignan." Iraqi Journal of Pharmaceutical Sciences ( P-ISSN 1683 - 3597 E-ISSN 2521 - 3512) 22, no. 2 (March 28, 2017): 30–34. http://dx.doi.org/10.31351/vol22iss2pp30-34.
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Lignans are natural products widely distributed in the plant kingdom. They are composed of two β-β-linked phenylpropane (shikimate-derived biogenetic subunits). Although the backbone of lignans is composed of phenylpropane units, there is enormous diversity in the structure of lignans leading to different classes of lignans, such as γ-butyrolactone derivatives, eg. Hymatairesinol, bicyclooctadiene derivatives, e.g. pinoresinol, tetrahydrofuran derivatives e.g.lariciresinol, di-arylbutandiol derivatives, e.g. secoisolariciresinol. Introduction of a further carbon –carbon linkage leads to a class of lignans collectively known as cyclolignans such as tetrahydro-naphthalene derivatives, for example podophyllotoxin. Lignans have a broad range of biological activities; many of them show significant antitumour, antimitotic, and antiviral effects. They also have cardiovascular effects, antimicrobial and insecticidal activities. The efflux mechanisms of bacteria to some antibiotics and resistance of bacteria to many antibiotics led to search for antibacterial compound of plant origin to overcome these problems. The antibacterial activity of HMR lignan was determined using the disc diffusion method and the MIC of the isolated compound was tested by the broth micro-dilution method. HMR lignan showed activity against Staphylococcus epidermidis(17 mm), Candida albicans (13mm), Proteussp(12mm) and Klebsiella sp (12mm).
Key words: Lignans, Hydroxymatiaresinol, Antimicrobial activity
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Durazzo, Alessandra, Massimo Lucarini, Emanuela Camilli, Stefania Marconi, Paolo Gabrielli, Silvia Lisciani, Loretta Gambelli, et al. "Dietary Lignans: Definition, Description and Research Trends in Databases Development." Molecules 23, no. 12 (December 8, 2018): 3251. http://dx.doi.org/10.3390/molecules23123251.
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The study aims to communicate the current status regarding the development and management of the databases on dietary lignans; within the phytochemicals, the class of the lignan compounds is of increasing interest because of their potential beneficial properties, i.e., anticancerogenic, antioxidant, estrogenic, and antiestrogenic activities. Furthermore, an introductory overview of the main characteristics of the lignans is described here. In addition to the importance of the general databases, the role and function of a food composition database is explained. The occurrence of lignans in food groups is described; the initial construction of the first lignan databases and their inclusion in harmonized databases at national and/or European level is presented. In this context, some examples of utilization of specific databases to evaluate the intake of lignans are reported and described.
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Li, Wei, and Hye Jin Yang. "Phenolic Constituents from Platycodon grandiflorum Root and Their Anti-Inflammatory Activity." Molecules 26, no. 15 (July 27, 2021): 4530. http://dx.doi.org/10.3390/molecules26154530.
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Six lignols (1–6), including two new compounds (+)-(7R,8R)-palmitoyl alatusol D (1) and (+)-(7R,8R)-linoleyl alatusol D (2), along with four phenolics (7–10), a neolignan (11), three alkyl aryl ether-type lignans (12–14), two furofuran-type lignans (15–16), three benzofuran-type lignans (17–19), a tetrahydrofuran-type lignan (20), and a dibenzylbutane-type lignan (21) were isolated from the ethyl acetate-soluble fraction of the methanol extract of Platycodon grandiflorum (Jacq.) A. DC. root. The chemical structures of the obtained compounds were elucidated via high-resolution mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy analyses. The obtained spectroscopic data agreed well with literature. Among the isolated compounds, eighteen (1–7 and 11–21) were isolated from P. grandiflorum and the Campanulaceae family for the first time. This is the first report on lignol and lignan components of P. grandiflorum. The anti-inflammatory effects of the isolated compounds were examined in terms of their ability to inhibit the production of pro-inflammatory cytokines IL-6, IL-12 p40, and TNF-α in lipopolysaccharide-stimulated murine RAW264.7 macrophage cells. Nine compounds (4–6, 12, and 15–19) exhibited inhibitory effects on IL-12 p40 production, eleven compounds (1–6, 12, 15–17, and 19) exhibited inhibitory activity on IL-6 production, and eleven compounds (1–6 and 15–19) exhibited inhibitory effects against TNF-α. These results warrant further investigation into the potential anti-inflammatory activity and general benefits of the phenolic constituents of P. grandiflorum root.
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Rodríguez-García, Carmen, Cristina Sánchez-Quesada, Estefanía Toledo, Miguel Delgado-Rodríguez, and José Gaforio. "Naturally Lignan-Rich Foods: A Dietary Tool for Health Promotion?" Molecules 24, no. 5 (March 6, 2019): 917. http://dx.doi.org/10.3390/molecules24050917.
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Dietary guidelines universally advise adherence to plant-based diets. Plant-based foods confer considerable health benefits, partly attributable to their abundant micronutrient (e.g., polyphenol) content. Interest in polyphenols is largely focused on the contribution of their antioxidant activity to the prevention of various disorders, including cardiovascular disease and cancer. Polyphenols are classified into groups, such as stilbenes, flavonoids, phenolic acids, lignans and others. Lignans, which possess a steroid-like chemical structure and are defined as phytoestrogens, are of particular interest to researchers. Traditionally, health benefits attributed to lignans have included a lowered risk of heart disease, menopausal symptoms, osteoporosis and breast cancer. However, the intake of naturally lignan-rich foods varies with the type of diet. Consequently, based on the latest humans’ findings and gathered information on lignan-rich foods collected from Phenol Explorer database this review focuses on the potential health benefits attributable to the consumption of different diets containing naturally lignan-rich foods. Current evidence highlight the bioactive properties of lignans as human health-promoting molecules. Thus, dietary intake of lignan-rich foods could be a useful way to bolster the prevention of chronic illness, such as certain types of cancers and cardiovascular disease.
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Clavel, Thomas, Joël Doré, and Michael Blaut. "Bioavailability of lignans in human subjects." Nutrition Research Reviews 19, no. 2 (December 2006): 187–96. http://dx.doi.org/10.1017/s0954422407249704.
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Dietary lignans are phyto-oestrogens that possibly influence human health. The present review deals with lignan bioavailability, the study of which is crucial to determine to what extent metabolism, absorption and excretion of lignans alter their biological properties. Since intestinal bacteria play a major role in lignan conversion, for instance by producing the enterolignans enterodiol and enterolactone, emphasis is put on data obtained in recent bacteriological studies.
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Szopa, Agnieszka, Michał Dziurka, Angelika Warzecha, Paweł Kubica, Marta Klimek-Szczykutowicz, and Halina Ekiert. "Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts." Molecules 23, no. 12 (November 27, 2018): 3103. http://dx.doi.org/10.3390/molecules23123103.
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Schisandra rubriflora is a dioecious plant of increasing importance due to its lignan composition, and therefore, possible therapeutic properties. The aim of the work was lignan profiling of fruits, leaves and shoots of female (F) and male (M) plants using UHPLC-MS/MS. Additionally, the anti-inflammatory activity of plant extracts and individual lignans was tested in vitro for the inhibition of 15-lipooxygenase (15-LOX), phospholipases A2 (sPLA2), cyclooxygenase 1 and 2 (COX-1; COX-2) enzyme activities. The extracts of fruits, leaves and shoots of the pharmacopoeial species, S. chinensis, were tested for comparison. Twenty-four lignans were monitored. Lignan contents in S. rubriflora fruit extracts amounted to 1055.65 mg/100 g DW and the dominant compounds included schisanhenol, aneloylgomisin H, schisantherin B, schisandrin A, gomisin O, angeloylgomisin O and gomisin G. The content of lignan in leaf extracts was 853.33 (F) and 1106.80 (M) mg/100 g DW. Shoot extracts were poorer in lignans—559.97 (F) and 384.80 (M) mg/100 g DW. Schisantherin B, schisantherin A, 6-O-benzoylgomisin O and angeloylgomisin H were the dominant compounds in leaf and shoot extracts. The total content of detected lignans in S. chinensis fruit, leaf and shoot extracts was: 1686.95, 433.59 and 313.83 mg/100 g DW, respectively. Gomisin N, schisandrin A, schisandrin, gomisin D, schisantherin B, gomisin A, angeloylgomisin H and gomisin J were the dominant lignans in S. chinensis fruit extracts were. The results of anti-inflammatory assays revealed higher activity of S. rubriflora extracts. Individual lignans showed significant inhibitory activity against 15-LOX, COX-1 and COX-2 enzymes.
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Buchert, J., A. Mustranta, T. Tamminen, P. Spetz, and B. Holmbom. "Modification of Spruce Lignans with Trametes hirsuta Laccase." Holzforschung 56, no. 6 (November 5, 2002): 579–84. http://dx.doi.org/10.1515/hf.2002.088.
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Summary The effect of Trametes hirsuta laccase on isolated spruce wood lignans was evaluated. Lignans were isolated from the heartwood of spruce branches and treated with different laccase dosages and treatment times. The effect of the treatment was monitored by gas chromatography, size exclusion chromatography and ionization difference UV spectroscopy. Lignans were efficiently oxidized by T. hirsuta laccase. About half of the phenolic groups present in lignans remained intact during the treatment. The oxidation of phenolic groups in lignans produced oligomeric structures containing approximately 4–5 lignan units (i.e., 8–10 phenyl propane units). Precipitation of the formed oligomeric structures probably prevented further polymerization.
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Bommareddy, Ajay, Bhanu L. Arasada, Duane P. Mathees, and Chandradhar Dwivedi. "Determination of Mammalian Lignans in Biological Samples by Modified Gas Chromatography/Mass Spectrometry." Journal of AOAC INTERNATIONAL 90, no. 3 (May 1, 2007): 641–46. http://dx.doi.org/10.1093/jaoac/90.3.641.
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Abstract Lignans in flaxseed have been part of the human diet for centuries. In 1955, the isolation and structure of the lignan derivative secoisolariciresinol diglucoside (SDG) was reported. The biological role of SDG and mammalian lignan metabolites enterodiol and enterolactone was initially reported 20 years later. Experimental evidences showed the beneficial effects of lignans on breast, colon, and thyroid cancer. A modified gas chromatography/mass spectrometry (GC/MS) assay was developed for lignans in serum and colon samples of rats fed flaxseed meal. The method developed for the analysis of metabolites involves extraction and derivatization of samples and quantitative analysis by selected ion monitoring using GC/MS. The levels of lignan metabolites enterodiol and enterolactone were determined to be 0.013 and 0.23 M in serum samples and 0.008 and 1.63 M in colon samples.
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Hadeel, S. Y., S. A. Khalida, and Marie Walsh. "Antioxidant activity of sesame seed lignans in sunflower and flaxseed oils." Food Research 4, no. 3 (December 22, 2019): 612–22. http://dx.doi.org/10.26656/fr.2017.4(3).331.
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This study investigated the antioxidant activity of crude lignan extracts and purified lignans (sesamin, sesamolin, and sesamol) in sunflower and flaxseed oils. Lignan extracts were prepared from roasted sesame seed oil (LRSO) and unroasted sesame seed oil (LUSO). Additionally, the individual lignans were purified from both oils. The crude extracts and purified lignans were added at concentrations of 0.01, 0.02 and 0.03% to the oils and stored at 25 and 65°C over time and peroxide values and thiobarbituric acid values were measured. Each oil showed an increase in oxidation over time, with the samples stored at 65°C exhibiting accelerated oxidation. In general, LRSO showed higher antioxidant activity than LUSO and the antioxidant activity was similar to the antioxidant activity of butylated hydroxytoluene (0.02% BHT) in both oils when used at concentrations of 0.02 and 0.03%. Sesamol showed the highest antioxidant activity of each of the purified lignans followed by sesamin and sesamolin respectively. Crude and purified sesame lignans may have potential applications as natural antioxidants in food systems
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Liang, Zhonghou, Xiang Li, Ping Li, Ye Deng, Yuan Zhong, and Hua Yang. "Kadsura coccinea Lignan Metabolism Based on Metabolome and Transcriptome Analysis." Journal of Oncology 2022 (August 1, 2022): 1–9. http://dx.doi.org/10.1155/2022/3152155.
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Kadsura coccinea is an important resource of traditional Chinese medicine. We find out the gene information of enzymes related to lignan biosynthesis and metabolism of Kadsura coccinea, so as to provide a scientific basis for the breeding of new varieties of Kadsura coccinea. In this paper, 2-year-old Kadsura coccinea from Hunan Kadsura coccinea provincial germplasm resource bank was used as the material and its root, stem, and leaf were analyzed by extensive targeted metabolomics combined with transcriptome sequencing. The results showed the following: (1) 51 lignans were detected by metabolome analysis, and the content of lignans in roots was higher than that in stems and leaves. The high content of lignans in roots, stems, and leaves includes ring-opening isolarch phenol-4-o-glucoside, narrow leaf schisandrin E, and schisandrin B. (2) After transcriptome sequencing, 13 classes of 137 Unigenes related to lignan biosynthesis pathway were retrieved. The analysis of differential genes in different parts showed that the overall expression amount and species of Kadsura coccinea lignan synthase gene in stems and leaves were closer than those in roots. CCoAOMT, C3H, and SIDR gene families are mainly expressed in roots and stems. (3) Metabolome combined with transcriptome analysis further screened these genes and obtained 11 genes of enzyme gene families such as HCT, DIR, COMT, CAD, SIDR, and PLR, which are highly correlated in lignan synthesis. Therefore, there are many lignans and their synthase-related genes in Kadsura coccinea roots, stems, and leaves, but the content and expression of different lignans and their synthase-related genes are quite different in each part. In this study, the gene information of the Kadsura coccinea lignan biosynthesis enzyme was obtained for the first time, which laid a good foundation for the cloning and molecular breeding of the key enzyme gene of lignan biosynthesis.
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Zanella, Isabella, Giorgio Biasiotto, Finn Holm, and Diego di Lorenzo. "Cereal Lignans, Natural Compounds of Interest for Human Health?" Natural Product Communications 12, no. 1 (January 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200139.
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Cereals are suggested to be the most important sources of lignan in the diets of western populations. Recent epidemiological studies show that European subpopulations in which the major source of lignans are cereals, display lower disease frequency regarding metabolic and cardiovascular diseases. The biological mechanisms of lignan are several. Beyond their antioxidant and anti-inflammatory actions at nutritional doses some lignans regulate the activity of specific nuclear receptors (NRs), such as the estrogen receptors (ERs), and also NRs that are central switches in glucose and fatty acid metabolism such as PPARα, PPARγ and LXRs, highlighting them as selective nuclear receptor modulators (SNRMs). These include enterodiol (END) and enterolactone (ENL), the metabolites produced by the gut microbiota from food lignans. The available knowledge suggests that given some additional research it should be possible to make ‘function' claims for a regular intake of lignans-rich foods related to maintaining a healthy metabolism.
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Mason, Julie K., and Lilian U. Thompson. "Flaxseed and its lignan and oil components: can they play a role in reducing the risk of and improving the treatment of breast cancer?" Applied Physiology, Nutrition, and Metabolism 39, no. 6 (June 2014): 663–78. http://dx.doi.org/10.1139/apnm-2013-0420.
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Flaxseed (FS), rich in the phytoestrogen lignans and α-linolenic acid-rich oil, has been suggested to have an anticancer effect. Questions remain whether FS and its lignan and oil components are effective in reducing breast cancer risk and tumour growth, and can interact beneficially with breast cancer drugs. To find answers, in vitro, animal, observational, and clinical studies on FS and its lignan and oil components were reviewed. The majority of studies in various rodent models show that 2.5%–10% FS diet or the equivalent amount of lignan or oil reduces tumour growth. Ten percent FS and equivalent lignans do not interfere with but rather increase the effectiveness of tamoxifen (80 mg/day) while the 4% FS oil increases trastuzumab/Herceptin (2.5 mg/kg) effectiveness. Observational studies show that FS and lignan intake, urinary excretion, or serum levels are associated with reduced risk, particularly in postmenopausal women. Lignans reduce breast cancer and all-cause mortality by 33%–70% and 40%–53%, respectively, without reducing tamoxifen effectiveness. Clinical trials show that FS (25 g/day with 50 mg lignans; 32 days) reduces tumour growth in breast cancer patients and lignans (50 mg/day; 1 year) reduces risk in premenopausal women. Mechanisms include decreased cell proliferation and angiogenesis and increased apoptosis through modulation of estrogen metabolism and estrogen receptor and growth factor receptor signalling pathways. More clinical trials are needed but current overall evidence indicates that FS and its components are effective in the risk reduction and treatment of breast cancer and safe for consumption by breast cancer patients.
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Mulabagala, Vanisree, Gottumukkala V. Subbaraju, Modukuri V. Ramani, David L. DeWitt, and Muraleedharan G. Nair. "Lipid Peroxidation, Cyclooxygenase Enzyme and Tumor Cell Proliferation Inhibitory Lignans from Justicia Species." Natural Product Communications 3, no. 11 (November 2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301109.
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The genus Justicia is a rich source of lignans, especially aryl naphthalide lignans. Lignans are biologically active phytochemicals, and are reported to possess antiplatelet, antiviral, anti-tumor, antidepressant, and insect antifeedant activities. In the present study, we report lipid peroxidation (LPO), cyclooxygenase (COX-1 and −2) enzyme and tumor cell proliferation inhibitory activities of lignans, namely, lariciresinol (1), isolariciresinol (2), neesiinoside A (3), justirumalin (4), justalakonin (5), justicidin G (6), sesamin (7), sesamolin (8), jusmicranthin methyl ether (9), taiwanin E methyl ether (10), lignan J1 (11), jusneesiinol (12), jusmicranthin ethyl ether (13), tiruneesiin (14), justicidin E (15) and simplexolin (16). Lignans 1 and 2 were isolated from J. tranquebariensis, 3, 4, 6, 9, 10, 11, 12, 13 and 14 from J. neesii Ramamoorthy, 5 from J. purpurea and 7, 8, 15 and 16 from J. orbiculata. Among the lignans assayed, 1, 2, 12 and 14 showed 79.6, 86.2, 90.8 and 95.9% and 3 41.3% inhibition of LPO at 25 μg/mL. The lignans 4, 9 and 16 inhibited COX-2 enzyme by 67.2, 73.0 and 72.8%, respectively, when tested at 25 μg/mL. Similarly, lignans 3, 4, 10, 11 and 15 inhibited COX-1 enzyme by 59.9, 89.2, 69.6, 73.9, and 80.1%, respectively, at 25 μg/mL. When assayed at 25 μg/mL, 4 inhibited human stomach and breast cancer cell lines by 42.8 and 42.1%, respectively. Also, at 25 μg/mL the lignan 7 inhibited the growth of CNS, lung and breast cancer cell lines by 50.0, 41.3, and 42.0 %, respectively, and 15 inhibited the proliferation of lung, breast and colon cell lines by 40–53%.
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Sangiorgio, Paola, Simona Errico, Alessandra Verardi, Stefania Moliterni, Gabriella Tamasi, Claudio Rossi, and Roberto Balducchi. "Bioactive Lignans from Flaxseed: Biological Properties and Patented Recovery Technologies." Nutraceuticals 3, no. 1 (January 10, 2023): 58–74. http://dx.doi.org/10.3390/nutraceuticals3010005.
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Flaxseed lignans frequently feature in the literature. However, much remains to be discovered about the mechanisms underlying their functional and therapeutic properties. Furthermore, it is necessary to identify systems for lignan production and detoxification that are sustainable, cost-effective, easy to use, and scale up. These systems can address the needs of the nutraceutical, cosmetic, and pharmaceutical sectors and lead to competitive commercial products. This review analyzes the biological effects of lignans as anticancer, antioxidants, and modulators of estrogen activity. It also focuses on the most recent articles on lignan extraction methods that are sustainable and suitable as products for human consumption. Furthermore, the most up-to-date and relevant patents for lignan recovery are examined. The search and selection methodology for articles and patents was conducted using the most popular bibliographic and patent databases (e.g., Scopus, Pubmed, Espacenet). To the best of our knowledge, this is the first overview that details the patented technologies developed in the flaxseed lignans area in the last 10 years.
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Park, Woo Sung, Kyung Ah Koo, Ji-Yeong Bae, Hye-Jin Kim, Dong-Min Kang, Ji-Min Kwon, Seung-Mann Paek, Mi Kyeong Lee, Chul Young Kim, and Mi-Jeong Ahn. "Dibenzocyclooctadiene Lignans in Plant Parts and Fermented Beverages of Schisandra chinensis." Plants 10, no. 2 (February 13, 2021): 361. http://dx.doi.org/10.3390/plants10020361.
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The fruit of Schisandra chinensis, Omija, is a well-known traditional medicine used as an anti-tussive and anti-diarrhea agent, with various biological activities derived from the dibenzocyclooctadiene-type lignans. A high-pressure liquid chromatography-diode array detector (HPLC-DAD) method was used to determine seven lignans (schisandrol A and B, tigloylgomisin H, angeloylgomisin H, schisandrin A, B, and C) in the different plant parts and beverages of the fruit of S. chinensis grown in Korea. The contents of these lignans in the plant parts descended in the following order: seeds, flowers, leaves, pulp, and stems. The total lignan content in Omija beverages fermented with white sugar for 12 months increased by 2.6-fold. Omija was fermented for 12 months with white sugar, brown sugar, and oligosaccharide/white sugar (1:1, w/w). The total lignan content in Omija fermented with oligosaccharide/white sugar was approximately 1.2- and 1.7-fold higher than those fermented with white sugar and brown sugar, respectively. A drink prepared by immersion of the fruit in alcohol had a higher total lignan content than these fermented beverages. This is the first report documenting the quantitative changes in dibenzocyclooctadiene-type lignans over a fermentation period and the effects of the fermentable sugars on this eco-friendly fermentation process.
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Antúnez-Mojica, Mayra, Antonio Romero-Estrada, Israel Hurtado-Díaz, Alfonso Miranda-Molina, and Laura Alvarez. "Lignans from Bursera fagaroides: Chemistry, Pharmacological Effects and Molecular Mechanism. A Current Review." Life 11, no. 7 (July 13, 2021): 685. http://dx.doi.org/10.3390/life11070685.
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Bursera fagaroides is a medicinal tree endemic to México, it belongs to the Burseraceae family and has proven antitumor activity. Modern research, performed principally with the bark extracts, have indicated that lignans are the main active constituents of B. fagaroides, with a high content of aryltetralin, aryldihydronaphtalene, dibenzylbutirolactone, and dibenzylbutane-type lignans as the constituents of the active extracts. In general, lignans from B. fagaroides exhibited potent anti-cancer activity, although antitumor, anti-bacterial, anti-protozoal, anti-inflammatory, and anti-viral properties have also been described. This review covers literature-reported lignans from B. fagaroides, chemical structures, nomenclature, chromatographic techniques of isolation, characterization strategies, and highlights the anti-cancer molecular mechanisms of lignans. Evaluation of the anticancer function of lignans has been extensively investigated since the cytotoxic in vitro results and in vivo assays in mice and zebrafish models to the tubulin molecular recognition by NMR. Also, we discuss the future direction for studying this important plant species and its lignan metabolites.
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Nurmi, Tarja, Jaakko Mursu, José L. Peñalvo, Henrik E. Poulsen, and Sari Voutilainen. "Dietary intake and urinary excretion of lignans in Finnish men." British Journal of Nutrition 103, no. 5 (October 8, 2009): 677–85. http://dx.doi.org/10.1017/s0007114509992261.
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Intake of lignans has been assessed in different study populations, but so far none of the studies has compared the daily intake of lignans and the urinary excretion of plant and enterolignans. We assessed the intake of lariciresinol, pinoresinol, secoisolariciresinol and matairesinol in 100 Finnish men consuming their habitual omnivorous diet, and measured the 24 h urinary excretion of plant and enterolignans to compare the intake and metabolism. Dietary determinants of lignan intake and their urinary excretion were also determined. The mean intake of lignans was 1224 (sd 539) μg/d, of which lariciresinol and pinoresinol covered 78 %. Almost half (47 %) of the intake of lignans was explained by the intake of rye products, berries, coffee, tea and roots. The urinary excretion of plant lignans corresponded to 17 % and enterolignans to 92 % of the intake of lignans. The urinary excretion of plant lignans was explained 14 % by the intake of rye products and intake of coffee, and consequently 3–7 % by the intake of water-insoluble fibre. The urinary excretion of enterolactone was explained 11 % by the intake of vegetables and rye products, 14 % by the intake of water-soluble fibre and only 4 % by the intake of lariciresinol. Although the assessed intake of lignans corresponded well with the urinary excretion of lignans, the enterolactone production in the human body depended more on the dietary sources of lignans than the absolute intake of lignans.
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Kim, A.-Young, Choong-In Yun, Joon-Goo Lee, and Young-Jun Kim. "Determination and Daily Intake Estimation of Lignans in Sesame Seeds and Sesame Oil Products in Korea." Foods 9, no. 4 (March 30, 2020): 394. http://dx.doi.org/10.3390/foods9040394.
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Sesame (Sesamum indicum L.) is a plant that belongs to the Pedaliaceae family which was first classified as a food source around 4000 years ago. Lignans (sesamin, sesamolin, sesamol, and sesaminol) present in sesame are the primary functional compounds that impart important health benefits. However, very little information is available on the lignan intake from sesame seeds and sesame oil products. Sesame oil is frequently and highly consumed in Korea and therefore is one of the important lignan intake sources due to the food eating habits of Koreans. Herein, we studied the distribution of lignans in sesame seeds (n = 21) and oil (n = 34) to estimate the daily lignan intake by the Korean population. High-performance liquid chromatography, in conjunction with statistical analysis, was used to determine the lignan content of seeds and oil. The estimated daily intake of total lignans from sesame seeds and oil, as estimated from the available domestic consumption data (Korea Nutrition and Health Examination Survey), is 18.39 mg/person/day for males and 13.26 mg/person/day for females. The contributions of lignan intake from sesame seeds and oil are 23.0% and 77.0%, respectively. This study provides preliminary information on lignan intake from sesame seeds and oil in the Korean population.
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Consonni, Roberto, and Gianluca Ottolina. "NMR Characterization of Lignans." Molecules 27, no. 7 (April 5, 2022): 2340. http://dx.doi.org/10.3390/molecules27072340.
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Lignans are particularly interesting secondary metabolites belonging to the phenyl-propanoid biosynthetic pathway. From the structural point of view, these molecules could belong to the aryltetralin, arylnaphtalene, or dibenzylbutyrolactone molecular skeleton. Lignans are present in different tissues of plants but are mainly accumulated in seeds. Extracts from plant tissues could be characterized by using the NMR-based approach, which provides a profile of aromatic molecules and detailed structural information for their elucidation. In order to improve the production of these secondary metabolites, elicitors could effectively stimulate lignan production. Several plant species are considered in this review with a particular focus on Linum species, well recognized as the main producer of lignans.
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Buckleton, JS, RC Cambie, GR Clark, PA Craw, CEF Rickard, PS Rutledge, and PD Woodgate. "Oxidative Coupling of Lignans. II. Non-Phenolic Coupling of Diarylbutane Lignans Related to Matairesinol Dimethyl Ether." Australian Journal of Chemistry 41, no. 3 (1988): 305. http://dx.doi.org/10.1071/ch9880305.
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The non- phenolic oxidative coupling of some diarylbutane lignans related to matairesinol dimethyl ether (1) has been investigated. Coupling with a thallium(III) oxidant, prepared in situ from thallium(III) oxide and trifluoroacetic acid, converts these lignans efficiently into either dibenzocyclooctadiene or aryltetralin lignans. The dibenzocyclooctadiene lignan (5) prepared from oxidative coupling of matairesinol dimethyl ether has been converted into compound (26) which has significant in vitro antileukaemic activity. The structure of the isostegane (27) formed by oxidative coupling of dimethylbutane (14) has been confirmed by X-ray crystallography.
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Josef, Balík, Híc Pavel, Kulichová Jana, Novotná Pavla, Tříska Jan, Vrchotová Naděžda, Strohalm Jan, and Houška Milan. "Wines with Increased Lignan Content by the Addition of Lignan Extracts." Czech Journal of Food Sciences 34, No. 5 (November 1, 2016): 439–44. http://dx.doi.org/10.17221/575/2015-cjfs.
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Red and white wines [Grüner Veltliner white wine and Blue Limberger (Blaufränkisch) red wine (vintage 2013)] were enriched with lignan hydroxymatairesinol originated from spruce knots. These spruce knots with removed resin were extracted with ethyl alcohol of agricultural origin. Ethanol extracts of lignans were then used to enrich wine sorts. Enriched wines were stored for 13 months. At 2, 6, and 13 months, samples were taken and subjected to a variety of analyses and sensory evaluations. Analyses included 7-hydroxymatairesinol and alpha-conidendrin lignan content, antioxidant activity (as determined by FRAP), total polyphenols, and sensory evaluation. The obtained data were evaluated using the analysis of variance to determine which factors e.g. wine type, quantity of added lignan extracts, additional sugar, method of preservation, and storage time had the most significant influence on lignan content, antioxidant activity and polyphenol content. In all cases the lignan content in the wines was significantly influenced by the addition of lignan extracts. After one year of storage, lignan contents changed only moderately and added lignans were stable in stored wines. Total polyphenol content in wines and the antioxidant activity of wines were significantly influenced by the type of wine (i.e., red or white). The presented method of wine enrichment with lignans opens the door for the production of extra quality wines.
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Papadakis, Emmanouil N., Despina Lazarou, Raphael Grougnet, Prokopios Magiatis, Alexios L. Skaltsounis, Euphemia Papadopoulou-Mourkidou, and Athanasios I. Papadopoulos. "Effect of the form of the sesame-based diet on the absorption of lignans." British Journal of Nutrition 100, no. 6 (December 2008): 1213–19. http://dx.doi.org/10.1017/s0007114508978272.
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The effect of different forms of sesame-based diets on the concentration of plasma lignans was assayed by estimating the levels of certain lignans (sesame lignans and enterolignans) in the plasma of experimental animals. In a series of experiments, male Wistar rats were fed either a raw sesame-enriched diet or a tahini-enriched diet. The plasma concentration of the lignans (sesame lignans and enterolignans) was determined at various time intervals over a 24 h period after a single administration. Enterodiol and enterolactone concentration in the tahini-treated group was significantly higher than in the raw sesame-treated group. In another series of experiments, male Wistar rats were fed, for 15 d, diets enriched in raw dehulled sesame, sesame perisperm, sesame oil, tahini and a polyphenolic extract derived from the seed perisperm. Enterodiol and enterolactone plasma concentration was high in the case of the sesame perisperm in spite of its low concentration in the assessed sesame lignans. Overall, the levels of the sesame lignans and enterolignans present in plasma seem to be influenced not only by the amount of lignan intake but also by other factors such as the form of the sesame-based diet.
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Milder, Ivon E. J., Ilja C. W. Arts, Betty van de Putte, Dini P. Venema, and Peter C. H. Hollman. "Lignan contents of Dutch plant foods: a database including lariciresinol, pinoresinol, secoisolariciresinol and matairesinol." British Journal of Nutrition 93, no. 3 (March 2005): 393–402. http://dx.doi.org/10.1079/bjn20051371.
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Enterolignans (enterodiol and enterolactone) can potentially reduce the risk of certain cancers and cardiovascular diseases. Enterolignans are formed by the intestinal microflora after the consumption of plant lignans. Until recently, only secoisolariciresinol and matairesinol were considered enterolignan precursors, but now several new precursors have been identified, of which lariciresinol and pinoresinol have a high degree of conversion. Quantitative data on the contents in foods of these new enterolignan precursors are not available. Thus, the aim of this study was to compile a lignan database including all four major enterolignan precursors. Liquid chromatography–tandem mass spectrometry was used to quantify lariciresinol, pinoresinol, secoisolariciresinol and matairesinol in eighty-three solid foods and twenty-six beverages commonly consumed in The Netherlands. The richest source of lignans was flaxseed (301 129 μg/100 g), which contained mainly secoisolariciresinol. Also, lignan concentrations in sesame seeds (29 331 μg/100 g, mainly pinoresinol and lariciresinol) were relatively high. For grain products, which are known to be important sources of lignan, lignan concentrations ranged from 7 to 764 μg/100 g. However, many vegetables and fruits had similar concentrations, because of the contribution of lariciresinol and pinoresinol.Brassicavegetables contained unexpectedly high levels of lignans (185–2321 μg/100 g), mainly pinoresinol and lariciresinol. Lignan levels in beverages varied from 0 (cola) to 91 μg/100 ml (red wine). Only four of the 109 foods did not contain a measurable amount of lignans, and in most cases the amount of lariciresinol and pinoresinol was larger than that of secoisolariciresinol and matairesinol. Thus, available databases largely underestimate the amount of enterolignan precursors in foods.
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Willför, S., J. Hemming, M. Reunanen, C. Eckerman, and B. Holmbom. "Lignans and Lipophilic Extractives in Norway Spruce Knots and Stemwood." Holzforschung 57, no. 1 (January 8, 2003): 27–36. http://dx.doi.org/10.1515/hf.2003.005.
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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.
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Mansikkala, Tuomas, Minna Patanen, Anna Kärkönen, Risto Korpinen, Andrey Pranovich, Takuji Ohigashi, Sufal Swaraj, et al. "Lignans in Knotwood of Norway Spruce: Localisation with Soft X-ray Microscopy and Scanning Transmission Electron Microscopy with Energy Dispersive X-ray Spectroscopy." Molecules 25, no. 13 (June 30, 2020): 2997. http://dx.doi.org/10.3390/molecules25132997.
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Lignans are bioactive compounds that are especially abundant in the Norway spruce (Picea abies L. Karst.) knotwood. By combining a variety of chromatographic, spectroscopic and imaging techniques, we were able to quantify, qualify and localise the easily extractable lignans in the xylem tissue. The knotwood samples contained 15 different lignans according to the gas chromatography-mass spectrometry analysis. They comprised 16% of the knotwood dry weight and 82% of the acetone extract. The main lignans were found to be hydroxymatairesinols HMR1 and HMR2. Cryosectioned and resin-embedded ultrathin sections of the knotwood were analysed with scanning transmission X-ray microscopy (STXM). Cryosectioning was found to retain only lignan residues inside the cell lumina. In the resin-embedded samples, lignan was interpreted to be unevenly distributed inside the cell lumina, and partially confined in deposits which were either readily present in the lumina or formed when OsO4 used in staining reacted with the lignans. Furthermore, the multi-technique characterisation enabled us to obtain information on the chemical composition of the structural components of knotwood. A simple spectral analysis of the STXM data gave consistent results with the gas chromatographic methods about the relative amounts of cell wall components (lignin and polysaccharides). The STXM analysis also indicated that a torus of a bordered pit contained aromatic compounds, possibly lignin.
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Sakakibara, Akira, Takashi Sasaya, Keiji Miki, and Hidetoshi Takahashi. "Lignans and Brauns' Lignins from Softwoods." Holzforschung 41, no. 1 (January 1987): 1–11. http://dx.doi.org/10.1515/hfsg.1987.41.1.1.
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Bleidere, Māra, Sanita Zute, Natālija Gailāne, Ināra Kantāne, Ida Jākobsone, and Vadims Bartkevičs. "Lignans in Oat and Barley Grains Depending on Genotype and Farming Practice." Proceedings of the Latvian Academy of Sciences. Section B. Natural, Exact, and Applied Sciences. 76, no. 1 (February 1, 2022): 124–30. http://dx.doi.org/10.2478/prolas-2022-0019.
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Abstract Cereals are an important source of vitamins, minerals, dietary fibre, and various phytochemicals, such as plant lignans. Lignans are a group of phenolic compounds that are commonly found in plants as their secondary metabolites. Lignans, found also in foodstuffs such as grains and seeds, are biologically active antioxidants, which reduce the occurrence of diabetes and cardiovascular diseases and prevent the progression of breast and prostate cancer. The aim of the study was to determine concentrations of lignans in different barley and oat genotypes grown under organic and conventional farming practices. Samples were collected in 2013 und 2014. The concentration of lignans was determined by high-performance liquid chromatography coupled with tandem mass spectrometry (HPLC-MS/MS). The highest concentration of total lignans was found in oat grains: 507.1 ± 3.0 (509.2 in 2013 and 505.0 in 2014) µg·100−1g. In barley grains, total lignin concentration was 425.2 ± 30.3 (403.8 in 2013 and 446.6 in 2014) µg·100−1g were detected. Concentration of some lignans, like HO-Mata, Lari and Pino, was higher both in oat (450.0, 3323 and 1159.8 µg·kg−1, respectively) and barley grain (334.3, 3297 and 334.4 µg·kg−1, respectively). The lignan concentration in studied oat and barley samples did not differ significant depending on cultivation practice.
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Mukker, Jatinder Kaur, Ravi Shankar Prasad Singh, Alister D. Muir, Ed S. Krol, and Jane Alcorn. "Comparative pharmacokinetics of purified flaxseed and associated mammalian lignans in male Wistar rats." British Journal of Nutrition 113, no. 5 (February 26, 2015): 749–57. http://dx.doi.org/10.1017/s0007114514004371.
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Consumption of flaxseed lignans is associated with various health benefits; however, little is known about the bioavailability of purified lignans in flaxseed. Data on their bioavailability and hence pharmacokinetics (PK) are necessary to better understand their role in putative health benefits. In the present study, we conducted a comparative PK analysis of the principal lignan of flaxseed, secoisolariciresinol diglucoside (SDG), and its primary metabolites, secoisolariciresinol (SECO), enterodiol (ED) and enterolactone (EL) in rats. Purified lignans were intravenously or orally administered to each male Wistar rat. SDG and its primary metabolites SECO, ED and EL were administered orally at doses of 40, 40, 10 and 10 mg/kg, respectively, and intravenously at doses of 20, 20, 5 and 1 mg/kg, respectively. Blood samples were collected at 0 (pre-dose), 5, 10, 15, 20, 30 and 45 min, and at 1, 2, 4, 6, 8, 12 and 24 h post-dosing, and serum samples were analysed. PK parameters and oral bioavailability of purified lignans were determined by non-compartmental methods. In general, administration of the flaxseed lignans SDG, SECO and ED demonstrated a high systemic clearance, a large volume of distribution and short half-lives, whereas administration of EL at the doses of 1 mg/kg (intravenously) and 10 mg/kg (orally administered) killed the rats within a few hours of dosing, precluding a PK analysis of this lignan. PK parameters of flaxseed lignans exhibited the following order: systemic clearance, SDG < SECO < ED; volume of distribution, SDG < SECO < ED; half-life, SDG < ED < SECO. The percentage of oral bioavailability was 0, 25 and < 1 % for SDG, SECO and ED, respectively.
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Go¨zler, Belkis, Mustafa A. O¨nu¨r, Tekant Go¨zler, Gu¨lden Kadan, and Manfred Hesse. "Lignans and lignan glycosides fromHaplophyllum cappadocicum." Phytochemistry 37, no. 6 (December 1994): 1693–98. http://dx.doi.org/10.1016/s0031-9422(00)89594-1.
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Willför, Stefan, Linda Nisula, Jarl Hemming, Markku Reunanen, and Bjarne Holmbom. "Bioactive phenolic substances in industrially important tree species. Part 2: Knots and stemwood of fir species." Holzforschung 58, no. 6 (October 1, 2004): 650–59. http://dx.doi.org/10.1515/hf.2004.119.
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Abstract Knots, i.e. branch bases inside tree stems, in fir trees contained remarkably higher concentrations of lignans, oligolignans, and juvabiones than the adjacent stemwood. Eight fir species were analysed (Abies sibirica, A. lasiocarpa, A. balsamea, A. alba, A. amabilis, A. veitchii, A. sachalinensis, and A. concolor). The amount of lignans could in some knots exceeds 6% (w/w) and the knots generally contained 20–50 times more lignans than the stemwood. However, there were large variations, not only between species but also even between knots in the same tree. Secoisolariciresinol was the predominant lignan in all knots. The lignans occur in free form in the knots and are easily extracted with polar solvents. In addition to the lignans, oligomeric aromatic substances, mainly sesquineo- and dineolignans, and juvabiones were accumulated in the knotwood. Secoisolariciresinol, but also lariciresinol (Abies alba) and 7-hydroxymatairesinol (A. amabilis), could be extracted in large scale from fir knots at pulp and paper mills. The ready availability of large amounts of lignans and oligolignans now enables research to assess their bioactivity and provide the base for applications in medicine and nutrition, or as natural antioxidants and antimicrobial agents in various technical products.
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Polat Kose, Leyla, and İlhami Gulcin. "Evaluation of the Antioxidant and Antiradical Properties of Some Phyto and Mammalian Lignans." Molecules 26, no. 23 (November 24, 2021): 7099. http://dx.doi.org/10.3390/molecules26237099.
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In this study, the antioxidant and antiradical properties of some phyto lignans (nordihydroguaiaretic acid, secoisolariciresinol, secoisolariciresinol diglycoside, and α-(-)-conidendrin) and mammalian lignans (enterodiol and enterolactone) were examined by different antioxidant assays. For this purpose, radical scavenging activities of phyto and mammalian lignans were realized by 2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) radical (ABTS•+) scavenging assay and 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) scavenging assay. Additionally, the reducing ability of phyto and mammalian lignans were evaluated by cupric ions (Cu2+) reducing (CUPRAC) ability, and ferric ions (Fe3+) and [Fe3+-(TPTZ)2]3+ complex reducing (FRAP) abilities. Also, half maximal inhibitory concentration (IC50) values were determined and reported for DPPH• and ABTS•+ scavenging influences of all of the lignan molecules. The absorbances of the lignans were found in the range of 0.150–2.320 for Fe3+ reducing, in the range of 0.040–2.090 for Cu2+ reducing, and in the range of 0.360–1.810 for the FRAP assay. On the other hand, the IC50 values of phyto and mammalian lignans were determined in the ranges of 6.601–932.167 µg/mL for DPPH• scavenging and 13.007–27.829 µg/mL for ABTS•+ scavenging. In all of the used bioanalytical methods, phyto lignans, as secondary metabolites in plants, demonstrated considerably higher antioxidant activity compared to that of mammalian lignans. In addition, it was observed that enterodiol and enterolactone exhibited relatively weaker antioxidant activities when compared to phyto lignans or standard antioxidants, including butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), Trolox, and α-tocopherol.
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Schöttner, Matthias, Dietmar Ganßer, and Gerhard Spitelle. "Interaction of Lignans with Human Sex Hormone Binding Globulin (SHBG)." Zeitschrift für Naturforschung C 52, no. 11-12 (December 1, 1997): 834–43. http://dx.doi.org/10.1515/znc-1997-11-1218.
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Abstract Lignans bind to sex hormone-binding globulin (SHBG ). The lignan with the highest binding affinity is (±)-3,4-divanillyltetrahydrofuran. In a double Stobbe condensation - without use of protecting groups - a wide variety of lignans with different substitution pattern in the aromatic and aliphatic part of the molecule was synthesized. These lignans were tested in a SHBG -binding assay which allowed to deduce the following relationship between structure and activity: 1) (±)-diastereoisomers are more active than meso compounds 2.) the 4-hydroxy- 3-methoxy (guajacyl) substitution pattern in the aromatic part is most effective 3.) the activity increases with the decline in polarity of the aliphatic part of the molecule.
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Mangmool, Supachoke, Chayaporn Limpichai, Khine Kyi Han, Vichai Reutrakul, and Natthinee Anantachoke. "Anti-Inflammatory Effects of Mitrephora sirikitiae Leaf Extract and Isolated Lignans in RAW 264.7 Cells." Molecules 27, no. 10 (May 21, 2022): 3313. http://dx.doi.org/10.3390/molecules27103313.
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Mitrephora sirikitiae Weeras., Chalermglin & R.M.K. Saunders has been reported as a rich source of lignans that contribute to biological activities and health benefits. However, cellular anti-inflammatory effects of M. sirikitiae leaves and their lignan compounds have not been fully elucidated. Therefore, this study aimed to investigate the anti-inflammatory activities of methanol extract of M. sirikitiae leaves and their lignan constituents on lipopolysaccharide (LPS)-induced inflammation in RAW 264.7 mouse macrophage cells. Treatment of RAW 264.7 cells with the methanol extract of M. sirikitiae leaves and its isolated lignans, including (−)-phylligenin (2) and 3′,4-O-dimethylcedrusin (6) significantly decreased LPS-induced prostaglandin E2 (PGE2) and nitric oxide (NO) productions. These inhibitory effects of the extract and isolated lignans on LPS-induced upregulation of PGE2 and NO productions were derived from the suppression of cyclooxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS) production, respectively. In addition, treatment with 2-(3,4-dimethoxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3) and mitrephoran (5) was able to suppress LPS-induced tumor necrosis factor alpha (TNF-α) secretion and synthesis in RAW 264.7 cells. These results demonstrated that M. sirikitiae leaves and some isolated lignans exhibited potent anti-inflammatory activity through the inhibition of secretion and synthesis of PGE2, NO, and TNF-α.
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Cow, Christopher, Carmen Leung, and James L. Charlton. "Antiviral activity of arylnaphthalene and aryldihydronaphthalene lignans." Canadian Journal of Chemistry 78, no. 5 (May 1, 2000): 553–61. http://dx.doi.org/10.1139/v00-059.
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A practical method for large scale synthesis of 1-arylnaphthalene and 1-aryl-1,2-dihydronaphthalene lignans is described. The method makes use of the classic Stobbe condensation followed by regioselective reactions that provide access to both the common and retrolactone lignans, e.g., 2 and 3. A total of 25 compounds, many of which are known natural products, were prepared and their antiviral activity against human cytomegalovirus measured.Key words: lignan, Stobbe, arylnaphthalene, antiviral.
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Lin, Yulan, Alicja Wolk, Niclas Håkansson, Jose Luis Peñalvo, Jesper Lagergren, Herman Adlercreutz, and Yunxia Lu. "Validation of FFQ-based assessment of dietary lignans compared with serum enterolactone in Swedish women." British Journal of Nutrition 109, no. 10 (September 25, 2012): 1873–80. http://dx.doi.org/10.1017/s000711451200387x.
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The validity of using FFQ to assess dietary lignans is uncertain. We aimed to validate the use of FFQ for the assessment of dietary intake of lignans compared to the serum biomarker enterolactone, the main product of dietary lignans' metabolism in human subjects. A random sample of women, aged 55–75 years, from the Swedish Mammography Cohort was selected. Information from two FFQ, the FFQ-87 (sixty-seven food items) and the FFQ-97 (ninety-three food items), and blood samples were collected. Dietary intake of lignans (secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, medioresinol and syringaresinol) was assessed by the FFQ. Serum concentrations of enterolactone were analysed by time-resolved fluoroimmunoassay. The correlation coefficient between energy-adjusted lignan intake and serum enterolactone was estimated in crude and multivariable-adjusted models, taking into account the factors potentially influencing the serum enterolactone. Among the 135 participants aged 55–75 years, with a mean BMI of 26·7 kg/m2, the average energy-adjusted intake of total lignans was 1616 (sd 424) and 1516 (sd 409) μg/d according to the FFQ-87 (forty-five food items containing lignans) and the FFQ-97 (sixty-five food items containing lignans), respectively. The mean concentration of serum enterolactone was 23·2 (sd 15·4) nmol/l. The adjusted Pearson's correlation between dietary intake of lignans assessed by the FFQ-97 and serum enterolactone was statistically significant (r 0·22, P= 0·01). No significant correlation was observed for the FFQ-87 (r 0·09, P= 0·30). The present study indicates that the FFQ-97 might be better than the FFQ-87 for assessing dietary intake of lignans, although the correlation was low.
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Valsta, Liisa M., Annamari Kilkkinen, Witold Mazur, Tarja Nurmi, Anna-Maija Lampi, Marja-Leena Ovaskainen, Tommi Korhonen, Herman Adlercreutz, and Pirjo Pietinen. "Phyto-oestrogen database of foods and average intake in Finland." British Journal of Nutrition 89, S1 (June 2003): S31—S38. http://dx.doi.org/10.1079/bjn2002794.
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Information on phyto-oestrogen intake in various populations has been scanty until now, primarily because data on the content of these compounds in foods were lacking. We report here on expansion of the Finnish National Food Composition Database (Fineli®) with values for the plant lignans matairesinol and secoisolariciresinol and the isoflavones daidzein and genistein. The values, expressed as aglycones, were based on food analyses (mainly GC–MS) or imputed from analytical data for 180 foods for lignans and 160 foods for isoflavones; additionally, over 1000 values were derived from the recipe database of Fineli. Average intake of these phyto-oestrogens was calculated using food consumption data of the National Dietary Survey FINDIET 1997, which was carried out in a random sample of the adult population in five areas in Finland. The dietary data were collected by 24 h recall (n=2862). The mean lignan intake was 434 (standard deviation (SD) 1575) μg/d and the mean isoflavone intake was 788 (SD 673) μg/d. Women had a higher lignan density (μg lignans/MJ) in their diet than men (P<0·05). Men had a higher mean daily isoflavone intake, 902 (SD 368) μg, than women, 668 (SD 963) μg (P<0·05). The sources of lignans were many: seeds, cereals, fruit, berries and vegetables. The main sources of isoflavones appeared to be processed meat products/sausages containing soya as an ingredient, and legumes as such. The average intake of lignans and isoflavones in Finland seems to be low, but intake varies throughout the population.
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Dossou, Senouwa Segla Koffi, Shengnan Song, Aili Liu, Donghua Li, Rong Zhou, Muez Berhe, Yanxin Zhang, et al. "Resequencing of 410 Sesame Accessions Identifies SINST1 as the Major Underlying Gene for Lignans Variation." International Journal of Molecular Sciences 24, no. 2 (January 5, 2023): 1055. http://dx.doi.org/10.3390/ijms24021055.
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Sesame is a promising oilseed crop that produces specific lignans of clinical importance. Hence, a molecular description of the regulatory mechanisms of lignan biosynthesis is essential for crop improvement. Here, we resequence 410 sesame accessions and identify 5.38 and 1.16 million SNPs (single nucleotide polymorphisms) and InDels, respectively. Population genomic analyses reveal that sesame has evolved a geographic pattern categorized into northern (NC), middle (MC), and southern (SC) groups, with potential origin in the southern region and subsequent introduction to the other regions. Selective sweeps analysis uncovers 120 and 75 significant selected genomic regions in MC and NC groups, respectively. By screening these genomic regions, we unveiled 184 common genes positively selected in these subpopulations for exploitation in sesame improvement. Genome-wide association study identifies 17 and 72 SNP loci for sesamin and sesamolin variation, respectively, and 11 candidate causative genes. The major pleiotropic SNPC/A locus for lignans variation is located in the exon of the gene SiNST1. Further analyses revealed that this locus was positively selected in higher lignan content sesame accessions, and the “C” allele is favorable for a higher accumulation of lignans. Overexpression of SiNST1C in sesame hairy roots significantly up-regulated the expression of SiMYB58, SiMYB209, SiMYB134, SiMYB276, and most of the monolignol biosynthetic genes. Consequently, the lignans content was significantly increased, and the lignin content was slightly increased. Our findings provide insights into lignans and lignin regulation in sesame and will facilitate molecular breeding of elite varieties and marker-traits association studies.
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Charlton, James L., and Gaik-Lean Chee. "Asymmetric synthesis of lignans using oxazolidinones as chiral auxiliaries." Canadian Journal of Chemistry 75, no. 8 (August 1, 1997): 1076–83. http://dx.doi.org/10.1139/v97-127.
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A simple procedure for the asymmetric synthesis of lignans via chiral β-benzyl-γ-butyrolactones has been developed. The key benzylbutyrolactone intermediates were efficiently synthesized using a six-step procedure, starting from 3,4-(methylenedioxy)cinnamic acid. The key step in this sequence was a highly diastereoselective alkylation of an N-acyloxazolidinone enolate. The resulting β-benzyl-γ-butyrolactones were subsequently transformed into the benzylidene lignans gossypifan and savinin (hibalactone) via aldol condensation–dehydration reactions, and into the dibenzylbutyrolactone lignan 4′-demethylyatein, through alkylation. Oxidation of 4′-demethylyatein with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) afforded cis-and trans-benzylidenebenzylbutyrolactones, whereas oxidation with DDQ/TFA gave 4′-demethyl-deoxyisopodophyllotoxin. Keywords: lignans, synthesis, asymmetric, biosynthesis, oxidation, benzylbutyrolactones.
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Smeds, Annika I., Iveta Češková, Patrik C. Eklund, and Stefan M. Willför. "Identification of new lignans in Norway spruce knotwood extracts." Holzforschung 66, no. 5 (July 1, 2012): 553–67. http://dx.doi.org/10.1515/hf-2011-0218.
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Abstract In a hydrophilic extract of Norway spruce knotwood, the dominating lignan, 7-hydroxymatairesinol, was partially removed by precipitation, and the resulting mixture was fractionated by flash chromatography and preparative high-performance liquid chromatography (HPLC). In the HPLC fractions, 7S- and 7R-todolactol A, 7′-hydroxylariciresinol, and two stereoisomers of 9′-hydroxylariciresinol were identified by gas chromatography-mass spectrometry (GC-MS) analyses, and their structures were confirmed by nuclear magnetic resonance spectroscopy. The 9′-hydroxylariciresinols were suggested to have the 7S,8R,8′R,9′Rand 7R,8R,8′R,9′Rconfigurations, and (-)-7′-hydroxylariciresinol 7S*,7′R*,8R*,8′S*, which indicates a configuration of this structure that has not been reported previously. 7S- and 7R-isoliovil were identified by comparison with previously published GC-MS data, and 7′-oxolariciresinol was tentatively identified on the basis of its mass spectrum. Of these lignans, only 7′-hydroxylariciresinol has been identified previously in Norway spruce. Several other lignans with similar mass spectra as the todolactols, isoliovils, and 7′-hydroxylariciresinol were detected, indicating that they are different stereoisomers of these lignans and/or of liovils. In addition to these lignans, the mass spectra of several other unidentified minor lignans indicated the presence of several tens of previously unidentified minor lignans in Norway spruce knotwood, accounting altogether for approximately 6% of the dry weight of the ethanol extract. 7S-Todolactol A, which was dominating among the new lignans, was found to be very unstable in aqueous solutions. Identification of more of these unidentified lignans may be possible only by access to pure reference compounds.
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Alp, Hayriye. "Usage of Flaxseed Lignan in Menaposal Complaınts in Perımenaposal Women Patıents." Obstetrics Gynecology and Reproductive Sciences 5, no. 7 (September 25, 2021): 01–03. http://dx.doi.org/10.31579/2578-8965/092.
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Lignans are phenylpropanoid dimers widely distributed in the plant kingdom. Flaxseed (Linum usitatissimum) is one of the richest sourcase of dietary lignans. Plant lignans comprise one of the two main groups of phytoestrogens the other group beigng the isoflavonoids. The major flax lignan is secoisolariciresinol diglucoside (SDG).Flaxseed is the richest food sourcase of SDG.Flaxseed also contains much smaller amounts of matairesinol, lariciresinol, and pineresinol. The plant lignans are converted by the intestinal microflora in the proximal or upper part of the large intestine to enterodiol (END) and enterolactone (ENL). Between 2017 and 2019, 26 female patients who applied for getat polk, obesity and perimenopausal complaints were included in the study. Demographic data of the patients were recorded. Age, weight, height, BMI and bloodT3,4, TSH, B12, Na, K levels were measured. Statistically average measurements were taken. Flaxseed was recommended for patients whose cholesterol levels were above the reference value. SDG has antioksidant activity.It also may have hypoglycemic, hypocholesterolemic, estrogenic,anti-estrogenic, anticancer, antiproliferative and renoprotective properties.
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Sarajlija, H., N. Čukelj, G. Novotni D Mršić, M. Brnčić, and D. Ćurić. "Preparation of flaxseed for lignan determination by gas chromatography–mass spectrometry method." Czech Journal of Food Sciences 30, No. 1 (January 30, 2012): 45–52. http://dx.doi.org/10.17221/107/2010-cjfs.
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Since 1980s, several methods for the determination of lignans in food samples have been developed depending on the types of lignans and foods analysed, but mostly on flaxseed as a reference food. In this work, specific steps in flaxseed preparation for lignan secoisolariciresinol analysis by gas chromatography-mass spectrometry method were examined. Ethanol extraction of lignan from defatted and non-defatted flaxseed before acid hydrolysis yielded significantly lower concentrations (5172 ± 49 μg/g; 5159 ± 83 μg/g, respectively), when compared to the direct acid hydrolysis (8566 ± 169 μg/g; 8571 ± 192 μg/g, respectively). In the analysed samples of defatted and dried flaxseed, no significant difference in lignan content was observed when compared to non-defatted flaxseed samples.