Academic literature on the topic 'Lignans Lignans'

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Journal articles on the topic "Lignans Lignans"

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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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Dissertations / Theses on the topic "Lignans Lignans"

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Yvon, Brigitte L. "The synthesis of lignans and lignan analogs." Thesis, National Library of Canada = Bibliothèque nationale du Canada, 2000. http://www.collectionscanada.ca/obj/s4/f2/dsk1/tape3/PQDD_0010/MQ53256.pdf.

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Storer, N. P. "Asymmetric synthesis of lignans." Thesis, Swansea University, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.639120.

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An introduction to lignans, including classification, occurrrence, biological activity, the role of lignans and their biosynthesis, is described in chapter 1. Chapter 2 presents a review of the conjugate addition reaction, with particular emphasis on chiral conjugate additions. This chapter also reviews the synthesis of lignans via conjugate additions to both chiral and achiral acceptors. Chapter 3 describes an attempt to synthesize lignans via tandem conjugate additions to a chiral crotonate ester. The project was, however, unsuccessful, due to problems associated with the synthesis of the chiral ester. A number of protected derivatives of ethyl 4-hydroxycrotonate were, however synthesized, as were various mono-protected derivatives of (Z)-1,4-dihydroxybut-2-ene. Chapter 4 describes the synthesis of lignans via tandem conjugate addition to chiral (-)-5-(1-menthyloxy)furan-2(5H)-one. Conjugate addition utilizing diphenyl thioacetals as acyl anion equivalents, followed by in situ trapping with aromatic aldehydes or acid chlorides afforded the adducts in good yields. Desulphurisation and dementhylation yielded (-)-epipodorhizol, which on oxidation afforded (-)-podorhizon. This was successfully cyclised to (-)-γ-apopicropodophyllin, thereby constituting a formal total synthesis of chiral deoxypodophyllotoxin. Chapter 5 describes the use of O-tert-butyldimethysilyl protected cyanohydrins as acyl anion equivalents in the conjugate addition to the chiral butenolide. It has been shown that conjugate additions proceed to afford a single isomer, while tandem conjugate additions afford the adduct as a mixture of two isomers. Ketone regeneration from the cyanohydrin causes isomerisation to occur, to afford a single isomer. A novel dementhylation reaction utilizing sodium borohydride, which occurs with concurrent stereoselective reduction of ther benzylic ketone, is discussed. This methodology has realised the chiral synthesis of a member of the retrolignan series, and the potential for the synthesis of chiral 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans is discussed.
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Pereira, Marcos Donizete Peliçon [UNESP]. "Sesquiterpenos e lignanas de Holostylis reniformis." Universidade Estadual Paulista (UNESP), 2012. http://hdl.handle.net/11449/97973.

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Holostylis reniformis sintetiza uma variedade de compostos, incluindo seco lignanas e sesquiterpenos. Em busca de potenciais compostos antimaláricos, novos estudos fitoquímicos dos extratos de raízes foram realizados. Este trabalho descreve o isolamento de quatorze compostos por meio de técnicas cromatográficas, principalmente por CCD e CC, e CLAE. Estes compostos foram caracterizados por métodos espectrométricos, especialmente por experimentos de RMN e medidas de rotação óptica específica. A partir dos extratos de raízes de H. reniformis três sesquiterpenos novos, 4,5-seco-guaiano (7-epi-11-hidroxichabrolidiona A, XIV), uma lactona de nove membros (holostilactona, XV), e uma megastigmana [(6S,9S,7E)- 6,9-di-hidroxi-10-(2'-hidroxietoxi)-4,7-megastigmadien-3-ona, XVI], juntamente com uma nova lignana [(7R, 7'R,8S,8'S)-8,8'-dimetil-4-hidroxi-3',4',5,7-tetrametil-2,7'- ciclolignana, VIII] foram isoladas. Além disso, os compostos conhecidos sitosterol (I), alantoína (XI), e a lignana furânica futokadsurin C (IX) foram obtidos. Visando estudos posteriores sobre estrutura e atividade antimalárica, o composto (7'R,8S,8'S)-8,8'-dimetil-3',4',4,5-tetrametil-2,7'-ciclolignan-7-ona foi submetido a transformações químicas gerando dois derivados.
Holostylis reniformis can synthesize a variety of seco compounds including lignans and sesquiterpenes. In search of potential antimalarial compounds further phytochemical studies on the root extracts were carried out. This work describes the isolation of 14 compounds by chromatographic techniques, mainly by TLC, CC, and HPLC. These compounds were characterized by spectrometric methods, particularly by NMR experiments and optical rotation measurements. From the root extracts of H. reniformis three new sesquiterpenes, 4,5-seco-guaiane (7-epi-11- hydroxychabrolidione A, XIV), a nine-membered lactone (holostylactone, XV), and a megastigmane [(6S,7E,9S)-6,9-dihydroxy-10-(2'-hydroxyethoxy)-4,7-megastigmadien -3-one, XVI], together with a new lignan [(7R,7′R,8S,8′S)-8,8′-dimethyl-4-hydroxy- 3′,4′,5,7-tetramethoxy-2,7′-cyclolignan, VIII] were isolated. In addition, the known compounds sitosterol (I), allantoin (XI), and a tetrahydrofuran lignans futokadsurin C (IX) were obtained. (7′R,8S,8′S)-8,8′-dimethyl-3′,4′,4,5-tetramethoxy-2,7′-cyclolignan-7-one was subjected to chemical transformations into two derivatives for further structure and antimalarial activity studies
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Pereira, Marcos Donizete Peliçon. "Sesquiterpenos e lignanas de Holostylis reniformis /." Araraquara, 2012. http://hdl.handle.net/11449/97973.

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Orientador: Lucia Maria Xavier Lopes
Banca: André Luiz Meleiro Porto
Banca: Monica Tallarico Pupo
Resumo: Holostylis reniformis sintetiza uma variedade de compostos, incluindo seco lignanas e sesquiterpenos. Em busca de potenciais compostos antimaláricos, novos estudos fitoquímicos dos extratos de raízes foram realizados. Este trabalho descreve o isolamento de quatorze compostos por meio de técnicas cromatográficas, principalmente por CCD e CC, e CLAE. Estes compostos foram caracterizados por métodos espectrométricos, especialmente por experimentos de RMN e medidas de rotação óptica específica. A partir dos extratos de raízes de H. reniformis três sesquiterpenos novos, 4,5-seco-guaiano (7-epi-11-hidroxichabrolidiona A, XIV), uma lactona de nove membros (holostilactona, XV), e uma megastigmana [(6S,9S,7E)- 6,9-di-hidroxi-10-(2'-hidroxietoxi)-4,7-megastigmadien-3-ona, XVI], juntamente com uma nova lignana [(7R, 7'R,8S,8'S)-8,8'-dimetil-4-hidroxi-3',4',5,7-tetrametil-2,7'- ciclolignana, VIII] foram isoladas. Além disso, os compostos conhecidos sitosterol (I), alantoína (XI), e a lignana furânica futokadsurin C (IX) foram obtidos. Visando estudos posteriores sobre estrutura e atividade antimalárica, o composto (7'R,8S,8'S)-8,8'-dimetil-3',4',4,5-tetrametil-2,7'-ciclolignan-7-ona foi submetido a transformações químicas gerando dois derivados.
Abstract: Holostylis reniformis can synthesize a variety of seco compounds including lignans and sesquiterpenes. In search of potential antimalarial compounds further phytochemical studies on the root extracts were carried out. This work describes the isolation of 14 compounds by chromatographic techniques, mainly by TLC, CC, and HPLC. These compounds were characterized by spectrometric methods, particularly by NMR experiments and optical rotation measurements. From the root extracts of H. reniformis three new sesquiterpenes, 4,5-seco-guaiane (7-epi-11- hydroxychabrolidione A, XIV), a nine-membered lactone (holostylactone, XV), and a megastigmane [(6S,7E,9S)-6,9-dihydroxy-10-(2'-hydroxyethoxy)-4,7-megastigmadien -3-one, XVI], together with a new lignan [(7R,7′R,8S,8′S)-8,8′-dimethyl-4-hydroxy- 3′,4′,5,7-tetramethoxy-2,7′-cyclolignan, VIII] were isolated. In addition, the known compounds sitosterol (I), allantoin (XI), and a tetrahydrofuran lignans futokadsurin C (IX) were obtained. (7′R,8S,8′S)-8,8′-dimethyl-3′,4′,4,5-tetramethoxy-2,7′-cyclolignan-7-one was subjected to chemical transformations into two derivatives for further structure and antimalarial activity studies
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Ayella, Allan K. "Wheat lignans and cancer prevention." Diss., Manhattan, Kan. : Kansas State University, 2007. http://hdl.handle.net/2097/335.

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Nemes, Simona. "Practical methods for lignans quantification." Thesis, McGill University, 2012. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=110432.

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An optimized microwave-assisted extraction (MAE) method is proposed, in conjunction with high performance liquid chromatography (HPLC) analysis, for the general quantification of lignans in flaxseed materials and other plant foods. The method involves hydrolyzing 0.5 – 1.6 g samples with 50 ml of 0.5 M NaOH at 156 W (power level estimated using calorimetric calibration) for 3 min, using intermittent microwave power application (30 s on/off). The final temperature of the extracts is 67°C. The MAE method extracts the lignan from the plant matrix completely, accurately (97.5 % recovery), efficiently (yields 21.4 and 26.6 % higher than those obtained with reference methods), and precisely (coefficients of variation < 4.03 % for repeated determinations). An enzymatic hydrolysis (EH) method, complementary to the MAE method, was developed for the general determination of lignan aglycones in plant samples. The EH method involves hydrolyzing microwave-assisted extracts containing 100 mg sample in 3 ml of sodium acetate buffer (0.01 M, pH 5), with crude solutions of β-glucuronidase using ≥ 40 U of enzyme/mg sample (depending on the hydrolysing capacity of various batches of enzyme) by incubation at 37°C for 48 h. The lignan glucosides are hydrolysed in proportion of 95.6 %. The EH method is recommended for building databases of lignan contents in foods, useful for nutritionists and medical researchers who seek to assess the effects of dietary lignan intake on human health. Artificial neural network (ANN) and partial least squares (PLS) regression models, which are complementary to the MAE method, were calibrated for the general quantification of lignans in a variety of flaxseed materials. The lignan values predicted with the ANN and PLS models were in the range of ± 0.67 to 4.85 % of the reference lignan values. Using the ANN and PLS models requires measuring the UV-Vis light absorption of microwave-assisted flaxseed extracts at 289, 298, 343, and 765 nm, following the Folin-Ciocalteu's assay; the models are useful to the flaxseed processing industry for rapidly and accurately determining the lignan contents of various flaxseed raw materials. A non-automated, affordable and accurate solid phase extraction (SPE) method was developed for purifying microwave-assisted flaxseed extracts. The method requires the preparation of extracts prior to SPE by adjusting the pH of extracts in two stages, 1st to pH 3 with sulphuric acid for removing the water soluble proteins and carbohydrates by precipitation, and 2nd to pH 5 with sodium hydroxide for improving the retention of lignan by the packed SPE phase in order to reduce the lignan losses in the wash-water eluate. Microwave-assisted extracts from 0.6 and 1.5 g defatted flaxseed meal can be purified by SPE in order to recover in the 10, 20 and 30 % ethanol pooled eluates 71.2 % and 60.6 %, respectively, of the amount of lignan subjected to purification. SPE purified extracts can be used for further experiments, such as testing the antioxidant activity and the stability of the lignan extracts during various storage conditions.
Une méthode optimisée d'extraction assistée par micro-ondes (EAMO), en conjonction avec l'analyse par chromatographie liquide de haute performance, est proposée pour la quantification de lignanes, de façon généralisée, dans des échantillons des graines de lin et des aliments d'origine végétale. La méthode nécessite l'hydrolyse des échantillons de 0.5 - 1.6 g avec 50 ml de NaOH 0.5 M en appliquant 156 W (niveau de puissance estimé par calibration calorimétrique) de façon intermittente (30 s marche/arrêt) pour 3 min. La température finale des extraits était de 67°C. La méthode EAMO extrait les lignanes des matrices végétales complètement, avec exactitude (récupération de 97.5 %), avec efficacité (rendements de 21.4 et 26.6 % plus hauts que ceux obtenus avec des méthodes conventionnelles), et avec précision (coefficients de variation pour analyses répétées < 4.03 %).Une méthode d'hydrolyse enzymatique (HE), complémentaire pour la méthode EAMO, a été développée pour la quantification généralisée des lignanes aglycones dans des échantillons végétaux. La méthode HE nécessite l'hydrolyse des extraits, obtenus par EAMO, qui contient 100 mg d'échantillons dans 3 ml de solution tampon d'acétate de sodium (0.01 M, pH 5), avec des solutions d'enzyme β-glucuronidase en concentrations de ≥ 40 U d'enzyme/mg échantillon dépendant de la capacité d'hydrolyse des différents lots d'enzymes), par incubation a 37°C pour 48 h. Les lignanes glucosides sont hydrolysés en proportion de 95.6 %. La méthode HE est recommandée pour construire des bases des données des contenus en lignanes des aliments, qui sont utiles aux chercheurs en santé et nutrition qui cherchent à évaluer les effets des apports nutritionnels des lignanes sur la santé humaine. Des modèles de réseaux de neurones artificiels (RNA) et de régression par les moindres carrés partiels (MCP), qui sont complémentaires pour la méthode EAMO, ont été calibrés pour la quantification généralisée des lignanes dans une variété d'échantillons de graines de lin. Les valeurs des lignanes estimées avec les modèles RNA et MCP ont été dans des écarts de ± 0.67 jusqu'à 4.85 % des valeurs de référence des lignanes. L'utilisation de modèles RNA et MCP nécessite d'effectuer des tests de Folin-Ciocalteu afin de mesurer l'absorption de la lumière UV-Vis des extraits a 289, 298, 343, et 765 nm. Ces modèles sont utiles aux industries de transformations des graines de lin pour quantifier avec rapidité et précision les niveaux de lignanes dans les différentes sources de matières premières à base de graines de lin.Une méthode non-automatisée, abordable et précise d'extraction sur phase solide (EPS) a été développée afin de purifier des extraits de graines de lin produits par EAMO. La méthode nécessite la préparation des extraits avant la EPS par ajustement du pH à deux reprises; premièrement au pH 3 avec de l'acide sulfurique pour enlever, par précipitation, les protéines et les hydrates de carbone qui sont solubles dans l'eau; et, deuxièmement au pH 5 avec de l'hydroxyde de soude pour améliorer la rétention des lignanes en phase solide par l'entonnoir EPS afin de réduire les pertes de lignanes dans l'eau de lavage. Des extraits produits par EAMO à partir de 0.6 et 1.5 g de farine de graines de lin dégraissée peuvent être purifiés par EPS afin de récupérer 71.2 et 60.6 %, respectivement, de la quantité des lignanes utilisée pour la purification, dans les liquides d'élution des10, 20 et 30 % d'éthanol mis en commun. Des extraits purifiés par EPS peuvent être utilisés pour tester la capacité antioxydante et la stabilité des extraits des lignanes durant leur entreposage dans des conditions variées.
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Stevens, David R. "The synthesis of furofuranoid lignans." Thesis, University of Nottingham, 1989. http://eprints.nottingham.ac.uk/13170/.

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An approach to the synthesis of 2,6-diaryl-8-oxo-3,7-dioxabicyclo [3,3,0] octane lignan lactones is presented and then used in the synthesis of the natural products aptosimon and styraxin. The structure of aptosimon has now been confirmed as having a 2,6-diaryl structure rather than the 2,4-diaryl structure which has been postulated in the literature. A germination inhibitor MEL, isolated from Aegilops ovata, has also been synthesised. A key ring closing reaction in this strategy was a Lewis acid catalysed directed aldol reaction between a silyl enol ether and an acetal. A review of similar ring closures in the literature is presented. The use of alpha-arylidene lactones as intermediates in lignin synthesis has also been investigated. The stereochemistry of products from reactions used in this strategy was determined and as a result it was possible to successfully design a stereochemically controlled synthesis of dihydrosesamin.
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Bradley, Hilary Margaret. "Stereospecific approaches to THF-lignans." Thesis, University of Nottingham, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.315076.

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Figgitt, David Paul. "Antifungal effects of podophyllum lignans." Thesis, University of Nottingham, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.258435.

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Trazzi, Giordano. "Sintese de lignanas a partir de adutos de Morita-Baylis-Hillman : uma via geral de acesso a lignanas biologicamente ativas." [s.n.], 2008. http://repositorio.unicamp.br/jspui/handle/REPOSIP/250252.

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Orientador: Fernando Antonio Santos Coelho
Tese (doutorado) - Universidade Estadual de Campinas, Instituto de Química
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Resumo: Lignanas são produtos naturais produzidos por plantas, cuja diversidade estrutural e pronunciada atividade biológica têm atraído o interesse acadêmico e industrial há mais de um século, a exemplo do fármaco antitumoral Etoposide® (Sandoz), derivado semi-sintético da podofilotoxina, uma lignana natural até hoje comercialmente obtida por extração vegetal. Dentre as rotas de síntese de lignanas, as mais eficazes empregam uma b-benzil-g-butirolactona como intermediário-chave da estratégia. Nesse contexto, propusemos o emprego da reação de Morita-Baylis-Hillman (MBH) para o preparo de a-(aril-hidroximetil)- acrilatos (adutos de MBH) e sua utilização como materiais de partida para a síntese de b-(aril-silaniloximetil)-g-butirolactonas, novos intermediários-chave para a síntese de lignanas. Partindo paralelamente do piperonal, do 6-bromo-piperonal e da vanilina, empregamos a reação de MBH para preparar os a-(aril-hidroximetil)- acrilatos correspondentes, e então os utilizamos na preparação de suas respectivas b-(aril-silaniloximetil)-g-butirolactonas, de forma diastereosseletiva e com rendimentos globais de 56% a 69%, em 4 etapas a partir dos adutos de MBH. A b-(piperonil-silaniloximetil)-g-butirolactona foi empregada com alta eficiência na síntese total das lignanas naturais (±)-yateína, (±)-podorrizol e (±)-epi-podorrizol. A b-(6-bromo-piperonil-silaniloximetil)-g-butirolactona permitiu a preparação de um intermediário avançado para uma nova proposta sintética para a (±)- podofilotoxina. A b-(guaiacil-silaniloximetil)-g-butirolactona, obtida a partir da vanilina, e um intermediário chave para a síntese racemica da porção aglicona do medusasídeo A, uma nova lignana da classe dos dibenzilbutanodiois, cuja síntese ainda não foi descrita
Abstract: Lignans are plant-produced natural products, which structural diversity and pronounced biological activity has being attracting the interest of academy and industry through the entire last century, taking as example the antineoplasic drug Etoposide® (Sandoz), a semi-synthetic derivative of podophyllotoxin, a natural lignan which is, up to date, commercially obtained only by vegetal extraction. Among the routes of synthesis to lignans, the most efficient ones uses a b-benzyl- g-butyrolactone as the key intermediate. In this scenario, we have envisaged the use of the Morita-Baylis-Hillman reaction to synthetize a-(aryl-hydroxymethyl)- acrylates (MBH adducts) and it¿s use as starting materials to the synthesis of b-(aryl-silanyloxymethyl)-g-butyrolactones, new key intermediates to the synthesis of lignans. Starting alongside from piperonal, b-bromo-piperonal and vanillin, we used the MBH reaction to prepare the corresponding a-(aryl-hydroxymethyl)-acrylates (MBH adducts), and used it in the preparation of it¿s corresponding b-(arylsilanyloxymethyl)- g-butyrolactones, in a diastereoselective way and with global yields from 56% to 69% in four steps. The b-(piperonyl-silanyloxymethyl)-g- butirolactone obtained was used with high efficiency in the synthesis of natural lignans (±)-yatein, (±)-podorrizol and (±)-epi-podorrizol. The b-(6-bromo-piperonylsilanyloxymethyl)- g-butirolactone obtained allowed the preperation of an advanced intermediate to a new synthetic strategy to (±)-podophyllotoxyn. The b-(guaiacylsilanyloxymethyl)- g-butirolactone obtained is a key intermediate to the racemic synthesis of medusaside A aglycone, a new dibenzylbutanediol lignan whose synthesis was not described yet
Doutorado
Quimica Organica
Doutor em Ciências
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Books on the topic "Lignans Lignans"

1

Heitner, Cyril. Lignin and lignans: Advances in chemistry. Boca Raton: Taylor & Francis, 2010.

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Schmidt, John A., Cyril Heitner, and Don Dimmel. Lignin and lignans: Advances in chemistry. Edited by Heitner Cyril 1941-, Dimmel Don, and Schmidt John A. Boca Raton: Taylor & Francis, 2010.

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Calvo-Flores, Francisco G., José A. Dobado, Joaquín Isac-García, and Francisco J. Martín-MartíNez. Lignin and Lignans as Renewable Raw Materials. Chichester, UK: John Wiley & Sons, Ltd, 2015. http://dx.doi.org/10.1002/9781118682784.

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D, Loike J., ed. Lignans: Chemical, biological, and clinical properties. Cambridge [England]: Cambridge University Press, 1990.

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Mu zhi su hua xue. Beijing Shi: Hua xue gong ye chu ban she, 2010.

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Calvo-Flores, Francisco G. Lignin and lignans as renewable raw materials: Chemistry, technology and applications. Chichester, West Sussex: John Wiley and Sons, Inc., 2015.

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Rickard, Sharon Elizabeth. Flaxseed lignans and mammary carcinogenesis. Ottawa: National Library of Canada, 1993.

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Jenab, Mazda. The influence of flaxseed and lignans on colon carcinogenesis. Ottawa: National Library of Canada, 1994.

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author, Yin Jun, and Qin Chuixin author, eds. Schisandra chinensis: An herb of north eastern China origin. New Jersey: World Scientific, 2015.

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Lewis, Norman G., and Simo Sarkanen, eds. Lignin and Lignan Biosynthesis. Washington, DC: American Chemical Society, 1998. http://dx.doi.org/10.1021/bk-1998-0697.

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Book chapters on the topic "Lignans Lignans"

1

Peng, Yu. "Lignans, Lignins, and Resveratrols." In From Biosynthesis to Total Synthesis, 331–79. Hoboken, NJ: John Wiley & Sons, Inc, 2016. http://dx.doi.org/10.1002/9781118754085.ch10.

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Gottlieb, O. R., and M. Yoshida. "Lignans." In Natural Products of Woody Plants, 439–511. Berlin, Heidelberg: Springer Berlin Heidelberg, 1989. http://dx.doi.org/10.1007/978-3-642-74075-6_14.

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Durazzo, Alessandra. "Lignans." In Phenolic Compounds in Food, 185–200. Boca Raton : CRC Press, Taylor & Francis Group, 2018.: CRC Press, 2018. http://dx.doi.org/10.1201/9781315120157-11.

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Karimi, Reza, and Ali Rashidinejad. "Lignans." In Handbook of Food Bioactive Ingredients, 1–26. Cham: Springer International Publishing, 2022. http://dx.doi.org/10.1007/978-3-030-81404-5_15-1.

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Albertson, Anna K. F., and Jean-Philip Lumb. "The Lignans." In Recent Advances in Polyphenol Research, 1–70. Chichester, UK: John Wiley & Sons, Ltd, 2019. http://dx.doi.org/10.1002/9781119427896.ch1.

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Chen, Jicheng, Yazhen Chen, and Xianjiang Ye. "Lignans in Diets." In Handbook of Dietary Phytochemicals, 1–22. Singapore: Springer Singapore, 2019. http://dx.doi.org/10.1007/978-981-13-1745-3_38-1.

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Chen, Jicheng, Yazhen Chen, and Xianjiang Ye. "Lignans in Diets." In Handbook of Dietary Phytochemicals, 1687–708. Singapore: Springer Singapore, 2021. http://dx.doi.org/10.1007/978-981-15-4148-3_38.

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Lindsley, Craig W., Corey R. Hopkins, and Gary A. Sulikowski. "Biomimetic Synthesis of Lignans." In Biomimetic Organic Synthesis, 677–93. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2011. http://dx.doi.org/10.1002/9783527634606.ch18.

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Saarinen, Niina, Sari Mäkelä, and Risto Santti. "Anticancer Effects of Lignans." In Animal Cell Technology: Basic & Applied Aspects, 55–58. Dordrecht: Springer Netherlands, 2003. http://dx.doi.org/10.1007/978-94-017-0726-8_10.

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Thompson, Lilian U. "Role of Lignans in Carcinogenesis." In Phytochemicals in Human Health Protection, Nutrition, and Plant Defense, 51–65. Boston, MA: Springer US, 1999. http://dx.doi.org/10.1007/978-1-4615-4689-4_3.

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Conference papers on the topic "Lignans Lignans"

1

Shu, Jing, Shi Hui, Wan Lihua, Jiang Enping, Chen Dongxue, Chen Jianguang, and Fan Xintian. "Sedative and hypnotic effects of Schisandra Chinensis baill lignans." In 2011 International Conference on Human Health and Biomedical Engineering (HHBE). IEEE, 2011. http://dx.doi.org/10.1109/hhbe.2011.6028110.

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Xuebing, Jing, Yue Shunpu, Zhang Min, Sun Xiaomeng, Chen Jianguang, and Fan Xintian. "Effects of Schisandra Chinensis baill lignans on learning and memory dysfunctions." In 2011 International Conference on Human Health and Biomedical Engineering (HHBE). IEEE, 2011. http://dx.doi.org/10.1109/hhbe.2011.6028049.

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Ling Zhou, Xuekui Wang, Zuoliang Sha, Qinggui Xiao, and Hongbin Xu. "Simultaneous determination of four Schisandra lignans in the fruit of Schisandra Chinensis." In 2011 International Conference on New Technology of Agricultural Engineering (ICAE). IEEE, 2011. http://dx.doi.org/10.1109/icae.2011.5943994.

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Sun, Yu, Enping Jiang, and Jianguang Chen. "Protective effects of Schisandra Lignans on myocardial ischemia-reperfusion injury in anesthetized rats." In 2011 International Conference on Human Health and Biomedical Engineering (HHBE). IEEE, 2011. http://dx.doi.org/10.1109/hhbe.2011.6029073.

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Hammadi, Reham. "Isolation and structure determination of pregnane glycosides and lignans from an African species." In 2nd Symposium of Young Researchers on Pharmacognosy. Szeged: Department of Pharmacognosy, University of Szeged, Faculty of Pharmacy, 2021. http://dx.doi.org/10.14232/syrpharmacognosy.2021.a7.

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Guangxin, Yuan, Lu Di, Li Tan, Liu Yang, and Guan Ming. "Rapid determination of lignans in Schisandra Chinensis and Schisandra sphenanthera by micellar electrokinetic capillary chromatography." In 2011 International Conference on Human Health and Biomedical Engineering (HHBE). IEEE, 2011. http://dx.doi.org/10.1109/hhbe.2011.6027884.

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Christofidou-Solomidou, Melpo, James C. Lee, Floyd Dukes, Evguenia Arguiri, Shampa Chatterjee, Prashanthi Javvadi, Charalambos C. Solomides, Costas Koumenis, and Keith Cengel. "FLAXSEED LIGNANS PROTECT NORMAL LUNG ENDOTHELIAL CELLS FROM RADIATION-INDUCED OXIDATIVE CELL AND DNA DAMAGE." In American Thoracic Society 2010 International Conference, May 14-19, 2010 • New Orleans. American Thoracic Society, 2010. http://dx.doi.org/10.1164/ajrccm-conference.2010.181.1_meetingabstracts.a2004.

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Ning, Desheng, Yixia Fu, and Zhenghong Pan. "Separation and Purification of Three Main Lignans from the Anti-Inflammatory Extract of Lllicium Difengpi by High-Speed Counter-Current Chromatography." In 2016 2nd International Conference on Advances in Energy, Environment and Chemical Engineering (AEECE 2016). Paris, France: Atlantis Press, 2016. http://dx.doi.org/10.2991/aeece-16.2016.9.

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Kovyazin, Pavel V., Pavel V. Ivchenko, Ilya E. Nifant’ev, and Lyudmila V. Parfenova. "Synthesis of Dibenzylbutane and 9,8′-Neo-Lignans via Cyclometalation of Allylbenzene by EtAlCl2 and Mg in the Presence of Zr ansa-Complexes." In ECSOC-25. Basel Switzerland: MDPI, 2021. http://dx.doi.org/10.3390/ecsoc-25-11776.

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He, Yiqian, Yuan-Yuan Lei, Carol Kwok, Ashley Cheng, Ka-Li Cheung, Iris Lee, Roselle Lee, Suzanne Ho, and Winnie Yeo. "Abstract P2-13-19: Validation of a Chinese-specific food frequency questionnaire for assessing dietary lignans intake among breast cancer patients in Hong Kong." In Abstracts: 2019 San Antonio Breast Cancer Symposium; December 10-14, 2019; San Antonio, Texas. American Association for Cancer Research, 2020. http://dx.doi.org/10.1158/1538-7445.sabcs19-p2-13-19.

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Reports on the topic "Lignans Lignans"

1

Chum, H. L., and D. K. Johnson. Liquid Fuels from Lignins: Annual Report. Office of Scientific and Technical Information (OSTI), January 1986. http://dx.doi.org/10.2172/1017103.

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Lalvani, S. B. Lignin-assisted coal depolymerization. Office of Scientific and Technical Information (OSTI), January 1991. http://dx.doi.org/10.2172/5795190.

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Chung-Jui Tsai, Mark F. Davis, and Vincent L. Chiang. Genetic Augmentation of Syringyl Lignin in Low-lignin Aspen Trees, Final Report. Office of Scientific and Technical Information (OSTI), November 2004. http://dx.doi.org/10.2172/883338.

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Dilworth, G. L. Biochemical genetics of Lignin degradation. Office of Scientific and Technical Information (OSTI), February 1997. http://dx.doi.org/10.2172/471447.

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Lewis, N. G. Unravelling lignin formation and structure. Office of Scientific and Technical Information (OSTI), January 1991. http://dx.doi.org/10.2172/6001554.

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Carlson, John E. ''The control of lignin synthesis''. Office of Scientific and Technical Information (OSTI), April 2005. http://dx.doi.org/10.2172/838425.

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van Dam, Jan, Paulien Harmsen, Harriëtte Bos, and Richard Gosselink. Lignine : groene grondstof voor chemicaliën en materialen. Wageningen: Wageningen Food & Biobased Research, 2016. http://dx.doi.org/10.18174/398437.

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Author, Not Given. (Characterization of lignin peroxidases from Phanerochaete). Office of Scientific and Technical Information (OSTI), November 1990. http://dx.doi.org/10.2172/6015628.

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Yuan, Joshua S., Arthur Ragauskas, and Zhihua Liu. Synthetic Design of Microorganisms for Lignin Fuel. Office of Scientific and Technical Information (OSTI), March 2018. http://dx.doi.org/10.2172/1472013.

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Malito, M. L., and L. A. Jeffers. Development of a prototype lignin concentration sensor. Office of Scientific and Technical Information (OSTI), January 1993. http://dx.doi.org/10.2172/6744692.

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