27 results match your criteria comparison secoisolariciresinol

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Effect of different structural flaxseed lignans on the stability of flaxseed oil-in-water emulsion: An interfacial perspective.

Food Chem 2021 Apr 8;357:129522. Epub 2021 Apr 8.

Oil Crops Research Institute of the Chinese Academy of Agricultural Sciences, Hubei Key Laboratory of Lipid Chemistry and Nutrition, and Key Laboratory of Oilseeds Processing, Ministry of Agriculture, Oil Crops and Lipids Process Technology National & Local Joint Engineering Laboratory, Wuhan 430062, China. Electronic address:

The influences of the different structural flaxseed lignans on flaxseed oil (FO) emulsions during storage and digestion were investigated, focusing on their interfacial behavior. From perspective of interface, more than 60% of secoisolariciresinol (SECO) and the acidic hydrolysates of flaxseed lignan macromolecule (FLEH) were located on the interface of FO emulsions. It improved the stability of FO emulsions both during storage and digestion by inhibiting of free radical penetration and improving their targeted antioxidative activity. Read More

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Quantification of lignans in 30 ground coffee samples and evaluation of theirs extraction yield in espresso coffee by HPLC-MS/MS triple quadrupole.

Int J Food Sci Nutr 2020 Mar 6;71(2):193-200. Epub 2019 Jun 6.

School of Pharmacy, University of Camerino, Camerino, Italy.

Lignans are a class of polyphenols considered to be phytoestrogens because of their oestrogenic/antiestrogenic activities and their plant origin. Few works have reported on the content of lignans in ground coffee, and most of them analysed a small number of samples. Hence, our aim was to quantify the content of three lignans, secoisolariciresinol, lariciresinol and matairesinol, in ground coffee by using high-performance liquid chromatography tandem mass spectrometry. Read More

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Does the enterolactone (ENL) affect fatty acid transporters and lipid metabolism in liver?

Nutr Metab (Lond) 2017 13;14:69. Epub 2017 Nov 13.

Department of Physiology, Medical University of Bialystok, Białystok, Poland.

Background: NAFLD as a result of inappropriate diet and obesity, may progress to sever conditions such as: type 2 diabetes mellitus or steatohepatitis, and has recently become a prevalent topic of numerous investigations. Due to its dangerous aftermaths, finding new substances, such as polyphenols and their derivatives, which might reduce liver steatosis is the main target of research into NAFLD treatment. Hence, the aim of the present study was to evaluate the effect(s) of enterolactone (ENL), a metabolite of secoisolariciresinol (SECO), on lipid metabolism together with changes in the expression of fatty acid transporters in fatty liver. Read More

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November 2017

Protective Role of Flaxseed Oil and Flaxseed Lignan Secoisolariciresinol Diglucoside Against Oxidative Stress in Rats with Metabolic Syndrome.

J Food Sci 2017 Dec 30;82(12):3029-3036. Epub 2017 Oct 30.

Postgraduate Program in Biochemistry, Federal Univ. of Pampa, Uruguaiana, Rio Grande do Sul, Brazil.

This study evaluated the protective effect of flaxseed oil (FO) and flaxseed lignan secoisolariciresinol diglucoside (SDG) against oxidative stress in rats with metabolic syndrome (MS). 48 rats were allocated into the following 6 groups: Groups 1 (control), 5 (FO), and 6 (SDG) received water and were treated daily orally with saline, FO, and SDG, respectively. Groups 2 (MS), 3 (MS+FO), and 4 (MS+SDG) received 30% fructose in drinking water for MS induction and were treated daily orally with saline, FO, and SDG, respectively. Read More

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December 2017

Incomplete metabolism of phytoestrogens by gut microbiota from children under the age of three.

Int J Food Sci Nutr 2018 May 20;69(3):334-343. Epub 2017 Jul 20.

a Departamento de Tecnología de Alimentos , Instituto Nacional de Investigación y Tecnología Agraria y Alimentaria (INIA) , Madrid , Spain.

Phytoestrogens are plant-derived polyphenols with structural and functional similarities to mammalian oestrogens. The aim of this work was to study the metabolism of phytoestrogens by children's intestinal microbiota and to compare it with previous results in adults. Faecal samples of 24 healthy children were subjected to phytoestrogen fermentation assay. Read More

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Evaluation of phenolic profile and antioxidant capacity in gluten-free flours.

Food Chem 2017 Aug 31;228:367-373. Epub 2017 Jan 31.

Institute of Environmental and Agricultural Chemistry, Università Cattolica del Sacro Cuore, via Emilia parmense 84, 29122 Piacenza, Italy. Electronic address:

The characterization of phenolic fingerprints in common gluten-free flours is still scarce. Total phenolic and anthocyanin contents, antioxidant capacity and the entire phenolic profile were investigated for extracts from chickpea, sorghum, quinoa, black rice, lentil, amaranth, brown rice, oat and white rice flours, using soft wheat flour as a comparison. The highest phenolic content was found in black rice, followed by quinoa extracts (147. Read More

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Characterization of Klebsiella sp. strain S1: a bacterial producer of secoisolariciresinol through biotransformation.

Can J Microbiol 2017 Jan 29;63(1):1-10. Epub 2016 Jun 29.

a Systemomics Center, College of Pharmacy, and Genomics Research Center (State-Province Key Laboratories of Biomedicine-Pharmaceutics of China), Harbin Medical University, Harbin, People's Republic of China.

Secoisolariciresinol (SECO) is a lignan of potential therapeutic value for diseases such as cancer, but its use has been limited by the lack of ideal production methods, even though its precursors are abundant in plants, such as flaxseeds. Here, we report the characterization of a bacterial strain, S1, isolated from the human intestinal flora, which could produce secoisolariciresinol by biotransformation of precursors in defatted flaxseeds. This bacterium was a Gram-negative and facultatively anaerobic straight rod without capsules. Read More

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January 2017

De Novo Transcriptomes of Forsythia koreana Using a Novel Assembly Method: Insight into Tissue- and Species-Specific Expression of Lignan Biosynthesis-Related Gene.

PLoS One 2016 21;11(10):e0164805. Epub 2016 Oct 21.

Bioorganic Research Institute, Suntory Foundation for Life Sciences, Kyoto, 619-0284, Japan.

Forsythia spp. are perennial woody plants which are one of the most extensively used medicinal sources of Chinese medicines and functional diets owing to their lignan contents. Lignans have received widespread attention as leading compounds in the development of antitumor drugs and healthy diets for reducing the risks of lifestyle-related diseases. Read More

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Comparison of phytochemical profiles and health benefits in fiber and oil flaxseeds (Linum usitatissimum L.).

Food Chem 2017 Jan 11;214:227-233. Epub 2016 Jul 11.

Department of Food Science, Stocking Hall, Cornell University, Ithaca, NY 14853, USA. Electronic address:

Flaxseed (Linum usitatissimum L.) is a rich source of nutritive and bioactive compounds. The research evaluated the disparity in phytochemical profiles along with total and cellular antioxidant activities between oil and fiber flaxseeds. Read More

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January 2017

Development and validation of an efficient ultrasound assisted extraction of phenolic compounds from flax (Linum usitatissimum L.) seeds.

Ultrason Sonochem 2015 Sep 28;26:176-185. Epub 2015 Feb 28.

Laboratoire de Biologie des Ligneux et des Grandes Cultures (LBLGC), UPRES EA 1207, Université d'Orléans, Chartres, France. Electronic address:

Flaxseed accumulates in its seedcoat a macromolecular complex composed of lignan (secoisolariciresinol diglucoside, SDG), flavonol (herbacetin diglucoside, HDG) and hydroxycinnamic acids (p-couramic, caffeic and ferulic acid glucosides). Their antioxidant and/or cancer chemopreventive properties support their interest in human health and therefore, the demand for their extraction. In the present study, ultrasound-assisted extraction (UAE) of flaxseed phenolic compounds was investigated. Read More

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September 2015

Crossbreeding of transgenic flax plants overproducing flavonoids and glucosyltransferase results in progeny with improved antifungal and antioxidative properties.

Mol Breed 2014 21;34(4):1917-1932. Epub 2014 Aug 21.

Faculty of Biotechnology, Wroclaw University, Przybyszewskiego 63/77, 51-148 Wrocław, Poland.

Flavonoids are a large group of secondary plant metabolites with many important functions; they play a role in fruit, flower and seed pigmentation and are involved in multiple protective mechanisms. They are very active natural antioxidants, acting as antimicrobial compounds in defense against pathogens, and they protect the plant against various stress factors, including excessive solar radiation and temperature. They are also an animal deterrent. Read More

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The biomedical potential of genetically modified flax seeds overexpressing the glucosyltransferase gene.

BMC Complement Altern Med 2012 Dec 10;12:251. Epub 2012 Dec 10.

Len Pharma, ul, Zamkowa 17, 82-200 Malbork, Poland.

Background: Flax (Linum usitatissimum) is a potential source of many bioactive components that can be found in its oil and fibers, but also in the seedcake, which is rich in antioxidants. To increase the levels of medically beneficial compounds, a genetically modified flax type (named GT) with an elevated level of phenylopropanoids and their glycoside derivatives was generated. In this study, we investigated the influence of GT seedcake extract preparations on human fibroblast proliferation and migration, and looked at the effect on a human skin model. Read More

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December 2012

[Effects of flaxseed extract on rheological properties of blood in experimental ovariectomy].

Eksp Klin Farmakol 2011 ;74(7):19-21

The effect of flaxseed extract (FSE) containing 42% secoisolariciresinol diglucoside on the blood plasma estradiol level and theological properties of blood in female Wistar rats after ovariectomy was investigated by measuring hematocrit, fibrinogen concentration, platelet aggregation and deformability, and the whole blood and plasma viscosity. Bilateral ovariectomy in rats led (in comparison to sham-operated animals) to a decrease in the estrogen level to 59% and produced a 5-9% increase in the whole blood viscosity, which was caused by impairment of the erythrocyte deformability and aggregation. The efficacy of oxygen transport to tissues was decreased by 4-7%. Read More

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September 2011

Development of antibodies against secoisolariciresinol--application to the immunolocalization of lignans in Linum usitatissimum seeds.

Phytochemistry 2010 Dec 1;71(17-18):1979-87. Epub 2010 Oct 1.

Université de Picardie Jules Verne, EA3900-BioPI Biologie des Plantes et contrôle des Insectes ravageurs, Faculté de Pharmacie, 1 rue des Louvels, 80037 Amiens cedex, France.

Lignans are widely distributed plant metabolites associated with a large range of biological activities. In order to gain insight into their biosynthesis and their spatio-temporal accumulation an immunological probe was developed. Secondary metabolites generally have too small molecular weight to be antigenic and have to be associated with a carrier protein. Read More

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December 2010

Metabolic engineering of lignan biosynthesis in Forsythia cell culture.

Plant Cell Physiol 2009 Dec;50(12):2200-9

Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto, Mishima, Osaka, 618-8503, Japan.

Lignans are a large class of secondary metabolites in plants, with numerous biological effects in mammals, including antitumor and antioxidant activities. Sesamin, the most abundant furofuran-class lignan in sesame seeds (Sesamum plants), is produced by the cytochrome P450 enzyme CYP81Q1 from the precursor lignan, pinoresinol. In contrast, Forsythia plants produce dibenzylbutyrolactone-class lignans, such as matairesinol, from pinoresinol via the catalysis of pinoresinol/lariciresinol reductase (PLR) and secoisolariciresinol dehydrogenase. Read More

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December 2009

Molecular cloning and characterization of a novel isoflavone reductase-like gene (FcIRL) from high flavonoids-producing callus of Fagopyrum cymosum.

Yao Xue Xue Bao 2009 Jul;44(7):809-19

Institute of Ornament Plants, College of Horticulture and Landscape, Southwest University, Chongqing 400716, China.

Lignans are important defensive compounds in plants and have good biological activities protecting human health. In order to study the medicinal secondary metabolism of Fagopyrum cymosum (Trev.) Meisn, a traditional Chinese medicine with anti-tumor effect, a novel isoflavone reductase-like gene, FcIRL, was cloned using RACE strategy from a cDNA library of high flavonoids-producing callus. Read More

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First stereoselective synthesis of meso-secoisolariciresinol and comparison of its biological activity with (+) and (-)-secoisolariciresinol.

Biosci Biotechnol Biochem 2007 Dec 7;71(12):2962-8. Epub 2007 Dec 7.

Faculty of Agriculture, Ehime University, Matsuyama, Ehime, Japan.

The first stereoselective synthesis of meso-secoisolariciresinol is reported. A comparison of the cytotoxic and immunosuppressive activity between meso-secoisolariciresinol and optically active secoisolariciresinols was similarly performed for the first time. Both enantiomers of secoisolariciresinol accelerated IgM production, although meso-secoisolariciresinol did not affect IgM production. Read More

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December 2007

High throughput quantification of phytoestrogens in human urine and serum using liquid chromatography/tandem mass spectrometry (LC-MS/MS).

J Chromatogr B Analyt Technol Biomed Life Sci 2007 Jun 18;853(1-2):138-46. Epub 2007 Mar 18.

HFL, Newmarket Road, Fordham, Cambridgeshire CB7 5WW, United Kingdom.

Phytoestrogens are currently the subject of intense study owing to their potential protective effects against a number of complex diseases. However, in order to investigate the interactions between phytoestrogens and disease state effectively, it is necessary to have analytical methods which are sensitive, reproducible, and require low sample volumes. We report an assay for three isoflavones (daidzein, genistein, and glycitein), two metabolites of daidzein (equol and O-desmethylangolensin), three lignans (secoisolariciresinol, enterodiol, and enterolactone), and one flavanone (naringenin) in human urine and serum. Read More

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Pinoresinol-lariciresinol reductases with different stereospecificity from Linum album and Linum usitatissimum.

Phytochemistry 2005 Jun;66(11):1254-63

Institut für Entwicklungs- und Molekularbiologie der Pflanzen, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, D-40225 Düsseldorf, Germany.

Recently it was found that cell cultures and plants of Linum species contain lignans of various chemical structures. The stereochemistry of these compounds differ among species. Cell cultures of L. Read More

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A semiquantitative food frequency questionnaire is a valid indicator of the usual intake of phytoestrogens by south Asian women in the UK relative to multiple 24-h dietary recalls and multiple plasma samples.

J Nutr 2005 Jan;135(1):116-23

Department of Epidemiology and Population Health, London School of Hygiene and Tropical Medicine, London WC1E 7HT, UK.

We investigated the relative validity of an interview-administered FFQ to estimate phytoestrogen intake among South Asian women in the UK. A population-based sample of 108 healthy South Asian women completed random repeated monthly 24-h recalls [with a subsample (n = 58) also providing multiple plasma samples] over a period of 1 y followed by administration of the FFQ. The FFQ produced slightly higher estimates of phytoestrogen intake than the 24-h recalls, but the percentage of women classified into the same +/- 1 quartile by the 2 methods was high for all phytoestrogens (from 81 to 94%) with only a small percentage (<5%) being misclassified into extreme opposite quartiles. Read More

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January 2005

Plant lignans in soy-based health supplements.

J Agric Food Chem 2004 Jun;52(13):4133-8

Department of Clinical Chemistry, University of Helsinki, Biomedicum, PO Box 63, 00014 Helsinki, Finland.

The presence of plant lignans in 14 different soy-based health supplements is reported here for the first time together with the analysis of the isoflavone content, for which these products are commercialized. Six plant lignans, i.e. Read More

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In vitro metabolism of plant lignans: new precursors of mammalian lignans enterolactone and enterodiol.

J Agric Food Chem 2001 Jul;49(7):3178-86

Folkhälsan Research Center and Department of Clinical Chemistry, P.O. Box 60, FIN-00014 University of Helsinki, Finland.

The metabolism of the plant lignans matairesinol, secoisolariciresinol, pinoresinol, syringaresinol, arctigenin, 7-hydroxymatairesinol, isolariciresinol, and lariciresinol by human fecal microflora was investigated to study their properties as mammalian lignan precursors. The quantitative analyses of lignan precursors and the mammalian lignans enterolactone and enterodiol were performed by HPLC with coulometric electrode array detector. The metabolic products, including mammalian lignans, were characterized as trimethylsilyl derivatives by gas chromatography-mass spectrometry. Read More

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Antioxidant Activity of Secoisolariciresinol Diglucoside-derived Metabolites, Secoisolariciresinol, Enterodiol, and Enterolactone.


Int J Angiol 2000 Oct;9(4):220-225

Department of Physiology, College of Medicine, University of Saskatchewan, Saskatoon, Saskatchewan, Canada

Secoisolariciresinol diglucoside (SDG), an antioxidant isolated from flaxseed, is metabolized to secoisolariciresinol (SECO), enterodiol (ED), and enterolactone (EL) in the body. The effectiveness of SDG in hypercholesterolemic atherosclerosis, diabetes, and endotoxic shock could be due to these metabolites. These metabolites may have antioxidant activity. Read More

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October 2000

Dose effects of flaxseed and its lignan on N-methyl-N-nitrosourea-induced mammary tumorigenesis in rats.

Nutr Cancer 1999 ;35(1):50-7

Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, ON, Canada.

Dietary supplementation with flaxseed or its lignan secoisolariciresinol diglycoside (SDG) has reduced dimethylbenz[a]anthracene-induced mammary tumor size and number in rats. The objective of this study was to determine whether flaxseed has a dose-dependent effect on N-methyl-N-nitrosourea (MNU)-induced mammary tumor promotion and whether this effect can be attributed to its SDG. Two days after injection with MNU (50 mg/kg body wt i. Read More

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February 2000

Lignan and isoflavonoid concentrations in tea and coffee.

Br J Nutr 1998 Jan;79(1):37-45

Department of Clinical Chemistry, University of Helsinki, Finland.

Tea is a beverage consumed widely throughout the world. The existence in tea of chemopreventing compounds possessing antimutagenic, anticarcinogenic and antioxidative properties has been reported. High intakes of tea and foods containing flavonoids have recently been shown to be negatively correlated to the occurrence of CHD. Read More

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January 1998

Revealing the mammalian lignan precursor secoisolariciresinol diglucoside in flax seed by ionspray mass spectrometry.

Rapid Commun Mass Spectrom 1994 Aug;8(8):595-8

Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy.

Ionspray mass spectrometry allowed the rapid detection and unambiguous identification of secoisolariciresinol diglucoside, an important mammalian lignan precursor occurring in flax seed. It was observed that this compound is embedded in a complex form, probably a complex glucoside of still undisclosed structure, among the polar solvent extractables of flax seed from which it could not be released as such without the intervention of alkaline methanolysis. Comparison of ionspray mass spectra of untreated and methanolysed flax-seed extracts confirmed methanolysis as the crucial step in setting up any further analytical or preparative procedure concerned with secoisolariciresinol diglucoside. Read More

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Detection and identification of the plant lignans lariciresinol, isolariciresinol and secoisolariciresinol in human urine.

Clin Chim Acta 1989 Apr;180(3):293-301

Department of Clinical Chemistry, University of Helsinki, Finland.

The mammalian lignans enterolactone and enterodiol are regular constituents of human urine and are excreted daily in mumol amounts. They are produced by metabolic action of intestinal bacteria from natural plant lignan precursors which are constituents of various food plants. However, natural plant lignans seem to occur very seldom in detectable amounts in human urine. Read More

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