Rye Bran Modified with Cell Wall–Degrading Enzymes Influences

Total Page:16

File Type:pdf, Size:1020Kb

Rye Bran Modified with Cell Wall–Degrading Enzymes Influences The Journal of Nutrition Nutrient Physiology, Metabolism, and Nutrient-Nutrient Interactions Rye Bran Modified with Cell Wall–Degrading Enzymes Influences the Kinetics of Plant Lignans but Not of Enterolignans in Multicatheterized Pigs Anne K Bolvig,1 Natalja P Nørskov,1 Sophie van Vliet,1 Leslie Foldager,1,2 Mihai V Curtasu,1 Mette S Hedemann,1 Jens F Sørensen,3 Helle N Lærke,1 and Knud E Bach Knudsen1 Downloaded from https://academic.oup.com/jn/article/147/12/2220/4728058 by guest on 30 September 2021 1Department of Animal Science and 2Bioinformatics Research Centre, Faculty of Science and Technology, Aarhus University, Aarhus, Denmark; and 3DuPont Industrial Biosciences, Brabrand, Denmark Abstract Background: Whole-grain intake is associated with a lower risk of chronic Western-style diseases, possibly brought about by the high concentration of phytochemicals, among them plant lignans (PLs), in the grains. Objective: We studied whether treatment of rye bran with cell wall–degrading enzymes changed the solubility and kinetics of PLs in multicatheterized pigs. Methods: Ten female Duroc 3 Danish Landrace 3 Yorkshire pigs (60.3 6 2.3 kg at surgery) fitted with permanent catheters were included in an incomplete crossover study. The pigs were fed 2 experimental diets for 1–7 d. The diets were rich in PLs and based on nontreated lignan-rich [LR; lignan concentration: 20.2 mg dry matter (DM)/kg] or enzymatically treated lignan-rich (ENZLR; lignan concentration: 27.8 mg DM/kg) rye bran. Plasma concentrations of PLs and enterolignans were quantified with the use of targeted LC-tandem mass spectrometry. Data were log transformed and analyzed with mixed-effects, 1-compartment, and asymptotic regression models. Results: The availability of PLs was 38% greater in ENZLR than in LR, and the soluble fraction of PLs was 49% in ENZLR compared with 35% in LR diets. PLs appeared in the circulation 30 min after intake of both the ENZLR and LR diets. Postprandially, consumption of ENZLR resulted in a 4-times-greater (P < 0.0001) plasma PL concentration compared with LR. The area under the curve (AUC) measured 0–360 min after ENZLR intake was ;2 times higher than after LR intake. A 1-compartment model could describe the postprandial increase in plasma concentration after ENZLR intake, whereas an asymptotic regression model described the plasma concentrations after LR intake. Despite increased available and soluble PLs, ENZLR did not increase plasma enterolignans. Conclusion: The modification of rye bran with cell wall–degrading enzymes resulted in significantly greater plasma concentrations of PLs and the 4-h AUC, particularly syringaresinol, in multicatheterized pigs. JNutr2017;147:2220–7. Keywords: lignans, cell wall–degrading enzymes, kinetics, catheterized pigs, syringaresinol Introduction disease, and type 2 diabetes, is well established and has been The link between a high intake of whole grains and a lower risk documented in a number of epidemiological studies (1–3). One of chronic Western-style diseases, including cancer, heart of the active components that may play a role in the health- beneficial properties of whole grains and their consumption is Funding was provided by Innovation Fund Denmark (ELIN: 0603-00580B). the lignans. Lignans are diphenolic compounds found in high Author disclosures: AKB, NPN, SvV, LF, MVC, MSH, JFS, HNL, and KEBK, no conflicts of interest. concentrations in such common foods as seeds, grains, berries, Supplemental Tables 1–6 are available from the ‘‘Online Supporting Material’’ and vegetables (4–6). As concerns cereal grains, the concentra- link in the online posting of the article and from the same link in the online table of contents at http://jn.nutrition.org. tion of lignans is higher in rye than in wheat, oats, and barley (5), Address correspondence to AKB (e-mail: [email protected]). and the lignan content in grain is found mainly in the outer bran Abbreviations used: DM, dry matter; End, enterodiol; Enl, enterolactone; ENZLR, layer (pericarp or testa and aleurone) (7, 8). enzymatically treated lignan-rich diet; Hydr, 7-hydroxymatairesinol; I-Lari, iso-lariciresinol; Lari, lariciresinol; LR, lignan-rich diet; Mata, matairesinol; Med, medioresinol; Pino, pinoresinol; Commonly identified plant lignans (PLs) are matairesinol PL, plant lignan; PLOther, plant lignans other than Syr; PLTotal, total plant lignans; SDG, (Mata), pinoresinol (Pino), medioresinol (Med), lariciresinol (Lari), secoisolariciresinol diglycoside; Seco, secoisolariciresinol; Syr, syringaresinol; WO, washout. iso-lariciresinol (I-Lari), syringaresinol (Syr), secoisolariciresinol ã 2017 American Society for Nutrition. 2220 Manuscript received July 18, 2017. Initial review completed August 18, 2017. Revision accepted September 12, 2017. First published online October 4, 2017; doi: https://doi.org/10.3945/jn.117.258483. (Seco), and the glycosylated form of Seco, secoisolariciresinol The pigs were transferred to individual pens (1.25 3 3.75 m) without diglycoside (SDG). Absorption of PLs has not been well charac- bedding material but with elevated plastic grids, which allowed the pigs terized; however, recent studies in rats (9) and pigs (10), along to rest and remain dry. The pigs were acclimatized for 4 d before being with studies in humans, fed a lignan-rich (LR) diet or a single surgically fitted with permanent catheters in the portal and hepatic veins dose of SDG (11, 12) have shown rapid postprandial absorption and in the mesenteric artery. A flow probe was fitted around the portal vein (17), but because of technical problems, flow probe data were not of PLs and reported peak concentrations within 0–2.5 h from included in the present study. intake. The rapid absorption implies that part of the PLs is The pigs had a 7–9-d recovery period after the surgery, at which time absorbed from the small intestine to the circulation, which is the pigs entered the experimental period. Originally, the study was in contrast to the enterolignans [enterodiol (End) and enterolactone designed as a crossover study; however, because of the malfunctioning (Enl)], which are produced by the gut microbiota and are absorbed catheters, the crossover was not completed and the experiment was mainly from the large intestine (13). terminated on day 16. The pigs were fed the WO diet on days 1–4. This The lignans in cereals are concentrated to a large extent in the was followed by intake of one of the LR diets (LR or ENZLR) on days dietary fiber–rich outer bran fraction, which also contains a high 5–11. On days 12–15, the WO was fed again, and on the last day of the concentration of other phenolic compounds. Bioprocessing with experimental period (day 16), the pigs were fed the LR diet (LR or xylanases alone or in combination with arabinofuranosidase has ENZLR) that was not fed on days 5–11. Ten pigs completed the been shown to make a substantial part of the insoluble ferulic postprandial profile conducted on days 5 and 16 on each diet, whereas Downloaded from https://academic.oup.com/jn/article/147/12/2220/4728058 by guest on 30 September 2021 5 pigs/diet completed days 5–11 during which the samples collected acid available for absorption in the small intestine (14). Further- when the pigs were feed deprived were sampled. The experiment was more, enzymatic treatment with xylanases has resulted in the terminated after the postprandial profile was completed on day 16. enrichment of PLs in soluble rye bran extract (15). The effect of The pigs were offered water ad libitum and were allowed physical enzyme modification of the lignan source has not been investi- and visual contact through the railings of the pens. The pigs were gated in vivo, however, and its influence on the kinetic param- weighed 1 time/wk, and an iron supplement (400 mg; Uniferon, eters is unknown. Pharmacosmos) was administered intramuscularly weekly and addi- We hypothesized that the treatment of rye bran with cell tionally on profile days. wall–degrading enzymes would result in the increased solubili- Blood samples were collected (0 min) from the catheters of feed- zation of PLs, which would lead to an altered absorption kinetic. deprived pigs on days 5–16. On days 5 and 16, additional postprandial The aim of the present study was to investigate the absorption blood samples were collected at 30, 60, 120, 180, 240, 300, and 360 min relative to the morning meal. On days 12–15, a single sample was and elimination kinetics of PLs upon intake of an LR diet collected 360 min after the morning meal in addition to the 0-min sample modified with a cocktail of cell wall–degrading enzymes: xylanases, taken after feed deprivation for 12 h. After sampling was completed, the b -glucanases, and cellulases. The enzyme-modified rye bran or indwelling catheters were treated as described by Ingerslev et al. (16). nontreated rye bran was incorporated into a low-lignan wheat Blood samples were collected into sodium heparin Vacutainers (Becton- flour–based diet replacing refined wheat–concentrated fiber at an Dickinson), centrifuged at 2000 3 g for 10 min at 4°C, and plasma was iso-dietary fiber level. The effect of the enzyme treatment was stored at 280°C until analysis. Hematocrit levels were measured on days assessed in terms of absorption kinetic consequences for PLs and 5, 12, and 16. The pigs were killed with an overdose of sodium enterolignans in a catheterized pig model. pentobarbital followed by exsanguination (18). The animal experiment was conducted according to the protocols approved by the Danish Animal Experiments Inspectorate and complied with the guidelines of the Ministry of Food, Agriculture, and Fisheries concerning animal Methods experiments and the care of animals under study. Diets Analytical methods Three experimental diets were produced: a washout (WO) diet low in PLs Chemical analyses of the diets were performed in duplicate on freeze- based on white wheat flour supplemented with purified wheat fiber (Vitacel dried samples.
Recommended publications
  • Dr. Duke's Phytochemical and Ethnobotanical Databases List of Chemicals for Lyme Disease (Chronic)
    Dr.
    [Show full text]
  • Chemical Structures of Lignans and Neolignans Isolated from Lauraceae
    Review Chemical Structures of Lignans and Neolignans Isolated from Lauraceae Ya Li 1,*, Shuhan Xie 2, Jinchuan Ying 1, Wenjun Wei 1 and Kun Gao 1,* 1 State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China; [email protected] (J.Y.); [email protected] (W.W.) 2 Lanzhou University High School, Lanzhou 730000, China; [email protected] * Correspondences: [email protected] (Y.L.); [email protected] (K.G.); Tel.: +86-931-8912500 (Y.L.) Academic Editor: David Barker Received: 09 November 2018; Accepted: 29 November 2018; Published: 30 November 2018 Abstract: Lauraceae is a good source of lignans and neolignans, which are the most chemotaxonomic characteristics of many species of the family. This review describes 270 naturally occurring lignans and neolignans isolated from Lauraceae. Keywords: lignans; neolignans; Lauraceae; chemical components; chemical structures 1. Introduction Lignans are widely distributed in the plant kingdom, and show diverse pharmacological properties and a great number of structural possibilities. The Lauraceae family, especially the genera of Machilus, Ocotea, and Nectandra, is a rich source of lignans and neolignans, and neolignans represent potential chemotaxonomic significance in the study of the Lauraceae. Lignans and neolignans are dimers of phenylpropane, and conventionally classified into three classes: lignans, neolignans, and oxyneolignans, based on the character of the C–C bond and oxygen bridge joining the two typical phenyl propane units that make up their general structures [1]. Usually, lignans show dimeric structures formed by a β,β’-linkage (8,8’-linkage) between two phenylpropanes units. Meanwhile, the two phenylpropanes units are connected through a carbon–carbon bond, except for the 8,8’-linkage, which gives rise to neolignans.
    [Show full text]
  • Redalyc.Chemical Constituents from Zanthoxylum Setulosum (Rutaceae)
    Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas ISSN: 0717-7917 [email protected] Universidad de Santiago de Chile Chile MORA, Soledad; CASTRO, Víctor; POVEDA, Luis; CHAVARRÍA, Max; MURILLO, Renato Chemical constituents from Zanthoxylum setulosum (Rutaceae) Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas, vol. 10, núm. 2, marzo, 2011, pp. 155-158 Universidad de Santiago de Chile Santiago, Chile Available in: http://www.redalyc.org/articulo.oa?id=85617384009 How to cite Complete issue Scientific Information System More information about this article Network of Scientific Journals from Latin America, the Caribbean, Spain and Portugal Journal's homepage in redalyc.org Non-profit academic project, developed under the open access initiative © 2011 The Authors © 2011 Boletín Latinoamericano y del Caribe de Plantas Medicinales y Aromáticas 10 (2): 155 - 158 BLACPMA ISSN 0717 7917 Artículo Original | Original Article Chemical constituents from Zanthoxylum setulosum (Rutaceae) [Costituyentes químicos de Zanthoxylum setulosum (Rutaceae)] Soledad MORA1, Víctor CASTRO1, Luis POVEDA2, Max CHAVARRÍA1 & Renato MURILLO1 1Escuela de Química and CIPRONA, Universidad de Costa Rica, 2060, San José, Costa Rica. 2Escuela de Ciencias Ambientales, Facultad de Ciencias de la Tierra y el Mar, Universidad Nacional, 3000, Costa Rica. Contactos | Contacts: Max CHAVARRIA E-mail address [email protected] Abstract Following our phytochemical studies of Costa Rican plants, in this work we report the isolation and identification of eight compounds from aerial parts of Zanthoxylum setulosum (Rutaceae). They were identified as the alkaloid skimmianine, the lignans savinin, kusunokinin, sesamin, syringaresinol and the isopentenyl ether of pluviatol, the amide aurantiamide acetate, and the triterpen lupeol.
    [Show full text]
  • Therapeutic Applications of Compounds in the Magnolia Family
    Pharmacology & Therapeutics 130 (2011) 157–176 Contents lists available at ScienceDirect Pharmacology & Therapeutics journal homepage: www.elsevier.com/locate/pharmthera Associate Editor: I. Kimura Therapeutic applications of compounds in the Magnolia family Young-Jung Lee a, Yoot Mo Lee a,b, Chong-Kil Lee a, Jae Kyung Jung a, Sang Bae Han a, Jin Tae Hong a,⁎ a College of Pharmacy and Medical Research Center, Chungbuk National University, 12 Gaesin-dong, Heungduk-gu, Cheongju, Chungbuk 361-763, Republic of Korea b Reviewer & Scientificofficer, Bioequivalence Evaluation Division, Drug Evaluation Department Pharmaceutical Safety Breau, Korea Food & Drug Administration, Republic of Korea article info abstract Keywords: The bark and/or seed cones of the Magnolia tree have been used in traditional herbal medicines in Korea, Magnolia China and Japan. Bioactive ingredients such as magnolol, honokiol, 4-O-methylhonokiol and obovatol have Magnolol received great attention, judging by the large number of investigators who have studied their Obovatol pharmacological effects for the treatment of various diseases. Recently, many investigators reported the Honokiol anti-cancer, anti-stress, anti-anxiety, anti-depressant, anti-oxidant, anti-inflammatory and hepatoprotective 4-O-methylhonokiol effects as well as toxicities and pharmacokinetics data, however, the mechanisms underlying these Cancer Nerve pharmacological activities are not clear. The aim of this study was to review a variety of experimental and Alzheimer disease clinical reports and, describe the effectiveness, toxicities and pharmacokinetics, and possible mechanisms of Cardiovascular disease Magnolia and/or its constituents. Inflammatory disease © 2011 Elsevier Inc. All rights reserved. Contents 1. Introduction .............................................. 157 2. Components of Magnolia ........................................ 159 3. Therapeutic applications in cancer ...................................
    [Show full text]
  • 1.25 Lignans: Biosynthesis and Function
    1.25 Lignans: Biosynthesis and Function NORMAN G. LEWIS and LAURENCE B. DAVIN Washington State University, Pullman, WA, USA 0[14[0 INTRODUCTION 539 0[14[1 DEFINITION AND NOMENCLATURE 539 0[14[2 EVOLUTION OF THE LIGNAN PATHWAY 531 0[14[3 OCCURRENCE 534 0[14[3[0 Li`nans in {{Early|| Land Plants 534 0[14[3[1 Li`nans in Gymnosperms and An`iosperms "General Features# 536 0[14[4 OPTICAL ACTIVITY OF LIGNAN SKELETAL TYPES AND LIMITATIONS TO THE FREE RADICAL RANDOM COUPLING HYPOTHESIS 536 0[14[5 707? STEREOSELECTIVE COUPLING] DIRIGENT PROTEINS AND E!CONIFERYL ALCOHOL RADICALS 541 0[14[5[0 Diri`ent Proteins Stipulate Stereoselective Outcome of E!Coniferyl Alcohol Radical Couplin` in Pinoresinol Formation 541 0[14[5[1 Clonin` of the Gene Encodin` the Diri`ent Protein and Recombinant Protein Expression in Heterolo`ous Systems 543 0[14[5[2 Sequence Homolo`y Comparisons 543 0[14[5[3 Comparable Systems 543 0[14[5[4 Perceived Biochemical Mechanism of Action 546 0[14[6 PINORESINOL METABOLISM AND ASSOCIATED METABOLIC PROCESSES 547 0[14[6[0 Sesamum indicum] "¦#!Piperitol\ "¦#!Sesamin\ and "¦#!Sesamolinol Synthases 547 0[14[6[1 Magnolia kobus] Pinoresinol and Pinoresinol Monomethyl Ether O!Methyltransferase"s# 550 0[14[6[2 Forsythia intermedia and Forsythia suspensa 551 0[14[6[2[0 "¦#!Pinoresinol:"¦#!lariciresinol reductase 552 0[14[6[2[1 "−#!Secoisolariciresinol dehydro`enase 554 0[14[6[2[2 Matairesinol O!methyltransferase 556 0[14[6[3 Linum usitatissimum] "−#!Pinoresinol:"−#!Lariciresinol Reductase and "¦#!Secoisolariciresinol Glucosyltransferase"s# 557
    [Show full text]
  • Determinants of Dietary Lignan Intake in a Representative Sample of Young Spaniards: Association with Lower Obesity Prevalence Among Boys but Not Girls
    European Journal of Clinical Nutrition (2012) 66, 795–798 & 2012 Macmillan Publishers Limited All rights reserved 0954-3007/12 www.nature.com/ejcn ORIGINAL ARTICLE Determinants of dietary lignan intake in a representative sample of young Spaniards: association with lower obesity prevalence among boys but not girls JL Pen˜ alvo1, B Moreno-Franco1, L Ribas-Barba2 and L Serra-Majem2,3 BACKGROUND/OBJECTIVES: Lignan-rich diets have been associated with favorable health effects through improved metabolic profile. In this study, we hypothesized that dietary lignan intake could be also associated with childhood obesity. SUBJECTS/METHODS: We studied prevalent obesity in relation to lignan intake within the enKid study that involved 3438 children, adolescents and young adults (2–24 years old). Participant’s dietary records were used to calculate lignan dietary intake using a lignan composition database adapted to the Spanish diet. RESULTS: The mean intake of the dietary lignans was calculated as B1 mg/day, corresponding mainly (37%) to pinoresinol. No gender differences were found, but lignan intake was positively associated with age, physical activity level and dietary fiber intake, and negatively with the intake of polyunsaturated and saturated fatty acids. The main sources of dietary lignans were refined wheat, olive oil and whole-wheat bread. A strong association between dietary lignan intake and prevalent obesity was found only for boys, with odds ratio (highest versus lowest quartile of lignan intake) of 0.34 (95% confidence interval, 0.17–0.70) after adjusting for main confounders, including dietary fiber. CONCLUSIONS: Boys with the highest lignan-rich products including cereals, whole-grain products and olive oil, presented less cases of obesity in this representative sample of Spanish children and adolescents.
    [Show full text]
  • WO 2018/002916 Al O
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2018/002916 Al 04 January 2018 (04.01.2018) W !P O PCT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C08F2/32 (2006.01) C08J 9/00 (2006.01) kind of national protection available): AE, AG, AL, AM, C08G 18/08 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, (21) International Application Number: DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, PCT/IL20 17/050706 HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, (22) International Filing Date: KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, 26 June 2017 (26.06.2017) MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (25) Filing Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 246468 26 June 2016 (26.06.2016) IL kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, (71) Applicant: TECHNION RESEARCH & DEVEL¬ UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, OPMENT FOUNDATION LIMITED [IL/IL]; Senate TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, House, Technion City, 3200004 Haifa (IL).
    [Show full text]
  • Bioavailability of Lignans in Human Subjects
    Nutrition Research Reviews (2006), 19, 187–196 DOI: 10.1017/NRR2006129 q The Authors 2006 Bioavailability of lignans in human subjects Thomas Clavel1,2, Joe¨l Dore´2 and Michael Blaut1* 1Department of Gastrointestinal Microbiology, Institute of Human Nutrition Potsdam-Rehbru¨cke, Arthur-Scheunert-Allee 155, 14558 Nuthetal, Germany 2Unit of Ecology and Physiology of the Digestive Tract, National Institute for Research in Agriculture, Jouy-en-Josas, France 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. Phyto-oestrogens: Lignans: Enterolignans: Bioavailability: Human intestinal microbiota Introduction enterodiol (ED) and enterolactone (EL) (Borriello et al. 1985), the biological properties of which are proposed to be Phyto-oestrogens are dietary compounds of plant origin that more potent than those of plant lignans (Brooks & mainly include flavonoids and lignans. Since their chemical Thompson, 2005; Jacobs et al. 2005). Numerous data structure is similar to those of oestrogens, they have been presented in the present review deal primarily with SDG. studied for their involvement in hormone-related disorders, However, it must be emphasised that enterolignans are such as reproductive failure and breast cancer (Setchell & produced from plant lignans other than SDG and Adlercreutz, 1988). Meanwhile, it has become clear that it is MAT (Axelson et al.
    [Show full text]
  • The Lignan Macromolecule from Flaxseed Structure and Bioconversion of Lignans
    The lignan macromolecule from flaxseed Structure and bioconversion of lignans Karin Struijs Promotor: Prof. Dr. Ir. H. Gruppen Hoogleraar Levensmiddelenchemie Wageningen Universiteit Co-promotor: Dr. Ir. J.-P. Vincken Universitair docent, leerstoelgroep Levensmiddelenchemie Wageningen Universiteit Promotiecommissie: Prof. Dr. R.F. Witkamp Wageningen Universiteit Prof. M. Blaut German Institute of Human Nutrition Potsdam-Rehbruecke Dr. A. Kamal-Eldin Swedish University of Agricultural Sciences, Uppsala Dr. Ir. P.C.H. Hollman RIKILT-Instituut voor Voedselveiligheid, Wageningen Dit onderzoek is uitgevoerd binnen de onderzoeksschool VLAG (Voeding, Levensmiddelentechnologie, Agrobiotechnologie en Gezondheid). The lignan macromolecule from flaxseed Structure and bioconversion of lignans Karin Struijs Proefschrift Ter verkrijging van de graad van doctor op gezag van de rector magnificus van Wageningen Universiteit, Prof. Dr. M.J. Kropff in het openbaar te verdedigen op maandag 17 november 2008 des namiddags te vier uur in de Aula. Struijs, Karin The lignan macromolecule from flaxseed Structure and bioconversion of lignans Ph.D. thesis Wageningen Universiteit, The Netherlands, 2008 ISBN: 978-90-8585-247-6 _________________________________________________________________________________________________________________ Abstract Lignans are diphenolic compounds, which are of interest because of their positive health effects. The aims of the research described in this thesis are to identify the precise composition and structure of the lignan macromolecule from flaxseeds, to convert plant lignans into the bioactive mammalian lignans by fermentation, and to investigate how the bioconversion of lignans influences their estrogenicity. In order to be able to reach these goals, analytical and preparative protocols were developed. The lignan macromolecule from flaxseed was found to consist of mainly secoisolariciresinol diglucoside (SDG) ester-linked via 3-hydroxy-3-methylglutaric acid (HMGA).
    [Show full text]
  • Lignan Natural Products Baran Group Meeting November 18, 2005 Mike Demartino
    Lignan Natural Products Baran Group Meeting November 18, 2005 Mike DeMartino -Classification of lignan natural products: -Biosynthesis: Ar O -This topic nicely bridges two other Baran Group meeting topics, meaning Ar OH Ar O O O Ar that these will not be detailed in this lecture. In the most general sense, Ar' OH Ar' O Ar' the biosynthesis if lignans can be thought of as such: Ar' dibenzylbutan(diol)e tetrahydrofuran tetrahydrofuran dibenzylbutyrolactone Carbohydrates --> Shikimic acid pathway --> Aromatic a.a.'s --> Cinnamic acids --> Lignans (Steganes) OH OH O O RO See Group Meeting: See Group Meeting: Ambhaikar, (2005) Zografos, (2004) RO O O RO O http://www.scripps.edu/chem/baran/html/meetingschedule.html O R'O Ar Ar CO2H CO2H tetralin naphthalene dibenzocyclooctadiene NH2 (stegane) cinnamic -Provisional statement acid Lignans are an extremely large class of natural products; for reasons detailed below, this lecture will focus on (bio)synthesis. That said, L-Phe O2 Shikimic NADPH neolignans (see next page) will not be discussed in detail. This is not Acid meant to give a comprehensive coverage of all synthetic routes to CO2H CO2H CO2H CO2H CO2H CO2H lignans, but rather a representitive sampling thereof. NH 2 O O 2 SAM 2 -Pharmacological properties NADPH NADPH SAM Because of the high structural diversity of this class of natural HO MeO MeO OH MeO OMe products, there is obviously an extraordinary range of medicinal OH OH OH OH OH OH properties and this area continues to be a fruitful research topic. L-Tyr 4-coumaric acid caffeic ferulic sinapic Many lignan containing plants have been used for centuries, (p-coumaric acid) acid acid acid particualrly in Asian communities, as cures and remedies for various ailments.
    [Show full text]
  • Effect of Thermal Heating on Some Lignans in Flax Seeds, Sesame
    Food Chemistry 138 (2013) 1847–1855 Contents lists available at SciVerse ScienceDirect Food Chemistry journal homepage: www.elsevier.com/locate/foodchem Analytical Methods Effect of thermal heating on some lignans in flax seeds, sesame seeds and rye ⇑ Eva Gerstenmeyer a, Sigrid Reimer a, Emmerich Berghofer b, Heidi Schwartz a,1, Gerhard Sontag a, a Institute for Analytical Chemistry, University of Vienna, Währinger Straße 38, A-1090 Vienna, Austria b Department of Food Science and Technology, University of Natural Resources and Life Sciences, Muthgasse 18, A-1190 Vienna, Austria article info abstract Article history: Consumption of lignan rich food is presumed to have positive effects on human health. As numerous Received 12 April 2012 foods are consumed mainly in processed form it is important to investigate the changes of the lignan con- Received in revised form 4 November 2012 tent during processing. To this end, unheated and heated sesame seeds, sesame products, rye grains, rye Accepted 20 November 2012 flour, rye bread and flax seeds were extracted by sonication with ethanol/water (70:30, v:v) or sodium Available online 5 December 2012 methoxide. The extracts were additionally hydrolysed enzymatically (b-glucuronidase/arylsulphatase, cellulase), the compounds separated on a reversed phase column by gradient elution and detected by Keywords: UV/ESI-MS in the negative ionisation multiple reaction monitoring mode (MRM). Secoisolariciresinol, lar- HPLC/UV–ESI-MS analysis iciresinol, pinoresinol, 7-hydroxymatairesinol, syringaresinol, isolariciresinol, secoisolariciresinol digly- Lignans Heated rye coside, lariciresinol monoglycoside, pinoresinol mono-, di- and triglycoside, sesaminol, sesaminol Sesame seeds triglycoside, sesamolinol and sesamolinol diglycoside were identified. Flax seeds Moderate heating at 100 °C did not degrade the lignan aglycones and glycosides in dry foods.
    [Show full text]
  • Targeted LC-MSMS Lignans Targeted .PDF
    Article pubs.acs.org/JAFC Targeted LC-MS/MS Method for the Quantitation of Plant Lignans and Enterolignans in Biofluids from Humans and Pigs † § § † † Natalja P. Nørskov,*, Anja Olsen, Anne Tjønneland, Anne Katrine Bolvig, Helle Nygaard Lærke, † and Knud Erik Bach Knudsen † Department of Animal Science, Aarhus University, AU-Foulum, Blichers Alle 20, P.O. Box 50, DK-8830 Tjele, Denmark § Danish Cancer Society Research Center, Strandboulevarden 49, DK-2100 Copenhagen, Denmark ABSTRACT: Lignans have gained nutritional interest due to their promising role in the prevention of lifestyle diseases. However, epidemiological studies are in need of more evidence to link the intake of lignans to this promising role. In this context, it is necessary to study large population groups to obtain sufficient statistical power. Therefore, there is a demand for fast, sensitive, and accurate methods for quantitation with high throughput of samples. This paper presents a validated LC-MS/MS method for the quantitation of eight plant lignans (matairesinol, hydroxymatairesinol, secoisolariciresinol, lariciresinol, isolariciresinol, syringaresinol, medioresinol, and pinoresinol) and two enterolignans (enterodiol and enterolactone) in both human and pig plasma and urine. The method showed high selectivity and sensitivity allowing quantitation of lignans in the range of 0.024−100 ng/mL and with a run time of only 4.8 min per sample. The method was successfully applied to quantitate lignans in biofluids from ongoing studies with humans and pigs. KEYWORDS: plant lignans, enterolignans, LC-MS/MS, plasma, urine, pigs, humans ■ INTRODUCTION ■ MATERIALS AND METHODS Plant lignans are present in a variety of foods consumed by Materials. Acetonitrile and methanol were obtained from mammals: cereals, vegetables, and fruits.1 When ingested, plant Fluka/Sigma-Aldrich (St.
    [Show full text]