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Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats

Published online by Cambridge University Press:  09 March 2007

Jan Frank ,
Christina Eliasson ,
Diane Leroy-Nivard ,
Alicja Budek ,
Torbjörn Lundh ,
Bengt Vessby ,
Per Åman  and
Afaf Kamal-Eldin
Jan Frank*
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
Christina Eliasson
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
Diane Leroy-Nivard
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
Alicja Budek
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
Torbjörn Lundh
Affiliation:
Department of Animal Nutrition and Management, Swedish University of Agricultural Sciences (SLU), 750 07 Uppsala, Sweden
Bengt Vessby
Affiliation:
Department of Public Health and Caring Sciences and Unit for Clinical Nutrition Research, Uppsala University, 751 25 Uppsala, Sweden
Per Åman
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
Afaf Kamal-Eldin
Affiliation:
Department of Food Science, Swedish University of Agricultural Sciences (SLU), Box 7051, S-750 07 Uppsala, Sweden
*
*Corresponding author: fax +46 18 67 29 95, Email Jan.Frank@lmv.slu.se
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Abstract

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Secoisolariciresinol diglucoside (SDG) is an important dietary lignan that is found at very high levels in flaxseed (1–4%, w/w). Flaxseed lignans have received much research interest in recent years because of reported phyto-oestrogenic, anticarcinogenic, and anti-atherogenic effects. Previously, flaxseed feeding has been shown to decrease vitamin E concentrations in rats despite the antioxidant potential of SDG in vitro. Sesamin, a sesame lignan, on the other hand has been shown to increase vitamin E concentrations in rats. The aim of the present study was to investigate the effect of dietary SDG and its oligomers on vitamin E and cholesterol concentrations in rats. SDG was extracted from defatted flaxseed flour with a dioxane–ethanol mixture and purified by silica column chromatography. The major oligomers with 3-hydroxy-3-methyl glutaric acid, containing a high ratio of SDG to p−coumaric and ferulic acid glucosides, were purified from the extracts by reversed-phase liquid chromatography. When fed to rats at 0·1% in the diet for 27%, both SDG and its oligomers had no effect on animal performance but caused an increase in liver cholesterol and a 2-fold reduction in the levels of α- and γ-tocopherols in rat plasma and liver. It is notable that a phenolic antioxidant, such as SDG, causes a vitamin E-lowering effect in rats. This cannot be explained at present, but warrants further investigations with respect to the magnitude, mechanism, and significance of the observed effect for human nutrition.

Keywords

FlaxseedSecoisolariciresinol diglucosideEnterodiolVitamin ECholesterol
Type
Research Article
Information
British Journal of Nutrition , Volume 92 , Issue 1 , July 2004 , pp. 169 - 176
Copyright
Copyright © The Nutrition Society 2004

References

1Adlercreutz, H, Fotsis, T, Bannwart, C, Wahala, K, Makela, T, Brunow, G & Hase, TDetermination of urinary lignans and phytoestrogen metabolites, potential antiestrogens and anticarcinogens, in urine of women on various habitual diets. J Steroid Biochem 1986 25, 791–797.Google Scholar
2Adlercreutz, H, Fotsis, T, Heikkinen, R, Dwyer, JT, Woods, M, Goldin, BR & Gorbach, SLExcretion of the lignans enterolactone and enterodiol and of equol in omnivorous and vegetarian postmenopausal women and in women with breast cancer. Lancet 1982 ii, 1295–1299.CrossRefGoogle Scholar
3Axelson, M & Setchell, KDThe excretion of lignans in rats – evidence for an intestinal bacterial source for this new group of compounds. FEBS Lett 1981 123, 337–342.CrossRefGoogle ScholarPubMed
4Axelson, M, Sjovall, J, Gustafsson, BE & Setchell, KDOrigin of lignans in mammals and identification of a precursor from plants. Nature 1982 298, 659–660.CrossRefGoogle ScholarPubMed
5Bakke, JE & Klosterman, HJA new diglucoside from flaxseed. Proc North Dakota Acad Sci 1956 10, 18–22.Google Scholar
6Bambagiotti-Alberti, M, Coran, SA, Ghiara, C, Giannellini, V & Raffaelli, ARevealing the mammalian lignan precursor secoisolariciresinol diglucoside in flax seed by ionspray mass spectrometry. Rapid Commun Mass Spectrom 1994 a 8, 595–598.Google Scholar
7Bambagiotti-Alberti, M, Coron, SA, Ghiara, C, Moreti, G & Raffaelli, AInvestigation of mammalian lignan precursors in flax seed: first evidence of secoisolariciresinol diglucoside in two isomeric forms by liquid chromatograph/mass spectrometry. Rapid Commun Mass Spectrom 1994 b 8, 929–932.CrossRefGoogle ScholarPubMed
8Borriello, SP, Setchell, KD, Axelson, M & Lawson, AMProduction and metabolism of lignans by the human faecal flora. J Appl Bacteriol 1985 58, 37–43.CrossRefGoogle ScholarPubMed
9Eliasson, C, Kamal-Eldin, A, Andersson, R & Åman, PHPLC analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction. J Chromatogr 2003 1012A, 151–159.CrossRefGoogle Scholar
10Ford, JD, Huang, KS, Wang, HB, Davin, LB & Lewis, NGBiosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed. J Nat Prod 2001 64, 1388–1397.Google Scholar
11Frank, J, Kamal-Eldin, A, Lundh, T, Määttä, K, Törrönen, R & Vessby, BEffects of dietary anthocyanins on tocopherols and lipids in rats. J Agric Food Chem 2002 50, 7226–7230.Google Scholar
12Frank, J, Kamal-Eldin, A, Razdan, A, Lundh, T & Vessby, BThe dietary hydroxycinnamate caffeic acid and its conjugate chlorogenic acid increase vitamin E and cholesterol concentrations in Sprague-Dawley rats. J Agric Food Chem 2003 a 51, 2526–2531.Google Scholar
13Frank, J, Lundh, T, Parker, RS, Swanson, JE, Vessby, B & Kamal-Eldin, Aietary (+)-catechin and BHT markedly increase alpha-tocopherol concentrations in rats by a tocopherol-omega-hydroxylase-independent mechanism. J Nutr 2003 b 133, 3195–3199.Google Scholar
14Gurbay, A, Gonthier, B, Daveloose, D, Favier, A & Hincal, FMicrosomal metabolism of ciprofloxacin generates free radicals. Free Radic Biol Med 2001 30, 1118–1121.CrossRefGoogle ScholarPubMed
15Hara, A & Radin, NSLipid extraction of tissues with a low-toxicity solvent. Anal Biochem 1978 90, 420–426.Google Scholar
16Hensley, K, Benaksas, EJ & Bolli, RNew perspectives on vitamin E: gamma-tocopherol and carboxyethylhydroxychroman metabolites in biology and medicine. Free Radic Biol Med 2004 36, 1–15.CrossRefGoogle ScholarPubMed
17Jacobs, E & Metzler, MOxidative metabolism of the mammalian lignans enterolactone and enterodiol by rat, pig, and human liver microsomes. J Agric Food Chem 1999 47, 1071–1077.CrossRefGoogle ScholarPubMed
18Jenab, M & Thompson, LUThe influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity. Carcinogenesis 1996 17, 1343–1348.Google Scholar
19Johnsson, P, Kamal-Eldin, A, Lundgren, LN & Aman, PHPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds. J Agric Food Chem 2000 48, 5216–5219.CrossRefGoogle ScholarPubMed
20Johnsson, P, Peerlkamp, N, Kamal-Eldin, A, Andersson, RE, Andersson, R, Lundgren, LN & Åman, PPolymeric fractions containing phenol glucosides in flaxseed. Food Chem 2001 76, 207–212.CrossRefGoogle Scholar
21Kamal-Eldin, A, Frank, J, Razdan, A, Tengblad, S, Basu, S & Vessby, BEffects of dietary phenolic compounds on tocopherol, cholesterol, and fatty acids in rats. Lipids 2000 35, 427–435.Google Scholar
22Kamal-Eldin, A, Peerlkamp, N, Johnsson, P, Andersson, R, Andersson, RE, Lundgren, LN & Aman, PAn oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues. Phytochemistry 2001 58, 587–590.CrossRefGoogle ScholarPubMed
23Klosterman, HJ & Smith, FThe isolation of β-hydroxy-β-methylglutaric acid from the seed of flax ( Linum usitatissimum). J Am Chem Soc 1954 76, 1229–1230.Google Scholar
24Klosterman, HJ, Smith, F & Clagett, COThe constitution of linocinnamarin. J Am Chem Soc 1955 77, 420–421.Google Scholar
25Laurenti, O, Albi, F, Artini, M, Bravi, C, Hurd, R & Demattia, GEffects of HMGA in non-insulin-dependent diabetics with secondary dyslipidemia. Clin Trials J 1990 27, 149–154.Google Scholar
26Liggins, J, Grimwood, R & Bingham, SAExtraction and quantification of lignan phytoestrogens in food and human samples. Anal Biochem 2000 287, 102–109.Google Scholar
27Mazur, W & Adlercreutz, HNatural and anthropogenic environmental oestrogens: the scientific basis for risk assessment. Naturally occuring oestrogens in food. Pure Appl Chem 1998 70, 1759–1776.CrossRefGoogle Scholar
28Meagher, LP, Beecher, GR, Flanagan, VP & Li, BWIsolation and characterization of the lignans, isolariciresinol and pinoresinol, in flaxseed meal. J Agric Food Chem 1999 47, 3173–3180.CrossRefGoogle ScholarPubMed
29Nenadis, N, Zhang, HY & Tsimidou, MZStructure-antioxidant activity relationship of ferulic acid derivatives: effect of carbon side chain characteristic groups. J Agric Food Chem 2003 51, 1874–1879.CrossRefGoogle ScholarPubMed
30Nesbitt, PD, Lam, Y & Thompson, LUHuman metabolism of mammalian lignan precursors in raw and processed flaxseed. Am J Clin Nutr 1999 69, 549–555.Google Scholar
31Niemeyer, HB & Metzler, MOxidative metabolites and genotoxic potential of mammalian and plant lignans in vitro. J Chromatogr 2002 777, 321–327.Google Scholar
32Paolini, M, Antelli, A, Pozzetti, L, Spetlova, D, Perocco, P, Valgimigli, L, Pedulli, GF & Cantelli-Forti, GInduction of cytochrome P450 enzymes and over-generation of oxygen radicals in beta-carotene supplemented rats. Carcinogenesis 2001 22, 1483–1495.Google Scholar
33Prasad, KHydroxy radical scavenging property of secoisolariciresinol diglucoside (SDG) isolated from flaxseed. Mol Cell Biochem 1997 168, 117–123.Google Scholar
34Prasad, KReduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Circulation 1999 99, 1355–1362.Google Scholar
35Prasad, K, Mantha, SV, Muir, AD & Westcott, NDReduction of hypercholesterolemic atherosclerosis by CDC-flaxseed with very low alpha-linolenic acid. Atherosclerosis 1998 136, 367–375.CrossRefGoogle ScholarPubMed
36Qui, SX, Lu, ZZ, Luyengi, L, Lee, SK, Pezzuto, JM, Farnsworth, NR, Thompson, LU & Fong, HHSIsolation and characterization of flaxseed (Linum usitatissimum) constituents. Pharm Biol 1999 37, 1–7.Google Scholar
37Ratnayake, WMN, Behrens, WA, Fischer, PWF, L'Abbé, MR, Mongeau, R & Beare-Rogers, JLChemical and nutritional studies of flaxseed (variety Linott) in rats. J Nutr Biochem 1992 3, 232–240.CrossRefGoogle Scholar
38Rickard, SE & Thompson, LUChronic exposure to secoisolariciresinol diglycoside alters lignan disposition in rats. J Nutr 1998 128, 615–623.Google Scholar
39Seigler, L & Wu, WTSeparation of serum high-density lipoprotein for cholesterol determination: ultracentrifugation vs precipitation with sodium phosphotungstate and magnesium chloride. Clin Chem 1981 27, 838–841.Google Scholar
40Setchell, KD, Lawson, AM, Borriello, SP, Harkness, R, Gordon, H, Morgan, DM, Kirk, DN, Adlercreatz, H, Anderson, LC & Axelson, MLignan formation in man – microbial involvement and possible roles in relation to cancer. Lancet 1981 ii, 4–7Google Scholar
41Sicilia, T, Niemeyer, HB, Honig, DM & Metzler, MIdentification and stereochemical characterization of lignans in flaxseed and pumpkin seeds. J Agric Food Chem 2003 51, 1181–1188.Google Scholar
42Sontag, TJ & Parker, RSCytochrome P450 omega-hydroxylase pathway of tocopherol catabolism. Novel mechanism of regulation of vitamin E status. J Biol Chem 2002 277, 25290–25296.CrossRefGoogle ScholarPubMed
43Thompson, LU, Seidl, MM, Rickard, SE, Orcheson, LJ & Fong, HHAntitumorigenic effect of a mammalian lignan precursor from flaxseed. Nutr Cancer 1996 26, 159–165.Google Scholar
44Westcott, ND & Muir, AD 1996 Process for extracting and purifiying lignans and cinnamic acid derivatives from flaxseed. PCT patent no. WO9630468A2.Google Scholar
45Westcott, ND & Muir, AD 1998 Process for extracting lignans from flaxseed. US patent no. 5.705.618.Google Scholar
46Westcott, ND & Muir, ADOverview of flax lignans. INFORM 2000 11, 118–121.Google Scholar
47Wright, JS, Johnson, ER & DiLabio, GAPredicting the activity of phenolic antioxidants: theoretical method, analysis of substituent effects, and application to major families of antioxidants. J Am Chem Soc 2001 123, 1173–1183.Google Scholar