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Structure type: oligomer ; 662
C₃₀H₄₆O₁₆
Compound class: lignan glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11651
  Qui SX, Lu ZZ, Luyengi L, Lee SK, Pezzuto JM, Farnsworth NR, Thompson LU, Fong HHS "Isolation and characterization of flaxseed (Linum usitatissimum) constituents" - Pharmaceutical Biology 37(1) (1999) 1-7
  

  During a large-scale isolation of the cancer chemopreventive mammalian lignan precursor secoisolariciresinol diglucoside (SDG, 6) from the defatted meal of flaxseed (Linum usitatissimum L.), a new flavonoid, herbacetin 3,8-O-diglucopynanoside (1) was obtained along with two known flavonoids, herbacetin 3,7-O-dimethyl ether (3) and kaempferol 3,7-O-diglucopyranoside (4), and the known lignan (-)-pinoresinol diglucoside (5). The structure of herbacetin 3,8-O-β-D-diglucopynanoside (1) was determined by a combination of NMR techniques. Further the absolute configuration of the stereogenic center of secoisolari-ciresinol diglucoside (SDG, 6) was assigned by spectroscopic methods. Herbacetin 3,7-O-dimethyl ether (3) and herbacetin (2), the aglycone of 1, were shown to mediate antioxidant activity which may contribute to the chemopreventive activity of flaxseed.

  structure elucidation, Antioxidant activity, NMR assignments, lignan glucosides, flaxseed, Linum usitatissimum L., flavonoid glucosides, cancer chemoprevention

  Publication DOI: 10.1076/phbi.37.1.1.6320
  Journal NLM ID: 9812552
  Publisher: Lisse, the Netherlands: Swets & Zeitlinger
  Institutions: Program for Collaborative Research in the Pharmaceutical Sciences, Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, Chicago, IL, USA, Department of Nutritional Sciences, Faculty of Medicine, University of Toronto, Toronto, Canada
  Methods: 13C NMR, 1H NMR, EI-MS, IR, FAB-MS, TLC, MS, UV, optical rotation measurement, DEPT, antioxidant activity assay, HCl hydrolysis, sulfuric acid hydrolysis
  
   
  
  Linum usitatissimum
  CSDB ID 62397 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoside, lignan, lignan glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 12095
  Clark WF, Muir AD, Westcott ND, Parbtani A "A novel treatment for lupus nephritis: lignan precursor derived from flax" - Lupus 9(6) (2000) 429-436
  

  Flaxseed has renoprotective effects in animal and human lupus nephritis. We have recently extracted the lignan precursor (secoisolariresinol diglucoside) (SDG) to determine if this more palatable derivative of flaxseed would exert renoprotection similar to the whole flaxseed in the aggressive MRL/lpr lupus mouse model. 131 MRL/lpr mice were randomly assigned to saline gavage, 600, 1,200 and 4,800 μg lignan gavage groups. At 7 weeks, 6 animals underwent platelet aggregating factor (PAF) lethal challenge and 40 were studied with urine collection to determine the levels of secoisolariresinol, enterodiol and enterolactone in the gavaged animals. A baseline study of 10 saline gavaged animals took place at 6 weeks. 25 animals in the saline gavage, 600 and 1200 microg lignan groups were studied at 14 and 22 weeks for GFR, spleen lymphocyte S-phase and organ weight studies. Metabolic studies indicated that secoisolariresinol is the major metabolite absorbed and the lowest lignan dose provides a lengthening in survival for the PAF lethal challenge. Body weight, fluid and water intake studies demonstrated that the lignan was well tolerated. Changes in proteinuria, GFR and renal size showed a time- and dose-dependent protection for the lignan precursor. Cervical lymph node size and spleen lymphocyte cells in the S-phase demonstrated modest dose-dependent reductions in the lignan gavaged groups. SDG was converted in the gut to secoisolariresinol, which was absorbed and well tolerated by the MRL/lpr mice. Renoprotection was evidenced, in a dose-dependent fashion, by a significant delay in the onset of proteinuria with preservation in GFR and renal size. This study suggests that SDG may have a therapeutic role in lupus nephritis.

  flaxseed, lupus, nephritis, PAF, omega-3 fatty acids

  NCBI PubMed ID: 10981647
  Publication DOI: 10.1191/096120300678828622
  Journal NLM ID: 9204265
  Publisher: London: SAGE Publications
  Correspondence: william.clark@lhsc.on.ca
  Institutions: Department of Medicine, London Health Sciences Centre and The University of Western Ontario, London, Canada, Agriculture and Agri-Food Canada, Saskatoon Research Centre, Saskatoon, SK, Canada
  Methods: biological assays, radiolabeling, radioactivity measurement, alkaline hydrolysis, UV, enzymatic digestion, extraction, CC, HPLC-MS, flow cytometry analysis, evaporation, HPLC-ELSD
  
   
  
  Linum usitatissimum
  CSDB ID 65165 (all data & tools)
• Article ID: 12389
  Johnsson P, Kamal-Eldin A, Lundgren LN, Aman P "HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds" - Journal of Agricultural and Food Chemistry 48(11) (2000) 5216-5219
  

  A method was developed for the analysis of secoisolariciresinol diglucoside (SDG) in flaxseeds. The analytical method involves extraction of defatted flaxseed flour with dioxane/ethanol, aqueous base-hydrolysis, solid-phase purification of an SDG-containing fraction, and quantitative analysis by high-performance liquid chromatography (HPLC). Pure SDG was isolated from flaxseed using different column chromatographic methods and used, as external standard, for the calibration of the method and for quantification. The method was then applied to study the variation in SDG content in flaxseeds from 14 cultivars grown in Sweden and 15 cultivars grown in Denmark. The SDG content varied between 11.7 and 24.1 mg/g in defatted flaxseed flour and between 6.1 and 13.3 mg/g in whole flaxseeds.

  HPLC, lignan, flaxseed, secoisolarciresinol diglucoside

  NCBI PubMed ID: 11087462
  Publication DOI: 10.1021/jf0005871
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: Afaf.Kamal-Eldin@lmv.slu.se
  Institutions: Department of Food Science and Department of Chemistry, Swedish University of Agricultural Sciences (SLU), Uppsala, Sweden
  Methods: 1H NMR, HPLC, alkaline hydrolysis, extraction, CC, evaporation
  
   
  
  Linum usitatissimum cv. Antares, Linum usitatissimum cv. Barbara, Linum usitatissimum cv. Bor 18, Linum usitatissimum cv. Dufferin, Linum usitatissimum cv. Flanders, Linum usitatissimum cv. Gold Merchant, Linum usitatissimum cv. Helle, Linum usitatissimum cv. Helmi, Linum usitatissimum cv. Mikael, Linum usitatissimum cv. NorLin, Linum usitatissimum cv. NorMan, Linum usitatissimum cv. Pronto, Linum usitatissimum cv. Vimy, Linum usitatissimum cv. Zoltan, Linum usitatissimum cv. Dansk soya, Linum usitatissimum cv. Dänish 21, Linum usitatissimum cv. FDB 126, Linum usitatissimum cv. Göteborg I, Linum usitatissimum cv. Harreskovgård, Linum usitatissimum cv. H. C. Møller La Plata, Linum usitatissimum cv. Herkules, Linum usitatissimum cv. Hør 015, Linum usitatissimum cv. Hør 48, Linum usitatissimum cv. La Plata 1939, Linum usitatissimum cv. Lyngby S. H., Linum usitatissimum cv. Lyngby 21, Linum usitatissimum cv. Øtofte 199/77, Linum usitatissimum cv. Øtofte 235/47, Linum usitatissimum cv. Øtofte 356
  CSDB ID 66455 (all data & tools)
• Article ID: 12432
  Madhusudhan B, Wiesenborn D, Schwarz J, Tostenson K, Gillespie J "A dry mechanical method for concentrating the lignan secoisolariciresinol diglucoside in flaxseed" - Lebensmittel-Wissenschaft und Technologie = Food Science and Technology 33(4) (2000) 268-275
  

  A dry mechanical process was evaluated for obtaining a hull-rich fraction from flaxseed. Flaxseed hulls (seed coats) are an excellent source of secoisolariciresinol diglucoside (SDG), a lignan with potential functional food applications, but flaxseed hulls adhere tightly to the embryo, making separation difficult. A Comitrol processor was used to mill the seed, followed by sieving and aspiration to obtain a hull-rich fraction from Neche and Omega flaxseed cultivars. As a result, the content of secoisolariciresinol diglucoside (nonfat, dry basis) increased from 12.9 and 14.3 g/kg in whole Neche and Omega seed, respectively, to 27.6 and 23.8 g/kg (weighted averages) in the hull-rich fractions. The significant (P<0.0005) inverse correlation between oil and SDG contents for cv. Neche suggests that oil content in dry-milled fractions is a useful indicator of secoisolariciresinol diglucoside content. Compared to similar reported processes, this was less effective at producing a hull-free embryo, but the Neche hull fraction contained much less fat (173 g/kg weighted average) than the other processes. The hull fraction appears to be a good source of SDG for functional food studies.

  flaxseed; lignan; secoisolariciresinol diglucoside; dehulling process

  Publication DOI: 10.1006/fstl.2000.0652
  Journal NLM ID: 9876251
  Publisher: London, etc.: Academic Press, etc.
  Institutions: Kuvempu University, Jnana Sahyadri, Shankaraghatta, India, Agricultural and Biosystems Engineering Department, North Dakota State University, Fargo, ND, USA, Cereal Science Department, North Dakota State University, Fargo, ND, USA
  Methods: extraction, LC
  
   
  
  Linum usitatissimum
  CSDB ID 66657 (all data & tools)
• Article ID: 12507
  Muir AD, Westcott ND "Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal" - Journal of Agricultural and Food Chemistry 48(9) (2000) 4048-4052
  

  Samples of commercially prepared white, whole wheat, flax, and multigrain breads were analyzed by a rapid RP-HPLC method for the presence of the lignan secoisolariciresinol diglucoside (SDG). SDG was detected only in products containing flax, with concentrations ranging from 0.06 to 1.98 μM/g of DW (19−602 μM/loaf). Full-fat flax meal, powdered aqueous alcohol extracts of flax seed, and SDG were added to a white bread mix and baked into loaves in a domestic bread maker. Quantitative recovery of SDG from the test breads was observed when SDG was added; however, when flax meal or aqueous alcohol extracts were added, only 73−75% of the theoretical yield of SDG was recovered. SDG was also detected in commercially prepared flax cookies, bagels, and muffins with concentrations ranging from 0.26 to 2.93 μM/g of DW. The extent of grinding of the flax seed was also shown to have a significant effect on the recovery of SDG from both flax meal breads and baked goods, with extraction of SDG from finely ground samples greater than that from course material.

  flax seed; lignan; secoisolariciresinol diglucoside; HPLC; bread; SDG

  NCBI PubMed ID: 10995312
  Publication DOI: 10.1021/jf990922p
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: muira@em.agr.ca
  Institutions: Crop Utilization, Saskatoon Research Centre, Agriculture and Agri-Food Canada, Saskatoon, SK, Canada
  Methods: extraction, RP-HPLC
  
   
  
  Linum usitatissimum
  CSDB ID 66960 (all data & tools)