Arroo RRJ, Androutsopoulos V, Beresford K, Ruparelia K, Surichan S, Wilsher N, et al. Phytoestrogens as natural prodrugs in cancer prevention: dietary flavonoids. Phytochem Rev. 2009;8:375–86.
Buck K, Zaineddin AK, Vrieling A, Heinz J, Linseisen J, Flesch-Janys D, et al. Estimated enterolignans lignan-rich foods and fibre in relation to survival after postmenopausal breast cancer. Brit J Cancer. 2011;105:1151–7.
Wang Y, Fofana B, Roy M, Ghose K, Yao X-H, Nixon M-S, et al. Flaxseed lignan secoisolariciresinol diglucoside improves insulin sensitivity through upregulation of GLUT4 expression in diet-induced obese mice. J Funct Foods. 2015;18:1–9.
Pan JY, Chen SL, Yang MH, Wu J, Sinkkonen J, Zou K. An update on lignans: natural products and synthesis. Nat Prod Rep. 2009;26:1251–92.
Noguchi A, Fukui Y, Iuchi-Okada A, Kakutani S, Satake H, Iwashita T, et al. Sequential glucosylation of furofuran lignan (+)-sesaminol by Sesamum indicum UGT71A9 and UGT94D1 glucosyltransferase. Plant J. 2008;54:415–27.
Touré A, Xueming X. Flaxseed lignans: source, biosynthesis, metabolism, antioxidant activity, bio-active components, and health benefits. Comprehensive Rev Food Sci and Food Safety. 2010;9:261–9.
Struijs K, Vincken JP, Doeswijk DG, Voragen AG, Gruppen H. The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides. Phytochemistry. 2009;70:262–9.
Kosińska A, Penkacik K, Wiczkowski W, Amarowicz R. Presence of caffeic acid in flaxseed lignan macromolecule. Plant Foods Hum Nutr. 2011;66:270–4.
Gachon CM, Langlois-Meurinne M, Saindrenan P. Plant secondary metabolism glycosyltransferases: the emerging functional analysis. Trends Plant Sci. 2005;10:542–9.
Osmani SA, Bak S, Møller BL. Substrate specificity of plant UDP-dependent glycosyltransferases predicted from crystal structures and homology modeling. Phytochemistry. 2009;70:325–47.
Bowles D, Isayenkova J, Lim E, Poppenberger B. Glycosyltransferases: managers of small molecules. Curr Opin Plant Biol. 2005;8:254–63.
Wang J, Hou B. Glycosyltransferases: key players involved in the modification of plant secondary metabolites. Front Biol. 2009;4:39–46.
Yonekura-Sakakibara K, Hanada K. An evolutionary view of functional diversity in family 1 glycosyltransferases. Plant J. 2011;66:182–93.
Caputi L, Malnoy M, Goremykin V, Nikiforova S, Martens S. A genome-wide phylogenetic reconstruction of family 1 UDP-glycosyltransferases revealed the expansion of the family during the adaptation of plants to life on land. Plant J. 2012;69:1030–42.
Ross J, Li Y, Lim EK, Bowles DJ. Higher plant glycosyltransferases. Genome Biol. 2001;2:30041–6.
Witte S, Moco S, Vervoort J, Matern U, Martens S. Recombinant expression and functional characterisation of regiospecific flavonoid glycosyltransferases from Hieracium pilosella L. Planta. 2009;229:1135–46.
Barvkar VT, Pardeshi VC, Kale SM, Kadoo NY, Gupta VS. Phylogenomic analysis of UDP glycosyltransferase 1 multigene family in Linum usitatissimum identified genes with varied expression patterns. BMC Genomics. 2012;13:175.
Wang Z, Hobson N, Galindo L, Zhu S, Shi D, McDill J, et al. The genome of flax (Linum usitatissimum) assembled de novo from short shotgun sequence reads. Plant J. 2012;72:461–73.
Ghose K, Selvaraj K, McCallum J, Kirby CW, Sweeney-Nixon M, Cloutier SJ, et al. Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG). BMC Plant Biol. 2014;14:82.
Ghose K, McCallum JL, Sweeney-Nixon M, Fofana B. Histidine 352 (His352) and tryptophan 355 (Trp355) are essential for flax UGT74S1 glucosylation activity toward secoisolariciresinol. PLoS One. 2015;10(2):e116248.
Pan X, Siloto RMP, Wickramarathna AD, Mietkiewska E, Weselake RJ. Identification of a pair of phospholipid: Diacylglycerol acyltransferases from developing flax (Linum usitatissimum L.) seed catalyzing the selective production of trilinolenin. J Biol Chem. 2013;288:24173–88.
Thambugala D, Duguid S, Loewen E, Rowland G, Booker E, You FM, et al. Genetic variation of six desaturase genes in flax and their impact on fatty acid composition. Theor Appl Genet. 2013;126:2627–41.
You FM, Li P, Kumar S, Ragupathy R, Li ZN, Fu YB, et al. Genome-wide identification and characterization of the gene families controlling fatty acid biosynthesis in flax (Linum usitatissimum L). J Prot Bioinformatics. 2014;7:310–26.
Kenaschuk EO, Rashid KY. AC McDuff flax. Can J Plant Sci. 1994;74:815–6.
Fofana B, Cloutier S, Duguid S, Ching J, Rampitsch C. Gene expression of stearoyl-ACP desaturase (SAD) and 12 fatty acid desaturase 2 (FAD2) is modulated during seed development and affect fatty acid composition of flax (Linum usitatissimum). Lipids. 2006;41:705–12.
Tamura K, Stecher G, Peterson D, Filipski A, Kumar S. MEGA6: molecular evolutionary genetics analysis version 6.0. Mol Biol Evol. 2013;30:2725–9.
Thompson JD, Higgins DG, Gibson TJ. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994;22:4673–80.
Edgar RC. MUSCLE: multiple sequence alignment with high accuracy and high throughput. Nucleic Acids Res. 2004;32:1792–7.
You FM, Li P, Kumar S, Ragupathy R, Banik M, Duguid SD, et al. The refined flax genome, its evolution and application. 2015; XXIII Plant and Animal Genome Conf, San Diego, CA, USA, January 10-14, 2015, P1039.
Nei M, Gojobori T. Simple methods for estimating the numbers of synonymous and nonsynonymous nucleotide substitutions. Mol Biol Evol. 1986;3:418–26.
Sveinsson S, McDill J, Wong GKS, Li J, Li X, Deyholos MK, et al. Phylogenetic pinpointing of a paleopolyploidy event within the flax genus (Linum) using transcriptomics. Ann Bot. 2014;113:753–61.
Vanneste K, Van de Peer Y, Maere S. Inference of genome duplications from age distributions revisited. Mol Biol and Evol. 2013;30:177–90.
Gaut BS, Morton BR, McCaig BC, Clegg MT. Substitution rate comparisons between grasses and palms: synonymous rate differences at the nuclear gene Adh parallel rate difference at the plastid gene rbcL. Proc Natl Acad Sci U S A. 1996;93:10274–9.
Heckman KL, Pease LR. Gene splicing and mutagenesis by PCR-driven overlap extension. Nat Protocols. 2007;2:924–32.
Livak KJ, Schmittgen TD. Analysis of relative gene expression data using Real-Time quantitative PCR and the 2-ΔΔCT. Methods. 2001;25:402–8.
Li X, Yuan J-P, Xu S-P, Wang J-H, Liu X. Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography. J Chromatogr A. 2008;1185:223–32.
Zhang PG, Huang SZ, Pin A-L, Adams KL. Extensive divergence in alternative splicing patterns after gene and genome duplication during the evolutionary history of Arabidopsis. Mol Biol Evol. 2010;27:1686–97.
Wood TE, Takebayashi N, Barker MS, Mayrose I, Greenspoon PB, Rieseberg LH. The frequency of polyploid speciation in vascular plants. Proc Natl Acad Sci U S A. 2009;106:13875–9.
Lynch M, Conery JS. The evolutionary fate and consequences of duplicate genes. Science. 2000;290:1151–5.
Jordan IK, Wolf YI, Koonin EV. Duplicated genes evolve slower than singletons despite the initial rate increase. BMC Evol Biol. 2004;4:22.
Wang Y, Feng L, Zhu Y, Li Y, Yan H, Xiang Y. Comparative genomic analysis of the WRKY III gene family in populus, grape. Arabidopsis and Rice Biol Direct. 2015;10:48.
Wu X, Yang H, Qu C, Xu Z, Li W, Hao B, et al. Sequence and expression analysis of the AMT gene family in poplar. Frontiers Plant Sci. 2015;6:337.54.
Paterson AH, Freeling M, Tang H, Wang X. Insights from the comparison of plant genome sequences. Annu Rev Plant Biol. 2010;61:349–72.
Wang Y, Tan X, Patterson AH. Different patterns of gene structure divergence following gene duplication in Arabidopsis. BMC Genomics. 2013;14:652.
Yang SH, Zhang XH, Yue JX, Tian DC, Chen JQ. Recent duplications dominate NBS-encoding gene expansion in two woody species. Mol Genet Genomics. 2008;280:187–98.
Zhong Y, Li Y, Huang K, Cheng Z-M. Species-specific duplications of NBS-encoding genes in Chinese chestnut (Castanea mollissima). Sci Rep. 2015;5:16638.
Harikrishnan S, Pucholt P, Berlin S. Sequence and gene expression evolution of paralogous genes in willows. Sci Rep. 2015;5:18662.
Kawaura K, Mochida K, Enju A, Totoki Y, Toyoda A, Sakaki Y, et al. Assessment of adaptive evolution between wheat and rice as deduced from full-length common wheat cDNA sequence data and expression patterns. BMC Genomics. 2009;10:271.
Tucker AE. Genetic variation within the Daphnia Pulex genome. PhD Thesis, University of New Hampshire. 2009. Available: https://books.google.ca/books?isbn=1109233620
Lu Y, Rausher MD. Evolutionary rate variation in anthocyanin pathway genes. Mol Biol Evol. 2003;20:184–1853.
Han F, Peng Y, Xu L, Xiao P. Identification, characterization, and utilization of single copy genes in 29 angiosperm genomes. BMC Genomics. 2014;15:504.
Jiang S-Y, Chi YH, Wang J-Z, Zhou J-X, Cheng Y-S, Zhang B-L, et al. Sucrose metabolism gene families and their biological functions. Sci Rep. 2015;5:17583.
MacRae WD, Toewers GHN. Biological activities of lignans. Phytochemistry. 1984;23:1207–20.
Harmatha J, Dinan L. Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions. Phytochemistry Rev. 2003;2:321–30.
Ramsay A, Fliniaux O, Quéro A, Molinié R, Demailly H, Hano C, et al. Kinetics of the incorporation of the main phenolic compounds into the lignan macromolecule during flaxseed development. Food Chem. 2017;217:1–8.
Fang J, Ramsay A, Renouard S, Hano C, Lamblin F, Chabbert B, et al. Laser microdissection and spatiotemporal Pinoresinol-Lariciresinol Reductase gene expression assign the cell layer-specific accumulation of secoisolariciresinol diglucoside in flaxseed coats. Front Plant Sci. 2016;7:1743.
Sakuma S, Pourkheirandish M, Hensel G, Kumlehn J, Stein N, Tagiri A, et al. Divergence of expression pattern contributed to neofunctionalization of duplicated HD-Zip I transcription factor in barley. New Phytol. 2013;197:939–48.
Masada S, Terasaka K, Mizukami H. A single amino acid in the PSPG-box plays an important role in the catalytic function of caUGT2 (Cucurmin glucosytransferase) a group d family glycosyltransferase 1 from Catharantus roseus. FEBS Lett. 2007;581:2605–10.