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Chemical Compound Review

AG-K-31121     3,4-dihydroxy-3- (hydroxymethyl)-6,7...

Synonyms: NSC-50131, NSC50131, CTK6J9831, HMS3079K12, AC1L68M5, ...
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Disease relevance of Lignan


Psychiatry related information on Lignan

  • In conclusion, exposure to flaxseed or its purified lignan during lactation is a critical period in which mammary gland development may be promoted by enhancing the differentiation of the mammary gland structures [6].
  • CONCLUSIONS: Our results do not support the presence of a protective effect of higher intake of phytoestrogens in low doses on cardiovascular disease risk, although a small risk reduction with higher lignan intake cannot be excluded for smokers [7].

High impact information on Lignan


Chemical compound and disease context of Lignan


Biological context of Lignan

  • Chemically synthesized 3'-O-methyl-NDGA ((+/-)-2) showed identical anti-HIV activity (IC50 25 microM) to the lignan isolated from Creosote Bush [18].
  • The aims of our study were to determine (i) whether the tumor inhibitory effect of FS was due to its oil (FO), lignan secoisolariciresinol diglycoside (SDG), or both components, and (ii) whether the effect on tumor growth was related to increased lipid peroxidation [5].
  • A novel peroxidase that catalyses the dimerization of ferulic acid or caffeic acid via oxidative coupling and formation of beta beta'-linkage to the lignan-type compounds 8,8'-bis(caffeic acid) or 8,8'-bis(ferulic acid) respectively was purified from the leaves of Bupleurum salicifolium [19].
  • Novel substituted methylenedioxy lignan suppresses proliferation of cancer cells by inhibiting telomerase and activation of c-myc and caspases leading to apoptosis [20].
  • The kinetics of lignan accumulation in blood, following 10% FS supplementation, was determined using liquid chromatography tandem mass spectrometry [21].

Anatomical context of Lignan


Associations of Lignan with other chemical compounds

  • Flaxseed, a rich source of mammalian lignan precursor secoisolariciresinol-diglycoside (S.D.) and alpha-linolenic acid (ALA), has been shown to be protective at the early promotion stage of carcinogenesis [26].
  • Naphthalenic lignan lactone 3a (L-702,539), a potent and selective 5-lipoxygenase (5-LO) inhibitor, is extensively metabolized at two different sites: the tetrahydropyran and the lactone rings [27].
  • Although plasma enterolactone may be useful as a biological measure of exposure to lignan-containing foods, it may be of limited use as a specific biomarker of fruit and vegetable or plant food intake because coffee, tea, and alcoholic beverages also significantly increase its plasma concentration [28].
  • Sesamin, a major lignan in sesame seeds and oil, has been known to lower blood pressure in several types of experimental hypertensive animals [29].
  • The concentration of a major lignan, secoisolariciresinol diglycoside, was determined by HPLC in 4 selected wheat cultivars (i.e., Madison, Ernie, Betty, and Arapahoe) [30].

Gene context of Lignan


Analytical, diagnostic and therapeutic context of Lignan

  • Transcriptional profiling of the phenylpropanoid pathway in Pinus taeda cell suspension cultures was carried out using quantitative real time PCR analyses of all known genes involved in the biosynthesis of the two monolignols, p-coumaryl and coniferyl alcohols (lignin/lignan precursors) [36].
  • The expression in plants of dirigent proteins and proposed dirigent protein arrays in developing xylem and in other lignified tissues indicates roles for these proteins in both lignan formation and lignification [37].
  • The high negative correlation (r = -0.997, P < 0.001) between established tumor volume and urinary mammalian lignan excretion in the BD, S.D., 2.5% F and 5% F groups indicates that the reduction in tumor size is due in part to the lignans derived from the S.D. in flaxseed [26].
  • Micellar electrokinetic chromatography (MEKC) was used to separate twelve lignan compounds originating from Phyllanthus plants [38].
  • Additionally, elicitation of cell cultures with F. oxysporum extracts even triggered a strong incorporation of monolignols in the non condensed labile ether-linked lignin fraction concomitantly with a decrease in lignan and phenylcoumaran lignan accumulation [39].


  1. Does fiber-rich food containing animal lignan precursors protect against both colon and breast cancer? An extension of the "fiber hypothesis". Adlercreutz, H. Gastroenterology (1984) [Pubmed]
  2. Identification of lignans as major components in the phenolic fraction of olive oil. Owen, R.W., Mier, W., Giacosa, A., Hull, W.E., Spiegelhalder, B., Bartsch, H. Clin. Chem. (2000) [Pubmed]
  3. Dietary phytoestrogens and vascular function in postmenopausal women: a cross-sectional study. Kreijkamp-Kaspers, S., Kok, L., Bots, M.L., Grobbee, D.E., van der Schouw, Y.T. J. Hypertens. (2004) [Pubmed]
  4. The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity. Jenab, M., Thompson, L.U. Carcinogenesis (1996) [Pubmed]
  5. The inhibitory effect of flaxseed on the growth and metastasis of estrogen receptor negative human breast cancer xenograftsis attributed to both its lignan and oil components. Wang, L., Chen, J., Thompson, L.U. Int. J. Cancer (2005) [Pubmed]
  6. Exposure to flaxseed or purified lignan during lactation influences rat mammary gland structures. Ward, W.E., Jiang, F.O., Thompson, L.U. Nutrition and cancer. (2000) [Pubmed]
  7. Prospective study on usual dietary phytoestrogen intake and cardiovascular disease risk in Western women. van der Schouw, Y.T., Kreijkamp-Kaspers, S., Peeters, P.H., Keinan-Boker, L., Rimm, E.B., Grobbee, D.E. Circulation (2005) [Pubmed]
  8. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Davin, L.B., Wang, H.B., Crowell, A.L., Bedgar, D.L., Martin, D.M., Sarkanen, S., Lewis, N.G. Science (1997) [Pubmed]
  9. Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed. Prasad, K. Circulation (1999) [Pubmed]
  10. Oxidative aryl-benzyl coupling. A biomimetic entry to podophyllin lignan lactones. Kende, A.S., Liebeskind, L.S., Mills, J.E., Rutledge, P.S., Curran, D.P. J. Am. Chem. Soc. (1977) [Pubmed]
  11. Justicidin A inhibits the transport of tumor necrosis factor-alpha to cell surface in lipopolysaccharide-stimulated RAW 264.7 macrophages. Tsao, L.T., Lin, C.N., Wang, J.P. Mol. Pharmacol. (2004) [Pubmed]
  12. Circulating enterolactone and risk of endometrial cancer. Zeleniuch-Jacquotte, A., Lundin, E., Micheli, A., Koenig, K.L., Lenner, P., Muti, P., Shore, R.E., Johansson, I., Krogh, V., Lukanova, A., Stattin, P., Afanasyeva, Y., Rinaldi, S., Arslan, A.A., Kaaks, R., Berrino, F., Hallmans, G., Toniolo, P., Adlercreutz, H. Int. J. Cancer (2006) [Pubmed]
  13. Dietary phytoestrogen intake and premenopausal breast cancer risk in a German case-control study. Linseisen, J., Piller, R., Hermann, S., Chang-Claude, J. Int. J. Cancer (2004) [Pubmed]
  14. Hypocholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed. Prasad, K. Atherosclerosis (2005) [Pubmed]
  15. Effects of vitamin e and sesamin on hypertension and cerebral thrombogenesis in stroke-prone spontaneously hypertensive rats. Noguchi, T., Ikeda, K., Sasaki, Y., Yamamoto, J., Yamori, Y. Clin. Exp. Pharmacol. Physiol. (2004) [Pubmed]
  16. Diet and breast cancer. Adlercreutz, H., Mousavi, Y., Höckerstedt, K. Acta oncologica (Stockholm, Sweden) (1992) [Pubmed]
  17. A new and known cytotoxic aryltetralin-type lignans from stems of Bursera graveolens. Nakanishi, T., Inatomi, Y., Murata, H., Shigeta, K., Iida, N., Inada, A., Murata, J., Farrera, M.A., Iinuma, M., Tanaka, T., Tajima, S., Oku, N. Chem. Pharm. Bull. (2005) [Pubmed]
  18. Antiviral activities of methylated nordihydroguaiaretic acids. 1. Synthesis, structure identification, and inhibition of tat-regulated HIV transactivation. Hwu, J.R., Tseng, W.N., Gnabre, J., Giza, P., Huang, R.C. J. Med. Chem. (1998) [Pubmed]
  19. Purification of a new peroxidase catalysing the formation of lignan-type compounds. Frías, I., Siverio, J.M., González, C., Trujillo, J.M., Pérez, J.A. Biochem. J. (1991) [Pubmed]
  20. Novel substituted methylenedioxy lignan suppresses proliferation of cancer cells by inhibiting telomerase and activation of c-myc and caspases leading to apoptosis. Giridharan, P., Somasundaram, S.T., Perumal, K., Vishwakarma, R.A., Karthikeyan, N.P., Velmurugan, R., Balakrishnan, A. Br. J. Cancer (2002) [Pubmed]
  21. Dietary flaxseed supplementation ameliorates inflammation and oxidative tissue damage in experimental models of acute lung injury in mice. Kinniry, P., Amrani, Y., Vachani, A., Solomides, C.C., Arguiri, E., Workman, A., Carter, J., Christofidou-Solomidou, M. J. Nutr. (2006) [Pubmed]
  22. Exposure to flaxseed or its lignan component during different developmental stages influences rat mammary gland structures. Tou, J.C., Thompson, L.U. Carcinogenesis (1999) [Pubmed]
  23. Structure--antitubulin activity relationship in steganacin congeners and analogues. Inhibition of tubulin polymerization in vitro by (+/-)-isodeoxypodophyllotoxin. Zavala, F., Guenard, D., Robin, J.P., Brown, E. J. Med. Chem. (1980) [Pubmed]
  24. Justicidin A decreases the level of cytosolic Ku70 leading to apoptosis in human colorectal cancer cells. Lee, J.C., Lee, C.H., Su, C.L., Huang, C.W., Liu, H.S., Lin, C.N., Won, S.J. Carcinogenesis (2005) [Pubmed]
  25. Inhibition of lipopolysaccharide-inducible nitric oxide synthase, TNF-alpha and COX-2 expression by sauchinone effects on I-kappaBalpha phosphorylation, C/EBP and AP-1 activation. Lee, A.K., Sung, S.H., Kim, Y.C., Kim, S.G. Br. J. Pharmacol. (2003) [Pubmed]
  26. Flaxseed and its lignan and oil components reduce mammary tumor growth at a late stage of carcinogenesis. Thompson, L.U., Rickard, S.E., Orcheson, L.J., Seidl, M.M. Carcinogenesis (1996) [Pubmed]
  27. Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: structure-activity relationship study directed toward the improvement of metabolic stability. Delorme, D., Ducharme, Y., Brideau, C., Chan, C.C., Chauret, N., Desmarais, S., Dubé, D., Falgueyret, J.P., Fortin, R., Guay, J., Hamel, P., Jones, T.R., Lépine, C., Li, C., McAuliffe, M., McFarlane, C.S., Nicoll-Griffith, D.A., Riendeau, D., Yergey, J.A., Girard, Y. J. Med. Chem. (1996) [Pubmed]
  28. Dietary determinants of plasma enterolactone. Horner, N.K., Kristal, A.R., Prunty, J., Skor, H.E., Potter, J.D., Lampe, J.W. Cancer Epidemiol. Biomarkers Prev. (2002) [Pubmed]
  29. Sesamin metabolites induce an endothelial nitric oxide-dependent vasorelaxation through their antioxidative property-independent mechanisms: possible involvement of the metabolites in the antihypertensive effect of sesamin. Nakano, D., Kwak, C.J., Fujii, K., Ikemura, K., Satake, A., Ohkita, M., Takaoka, M., Ono, Y., Nakai, M., Tomimori, N., Kiso, Y., Matsumura, Y. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  30. Lignans are involved in the antitumor activity of wheat bran in colon cancer SW480 cells. Qu, H., Madl, R.L., Takemoto, D.J., Baybutt, R.C., Wang, W. J. Nutr. (2005) [Pubmed]
  31. Lignans and tamoxifen, alone or in combination, reduce human breast cancer cell adhesion, invasion and migration in vitro. Chen, J., Thompson, L.U. Breast Cancer Res. Treat. (2003) [Pubmed]
  32. Sauchinone, a lignan from Saururus chinensis, suppresses iNOS expression through the inhibition of transactivation activity of RelA of NF-kappaB. Hwang, B.Y., Lee, J.H., Jung, H.S., Kim, K.S., Nam, J.B., Hong, Y.S., Paik, S.G., Lee, J.J. Planta Med. (2003) [Pubmed]
  33. Inhibitory activity of lignan components from the flower buds of Magnoliae fargesii on the expression of cell adhesion molecules. Ahn, K.S., Jung, K.Y., Kim, J.H., Oh, S.R., Lee, H.K. Biol. Pharm. Bull. (2001) [Pubmed]
  34. 1-Arylnaphthalene lignan: a novel scaffold for type 5 phosphodiesterase inhibitor. Ukita, T., Nakamura, Y., Kubo, A., Yamamoto, Y., Takahashi, M., Kotera, J., Ikeo, T. J. Med. Chem. (1999) [Pubmed]
  35. Antiinflammatory and antiallodynic actions of the lignan niranthin isolated from Phyllanthus amarus Evidence for interaction with platelet activating factor receptor. Kassuya, C.A., Silvestre, A., Menezes-de-Lima, O., Marotta, D.M., Rehder, V.L., Calixto, J.B. Eur. J. Pharmacol. (2006) [Pubmed]
  36. Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism. Anterola, A.M., Jeon, J.H., Davin, L.B., Lewis, N.G. J. Biol. Chem. (2002) [Pubmed]
  37. Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. Gang, D.R., Costa, M.A., Fujita, M., Dinkova-Kostova, A.T., Wang, H.B., Burlat, V., Martin, W., Sarkanen, S., Davin, L.B., Lewis, N.G. Chem. Biol. (1999) [Pubmed]
  38. Analysis of lignans using micellar electrokinetic chromatography. Kuo, C.H., Lee, S.S., Chang, H.Y., Sun, S.W. Electrophoresis (2003) [Pubmed]
  39. Differential accumulation of monolignol-derived compounds in elicited flax (Linum usitatissimum) cell suspension cultures. Hano, C., Addi, M., Bensaddek, L., Crônier, D., Baltora-Rosset, S., Doussot, J., Maury, S., Mesnard, F., Chabbert, B., Hawkins, S., Lainé, E., Lamblin, F. Planta (2006) [Pubmed]
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