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Toward Engineering the Metabolic Pathways of Cancer-Preventing Lignans in Cereal Grains and Other Crops

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Phytochemicals in Human Health Protection, Nutrition, and Plant Defense

Part of the book series: Recent Advances in Phytochemistry ((RAPT,volume 33))

Abstract

Lignans, ubiquitous constituents of vascular plants, have a number of properties that are of use to humans: some can protect against the onset of various cancers,1 whereas others have antimitotic, antiviral, antibacterial, and antifungal properties.2 Certain lignans can also function, for example, as antioxidants, platelet activating factor receptor antagonists, and anti-tubercular agents, and others are disinfectants, moth repellants, and insecticides.3–5 Because of their important applications from a health and economic perspective, intensified efforts are being expended to both understand and manipulate their biosynthetic pathways. Accordingly, this chapter highlights progress being made towards deciphering the 8–8’ linked lignan metabolic pathway and its utility to the bioengineering of human foodstuffs.

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References

  1. SETCHELL, K.D.R., ADLERCREUTZ, H. 1988. Mammalian lignans and phyto-oestrogens. Recent studies on their formation, metabolism and biological role in health and disease. In: Role of the Gut Flora in Toxicity and Cancer. (Rowland, I.R., ed.) Academic Press, London, pp 315–345.

    Google Scholar 

  2. LEWIS, N.G., DAVIN, L.B. 1999. Lignans: Biosynthesis and function. In: Comprehensive Natural Products Chemistry. Vol. 1. (Barton, Sir D.H.R., Nakanishi, K., Meth-Cohn, O., eds), Elsevier, London, pp 639–712.

    Chapter  Google Scholar 

  3. FAURE, M., LISSI, E., TORRES, R., VIDALA, L.A. 1990. Antioxidant activities of lignans and flavonoids. Phytochemistry 29: 3773–3775.

    Article  CAS  Google Scholar 

  4. HARMATHA, J., NAWROT, J. 1984. Comparison of the feeding deterrent activity of some sesquiterpene lactones and a lignan lactone towards selected insect storage pests. Biochem. Syst. Ecol. 12: 95–98.

    Article  CAS  Google Scholar 

  5. MACRAE, D.W., TOWERS, G.H.N. 1984. Biological activities of lignans. Phytochemistry 23: 1207–1220.

    Article  CAS  Google Scholar 

  6. AYRES, D.C., LOIKE, J.D. 1990. Chemistry and Pharmacology of Natural Products. Lignans. Chemical, Biological and Clinical Properties. Cambridge University Press, Cambridge, England, pp. 402.

    Book  Google Scholar 

  7. ADLERCREUTZ, H., HOECKERSTEDT, K., BANNWART, C., BLOIGU, S., HÄMÄLÄINEN, E., FOTSIS, T., OLLUS, A. 1987. Effect of dietary components, including lignans and phytoestrogens, on enterohepatic circulation and liver metabolism of estrogens and on sex hormone binding globulin (shbg). J. Steroid Biochem. 27: 1135–1144.

    Article  PubMed  CAS  Google Scholar 

  8. HERMAN, C., ADLERCREUTZ, H., GOLDIN, B.R., GORBACH, S.L., HÖCKERSTEDT, K.A.V., WATANABE, S., HÄMÄLÄINEN, E.K., MARKKANEN, M.H., MAKELA, T.H., WÄHÄLÄ, K.T., HASE, T.A., FOTSIS, T. 1995. Phytoestrogen intake and cancer risk. J. Nutr. 125: 757–770.

    Google Scholar 

  9. KORPELA, J.T., KORPELA, R., ADLERCREUTZ, H. 1992. Fecal bile acid metabolic pattern after administration of different types of bread. Gastroenterology 103: 1246–1253.

    PubMed  CAS  Google Scholar 

  10. SLAVIN, J., JACOBS, C., MARQUART, L. 1997. Whole-grain consumption and chronic disease: protective mechanisms. Nutr. Cancer 27: 14–21.

    CAS  Google Scholar 

  11. ADLERCREUTZ, H. 1984. Does fiber-rich food containing animal lignan precursors protect against both colon and breast cancer? An extension of the “fiber hypothesis”. Gastroenterology 86: 761–764.

    PubMed  CAS  Google Scholar 

  12. HORWITZ, C., WALKER, A.R.P. 1984. Lignans. Additional benefits from fiber. Nutr. Cancer 6: 73–76.

    Article  PubMed  CAS  Google Scholar 

  13. KURZER, M.S., Xu, X. 1997. Dietary phytoestrogens. Annu. Rev. Nutr. 17: 353–381.

    Article  PubMed  CAS  Google Scholar 

  14. ADLERCREUTZ, H. 1996. Lignans and isoflavonoids: Epidemiology and possible role in prevention of cancer. In: Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. (Kumpulainen, J.T., Salonen, J.K., eds), The Royal Society of Chemistry, Cambridge, England, pp 349–355.

    Google Scholar 

  15. THOMPSON, L., ORCHESON, L., RICKARD, S., JENAB, M., SERRAINO, M., SEIDL, M., CHEUNG, F. 1996. Anticancer effects of flaxseed lignans. In: Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. (Kumpulainen, J.T., Salonen, J.K., eds), The Royal Society of Chemistry, Cambridge, England, pp 356–364.

    Chapter  Google Scholar 

  16. BORRIELLO, S.P., SETCHELL, K.D.R., AXELSON, M., LAWSON, A.M. 1985. Production and metabolism of lignans by the human faecal flora. J. Appl. Bacteriol. 58: 37–43.

    Article  PubMed  CAS  Google Scholar 

  17. FORD, J.D., DAVIN, L.B., LEWIS, N.G. 1999. Lignans and health: Cancer chemoprevention and biotechnological opportunities with plant lignans. In: Plant Polyphenols 2: Chemistry and Biology. (Gross, G.G., Hemingway, R.W., Yoshida, T., eds), Plenum Press, New York, pp (••).

    Google Scholar 

  18. SETCHELL, K.D.R., LAWSON, A.M., MITCHELL, F.L., ADLERCREUTZ, H., KIRK, D.N., AXELSON, M. 1980. Lignans in man and in animal species. Nature 287: 740–742.

    Article  PubMed  CAS  Google Scholar 

  19. STITCH, S.R., TOUMBA, J.K., GROEN, M.B., FUNKE, C.W., LEEMHUIS, J., VINK, J., WOODS, G.F. 1980. Excretion, isolation and structure of a new phenolic constituent of female urine. Nature 287: 738–740.

    Article  PubMed  CAS  Google Scholar 

  20. NESBITT, P.D., THOMPSON, L.U 1997. Lignans in homemade and commercial products containing flaxseed. Nutr. Cancer 29: 222–227.

    CAS  Google Scholar 

  21. ADLERCREUTZ, H., MAZUR, W. 1997. Phyto-oestrogens and Western diseases. Anal. Med. 29: 95–120.

    CAS  Google Scholar 

  22. MAZUR, W.M., DUKE, J.A., WÄHÄLÄ, K., RASKU, S., ADLERCREUTZ, H. 1998. Isoflavonoid and lignan in legumes: Nutritional and health aspects in humans. Nutr. Biochem. 9: 193–200.

    Article  CAS  Google Scholar 

  23. THOMPSON, L.U., ROBB, P., SERRAINO, M., CHEUNG, F. 1991. Mammalian lignan production from various foods. Nutr. Cancer 16: 43–52.

    CAS  Google Scholar 

  24. LEWIS, N.G., DAVIN, L.B., SARKANEN, S. 1999. The Nature and function of lignins. In: Comprehensive Natural Products Chemistry. Vol. 3. (Barton, Sir D.H.R., Nakanishi, K., Meth-Cohn, O., eds), Elsevier, London, pp 618–739.

    Google Scholar 

  25. REDDY, B.S., COHEN, LA., McCOY, G.D., HILL, P., WEISBURGER, J.H., WYNDER, E.L. 1989. Nutrition and its relation to cancer. Adv. Cancer Res. 32: 327–345.

    Google Scholar 

  26. KAMAL-ELDIN, A., PETTERSSON, D, APPELQVIST, L.-A. 1996. The in vivo antioxidant properties of sesame lignans. In: Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. (Kumpulainen, J.T., Salonen, J.K., eds), The Royal Society of Chemistry, Cambridge, England, pp 230–235.

    Chapter  Google Scholar 

  27. AKIMOTO, K., ASAMI, S., TANAKA, T., SHIMIZU, S., SUGANO, M., YAMADA, H. 1996. Antioxidant activity of sesamin on NADP-dependent lipid peroxidation in liver microsomes. In: Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. (Kumpulainen, J.T., Salonen, J.K., eds), The Royal Society of Chemistry, Cambridge, England, pp 241–246.

    Chapter  Google Scholar 

  28. MAZUR, W.M., WÄHÄLÄ, K., RASKU, S., SALALLA, A., HASE, T., ADLERCREUTZ, H. 1998. Lignan and isoflavonoid concentrations in tea and coffee. Br. J. Nutr. 79: 37–45.

    Article  PubMed  CAS  Google Scholar 

  29. GOEL, H.C., PRASAD, H.C., SHARMA, A. 1998. Antitumor and radioprotective action of Podophyllum hexandrum. Ind. J. Exp. Biol. 36: 583–587.

    CAS  Google Scholar 

  30. KO, K.M., IP, S.P., POON, M.K.T., WU, S.S., CHE, C.T., NG, K.H., KONG, Y.C. 1995. Effect of a lignan-enriched fructus schisandrae extract on hepatic glutathione status in rats: protection against carbon tetrachloride toxicity. Planta Medica 61: 134–137.

    Article  PubMed  CAS  Google Scholar 

  31. IP, S.P., MAK, D.H.F., LI, P.C., POON, M.K.T., KO, K.M. 1996. Effect of a lignan-enriched extract of Schisandra chinensis on aflatoxin Bl and cadmium chloride-induced hepatotoxicity in rats. Pharmacology and Toxicology 78: 413–416.

    Article  PubMed  CAS  Google Scholar 

  32. YAMADA, S., MURAWAKI, Y., KAWASAKI, H. 1993. Preventive effect of gomisin A, a lignan component of Schizandra fruits, on acetaminophen-induced hepatotoxicity in rats. Biochemical Pharmacology 46: 1081–1085.

    Article  PubMed  CAS  Google Scholar 

  33. OLIVETO, E.P. 1972. Nordihydroguaiaretic acid: A naturally occuring antioxidant. Chem. Ind.: 677–679.

    Google Scholar 

  34. GNABRE, J.N., BRADY, J.N., CLANTON, D.J., ITO, Y., DITTMER, J., BATES, R.B., HUANG, R.C.C. 1995. Inhibition of human immunodeficiency virus type 1 transcription and replication by DNA sequence-selective plant lignans. Proc. Natl. Acad. Sci. USA 92: 11239–11243.

    Article  PubMed  CAS  Google Scholar 

  35. GNABRE, J.N., ITO, Y., MA, Y., HUANG, R.C. 1996. Isolation of anti-HIV-1 lignans from Larrea tridentata by counter-current chromatography. J. Chromatogr. A 719: 353–364.

    Article  PubMed  CAS  Google Scholar 

  36. CHU, A., DINKOVA, A., DAVIN, L.B., BEDGAR, D.L., LEWIS, N.G. 1993. Stere-ospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia. J. Biol. Chem. 268: 27026–27033.

    PubMed  CAS  Google Scholar 

  37. DAVIN, L.B., BEDGAR, D., KATAYAMA, T., LEWIS, N.G. 1992. On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31: 3869–3874.

    Article  PubMed  CAS  Google Scholar 

  38. DAVIN, L.B., WANG, H.-B., CROWELL, A.L., BEDGAR, D.L., MARTIN, D.M., SARKANEN, S., LEWIS, N.G. 1997. Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275: 362–366.

    Article  PubMed  CAS  Google Scholar 

  39. DINKOVA-KOSTOVA, A.T., GANG, D.R., DAVIN, L.B., BEDGAR, D.L., CHU, A., LEWIS, N.G. 1996. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia: Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. J. Biol. Chem. 271: 29473–29482.

    Article  PubMed  CAS  Google Scholar 

  40. GANG, D.R., COSTA, M.A., FUJITA, M., DINKOVA-KOSTOVA, A.T., BURLAT, V., MARTIN, W., SARKANEN, S., DAVIN, L.B., LEWIS, N.G. 1999. Regiochemical control of monolignol radical coupling: A new paradigm for lignin and lignan biosynthesis. Chemistry & Biology 6: 143–151.

    Article  CAS  Google Scholar 

  41. KATAYAMA, T., DAVIN, L.B., LEWIS, N.G. 1992. An extraordinary accumulation of (−)-pinoresinol in cell-free extracts of Forsythia intermedia: Evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31: 3875–3881.

    Article  PubMed  CAS  Google Scholar 

  42. KATAYAMA, Y., DAVIN, L.B., CHU, A., LEWIS, N.G. 1993. Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 33(3): 581–591.

    Article  CAS  Google Scholar 

  43. UMEZAWA, T., DAVIN, L.B., KINGSTON, D.G.I., YAMAMOTO, E., LEWIS, N.G. 1990. Lignan biosynthesis in Forsythia sp. J. Chem. Soc., Chem. Commun.: 1405–1408.

    Google Scholar 

  44. UMEZAWA, T., DAVIN, L.B., LEWIS, N.G. 1990. Formation of the lignan, (−)-secoisolariciresinol by cell-free extracts of Forsythia intermedia. Biochem. Biophys. Res. Commun. 171(3): 1008–1014.

    Article  PubMed  CAS  Google Scholar 

  45. UMEZAWA, T., DAVIN, L.B., LEWIS, N.G. 1991. Formation of lignans, (−)-secoisolariciresinol and (−)-matairesinol with Forsythia intermedia cell-free extracts. J. Biol. Chem. 266: 10210–10217.

    PubMed  CAS  Google Scholar 

  46. XIA, Z.-Q., COSTA, M.A., DAVIN, L.B., LEWIS, N.G. 1999. Purification and characterization of (−)-secoisolariciresinol dehydrogenase: Cloning and recombinant expression.: (submitted).

    Google Scholar 

  47. SCHENK, P.M., BAUMANN, S., MATTES, R., STEINBIß, H.-H. 1995. Improved high-level expression system for eukaryotic genes in Escherichia coli using T7 RNA polymerase and rare ArgtRNAs. BioTechniques 19: 196–200.

    PubMed  CAS  Google Scholar 

  48. FUJITA, M., GANG, D.R., DAVIN, L.B., LEWIS, N.G. 1999. Recombinant pinoresinol/lariciresinol reductases from western red cedar (Thuja plicata) catalyse opposite enantiospecific conversions. J. Biol. Chem. 274: 618–627.

    Article  PubMed  CAS  Google Scholar 

  49. HAUMANN, B.F. 1993. Designer foods. Inform 4: 354–366.

    Google Scholar 

  50. HILDER, V.A., GATEHOUSE, A.M.R. 1990. Transforming plants as a means of crop protection against insects. Outlook on Agriculture 19: 179–183.

    Google Scholar 

  51. YOUNG, R. 1995. Improved tomato products: Utilising modern biotechnology. Food Australia: Official journal of CAFTA and AIFST 47: 203–204.

    Google Scholar 

  52. KRAMER, M.G., REDENBAUGH, K. 1994. Commercialization of a tomato with an antisense polygalacturonase gene: the FLAVR SAVR® tomato story. Euphytica 79: 293–297.

    Article  Google Scholar 

  53. SHINTANI, D., DELLAPENNA, D. 1998. Elevating the vitamin E content of plants through metabolic engineering. Science 282: 2098–2100.

    CAS  Google Scholar 

  54. BROWER, V 1998. Nutraceuticals: Poised for a healthy slice of the healthcare market? Nature Biotech. 16: 728–731.

    Article  CAS  Google Scholar 

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Costa, M.A., Xia, ZQ., Davin, L.B., Lewis, N.G. (1999). Toward Engineering the Metabolic Pathways of Cancer-Preventing Lignans in Cereal Grains and Other Crops. In: Romeo, J.T. (eds) Phytochemicals in Human Health Protection, Nutrition, and Plant Defense. Recent Advances in Phytochemistry, vol 33. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4689-4_4

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  • DOI: https://doi.org/10.1007/978-1-4615-4689-4_4

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