Dirigent proteins and dirigent sites explain the mystery of specificity of radical precursor coupling in lignan and lignin biosynthesis

Plant Physiology

Volumn 123, Issue 2, 2000, Pages 453-461

  Davin, Laurence B ^a   Lewis, Norman G ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING SITE; BIOSYNTHESIS; LIGNAN; LIGNIN; SPECIFICITY;

EID: 0034130986     PISSN: 00320889     EISSN: None     Source Type: Journal    
DOI: 10.1104/pp.123.2.453     Document Type: Review

References (46)

1. Adlercreutz H (1996) Lignans and isoflavonoids: epidemiology and a possible role in prevention of cancer. In JT Kumpulainen, JK Salonen, eds, Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. The Royal Society of Chemistry, Cambridge, UK, pp 349-355
2. Ayres DC, Loike JD (1990) Chemistry and pharmacology of natural products. In Lignans: Chemical, Biological and Clinical Properties. Cambridge University Press, Cambridge, UK
3. Bernards MA, Fleming WD, Llewellyn DB, Priefer R, Yang X, Sabatino A, Plourde GL (1999) Biochemical characterization of the suberization-associated anionic peroxidase of potato. Plant Physiol 121: 135-145
4. Bernards MA, Lewis NG (1998) The macromolecular aromatic domain in suberized tissue: a changing paradigm. Phytochemistry 47: 915-933
5. Bernards MA, Lopez ML, Zajicek J, Lewis NG (1995) Hydroxycinnamic acid-derived polymers constitute the polyaromatic domain of suberin. J Biol Chem 270: 7382-7386
6. Chattaway MM (1952) The sapwood-heartwood transition. Aust For 16: 25-34
7. Chu A, Dinkova A, Davin LB, Bedgar DL, Lewis NG (1993) Stereospecificity of (+)-pinoresinol and (+)-lariciresinol reductases from Forsythia intermedia. J Biol Chem 268: 27026-27033
8. Croteau R, Kutchan TM, Lewis NG (2000) Secondary metabolites. In BB Buchanan, W Gruissem, RL Jones, eds, Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologists, Rockville, MD (in press)
9. Davin LB, Bedgat DL, Katayama T, Lewis NG (1992) On the stereoselective synthesis of (+)-pinoresinol in Forsythia suspensa from its achiral precursor, coniferyl alcohol. Phytochemistry 31: 3869-3874
10. Davin LB, Lewis NG (1995) Lignin and lignan biochemical pathways in plants: an unprecedented discovery in phenolic coupling. An Acad Bras Cienc Suppl 3 67: 363-378
11. Davin LB, Wang H-B, Crowell AL, Bedgar DL, Martin DM, Sarkanen S, Lewis NG (1997) Stereoselective bimolecular phenoxy radical coupling by an auxiliary (dirigent) protein without an active center. Science 275: 362-366
12. Dinkova-Kostova AT, Gang DR, Davin LB, Bedgar DL, Chu A, Lewis NG (1996) (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia: protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. J Biol Chem 271: 29473-29482
13. Donaldson LA (1994) Mechanical constraints on lignin deposition during lignification. Wood Sci Technol 28: 111-118
14. Felsenstein J (1998) Phylogenies from molecular sequences: inference and reliability. Annu Rev Genet 22: 521-565
15. Ford JD, Davin LB, Lewis NG (1999) Plant lignans and health: cancer chemoprevention and biotechnological opportunities. In GG Gross, RW Hemingway, T Yoshida, eds, Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology. Kluwer Academic Publishers/Plenum Publishers, New York, pp 675-694
16. Fristensky B, Horovitz D, Hadwiger LA (1988) cDNA sequences for pea disease resistance response genes. Plant Mol Biol 11: 713-715
17. Fujita M, Gang DR, Davin LB, Lewis NG (1999) Recombinant pinoresinol/lariciresinol reductases from western red cedar (Thuja plicata) catalyze opposite enantiospecific conversions. J Biol Chem 274: 618-627
18. Fukuda Y, Nagata M, Osawa T, Namiki M (1986) A contribution of lignan analogues to antioxidative activity of refined unroasted sesame seed oil. J Am Oil Chem Soc 63: 1027-1031
19. Gang DR, Costa MA, Fujita M, Dinkova-Kostova AT, Wang H-B, Burlat V, Martin W, Sarkanen S, Davin LB, Lewis NG (1999) Regiochemical control of monolignol radical coupling: a new paradigm for lignin and lignan biosynthesis. Chem Biol 6: 143-151
20. Gang DR, Fujita M, Davin LB, Lewis NG (1998) The "abnormal lignins": mapping heartwood formation through the lignan biosynthetic pathway. In NG Lewis, S Sarkanen, eds, Lignin and Lignan Biosynthesis, Vol 697. ACS Symposium Series, Washington, DC, pp 389-421
21. Guan S-Y, Mlynár J, Sarkanen S (1997) Dehydrogenative polymerization of coniferyl alcohol on macromolecular lignin templates. Phytochemistry 45: 911-918
22. Hatakeyama T, Yoshida T, Hatakeyama H (1999) Thermal and viscoelastic properties of in situ lignin. In Proceeding of the 10th International Symposium on Wood and Pulping Chemistry, June 7-10, 1999, Yokohama, Japan, Vol 1. Japan TAPPI, Tokyo, pp 478-481
23. Henges A, Petersen M, Alfermann AW (1996) Localization of lignans in suspension-cultured cells of Linum album during the culture period. In Abstracts. Botanikertagung, Düsseldorf, p 253
24. Ishii H, Ishikawa T, Mihara M, Akaike M (1983) Studies on the chemical constituents of rutaceous plants: XLVIII. The chemical constituents of Xanthoxylum ailanthoides Sieb, et Zucc. [Fagara ailanthoides (Sieb, et Zucc.) Engl.]. (3) Isolation of the chemical constituents of the bark. Yakugaku Zasshi 103: 279-292
25. Jiao Y, Davin LB, Lewis NG (1998) Furanofuran lignan metabolism as a function of seed maturation in Sesamum indicant: methylenedioxy bridge formation. Phytochemistry 49: 387-394
26. Katayama T, Davin LB, Chu A, Lewis NG (1993) Novel benzylic ether reductions in lignan biogenesis in Forsythia intermedia. Phytochemistry 33: 581-591
27. Katayama T, Davin LB, Lewis NG (1992) An extraordinary accumulation of (-)-pinoresinol in cell-free extracts of Forsythia intermedia: evidence for enantiospecific reduction of (+)-pinoresinol. Phytochemistry 31: 3875-3881
28. Kwon M, Burlat V, Davin LB, Lewis NG (1999) Localization of dirigent protein involved in lignan biosynthesis: implications for lignification at the tissue and subcellular level. In GG Gross, RW Hemingway, T Yoshida, eds, Plant Polyphenols 2: Chemistry, Biology, Pharmacology, Ecology. Kluwer Academic Publishers/Plenum Publishers, New York, pp 393-411
29. Lewis NG (1999) A 20th century roller coaster ride: a short account of lignification. Curr Opin Plant Biol 2: 153-162
30. Lewis NG, Davin LB (1994) Evolution of lignin and neolignan biochemical pathways. In WD Nes, ed, Isopentenoids and Other Natural Products: Evolution and Function, Vol 562. ACS Symposium Series, Washington, DC, pp 202-246
31. Lewis NG, Davin LB (1998) The biochemical control of monolignol coupling and structure during lignan and lignin biosynthesis. In NG Lewis, S Sarkanen, eds, Lignin and Lignan Biosynthesis, Vol 697. ACS Symposium Series, Washington, DC, pp 334-361
32. Lewis NG, Davin LB (1999) Lignans: biosynthesis and function. In DHR Barton, K Nakanishi, O Meth-Cohn, eds, Comprehensive Natural Products Chemistry, Vol 1. Elsevier, London, pp 639-712
33. Lewis NG, Davin LB, Dinkova-Kostova AT, Ford JD, Fujita M, Gang DR, Sarkanen S, inventors, Novemer 7, 1997. Recombinant pinoresinol/lariciresinol reductase, recombinant dirigent protein, and methods of use. USA no. 09/475,316
34. Lewis NG, Davin LB, Sarkanen S (1998) Lignin and lignan biosynthesis: distinctions and reconciliations. In NG Lewis, S Sarkanen, eds, Lignin and Lignan Biosynthesis, Vol 697. ACS Symposium Series, Washington, DC, pp 1-27
35. Lewis NG, Davin LB, Sarkanen S (1999) The nature and function of lignins. In DHR Barton, K Nakanishi, O Meth-Cohn, eds, Comprehensive Natural Products Chemistry, Vol 3. Elsevier, London, pp 618-745
36. Lewis NG, Yamamoto E (1990) Lignin: Occurrence, biosynthesis and biodegradation. Annu Rev Plant Phys Plant Mol Biol 41: 455-496
37. Nagai H, Yakuo I, Aoki M, Teshima K, Ono Y, Sengoku T, Shimazawa T, Aburada M, Koda A (1989) The effect of gomisin A on immunologic liver injury in mice. Planta Med 55: 13-17
38. Negrel J, Pollet B, Lapierre C (1996) Ether-linked ferulic acid amides in natural and wound periderms of potato tuber. Phytochemistry 43: 1195-1199
39. Nomura M, Nakachiyama M, Hida T, Ohtaki Y, Sudo K, Aizawa T, Aburada M, Miyamoto K-I (1994) Gomisin A, a lignan component of Schizandra fruits, inhibits development of preneoplastic lesions in rat liver by 3′-methyl-4-dimethylamino-azobenzene. Cancer Lett 76: 11-18
40. Oliveto EP (1972) Nordihydroguaiaretic acid: a naturally occurring antioxidant. Chem Ind 677-679
41. Sarkanen KV, Ludwig CH (1971) Lignins: Occurrence, Formation, Structure and Reactions. Wiley Interscience, New York
42. Shen TY, Hwang S-B, Chang MN, Doebber TW, Lam M-HT, Wu MS, Wang X, Han GQ, Li RZ (1985) Characterization of a platelet-activating factor receptor antago nist isolated from haifenteng (Piper futokadsura): specific inhibition of in vitro and in vivo platelet-activating factor induced effects. Proc Natl Acad Sci USA 82: 672-676
43. Sterky F, Regan S, Karlsson J, Hertzberg M, Rohde A, Holmberg A, Amini B, Bhalerao R, Larsson M, Villarroel R, Van Montagu M, Sandberg G, Olsson O, Teeri TT, Boerjan W, Gustafsson P, Uhlén M, Sundberg B, Lundeberg J (1998) Gene discovery in the wood-forming tissues of poplar: analysis of 5,692 expressed sequence tags. Proc Natl Acad Sci USA 95: 13330-13335
44. Thompson LU, Orcheson L, Rickard S, Jenab M, Serraino M, Seidl M, Cheung F (1996) Anticancer effects of flax-seed lignans. In JT Kumpulainen, JK Salonen, eds, Natural Antioxidants and Food Quality in Atherosclerosis and Cancer Prevention. The Royal Society of Chemistry, Cambridge, UK, pp 356-364
45. Umezawa T, Davin LB, Kingston DGI, Yamamoto E, Lewis NG (1990) Lignan biosynthesis in Forsythia species. J Chem Soc Chem Commun 1405-1408
46. Umezawa T, Davin LB, Lewis NG (1991) Formation of lignans, (-)-secoisolariciresinol and (-)-matairesinol with Forsythia intermedia cell-free extracts. J Biol Chem 266: 10210-10217