Phylogenetic Links in Plant Defense Systems: Lignans, Isoflavonoids, and Their Reductases

ACS Symposium Series

Volumn 658, Issue , 1997, Pages 58-89

  Gang, David R ^a   Dinkova Kostova, Albena T ^a   Davin, Laurence B ^a   Lewis, Norman G ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346542722     PISSN: 00976156     EISSN: None     Source Type: Book Series    
DOI: 10.1021/bk-1997-0658.ch006     Document Type: Article

References (103)

1. Lewis, N. G.; Kato, M. J.; Lopes, N.; Davin, L. B. In Chemistry of the Amazon, Biodiversity, Natural Products, and Environmental Issues; Seidl, P. R.; Gottlieb, O. R.; Kaplan, M. A. C., Eds.; ACS Symposium Series: Washington, DC, 1995, Vol. 588, pp 135-167.
2. Dahlgren, R. M. T. Bot. J. Linn. Soc. 1980, 80, 91-124.
3. Dahlgren, R. Nord. J. Bot. 1983, 3, 119-149.
4. Haworth, R. D. Ann. Rep. Progr. Chem. 1936, 33, 266-279.
5. Gottlieb, O. R.; Yoshida, M. In Natural Products of Woody Plants - Chemicals Extraneous to the Lignocellulosic Cell Wall; Rowe, J. W.; Kirk, C. H., Eds.; Springer Verlag: Berlin, 1989, pp 439-511.
6. Dewick, P. M. In The Flavonoids: Advances in Research Since 1986; Harborne, J. B., Ed.; Chapman & Hall: London, 1994, pp 117-238.
7. Davin, L. B.; Lewis, N. G. An. Acad. bras. Ci. 1995, 67 (Supl. 3), 363-378.
8. Dinkova-Kostova, A. T.; Gang, D. R.; Davin, L. B.; Bedgar, D. L.; Chu, A.; Lewis, N. G. J. Biol. Chem. 1996, 271, 29473-29482.
9. Wong, E. In The Flavonoids; Harborne, J. B.; Mabry, T. J.; Mabry, H., Eds.; Academic Press: New York, 1975, pp 743-800.
10. Hagmann, M.; Grisebach, H. FEBS Lett. 1984, 175, 199-202.
11. Paiva, N. L.; Edwards, R.; Sun, Y.; Hrazdina, G.; Dixon, R. A. Plant Mol. Biol. 1991, 17, 653-667.
12. Tiemann, K.; Inzé, D.; Van Montagu, M.; Barz, W. Eur. J. Biochem. 1991, 200, 751-757.
13. Paiva, N. L.; Sun, Y.; Dixon, R. A.; VanEtten, H. D.; Hrazdina, G. Arch. Biochem. Biophys. 1994, 312, 501-510.
14. Hibi, N.; Higashiguchi, S.; Hashimoto, T.; Yamada, Y. Plant Cell 1994, 6, 723-735.
15. van Eldik, G. J.; Ruiter, R. K.; van Herpen, M. M. A.; Schrauwen, J. A. M.; Wullems, G. J. EMBL accession number X92075 1995.
16. Petrucco, S.; Bolchi, A.; Foroni, C.; Percudani, R.; Rossi, G. L.; Ottenello, S. Plant Cell 1996, 8, 69-80.
17. Babiychuk, E.; Kushnir, S.; Belles-Boix, E.; Van Montagu, M.; Inze, D. EMBL accession number Z49777 1995.
18. Attucci, S.; Aitken, S. M.; Ibrahim, R. K.; Gulick, P. U. Genbank accession number U48590 1996.
19. Chu, A.; Dinkova, A.; Davin, L. B.; Bedgar, D. L.; Lewis, N. G. J. Biol. Chem. 1993, 268, 27026-27033.
20. Schlieper, D.; Tiemann, K.; Barz, W. Phytochemistry 1990, 29, 1519-1524.
21. Banks, S. W.; Steele, M. J.; Ward, D.; Dewick, P. M. J. Chem. Soc., Chem Commun. 1982, 157-158.
22. Dewick, P. M.; Ward, D. J. Chem. Soc., Chem. Commun. 1977, 338-339.
23. Taylor, T. N.; Taylor, E. L. The Biology and Evolution of Fossil Plants; Prentice Hall: Englewood Cliffs, NJ, 1993, pp 982.
24. Ayres, D. C.; Loike, J. D. Chemistry and Pharmacology of Natural Products. Lignans. Chemical, Biological and Clinical Properties; Cambridge University Press: Cambridge, England, 1990, pp 402.
25. Henges, A.; Petersen, M.; Alfermann, A. W. In Abstracts, Botanikertagung August 1996; Düsseldorf, 1996, p 253.
26. Takeda, R.; Hasegawa, J.; Shinozaki, M. Tetrahedron Lett. 1990, 31, 4159-4162.
27. Takeda, R.; Hasegawa, J.; Sinozaki, K. In Bryophytes. Their Chemistry and Chemical Taxonomy; Zinsmeister, H. D.; Mues, R., Eds.; Oxford University Press: New York, NY, 1990, Vol. 29, pp 201-207.
28. Wada, H.; Kido, T.; Tanaka, N.; Murakami, T.; Saiki, Y.; Chen, C.-M. Chem. Pharm. Bull. 1992, 40, 2099-2101.
29. Satake, T.; Murakami, T.; Saiki, Y.; Chen, C.-M. Chem. Pharm. Bull. 1978, 26, 1619-1622.
30. Miki, K.; Ito, K.; Sasaya, T. Mokuzai Gakkaishi 1979, 25, 665-670.
31. Anderegg, R. J.; Roe, J. W. Holzforschung 1974, 28, 171-175.
32. Briggs, L. H.; Cambie, R. C.; Hoare, J. L. Tetrahedron 1959, 7, 262-269.
33. Gardner, J. A. F.; Barton, G. M.; MacLean, H. Can. J. Chem. 1959, 37, 1703-1709.
34. Kupchan, S. M.; Stevens, K. L.; Rohlfing, E. A.; Sickles, B. R.; Sneden, A. T.; Miller, R. W.; Bryan, R. F. J. Org. Chem. 1978, 43, 586-590.
35. Kawanishi, K.; Uhara, Y.; Hashimoto, Y. Phytochemistry 1982, 21, 2725-2728.
36. Barata, L. E. S.; Baker, P. M.; Gottlieb, O. R.; Ruveda, E. A. Phytochemistry 1978, 17, 783-786.
37. Rao, C. B. S. Chemistry of Lignans; Andhra University Press: Waltair, India, 1978, pp 377.
38. Bohlmann, F.; Lonitz, M.; Knoll, K. Phytochemistry 1978, 17, 330-331.
39. Anjaneyulu, A. S. R.; Atchuta Ramaiah, P.; Ramachandra Row, L.; Venkateswarlu, R.; Pelter, A.; Ward, R. S. Tetrahedron 1981, 37, 3641-3652.
40. Munakata, K.; Marumo, S.; Ohta, K.; Chen, Y.-L. Tetrahedron Lett. 1965, 47, 4167-4170.
41. Ghogomu-Tih, R.; Bodo, B.; Nyasse, B.; Sondengam, B. L. Planta Medica 1985, 51, 464.
42. Hartley, R. D.; Ford, C. W. In Plant Cell Wall Polymers. Biogenesis and Biodegradation; Lewis, N. G.; Paice, M. G., Eds.; ACS Symposium Series: Washington, DC, 1989, Vol. 399, pp 137-145.
43. Ford, C. W.; Hartley, R. D. J. Sci. Food. Agric. 1990, 50, 29-43.
44. Adityachaudhury, N.; Gupta, P. K. Phytochemistry 1973, 12, 425-428.
45. Ahmed, M.; Shireen, K. F.; Rashid, M. A.; Ameen, M.-U. Planta Medica 1989, 55, 207-208.
46. Bentley, M. D.; Hassanali, A.; Lwande, W.; Njoroge, P. E. W.; Ole Sitayo, E. N.; Yatagai, M. Insect Sci. Applic. 1987, 8, 85-88.
47. Hijwegen, T. Phytochemistry 1973, 12, 375-380.
48. Ingham, J. L.; Markham, K. R. Z. Naturforsch. 1984, 39c, 13-17.
49. Kasymov, A. U.; Kondratenko, E. S.; Abubakirov, N. K. Chem. Nat. Prod. 1976, 10, 470-473.
50. Keen, N. T.; Sims, J. J.; Erwin, D. C.; Rice, E.; Partridge, J. E. Phytopathology 1971, 61, 1084-1089.
51. Kodama, T.; Yamakawa, T.; Minoda, Y. Agric. Biol. Chem. 1980, 44, 2387-2390.
52. Kole, R. K.; Satpathi, C.; Chowdhury, A.; Ghosh, M. R.; Adityachaudhury, N. J. Agric. Food Chem. 1992, 40, 1208-1210.
53. Lwande, W.; Hassanali, A.; Njoroge, P. W.; Bentley, M. D.; Delle Monache, F.; Jondiko, J. I. Insect Sci. Applic. 1985, 6, 537-541.
54. Lwande, W.; Bentley, M. D.; Hassanali, A. Insect Sci. Applic. 1986, 7, 501-503.
55. Lwande, W.; Bentley, M. D.; Macfoy, C.; Lugemwa, F. N.; Hassanali, A.; Nyandat, E. Phytochemistry 1987, 26, 2425-2426.
56. Kessmann, H.; Edwards, R.; Geno, P. W.; Dixon, R. A. Plant Physiol. 1990, 94, 227-232.
57. Graham, T. L. Plant Physiol. 1991, 95, 594-603.
58. Mackenbrock, U.; Vogelsang, R.; Barz, W. Z. Naturforsch. 1992, 47c, 815-822.
59. Barz, W.; Mackenbrock, U. Plant Cell Tissue Organ. Cult. 1994, 38, 199-211.
60. Dixon, R. A.; Paiva, N. L. Plant Cell 1995, 7, 1085-1097.
61. Anhut, S.; Zinsmeister, H. D.; Mues, R.; Barz, W.; Mackenbrock, K.; Köster, J.; Markham, K. R. Phytochemistry 1984, 23, 1073-1075.
62. Dewick, P. M. In The Flavonoids: Advances in Research; Harborne, J. B.; Mabry, T. M., Eds.; Chapman & Hall: London, 1982, pp 535-640.
63. Dewick, P. M. In The Flavonoids: Advances in Research Since 1980; Harborne, J. B., Ed.; Chapman & Hall: London, 1988, pp 125-210.
64. Tillekeratne, L. M. V.; Jayamanne, D. T.; Weerasuria, K. D. V.; Leslie Gunatilaka, A. A. Phytochemistry 1982, 21, 476-478.
65. Adlercreutz, H. Environ. Health Persp. 1995, 103 Suppl. 7, 103-112.
66. Taniguchi, E.; Imamura, K.; Ishibashi, F.; Matsui, T.; Nishio, A. Agric. Biol. Chem. 1989, 53, 631-643.
67. Yamauchi, S.; Taniguchi, E. Biosci. Biotech. Biochem. 1992, 56, 1744-1750.
68. Yamauchi, S.; Taniguchi, E. Biosci. Biotech. Biochem. 1992, 56, 1751-1759.
69. Yamauchi, S.; Ishibashi, F.; Taniguchi, E. Biosci. Biotech. Biochem. 1992, 56, 1760-1768.
70. Isogai, A.; Murakoshi, S.; Suzuki, A.; Tamura, S. Agric. Biol. Chem. 1973, 37, 889-895.
71. Hada, S.; Hattori, M.; Tezuka, Y.; Kikuchi, T.; Namba, T. Phytochemistry 1988, 27, 563-568.
72. González-Coloma, A.; Escoubas, P.; Mizutani, J.; Lajide, L. Phytochemistry 1994, 35, 607-610.
73. Nitao, J. K.; Nair, M. G.; Thorogood, D. L.; Johnson, K. S.; Scriber, J. M. Phytochemistry 1991, 30, 2193-2195.
74. Kamikado, T.; Chang, C.-F.; Murakoshi, S.; Sakurai, A.; Tamura, S. Agric. Biol. Chem. 1975, 39, 833-836.
75. Miyazawa, M.; Ishikawa, Y.; Kasahara, H.; Yamanaka, J.-I.; Kameoka, H. Phytochemistry 1994, 35, 611-613.
76. Matsui, K.; Munakata, K. Tetrahedron Lett. 1975, 24, 1905-1908.
77. Bowers, W. S. Science 1968, 161, 895-897.
78. Haller, H. L.; McGovran, E. R.; Goodhue, L. D.; Sullivan, W. N. J. Org. Chem. 1942, 7, 183-184.
79. Haller, H. L.; LaForge, F. B.; Sullivan, W. N. J. Org. Chem. 1942, 7, 185-188.
80. Bois, R.; Estabrook, R. W. Arch. Biochem. Biophys. 1969, 129, 362-369.
81. Fukami, H.; Nakajima, M. In Naturally Occurring Insecticides; Jacobson, M.; Crosby, D. G., Eds.; Marcel Dekker: NY, 1971, pp 71-97.
82. Lindahl, P. E.; Öberg, K. E. Exp. Cell Res. 1961, 23, 228-237.
83. Menz, R. I.; Griffith, M.; Day, D. A.; Wiskich, J. T. Eur. J. Biochem. 1992, 208, 481-485.
84. Storey, B. T. In Inhibitors of Mitochondrial Functions; Erecinska, M.; Wilson, D. F., Eds.; Pergamon Press: Elmsford, NY, 1981, pp 101-108.
85. Harmatha, J.; Nawrot, J. Biochem. Syst. Ecol. 1984, 12, 95-98.
86. Chitra, K. C.; Reddy, P. V. R.; Subbaraju, G. V.; Pillai, K. R. In Abstracts, 17th IUPAC International Symposium on the Chemistry of Natural Products; New Delhi, India, 1990, p 85.
87. González, J. A.; Estevez-Braun, A.; Estevez-Reyes, R.; Ravelo, A. G. J. Chem. Ecol. 1994, 20, 517-524.
88. González, J. A.; Estevez-Braun, A.; Estevez-Reyes, R.; Bazzocchi, I. L.; Moujir, L.; Jimenez, I. A.; Ravelo, A. G.; González, A. G. Experientia 1995, 51, 35-39.
89. Shain, L.; Hillis, W. E. Phytopathology 1971, 61, 841-845.
90. MacLean, H.; MacDonald, B. F. Can. J. Chem. 1967, 45, 739-740.
91. MacLean, H.; Murakami, K. Can. J. Chem. 1967, 45, 305-309.
92. Nakatani, N.; Ikeda, K.; Kikuzaki, H.; Kido, M.; Yamaguchi, Y. Phytochemistry 1988, 27, 3127-3129.
93. Hattori, M.; Hada, S.; Watahiki, A.; Ihara, H.; Shu, Y.-Z.; Kakiuchi, N.; Mizuno, T.; Namba, T. Chem. Pharm. Bull. 1986, 34, 3885-3893.
94. Takasugi, M.; Katui, N. Phytochemistry 1986, 25, 2751-2752.
95. Dixon, R. A.; Harrison, M. J.; Paiva, N. L. Physiol. Plant. 1995, 93, 385-392.
96. Higgins, V. J. Phytopathology 1978, 68, 339-345.
97. Duczek, L. J.; Higgins, V. J. Can. J. Bot. 1976, 54, 2620-2629.
98. Duczek, L. J.; Higgins, V. J. Can. J. Bot. 1976, 54, 2609-2619.
99. Perrin, D. R.; Cruickshank, I. A. M. Phytochemistry 1969, 8, 971-978.
100. Perrin, D. R.; Whittle, C. P.; Batterham, T. J. Tetrahedron Lett. 1972, 17, 1673-1676.
101. VanEtten, H. D.; Bateman, D. F. Phytopathology 1971, 61, 1363-1372.
102. Bailey, J. A.; Carter, G. A.; Skipp, R. A. Physiol. Plant Path. 1976, 8, 189-194.
103. Smith, D. A. Physiol. Plant Path. 1976, 9, 45-55.