Isoflavonoid biosynthesis and accumulation in developing soybean seeds

Plant Molecular Biology

Volumn 53, Issue 6, 2003, Pages 733-743

  Dhaubhadel, Sangeeta ^a   McGarvey, Brian D ^a   Williams, Ruthanne ^a   Gijzen, Mark ^a  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

F1 hybrids; Glycine max; Isoflavonoid inheritance; Phenylpropanoid; Secondary metabolism; Seed development

Indexed keywords

BIOSYNTHESIS; SEED; TISSUE;

PATHOGENS; SEED COAT;

MOLECULAR BIOLOGY;

GLYCINE MAX;

CARBON; CYTOCHROME P 450 CYP93C2 (GLYCYRRHIZA ECHINATA); CYTOCHROME P-450 CYP93C2 (GLYCYRRHIZA ECHINATA); CYTOCHROME P450; ISOENZYME; ISOFLAVONE DERIVATIVE; PHENYLALANINE;

ARTICLE; BIOSYNTHESIS; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETICS; GROWTH, DEVELOPMENT AND AGING; METABOLISM; PLANT SEED; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; SOYBEAN;

CARBON RADIOISOTOPES; CYTOCHROME P-450 ENZYME SYSTEM; GENE EXPRESSION REGULATION, ENZYMOLOGIC; GENE EXPRESSION REGULATION, PLANT; ISOENZYMES; ISOFLAVONES; PHENYLALANINE; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; SEEDS; SOYBEANS;

EID: 3242730436     PISSN: 01674412     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:PLAN.0000023666.30358.ae     Document Type: Article

References (40)

1. Akashi, T., Aoki, T. and Ayabe, S. 1999. Cloning and functional expression of a cytochrome P450 cDNA encoding 2-hydroxyisoflavanone synthase involved in biosynthesis of the isoflavonoid skeleton in licorice. Plant Physiol. 121: 821-828.
2. Altschul, S.F., Madden, T.L., Schaffer, A.A.. Zhang, J., Zhang, Z., Miller, W. and Lipman, D.J. 1997. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucl. Acids Res. 25: 3389-3402.
3. Anderson, J.W., Johnstone, B.M. and Cook-Newell, M.E. 1995. Meta-analysis of the effects of soy protein intake on serum lipids. N. Engl. J. Med. 333: 276-282.
4. Bhattacharyya, M.K. and Ward, E.W.B. 1987. Biosynthesis and metabolism of glyceollin I in soybean hypocotyls following wounding or inoculation with Phytophthora megasperma f.sp. glycinea. Physiol. Mol. Plant Path. 31: 387-405.
5. Cassidy, A. and Bingham, S. 1995. Biological effects of isoflavones in young women: importance of the chemical composition of soybean products. Br. J. Nutr. 74: 587-601.
6. Chen, S. and Halkier, B.A. 2000. Characterization of glucosinolate uptake by leaf protoplasts of Brassica napus. J. Biol. Chem. 275: 22955-22960.
7. Civitelli, R. 1997. In vitro and in vivo effects of ipriflavone on bone formation and bone biomechanics. Calcif. Tissue Int. 61: 12s-14s.
8. Du, L. and Halkier, B.A. 1998. Biosynthesis of glucosinolates in the developing silique walls. Phytochemistry 48: 1145-1150.
9. Eldridge, A.C. and Kwolek, W.F. 1983. Soybean isoflavones: effect of environment and variety on composition. J. Agric. Food Chem. 31: 394-396.
10. Ghosh, P. and Fenner, G.P. 1999. Improved method for gas chromatographic analysis of genistein and daidzein from soybean (Glycine max) seeds. J. Agric. Food Chem. 47: 3455-3456.
11. Gijzen, M., McGregor, I. and Seguin-Swart, G. 1989. Glucosinolate uptake by developing rapeseed embryos. Plant Physiol. 89: 260-263.
12. Graham, T.L. 1991. Flavonoid and isoflavonoid distribution in developing soybean seedlings tissues and in seed and root exudates. Plant Physiol. 95: 594-603.
13. Graham, T.L. 1995. Cellular biochemistry of phenylpropanoid responses of soybean to infection by Phytophthora sojae. In: M. Daniel and R.P. Purkayastha (Eds.) Handbook of Phytoalexin Metabolism and Action, Marcel Dekker, New York, pp. 85-116.
14. Graham, T.L. and Graham, M.Y. 2000. Defence potential and competency: redox conditioning effects of salicylic acid genistein. In: G. Stacey and N. Keen (Eds.) Plant-Microbe Interactions, APS Press, St. Paul, MN, Vol. 5, pp. 181-219.
15. Griffith, A.P. and Collison, M.W. 2001. Improved methods for the extraction and analysis of isoflavones from soy-containing foods and nutritional supplements by reversed-phase high-performance liquid chromatography and liquid chromatography-mass spectrometry. J. Chromatogr. A 913: 397-413.
16. Hakamatsuka, T., Mori, K., Ishida, S., Ebizuka, Y. and Sankawa, U. 1998. Purification of 2-hydroxyisoflavanone dehydratase from the cell cultures of Pueraria lobata. Phytochemistry 49: 497-505.
17. Heller, W. and Forkmann, G. 1994. Biosynthesis of flavonoids. In: J.B. Harborne (Ed.) The Flavonoids: Advances in Research since 1986, Chapman and Hall, London, pp. 499-535.
18. Jung, W., Yu, O., Lau, S.C., O'Keefe, D.P., Odell, J., Fader, G. and McGonigle, B. 2000. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Nature Biotech. 18: 208-212.
19. Kudou, S., Fleury, Y., Welt, D., Magnolato, D., Uchida, T. and Kitamura, K. 1991. Malonyl isoflavone glycosides in soybean seeds (Glycine mojc Merrill). Agric. Biol. Chem. 55: 2227-2233.
20. Liu, C., Blount, J.W., Steele, C.L. and Dixon, R.A. 2002. Bottlenecks for metabolic engineering of isoflavone glycoconjugates in Arabidopsis. Proc. Natl. Acad. Sci. USA 99: 14578-14583.
21. Lykkesfeldt, J. and Moller, B.L. 1993. Synthesis of benzylglucosinolate in Tropaeolus majus L.: isothiocyanates as potent enzyme inhibitors. Plant Physiol. 102: 609-613.
22. Magrath, R. and Mithen, R. 1993. Maternal effects on the expression of individual aliphatic glucosinolates in seeds and seedlings of Brassica napus. Plant Breed. 111: 249-252.
23. Meksem, K., Njiti, V.N., Banz, W.J., Iqbal, M.J., Kassem, M.M., Hyten, D.L., Yuang, J., Winters, T.A. and Lightfoot, D.A. 2001. Genomic regions that underlie soybean seed isoflavone content. J. Biomed. Biotech. 1: 38-44.
24. Mendez, M.A., Anthony, M.S. and Arab, L. 2002. Soy-based formulae and infant growth and development: a review. J. Nutr. 132: 2127-2130.
25. Messina, M. and Barnes, S. 1991. The role of soy products in reducing cancer risk. J. Natl. Cancer Inst. 83: 541-546.
26. Morris, P.F. and Ward, E.W.B. 1992. Chemoattraction of zoospores of the soybean pathogen, Phytophthora sojae, by isoflavones. Physiol. Mol. Plant Path. 40: 17-22.
27. Openshaw, S.J. and Hadley, H.H. 1978. Maternal effects on sugar content in soybean seeds. Crop Sci. 18: 581-584.
28. Peterson, G. and Barnes, S. 1991. Genistein inhibition of the growth of human breast cancer cells: independence from estrogen receptors and the multi-drug resistance gene. Biochem. Biophys. Res. Commun. 179: 661-667.
29. Phillips, D.A. 1992. Flavonoids: Plant signals to soil microbes. In: H.A. Stafford and R.K. Ibrahim (Eds.) Recent advances in Phytochemistry, Vol 26. Phenolic Metabolism in Plants, Plenum Press, New York, pp. 201-231.
30. Qutob, D., Hraber, P.T., Sobral, B.W.S. and Gijzen, M. 2000. Comparative analysis of expressed sequences in Phytophthora sojae. Plant Physiol. 123: 243-253.
31. Sawada, Y., Kinoshita, K., Akashi, T., Aoki, T. and Ayabe, S. 2002. Key amino acid residues required for aryl migration catalysed by the cytochrome P450 2-hydroxyisoflavanone synthase. Plant J. 31: 555-564.
32. Setchell, K.D.R., Zimmer-Nechemias, L., Cai, J. and Heubi, J.E. 1997. Exposure of infants to phytoestrogens from soy-based infant formula. Lancet 350: 23-27.
33. Shoemaker, R., Keim, P., Vodkin, L., Retzel, E., Clifton, S.W., Waterson, R., Smoller, D., Coryell, V., Khanna, A., Erpelding, J., Gai, X., Brendel, V., Raph-Schmidt, C., Shoop, E.G., Vielweber, C.J., Schmatz, M., Pape, D., Bowers, Y., Theising, B., Martin, J., Dante, M., Wylie, T. and Granger, C. 2002. A compilation of soybean ESTs: generation and analysis. Genome 45: 329-338.
34. Steele, C.L., Gijzen, M., Qutob, D. and Dixon, R.A. 1999. Molecular characterization of the enzyme catalyzing the aryl migration reaction of isoflavonoid biosynthesis in soybean. Arch. Biochem. Biophys. 367: 146-150.
35. Strom, B.L., Schinnar, R., Ziegle, E.E., Barhard, K.T., Sammel, M.D., Macones, G.A., Stallings, V.A., Drulis, J.M., Nelson, S.E. and Hanson, S.A. 2001. Exposure to soy-based formula in infancy and endocrinological and reproductive outcomes in young adulthood. J. Am. Med. Assoc. 286: 807-814.
36. Tsukamoto, C., Shimada, S., Igita, K., Kudou, S., Kokubun M., Okubo, K. and Kitamura, K. 1995. Factors affecting isoflavone content in soybean seeds: changes in isoflavones, saponins and composition of fatty acids at different temperatures during seed development. J. Agric. Food Chem. 43: 1184-1192.
37. Vyn, T.J., Yin, X.H., Brauulsema, T.W., Jackson, C.J.C., Rajcan, I. and Brouder, S.M. 2002. Potassium fertilization effects on isoflavone concentration in soybean [Glycine max (L.) Merr.]. J. Agric. Food Chem. 50: 3501-3506.
38. Wang, H.J. and Murphy, P.A. 1994. Isoflavone content in commercial soybean foods. J. Agric. Food Chem. 42: 1666-1673.
39. Wang, C.S. and Vodkin, L.O. 1994. Extraction of RNA from tissues containing high levels of procyanidins that bind RNA. Plant Mol. Biol. 12: 132-145.
40. Yu, O., Jung, W., Shi, J., Croes, R.A., Fader, G.M., McGonigle, B. and Odell, J.T. 2000. Production of the isoflavones genistein and daidzein in non-legume dicot and monocot tissues. Plant Physiol. 124: 781-793.