Molecular cloning and characterization of a cDNA for pterocarpan 4-dimethylallyltransferase catalyzing the key prenylation step in the biosynthesis of glyceollin, a soybean phytoalexin

Plant Physiology

Volumn 149, Issue 2, 2009, Pages 683-693

  Akashi, Tomoyoshi ^a   Sasaki, Kanako ^b   Aoki, Toshio ^a   Ayabe, Shin Ichi ^a   Yazaki, Kazufumi ^b  

^a NIHON UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCINE MAX;

EID: 60249101275     PISSN: 00320889     EISSN: 15322548     Source Type: Journal    
DOI: 10.1104/pp.108.123679     Document Type: Article

References (39)

1. Akashi T, Aoki T, Ayabe S (1998) Identification of a cytochrome P450 cDNA encoding (2S)-flavanone 2-hydroxylase of licorice (Glycyrrhiza echinata L.; Fabaceae) which represents licodione synthase and flavone synthase II. FEBS Lett 431: 287-290
2. Akashi T, Aoki T, Ayabe S (2005) Molecular and biochemical characterization of 2-hydroxyisoflavanone dehydratase. Involvement of carboxylesterase-like proteins in leguminous isoflavone biosynthesis. Plant Physiol 137: 882-891
3. Asada Y, Li W, Yoshikawa T (2000) Biosynthesis of the dimethylallyl moiety of glabrol in Glycyrrhiza glabra hairy root cultures via a non-mevalonate pathway. Phytochemistry 55: 323-326
4. Ashby MN, Kutsunai SY, Ackerman S, Tzagoloff A, Edwards PA (1992) COQ2 is a candidate for the structural gene encoding para-hydroxybenzoate: polyprenyltransferase. J Biol Chem 267: 4128-4136
5. Ayabe S, Akashi T (2006) Cytochrome P450s in flavonoid metabolism. Phytochem Rev 5: 271-282
6. Biggs D, Welle R, Grisebach H (1990) Intracellular localization of prenyltransferases of isoflavonoid phytoalexin biosynthesis in bean and soybean. Planta 181: 244-248
7. Biggs DR, Welle R, Visser FR, Grisebach H (1987) Dimethylallylpyrophosphate: 3,9-dihydroxypterocarpan 10-dimethylallyl transferase from Phaseolus vulgaris. Identification of the reaction product and properties of the enzyme. FEBS Lett 220: 223-226
8. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254
9. Bräuer L, Brandt W, Schulze D, Zakharova S, Wessjohann L (2008) A structural model of the membrane-bound aromatic prenyltransferase UbiA from E. coli. ChemBioChem 9: 982-992
10. Dewick PM (1993) Isoflavonoids. In JB Harborne, ed, The Flavonoids. Advances in Research since 1986. Chapman and Hall, London, pp 117-238
11. Dixon RA (1999) Isoflavonoids: biochemistry, molecular biology, and biological functions. In U Sankawa, ed, Comprehensive Natural Products Chemistry, Vol 1. Polyketides and Other Secondary Metabolites Including Fatty Acids and Their Derivatives. Elsevier, Oxford, pp 773-823
12. Ebel J (1986) Phytoalexin synthesis: the biochemical analysis of the induction process. Annu Rev Phytopathol 24: 235-264
13. Ebel J, Grisebach H (1988) Defense strategies of soybean against the fungus Phytophthora megasperma f.sp. glycinea: a molecular analysis. Trends Biochem Sci 13: 23-27
14. Farag MA, Huhman DV, Dixon RA, Sumner LW (2008) Metabolomics reveals novel pathways and differential mechanistic and elicitor-specific responses in phenylpropanoid and isoflavonoid biosynthesis in Medicago truncatula cell cultures. Plant Physiol 146: 387-402
15. Graham TL, Kim JE, Graham MY (1990) Role of constitutive isoflavone conjugates in the accumulation of glyceollin in soybean infected with Phytophthora megasperma. Mol Plant Microbe Interact 3: 157-166
16. Hsieh MC, Graham TL (2001) Partial purification and characterization of a soybean β-glucosidase with high specific activity towards isoflavone conjugates. Phytochemistry 58: 995-1005
17. Laflamme P, Khouri H, Gulick P, Ibrahim R (1993) Enzymatic prenylation of isoflavones in white lupin. Phytochemistry 34: 147-151
18. Lichtenthaler HK, Rohmer M, Schwender J (1997) Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants. Physiol Plant 101: 643-652
19. Naoumkina M, Farag MA, Sumner LW, Tang Y, Liu CJ, Dixon RA (2007) Different mechanisms for phytoalexin induction by pathogen and wound signals in Medicago truncatula. Proc Natl Acad Sci USA 104: 17909-17915
20. Ober D (2005) Seeing double: gene duplication and diversification in plant secondary metabolism. Trends Plant Sci 10: 444-449
21. Ohara K, Yamamoto K, Hamamoto M, Sasaki K, Yazaki K (2006) Functional characterization of OsPPT1, which encodes p-hydroxybenzoate polyprenyltransferase involved in ubiquinone biosynthesis in Oryza sativa. Plant Cell Physiol 47: 581-590
22. Page RD (1996) TreeView: an application to display phylogenetic trees on personal computers. Comput Appl Biosci 12: 357-358
23. Sasaki K, Mito K, Ohara K, Yamamoto H, Yazaki K (2008) Cloning and characterization of naringenin 8-prenyltransferase, a flavonoid-specific prenyltransferase of Sophora flavescens. Plant Physiol 146: 1075-1084
24. Schopfer CR, Kochs G, Lottspeich F, Ebel J (1998) Molecular characterization and functional expression of dihydroxypterocarpan 6a-hydroxylase, an enzyme specific for pterocarpanoid phytoalexin biosynthesis in soybean (Glycine max L.). FEBS Lett 432: 182-186
25. Schröder G, Zähringer U, Heller W, Ebel J, Grisebach H (1979) Biosynthesis of antifungal isoflavonoids in Lupinus albus. Enzymatic prenylation of genistein and 2′-hydroxygenistein. Arch Biochem Biophys 194: 635-636
26. Shimada N, Sato S, Akashi T, Nakamura Y, Tabata S, Ayabe S, Aoki T (2007) Genome-wide analyses of the structural gene families involved in the legume-specific 5-deoxyisoflavonoid biosynthesis of Lotus japonicus. DNA Res 14: 25-36
27. Suzuki H, Takahashi S, Watanabe R, Fukushima Y, Fujita N, Noguchi A, Yokoyama R, Nishitani K, Nishino T, Nakayama T (2006) An isoflavone conjugate-hydrolyzing beta-glucosidase from the roots of soybean (Glycine max) seedlings: purification, gene cloning, phylogenetics, and cellular localization. J Biol Chem 281: 30251-30259
28. Tahara S, Ibrahim RK (1995) Prenylated isoflavonoids-an update. Phytochemistry 38: 1073-1094
29. Tarshis LC, Yan M, Poulter CD, Sacchettini JC (1994) Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution. Biochemistry 33: 10871-10877
30. Thompson JD, Higgins DG, Gibson TJ (1994) CLUSTALW: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 22: 4673-4680
31. Umemoto N, Kakitani M, Iwamatsu A, Yoshikawa M, Yamaoka N, Ishida I (1997) The structure and function of a soybean β-glucan-elicitor- binding protein. Proc Natl Acad Sci USA 94: 1029-1034
32. Veitch NC (2007) Isoflavonoids of the Leguminosae. Nat Prod Rep 24: 417-464
33. Welle R, Grisebach H (1988) Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers. Arch Biochem Biophys 263: 191-198
34. Welle R, Grisebach H (1991) Properties and solubilization of the prenyltransferase of isoflavonoid phytoalexin biosynthesis in soybean. Phytochemistry 30: 479-484
35. Yamamoto H, Zhao P, Inoue K (2002) Origin of two isoprenoid units in a lavandulyl moiety of sophoraflavanone G from Sophora flavescens cultured cells. Phytochemistry 60: 263-267
36. Yazaki K, Kunihisa M, Fujisaki T, Sato F (2002) Geranyl diphosphate: 4-hydroxybenzoate geranyltransferase from Lithospermum erythrorhizon. Cloning and characterization of a key enzyme in shikonin biosynthesis. J Biol Chem 277: 6240-6246
37. Yoshikawa M, Yamauchi K, Masago H (1978) Glyceollin: its role in restricting fungal growth in resistant soybean hypocotyls infected with Phytophthora megasperema var. sojae. Physiol Plant Pathol 12: 73-82
38. Zähringer U, Ebel J, Mulheirn LJ, Lyne RL, Grisebach H (1979) Induction of phytoalexin synthesis in soybean. Dimethylallylpyrophosphate: trihydroxypterocarpan dimethylallyl transferase from elicitor-induced cotyledons. FEBS Lett 101: 90-92
39. Zähringer U, Schaller E, Grisebach H (1981) Induction of phytoalexin synthesis in soybean. Structure and reactions of naturally occurring and enzymatically prepared prenylated pterocarpans from elicitor-treated cotyledons and cell cultures of soybean. Z Naturforsch [C] 36: 234-241