Stress responses in alfalfa (Medicago sativa L). XXII. cDNA cloning and characterization of an elicitor-inducible isoflavone 7-O-methyltransferase

Plant Molecular Biology

Volumn 36, Issue 1, 1998, Pages 43-54

  He, Xian Zhi ^a   Reddy, J T ^a   Dixon, Richard A ^a  

^a PLANT BIOLOGY DIVISION   (United States)

Author keywords

CDNA cloning; Cell culture; Isoflavone biosynthesis; Metabolic channeling; Phytoalexin

Indexed keywords

CELL CULTURE; CHICKPEA; COWPEA; DAIDZEIN; DNA ISOLATION; ISOFLAVONE; MEDICARPIN; METHYLATION; MOLECULAR CLONING; NORTHERN BLOTTING;

AMINO ACID SEQUENCE; BASE SEQUENCE; BENZOPYRANS; CLONING, MOLECULAR; CONSERVED SEQUENCE; DNA PRIMERS; DNA, COMPLEMENTARY; ENZYME INDUCTION; FABACEAE; GENE EXPRESSION REGULATION, PLANT; GENOME, PLANT; MEDICAGO SATIVA; METHYLTRANSFERASES; MOLECULAR SEQUENCE DATA; PEAS; PLANTS, MEDICINAL; POLYMERASE CHAIN REACTION; PTEROCARPANS; SEQUENCE ALIGNMENT; SUBSTRATE SPECIFICITY; TRANSCRIPTION, GENETIC;

CICER ARIETINUM; EMBRYOPHYTA; ESCHERICHIA COLI; MEDICAGO SATIVA; PISUM SATIVUM; SATIVUM;

EID: 0031881338     PISSN: 01674412     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1005938121453     Document Type: Article

References (52)

1. Baker CJ, O'Neill NR, Tomerlin RJ: Accumulation of phenolic compounds in incompatible clone/race interactions of Medicago sativa and Colletotrichum trifolii. Physiol Plant Path 35: 231-241 (1989).
2. Blount JW, Dixon RA, Paiva NL: Stress responses in alfalfa (Medicago sativa L.). XVI. Antifungal activity of medicarpin and its biosynthetic precursors; implications for the genetic manipulation of stress metabolites. Physiol Mol Plant Path 41: 333-349 (1992).
3. Bugos RC, Chiang VLC, Campbell WH: cDNA cloning, sequence analysis and seasonal expression of lignin-bispecific caffeic acid/5-hydroxyferulic acid O-methyltransferase of aspen. Plant Mol Biol 17: 1203-1215 (1991).
4. Chomcynski P, Sacchi N: Single-step method of RNA isolation by acid guanidinium thiocyanate-phenol-chloroform extraction. Anal Biochem 162: 156-159 (1987).
5. Collazo P, Montoliu L, Puigdomenech P, Rigau J: Structure and expression of the lignin O-methyltransferase gene from Zea mays L. Plant Mol Biol 20: 857-867 (1992).
6. Dalkin K, Edwards R, Edington B, Dixon RA: Stress responses in alfalfa (Medicago sativa L.) 1. Induction of phenylpropanoid biosynthesis and hydrolytic enzymes in elicitor-treated cell suspension cultures. Plant Physiol 92: 440-446 (1990).
7. Daniell T, O'Hagant D, Edwards R: Alfalfa cell cultures treated with a fungal elicitor accumulate flavone metabolises rather than isoflavones in the presence of the methylation inhibitor tubericidin. Phytochemistry 44: 285-291 (1997).
8. Dellaporta SL, Wood J, Hicks JB: A plant DNA minipreparation: Version II. Plant Mol Biol Rep 1: 19-21 (1983).
9. Dewick PM: Isoflavonoids. In: Harbone JB (ed) The Flavonoids: Advances in Research Since 1980, pp. 125-209. Chapman & Hall, London (1988).
10. Dewick PM, Martin M: Biosynthesis of pterocarpan and isoflavan phytoalexins in Medicago sativa: the biochemical inter-conversion of pterocarpans and 2́-hydroxyisoflavans. Phytochemistry 18: 591-596 (1979).
11. Dewick PM, Martin M: Biosynthesis of pterocarpan, isoflavan and coumestan metabolises of Medicago sativa: chalcone, isoflavone and isoflavanone precursors. Phytochemistry 18: 597-602 (1979).
12. Dixon RA, Choudhary AD, Dalkin K, Edwards R, Fahrendorf T, Gowri G, Harrison MJ, Lamb CJ, Loake GJ, Maxwell CA, Orr J, Paiva NL: Molecular biology of stress-induced phenylpropanoid and isoflavonoid biosynthesis in alfalfa. In: Stafford HA, Ibrahim RK (eds) Recent Advances in Phytochemistry 26: 91-138. Plenum Press, New York (1992).
13. Eckenrode VK, Arnold J, Meagher RB: Comparison of the nucleotide sequence of soybean 18s rRNA with the sequences of other small-subunit rRNAs. J Mol Evol 21: 259-269 (1985).
14. Edwards R, Dixon RA: Isoflavone-O-methyltransferase activities in elicitor-treated cell suspension cultures of Medicago sativa. Phytochemistry 3O: 2597-2606 (1991).
15. Edwards R, Kessmann H: Isoflavonoid phytoalexins and their biosynthetic enzymes. In: Gurr SJ, McPherson MJ, Bowles DJ (eds) Molecular Plant Pathology: A Practical Approach, vol. 2, pp. 45-62. IRL Press, Oxford (1992).
16. Frech CJ, Elder M, Leggett F, Ibrahim RK, Towers GHN: Flavonoids inhibit tobacco mosaic virus infectivity. Can J Plant Path 13: 1-6 (1991).
17. Cauthier A, Culick PJ, Ibrahim RK: cDNA cloning and characterization of a 3′/5′-O-methyltransferase for partially methylated flavonols from Chrysosplenium americanum. Plant Mol Biol 32: 1163-1169 (1996).
18. Gregersen PL, Christensen AB, Sommer-Knudsen J, Collinge DB: A putative O-methyltransferase from barley is induced by fungal pathogens and UV light. Plant Mol Biol 26: 1797-1806 (1994).
19. Guo L, Paiva NL: Molecular cloning and expression of alfalfa (Medicago sativa L.) vestitone reductase, the penultimate enzyme in medicarpin biosynthesis. Arch Biochem Biophys 320: 353-360 (1995).
20. Hagmann M, Grisebach H: Enzymatic rearrangement of flavanone to isoflavone. FEBS Lett 175: 199-202 (1984).
21. Hakamatsuka T, Ebizuka Y, Sankawa U: Pueraria lobata (Kudzu vine): in vitro culture and the production of isoflavonoids. In: Bajaj YPS (ed) Biotechnology in Agriculture and forestry Vol. 28, pp. 386-397, Springer-Verlag, Berlin/Heidelberg (1994).
22. Hashim MF, Hakamatsuka T, Ebizuka Y, Sankawa U: Reaction mechanism of oxidative rearrangement of flavanone in isoflavone biosynthesis. FEBS Lett 271: 219-222 (1990).
23. He XZ, Dixon RA: Affinity chromatography, substrate/product specificity, and amino acid sequence analysis of an isoflavone O-methyltransferase from alfalfa (Medicago sativa L.). Arch Biochem Biophys 336: 121-129 (1996).
24. Held BM, Wang H, John I, Wurtele ES, Collbert JT: An mRNA putatively coding for an O-methyltransferase accumulates preferentially in maize roots and is located predominantly in the region of the endodermis. Plant Physiol 102: 1001-1008 (1993).
25. Heller W, Forkmann G: Biosynthesis of flavonoids. In: Harborne JB (ed) The Flavonoids: Advances in Research Since 1986, pp. 516-517. Chapman & Hall, London (1993).
26. Higgins VJ: Role of the phytoalexin medicarpin in three leaf spot diseases of alfalfa. Physiol Plant Path 2: 289-300 (1972).
27. Hinderer W, Flentje U, Barz W: Microsomal isoflavone 2′-and 3-hydroxylase from chickpea (Cicer arietinum L.) cell suspensions induced for pterocarpan phytoalexin formation. FEBS Lett 214: 101-106 (1987).
28. Ingham JL: Phytoalexins from the leguminosae In: Bailey JA, Mansfield JW (eds) Phytoalexins pp. 21-80. John Wiley, New York (1982).
29. Ingham JL, Keen NT, Mulheirn LJ, Lyne RL: Inducibly-formed isoflavonoids from leaves of soybean. Phytochemistry 20: 795-798 (1981).
30. Joshi CP: An inspection of the domain between putative TATA box and translation start site in 79 plant genes. Nucl Acids Res 15: 6643-6653 (1987).
31. Joshi CP: Putative polyadenylation signals in nuclear genes of higher plants: a compilation and analysis. Nucl Acids Res 15: 9627-9640 (1987).
32. Jorrin J, Dixon RA: Stress responses in alfalfa (Medicago sativa L). II. Purification, characterization and induction of phenylalanine ammonia-lyase isoforms from elicitor-treated cell suspension cultures. Plant Physiol 92: 447-455 (1988).
33. Junghans H, Dalkin K, Dixon RA: Stress responses in alfalfa (Medicago sativa L). 15. Characterization and expression patterns of members of a subset of the chalcone synthase multigene family. Plant Mol Biol 22: 239-253 (1993).
34. Kagan RM, Clarke S: Widespread occurrence of three sequence motifs in diverse S-adenosylmethionine-dependent methyltransferases suggests a common structure for these enzymes. Arch Biochem Biophys 310: 417-427 (1994).
35. . Kessmann H, Choudhary AD, Dixon RA: Stress responses in alfalfa (Medicago sativa L). III. Induction of medicarpin and cytochrome P450 enzyme activities in elicitor-treated cell suspension cultures and protoplasts. Plant Cell Rep 9: 38-41 (1990).
36. Kobayashi A, Yata S, Kawazu K: A O-hydroxychalcone and flavonoids from alfalfa callus stimulated by a fungal naphthoquinone, PO-1. Agric Biol Chem 52: 3223-3227 (1988).
37. Kochs K, Crisebach H: Enzymic synthesis of isoflavones. Eur J Biochem 155: 311-318 (1986)
38. Leni P, Barz W, Grisebach H: On the incorporation of 5,7,4′-trihydroxyflavanone-[2,6,8,10 C14] into cyanidin and the isoflavone biochanin A and formononetin. Z Naturforsch 19b: 1110-1113 (1964).
39. Luckner M: Secondary Metabolism in Microorganisms, Plants and Animals. Springer-Verlag, Berlin (1990).
40. Martin M, Dewick, PM: Biosynthesis of pterocarpan, isoflavan and coumestan metabolises of Medicago sativa: the role of an isoflav-3-ene. Phytochemistry 19: 2341-2346 (1980).
41. Maxwell CA, Harrison MJ, Dixon RA: Molecular characterization and expression of alfalfa isoliquiritigenin 2′-O-methyltransferase, an enzyme specifically involved in the biosynthesis of an inducer of Rhizobium meliloti modulation genes. Plant J 4: 971-981 (1993).
42. Olah AF, Sherwood RT: Flavones, isoflavones, and coumestans in alfalfa infected by Ascochyta imperfecta. Phytopathology 61: 65-69 (1971).
43. O'Neill NR, Saunders JA: Compatible and incompatible responses in alfalfa cotyledons to races 1 and 2 of Colletotrichum trifolii. Phytopathology 84: 283-287 (1994).
44. Paiva NL, Edwards R, Sun Y, Hrazdina G, Dixon RA: Stress responses in alfalfa (Medicago sativa L). 11. Molecular cloning and expression of alfalfa isoflavone reductase, a key enzyme of isoflavonoid phytoalexin biosynthesis. Plant Mol Biol 17: 653-667 (1991).
45. Parry A, Edwards R: Characterization of flavonoid O-glycosyltransferases from alfalfa (Medicago sativa L.). Acta Hort 381: 154-157 (1994).
46. Preston NW, Chamberlain K, Skipp RA: A 2-arylbenzofuran phytoalexin from cowpea (Vigna unguiculata). Phytochemistry 14: 1843-1844 (1975).
47. Sambrook J, Fritsch EF, Maniatis T: Molecular Cloning: A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY (1989).
48. Stoessl A: Biosynthesis of phytoalexins. In: Bailey JA, Mansfield JW (eds) Phytoalexins pp. 133-180. John Wiley, New York (1982).
49. Tiller SA, Parry AD, Edwards R: Changes in the accumulation of flavonoid and isoflavonoid conjugates associated with plant age and modulation in alfalfa (Medicago sativa). Physiol Plant 91: 27-36 (1994).
50. Wengenmayer H, Ebel J, Crisebach H: Purification and properties of a S-adenosylmethionine: isoflavone 4′-O-methyltransferase from cell suspension cultures of Cicer arietinum L. Eur J Biochem 50: 135-143 (1974).
51. Wong E, Francis CM: Flavonoids in genotypes of Trifolium subterraneum. II. Mutants of the Geraldton variety. Phytochemistry 7: 2131-2137 (1968).
52. Woodward MD: Identification of the biosynthetic precursors of medicarpin in inoculation droplets on white clover. Physiol Plant Path 18: 33-39 (1981).