Molecular analysis of (R)-(+)-mandelonitrile lyase microheterogeneity in black cherry

Plant Physiology

Volumn 119, Issue 4, 1999, Pages 1535-1546

  Hu, Zihua ^a   Poulton, Jonathan E ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CDNA LIBRARY; CYANOGENESIS; FLAVINE ADENINE NUCLEOTIDE; FLAVOPROTEIN; GENE PROBE; GENETIC HETEROGENEITY; GLYCOSYLATION; INTRON; MANDELONITRILE LYASE; MICROHETEROGENEITY; MOLECULAR GENETICS; NORTHERN BLOTTING; OPEN READING FRAME; SOUTHERN BLOTTING;

EMBRYOPHYTA; PRUNUS SEROTINA;

EID: 0033117685     PISSN: 00320889     EISSN: None     Source Type: Journal    
DOI: 10.1104/pp.119.4.1535     Document Type: Article

References (60)

1. Ausubel FM, Brent R, Kingston RE, Moore DD, Seidman JG, Smith JA, Struhl K (1995) Current Protocols in Molecular Biology. John Wiley & Sons, New York
2. Baerwald KR, Jaenicke L (1978) D-Hydroxynitrile lyase: involvement of the prosthetic flavin adenine dinucleotide in enzyme activity. FEBS Lett 90: 255-260
3. Cheng I-P, Poulton JE (1993) Cloning of cDNA of Prunus serotina (R)-(+)-mandelonitrile lyase and identification of a putative FAD-binding site. Plant Cell Physiol 34: 1139-1143
4. Chrispeels MJ, Higgins TJV, Spencer D (1982) Assembly of storage protein oligomers in the endoplasmic reticulum and processing of the polypeptides in the protein bodies of developing pea cotyledons. J Cell Biol 93: 306-313
5. Darlington CD (1928) Studies in Prunus I, II. J Genet 19: 213-256
6. Dellaporta SL, Wood J, Hicks JB (1983) A plant DNA minipreparation: version II. Plant Mol Biol Rep 1: 19-21
7. Devereux J, Haeberli P, Smithies O (1984) A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res 12: 387-395
8. Effenberger F (1994) Synthesis and reactions of optically active cyanohydrins. Angew Chem Int Ed Engl 33: 1555-1564
9. Elgin SCR, Weintraub H (1975) Chromosomal proteins and chromatin structure. Annu Rev Biochem 44: 725-774
10. Felsenstein J (1985) Confidence limits on phylogenies: an approach using the bootstrap. Evolution 39: 783-791
11. Gerstner E, Steffen A, Pfeil E (1971) Zur Entwicklung der multiplen Formen des Flavin-Enzyms D-Oxynitrilase bei Prunus spinosa. Naturwissenschaften 58: 269-270
12. Griengl H, Hickel A, Johnson DV, Kratky C, Schmidt M, Schwab H (1997) Enzymatic cleavage and formation of cyanohydrins: a reaction of biological and synthetic relevance. Chem Comm 20: 1933-1951
13. Gross M, Jacobs GH, Poulton JE (1982) A rapid and sensitive spectrophotometric assay for prunasin hydrolase activity employing purified mandelonitrile lyase. Anal Biochem 119: 25-30
14. Hickel A, Hasslacher M, Griengl H (1996) Hydroxynitrile lyases: functions and properties. Physiol Plant 98: 891-898
15. Hsieh JS (1989) Cyanogenesis and aphid resistance in sorghum (abstract no. 74934). Chemical Abstracts 111: 462
16. Hu Z, Poulton JE (1997) Sequencing, genomic organization, and preliminary promoter analysis of a black cherry (R)-( + )-mandelonitrile lyase gene. Plant Physiol 115: 1359-1369
17. Jaenicke L, Preun J (1984) Chemical modification of hydroxynitrile lyase by selective reaction of an essential cysteine-SH group with α,β-unsaturated propiophenones as pseudosubstrates. Eur J Biochem 138: 319-325
18. Jones DA (1988) Cyanogenesis in animal-plant interactions. In D Evered, S Harnett, eds, Cyanide Compounds in Biology: Ciba Foundation Symposium No. 140. John Wiley & Sons, Chichester, UK, pp 151-176
19. Jorns M (1979) Mechanism of catalysis by the flavoenzyme oxynitrilase. J Biol Chem 254: 12145-12152
20. Kimura M (1980) A simple method for estimating evolutionary rates of base substitution through comparative studies of sequence evolution. J Mol Evol 16: 111-120
21. Lauble H, Müller K, Schindelin H, Förster S, Effenberger F (1994) Crystallization and preliminary X-ray diffraction studies of mandelonitrile lyase from almonds. Proteins 19: 343-347
22. LeGendre N, Mansfield M, Weiss A, Matsudaira P (1993) Purification of proteins and peptides by SDS-PAGE. In P Matsudaira, ed, A Practical Guide to Protein and Peptide Purification for Microsequencing. Academic Press, New York, pp 71-101
23. Li CP, Swain E, Poulton JE (1992) Prunus serotina amygdalin hydrolase and prunasin hydrolase: purification, N-terminal sequencing and antibody production. Plant Physiol 100: 282-290
24. Li W-H (1997) Molecular Evolution. Sinauer Associates, Sunderland, MA
25. Logemann J, Schell J, Willmitzer L (1987) Improved method for the isolation of RNA from plant tissues. Anal Biochem 163: 16-20
26. Markert CL (1984) Lactate dehydrogenase: biochemistry and function of lactate dehydrogenase. Cell Biochem Funct 2: 131-134
27. Maynard CA, Kavanagh K, Fuerukranz H, Drew AP (1991) I.1 Black cherry (Prunus serotina Ehrh.) In YPS Bajaj, ed, Biotechnology in Agricultural Forestry, Vol 16. Springer-Verlag, Berlin, pp 3-22
28. Mertz LM, Rashtchian A (1994) Nucleotide imbalance and polymerase chain reaction: effects on DNA amplification and synthesis of high specific activity radiolabeled DNA probes. Anal Biochem 221: 160-165
29. Møller BL, Poulton JE (1993) Cyanogenic glycosides. In PJ Lea, ed, Methods in Plant Biochemistry, Vol 9. Academic Press, San Diego, CA, pp 183-207
30. Mount SM (1982) A catalogue of splice junction sequences. Nucleic Acids Res 10: 459-472
31. Nahrstedt A (1985) Cyanogenic compounds as protecting agents for organisms. Plant Syst Evol 150: 35-47
32. Nahrstedt A (1992) The biology of the cyanogenic glycosides: new developments. In K Mengel, DJ Pilbeam, eds, Nitrogen Metabolism of Plants: Proceedings of the Phytochemical Society of Europe, Vol 33. Clarendon Press, Oxford, UK, pp 249-269
33. Ohno S (1970) Evolution by Gene Duplication. Springer-Verlag, Berlin
34. Poulton JE (1988) Localization and catabolism of cyanogenic glycosides. In D Evereds, S Harnett, eds, Cyanide Compounds in Biology: Ciba Foundation Symposium No. 140. John Wiley & Sons, Chichester, UK, pp 67-91
35. Poulton JE (1989) Toxic compounds in plant foodstuffs: cyanogens. In JE Kinsella, WG Soucie, eds, Food Proteins. American Oil Chemists' Society, Champaign, IL, pp 381-401
36. Poulton JE (1993) Enzymology of cyanogenesis in rosaceous stone fruits. In A Esen, ed, β-Glucosidases: Biochemistry and Molecular Biology. ACS Symposium Series No. 533. American Chemical Society, Washington, DC, pp 170-190
37. Rosenthaler L (1908) Asymmetric syntheses produced by enzymes. Biochem Z 14: 238-253
38. Saitou N, Nei M (1987) The neighbour-joining method: a new method for reconstructing phylogenetic trees. Mol Biol Evol 4: 406-425
39. Sambrook J, Fritsch EF, Maniatis T (1989) Molecular Cloning: A Laboratory Manual, Ed 2. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY
40. Sanger F, Nicklen S, Coulson AR (1977) DNA sequencing with chain-terminating inhibitors. Proc Natl Acad Sci USA 74: 5463-5467
41. Schröder J, Schamz S, Tropf S, Kircher B, Schröder G (1993) Phytoalexin biosynthesis: stilbene synthase and co-action of a reductase with chalcone synthase. In B Fritig, M Legrand, eds, Mechanisms of Plant Defense Response. Kluwer Academic Publishers, Dordrecht, The Netherlands, pp 257-267
42. Selmar D, Lieberei R, Biehl B, Conn EE (1989) α-Hydroxynitrile lyase in Hevea brasiliensis and its significance for rapid cyanogenesis. Physiol Plant 75: 97-101
43. Suelves M, Puigdomènech (1998) Molecular cloning of the cDNA coding for the (R)-(-t-)-mandelonitrile lyase of Prunus amygdalus: temporal and spatial expression patterns in flowers and mature seeds. Planta 206: 388-393
44. Swain E, Li CP, Poulton JE (1992a) Development of the potential for cyanogenesis in maturing black cherry (Prunus serotina Ehrh.) fruits. Plant Physiol 98: 1423-1428
45. Swain E, Li CP, Poulton JE (1992b) Tissue and subcellular localization of enzymes catabolizing (R)-amygdalin in mature Prunus serotina seeds. Plant Physiol 100: 291-300
46. Swain E, Poulton JE (1994a) Utilization of amygdalin during seedling development of Prunus serotina. Plant Physiol 106: 437-445
47. Swain E, Poulton JE (1994b) Immunocytochemical localization of prunasin hydrolase and mandelonitrile lyase in stems and leaves of Prunus serotina. Plant Physiol 106: 1285-1291
48. Tropf S, Lanz T, Rensing SA, Schröder J, Schröder F (1994) Evidence that stilbene synthases have developed from chalcone synthases several times in the course of evolution. J Mol Evol 38: 610-618
49. Trummler K, Wajant H (1997) Molecular cloning of acetone cyanohydrin lyase from flax (Linum usitatissimum). J Biol Chem 272: 4770-4774
50. von Heijne G (1986) A new method for predicting signal sequence cleavage sites. Nucleic Acids Res 14: 4683-4690
51. Wajant H, Effenberger F (1996) Hydroxynitrile lyases of higher plants. Biol Chem 377: 611-617
52. Wajant H, Förster S, Selmar D, Effenburger F, Pfizenmaier K (1995) Purification and characterization of a novel (R)-mandelonitrile lyase from the fern Phlebodium aureum. Plant Physiol 109: 1231-1238
53. Wajant H, Mundry K-W, Pfizenmaier K (1994) Molecular cloning of hydroxynitrile lyase from Sorghum bicolor (L.): homologies to serine carboxypeptidases. Plant Mol Biol 26: 735-746
54. Weeden NF (1983) Evolution of plant isozymes. In SD Tanksley, TJ Orton, eds, Developments in Plant Genetics and Breeding: Isozymes in Plant Genetics and Breeding, Part A. Elsevier, New York, pp 175-205
55. Wierenga RK, Terpstra P, Hol WGJ (1986) Prediction of the occurrence of the ADP-binding βαβ-fold in proteins, using an amino acid sequence fingerprint. J Mol Biol 187: 101-107
56. Wu H-C, Poulton JE (1991) Immunocytochemical localization of mandelonitrile lyase in mature black cherry (Prunus serotina Ehrh.) seeds. Plant Physiol 96: 1329-1337
57. Xu L-L, Singh BK, Conn EE (1986) Purification and characterization of mandelonitrile lyase from Prunus lyonii. Arch Biochem Biophys 250: 322-328
58. Xue J, Rask L (1995) The unusual 5′ splicing border GC is used in myrosinase genes of the Brassicaceae. Plant Mol Biol 29: 167-171
59. Yemm RS, Poulton JE (1986) Isolation and characterization of multiple forms of mandelonitrile lyase from mature black cherry (Prunus serotina Ehrh.) seeds. Arch Biochem Biophys 247: 440-145
60. Zheng L, Poulton JE (1995) Temporal and spatial expression of amygdalin hydrolase and (R)-(+)-mandelonitrile lyase in black cherry (Prunus serotina Ehrh.) seeds. Plant Physiol 109: 31-39