Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum

Plant Physiology

Volumn 115, Issue 4, 1997, Pages 1661-1670

  Kahn, Rachel Alice ^a   Bak, Søren ^a   Svendsen, Ib ^b   Halkier, Barbara Ann ^a   Møller, Birger Lindberg ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXYMANDELONITRILE; 4 HYDROXYPHENYLACETALDOXIME; 4 HYDROXYPHENYLACETONITRILE; AMINO ACID SEQUENCE; BIOSYNTHESIS; CATALYSIS; COLUMN CHROMATOGRAPHY; CYTOCHROME P450; DHURRIN; DILAUROYLPHOSPHATIDYLCHOLINE; GLUCOSIDE; ION EXCHANGE CHROMATOGRAPHY; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; PARTITIONING; PROTEIN ISOLATION; SOLUBILIZATION; SORGHUM; URIDINE DIPHOSPHATE GLUCOSE GLUCOSYLTRANSFERASE;

SORGHUM BICOLOR;

EID: 0031397803     PISSN: 00320889     EISSN: None     Source Type: Journal    
DOI: 10.1104/pp.115.4.1661     Document Type: Article

References (44)

1. Abrol YP, Conn EE (1966) Studies on cyanide metabolism in Lotus arabicus L. and Lotus tenuis L. Phytochemistry 5: 237-242
2. Altschul ST, Gish W, Miller W, Myers EW, Lipman DJ (1990) Basic local alignment search tool. J Mol Biol 215: 403-410
3. Amade P, Mallea M, Bouaicha N (1994) Isolation, structural identification and biological activity of two metabolites produced by Penicillium olsonii Bainier and Sartory. J Antibiot 47: 201-207
4. Bak S, Kahn RA, Nielsen HL, Møller BL, Halkier BA (1997a) Cloning of three A-type cytochromes P450, CYP71E1, CYP98, and CYP99 from Sorghum bicolor (L.) Moench by a PCR approach, and identification by expression in Escherichia coli of CYP71E1 as the oxime-metabolizing cytochrome P450 in the biosynthesis of the cyanogenic glucoside dhurrin. Plant Mol Biol (in press)
5. Bak S, Kahn RA, Olsen CE, Halkier BA (1997b) Cloning and expression in Escherichia coli of the obtusifoliol 14α-demethylase of Sorghum bicolor (L.) Moench, a cytochrome P450 orthologous to the sterol 14α-demethylases (CYP51) from fungi and mammals. Plant J 11: 191-201
6. Bennett R, Ludwig-Muller J, Kiddle G, Hilgenberg W, Wallsgrove R (1995) Developmental regulation of aldoxime formation in seedlings and mature plants of Chinese cabbage (Brassica campestris ssp. pekinensis) and oilseed rape (Brassica napus): glucosinolate and IAA biosynthetic enzymes. Planta 196: 239-244
7. Benveniste I, Gabriac B, Durst F (1986) Purification and characterization of the NADPH-cytochrome P-450 (cytochrome c) reductase from higher-plant microsomal fraction. Biochem J 235: 365-373
8. Berkelman T, Houtchens KA, DuPont FM (1994) Two cDNA clones encoding isoforms of the B subunit of the vacuolar ATPase from barley roots. Plant Physiol 104: 287-288
9. Boucher J-L, Delaforge M, Mansuy D (1994) Dehydration of alkyl-and arylaldoximes as a new cytochrome P450-catalyzed reaction: mechanism and stereochemical characteristics. Biochemistry 33: 7811-7818
10. Colowick SP, Kaplan NO, Ciotti MM (1951) The reaction of pyridine nucleotide with cyanide and its analytical use. J Biol Chem 191: 447-459
11. Davis RH, Nahrstedt A (1987) Biosynthesis of cyanogenic glucosides in butterflies and moths: effective incorporation of 2-methylpropanenitrile and 2-methylbutanenitrile into linamarin and lotaustralin by Zygaena and Heliconius species (Lepidoptera). Insect Biochem 17: 689-693
12. Dehmlow EV, Sleegers A, Risch N, Trowitzsch-Kienast W, Wray V, Gunatilaka AAL (1990) Structure revision of a minor alkaloid from Broussonetia zeylanica. Phytochemistry 29: 3993-3996
13. DeMaster EG, Shirota FN, Nagasawa HT (1992) A Beckmann-type dehydration of n-butyraldoxime catalyzed by cytochrome P-450. J Org Chem 57: 5074-5075
14. Du L, Lykkesfeldt J, Olsen CE, Halkier BA (1995) Involvement of a cytochrome P450 in glucosinolate biosynthesis as demonstrated by an in vitro microsomal enzyme system isolated from jasmonic acid-induced seedlings of Sinapis alba L. Proc Natl Acad Sci USA 92: 12505-12509
15. Fling SP, Gregerson DS (1986) Peptide and protein molecular weight determination by electrophoresis using a high-molarity Tris buffer without urea. Anal Biochem 155: 83-88
16. Grootwassink JWD, Balsevich JJ, Kolenovsky AD (1990) Formation of sulfatoglucosides from exogenous aldoximes in plant cell cultures and organs. Plant Sci 66: 11-20
17. Halkier BA, Møller BL (1989) Biosynthesis of the cyanogenic glucoside dhurrin in seedlings of Sorghum bicolor (L.) Moench and partial purification of the enzyme system involved. Plant Physiol 90: 1552-1559
18. Halkier BA, Møller BL (1990) The biosynthesis of cyanogenic glucosides in higher plants. J Biol Chem 265: 21114-21121
19. Halkier BA, Møller BL (1991) Involvement of cytochrome P-450 in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench. Plant Physiol 96: 10-17
20. TYR expressed at high levels in Escherichia coli. Arch Biochem Biophys 322: 369-377
21. Halkier BA, Olsen CE, Møller BL (1989) The biosynthesis of cyanogenic glucosides in higher plants: the (E)- and (Z)-isomers of p-hydroxyphenylacetaldehyde oxime as intermediates in the biosynthesis of dhurrin in Sorghum bicolor (L.) Moench. J Biol Chem 264: 19487-19494
22. Halkier BA, Scheller HV, Møller BL (1988) Cyanogenic glucosides: the biosynthetic pathway and the enzyme system involved. CIBA Found Symp 140: 49-66
23. 14C)-N-hydroxyisoleucine into linamarin and lotaustralin by the larvae of Zygaena trifolii. Insect Biochem Mol Biol 24: 161-165
24. Imai Y, Sato R (1967) Conversion of P-450 to P-420 by neutral salts and some other reagents. Eur J Biochem 1: 419-426
25. Ito C, Tanahashi S, Tani Y, Juichi M, Omura M, Furukawa H (1990) Isolation of new constituents from citrus plants. Chem Pharm Bull 38: 2586-2588
26. Jefcoate CR (1978) Measurement of substrate and inhibitor binding to microsomal cytochrome P-450 by optical-difference spectroscopy. Methods Enzymol 27: 258-279
27. Kahn RA, Bak S, Olsen CE, Svendsen I, Møller BL (1996) Isolation and reconstitution of the heme-thiolate protein obtusifoliol 14α-demethylase from Sorghum bicolor (L.) Moench. J Biol Chem 271: 32944-32950
28. Kindl H, Schiefer S (1971) Aldoximes as intermediates in the biosynthesis of tyrosol and tyrosol derivatives. Phytochemistry 10: 1795-1802
29. Koch BM, Sibbesen O, Halkier BA, Svendsen I, Møller BL (1995) The primary sequence of cytochrome P450tyr, the multifunctional N-hydroxylase catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. Arch Biochem Biophys 323: 177-186
30. McFarlane IJ, Lees EM, Conn EE (1975) The in vitro biosynthesis of dhurrin, the cyanogenic glucoside of Sorghum bicolor. J Biol Chem 250: 4708-4713
31. Møller BL, Conn EE (1979) The biosynthesis of cyanogenic glucosides in higher plants. N-Hydroxytyrosine as an intermediate in the biosynthesis of dhurrin by Sorghum bicolor (L.) Moench. J Biol Chem 254: 8575-8583
32. Møller BL, Conn EE (1980) The biosynthesis of cyanogenic glucosides in higher plants: channelling of intermediates in dhurrin biosynthesis by a microsomal enzyme system from Sorghum bicolor (Linn.) Moench. J Biol Chem 255: 3049-3056
33. Omura T, Sato R (1964) The carbon monoxide-binding pigment of liver proteins. II. Solubilization, purification, and properties. J Biol Chem 239: 2379-2385
34. Poulton JE (1990) Cyanogenesis in plants. Plant Physiol 94: 401-405
35. Reay PF, Conn EE (1974) The purification and properties of a uridine diphosphate glucose:aldehyde cyanohydrin β-glucosyl-transferase from sorghum seedlings. J Biol Chem 249: 5826-5830
36. Robbing JH (1966) Preparation and properties of p-hydroxyphenylacetaldehyde and 3-methoxy-4-hydroxyphenylacetaldehyde. Arch Biochem Biophys 114: 576-584
37. Saul R, Chambers JP, Molyneux RJ, Elbein AD (1983) Castanospermine, a tetrahydroxylated alkaloid that inhibits β-glucosidase and β-glucocerobrosidase. Arch Biochem Biophys 221: 593-597
38. Scofield AM, Rossiter JT, Witham P, Kite GC, Nash JR, Fellows LE (1990) Inhibition of thioglucosidase-catalysed glucosinolate hydrolysis by castanospermine and related alkaloids. Phytochemistry 29: 107-109
39. Shimada M, Conn EE (1977) The enzymatic conversion of p-hydroxyphenylacetaldoxime to p-hydroxymandelonitrile. Arch Biochem Biophys 180: 199-207
40. TYR' which catalyzes the committed step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. Proc Natl Acad Sci USA 91: 9740-9744
41. TYR is a multifunctional heme-thiolate enzyme catalyzing the conversion of L-tyrosine to p-hydroxyphenylacetaldehyde oxime in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor (L.) Moench. J Biol Chem 270: 3506-3511
42. Takabayashi J, Dicke M, Takahashi S, Posthumus MA, Van-Beek TA (1994) Leaf age affects composition of herbivore-induced synomones and attraction of predatory mites. J Chem Ecol 20: 373-386
43. Tapper BA, Butler GW (1972) 2-Hydroxyaldoximes as possible precursors in the biosynthesis of cyanogenic glucosides. Phytochemistry 11: 1041-1046
44. 5. Anal Biochem 197: 125-131