Glucosinolate biosynthesis: Demonstration and characterization of the condensing enzyme of the chain elongation cycle in Eruca sativa

Phytochemistry

Volumn 65, Issue 8, 2004, Pages 1073-1084

  Falk, Kimberly L ^a   Vogel, Christine ^a,c   Textor, Susanne ^a   Bartram, Stefan ^a   Hick, Alastair ^b   Pickett, John A ^b   Gershenzon, Jonathan ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ECOLOGY   (Germany)

^b ROTHAMSTED RESEARCH   (United Kingdom)

^c MRC LABORATORY OF MOLECULAR BIOLOGY   (United Kingdom)

Author keywords

Arugula; Biosynthesis; Brassicaceae; Chain elongation; Condensing enzyme; Eruca sativa; Glucosinolate; Methionine; Methylthioalkylmalate synthase

Indexed keywords

2 (2' METHYLTHIOETHYL)MALATE; 2 (OMEGA METHYLTHIOALKYL)MALATE SYNTHASE; 2 ISOPROPYLMALATE SYNTHASE; 4 METHYLTHIO 2 OXOBUTANOIC ACID; ACETYL COENZYME A; BUTYRIC ACID; CITRATE SYNTHASE; DIHOMOMETHIONINE; GLUCOSINOLATE; LEUCINE; MALATE SYNTHASE; MALIC ACID DERIVATIVE; METHIONINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHROMATOGRAPHY; CITRIC ACID CYCLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ISOLATION; ENZYME SUBSTRATE; ERUCA SATIVA; MEDICINAL PLANT; POLYMERIZATION; PURIFICATION;

2-ISOPROPYLMALATE SYNTHASE; ACETYL COENZYME A; BRASSICACEAE; CATIONS, DIVALENT; CHLOROPLASTS; GLUCOSINOLATES; HYDROLYSIS; MALATE SYNTHASE; MALONYL COENZYME A; MASS SPECTROMETRY; METHIONINE; SPECIES SPECIFICITY; SUBSTRATE SPECIFICITY; TRITIUM;

BRASSICACEAE; ERUCA SATIVA;

EID: 1942419908     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2004.02.021     Document Type: Article

References (29)

1. Bryan J.K. Synthesis of the aspartate family and branched-chain amino acids. Miflin B.J. The Biochemistry of Plants Vol. 5, Amino Acids and Derivatives. 1980;403-452 Academic Press, New York
2. Chapple C.C.S., Decicco C., Ellis B.E. Biosynthesis of 2-(2′-methylthio)ethylmalate in Brassica carinata. Phytochemistry. 27:1988;3461-3463
3. 14C and related compounds to horseradish Canadian Journal of Biochemistry. 42:1964;1033-1040
4. Dawson G.W., Hick A.J., Bennett R.N., Donald A., Pickett J.A., Wallsgrove R.M. Synthesis of glucosinolate precursors and investigations into the biosynthesis of phenylalkyl- and methylthioalkylglucosinolates. Journal of Biological Chemistry. 268:1993;27154-27159
5. 1-Kettenverlängerung von Aminosäuren: Untersuchungen über α-Benzylmalat-Synthase und α-Benzylmalat-Isomerase. Ph.D. Thesis, Phillips-Universität Marburg. 1977;Lahn, Germany
6. 3 mustard oil glucoside Canadian Journal of Biochemistry. 52:1974;916-921
7. Fahey J.W., Zalcmann A.T., Talalay P. The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry. 56:2001;5-51
8. Graser G., Oldham N.J., Brown P.D., Temp U., Gershenzon J. The biosynthesis of benzoic acid glucosinolate esters in Arabidopsis thaliana. Phytochemistry. 57:2001;23-32
9. Graser G., Schneider B., Oldham N.J., Gershenzon J. The methionine chain elongation pathway in the biosynthesis of glucosinolates in Eruca sativa (Brassicaceae). Archives of Biochemistry and Biophysics. 378:2000;411-419
10. Gray G.S., Bhattacharjee J.K. Biosynthesis of lysine in Saccharomyces cereviseae. properties and spectrophotometric determination of homocitrate synthase EC-41.3.21 activity Canadian Journal of Microbiology. 22:1976;1664-1667
11. Hagelstein P., Schultz G. Leucine synthesis in spinach chloroplasts. partial characterization of 2-isopropylmalate synthase Biological Chemistry Hoppe-Seyler. 374:1993;1105-1108
12. Halkier B.A. Glucosinolates. Ikan R. Naturally Occurring Glycosides: Chemistry, Distribution and Biological Properties. 1999;193-223 John Wiley and Sons, Chichester
13. Hecht S.S. Inhibition of carcinogenesis by isothiocyanates. Drug Metabolism Reviews. 32:2000;395-411
14. Kohlaw G., Leary T.R., Umbarger H.E. α-Isopropylmalate synthase from Salmonella typhimurium. purification and properties Journal of Biological Chemistry. 244:1969;2218-2225
15. Kroumova A.B., Wagner G.J. Different elongation pathways in the biosynthesis of acyl groups of trichome exudate sugar esters from various solanaceous plants. Planta. 216:2003;1013-1021
16. Kroymann J., Textor S., Tokuhisa J., Falk K.L., Bartram S., Gershenzon J., Mitchell-Olds T. A gene controlling variation in Arabidopsis glucosinolate composition is part of the methionine chain elongation pathway. Plant Physiology. 127:2001;1077-1088
17. 15N]-2-amino-6-(methylthio)caproic acid in progoitrin biosynthesis. Biochemistry. 9:1970;2068-2071
18. Li G., Riaz A., Goyal S., Abel S., Quiros C.F. Inheritance of three major genes involved in the synthesis of aliphatic glucosinolates in Brassica oleracea. Journal of the American Society of Horticultural Science. 126:2001;427-431
19. Löffelhardt W., Kindl H. The biosynthesis of 4-methylsulfinyl-3- butenylglucosinolate (glucoraphenin) in Matthiola species. evidence for homomethionine and 2-amino-6-methylthiocaproic acid as intermediates Zeitschrift für Naturforschung. 30c:1975;233-239
20. Masurekar P.S., Demain A.L. Insensitivity of homocitrate synthase in extracts of Penicillium chyrosogenum to feedback inhibition by lysine. Applied Microbiology. 28:1974;265-270
21. Morse M.A., Eklind K.I., Amin S.G., Hecht S.S., Chung F.-L. Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates. Carcinogenesis. 10:1989;1757-1759
22. Rask L., Andreasson E., Ekbom B., Eriksson S., Pontoppidan B., Meijer J. Myrosinase. gene family evolution and herbivore defense in Brassicaceae Plant Molecular Biology. 42:2000;93-113
23. Reichelt M., Brown P.D., Schneider B., Oldham N.J., Stauber E., Tokuhisa J., Kliebenstein D.J., Mitchell-Olds T., Gershenzon J. Benzoic acid glucosinolate esters and other glucosinolates from Arabidopsis thaliana. Phytochemistry. 59:2002;663-671
24. Ulm E.J., Boehme R., Kohlaw G. α-Isopropylmalate synthase from yeast. purification, kinetic studies, and effect of ligands on stability Journal of Bacteriology. 110:1972;1118-1126
25. Underhill E.W. Biosynthesis of mustard oil glucosides. 3-benzylmalic acid, a precursor of 2-amino-4-phenylbutyric acid and of gluconasturtiin Canadian Journal of Biochemistry. 46:1968;401-405
26. Webster R.E., Gross S.R. The α-isopropylmalate synthetase of Neurospora I. The kinetics and end product control of α-isopropylmalate synthetase function. Biochemistry. 4:1965;2309-2318
27. Wiegel J., Schlegel H.G. α-Isopropylmalate synthase from Alcaligenes eutrophus H 16 I. Purification and general properties. Archives of Microbiology. 112:1977;239-246
28. Wittstock U., Kliebenstein D.J., Lambrix V., Reichelt M., Gershenzon J. Glucosinolate hydrolysis and its impact on generalist and specialist insect herbivores. Romeo J.T. Integrative Phytochemistry: From Ethnobotany to Molecular Ecology, Recent Advances in Phytochemistry, Vol. 37. 2003;101-125 Elsevier, London
29. Zheng L., White R.H., Dean D.R. Purification of the Azotobacter vinelandii NifV-encoded homocitrate synthase. Journal of Bacteriology. 179:1997;5963-5966