Benzaldehyde is a precursor of phenylpropylamino alkaloids as revealed by targeted metabolic profiling and comparative biochemical analyses in Ephedra spp.

Phytochemistry

Volumn 81, Issue , 2012, Pages 71-79

  Krizevski, Raz ^a,b   Bar, Einat ^a   Shalit, O R ^c   Levy, Asaf ^a   Hagel, Jillian M ^d   Kilpatrick, Korey ^e,f   Marsolais, Frédéric ^e,f   Facchini, Peter J ^d   Ben Shabat, Shimon ^b   Sitrit, Yaron ^b   Lewinsohn, Efraim ^a  

^a VOLCANI CENTER   (Israel)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

^c UNIVERSITY OF HAIFA   (Israel)

^d UNIVERSITY OF CALGARY   (Canada)

^e UNIVERSITY OF WESTERN ONTARIO   (Canada)

^f AGRICULTURE AND AGRI FOOD CANADA   (Canada)

Author keywords

(S) Cathinone reductase, (1R,2S) norephedrine N methyltransferase; Benzaldehyde carboxyligase; Ephedra foeminea; Ephedra sinica Stapf; Ephedrine alkaloids; Metabolic pathway elucidation

Indexed keywords

1 HYDROXY 1 PHENYL 2 PROPANONE; 1-HYDROXY-1-PHENYL-2-PROPANONE; ACETONE; ALCOHOL DEHYDROGENASE; ALKALOID; BENZALDEHYDE; BENZALDEHYDE DERIVATIVE; DRUG DERIVATIVE; EPHEDRINE; PROPYLAMINE; PYRUVIC ACID; VEGETABLE PROTEIN;

ARTICLE; COMPARATIVE STUDY; ENZYME ACTIVATION; ENZYMOLOGY; EPHEDRA; METABOLISM; METABOLOME; PLANT STEM; SOLID PHASE MICROEXTRACTION; SOLUBILITY; SPECIES DIFFERENCE;

ACETONE; ALCOHOL OXIDOREDUCTASES; ALKALOIDS; BENZALDEHYDES; ENZYME ACTIVATION; EPHEDRA; EPHEDRINE; METABOLOME; PLANT PROTEINS; PLANT STEMS; PROPYLAMINES; PYRUVIC ACID; SOLID PHASE MICROEXTRACTION; SOLUBILITY; SPECIES SPECIFICITY;

EPHEDRA; EPHEDRA CAMPYLOPODA; EPHEDRA FOEMINEA; EPHEDRA SINICA; EPHEDRACEAE;

EID: 84864744875     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.05.018     Document Type: Article

References (31)

1. K. Arai, T. Kamata, H. Uchikoba, and S. Fu Some Lactobacillus L-lactate dehydrogenases exhibit comparable catalytic activities for pyruvate and oxaloacetate J. Bacteriol. 183 2001 397 400
2. M.M. Bradford A dye binding assay for protein Anal. Biochem. 72 1976 248 254
3. J. Bruneton Pharmacognosy Phytochemistry Medicinal Plants 1995 Intercept Ltd. Hampshire pp. 711-715
4. S. Caveney, D.A. Charlet, H. Freitag, M. Maier-Stolte, and A.N. Starratt New observations on the secondary chemistry of world Ephedra (Ephedraceae) Am. J. Bot. 88 2001 1199 1208
5. D.M. Chipman, R.G. Duggleby, and K. Tittmann Mechanisms of acetohydroxyacid synthases Curr. Opin. Chem. Biol. 9 2005 475 481
6. G. Coruzzi, and R. Last Amino acids B.B. Buchanan, W. Gruissem, R.L. Jones, Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologists 2000 Rockville USA 358 410
7. R. Croteau, T.M. Kutchan, and N.G. Lewis Natural products (secondary metabolites) B.B. Buchanan, W. Gruissem, R.L. Jones, Biochemistry and Molecular Biology of Plants. American Society of Plant Physiologists 2000 Rockville USA 1250 1318
8. R.G. Duggleby, J.A. McCourt, and L.W. Guddat Structure and mechanism of inhibition of plant acetohydroxyacid synthase Plant Physiol. Biochem. 46 2008 309 324
9. S. Engel, M. Vyazmensky, S. Geresh, Z. Barak, and D.M. Chipman Acetohydroxyacid synthase: A new enzyme for chiral synthesis of R-phenylacetylcarbinol Biotechnol. Bioeng. 83 2003 833 840
10. S. Engel, M. Vyazmensky, D. Berkovich, Z. Barak, and D.M. Chipman Substrate range of acetohydroxy acid synthase I from Escherichia coli in the stereoselective synthesis of α-hydroxy ketones Biotechnol. Bioeng. 88 2004 825 831
11. G. Grue-Sorensen, and I.D. Spenser Biosynthesis of ephedrine J. Am. Chem. Soc. 110 1988 3714 3715
12. G. Grue-Sorensen, and I.D. Spenser Biosynthetic route to the Ephedra alkaloids Am. Chem. Soc. 116 1994 6195 6200
13. J.M. Hagel, R. Krizevski, K. Kilpatrick, Y. Sitrit, F. Marsolais, E. Lewinsohn, and P.J. Facchini Expressed sequence tag analysis of khat (Catha edulis) provides a putative molecular biochemical basis for the accumulation of phenylpropylamino alkaloids Genet. Mol. Biol. 34 2011 640 646
14. Hagel, J.M., Marsolais, F., Lewinsohn, E., Facchini, P.J., in press. Biosynthesis of amphetamine analogues in plants. Trends Plant. Sci.
15. S. Jitrapakdee, and J.C. Wallace Structure, function and regulation of pyruvate carboxylase Biochem. J. 340 1999 1 16
16. R. Krizevski, N. Dudai, E. Bar, and E. Lewinsohn Developmental patterns of ephedrine alkaloids accumulation in khat (Catha edulis, Forsk., Celastraceae) J. Ethnopharmacol. 114 2007 432 438
17. R. Krizevski, N. Dudai, E. Bar, I. Dessow, U. Ravid, and E. Lewinsohn Quantitative stereoisomeric determination of phenylpropylamino alkaloids in khat (Catha edulis Forsk.) Isr. J. Plant Sci. 56 2008 207 213
18. R. Krizevski, E. Bar, O. Shalit, Y. Sitrit, S. Ben-Shabat, and E. Lewinsohn Composition and stereochemistry of ephedrine alkaloids accumulation in Ephedra sinica Stapf Phytochemistry 71 2010 895 903
19. E. Leete Biogenesis of d-norpseudoephedrine in Catha edulis Chem. Ind. 1958 1088 1089
20. E. Lewinsohn, and M. Gijzen Phytochemical diversity: The sounds of silent metabolism Plant Sci. 176 2009 161 169
21. D. Meyer, L. Walter, G. Kolter, M. Pohl, M. Müller, and K. Tittmann Conversion of pyruvate decarboxylase into an enantioselective carboligase with biosynthetic potential J. Am. Chem. Soc. 133 2011 3609 3616
22. J.A. McCourt, S.S. Pang, J. King-Scott, L.W. Guddat, and R.G. Duggleby Herbicide-binding sites revealed in the structure of plant acetohydroxyacid synthase Proc. Natl. Acad. Sci. USA. 103 2006 81569 81573
23. N.A. O'Dowd, P.G. McCauley, G. Wilson, J.A.N. Parnell, T.A.K. Kavanaugh, and D.J. McConnell Ephedra species: In vitro culture, micropropagation and the production of ephedrine and other alkaloids Y.P.S. Bajaj, Biotechnology in Agriculture and Forestry 41. Medicinal and Aromatic Plants X 1998 Springer-Verlag Berlin, Germany 154 193
24. T. Okada, M. Mikage, and S. Sekita Molecular characterization of the phenylalanine ammonia lyase from Ephedra sinica Biol. Pharm. Bull. 31 2008 2194 2199
25. E. Pichersky, and E. Lewinsohn Convergent evolution in plant specialized metabolism Annu. Rev. Plant Biol. 62 2011 1 18
26. M. Pohl, P. Siegert, K. Mesch, H. Bruhn, and J. Grötzinger Active site mutants of pyruvate decarboxylase from Zymomonas mobilis, a site-directed mutagenesis study of L112, I472, I476, E473 and N482 Eur. J. Biochem. 257 1998 538 546
27. B. Rosche, M. Breuer, B. Hauer, and P.L. Rogers Screening of yeasts for cell-free production of (R)-phenylacetylcarbinol Biotechnol. Lett. 25 2003 841 845
28. R.B. Rothman, N. Vu, J.S. Partilla, B.L. Roth, S.J. Hufeisen, B.A. Compton-Toth, J. Birkes, R. Young, and R.A. Glennon In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates J. Pharmacol. Exp. Ther. 307 2003 138 145
29. A. Shrestha, S. Dhamwichukorn, and E. Jenwitheesuk Modeling of pyruvate decarboxylases from ethanol producing bacteria Bioinformation 4 2010 378 384
30. E. Stanislav, M. Vyazmensky, S. Geresh, Z. Barak, and D.M. Chipman Acetohydroxyacid synthase: A new enzyme for chiral synthesis of R-phenylacetylcarbinol Biotechnol. Bioeng. 83 2003 833 840
31. M.R. Tellez, I.A. Khan, B.T. Schaneberg, S.L. Crockett, A.M. Rimando, and M. Kobaisy Steam distillation-solid-phase microextraction for the detection of Ephedra sinica in herbal preparations J. Chromatogr. A 1025 2004 51 56