Advertisement

Biotechnology Letters

, Volume 34, Issue 7, pp 1351–1356 | Cite as

Biotransformation of isonitrosoacetophenone (2-keto-2-phenyl-acetaldoxime) in tobacco cell suspensions

  • Ntakadzeni E. Madala
  • P. A. Steenkamp
  • L. A. Piater
  • I. A. DuberyEmail author
Original Research Paper

Abstract

Nicotiana tabacum cell suspensions, 2 g wet wt/ml, rapidly took up 1 mM isonitrosoacetophenone (INAP), a plant-derived stress metabolite with anti-oxidative and anti-fungal properties, producing 4′-hexopyranosyloxy-3′-methoxyisonitrosoacetophenone in 54 % yield over 18 h. Unconverted INAP was at 33 μM. UPLC–MS/MS analyses with MassFragment software were used for metabolite identification. INAP had been hydroxylated at its meta- and para-positions as well as undergoing subsequent methoxylation and glycosylation. INAP is thus recognized by the enzymatic machinery of the phenylpropanoid pathway and is converted to a molecule with a substitution pattern similar to ferulic acid.

Keywords

Biotransformation Isonitrosoacetophenone 2-keto-2-phenyl-acetaldoxime Metabolism Nicotiana tabacum Solanaceae Xenobiotics 

Notes

Acknowledgments

This work was supported in part by the South African National Research Foundation (NRF) and the University of Johannesburg. The NRF RISP/NEP program is thanked for partial funding of the Synapt HD-MS system. M. George and F. Tugizimana are thanked for helpful discussions and support.

Supplementary material

10529_2012_909_MOESM1_ESM.docx (67 kb)
Supplementary material 1 (DOCX 67 kb)
10529_2012_909_MOESM2_ESM.docx (134 kb)
Supplementary material 2 (DOCX 133 kb)
10529_2012_909_MOESM3_ESM.docx (51 kb)
Supplementary material 3 (DOCX 51 kb)

References

  1. Allwood JW, Goodacre R (2010) Introduction to liquid chromatography–mass spectrometry instrumentation applied in plant metabolomic analyses. Phytochem Anal 21:33–47PubMedCrossRefGoogle Scholar
  2. Chiron H, Drouet A, Claudot A-C et al (2000) Molecular cloning and functional expression of a stress-induced multifunctional O-methyltransferase with pinosylvin methyltransferase activity from Scots pine (Pinus sylvestris L.). Plant Mol Biol 44:733–745PubMedCrossRefGoogle Scholar
  3. Dubery IA, Louw AE, Van Heerden FR (1999) Synthesis and evaluation of 4-(3-methyl-2 butenoxy) isonitrosoacetophenone, a radiation-induced stress metabolite in Citrus. Phytochemistry 50:983–989PubMedCrossRefGoogle Scholar
  4. Frick S, Kutchan TM (1999) Molecular cloning and functional expression of O-methyltransferases common to isoquinoline alkaloid and phenylpropanoid biosynthesis. Plant J 17:329–339PubMedCrossRefGoogle Scholar
  5. Kikuzaki H, Hisamoto M, Hirose K et al (2002) Antioxidant properties of ferulic acid and its related compounds. J Agric Food Chem 50:2161–2168PubMedCrossRefGoogle Scholar
  6. Lewinsohn E, Gijzen M (2009) Phytochemical diversity: the sounds of silent metabolism. Plant Sci 176:161–169CrossRefGoogle Scholar
  7. Mahadevan S (1973) Role of oximes in nitrogen metabolism in plants. Annu Rev Plant Physiol 24:69–88CrossRefGoogle Scholar
  8. Maury S, Geoffroy P, Legrand M (1999) Tobacco O-methyltransferases involved in phenylpropanoid metabolism. The different caffeoyl-coenzyme A/5-hydroxyferuloyl- coenzyme A 3/5-O-methyltransferase and caffeic acid/5-hydroxyferulic acid 3/5-O- methyltransferase classes have distinct substrate specificities and expression patterns. Plant Physiol 121:215–223PubMedCrossRefGoogle Scholar
  9. Meyermans H, Morreel K, Lapierre C et al (2000) Modifications in lignin and accumulation of phenolic glucosides in Poplar xylem upon down-regulation of caffeoyl-coenzyme A O-methyltransferase, an enzyme involved in lignin biosynthesis. J Biol Chem 275:36899–36909PubMedCrossRefGoogle Scholar
  10. Møller BL (2010) Dynamic metabolons. Science 330:1328–1329PubMedCrossRefGoogle Scholar
  11. Omiecinski CJ, Heuvel JPV, Perdew GH, Peters JM (2011) Xenobiotic metabolism, disposition, and regulation by receptors: from biochemical phenomenon to predictors of major toxicities. Toxicol Sci 120:49–75CrossRefGoogle Scholar
  12. Pollier J, Mosesab T, Goossens A (2011) Combinatorial biosynthesis in plants: a review on its potential and future exploitation. Nat Prod Rep 28:1897–1916PubMedCrossRefGoogle Scholar
  13. Sanabria NM, Dubery IA (2006) Differential display profiling of the Nicotiana response to LPS reveals elements of plant basal resistance. Biochem Biophys Res Commun 344:1001–1007PubMedCrossRefGoogle Scholar
  14. Schalk M, Pierrel MA, Zimmerlin A, Batard Y, Durst F, Werck-Reichhart D (1997) Xenobiotics: substrates and inhibitors of the plant cytochrome P450. Environ Sci Pollut Res 4:229–234CrossRefGoogle Scholar
  15. Schoch GA, Attias R, Le Ret M, Werck-Reichhart D (2003) Key substrate recognition residues in the active site of a plant cytochrome P450, CYP73A1—homology model guided site-directed mutagenesis. Eur J Biochem 270:3684–3695PubMedCrossRefGoogle Scholar
  16. Schwab W (2003) Metabolome diversity: too few genes, too many metabolites? Phytochemistry 62:837–847PubMedCrossRefGoogle Scholar
  17. Towill LE, Mazur P (1975) Studies on the reduction of 2,3,5-triphenyltetrazolium chloride as a viability assay for plant tissue cultures. Can J Bot 53:1097–1102CrossRefGoogle Scholar
  18. Vogt T (2010) Phenylpropanoid biosynthesis. Mol Plant 3:2–20PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Ntakadzeni E. Madala
    • 1
  • P. A. Steenkamp
    • 2
  • L. A. Piater
    • 1
  • I. A. Dubery
    • 1
    Email author
  1. 1.Department of BiochemistryUniversity of JohannesburgJohannesburgSouth Africa
  2. 2.Discovery Chemistry Research Group, BioSciences UnitCSIRPretoriaSouth Africa

Personalised recommendations