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


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.


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



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

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Supplementary material 1 (DOCX 67 kb)
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Supplementary material 2 (DOCX 133 kb)
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Supplementary material 3 (DOCX 51 kb)


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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

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