Skip to main content
Log in

Bioconversion of bi- and tri-cyclic monophenols by alginate-entrapped cells of Mucuna pruriens L. and by the partially purified Mucuna-phenoloxidase

  • Article
  • Published:
Plant Cell, Tissue and Organ Culture Aims and scope Submit manuscript

Abstract

Although alginate-entrapped cells of Mucuna pruriens L. possess a low substrate specificity, only para-substituted monocyclic phenols have been ortho-hydroxylated into catechols so far. In this study, compounds with more complex chemical structures were found to be substrates using entrapped cells of M. pruriens as well as the partially purified Mucuna-phenoloxidase. Thus, 5-, 6- and 7-hydroxylated 2-aminotetralins and a tricyclic compound, 9-hydroxy N-n-propyl hexahydronaphthoxazine, were converted into catechols. After isolation using preparative HPLC, the identity of the products was confirmed by MS. In general, for the entrapped cells and the enzyme preparation identical substrate specificities were found.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Pras N, Wichers HJ, Bruins AP, Malingré ThM (1988) Bioconversion of para-substituted monophenolic compounds into corresponding catechols by alginate-entrapped cells of Mucuna pruriens. Plant Cell Tissue Organ Culture 13: 15–26

    Google Scholar 

  2. Pras N, Hesselink PGM, Guikema WM, Malingré ThM (1989) Further kinetic characterization of alginate-entrapped cells of Mucuna pruriens L. Biotechnol Bioeng 33: 1461–1468

    Google Scholar 

  3. Pras N, Hesselink PGM, Tusscher Jten, Malingré ThM (1989) Kinetic aspects of the bioconversion of L-tyrosine into L-DOPA by cells of Mucuna pruriens L. entrapped in different matrices. Biotechnol Bioeng 34: 214–222

    Google Scholar 

  4. McDermed JD, McKenzie GM, Philips AP (1975) Synthesis and pharmacology of some 2-aminotetralins: Dopamine receptor agonists. J Med Chem 18: 362–367

    Google Scholar 

  5. Horn AS, Kaptein B, Vermue NA, Vries JBde, Mulder TBA (1988) Synthesis and dopaminergic activity of a new oxygen isostere of the 2-aminotetralins: N,N-dipropyl-8-hydroxy-3-chromanamine. Eur J Med Chem 23: 325–328

    Google Scholar 

  6. Dijkstra D, Hazelhoff B, Mulder TBA, Vries JBde, Wijnberg H, Horn AS (1985) Synthesis and pharmacological activity of the hexahydro-4H-naphth[1,2b][1,4]-oxazines: a new series of potent dopamine receptor agonists. Eur J Med Chem 20: 247–250

    Google Scholar 

  7. Huizing HJ, Wichers HJ (1984) Production of L-DOPA by Mucuna pruriens cell suspension cultures through accumulation or by biotransformation of tyrosine. In: Houwink EH, Meer RRvan der (Eds) Innovations in Biotechnology, Progress in Industrial Microbiology 20 (pp 217–228) Elseviers Science Publishers, Amsterdam

    Google Scholar 

  8. Wiehers HJ, Malingré ThM, Huizing HJ (1983) The effect of some environmental factors on the production of L-DOPA by alginate-entrapped cells of Mucuna pruriens. Planta 158: 482–486

    Google Scholar 

  9. Wichers HJ, Peetsma GJ, Malingré ThM, Huizing HJ (1984) Purification and properties of a phenoloxidase derived from suspension cultures of Mucuna pruriens. Planta 162: 334–341

    Google Scholar 

  10. Bruins AP, Pras N (1984) Isolation of 3,4-dihydroxy-phenylacetic acid produced from p-hydroxyphenylacetic acid by immobilized plant cells of Mucuna pruriens L. and its identification by liquid chromatography/mass spectrometry. Anal Chim Acta 163: 91–101

    Google Scholar 

  11. Abul-Hajj YJ, Cisek PL (1986) Regioselective reaction of thiols with catechol estrogens and estrogen-O-quinones. J Steroid Biochem 25: 245–247

    Google Scholar 

  12. Capdevielle P, Maury M (1982) Ortho-hydroxylation sélective des phenols. I. Vers un modèle chimique simple des tyrosinases. Tetrahydron Lett 25: 1573–1576

    Google Scholar 

  13. Bruins AP (1985) Developments in interfacing microbore high-performance liquid chromatography with mass spectrometry (a review) J Chromatogr 323: 99–111

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

This publication is dedicated to the memory of Prof. Alan S. Horn, Ph.D., who deceased at January 2, 1990

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pras, N., Booi, G.E., Dijkstra, D. et al. Bioconversion of bi- and tri-cyclic monophenols by alginate-entrapped cells of Mucuna pruriens L. and by the partially purified Mucuna-phenoloxidase. Plant Cell Tiss Organ Cult 21, 9–15 (1990). https://doi.org/10.1007/BF00034485

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00034485

Key words

Navigation