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Planta

, Volume 215, Issue 6, pp 1031–1039 | Cite as

Biosynthesis of podophyllotoxin in Linum album cell cultures

  • Véronique Seidel
  • Jörg Windhövel
  • Graham Eaton
  • Wilhelm A. Alfermann
  • Randolph R. Arroo
  • Manuel Medarde
  • Maike Petersen
  • Jack G. Woolley
Original Article

Abstract.

Cell cultures of Linum album Kotschy ex Boiss. (Linaceae) showing high accumulation of the lignan podophyllotoxin (PTOX) were established. Enzymological studies revealed highest activities of phenylalanine ammonia-lyase, cinnamyl alcohol dehydrogenase, 4-hydroxycinnamate:CoA ligase and cinnamoyl-CoA:NADP oxidoreductase immediately prior to PTOX accumulation. To investigate PTOX biosynthesis, feeding experiments were performed with [2-13C]3′,4′-dimethoxycinnamic acid, [2-13C]3′,4′-methylenedioxycinnamic acid (MDCA), [2-13C]3′,4′,5′-trimethoxycinnamic acid, [2-13C]sinapic acid, [2-13C]- and [2,3-13C2]ferulic acid. Analysis of the metabolites by HPLC coupled to tandem mass spectrometry revealed incorporation of label from ferulic acid into PTOX and deoxypodophyllotoxin (DOP). In addition, MDCA was also unambiguously incorporated intact into PTOX. These observations suggest that in L. album both ferulic acid and methylenedioxy-substituted cinnamic acid can be incorporated into lignans. Furthermore, it appears that, in this species, the hydroxylation of DOP is a rate-limiting point in the pathway leading to PTOX.

Deoxypodophyllotoxin Lignan biosynthesis Linum (cell culture) Phenylpropanoid metabolism Podophyllotoxin 

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Supplementary material

archive1.pdf (69 kb)
Supplemental data (PDF 59 KB)
archive2.pdf (50 kb)
Fig. S1 (PDF 50 KB)

Copyright information

© Springer-Verlag 2002

Authors and Affiliations

  • Véronique Seidel
    • 1
  • Jörg Windhövel
    • 2
  • Graham Eaton
    • 3
  • Wilhelm A. Alfermann
    • 2
  • Randolph R. Arroo
    • 1
  • Manuel Medarde
    • 4
  • Maike Petersen
    • 5
  • Jack G. Woolley
    • 1
  1. 1.Natural Products Research, Faculty of Applied SciencesDe Montfort UniversityLeicesterUK
  2. 2.Institut für Entwicklungs- und Molekularbiologie der PflanzenHeinrich-Heine-UniversitätDüsseldorfGermany
  3. 3.Mass Spectrometry Laboratory, Chemistry DepartmentLeicester UniversityLeicesterUK
  4. 4.Departamento de Química FarmacéuticaFacultad de FarmáciaSalamancaSpain
  5. 5.Institut für Pharmazeutische BiologiePhilipps-Universität MarburgMarburgGermany

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