1887

Abstract

The disproportionate difficulty in obtaining compelling experimental evidence from C-radio-labelling that the indole moiety of the otherwise isoprenoid penitrem A is biosynthesized by directly from tryptophan has been explored, [-C]Tryptophan added to the broth beneath the mycelial mat of stationary liquid cultures labelled penitrem A with 1·4% incorporation, only threefold more than that determined for [-C]tryptophan or [U-C]tyrosine, incorporation of which could only have been indirect. In contrast, the substituted tryptophan-histidine diketopiperazine roquefortine, biosynthesized concurrently with penitrems by this organism, was labelled with compelling efficiency (23·4% incorporation of [-C]tryptophan). In submerged culture, concurrently biosynthesized an analogous pair of metabolites, 3-hydroxy-3-methylbutenyl paspalinine and lysergic acid α-hydroxyethylamide. This feature enabled experimental demonstratation of [-C]tryptophan incorporation to an extent more consistent with direct contribution of the indole moiety of the indole-diterpenoid paspalinine derivative. The same precursor applied to the sporing surface of stationary cultures also provided stronger evidence for a direct biosynthetic role in the formation of penitrem A. In the absence of competition from any other indolic secondary metabolite, a submerged culture of incorporated 5% of the [-C]tryptophan given during growth into the indole-diterpenoid paxilline. A double-labelling time-course experiment indicated temporal separation of steps in the biosynthesis of roquefortine. The inadequacy of classical precursor techniques for studying biosynthesis of indole-diterpenoids in is discussed. The more homogeneous submerged culture fermentation system is preferred for experimentation.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-135-10-2679
1989-10-01
2022-01-27
Loading full text...

Full text loading...

/deliver/fulltext/micro/135/10/mic-135-10-2679.html?itemId=/content/journal/micro/10.1099/00221287-135-10-2679&mimeType=html&fmt=ahah

References

  1. Acklin W., Weibel F., Arigoni D. 1977; Zur Biosynthese von Paspalin und verwandten Meta-boliten aus Claviceps paspali.. Chimia 31:63
    [Google Scholar]
  2. Barrow K.D., Colley P.W., Tribe D.E. 1979; Biosynthesis of the neurotoxin alkaloid roquefortine.. Journal of the Chemical Society Chemical Communicati ons:225–226
    [Google Scholar]
  3. Cole R.J., Dorner J.W., Lansden J.A., Cox R.H., Pape C., Cunfer B., Nicholoson S.S., Bedell D.M. 1977; Paspalum staggers: isolation and identification of tremorgenic metabolites from sclerotia of C.paspali.. Journal of Agricultural and Food Chemistry 25:1197–1201
    [Google Scholar]
  4. Day J.B. 1981 Tremorgenic mycotoxins and natural staggers syndromes. PhD thesis University of London;
    [Google Scholar]
  5. Gallagher R.T., Finer J., Clardy J., Leutwiler A., Weibel F., Acklin W., Arigoni D. 1980a; Paspalinine, a tremorgenic metabolite of Claviceps paspali Stevens et Hall.. Tetrahedron tetters 21:235–238
    [Google Scholar]
  6. Gallagher R.T., Clardy J., Wilson B.J. 1980b; Afiatoxin, a tremorgenic toxin from Aspergillus flavus.. Tetrahedron tetters 21:239–242
    [Google Scholar]
  7. Gallagher R.T., Hawkes A.D., Steyn P.S., Vleggaar R. 1984; Tremorgenic neurotoxins from perennial ryegrass causing ryegrass staggers of livestock: structure elucidation of lolitrem B.. Journal of the Chemical Society Chemical Communications614–616
    [Google Scholar]
  8. Ibba M., Taylor S.J.C., Weedon C.M., Mantle P.G. 1987; Submerged fermentation of Penicillium paxilli biosynthesizing paxilline, a process inhibited by calcium-induced sporulation.. Journal of General Microbiology 133:3109–3119
    [Google Scholar]
  9. De jesus A.E., Steyn P.S., Van heerden F.R., Vleggaar R., Wessels P.L., Hull W.E. 1981; Structure and biosynthesis of the penitrems A-F, six novel tremorgenic mycotoxins from Penicillium crustosum.. Journal of the Chemical Society Chemical Communications,289–291
    [Google Scholar]
  10. DE Jesus A.E., Gorst-Allman C.P., Steyn P.S., Van heerden F.R., Vleggaar R., Wessels P.L., Hull W.E. 1983; Tremorgenic mycotoxins from Penicillium crustosum: biosynthesis of penitrem A.. Journal of the Chemical Society Perkin Transactions I, 1863–1868
    [Google Scholar]
  11. De jesus A.E., Steyn P.S., Van heerden F.R., Vleggaar R. 1984; Structure elucidation of the janthitrems, novel tremorgenic mycotoxins from Penicillium janthinellum. . Journal of the Chemical Society Perkin Transactions I:697–701
    [Google Scholar]
  12. Laws I. 1985 Biosynthesis and metabolism of indolic fungal metabolites. PhD thesis University of London;
    [Google Scholar]
  13. Mantle P.G., Mortimer P.H., White E.P. 1978; Mycotoxic tremorgens of Claviceps paspali and Penicillium cyclopium: a comparative study of effects on sheep and cattle in relation to natural staggers syndromes.. Research in Veterinary Science 24:49–56
    [Google Scholar]
  14. Mantle P.G., Perera K.P.W.C., Maishman N.J., Mundy G.R. 1983; Biosynthesis of penitrems and roquefortine by Penicillium crustosum.. Applied and Environmental Microbiology 45:1486–1490
    [Google Scholar]
  15. Mantle P.G., Shipston N.F. 1987; Temporal separation of steps in the biosynthesis of verruculo-gen.. Biochemistry International 14:1115–1120
    [Google Scholar]
  16. Martin P.K., Rapoport H., Smith H.W., Wong L.J. 1969; The synthesis of cyclopenin and isocyclopenin.. Journal of Organic Chemistry 34:1359–1363
    [Google Scholar]
  17. Springer J.P., Clardy J., Wells J.M., Cole R.J., Kirksey J.W. 1975; The structure of paxilline, a tremorgenic metabolite of Penicillium paxilli.. Tetrahedron tetters 30:2531–2534
    [Google Scholar]
  18. Steyn P.S., Vleggaar R. 1983; Roquefortine, an intermediate in the biosynthesis of oxaline in cultures of Penicillium oxalicum.. Journal of the Chemical Society Chemical Communications, 560–561
    [Google Scholar]
  19. Weedon C.M., Mantle P.G. 1987; Paxilline biosynthesis by Acremonium loliae; a step towards defining the origin of lolitrem neurotoxins.. Phytochemistry 26:969–971
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-135-10-2679
Loading
/content/journal/micro/10.1099/00221287-135-10-2679
Loading

Data & Media loading...

Most cited this month Most Cited RSS feed

This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error