Metabolism of 1,8-Cineole by a Species: Ring Cleavage Reactions Free

Abstract

sp. (strain C1) was isolated by elective culture with 1,8-cineole as sole carbon source. 6--Hydroxycineole and 6-oxocineole accumulated transiently during the latter part of the exponential growth phase and, together with 1,8-cineole, were oxidized rapidly by 1,8-cineole-grown cells. Although a putative 1,8-cineole monooxygenase was not detected in cell-free systems an induced 6--hydroxycineole dehydrogenase and an induced NADPH-linked 6-oxocineole oxygenase were readily demonstrated. The lactone 5,5-dimethyl-4-(3′-oxobutyl)-4,5-dihydrofuran-2(3H)-one was isolated from oxygenation reactions with 6-oxocineole as substrate. This was not the immediate product of oxygenation but resulted from non-enzymic lactonization of the ring cleavage intermediate 3-(1-hydroxy-1-methylethyl)-6-oxoheptanoic acid during extraction procedures. 2,5-Diketocamphane 1,2-monooxygenase purified from (+)-camphor-grown ATCC 17453 was also able to utilize 6-oxocineole as a substrate with formation of the same isolated product. The established oxygen-insertion specificity of this enzyme coupled with an unequivocal absence of esterase activity allowed the nature of the oxygen insertion into 6-oxocineole by the enzyme from C1 to be inferred and a reaction sequence for cleavage of both rings of 1,8-cineole to be proposed. It provides an explanation for the reported isolation of ()-5,5-dimethyl-4-(3′-oxobutyl)-4,5-dihydrofuran-2(3H)-one from culture media of grown with 1,8-cineole.

Loading

Article metrics loading...

/content/journal/micro/10.1099/00221287-135-7-1957
1989-07-01
2024-03-29
Loading full text...

Full text loading...

/deliver/fulltext/micro/135/7/mic-135-7-1957.html?itemId=/content/journal/micro/10.1099/00221287-135-7-1957&mimeType=html&fmt=ahah

References

  1. Bernhardt F.-H., Erdin N., Staudinger H., Ullrich V. 1973; Interaction of substrates with a purified 4-methoxybenzoate monooxygenase system (O-demethylating) from Pseudomonas putida.. European Journal of Biochemistry 35:601–611
    [Google Scholar]
  2. Best D.J., Floyd N.C., Magalhaes A., Burfield A., Rhodes P.M. 1987; Initial enzymatic steps in the degradation of alpha-pinene by Pseudomonas fluorescens NCIMB 11671.. Biocatalysis 1:147–159
    [Google Scholar]
  3. Cain R.B. 1961; The metabolism of protocatechuic acid by a Vibrio.. Biochemical Journal 79:298–312
    [Google Scholar]
  4. Carman R.M., Macrae I.C., Perkins M.V. 1986; The oxidation of 1,8-cineole by Pseudomonas flava.. Australian Journal of Chemistry 39:1739–1746
    [Google Scholar]
  5. Chapman P.J., Meerman G., Gunsalus I.C., Srinivasan R., Rinehart K.L. 1966; A new acyclic metabolite in camphor oxidation.. Journal of the American Chemical Society 88:618–619
    [Google Scholar]
  6. Davey J.F., Trudgill P.W. 1977; The metabolism of fraws-cyclohexan-l,2-diol by an Acinetobacter species.. European Journal of Biochemistry 74:115–127
    [Google Scholar]
  7. Dhavalikar R.S., Bhattacharyya P.K. 1966; Microbial transformations of terpenes. VII. Fermentation of limonene by a soil Pseudomonad.. Indian Journal of Biochemistry 3:144–157
    [Google Scholar]
  8. Dhavalikar R.S., Rangachari P.N., Bhattacharyya P.K. 1966; Microbial transformations of terpenes. IX. Pathways of degradation of limonene by a soil Pseudomonad.. Indian Journal of Biochemistry 3:158–164
    [Google Scholar]
  9. Donoghue N.A., Norris D.B., Trudgill P.W. 1976; The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB9871.. European Journal of Biochemistry 63:175–192
    [Google Scholar]
  10. Friedemann T.E., Haugen G.E. 1943; Pyruvic acid. II. The determination of keto acids in blood and urine.. Journal of Biological Chemistry 147:415–442
    [Google Scholar]
  11. Gornall A.G., Bardawill C.J., David M.M. 1949; Determination of serum proteins by means of the biuret reaction.. Journal of Biological Chemistry 111:751–766
    [Google Scholar]
  12. Goodfellow M. 1986; Genus Rhodococcus Zopf 1891, 28AL.. In Bergey’s Manual of Systematic Bacteriology 2 pp. 1472–1481 Sneath P. H. A., Mair N. S., Sharpe M. E. Edited by Baltimore: Williams & Wilkins;
    [Google Scholar]
  13. Griffiths E. T., Bociek S. M., Harries P. C., Jeffcoat R., Sissons D. J., Trudgill P. W. 1987a; Bacterial metabolism of a-pinene: pathway from a-pinene oxide to acyclic metabolites in Nocardia sp. strain PI8.3.. Journal of Bacteriology 169:4972–4979
    [Google Scholar]
  14. Griffiths E. T., Harries P. C., Jeffcoat R., Trudgill P. W. 1987b; Purification and properties of a-pinene oxide lyase from Nocardia sp. strain PI 8.3.. Journal of Bacteriology 169:4980–4983
    [Google Scholar]
  15. Katagiri M., Ganguli B.N., Gunsalus I.C. 1968; A soluble cytochrome P450 functional in methylene hydroxylation.. Journal of Biological Chemistry 243:3543–3546
    [Google Scholar]
  16. Macrae I.C., Alberts V., Carman R.M., Shaw I.M. 1979; Products of 1,8-cineole oxidation by a Pseudomonad.. Australian Journal of Chemistry 32:917–922
    [Google Scholar]
  17. Nishimura H., Noma Y., Mizutani J. 1982; Eucalyptus as biomass. Novel compounds from microbial conversion of 1,8-cineole.. Agricultural and Biological Chemistry 46:2601–2604
    [Google Scholar]
  18. Ougham H.J., Taylor D.G., Trudgill P.W. 1983; Camphor revisited: involvement of a unique monooxygenase in the metabolism of 2-oxo-Δ3-4,5,5- trimethylcyclopentenylacetic acid by Pseudomonas putida.. Journal of Bacteriology 153:140–152
    [Google Scholar]
  19. Rosazza J.P.N., Steffens J.J., Sariaslani F.S., Goswami A., Beale J.M., Reeg S., Chapman R. 1987; Microbial hydroxylation of 1,4-cineole.. Applied and Environmental Microbiology 53:2482–2486
    [Google Scholar]
  20. Rosenberger R.F., Elsden S.R. 1960; The yields of Streptococcus faecalis grown in continuous culture.. Journal of General Microbiology 22:726–739
    [Google Scholar]
  21. Shukla O.P., Moholay M.N., Bhattacharyya P.K. 1968; Microbial transformations of terpenes. X. Fermentation of α- and β-pinenes in a soil pseudomonad (PL-strain).. Indian Journal of Biochemistry 5:79–91
    [Google Scholar]
  22. Taylor D.G., Trudgill P.W., Cripps R.E., Harris P.R. 1980; The microbial metabolism of acetone.. Journal of General Microbiology 118:159–170
    [Google Scholar]
  23. Taylor D.G., Trudgill P.W. 1986; Camphor revisited: studies of 2,5-diketocamphane 1,2-monooxygenase from Pseudomonas putida ATCC 17453.. Journal of Bacteriology 165:489–497
    [Google Scholar]
  24. Taylor D.G., Trudgill P.W. 1988; The bacterial metabolism of 18-cineole (eucalyptol).. In Microbial Metabolism and the Carbon Cycle p. 510 Hagedorn S. R., Hanson R. S., Kunz D. A. Edited by Chur: Harwood;
    [Google Scholar]
  25. Trudgill P.W. 1984; Degradation of the alicyclic ring.. In Microbial Degradation of Organic Compounds pp. 131–180 Gibson D. T. Edited by New York: Marcel Dekker;
    [Google Scholar]
  26. Trudgill P.W. 1986; Terpenoid metabolism by Pseudomonas.. In The Bacteria 10 pp. 483–528 Sokatch J. R. Edited by New York: Academic Press;
    [Google Scholar]
  27. Wallach O. 1895; Zur Constitutionsbestimmung des Terpineols.. Chemische Berichte 28:1755–1777
    [Google Scholar]
http://instance.metastore.ingenta.com/content/journal/micro/10.1099/00221287-135-7-1957
Loading
/content/journal/micro/10.1099/00221287-135-7-1957
Loading

Data & Media loading...

Most cited Most Cited RSS feed