Advertisement

Applied Microbiology and Biotechnology

, Volume 62, Issue 4, pp 331–336 | Cite as

Cleavage of β,β-carotene to flavor compounds by fungi

  • H. Zorn
  • S. Langhoff
  • M. Scheibner
  • R. G. Berger
Original Paper

Abstract

More than 50 filamentous fungi and yeasts, known for de novo synthesis or biotransformation of mono-, sesqui-, tri-, or tetraterpenes, were screened for their ability to cleave β,β-carotene to flavor compounds. Ten strains discolored a β,β-carotene-containing growth agar, indicating efficient degradation of β,β-carotene. Dihydroactinidiolide was formed as the sole conversion product of β,β-carotene in submerged cultures of Ganoderma applanatum, Hypomyces odoratus, Kuehneromyces mutabilis, and Trametes suaveolens. When mycelium-free culture supernatants from five species were applied for the conversions, nearly complete degradation of β,β-carotene was observed after 12 h. Carotenoid-derived volatile products were detected in the media of Ischnoderma benzoinum, Marasmius scorodonius, and Trametes versicolor. β-Ionone proved to be the main metabolite in each case, whereas β-cyclocitral, dihydroactinidiolide, and 2-hydroxy-2,6,6-trimethylcyclohexanone were formed in minor quantities. Using a photometric bleaching test, the β,β-carotene cleaving enzyme activities of M. scorodonius were partially characterized.

Keywords

Carotenoid Submerged Culture Extracellular Enzyme Activity Carotenoid Degradation Ganoderma Applanatum 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Notes

Acknowledgements

Support of the work by the Deutsche Forschungsgemeinschaft (ZO 122/1–1) is gratefully acknowledged. All experiments comply with the current laws of the Federal Republic of Germany.

References

  1. Beatriz M, Gloria A, Grulke EA, Gray J I (1993) Effect of type of oxidation on β-carotene loss and volatile products formation in model systems. Food Chem 46:401–406Google Scholar
  2. Ben Aziz A, Grossman S, Ascarelli I, Budowski P (1971) Carotene-bleaching activities of lipoxygenase and heme proteins as studied by a direct spectrophotometric method. Phytochemistry 10:1445–1452CrossRefGoogle Scholar
  3. Bosser A, Belin J M (1994) Synthesis of β-ionone in an aldehyd/xanthin oxidase/β-carotene system involving free radical formation. Biotechnol Prog 10:129–133Google Scholar
  4. Bosser A, Paplorey E, Belin J-M (1995) A simple way to (+/-)-dihydroactinidiolide from β-Ionone related to the enzymic co-oxidation of β-carotene in aqueous solution. Biotechnol Prog 11:689–692Google Scholar
  5. Britton G, Liaaen-Jensen S, Pfander H (1999) Carotenoids, vol 1A. Isolation and analysis. Birkenhäuser Verlag, BaselGoogle Scholar
  6. Grivel F, Larroche C (2001) Phase transfer and biocatalyst behaviour during biotransformation of β-ionone in a two-phase liquid system by immobilised Aspergillus niger. Biochem Eng J 7(1):27–34CrossRefPubMedGoogle Scholar
  7. Grivel F, Larroche C, Gros JB (1999) Determination of the reaction yield during biotransformation of the volatile and chemically unstable compound β-ionone by Aspergillus niger. Biotechnol Progr 15(4):697–705CrossRefGoogle Scholar
  8. Handelman G J, van Kuijk GM, Chatterjee A, Krinsky NI (1991) Characterisation of products formed during the autoxidation of β-carotene. Free Radical Biol Med 10:427–437CrossRefGoogle Scholar
  9. Hohler A (1986) Untersuchung der Bildung und Eigenschaften von flüchtigen Nor-Carotinoiden. PhD thesis, University of Munich, GermanyGoogle Scholar
  10. Janssens L, De Pooter H L, Schamp NM, Vandamme EJ (1992) Production of flavours by microorganisms. Process Biochem 27:195–215CrossRefGoogle Scholar
  11. Jüttner F, Höflacher B (1985) Evidence of β-carotene 7,8 (7′,8′) oxygenase (β-cyclocitral, crocetindial generating) in Microcystis. Arch Microbiol 141(3):337–343Google Scholar
  12. Kiefer C, Hessel S, Lampert J, Vogt K, Lederer MO, Breithaupt DE, von Lintig J (2001) Identification and characterisation of a mammalian enzyme catalysing the asymmetric oxidative cleavage of provitamin A. J Biol Chem 276(17):14110–14114PubMedGoogle Scholar
  13. Krammer GE, Werkhoff P, Sommer H, Schmidt CO, Gatfield I, Bertram H-J (2002) Carotenoid degradation products in paprika powder. In: Winterhalter P, Rouseff RL (eds) Carotenoid-derived aroma compounds. ACS symposium series, vol 802. ACS, Washington DC, pp 206–219Google Scholar
  14. Mester T, Field JA (1998) Characterization of a novel manganese peroxidase-lignin peroxidase hybrid isozyme produced by Bjerkandera species strain BOS55 in the absence of manganese. J Biol Chem 273(25):15412–15417PubMedGoogle Scholar
  15. Mohamed N, Hashim R, Rahman NA, Zain SM (2001) An insight to the cleavage of β-carotene to vitamin A: a molecular mechanics study. J Mol Struct 538:245–252CrossRefGoogle Scholar
  16. Prasad MM, Singh HNP (1995) Biodegradation of chemical constituents in silk cocoons by some storage fungi. Sci Lett 18(9, 10):163–164Google Scholar
  17. Qin X, Zeevaart JAD (1999) The 9-cis epoxycarotenoid cleavage reaction is the key regulatory step of abscisic acid biosynthesis in water-stressed bean. Proc Natl Acad Sci USA 96:15354–15361CrossRefPubMedGoogle Scholar
  18. Ruiz-Duenas FJ, Martinez MJ, Martinez AT (1999) Molecular characterization of a novel peroxidase isolated from the ligninolytic fungus Pleurotus eryngii. Mol Microbiol 31:223–235PubMedGoogle Scholar
  19. Sanchez-Contreras A, Jimenez M, Sanchez S (2000) Bioconversion of lutein to products with aroma. Appl Microbiol Biotechnol 54:528–534CrossRefPubMedGoogle Scholar
  20. Schreier P (1995) Aromaforschung aktuell. Naturwissenschaften 82:21–27CrossRefPubMedGoogle Scholar
  21. Schwartz SH, Cai Tan B, Gage DA, Zeevaart JAD, McCarty DR (1997) Specific oxidative cleavage of carotenoids by VP14 of maize. Science 276:1872–1874PubMedGoogle Scholar
  22. Schwartz SH, Qin X, Zeevaart JAD (2001) Characterization of a novel carotenoid cleavage dioxygenase from plants. J Biol Chem 276:25208–25211CrossRefPubMedGoogle Scholar
  23. Thompson AJ, Jackson AC, Parker RA, Morpeth DR, Burbidge A, Taylor IB (2000) Abscisic acid biosynthesis in tomato: Regulation of zeaxanthin epoxidase and 9-cis-epoxycarotinoid dioxygenase mRNAs by light/dark cycles, water stress and abscisic acid. Plant Mol Biol 42:833–845CrossRefPubMedGoogle Scholar
  24. Von Lintig J, Vogt K (2000) Filling the gap in vitamin A research. J Biol Chem 275:11915–11920CrossRefPubMedGoogle Scholar
  25. Wache Y, Bosser-De Ratuld A, Belin J-M (2002) Production of aroma compounds by enzymatic cooxodation of carotenoids. In: Winterhalter P, Rouseff R (eds) ACS symposium series, vol 802. ACS, Washington DC, pp 102–113Google Scholar
  26. Winterhalter P (1996) Carotenoid-derived aroma compounds: biogenetic and biotechnological aspects. In: Takeoka GR, Teranishi R, Williams PJ, Kobayashi A (eds) Biotechnology for improved foods and flavours. ACS symposium series, vol 637. ACS, Washington DC, pp 295–308Google Scholar
  27. Winterhalter P, Rouseff R (2002) Carotenoid-derived aroma compounds: An introduction. In: Winterhalter P, Rouseff R (eds) Carotenoid-derived aroma compounds. ACS symposium series, vol 802. ACS, Washington DC, pp 1–17Google Scholar
  28. Wu Z, Robinson DS (1999) Co-oxidation of β-carotene catalyzed by soybean and recombinant pea lipoxygenase. J Agric Food Chem 47:4899–4906CrossRefPubMedGoogle Scholar
  29. Wyss A, Wirtz G, Woggon W-D, Brugger R, Wyss M, Friedlein A, Bachmann H, Hunziker W (2000) Cloning and expression of β,β-Carotene 15,15´-dioxygenase. Biochem Biophys Res Com 271:334–336CrossRefPubMedGoogle Scholar
  30. Yan W, Jang GF, Haesseler F, Esumi N, Chang J, Kerrigan M, Campochiaro M, Campochiaro P, Palczewski K, Zack DJ (2001) Cloning and characterisation of a human β,β-carotene-15,15′-dioxygenase that is highly expressed in the retinal pigment epithelium. Genomics 72:193–202CrossRefPubMedGoogle Scholar

Copyright information

© Springer-Verlag 2003

Authors and Affiliations

  • H. Zorn
    • 1
  • S. Langhoff
    • 1
  • M. Scheibner
    • 1
  • R. G. Berger
    • 1
  1. 1.Zentrum Angewandte ChemieInstitut für Lebensmittelchemie der Universität HannoverHannoverGermany

Personalised recommendations