Applied Microbiology and Biotechnology

, Volume 36, Issue 3, pp 410–415 | Cite as

Metabolism of lignin-related compounds by Rhodococcus rhodochrous: bioconversion of anisoin

  • V. Andreoni
  • S. Bernasconi
  • P. Bestetti
  • M. Villa
Environmental Biotechnology
Received:
Accepted:

Summary

The ability of the nocardioform actinomycete Rhodococcus rhodochrous to metabolize selected lignin model compounds was studied. The compounds studied included cinnamic and ferulic acids and dimers possessing intermonomeric linkages that are characteristic of the lignin molecule. R. rhodochrous reduced the carbonyl group of anisoin, a 1,2-diarylethane (β-1) structure to (1R,2R)-1,2-bis(4-methoxyphenyl)ethane-1,2-diol with an enantiomeric excess of .98%. Cleavage of 1,2-diarylethane and β-O-4 structures by this strain could not be detected under our metabolic conditions.

Keywords

Lignin Carbonyl Carbonyl Group Diol Ferulic Acid 
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.
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References

  1. Andreoni V, Baggi G, Barnasconi S, Foglieni C (1990) Biotransformation of alkyl and aryl carbonates. Microbiol degradation. Appl Microbiol Biotechnol 32:414–417Google Scholar
  2. Chen CL, Chang HM, Kirk TK (1982) Aromatic acids produced during degradation of lignin in spruce wood by Phanerochaete chrysosporium. Holzforschung 36:3–8Google Scholar
  3. Dale JA, Dull DL, Mosher HS (1969) α-Methoxy-α-trifluoromethyl phenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J Org Chem 34:2543–2549Google Scholar
  4. Fukuzumi T, Katayama Y (1977) Bacterial degradation of dimer relating to structure of lignin. Mokuzai Gakkaishi 23:214–215Google Scholar
  5. Giroux H, Vidal P, Bouchard J, Lamy F (1988) Degradation of kraft indulin lignin by Streptomyces viridosporus and Streptomyces badius. Appl Environ Microbiol 54:3064–3070Google Scholar
  6. Gold MH, Kuwahara M, Chiu A, Glenn JK (1984) Purification and characterization of an extracellular H2O2 requiring diaryl-propane oxygenase from the white rot basidiomycete Phanerochaete chrysosporium. Arch Biochem Biophys 234:353–359Google Scholar
  7. Goodfellow M (1971) Numerical taxonomy of some nocardioform actinomycetes. J Gen Microbiol 69:33–80Google Scholar
  8. Goodfellow M, Alderson G (1977) The actinomycete genus Rhodococcus: a home for the “rhodochrous” complex. J Gen Microbiol 100:99–112Google Scholar
  9. Jokela J, Pellinen J, Salkinoja-Salonen M (1987) Initial steps in the pathway for the degradation of two tetrameric lignin model compounds. Appl Environ Microbiol 53:2642–2649Google Scholar
  10. Kern HW, Kirk TK (1987) Influence of molecular size and ligninase pretreatment on degradation of lignins by Xanthomonas sp. strains 99. Appl Environ Microbiol 53:2242–2246Google Scholar
  11. Kirk TK, Farrell RL (1987) Enzymatic “combustion”: the microbial degradation of lignin. Annu Rev Microbiol 41:465–505CrossRefPubMedGoogle Scholar
  12. Koshijma T, Watanabe T, Yaku T (1989) Structure and properties of the lignin-carbohydrate complex polymer as an amphipathic substance. ACS Symp Ser 397:11–28Google Scholar
  13. Lai YZ, Sarkanen KV (1971) Isolation and structural studies. In: Sarkanen KV, Ludwig CH (eds) Lignin: occurrence, formation, structure and reactions. Wiley Interscience, New York, pp 165–240Google Scholar
  14. Maniatis T, Fritsch EF, Sambrook J (1982) Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory, Cold Spring Harbor, N.Y.Google Scholar
  15. McKenzie A, Pirie DJC (1936) Stereochemische Untersuchungen in der Anisoin-Gruppe. Chem Ber 69:861–875Google Scholar
  16. Ruttimann C, Seelenfreund D, Vicuna R (1987) Metabolism of low molecular weight lignin-related compounds by Streptomyces viridosporus T7A. Enzyme Microb Technol 9:526–530Google Scholar
  17. Sardi P, Rogers J, Locci R (1979) Membrane transfer techniques for assessing response of developing actinomycetes to adverse environment. Actinomycetes 14:116–117Google Scholar
  18. Scalbert A, Monties B, Lallemand JY, Guittet E, Rolando C (1985) Ether linkage between phenolic acids and lignin fractions from wheat straw. Phytochemistry 24:1359–1362Google Scholar
  19. Still CW, Kahn M, Mitra A (1978) Rapid chromatographic technique for preparative separations with moderate resolution. J Org Chem 43:2923–2925Google Scholar
  20. Sundman V (1964) The ability of α-conidendrin-decomposing Agrobacterium strain to utilize other lignins and lignin-related compounds. J Gen Microbiol 36:185–201Google Scholar
  21. Tien M, Kirk TK (1983) Lignin degrading enzyme from the hymenomycete Phanerochaete chrysosporium. Science 221:661–663Google Scholar
  22. Vicuna R, Gonzales B, Mozuch MD, Kirk TK (1987) Metabolism of lignin model compounds of the arylglycerol-β-arylether type by Pseudomonas acidovorans D3. Appl Environ Microbiol 53:2605–2609Google Scholar
  23. Vicuna R (1988) Bacterial degradation of lignin. Enzyme Microbial Technol 10:646–655Google Scholar
  24. Yamamoto K, Ando H, Shuetake T, Chikamatsu H (1989) Microbial resolution and asymmetric oxidation related to optically active 1,2-bis(methoxyphenyl)ethane-1,2-diol. J Chem Soc Chem Commun 12:754–755Google Scholar

Copyright information

© Springer-Verlag 1991

Authors and Affiliations

  • V. Andreoni
    • 1
  • S. Bernasconi
    • 2
  • P. Bestetti
    • 3
  • M. Villa
    • 1
  1. 1.Dipartimento di Valorizzazione e Protezione delle Risorse AgroforestaliUniversitá di TorinoTorinoItaly
  2. 2.Dipartimento di Chimica Organica ed IndustrialeUniversitá di MilanoMilanoItaly
  3. 3.Dipartimento di Genetica e Biologia dei MicrorganismiUniversitá di MilanoMilanoItaly

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