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Transformations of acetates of citronellol, geraniol, and linalool by Aspergillus niger: regiospecific hydroxylation of citronellol by a cell-free system

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Summary

Incubation of acetates of geraniol, citronellol and linalool with Aspergillus niger resulted in their hydrolysis to corresponding alcohols which were further hydroxylated to their respective 8-hydroxy derivatives. In the case of linalyl acetate, besides linalool and 8-hydroxylinalool, small amounts of geraniol and α-terpineol were also formed. Microsomes (105 000xg sediment) prepared from induced cells of A. niger were found to convert (1-3H)citronellol to 8-hydroxy citronellol in the presence of NADPH and O2. The pH optimum for the hydroxylase was found to be 7.6.

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References

  • Abraham WR, Hoffman HMR, Kieslich K, Reng G, Stumpf B (1985) Microbial transformations of some monoterpenoids and sesquiterpenoids. In: Enzymes in organic synthesis. Ciba foundation symposium 111, Pitman Press, London, pp 146–160

    Google Scholar 

  • Aller RT van, Nes WR (1968) The phosphorylation of geraniol in germinating peas. Phytochemistry 7:85–88

    Google Scholar 

  • Cantwell SC, Lau EP, Walt DS, Ray Fall R (1978) Biodegradation of acyclic isoprenoids by Pseudomonas species. J Bacteriol 135:324–333

    Google Scholar 

  • Cerniglia CE, Gibson DT (1978) Metabolism of naphthalene by cell extracts of Cunninghamella elegans. Arch Biochem Biophys 18:121–127

    Google Scholar 

  • Chadha A, Madyastha KM (1982) ω-Hydroxylation of acyclic monoterpene alcohols by rat lung microsomes. Biochem Biophys Res Commun 108:1271–1277

    Google Scholar 

  • Escher (1972) Ph. D. Dissertation No. 4887, Eidgenössische Technische Hochschule, Zürich, Switzerland

  • Jayanthi CR, Madyastha P, Madyastha KM (1982) Microsomal 11α-hydroxylation of progesterone in Aspergillus ochraceus: Part I: Characterisation of the hydroxylase system. Biochem Biophys Res Commun 106:1262–1268

    Google Scholar 

  • Krasnobajew V (1984) Microbial transformations of terpenoids. In: Rehm HJ, Reed G (Eds) Biotechnology, vol 6a, Biotransformations. Verlag Chemie, Weinheim

    Google Scholar 

  • Kurita N, Miyoji M, Kurane R, Takahara Y (1981) Antifungal activity of components of essential oils. Agr Biol Chem 45(4):945–952

    Google Scholar 

  • Lowry OH, Rosebrough NJ, Farr AL, Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265–275

    Google Scholar 

  • Madyastha KM, Meehan TD, Coscia CJ (1976) Characterisation of a cytochrome P-450 dependent monoterpene hydroxylase from the higher plant Vinca rosea. Biochemistry 15:1097–1102

    Google Scholar 

  • Madyastha KM, Renganathan V (1983) Biodegradation of acetates of geraniol, nerol and citronellol by P. incognita: Isolation and identication of metabolites. Indian J Biochem Biophys 20:136–140

    Google Scholar 

  • Prema BR, Bhattacharyya PK (1962) Microbial transformations of terpenes II: Transformations of α-pinene. Appl Microbiol 10:524–528

    Google Scholar 

  • Renganathan V, Madyastha KM (1983) Linalyl acetate is metabolised by P. incognita with the acetoxy group intact. Appl Environ Microbiol 45:6–15

    Google Scholar 

  • Renganathan V, Madyastha KM (1984) Metabolism of structurally modified acyclic monoterpenes by P. incognita. Can J Microbiol 30:637–641

    Google Scholar 

  • Seubert W (1960) Degradation of isoprenoid compounds by mocroorganisms. I. Isolation and characterisation of an isoprenoid degrading bacterium, P. citronellolis. J Bacteriol 79:426–434

    Google Scholar 

  • Stumpf B, Abraham WR, Kieslich K (1982) Verfahren zur Herstellung von (+)-α-terpineol durch mikrobiologische Umwandlung von Limonen. German Pat Appl 3243090

  • Stumpf B, Abraham WR, Kieslich K (1984) Herstellung von vicinalen Diolen mit 1,2-Dihydroxy-2-methyl-propyl-Strukturen. German Pat Appl 3418054

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Madyastha, K.M., Murthy, N.S.R.K. Transformations of acetates of citronellol, geraniol, and linalool by Aspergillus niger: regiospecific hydroxylation of citronellol by a cell-free system. Appl Microbiol Biotechnol 28, 324–329 (1988). https://doi.org/10.1007/BF00268189

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