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Biotransformation of dehydroparadols byAspergillus niger

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Abstract

To prove uniqueness of allylic alcohol formation from α,β-unsaturated ketones by mammal enzymes, a metabolic pattern of dehydroparadols, non-pungent synthetic analogs of shogaol byAspergillus niger was examined. Two biotransformation products of a dehydroparadol, 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-3-one were accumulated in the culture broth ofA. niger. They were characterized as 1-(4-hydroxy-3-methoxyphenyl)-non-1-en-9-ol-3-one and 1-(4-hydroxy-3-methoxyphenyl)-nonan-9-ol-3-one by UV, NMR and mass spectroscopic analyses. Accumulation of allylic alcohol metabolites was not observed.

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References Cited

  • Koh, I. K. and Lee. S. S., Biodegradation mechanism of shogaol byAspergillus niger.Yakhak Hoeji, 27, 29–36 (1983).

    CAS  Google Scholar 

  • Lee, S. S. and Kumar, S., Metabolismin vitro of capsaicin, a pungent principle of red pepper, with rat liver homogenates. In Coon, M.et al. (Eds.),Microsomes, Drug Oxidations, and Chemical Carcinogenesis, Academic Press, 1980, pp. 1009–1012.

  • Lee, S. S. and Kumar, S., Aromatic ring hydroxylation of pungent vanillylalkylketones. In Sato, S. and Kato, R. (Eds.),Microsomes, Drug Oxidations and Drug Toxicology, Japan Sci. Soc. Press and Wiley-Interscience, 1982.

  • Lee, S. S. and You, I. S., Biodegradation mechanisms of capsaicin and its analogs (I): Microbial ω-hydroxyaltion on capsaicin mixture.Kor. Biochem. J., 10, 135–146 (1977).

    CAS  Google Scholar 

  • Locksley, H. D. Rainey, D. K. and Rohan, T. A., Pungent compounds. part I: An improved synthesis of the paradols and an assessment of their pungency.J. Chem. Soc. (Perkin 1.), 23, 3001–3006 (1972).

    Article  Google Scholar 

  • Mustafa, T., Srivastava, K. C. and Jensen, K. B., Pharmacology of ginger, Zingiber officinale.J. Frug Dev., 6(1), 25–39 (1993).

    CAS  Google Scholar 

  • Sih, C. J. and Rosazza, J., Microbial transformations in organic chemistry. In Jones, J. B., Sih, C. J. and Perlman, D. (Eds.),Applications of Biochemical Systems in Organic Chemistry, John Wiley & Son, 1976, pp. 69–106.

  • Surh, Y. J. and Lee, S. S., Enzymatic reduction of 6-shogaol: a novel biotransformation pathway for the α,β-unsaturated ketone system.Biochem. International, 27, 179–187 (1992).

    CAS  Google Scholar 

  • Surh, Y. J. and Lee, S. S., Enzymatic reduction of xenobiotic,-unsaturated ketones: Formation of allyl alcohol metabolites from shogaol and dehydroparadol.Res. Comm. in Chem. Patho. and Pharmacol., 84, 53–61 (1994).

    CAS  Google Scholar 

  • Surh, Y. J. and Lee, S. S., Capsaicin, a double-edged sword: Toxicity, metabolism, and chemopreventive potential.Life Sci., 56, 1845–1855 (1995a).

    Article  PubMed  CAS  Google Scholar 

  • Surh, Y. J. and Lee, S. S., Metabolism of capsaicinoids: Evidence for aliphatic hydroxylation and its pharmacological implications. Life Sci., 56, PL 305–311 (1995b).

    Google Scholar 

  • Szallasi, A. and Blumberg, P. M., Mechanisms and therapeutic potential of vanilloids (capsaicxin-like molecules).Adv. in Pharmacol., 24, 123–155 (1993).

    Article  CAS  Google Scholar 

  • Takahashi, H., Hashimoto, T., Noma, Y., and Asakawa, Y., Biotransformation of 6-gingerol and 6-shogaol byAspergillus niger.Phytochemistry, 34, 1497–1500 (1993).

    Article  CAS  Google Scholar 

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Lee, SS., Lee, WY. Biotransformation of dehydroparadols byAspergillus niger . Arch. Pharm. Res. 18, 458–461 (1995). https://doi.org/10.1007/BF02976352

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