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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Koh, I. K. and Lee. S. S., Biodegradation mechanism of shogaol byAspergillus niger.Yakhak Hoeji, 27, 29–36 (1983).
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).
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).
Mustafa, T., Srivastava, K. C. and Jensen, K. B., Pharmacology of ginger, Zingiber officinale.J. Frug Dev., 6(1), 25–39 (1993).
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).
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).
Surh, Y. J. and Lee, S. S., Capsaicin, a double-edged sword: Toxicity, metabolism, and chemopreventive potential.Life Sci., 56, 1845–1855 (1995a).
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).
Szallasi, A. and Blumberg, P. M., Mechanisms and therapeutic potential of vanilloids (capsaicxin-like molecules).Adv. in Pharmacol., 24, 123–155 (1993).
Takahashi, H., Hashimoto, T., Noma, Y., and Asakawa, Y., Biotransformation of 6-gingerol and 6-shogaol byAspergillus niger.Phytochemistry, 34, 1497–1500 (1993).
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Lee, S., Lee, W. Biotransformation of dehydroparadols byAspergillus niger . Arch. Pharm. Res. 18, 458–461 (1995). https://doi.org/10.1007/BF02976352
- Metabolic pattern of dehydroparadol
- Aspergillus niger