Letter | Published:

New Dehydroxylation Reaction observed in the Microbiological Degradation Pathway of Cholic Acid

Naturevolume 214pages520521 (1967) | Download Citation

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Abstract

IN continuing our examination of microbiological degradation of bile acid1–3, we found that when cholic acid (I) was incubated with the same method as described in a previous paper4, a new metabolite of cholic acid by Corynebacterium (Arthrobacter) simplex, 4α-(2-carboxyethyl)-5-oxo-7αβ,γdimethyl-3aα-hexahydroindane-1β-butyric hexahydroindane-1β-butyric acid (IX), was accumulated in the incubation mixture in parallel with a disappearance of a large number of the cholic acid metabolites, 7α,12α-dihydroxy-3-oxocholanic (II), 7α,12α -dihydroxy-3-oxo-Δ4-cholenic (III), 12α-hydroxy-3-oxo-Δ4,6-choladienic (IV), 12α-hydroxy-3-oxo-Δ4-cholenic (V) and 12α-hydroxy-3-oxo-Δ1,4-choladienic (VI) acids reported previously4, from the incubation mixture.

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References

  1. 1

    Hayakawa, S., Fujii, T., Saburi, Y., and Eguchi, T., Nature, 179, 537 (1957).

  2. 2

    Hayakawa, S., Saburi, Y., Tamaki, K., and Hoshijima, H., Nature, 181, 906 (1958).

  3. 3

    Hayakawa, S., and Kurokawa, K., Nature, 199, 490 (1963).

  4. 4

    Hayakawa, S., and Samuelsson, B., J. Biol. Chem., 239, 94 (1964).

  5. 5

    Sih, C. J., Lee, S. S., Tsong, Y. Y., and Wang, K. C., J. Amer. Chem. Soc., 87, 1385 (1965).

  6. 6

    Sih, C. J., Wang, K. C., Gibson, D. T., and Whitlock, jun., H. W., J. Amer. Chem. Soc., 87, 1386 (1965).

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  1. Shionogi Research Laboratory, Shionogi and Co., Ltd., Fukushima-ku, Osaka, Japan

    • SHOHEI HAYAKAWA
    • , YOSHIKO KANEMATSU
    •  & TAKASHI FUJIWARA

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https://doi.org/10.1038/214520b0

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