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Microbial transformations of isocupressic acid

S J Lin1, J P Rosazza

  • 1Division of Medicinal and Natural Products Chemistry, and Center for Biocatalysis and Bioprocessing, College of Pharmacy, University of Iowa, Iowa City, Iowa 52242, USA.

Journal of Natural Products
|July 25, 1998
PubMed
Summary

Microbial biotransformations of isocupressic acid yielded novel oxygenated metabolites. Different microorganisms produced unique compounds through specific enzymatic reactions, expanding the library of labdane diterpene derivatives.

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Area of Science:

  • Microbial Biotechnology
  • Natural Product Chemistry
  • Organic Chemistry

Background:

  • Isocupressic acid is a labdane diterpene found in various plant species.
  • Microbial transformations offer a sustainable route to synthesize complex natural products.
  • Exploring microbial metabolism of diterpenes can uncover novel chemical structures and reactions.

Purpose of the Study:

  • To investigate the microbial metabolism of isocupressic acid using diverse microorganisms.
  • To isolate and characterize the oxygenated metabolites produced.
  • To identify new nor-labdane derivatives and hydroxylated compounds.

Main Methods:

  • Incubation of isocupressic acid with Nocardia aurantia, Cunninghamella elegans, and Mucor mucedo.
  • Isolation of metabolites using chromatographic techniques.

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  • Structure elucidation of isolated compounds via Mass Spectrometry (MS) and Nuclear Magnetic Resonance (NMR) spectroscopy.

    • Main Results:

    • Nocardia aurantia produced a new nor-labdane metabolite (2) via cleavage of the 13,14-double bond.
    • Cunninghamella elegans yielded 7beta-hydroxyisocupressic acid (3) and a triol derivative (4).
    • Mucor mucedo generated 2alpha-hydroxyisocupressic acid (5) and a diol derivative (6).

    Conclusions:

    • Microbial biotransformation is effective for generating diverse oxygenated metabolites of isocupressic acid.
    • Specific microorganisms exhibit distinct enzymatic capabilities for modifying labdane diterpenes.
    • The study identified novel metabolites, contributing to the understanding of diterpene biosynthesis and microbial catabolism.