Biosynthesis of Cladospirone Bisepoxide, A Member of the Spirobisnaphthalene Family

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Abstract

The biosynthesis of cladospirone bisepoxide (<b>1</b>) was investigated by feeding <sup>13</sup>C-labeled acetate to growing cultures of the fungus <i>Sphaeropsidales</i> sp. (strain F-24'707). <sup>13</sup>C NMR spectral analysis demonstrated the polyketide origin of both naphthalene units. The origin of two epoxide oxygens was confirmed as from air by cultivation of the strain in an <sup>18</sup>O<sub>2</sub>-enriched atmosphere. The [<sup>18</sup>O]incorporation pattern into palmarumycin C<sub>12</sub> (<b>11</b>), the putative precursor of <b>1</b> led to the hypothesis that the carbonyl oxygen of <b>1</b> is derived from water by exchange of an oxygen atom. Inhibition of the biosynthesis of <b>1</b> with tricyclazole, an inhibitor of the 1, 8-dihydroxynaphthalene (DHN) melanin biosynthesis, confirmed the connection of both biosynthetic pathways.

Journal

  • The Journal of Antibiotics

    The Journal of Antibiotics 53(2), 153-157, 2000-02-25

    JAPAN ANTIBIOTICS RESEARCH ASSOCIATION

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