Vier neue Metabolite von Giberella zeae: 5‐Formyl‐zearalenon, 7′‐Dehydrozearalenon, 8′‐Hydroxy‐ und 8′‐epi‐Hydroxy‐zearalenon

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Abstract
From cultures of Gibberella zeae ergosterol, zearalenone (1) and hitherto unknown minor metabolites, i.e.. 5‐formyl‐zearalenone (6), 7′‐dehydrozearalenone (8), 8′‐hydroxyzearalenone (9) and 8′‐epi‐hydroxyzearalenone (11) were isolated. The production of zearalenone and its congeners proved to be very strongly dependent on the conditions of culture.5‐Formyl‐zearalenone (6) as well as 3‐formylzearalenone (4) were synthesized from zearalenone (1) and characterized by the di‐O‐methyl derivatives 7 and 5 respectively. The structure of 7′‐ dehydrozearalenone (8) was deduced from spectral data. The di‐O‐methyl derivatives 10 and 12 respectively of the two corresponding epimeric 8′‐hydroxy derivatives 9 and 11 yielded the same β‐diketone 13. The keto‐enol equilibrium of 13 was studied.

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