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Melithiazols A–N: New Antifungal β‐Methoxyacrylates from Myxobacteria

1999; Wiley; Volume: 1999; Issue: 10 Linguagem: Inglês

10.1002/(sici)1099-0690(199910)1999

1434-193X

Bettina Böhlendorf, Martina Herrmann, Hans‐Jürgen Hecht, Florenz Sasse, Edgar Forche, Brigitte Kunze, Hans Reichenbach, Gerhard Höfle,

Fungal Plant Pathogen Control

From cultures of Melittangium lichenicola, Archangium gephyra and Myxococcus stipitatus, thirteen new β-methoxyacrylate (MOA) fungicides related to myxothiazols (1) have been isolated. Melithiazols A (2a), D (2b), K (2c), and L (2d) are characterized by a thiazoline–thiazole system, whereas melithiazols B (3a), E (3b), F (3c), G (3d), H (3e), I (3f), M (3g), and N (3h) are bis(thiazoles). Melithiazol C (4), as the first representative of this class of compounds, contains only one thiazole ring. The structures were established on the basis of spectroscopic data, and confirmed in the case of melithiazol E (3b), including its relative configuration, by an X-ray structure analysis. The absolute configuration of melithiazols A (2a) and B (3a) was determined by degradation and CD spectroscopy. Antifungal and cytotoxic activities, inhibition of NADH oxidation, and lipophilicities of melithiazols 2–4, myxothiazols 1, and strobilurin-type compounds are compared.