Cezomycin. -The first calcimycin-class compound occurring in Frankia is revised from structure (Ia) to (Ib). -(KLIKA, K. D.; HAANSUU, J. P.; OVCHARENKO, V. V.; HAAHTELA, K. K.; VUORELA, P. M.; SILLANPAEAE, R.; PIHLAJA, K.; Z. Naturforsch., B: Chem.
An antibiotic produced by the symbiotic actinomycete Frankia strain AiPs1 was isolated from culture broth using optimized thin-layer chromatography and high-performance liquid chromatography (HPLC) methods. The novel compound that was isolated, dubbed frankiamide, displayed antimicrobial activity against all 14 Gram-positive bacterial strains and six pathogenic fungal strains tested. The pathogenic actinomycete Clavibacter michiganensis and the oomycete Phytophthora were especially susceptible. In addition to displaying antimicrobial activity, frankiamide also strongly inhibited 45Ca(2+) fluxes in clonal rat pituitary GH4C1 tumor cells and was comparable to a frequently used calcium antagonist, verapamil hydrochloride. The results of HPLC analysis, supported by both nuclear magnetic resonance and mass spectroscopy studies, showed that frankiamide has a high affinity for Na(+) ions.
A compound (née frankiamide) isolated from Frankia was initially structurally elucidated on the basis of NMR and MS. However, X-ray analysis provided a structure that is in discord with this structure and in light of this the structure has now been revised and the compound renamed as demethyl (C-11) cezomycin.
Frankiamide, a Highly Unusual Macrocycle Containing the Imide and Orthoamide Functionalities from the Symbiotic Actinomycete Frankia.--(KLIKA, KAREL D.; HAANSUU, J. PASI; OVCHARENKO, VLADIMIR V.; HAAHTELA, KIELO K.; VUORELA, PIA M.; PIHLAJA, KALEVI;
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