Heptaene macrolide antibiotic

Therapeutic Function Topical antifungal Chemical Name Heptaene macrolide antibiotic Common Name —... 

Sowinski and coworkers40 reported a structure of vacidin A (63), an aromatic hep-taene macrolide antibiotic. The constitution of vacidin A, a representative of the aromatic heptaene macrolide antibiotics, was established on the basis of 13C and H- H double quantum filtered correlated spectroscopy, rotating frame nuclear Overhauser effect spectroscopy, 7-resolved 11 as well as H-13C correlation NMR spectra. The geometry of the polyene chromophore was determined as 22E, 24E, 26E, 28Z, 30Z, 32E, 34E. 

Candicidin production by Streptomyces griseus was inhibited by inorganic phosphate, which suppressed the biosynthesis of p-aminobenzoate, the starter unit for the synthesis of this 38-membered heptaene macrolide antibiotic [95]. P-aminobenzoic acid synthase (PABA synthase) catalyses the conversion of chorismic acid to PABA, which is a precursor to candicidin. 

Candicidin D is a heptaene macrolide antibiotic produced by S. griseus IMRU 3570 containing an aromatic moiety. It was first described by Lechevalier et al. in 1953 and named antibiotic C135, although it was renamed candicidin because of its strong... 

The comparative chemotherapeutic activities of several heptaene macrolide antibiotics, including amphotericin B, have been examined, and some biological properties of polyene macrolide ester salts have been reported. ... 

Amphotericin B is the most important clinically and best defined chemically of the macrolide heptaene antibiotics. A fermentation product of the soil actinomycetes Streptomyces nodosus, amphotericin B binds selectively to ergosterol in the cell membrane of susceptible fungi, inducing changes in permeability that can produce lethal cell injury [50]. 

Cybulska B, Mazeiski J, Borowski E, Gaty-Bobo CM. Haemolytic activity of aromatic heptaenes. A group of polyene macrolide antifungal antibiotics. Biochem Pharmacol 1984 1 4 M6. 

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