Antimycins A₁₀—A₁₆, Seven New Antimycin Antibiotics Produced by Streptomyces spp. SPA‐10191 and SPA‐8893.

Abstract

The new antimycin antibiotics (I) are isolated along with several known analogues. They exhibit antifungal activity against Candida utilis. Compounds (Ia) and (Ib) form a 85:15 mixture which is inseparable by HPLC. -(HOSOTANI, N.; KUMAGAI, K.; NAKAGAWA, H.; SHIMATANI, T.; SAJI, I.; J. Antibiot. 58 (2005) 7, 460-467; Explor. Res. Group, Res. Div., Sumitomo Pharm. Co., Ltd., Takarazuka, Hyogo 665, Japan; Eng.) -M. Bohle 02-205

Potent Inhibitors of Pro-Inflammatory Cytokine Production Produced by a Marine-Derived Bacterium

“…As antimycin structures differ from each other by the length and branching of their alkyl and acyl chains, their structures were determined through interpretation of HRMS and by comparison to reported 1 H NMR data. [9][10][11] Relative Configurations of the Splenocins. The relative configurations of the splenocins were assigned by interpretation of proton NMR coupling constants and by analysis of NOESY NMR data (Table 4 and Figure 3, respectively).…”

“…This fundamental structure, together with the cyclic bis-lactone core, is also seen in molecules of the antimycin class. [9][10][11] The splenocins are further characterized and differentiated from the antimycins by the presence of benzyl groups positioned at C-7 (1-3, 10) and benzoyl groups at C-8 (4-8) of the bis-lactone ring. Compound 9 contains aromatic functionalities at both the C-7 and C-8 positions.…”

Endophytic Streptomyces sp. AC35, a producer of bioactive isoflavone aglycones and antimycins

“…According to the MS data, we also predicted the occurrence of antimycin A10 or 14 (m/z 562. [29]. The material of purified antimycins is not available for biological and biochemical studies as the isolation of each pure component from a cultured broth is possible only with intensive effort [14,30].…”

Biosynthesis of Antimycins with a Reconstituted 3-Formamidosalicylate Pharmacophore in Escherichia coli

“…Antimycins are a family of depsipeptides consisting of a nine-membered dilactone ring substituted with one alkyl (C-7), one acyloxy (C-8), two methyl moieties (C-4 and C-9), and an amide linkage (C-3) connecting to a 3-formamidosalicylic acid (Figure ). They are produced by various Streptomyces species, and over the past few years, a growing number of natural and modified antimycin-type compounds varying in the alkyl and acyl chains have been reported. − Additionally, several related antimycin-type depsipeptides with 12-, 15-, and 18-membered macrolactone rings were also recently isolated and characterized (Figure ). , Notably, all of these compounds possess a common 3-formamidosalicylate unit, which previous studies have demonstrated to be essential for the antifungal, insecticidal, nematocidal, and piscicidal properties of antimycins. − , While these bioactivities arise from the ability of antimycins to inhibit cytochrome c oxidoreductase in the mitochondrial electron transport chain, other work has also shown antimycin-type compounds to be promising candidates for treating a variety of diseases, including asthma, cancer, Alzheimer’s disease, and Parkinson’s disease. ,,− Understanding the enzymatic machinery and engineering efficient systems for antimycin biosynthesis can therefore expand the production of antimycin analogues with improved pharmaceutical properties.…”

“…9,10 Notably, all of these compounds possess a common 3-formamidosalicylate unit, which previous studies have demonstrated to be essential for the antifungal, insecticidal, nematocidal, and piscicidal properties of antimycins. [1][2][3]11 While these bioactivities arise from the ability of antimycins to inhibit cytochrome c oxidoreductase in the mitochondrial electron transport chain, 12 other work has also shown antimycin-type compounds to be promising candidates for treating a variety of diseases, including asthma, cancer, Alzheimer's disease, and Parkinson's disease. 9,10,13−15 Understanding the enzymatic machinery and engineering efficient systems for antimycin biosynthesis can therefore expand the production of antimycin analogues with improved pharmaceutical properties.…”