LL-F42248.ALPHA., a novel chlorinated pyrrole antibiotic.

Abstract

Culture LL-F42248, preliminarily identified as an unusual Streptomyces species, was found to produce the novel antibiotic 1, designated LL-F42248a. This compound, which is related to the coproduced pyrrolomycin C (2)i:) is the first tricyclic member of this family and is the only chiral pyrrolomycin reported to date.2) The culture was grown in a 30-liter tank fer

Nitroaromatic Compounds, from Synthesis to Biodegradation

“…Perhaps the best-known nitroaromatic antibiotic is chloramphenicol (originally named chloromycetin), produced by Streptomyces venezuelae (42,53,178). Other nitro group-containing antibiotics produced by streptomycetes include aureothin, a polyketide from Streptomyces thioluteus (18,77,118); neoaureothin (spectinabilin) and orinocin, polyketides from Streptomyces spectabilis and Streptomyces orinoci (93,122,195), respectively; azomycin, a nitroimidazole from Streptomyces eurocidicus (137); dioxapyrrolomycin, a chloro-nitro compound from Streptomyces fumanus (19,22); thaxtomins, structurally diverse nitro-dipeptides produced by several species of Streptomyces that are pathogens of plant tubers (98,116); rufomycins (Fig. 4), which are cyclic heptapeptides from Streptomyces atratus; and the structurally similar ilamycins, from Streptomyces islandicus (193), which contain a nitro group at the meta position of tyrosine (49,174).…”

Pharmaceutical Potential of Synthetic and Natural Pyrrolomycins

“…The chirality and novel 1,3-dioxane ring may confer additional unique biological properties to this molecule in comparison to other members of the pyrrolomycin class [31]. The antibacterial activities of natural pyrrolomycins are summarized in Table 2.…”

“…Toxicity studies in vivo have been carried out on JCL-ICR mice for dioxapyrrolomycin, which unfortunately was very toxic with an oral LD 50 of 13 mg/kg [31]. The other natural pyrrolomycins were less toxic: pyrrolomycin A and B showed LD 50 values of 21.2 and about 100 mg/kg, respectively, when administered i.p.…”

“…Pyrrolomycins (PM) are polyhalogenated metabolites known for their potent antimicrobial properties [31], isolated from the fermentation broth of Actinosporangium and Streptomyces species [32][33][34][35][36][37]. The antibiotics of this family include pyrrolomycins A, B, C, D, E, G, H, I, J and dioxapyrrolomycin ( Figure 3).…”

“…Pyrrolomycins (PM) are polyhalogenated metabolites known for their potent antimicrobial properties [31], isolated from the fermentation broth of Actinosporangium and Streptomyces species [32][33][34][35][36][37] Important structural features of the pyrrolomycins are: (i) their high halogenation degree, which is usually represented by chlorine substituents; and (ii) in some cases, the presence of a nitro group at the position 3 of the pyrrole ring. The antibacterial activity of these derivatives may be closely related to their halogen content, because it increases as the degree of halogenation [38,39].…”