Macrotetrolide antibiotics produced byStreptomyces globisporus

Jizba, J.; Sedmera, Petr; Zima, Jiřı́; Beran, M.; Blumauerová, M.; Kandybin, N. V.; Samoukina, G. V.

doi:10.1007/bf02884062

Cited by 37 publications

(23 citation statements)

References 19 publications

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“…In agreement with the paper by Shen and Brodbelt, 25 and in contrast to earlier studies, 2 we also did not observe any dehydration of nonactin complexes, presumably reflecting the lack of hydroxyl groups. As shown in Figure 1, all ionophores have a cyclic structure Figure 4 (a) ESI spectrum of macrotetrolide D in peak 9 and its major fragmentation pathway.…”

Section: Nonactins From Streptomyces Griseus By Lc/ms-esi T ř Ezanka supporting

confidence: 93%

“…The macrotetrolide ionophore antibiotic 'polynactin' family is composed of both enantiomers of nonactic acid (1), homononactic acid (2) or bishomononactic acid (3) and are assembled from four acids connected in a head-to-tail manner into a 32-membered macrocycle. The macrotetrolide antibiotics nonactin (4), monactin (5), dinactin (6), trinactin (8), tetranactin (10), and their homologues macrotetrolides B (13), C (11), D (9) and G (7) (Figure 1) were found in different admixtures and proportions in a variety of Streptomyces species.…”

Section: Introductionmentioning

confidence: 99%

“…The macrotetrolide antibiotics nonactin (4), monactin (5), dinactin (6), trinactin (8), tetranactin (10), and their homologues macrotetrolides B (13), C (11), D (9) and G (7) (Figure 1) were found in different admixtures and proportions in a variety of Streptomyces species. 1,2 They display a wide range of biological activities, such as antimicrobial, insecticidal, antifungal and immunosuppressive 3 or antitumor. 4 The biological activities of the macrotetrolides are generally traced to their ionophoric properties, 5 and the potencies of these activities appear to parallel the size of the alkyl substituents of the macrotetrolides: tetranactin is often the most potent member of the family whereas nonactin is generally inactive (this gave rise to its name, that is nonactive).…”

Section: Introductionmentioning

confidence: 99%

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Pilot-plant cultivation of Streptomyces griseus producing homologues of nonactin by precursor-directed biosynthesis and their identification by LC/MS-ESI

et al. 2010

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Precursor-directed biogenetic approach was used to produce a range of nonactin homologues in a 50 l fermentor cultivation of strain Streptomyces griseus 34/249 obtained by UV mutagenesis. The production medium contained sodium propionate, isobutyrate and isovalerate as individual precursors, and 10 g l À1 Diaion HP20 styrene-divinylbenzene resin that maintains suitable precursor concentration by reversibly adsorbing and releasing it. The produced nonactin homologues were separated on two C18 reversed-phase liquid chromatography columns in series and analyzed by MS with ESI source in the positive ion mode. Formation of doubly charged ions was suppressed by an excess of Na + ions throughout the process. The production of the homologues increased up to day 5 and then it leveled off. Cultivations with individual precursors yielded a total of 18 nonactin homologues whose spectrum depended on the precursor used. The total production of the homologues was lowered but their spectrum was shifted to higher-molecular-weight compounds.

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Section: Nonactins From Streptomyces Griseus By Lc/ms-esi T ř Ezanka supporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Pilot-plant cultivation of Streptomyces griseus producing homologues of nonactin by precursor-directed biosynthesis and their identification by LC/MS-ESI

et al. 2010

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“…They are produced by a variety of Streptomyces species (for a review, see Jizba et al [434]). However, with regard to the composition of the macrotetrolide complex, only S. aureus S-3466 (440), which produces a mixture of tetranactin (the most active member of the compound group) with dinactin and trinactin (435,441), has been utilized for commercial purposes (442).…”

Section: Actinobacteria As Sources Of Insecticidesmentioning

confidence: 99%

Taxonomy, Physiology, and Natural Products of Actinobacteria

Barka

Vatsa

Sanchez

et al. 2016

Microbiol Mol Biol Rev

1,534

1,048

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SUMMARYActinobacteriaare Gram-positive bacteria with high G+C DNA content that constitute one of the largest bacterial phyla, and they are ubiquitously distributed in both aquatic and terrestrial ecosystems. ManyActinobacteriahave a mycelial lifestyle and undergo complex morphological differentiation. They also have an extensive secondary metabolism and produce about two-thirds of all naturally derived antibiotics in current clinical use, as well as many anticancer, anthelmintic, and antifungal compounds. Consequently, these bacteria are of major importance for biotechnology, medicine, and agriculture.Actinobacteriaplay diverse roles in their associations with various higher organisms, since their members have adopted different lifestyles, and the phylum includes pathogens (notably, species ofCorynebacterium,Mycobacterium,Nocardia,Propionibacterium, andTropheryma), soil inhabitants (e.g.,MicromonosporaandStreptomycesspecies), plant commensals (e.g.,Frankiaspp.), and gastrointestinal commensals (Bifidobacteriumspp.).Actinobacteriaalso play an important role as symbionts and as pathogens in plant-associated microbial communities. This review presents an update on the biology of this important bacterial phylum.

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“…In our screening studies for new products of pesticidal compounds 1 we isolated soil microorganisms S. globisporus and S. griseus from which we obtained the macrotetrolides-nonactin, monactin, dinactin and trinactin by HPLC on normal phase. 5,6 Free nonactic and homononactic acids were isolated from the strain S. griseus by RP-HPLC. 7 For the identification of metabolites containing nonactic and homonactic acids we employed LC-MS/APCI, as described previously.…”

Section: Introductionmentioning

confidence: 99%