Structures and Properties of Naturally Occurring Polyether Antibiotics

Rutkowski, Jacek; Brzeziński, Bogumił

doi:10.1155/2013/162513

Cited by 104 publications

(109 citation statements)

References 115 publications

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“…The ability of polyether ionophores to control drug-resistant bacteria and parasitic infections is well known, but these compounds also show a broad spectrum of bioactivities, including antifungal, antiviral, antitumor, herbicidal, and anti-inflammatory activities (58,59). In this study, a relatively high number of polyether-producing actinomycetes were isolated, notably the acidophilic streptomycetes (Streptomyces sp.…”

Section: Discussionmentioning

confidence: 97%

Red Soils Harbor Diverse Culturable Actinomycetes That Are Promising Sources of Novel Secondary Metabolites

Guo

Ning

et al. 2015

Appl Environ Microbiol

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Red soils, which are widely distributed in tropical and subtropical regions of southern China, are characterized by low organic carbon, high content of iron oxides, and acidity and, hence, are likely to be ideal habitats for acidophilic actinomycetes. However, the diversity and biosynthetic potential of actinomycetes in such habitats are underexplored. Here, a total of 600 actinomycete strains were isolated from red soils collected in Jiangxi Province in southeast China. 16S rRNA gene sequence analysis revealed a high diversity of the isolates, which were distributed into 26 genera, 10 families, and 7 orders within the class Actinobacteria; these taxa contained at least 49 phylotypes that are likely to represent new species within 15 genera. The isolates showed good physiological potentials for biosynthesis and biocontrol. Chemical screening of 107 semirandomly selected isolates spanning 20 genera revealed the presence of at least 193 secondary metabolites from 52 isolates, of which 125 compounds from 39 isolates of 12 genera were putatively novel. Macrolides, polyethers, diketopiperazines, and siderophores accounted for most of the known compounds. The structures of six novel compounds were elucidated, two of which had a unique skeleton and represented characteristic secondary metabolites of a putative novel Streptomyces phylotype. These results demonstrate that red soils are rich reservoirs for diverse culturable actinomycetes, notably members of the families Streptomycetaceae, Pseudonocardiaceae, and Streptosporangiaceae, with the capacity to synthesize novel bioactive compounds. While high-throughput sequencing methods expand our understanding of species diversity in microbial communities and reveal the presence of many new groups that were previously undetected in cultivation studies, the availability of pure cultures is still essential in order to discover new or useful bioactive compounds from microorganisms. As the most prolific secondary metabolite producers, actinomycetes account for approximately 41% of the bioactive microbial metabolites that have been discovered (1). In recent years, with the emergence of antibiotic-resistant microbial pathogens and rediscovery of known bioactive compounds, special habitats in the ocean (2, 3), sponges (4), plants (5, 6), and insects (7) have been found to be potentially important in the search and discovery of bioactive compound-producing strains. Nevertheless, soil is still the predominant source of secondary metabolite-producing actinomycetes. Unexplored and underexplored soil habitats have been found to be a rich source of actinomycetes that produce novel bioactive metabolites (8-10). Acidic soils in China, mostly red soils, are one such habitat.Red soils are generated by abundant rainfall and high temperature and are widespread in tropical and subtropical regions of southern China, covering about 1.13 million km 2 (11). These soils have been subjected to intensive weathering, and mineral nutrients (including Ca, Mg, P, and K) in the soil are mostly eluted, form...

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Section: Discussionmentioning

confidence: 97%

Red Soils Harbor Diverse Culturable Actinomycetes That Are Promising Sources of Novel Secondary Metabolites

Guo

Ning

et al. 2015

Appl Environ Microbiol

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“…73 Our study began with an exploration to determine a suitable position for the double bond in the R 2 group of the cobalt complex that would avoid undesirable intramolecular Nicholas reactions or elimination reactions. After some experimentation, we found that complex 92 was the most appropriate for carrying out the intermo- Additionally, by using this strategy, we developed a formal synthesis of the enantiomer of the natural product (+)-laurencin (1). 73 This compound is one of the most representative members of the group of lauroxanes, and was first isolated from the extracts of the red algae L. glandulifera by Irie and co-workers in 1965.…”

Section: Scheme 30 Retrosynthetic Analysis Of Cyclic Ethers Based On mentioning

confidence: 99%

Strategies for the Synthesis of Cyclic Ethers of Marine Natural Products

Martı́n

Padrón

Martı́n

2013

Synlett

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“…Zum Vergleich verkapseln elektrogene Ionophore,s ow ie das zyklische Peptid Va linomycin, das Metallion (Kalium im Falle von Va linomycin) als positiv geladenen Komplex und befçrdern das Ion durch die Membran entlang seines Konzentrationsgradienten. Wegen ihrer faszinierenden Eigenschaften [7,8] und potenziellen therapeutischen Anwendungen sind Carboxylpolyether-Ionophore seit vier Jahrzehnten Ziele chemischer Synthesen gewesen, beginnend mit der ersten Totalsynthese von Lasalocid A( 1) von Kishi und Mitarbeitern im Jahr 1978. Außerdem besitzen CPIs auch antibakterielle Aktivität, primärg egen Gram-positive Spezies,u nd zahlreiche Berichte beschreiben ihre Wirkung gegen potenziell medikamentenresistente Bakterienstämme.…”

Section: Introductionunclassified

Chemische Synthesen und chemische Biologie von Carboxylpolyether‐Ionophoren: Aktuelle Entwicklungen

Liu¹,

Lin²,

Jacobsen³

et al. 2019

Angewandte Chemie

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Ein zentrales Ziel der chemischen Biologie ist die Entwicklung von molekularen Sonden, die grundlegende Untersuchungen zellulärer Systeme ermöglichen. In der Hierarchie bioaktiver Moleküle nehmen die sogenannten Ionophore eine unspektakuläre Position ein, wobei typische Charakterisierungen “unspezifisch” und “toxisch” sind. Tatsächlich führt die bloße Möglichkeit, dass ein Kandidatenmolekül “Ionophoraktivität” besitzt, dazu, dass es aus weiteren Studien entfernt wird; Ionophore sind, aus einer chemobiologischen Perspektive betrachtet, “molekulare Gesetzlose”. Im Widerspruch zu diesem insgesamt schlechten Ruf der Ionophore verdankt die synthetische Chemie einige ihrer erstaunlichsten Erfolge den Untersuchungen von Ionophor‐Naturstoffen, insbesondere den Carboxylpolyethern, die für ihre komplizierten molekularen Strukturen bekannt sind. Diese Verbindunge waren jahrzehntelang akademische Spielwiesen, um neue Synthesemethoden zu testen und retrosynthetische Taktiken zu perfektionieren. Hier betrachten wir die aufregendsten jüngsten Fortschritte bei der Synthese von Carboxylpolyether‐Ionophoren (CPI) und diskutieren darüber hinaus das aufkeimende Feld der chemischen Biologie von CPIs.

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Structures and Properties of Naturally Occurring Polyether Antibiotics

Cited by 104 publications

References 115 publications

Red Soils Harbor Diverse Culturable Actinomycetes That Are Promising Sources of Novel Secondary Metabolites

Red Soils Harbor Diverse Culturable Actinomycetes That Are Promising Sources of Novel Secondary Metabolites

Strategies for the Synthesis of Cyclic Ethers of Marine Natural Products

Chemische Synthesen und chemische Biologie von Carboxylpolyether‐Ionophoren: Aktuelle Entwicklungen

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