Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp. and mycolic acid-containing bacterium

Hoshino, Shotaro; Wong, Chin Piow; Ozeki, Masahiro; Zhang, Huiping; Hayashi, Fumiaki; Awakawa, Takayoshi; Asamizu, Shumpei; Onaka, Hiroyasu; Abe, Ikuro

doi:10.1038/s41429-018-0040-4

Cited by 28 publications

(28 citation statements)

References 18 publications

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“…However, a cis-orientation of H-10 and H-11 was determined in 7 [30]. As described by Cao et al [9] and Hoshino et al [34], the small vicinal coupling constant between H-23 and H-25 strongly indicated the relative configuration between H-23 and H-25 to be (23S*, 25S*) in 1 ( 3 J H-23/H-25 1.2 Hz, Table 1). The configuration of C-23 was deduced to be 23S upon the proposed biogenesis from an l-orinithine [7,[15][16][17][18][19][20][21].…”

Section: Genome Mining Of a Ptm Biosynthetic Gene Clustermentioning

confidence: 65%

“…Previously, a trans-orientation of H-10 and H-11 was reported for pactamide A [20], aburatubolactam A (X-ray crystallography structure available [31]), combamide D [32], deOH alteramides, and lysobacterene B [33]. In the recently reported 5/5 type of PTMs umezawamides, the relative orientation of H-10 and H-11 was not determined [34]. However, a cis-orientation of H-10 and H-11 was determined in 7 [30].…”

Section: Genome Mining Of a Ptm Biosynthetic Gene Clustermentioning

confidence: 95%

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Genome Mining of Marine-Derived Streptomyces sp. SCSIO 40010 Leads to Cytotoxic New Polycyclic Tetramate Macrolactams

Liu

Zhang²,

Jin³

et al. 2019

Marine Drugs

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Polycyclic tetramate macrolactams (PTMs) biosynthetic gene cluster are widely distributed in different bacterial types, especially in Streptomyces species. The mining of the genomic data of marine-derived Streptomyces sp. SCSIO 40010 reveals the presence of a putative PTM-encoding biosynthetic gene cluster (ptm′ BGC) that features a genetic organization for potentially producing 5/5/6 type of carbocyclic ring-containing PTMs. A fermentation of Streptomyces sp. SCSIO 40010 led to the isolation and characterization of six new PTMs 1–6. Comprehensive spectroscopic analysis assigned their planar structures and relative configurations, and their absolute configurations were deduced by comparing the experimental electronic circular dichroism (ECD) spectra with the reported spectra of the known PTMs. Intriguingly, compounds 1–6 were determined to have a trans-orientation of H-10/H-11 at the first 5-membered ring, being distinct from the cis-orientation in their known PTM congeners. PTMs 1–5 displayed cytotoxicity against several cancer cell lines, with IC50 values that ranged from 2.47 to 17.68 µM.

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Section: Genome Mining Of a Ptm Biosynthetic Gene Clustermentioning

confidence: 65%

Section: Genome Mining Of a Ptm Biosynthetic Gene Clustermentioning

confidence: 95%

Genome Mining of Marine-Derived Streptomyces sp. SCSIO 40010 Leads to Cytotoxic New Polycyclic Tetramate Macrolactams

Liu

Zhang²,

Jin³

et al. 2019

Marine Drugs

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“…In particular, Microbacterium and Lentzea isolates, as well as other represented genus to lesser extent, such as Streptomyces, Amycolatopsis, and Actinoplanes, may be playing a role in the modulation of communities through competitors' growth inhibition (Tao et al, 2016;Zhao et al, 2018). Nithya et al (2015) reported the isolation of 16 actinobacterial strains from the desert in Arabia Saudi that exhibited antimicrobial potential, and Hoshino et al (2018) described for the first time a new type of macrolactams named as umezawamides as they are synthetized by the genus Umezawaea. Moreover, Wichner et al (2017) reported the isolation of six new metabolites that had never been traced before from microbial sources by a novel strain of Lentzea sp.…”

Section: Discussion the Tabernas Desert Soils Harbor A Wide Bacterialmentioning

confidence: 99%

High Culturable Bacterial Diversity From a European Desert: The Tabernas Desert

et al. 2021

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One of the most diverse ecological niches for microbial bioprospecting is soil, including that of drylands. Drylands are one of the most abundant biomes on Earth, but extreme cases, such as deserts, are considered very rare in Europe. The so-called Tabernas Desert is one of the few examples of a desert area in continental Europe, and although some microbial studies have been performed on this region, a comprehensive strategy to maximize the isolation of environmental bacteria has not been conducted to date. We report here a culturomics approach to study the bacterial diversity of this dryland by using a simple strategy consisting of combining different media, using serial dilutions of the nutrients, and using extended incubation times. With this strategy, we were able to set a large (254 strains) collection of bacteria, the majority of which (93%) were identified through 16S ribosomal RNA (rRNA) gene amplification and sequencing. A significant fraction of the collection consisted of Actinobacteria and Proteobacteria, as well as Firmicutes strains. Among the 254 isolates, 37 different genera were represented, and a high number of possible new taxa were identified (31%), of which, three new Kineococcus species. Moreover, 5 out of the 13 genera represented by one isolate were also possible new species. Specifically, the sequences of 80 isolates held a percentage of identity below the 98.7% threshold considered for potentially new species. These strains belonged to 20 genera. Our results reveal a clear link between medium dilution and isolation of new species, highlight the unexploited bacterial biodiversity of the Tabernas Desert, and evidence the potential of simple strategies to yield surprisingly large numbers of diverse, previously unreported, bacterial strains and species.

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“…This mechanism is different from the one involving signaling via diffusible molecules such as the A-factor and goadsporin, which are produced by actinomycetes species and which can induce SM production within this bacterial group [ 103 ]. The induction of SM production by the addition of mycolic acid-containing bacteria is common among streptomycetes, as evidenced by the fact that 99 out of 112 tested strains displayed altered SM profiles when exposed to mycolic acid-containing bacteria; resulting in the isolation of several novel bioactive SMs in terrestrial streptomycetes [ 103 , 104 ]. Unfortunately, to date, this approach has been poorly explored within marine actinomycetes, even though metabolomic data underlined the dramatic impact such combinations had on the SM profiles of marine Micromonosporaceae [ 27 ].…”

Section: Co-cultivation and Other Environmental Cuesmentioning

confidence: 99%

Extending the “One Strain Many Compounds” (OSMAC) Principle to Marine Microorganisms

et al. 2018

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Genomic data often highlights an inconsistency between the number of gene clusters identified using bioinformatic approaches as potentially producing secondary metabolites and the actual number of chemically characterized secondary metabolites produced by any given microorganism. Such gene clusters are generally considered as “silent”, meaning that they are not expressed under laboratory conditions. Triggering expression of these “silent” clusters could result in unlocking the chemical diversity they control, allowing the discovery of novel molecules of both medical and biotechnological interest. Therefore, both genetic and cultivation-based techniques have been developed aimed at stimulating expression of these “silent” genes. The principles behind the cultivation based approaches have been conceptualized in the “one strain many compounds” (OSMAC) framework, which underlines how a single strain can produce different molecules when grown under different environmental conditions. Parameters such as, nutrient content, temperature, and rate of aeration can be easily changed, altering the global physiology of a microbial strain and in turn significantly affecting its secondary metabolism. As a direct extension of such approaches, co-cultivation strategies and the addition of chemical elicitors have also been used as cues to activate “silent” clusters. In this review, we aim to provide a focused and comprehensive overview of these strategies as they pertain to marine microbes. Moreover, we underline how changes in some parameters which have provided important results in terrestrial microbes, but which have rarely been considered in marine microorganisms, may represent additional strategies to awaken “silent” gene clusters in marine microbes. Unfortunately, the empirical nature of the OSMAC approach forces scientists to perform extensive laboratory experiments. Nevertheless, we believe that some computation and experimental based techniques which are used in other disciplines, and which we discuss; could be effectively employed to help streamline the OSMAC based approaches. We believe that natural products discovery in marine microorganisms would be greatly aided through the integration of basic microbiological approaches, computational methods, and technological innovations, thereby helping unearth much of the as yet untapped potential of these microorganisms.

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Umezawamides, new bioactive polycyclic tetramate macrolactams isolated from a combined-culture of Umezawaea sp. and mycolic acid-containing bacterium

Cited by 28 publications

References 18 publications

Genome Mining of Marine-Derived Streptomyces sp. SCSIO 40010 Leads to Cytotoxic New Polycyclic Tetramate Macrolactams

Genome Mining of Marine-Derived Streptomyces sp. SCSIO 40010 Leads to Cytotoxic New Polycyclic Tetramate Macrolactams

High Culturable Bacterial Diversity From a European Desert: The Tabernas Desert

Extending the “One Strain Many Compounds” (OSMAC) Principle to Marine Microorganisms

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