Antibacterial activity of cyclo(<scp>L</scp>-Pro-<scp>L</scp>-Tyr) and cyclo(<scp>D</scp>-Pro-<scp>L</scp>-Tyr) from <i>Streptomyces</i> sp<i>.</i> strain 22-4 against phytopathogenic bacteria

Wattana-Amorn, Pakorn; Charoenwongsa, Waranya; Williams, Christopher; Crump, Matthew P.; Apichaisataienchote, Busaya

doi:10.1080/14786419.2015.1095747

Cited by 74 publications

(41 citation statements)

References 13 publications

(11 reference statements)

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“…Cyclo(L‐Pro‐L‐Tyr) is a cyclic dipeptide (diketopiperiazine) identified in 100% of our samples and can be produced by Alternaria alternata or bacteria including Streptomyces , but we only identified A . alternata in 10.7% of our samples with culturing and 27.3% with DNA sequencing . However, we cannot exclude a possibility that this metabolite might be also produced by other members of the Pleosporales of which we identified a broad diversity using DNA sequencing .…”

Section: Discussionmentioning

confidence: 86%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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Recent developments in molecular and chemical methods have enabled the analysis of fungal DNA and secondary metabolites, often produced during fungal growth, in environmental samples. We compared 3 fungal analytical methods by analysing floor dust samples collected from an office building for fungi using viable culture, internal transcribed spacer (ITS) sequencing and secondary metabolites using liquid chromatography-tandem mass spectrometry. Of the 32 metabolites identified, 29 had a potential link to fungi with levels ranging from 0.04 (minimum for alternariol monomethylether) to 5700 ng/g (maximum for neoechinulin A). The number of fungal metabolites quantified per sample ranged from 8 to 16 (average = 13/sample). We identified 216 fungal operational taxonomic units (OTUs) with the number per sample ranging from 6 to 29 (average = 18/sample). We identified 37 fungal species using culture, and the number per sample ranged from 2 to 13 (average = 8/sample). Agreement in identification between ITS sequencing and culturing was weak (kappa = -0.12 to 0.27). The number of cultured fungal species poorly correlated with OTUs, which did not correlate with the number of metabolites. These suggest that using multiple measurement methods may provide an improved understanding of fungal exposures in indoor environments and that secondary metabolites may be considered as an additional source of exposure.

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Section: Discussionmentioning

confidence: 86%

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

et al. 2018

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“…S10C). Compounds 1, 2, and 3 were found to be cinnamamide, lobophorin A, and cyclo-L-proline-L-tyrosine, respectively, by comparing 1 H (700 MHz, methanol-d 4 ) and 13 C (176 MHz, methanol-d 4 ) spectra data ( Supplementary Table S6) with data reported in the literature 13,17,37 .…”

Section: Resultsmentioning

confidence: 99%

“…Cyclo-L-proline-L-tyrosine was first reported to be produced by Streptomyces sp. strain 22-4 17 . It had activities against three economically important plant pathogens, Xanthomonas axonopodis pv.…”

Section: Discussionmentioning

confidence: 99%

Streptomyces sp. VN1, a producer of diverse metabolites including non-natural furan-type anticancer compound

Nguyen

Pokhrel

Nguyen

et al. 2020

Sci Rep

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Streptomyces sp. VN1 was isolated from the coastal region of Phu Yen Province (central Viet Nam). Morphological, physiological, and whole genome phylogenetic analyses suggested that strain Streptomyces sp. VN1 belonged to genus Streptomyces. Whole genome sequencing analysis showed its genome was 8,341,703 base pairs in length with GC content of 72.5%. Diverse metabolites, including cinnamamide, spirotetronate antibiotic lobophorin A, diketopiperazines cyclo-L-proline-L-tyrosine, and a unique furan-type compound were isolated from Streptomyces sp. VN1. Structures of these compounds were studied by HR-Q-TOF ESI/MS/MS and 2D NMR analyses. Bioassay-guided purification yielded a furan-type compound which exhibited in vitro anticancer activity against AGS, HCT116, A375M, U87MG, and A549 cell lines with IC 50 values of 40.5, 123.7, 84.67, 50, and 58.64 µM, respectively. In silico genome analysis of the isolated Streptomyces sp. VN1 contained 34 gene clusters responsible for the biosynthesis of known and/or novel secondary metabolites, including different types of terpene, T1PKS, T2PKS, T3PKS, NRPS, and hybrid PKS-NRPS. Genome mining with HR-Q-TOF ESI/MS/MS analysis of the crude extract confirmed the biosynthesis of lobophorin analogs. This study indicates that Streptomyces sp. VN1 is a promising strain for biosynthesis of novel natural products. Natural products (NPs) have been starting points of drug discovery for several decades. Major antimicrobials and chemotherapeutics entering clinical trials are often based on NPs 1,2. Drugs with a natural origin can be produced as primary or secondary metabolites from versatile living organisms. Different microorganisms such as Streptomyces, myxobacteria and uncultured bacteria are major sources of such beneficial NPs 3,4. Moreover, different metabolic engineering approaches and sophisticated techniques employing systems biology or synthetic biology can assist in harnessing the full potential of these bacteria in terms of productivity or creating diverse products 5,6. Hence, there is renewed interest in mining microorganisms for new leads owing to the remarkable success of microbial metabolites as starting points for developing effective antibiotics, anticancer agents, and agrochemicals 7. Streptomyces are Gram-positive, aerobic bacteria in the order of Actinomycetales within the class of Actinobacteria. Genus Streptomyces was first proposed by Waksman and Henrici in 1943. It was classified into the family of Streptomycetaceae based on its morphology and cell wall chemotype 8. Previous studies have shown that more than 74% of current antibiotics are derived from the genus Streptomyces 9. Using integrated approaches of compound screening and drug development, Streptomyces arsenal has been found to be able to combat antibiotic resistance 5. Multiple approaches such as ribosome engineering 10 and genome mining 11 have been used to find new secondary metabolites in old Streptomyces strains. Besides the effort to work on old strains to explore novel biosynthetic gene clusters (BGCs),...

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“…These compounds were cyclo(Tyr-Pro), previously reported from Aspergillus flavipes and Streptomyces sp. strains (Barrow and Sun 1994;Wattana-Amorn et al 2015), and cyclo(Phe-4-hydroxyPro), reported from Aureobasidium pullulans and unclassified marine bacteria strains (Shigemori et al 1998;Fdhila et al 2003), both diketopiperazines with varying stereochemical configurations. The compound eluting at 2.19 min with a m/z 284.1393 [M + H] + matched a single entry in Antibase, tryptophan-dehydrobutyrine diketopiperazine (Δ ppm = 0.14) (Kakinuma et al 1974).…”

Section: Chemical Analysis Of Bioactive Extractsmentioning

confidence: 99%

Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

et al. 2016

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Shrimp fisheries along the Brazilian coast have significant environmental impact due to high by-catch rates (21 kg per kilogram of shrimp). Typically discarded, by-catch contains many invertebrates that may host a great variety of bacterial genera, some of which may produce bioactive natural products with biotechnological applications. Therefore, to utilize by-catch that is usually discarded we explored the biotechnological potential of culturable bacteria of two abundant by-catch invertebrate species, the snail Olivancillaria urceus and the sea star Luidia senegalensis. Sediment from the collection area was also investigated. Utilizing multiple isolation approaches, 134 isolates were obtained from the invertebrates and sediment. Small-subunit rRNA (16S) gene sequencing revealed that the isolates belonged to Proteobacteria, Firmicutes and Actinobacteria phyla and were distributed among 28 genera. Several genera known for their capacity to produce bioactive natural products (Micromonospora, Streptomyces, Serinicoccus and Verrucosispora) were retrieved from the invertebrate samples. To query the bacterial isolates for their ability to produce bioactive metabolites, all strains were fermented and fermentation extracts profiled by UP LC-HRMS and tested for antimicrobial activity. Four strains exhibited antimicrobial activity against methicillin-resistant Staphylococcus aureus (MRSA) and Staphylococcus warneri.

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Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria

Cited by 74 publications

References 13 publications

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Characterization of fungi in office dust: Comparing results of microbial secondary metabolites, fungal internal transcribed spacer region sequencing, viable culture and other microbial indices

Streptomyces sp. VN1, a producer of diverse metabolites including non-natural furan-type anticancer compound

Bioprospecting from cultivable bacterial communities of marine sediment and invertebrates from the underexplored Ubatuba region of Brazil

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