Isolation, structure elucidation and antibacterial activity of methyl-4,8-dimethylundecanate from the marine actinobacterium Streptomyces albogriseolus ECR64

Thirumurugan, D.; Vijayakumar, R.; Vadivalagan, Chithravel; Pushparaj, Karthika; Khan, Kashif Ullah

doi:10.1016/j.micpath.2018.05.025

Cited by 33 publications

(25 citation statements)

References 17 publications

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“…In the current study, among the three different solvents used to extract the antimicrobial compounds, the ethyl acetate extract showed the maximum activity against all the pathogens tested. It has already been reported by Thirumurugan et al [20] that the ethyl acetate extract showed maximum antibacterial efficacy on all tested pathogens. Baskaran et al [21] has also reported that out of five different solvents used to extract the antimicrobial compounds of Streptomyces parvulus, the ethyl acetate extract showed remarkable activity against the eleven pathogenic bacteria and the six tested fungal pathogens.…”

Section: Discussionsupporting

confidence: 51%

Isolation, Characterization and Chemical Synthesis of Large Spectrum Antimicrobial Cyclic Dipeptide (l-leu-l-pro) from Streptomyces misionensis V16R3Y1 Bacteria Extracts. A Novel 1H NMR Metabolomic Approach

Saadouli

Euch

Trabelsi³

et al. 2020

Antibiotics

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Streptomyces is the most frequently described genus of Actinomycetes, a producer of biologically active secondary metabolites. Indeed, the Streptomyces species produces about 70% of antibiotics and 60% of antifungal molecules used in agriculture. Our study was carried out with the goal of isolating and identifying antimicrobial secondary metabolites from Streptomyces misionensis V16R3Y1 isolated from the date palm rhizosphere (southern Tunisia). This strain presented a broad range of antifungal activity against Fusarium oxysporum, Aspergillus flavus, Penicillium expansum, Aspergillus niger, Candida albicans, Candida metapsilosis, and Candida parapsilosis and antibacterial activity against human pathogenic bacteria, including Escherichia fergusonii, Staphylococcus aureus, Salmonella enterica, Enterococcus faecalis, Bacillus cereus and Pseudomonas aeruginosa. The purification procedure entailed ethyl acetate extract, silica gel column, and thin layer chromatography. Based on 1H NMR metabolomic procedure application, also supported by the GC-MS analysis, cyclic dipeptide (l-Leucyl-l-Proline) was identified as the major compound in the bioactive fraction. In order to confirm the identity of the active compound and to have a large quantity thereof, a chemical synthesis of the cyclic dipeptide was performed. The synthetic compound was obtained with a very good yield (50%) and presented almost the same effect compared to the extracted fraction. This study indicates for the first time that Streptomyces misionensis V16R3Y1 exhibits a broad spectrum of antimicrobial activities, produced cyclic dipeptide (l-Leucyl-l-Proline) and might have potential use as a natural agent for pharmaceutical and agri-food applications.

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Section: Discussionsupporting

confidence: 51%

Isolation, Characterization and Chemical Synthesis of Large Spectrum Antimicrobial Cyclic Dipeptide (l-leu-l-pro) from Streptomyces misionensis V16R3Y1 Bacteria Extracts. A Novel 1H NMR Metabolomic Approach

Saadouli

Euch

Trabelsi³

et al. 2020

Antibiotics

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“…Thus, the isolates belonging to this clad were designated as S. albogriseolus strains DSD040 T (1472 bp), DSD041 T (1479 bp), DSD042 T (1448 bp), and DSD043 T (1493 bp). Previous reports on S. albogriseolus showed that strains related to this species were isolated from terrestrial, mangrove, and marine environments [ 58 , 59 , 60 ]. For strains isolated from sea sediments, it was reported to produce methyl-4,8-dimethylundecanate that can inhibit the growth of fish pathogenic bacteria and be used as an alternative drug for aquaculture management [ 59 ].…”

Section: Resultsmentioning

confidence: 99%

“…Previous reports on S. albogriseolus showed that strains related to this species were isolated from terrestrial, mangrove, and marine environments [ 58 , 59 , 60 ]. For strains isolated from sea sediments, it was reported to produce methyl-4,8-dimethylundecanate that can inhibit the growth of fish pathogenic bacteria and be used as an alternative drug for aquaculture management [ 59 ]. Moreover, S. albogriseolus isolated from marine sediments of Jiaozhou Bay, China, produced new lactone echinosporins with antiproliferative activity against human chronic myelogenous leukemia (K562) (IC 50 = 91.5 ± 26.5 µM) and human colorectal adenocarcinoma (HCT-15) (IC 50 = 25.1 ± 1.8 µM) [ 60 ].…”

Section: Resultsmentioning

confidence: 99%

“…There were antibiotic and anticancer compounds reported from S. albogriseolus . An antibiotic methyl-4,8-dimethylundecanate ( Supplemental Figure S7A ) was isolated from a marine S. albogriseolus strain [ 59 ]. Additionally, there were anticancer compounds such as alkaloid albogrisins ( Supplemental Figure S7B ) and eunicellin diterpenoids microeunicellols ( Supplemental Figure S7C ) reported from S. albogriseolus strains [ 88 , 89 ].…”

Section: Resultsmentioning

confidence: 99%

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Insights into the Variation in Bioactivities of Closely Related Streptomyces Strains from Marine Sediments of the Visayan Sea against ESKAPE and Ovarian Cancer

et al. 2021

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Marine sediments host diverse actinomycetes that serve as a source of new natural products to combat infectious diseases and cancer. Here, we report the biodiversity, bioactivities against ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) and ovarian cancer, and metabolites variation among culturable actinomycetes isolated from the marine sediments of Visayan Sea, Philippines. We identified 15 Streptomyces species based on a 16S rRNA gene sequence analysis. The crude extracts of 10 Streptomyces species have inhibited the growth of ESKAPE pathogens with minimum inhibitory concentration (MIC) values ranging from 0.312 mg/mL to 20 mg/mL depending on the strain and pathogens targeted. Additionally, ten crude extracts have antiproliferative activity against A2780 human ovarian carcinoma at 2 mg/mL. To highlight, we observed that four phylogenetically identical Streptomyces albogriseolus strains demonstrated variation in antibiotic and anticancer activities. These strains harbored type I and II polyketide synthase (PKS) and non-ribosomal synthetase (NRPS) genes in their genomes, implying that their bioactivity is independent of the polymerase chain reaction (PCR)-detected bio-synthetic gene clusters (BGCs) in this study. Metabolite profiling revealed that the taxonomically identical strains produced core and strain-specific metabolites. Thus, the chemical diversity among these strains influences the variation observed in their biological activities. This study expanded our knowledge on the potential of marine-derived Streptomyces residing from the unexplored regions of the Visayan Sea as a source of small molecules against ESKAPE pathogens and cancer. It also highlights that Streptomyces species strains produce unique strain-specific secondary metabolites; thus, offering new chemical space for natural product discovery.

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“…In addition, because it has low toxicity, its effect on biological cells cannot be considered. Small and bioactive compounds mostly dissolve in ethyl acetate (Saadouli et al, 2020; Tan et al, 2020; Thirumurugan et al, 2018). Metabolites profiling on TLC plates using p ‐anisaldehyde as staining reagent were conducted to visualize different types of compounds.…”

Section: Discussionmentioning

confidence: 99%

Antivibriosis and cytotoxicity of Actinobacteria associated with red seaweed Gelidiella acerosa

2021

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Vibriosis causes a problem in aquaculture and human health. The antibiotic resistance and the limited availability of antimicrobial agents are the driving force for searching for new antivibrio compounds from natural products. Herein, we evaluated ten marine Actinobacteria isolated from red seaweed Gelidiella acerosa for antivibriosis, cytotoxicity and secondary metabolites genes in the way to find a new antivibrio agent. Five Actinobacteria isolates exhibited activity against Vibrio alginolyticus and Vibrio parahaemolyticus with MIC ranging from 0.625 to 5 µg/µl. All isolates displayed no cytotoxicity against Vero cell line except for isolate DR‐2R‐115–8. All isolates harbour nrps gene, which might indicate that these isolates have great potential in the production of bioactive peptides while none of the isolates showed the presence of pks I, II and hmgcr genes. Identification of ten isolates of marine Actinobacteria associated with red algae was classified into four genera of Brevibacterium, Nocardiopsis, Allokutzneria and Brachybacterium. Our study revealed that the marine Actinobacteria associated with red algae Gelidiella acerosa were promising sources for controlling vibriosis.

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Isolation, structure elucidation and antibacterial activity of methyl-4,8-dimethylundecanate from the marine actinobacterium Streptomyces albogriseolus ECR64

Cited by 33 publications

References 17 publications

Isolation, Characterization and Chemical Synthesis of Large Spectrum Antimicrobial Cyclic Dipeptide (l-leu-l-pro) from Streptomyces misionensis V16R3Y1 Bacteria Extracts. A Novel 1H NMR Metabolomic Approach

Isolation, Characterization and Chemical Synthesis of Large Spectrum Antimicrobial Cyclic Dipeptide (l-leu-l-pro) from Streptomyces misionensis V16R3Y1 Bacteria Extracts. A Novel 1H NMR Metabolomic Approach

Insights into the Variation in Bioactivities of Closely Related Streptomyces Strains from Marine Sediments of the Visayan Sea against ESKAPE and Ovarian Cancer

Antivibriosis and cytotoxicity of Actinobacteria associated with red seaweed Gelidiella acerosa

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