Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification
[Display omitted] Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4–12 were unamb...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 25; no. 16; pp. 3125 - 3128 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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Elsevier Ltd
15.08.2015
Elsevier |
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| Abstract | [Display omitted]
Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4–12 were unambiguously identified as a series of simple and re-arranged diketopiperazines by analysis of spectroscopic data. t-Butoxycarbonyl group (BOC) derivatization was used to separate the intractable mixture of 4 and 5. When all compounds were evaluated for antimicrobial activity against gram positive bacteria, the isolated metabolites showed moderate to weak effects, while the semisynthetic derivatives 4a and 5a displayed strong activity comparable to the positive control, tetracycline against gram positive bacteria. |
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| AbstractList | Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4-12 were unambiguously identified as a series of simple and re-arranged diketopiperazines by analysis of spectroscopic data. t-Butoxycarbonyl group (BOC) derivatization was used to separate the intractable mixture of 4 and 5. When all compounds were evaluated for antimicrobial activity against gram positive bacteria, the isolated metabolites showed moderate to weak effects, while the semisynthetic derivatives 4a and 5a displayed strong activity comparable to the positive control, tetracycline against gram positive bacteria. Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4-12 were unambiguously identified as a series of simple and re-arranged diketopiperazines by analysis of spectroscopic data. t-Butoxycarbonyl group (BOC) derivatization was used to separate the intractable mixture of 4 and 5. When all compounds were evaluated for antimicrobial activity against gram positive bacteria, the isolated metabolites showed moderate to weak effects, while the semisynthetic derivatives 4a and 5a displayed strong activity comparable to the positive control, tetracycline against gram positive bacteria. (C) 2015 Elsevier Ltd. All rights reserved. [Display omitted] Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal internal transcribed spacer (ITS) region was identified as Aspergillus fumigatus. The isolated fungal metabolites 4–12 were unambiguously identified as a series of simple and re-arranged diketopiperazines by analysis of spectroscopic data. t-Butoxycarbonyl group (BOC) derivatization was used to separate the intractable mixture of 4 and 5. When all compounds were evaluated for antimicrobial activity against gram positive bacteria, the isolated metabolites showed moderate to weak effects, while the semisynthetic derivatives 4a and 5a displayed strong activity comparable to the positive control, tetracycline against gram positive bacteria. |
| Author | El-Gendy, Bahaa El-Dien M. Rateb, Mostafa E. |
| Author_xml | – sequence: 1 givenname: Bahaa El-Dien M. surname: El-Gendy fullname: El-Gendy, Bahaa El-Dien M. organization: Chemistry Department, Faculty of Science, Benha University, Benha 13518, Egypt – sequence: 2 givenname: Mostafa E. surname: Rateb fullname: Rateb, Mostafa E. email: m.rateb@abdn.ac.uk organization: Pharmacognosy Department, Faculty of Pharmacy, Beni-Suef University, Beni-Suef 62514, Egypt |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26099531$$D View this record in MEDLINE/PubMed |
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| Keywords | Diketopiperazine BOC group DNA amplification Antibacterial Marine fungus ENDOPHYTIC FUNGUS METABOLITES POTENT 2,5-DIKETOPIPERAZINES BIOLOGICAL-ACTIVITY INHIBITOR DISCOVERY |
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Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of... Nine diketopiperazines were characterized from the culture of marine fungal isolate MR2012 which based on DNA amplification and sequencing of the fungal... |
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| SubjectTerms | Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - isolation & purification Anti-Bacterial Agents - pharmacology Antibacterial Aspergillus fumigatus - chemistry Aspergillus fumigatus - metabolism BOC group Chemistry Chemistry, Medicinal Chemistry, Organic Diketopiperazine Diketopiperazines - chemistry Diketopiperazines - isolation & purification Diketopiperazines - pharmacology DNA amplification Fungi - chemistry Fungi - classification Fungi - metabolism Gram-Positive Bacteria - drug effects Life Sciences & Biomedicine Marine fungus Microbial Sensitivity Tests Pharmacology & Pharmacy Phylogeny Physical Sciences Sargassum - microbiology Science & Technology Structure-Activity Relationship |
| Title | Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification |
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