Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23
Chemical examination of the ethyl acetate extract from the fermentation broth of the marine-derived bacterium Bacillus licheniformis resulted in the isolation of two new glycolipids, ieodoglucomide C ( 1 ) and ieodoglycolipid ( 2 ). The structural characterization of 1 and 2 was achieved by extensiv...
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creator | Tareq, Fakir Shahidullah Lee, Hyi-Seung Lee, Yeon-Ju Lee, Jong Seok Shin, Hee Jae |
description | Chemical examination of the ethyl acetate extract from the fermentation broth of the marine-derived bacterium
Bacillus licheniformis
resulted in the isolation of two new glycolipids, ieodoglucomide C (
1
) and ieodoglycolipid (
2
). The structural characterization of
1
and
2
was achieved by extensive spectroscopic evidence, including 2D NMR experiments. A combination of chemical derivatization techniques followed by NMR studies, LC-MS data analysis and a literature review was deployed for the establishment of the stereo-configurations of
1
and
2
. Compounds
1
and
2
exhibited good antibiotic properties against
Staphylococcus aureus
,
Bacillus subtilis
,
Bacillus cereus
,
Salmonella typhi
,
Escherichia coli
and
Pseudomonas aeruginosa
with MICs ranging from 0.01 to 0.05 μM. Furthermore, the antifungal activity of
1
and
2
was evaluated against plant pathogenic fungi
Aspergillus niger
,
Rhizoctonia solani
,
Botrytis cinerea
and
Colletotrichum acutatum
as well as the human pathogen
Candida albicans
. Compounds
1
and
2
inhibited the mycelial growth of these pathogens with MIC values of 0.03–0.05 μM, revealing that these compounds are good candidates for the development of new fungicides. |
doi_str_mv | 10.1007/s11745-015-4014-z |
format | Article |
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Bacillus licheniformis
resulted in the isolation of two new glycolipids, ieodoglucomide C (
1
) and ieodoglycolipid (
2
). The structural characterization of
1
and
2
was achieved by extensive spectroscopic evidence, including 2D NMR experiments. A combination of chemical derivatization techniques followed by NMR studies, LC-MS data analysis and a literature review was deployed for the establishment of the stereo-configurations of
1
and
2
. Compounds
1
and
2
exhibited good antibiotic properties against
Staphylococcus aureus
,
Bacillus subtilis
,
Bacillus cereus
,
Salmonella typhi
,
Escherichia coli
and
Pseudomonas aeruginosa
with MICs ranging from 0.01 to 0.05 μM. Furthermore, the antifungal activity of
1
and
2
was evaluated against plant pathogenic fungi
Aspergillus niger
,
Rhizoctonia solani
,
Botrytis cinerea
and
Colletotrichum acutatum
as well as the human pathogen
Candida albicans
. Compounds
1
and
2
inhibited the mycelial growth of these pathogens with MIC values of 0.03–0.05 μM, revealing that these compounds are good candidates for the development of new fungicides.</description><identifier>ISSN: 0024-4201</identifier><identifier>EISSN: 1558-9307</identifier><identifier>DOI: 10.1007/s11745-015-4014-z</identifier><identifier>PMID: 25893812</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Acetates - analysis ; Acetates - chemistry ; Acetates - pharmacology ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antimicrobial properties ; Aspergillus niger ; Bacillus - classification ; Bacillus - metabolism ; Bacillus cereus ; Bacillus licheniformis ; Bacillus subtilis ; Bacteria - drug effects ; Biomedical and Life Sciences ; Botrytis cinerea ; Candida albicans ; Colletotrichum acutatum ; E coli ; Escherichia coli ; Fermentation ; Fungi - drug effects ; Fungicides ; Glycoconjugates - chemistry ; Glycoconjugates - pharmacology ; Glycolipids - chemistry ; Glycolipids - pharmacology ; Glycolipopeptide ; Life Sciences ; Lipidology ; Lipopeptides - chemistry ; Lipopeptides - pharmacology ; Literature reviews ; Medical Biochemistry ; Medicinal Chemistry ; Microbial Genetics and Genomics ; Microbial Sensitivity Tests ; Molecular Structure ; Monoacyldiglycosylglycerolipid ; Neurochemistry ; Nutrition ; Original Article ; Pathogens ; Pseudomonas aeruginosa ; Rhizoctonia solani ; Salmonella typhi ; Staphylococcus aureus ; Stereoconfiguration</subject><ispartof>Lipids, 2015-05, Vol.50 (5), p.513-519</ispartof><rights>AOCS 2015</rights><rights>2015 American Oil Chemists' Society (AOCS)</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5233-54e236460c4d03aabc4989c39fe0a91a7756b9a5bd7d96c3280de156af4e08523</citedby><cites>FETCH-LOGICAL-c5233-54e236460c4d03aabc4989c39fe0a91a7756b9a5bd7d96c3280de156af4e08523</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s11745-015-4014-z$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11745-015-4014-z$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,41464,42533,45550,45551,51294</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25893812$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tareq, Fakir Shahidullah</creatorcontrib><creatorcontrib>Lee, Hyi-Seung</creatorcontrib><creatorcontrib>Lee, Yeon-Ju</creatorcontrib><creatorcontrib>Lee, Jong Seok</creatorcontrib><creatorcontrib>Shin, Hee Jae</creatorcontrib><title>Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23</title><title>Lipids</title><addtitle>Lipids</addtitle><addtitle>Lipids</addtitle><description>Chemical examination of the ethyl acetate extract from the fermentation broth of the marine-derived bacterium
Bacillus licheniformis
resulted in the isolation of two new glycolipids, ieodoglucomide C (
1
) and ieodoglycolipid (
2
). The structural characterization of
1
and
2
was achieved by extensive spectroscopic evidence, including 2D NMR experiments. A combination of chemical derivatization techniques followed by NMR studies, LC-MS data analysis and a literature review was deployed for the establishment of the stereo-configurations of
1
and
2
. Compounds
1
and
2
exhibited good antibiotic properties against
Staphylococcus aureus
,
Bacillus subtilis
,
Bacillus cereus
,
Salmonella typhi
,
Escherichia coli
and
Pseudomonas aeruginosa
with MICs ranging from 0.01 to 0.05 μM. Furthermore, the antifungal activity of
1
and
2
was evaluated against plant pathogenic fungi
Aspergillus niger
,
Rhizoctonia solani
,
Botrytis cinerea
and
Colletotrichum acutatum
as well as the human pathogen
Candida albicans
. Compounds
1
and
2
inhibited the mycelial growth of these pathogens with MIC values of 0.03–0.05 μM, revealing that these compounds are good candidates for the development of new fungicides.</description><subject>Acetates - analysis</subject><subject>Acetates - chemistry</subject><subject>Acetates - pharmacology</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial properties</subject><subject>Aspergillus niger</subject><subject>Bacillus - classification</subject><subject>Bacillus - metabolism</subject><subject>Bacillus cereus</subject><subject>Bacillus licheniformis</subject><subject>Bacillus subtilis</subject><subject>Bacteria - drug effects</subject><subject>Biomedical and Life Sciences</subject><subject>Botrytis cinerea</subject><subject>Candida albicans</subject><subject>Colletotrichum acutatum</subject><subject>E coli</subject><subject>Escherichia coli</subject><subject>Fermentation</subject><subject>Fungi - drug effects</subject><subject>Fungicides</subject><subject>Glycoconjugates - chemistry</subject><subject>Glycoconjugates - pharmacology</subject><subject>Glycolipids - chemistry</subject><subject>Glycolipids - pharmacology</subject><subject>Glycolipopeptide</subject><subject>Life Sciences</subject><subject>Lipidology</subject><subject>Lipopeptides - chemistry</subject><subject>Lipopeptides - pharmacology</subject><subject>Literature reviews</subject><subject>Medical Biochemistry</subject><subject>Medicinal Chemistry</subject><subject>Microbial Genetics and Genomics</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Monoacyldiglycosylglycerolipid</subject><subject>Neurochemistry</subject><subject>Nutrition</subject><subject>Original Article</subject><subject>Pathogens</subject><subject>Pseudomonas aeruginosa</subject><subject>Rhizoctonia solani</subject><subject>Salmonella typhi</subject><subject>Staphylococcus aureus</subject><subject>Stereoconfiguration</subject><issn>0024-4201</issn><issn>1558-9307</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><sourceid>BENPR</sourceid><recordid>eNqNkU9vEzEQxS0EomnhA3BBlrhw6ML43-76CAmUSClwgAMny7Fni6vddWp3qdJPj9OECiEhOHnG-r2nN3qEPGPwigE0rzNjjVQVMFVJYLK6fUBmTKm20gKah2QGwGUlObAjcpzzZVmZ1OoxOeKq1aJlfEamJUYfL_rJxSF4pHNqR08Pn1sX-7AJ_pR-xBt6dr9n2qU4UEvPbQojVgtM4Qd6-ta66zJOw24KfT9l2gf3HcfQxTSETEEvF9_OuXhCHnW2z_j08J6Qr-_ffZl_qFafzpbzN6vKKS5EpSRyUcsanPQgrF07qVvthO4QrGa2aVS91latfeN17QRvwSNTte0kQlssTsjLve8mxasJ87UpKRz2vR0xTtmwuhVCCeDNf6BNrTTjTBf0xR_oZZzSWA65o6Ct4Y5ie8qlmHPCzmxSGGzaGgZmV5_Z12dKfWZXn7ktmucH52k9oL9X_OqrAM0euAk9bv_taFbLzwtQTBQl3ytzEY0XmH4L_dc8PwFi3rSW</recordid><startdate>201505</startdate><enddate>201505</enddate><creator>Tareq, Fakir Shahidullah</creator><creator>Lee, Hyi-Seung</creator><creator>Lee, Yeon-Ju</creator><creator>Lee, Jong Seok</creator><creator>Shin, Hee Jae</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7QL</scope><scope>7QP</scope><scope>7QR</scope><scope>7T7</scope><scope>7TK</scope><scope>7U9</scope><scope>7X7</scope><scope>7XB</scope><scope>88A</scope><scope>88E</scope><scope>8AO</scope><scope>8C1</scope><scope>8FD</scope><scope>8FE</scope><scope>8FH</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AEUYN</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BHPHI</scope><scope>BKSAR</scope><scope>C1K</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FR3</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>GNUQQ</scope><scope>H94</scope><scope>HCIFZ</scope><scope>K9.</scope><scope>LK8</scope><scope>M0S</scope><scope>M1P</scope><scope>M7N</scope><scope>M7P</scope><scope>P64</scope><scope>PCBAR</scope><scope>PHGZM</scope><scope>PHGZT</scope><scope>PJZUB</scope><scope>PKEHL</scope><scope>PPXIY</scope><scope>PQEST</scope><scope>PQGLB</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>7X8</scope></search><sort><creationdate>201505</creationdate><title>Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23</title><author>Tareq, Fakir Shahidullah ; Lee, Hyi-Seung ; Lee, Yeon-Ju ; Lee, Jong Seok ; Shin, Hee Jae</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5233-54e236460c4d03aabc4989c39fe0a91a7756b9a5bd7d96c3280de156af4e08523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Acetates - analysis</topic><topic>Acetates - chemistry</topic><topic>Acetates - pharmacology</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial properties</topic><topic>Aspergillus niger</topic><topic>Bacillus - classification</topic><topic>Bacillus - metabolism</topic><topic>Bacillus cereus</topic><topic>Bacillus licheniformis</topic><topic>Bacillus subtilis</topic><topic>Bacteria - drug effects</topic><topic>Biomedical and Life Sciences</topic><topic>Botrytis cinerea</topic><topic>Candida albicans</topic><topic>Colletotrichum acutatum</topic><topic>E coli</topic><topic>Escherichia coli</topic><topic>Fermentation</topic><topic>Fungi - drug effects</topic><topic>Fungicides</topic><topic>Glycoconjugates - chemistry</topic><topic>Glycoconjugates - pharmacology</topic><topic>Glycolipids - chemistry</topic><topic>Glycolipids - pharmacology</topic><topic>Glycolipopeptide</topic><topic>Life Sciences</topic><topic>Lipidology</topic><topic>Lipopeptides - chemistry</topic><topic>Lipopeptides - pharmacology</topic><topic>Literature reviews</topic><topic>Medical Biochemistry</topic><topic>Medicinal Chemistry</topic><topic>Microbial Genetics and Genomics</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Monoacyldiglycosylglycerolipid</topic><topic>Neurochemistry</topic><topic>Nutrition</topic><topic>Original Article</topic><topic>Pathogens</topic><topic>Pseudomonas aeruginosa</topic><topic>Rhizoctonia solani</topic><topic>Salmonella typhi</topic><topic>Staphylococcus aureus</topic><topic>Stereoconfiguration</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tareq, Fakir Shahidullah</creatorcontrib><creatorcontrib>Lee, Hyi-Seung</creatorcontrib><creatorcontrib>Lee, Yeon-Ju</creatorcontrib><creatorcontrib>Lee, Jong Seok</creatorcontrib><creatorcontrib>Shin, Hee Jae</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Calcium & Calcified Tissue Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>ProQuest Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Biology Database (Alumni Edition)</collection><collection>Medical Database (Alumni Edition)</collection><collection>ProQuest Pharma Collection</collection><collection>ProQuest Public Health Database</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni)</collection><collection>ProQuest One Sustainability</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>ProQuest Central</collection><collection>ProQuest Natural Science Collection</collection><collection>Earth, Atmospheric & Aquatic Science Collection</collection><collection>Environmental Sciences and Pollution Management</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central</collection><collection>Engineering Research Database</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Central Student</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>ProQuest Biological Science Collection</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>PML(ProQuest Medical Library)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biological Science Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>ProQuest Earth, Atmospheric & Aquatic Science Database</collection><collection>ProQuest Central (New)</collection><collection>ProQuest One Academic (New)</collection><collection>ProQuest Health & Medical Research Collection</collection><collection>ProQuest One Academic Middle East (New)</collection><collection>ProQuest One Health & Nursing</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Applied & Life Sciences</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>MEDLINE - Academic</collection><jtitle>Lipids</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tareq, Fakir Shahidullah</au><au>Lee, Hyi-Seung</au><au>Lee, Yeon-Ju</au><au>Lee, Jong Seok</au><au>Shin, Hee Jae</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23</atitle><jtitle>Lipids</jtitle><stitle>Lipids</stitle><addtitle>Lipids</addtitle><date>2015-05</date><risdate>2015</risdate><volume>50</volume><issue>5</issue><spage>513</spage><epage>519</epage><pages>513-519</pages><issn>0024-4201</issn><eissn>1558-9307</eissn><abstract>Chemical examination of the ethyl acetate extract from the fermentation broth of the marine-derived bacterium
Bacillus licheniformis
resulted in the isolation of two new glycolipids, ieodoglucomide C (
1
) and ieodoglycolipid (
2
). The structural characterization of
1
and
2
was achieved by extensive spectroscopic evidence, including 2D NMR experiments. A combination of chemical derivatization techniques followed by NMR studies, LC-MS data analysis and a literature review was deployed for the establishment of the stereo-configurations of
1
and
2
. Compounds
1
and
2
exhibited good antibiotic properties against
Staphylococcus aureus
,
Bacillus subtilis
,
Bacillus cereus
,
Salmonella typhi
,
Escherichia coli
and
Pseudomonas aeruginosa
with MICs ranging from 0.01 to 0.05 μM. Furthermore, the antifungal activity of
1
and
2
was evaluated against plant pathogenic fungi
Aspergillus niger
,
Rhizoctonia solani
,
Botrytis cinerea
and
Colletotrichum acutatum
as well as the human pathogen
Candida albicans
. Compounds
1
and
2
inhibited the mycelial growth of these pathogens with MIC values of 0.03–0.05 μM, revealing that these compounds are good candidates for the development of new fungicides.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><pmid>25893812</pmid><doi>10.1007/s11745-015-4014-z</doi><tpages>7</tpages></addata></record> |
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ispartof | Lipids, 2015-05, Vol.50 (5), p.513-519 |
issn | 0024-4201 1558-9307 |
language | eng |
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source | Wiley-Blackwell Journals; MEDLINE; Springer Journals |
subjects | Acetates - analysis Acetates - chemistry Acetates - pharmacology Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antifungal Agents - chemistry Antifungal Agents - pharmacology Antimicrobial properties Aspergillus niger Bacillus - classification Bacillus - metabolism Bacillus cereus Bacillus licheniformis Bacillus subtilis Bacteria - drug effects Biomedical and Life Sciences Botrytis cinerea Candida albicans Colletotrichum acutatum E coli Escherichia coli Fermentation Fungi - drug effects Fungicides Glycoconjugates - chemistry Glycoconjugates - pharmacology Glycolipids - chemistry Glycolipids - pharmacology Glycolipopeptide Life Sciences Lipidology Lipopeptides - chemistry Lipopeptides - pharmacology Literature reviews Medical Biochemistry Medicinal Chemistry Microbial Genetics and Genomics Microbial Sensitivity Tests Molecular Structure Monoacyldiglycosylglycerolipid Neurochemistry Nutrition Original Article Pathogens Pseudomonas aeruginosa Rhizoctonia solani Salmonella typhi Staphylococcus aureus Stereoconfiguration |
title | Ieodoglucomide C and Ieodoglycolipid, New Glycolipids from a Marine-Derived Bacterium Bacillus licheniformis 09IDYM23 |
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