New Acylated Sulfoglycolipids and Digalactolipids and Related Known Glycolipids from Cyanobacteria with a Potential To Inhibit the Reverse Transcriptase of HIV-1
Five novel diacylated sulfoglycolipids (1−5) were isolated from the cyanobacterium Scytonema sp. (TAU strain SL-30-1-4) and four novel acylated diglycolipids (6−9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycol...
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| Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 1997-12, Vol.60 (12), p.1251-1260 |
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| container_title | Journal of natural products (Washington, D.C.) |
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| creator | Reshef, Vered Mizrachi, Erez Maretzki, Tal Silberstein, Colin Loya, Shoshana Hizi, Amnon Carmeli, Shmuel |
| description | Five novel diacylated sulfoglycolipids (1−5) were isolated from the cyanobacterium Scytonema sp. (TAU strain SL-30-1-4) and four novel acylated diglycolipids (6−9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycolipids isolated from these two and three other strains of cyanobacteria, Phormidium tenue (TAU strain IL-144-1), O. trichoides (TAU strain IL-104-3-2), and O. limnetica (TAU strain NG-4-1-2), were found to inhibit HIV-1 RT enzymatic activity to different extents. The structure elucidation of the various compounds is based on the selective hydrolysis of the glycerol ester moieties, GCMS analysis of the methyl ester derivatives of the liberated fatty acids, homo- and heteronuclear-2D-NMR techniques, and MS. The use of negative-ion FABMS for analyzing the combination and distribution of the fatty acids in glycolipids is demonstrated. |
| doi_str_mv | 10.1021/np970327m |
| format | Article |
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(TAU strain SL-30-1-4) and four novel acylated diglycolipids (6−9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycolipids isolated from these two and three other strains of cyanobacteria, Phormidium tenue (TAU strain IL-144-1), O. trichoides (TAU strain IL-104-3-2), and O. limnetica (TAU strain NG-4-1-2), were found to inhibit HIV-1 RT enzymatic activity to different extents. The structure elucidation of the various compounds is based on the selective hydrolysis of the glycerol ester moieties, GCMS analysis of the methyl ester derivatives of the liberated fatty acids, homo- and heteronuclear-2D-NMR techniques, and MS. The use of negative-ion FABMS for analyzing the combination and distribution of the fatty acids in glycolipids is demonstrated.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np970327m</identifier><identifier>PMID: 9428159</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>AIDS/HIV ; Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents ; Applied microbiology ; Biological and medical sciences ; Cyanobacteria - chemistry ; Cyanobacteria - drug effects ; Cyanobacteria - enzymology ; Fatty Acids - metabolism ; Fundamental and applied biological sciences. Psychology ; General aspects ; Glycolipids - isolation & purification ; Glycolipids - pharmacology ; Hydrolysis ; Magnetic Resonance Spectroscopy ; Microbiology ; Reverse Transcriptase Inhibitors - isolation & purification ; Reverse Transcriptase Inhibitors - pharmacology ; Spectrometry, Mass, Fast Atom Bombardment ; Spectrophotometry, Ultraviolet ; Spectroscopy, Fourier Transform Infrared</subject><ispartof>Journal of natural products (Washington, D.C.), 1997-12, Vol.60 (12), p.1251-1260</ispartof><rights>Copyright © 1997 American Chemical Society and American Society of Pharmacognosy</rights><rights>1998 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a414t-317e22ad2ef262aa9fab06c45d4701713f3075544df4c738a61054e978b3cf4f3</citedby><cites>FETCH-LOGICAL-a414t-317e22ad2ef262aa9fab06c45d4701713f3075544df4c738a61054e978b3cf4f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/np970327m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/np970327m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=2104080$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/9428159$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reshef, Vered</creatorcontrib><creatorcontrib>Mizrachi, Erez</creatorcontrib><creatorcontrib>Maretzki, Tal</creatorcontrib><creatorcontrib>Silberstein, Colin</creatorcontrib><creatorcontrib>Loya, Shoshana</creatorcontrib><creatorcontrib>Hizi, Amnon</creatorcontrib><creatorcontrib>Carmeli, Shmuel</creatorcontrib><title>New Acylated Sulfoglycolipids and Digalactolipids and Related Known Glycolipids from Cyanobacteria with a Potential To Inhibit the Reverse Transcriptase of HIV-1</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Five novel diacylated sulfoglycolipids (1−5) were isolated from the cyanobacterium Scytonema sp. (TAU strain SL-30-1-4) and four novel acylated diglycolipids (6−9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycolipids isolated from these two and three other strains of cyanobacteria, Phormidium tenue (TAU strain IL-144-1), O. trichoides (TAU strain IL-104-3-2), and O. limnetica (TAU strain NG-4-1-2), were found to inhibit HIV-1 RT enzymatic activity to different extents. The structure elucidation of the various compounds is based on the selective hydrolysis of the glycerol ester moieties, GCMS analysis of the methyl ester derivatives of the liberated fatty acids, homo- and heteronuclear-2D-NMR techniques, and MS. The use of negative-ion FABMS for analyzing the combination and distribution of the fatty acids in glycolipids is demonstrated.</description><subject>AIDS/HIV</subject><subject>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</subject><subject>Applied microbiology</subject><subject>Biological and medical sciences</subject><subject>Cyanobacteria - chemistry</subject><subject>Cyanobacteria - drug effects</subject><subject>Cyanobacteria - enzymology</subject><subject>Fatty Acids - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General aspects</subject><subject>Glycolipids - isolation & purification</subject><subject>Glycolipids - pharmacology</subject><subject>Hydrolysis</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Microbiology</subject><subject>Reverse Transcriptase Inhibitors - isolation & purification</subject><subject>Reverse Transcriptase Inhibitors - pharmacology</subject><subject>Spectrometry, Mass, Fast Atom Bombardment</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><issn>0163-3864</issn><issn>1520-6025</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1997</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkc1u1DAUhSMEKtPCggdA8gIqsQj4L3GyLAO0AxWMaCgSG-vGsTtuk3iwPQzzOLwpRhmNumB15Xu-c2Sdm2XPCH5NMCVvxnUtMKNieJDNSEFxXmJaPMxmmJQsZ1XJH2fHIdxijBmui6PsqOa0IkU9y_581lt0pnY9RN2hq01v3E2_U663a9sFBGOH3tkb6EHF-7uvejJ8Gt12ROf3HMa7Ac13MLo2ebS3gLY2rhCgpYt6jBZ61Di0GFe2tRHFlU5hv7QPGjUexqC8XUdIL2fQxeI6J0-yRwb6oJ_u50n27cP7Zn6RX345X8zPLnPghMecEaEphY5qQ0sKUBtocal40XGBiSDMMCyKgvPOcCVYBSXBBde1qFqmDDfsJDudctfe_dzoEOVgg9J9D6N2myBFnYotCU3gqwlU3oXgtZFrbwfwO0mw_HcOeThHYp_vQzftoLsDue8_6S_2OgQFvUkNKBsOGCWY4wonLJ8wG6L-fZDB38lSMFHIZnkll99_XBfkYyPfJv7lxIMK8tZt_Jia-8_3_gKEd68d</recordid><startdate>19971201</startdate><enddate>19971201</enddate><creator>Reshef, Vered</creator><creator>Mizrachi, Erez</creator><creator>Maretzki, Tal</creator><creator>Silberstein, Colin</creator><creator>Loya, Shoshana</creator><creator>Hizi, Amnon</creator><creator>Carmeli, Shmuel</creator><general>American Chemical Society</general><general>American Society of Pharmacognosy</general><scope>BSCLL</scope><scope>IQODW</scope><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>7X8</scope></search><sort><creationdate>19971201</creationdate><title>New Acylated Sulfoglycolipids and Digalactolipids and Related Known Glycolipids from Cyanobacteria with a Potential To Inhibit the Reverse Transcriptase of HIV-1</title><author>Reshef, Vered ; Mizrachi, Erez ; Maretzki, Tal ; Silberstein, Colin ; Loya, Shoshana ; Hizi, Amnon ; Carmeli, Shmuel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a414t-317e22ad2ef262aa9fab06c45d4701713f3075544df4c738a61054e978b3cf4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1997</creationdate><topic>AIDS/HIV</topic><topic>Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents</topic><topic>Applied microbiology</topic><topic>Biological and medical sciences</topic><topic>Cyanobacteria - chemistry</topic><topic>Cyanobacteria - drug effects</topic><topic>Cyanobacteria - enzymology</topic><topic>Fatty Acids - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General aspects</topic><topic>Glycolipids - isolation & purification</topic><topic>Glycolipids - pharmacology</topic><topic>Hydrolysis</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Microbiology</topic><topic>Reverse Transcriptase Inhibitors - isolation & purification</topic><topic>Reverse Transcriptase Inhibitors - pharmacology</topic><topic>Spectrometry, Mass, Fast Atom Bombardment</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reshef, Vered</creatorcontrib><creatorcontrib>Mizrachi, Erez</creatorcontrib><creatorcontrib>Maretzki, Tal</creatorcontrib><creatorcontrib>Silberstein, Colin</creatorcontrib><creatorcontrib>Loya, Shoshana</creatorcontrib><creatorcontrib>Hizi, Amnon</creatorcontrib><creatorcontrib>Carmeli, Shmuel</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of natural products (Washington, D.C.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reshef, Vered</au><au>Mizrachi, Erez</au><au>Maretzki, Tal</au><au>Silberstein, Colin</au><au>Loya, Shoshana</au><au>Hizi, Amnon</au><au>Carmeli, Shmuel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>New Acylated Sulfoglycolipids and Digalactolipids and Related Known Glycolipids from Cyanobacteria with a Potential To Inhibit the Reverse Transcriptase of HIV-1</atitle><jtitle>Journal of natural products (Washington, D.C.)</jtitle><addtitle>J. Nat. Prod</addtitle><date>1997-12-01</date><risdate>1997</risdate><volume>60</volume><issue>12</issue><spage>1251</spage><epage>1260</epage><pages>1251-1260</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><coden>JNPRDF</coden><abstract>Five novel diacylated sulfoglycolipids (1−5) were isolated from the cyanobacterium Scytonema sp. (TAU strain SL-30-1-4) and four novel acylated diglycolipids (6−9) were isolated from the cyanobacterium Oscillatoria raoi (TAU strain IL-76-1-2). These two groups of glycolipids and related known glycolipids isolated from these two and three other strains of cyanobacteria, Phormidium tenue (TAU strain IL-144-1), O. trichoides (TAU strain IL-104-3-2), and O. limnetica (TAU strain NG-4-1-2), were found to inhibit HIV-1 RT enzymatic activity to different extents. The structure elucidation of the various compounds is based on the selective hydrolysis of the glycerol ester moieties, GCMS analysis of the methyl ester derivatives of the liberated fatty acids, homo- and heteronuclear-2D-NMR techniques, and MS. The use of negative-ion FABMS for analyzing the combination and distribution of the fatty acids in glycolipids is demonstrated.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>9428159</pmid><doi>10.1021/np970327m</doi><tpages>10</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 1997-12, Vol.60 (12), p.1251-1260 |
| issn | 0163-3864 1520-6025 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | AIDS/HIV Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Biological and medical sciences Cyanobacteria - chemistry Cyanobacteria - drug effects Cyanobacteria - enzymology Fatty Acids - metabolism Fundamental and applied biological sciences. Psychology General aspects Glycolipids - isolation & purification Glycolipids - pharmacology Hydrolysis Magnetic Resonance Spectroscopy Microbiology Reverse Transcriptase Inhibitors - isolation & purification Reverse Transcriptase Inhibitors - pharmacology Spectrometry, Mass, Fast Atom Bombardment Spectrophotometry, Ultraviolet Spectroscopy, Fourier Transform Infrared |
| title | New Acylated Sulfoglycolipids and Digalactolipids and Related Known Glycolipids from Cyanobacteria with a Potential To Inhibit the Reverse Transcriptase of HIV-1 |
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