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Lissoclibadins 4−7, Polysulfur Aromatic Alkaloids from the Indonesian Ascidian Lissoclinum cf. badium
Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2‘-N,N...
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| Published in: | Journal of natural products (Washington, D.C.) D.C.), 2007-03, Vol.70 (3), p.439-442 |
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| cited_by | cdi_FETCH-LOGICAL-a478t-b3a39f40d1eaf96dd24afbd46e1a2a1ea37338f99f2f9b34e056ee11ce7495cd3 |
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| cites | cdi_FETCH-LOGICAL-a478t-b3a39f40d1eaf96dd24afbd46e1a2a1ea37338f99f2f9b34e056ee11ce7495cd3 |
| container_end_page | 442 |
| container_issue | 3 |
| container_start_page | 439 |
| container_title | Journal of natural products (Washington, D.C.) |
| container_volume | 70 |
| creator | Nakazawa, Takahiro Xu, Jingzhon Nishikawa, Teruaki Oda, Taiko Fujita, Ayako Ukai, Kazuyo Mangindaan, Remy E. P Rotinsulu, Henki Kobayashi, Hisayoshi Namikoshi, Michio |
| description | Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2‘-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1−11 were isolated from the ascidian collected in March (wet season), while 5−11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4−7 (1−4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 μM, respectively. Compounds 1−4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae. |
| doi_str_mv | 10.1021/np060593c |
| format | article |
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P ; Rotinsulu, Henki ; Kobayashi, Hisayoshi ; Namikoshi, Michio</creator><creatorcontrib>Nakazawa, Takahiro ; Xu, Jingzhon ; Nishikawa, Teruaki ; Oda, Taiko ; Fujita, Ayako ; Ukai, Kazuyo ; Mangindaan, Remy E. P ; Rotinsulu, Henki ; Kobayashi, Hisayoshi ; Namikoshi, Michio</creatorcontrib><description>Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2‘-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1−11 were isolated from the ascidian collected in March (wet season), while 5−11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4−7 (1−4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 μM, respectively. Compounds 1−4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/np060593c</identifier><identifier>PMID: 17269824</identifier><identifier>CODEN: JNPRDF</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Alkaloids - chemistry ; Alkaloids - isolation & purification ; Alkaloids - pharmacology ; Animals ; Biological and medical sciences ; Cricetinae ; Cricetulus ; Escherichia coli ; Escherichia coli - drug effects ; General pharmacology ; Indonesia ; Lissoclinum ; Medical sciences ; Microbial Sensitivity Tests ; Molecular Structure ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; Saccharomyces cerevisiae ; Saccharomyces cerevisiae - drug effects ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; Sulfur - chemistry ; Sulfur - pharmacology ; Urochordata - chemistry</subject><ispartof>Journal of natural products (Washington, D.C.), 2007-03, Vol.70 (3), p.439-442</ispartof><rights>Copyright © 2007 American Chemical Society and American Society of Pharmacognosy</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a478t-b3a39f40d1eaf96dd24afbd46e1a2a1ea37338f99f2f9b34e056ee11ce7495cd3</citedby><cites>FETCH-LOGICAL-a478t-b3a39f40d1eaf96dd24afbd46e1a2a1ea37338f99f2f9b34e056ee11ce7495cd3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18669760$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17269824$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Nakazawa, Takahiro</creatorcontrib><creatorcontrib>Xu, Jingzhon</creatorcontrib><creatorcontrib>Nishikawa, Teruaki</creatorcontrib><creatorcontrib>Oda, Taiko</creatorcontrib><creatorcontrib>Fujita, Ayako</creatorcontrib><creatorcontrib>Ukai, Kazuyo</creatorcontrib><creatorcontrib>Mangindaan, Remy E. P</creatorcontrib><creatorcontrib>Rotinsulu, Henki</creatorcontrib><creatorcontrib>Kobayashi, Hisayoshi</creatorcontrib><creatorcontrib>Namikoshi, Michio</creatorcontrib><title>Lissoclibadins 4−7, Polysulfur Aromatic Alkaloids from the Indonesian Ascidian Lissoclinum cf. badium</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Four new polysulfur aromatic alkaloids, lissoclibadins 4 (1), 5 (2), 6 (3), and 7 (4), were isolated from the ascidian Lissoclinum cf. badium collected in Indonesia, together with seven known alkaloids, lissoclibadins 1 (5), 2 (6), and 3 (7), lissoclinotoxins E (8) and F (9), 3,4-dimethoxy-6-(2‘-N,N-dimethylaminoethyl)-5-(methylthio)benzotrithiane (10), and N,N-dimethyl-5-(methylthio)varacin (11). Compounds 1−11 were isolated from the ascidian collected in March (wet season), while 5−11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4−7 (1−4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 μM, respectively. Compounds 1−4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.</description><subject>Alkaloids - chemistry</subject><subject>Alkaloids - isolation & purification</subject><subject>Alkaloids - pharmacology</subject><subject>Animals</subject><subject>Biological and medical sciences</subject><subject>Cricetinae</subject><subject>Cricetulus</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>General pharmacology</subject><subject>Indonesia</subject><subject>Lissoclinum</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. 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Compounds 1−11 were isolated from the ascidian collected in March (wet season), while 5−11 have been obtained previously from the organism collected in September (dry season) at the same site. The structures of the new compounds were assigned on the basis of their spectroscopic data. Lissoclibadins 4−7 (1−4) inhibited the colony formation of Chinese hamster V79 cells with EC50 values of 0.71, 0.06, 0.06, and 0.17 μM, respectively. Compounds 1−4 showed also weak antimicrobial activity against Staphylococcus aureus, Escherichia coli, and Saccharomyces cerevisiae.</abstract><cop>Washington, DC</cop><cop>Glendale, AZ</cop><pub>American Chemical Society</pub><pmid>17269824</pmid><doi>10.1021/np060593c</doi><tpages>4</tpages></addata></record> |
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| identifier | ISSN: 0163-3864 |
| ispartof | Journal of natural products (Washington, D.C.), 2007-03, Vol.70 (3), p.439-442 |
| issn | 0163-3864 1520-6025 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_70308115 |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Alkaloids - chemistry Alkaloids - isolation & purification Alkaloids - pharmacology Animals Biological and medical sciences Cricetinae Cricetulus Escherichia coli Escherichia coli - drug effects General pharmacology Indonesia Lissoclinum Medical sciences Microbial Sensitivity Tests Molecular Structure Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Saccharomyces cerevisiae Saccharomyces cerevisiae - drug effects Staphylococcus aureus Staphylococcus aureus - drug effects Sulfur - chemistry Sulfur - pharmacology Urochordata - chemistry |
| title | Lissoclibadins 4−7, Polysulfur Aromatic Alkaloids from the Indonesian Ascidian Lissoclinum cf. badium |
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