Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp
A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C 26 H 33 NO 7 , was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and...
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| Veröffentlicht in: | Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2004-01, Vol.68 (1), p.104-111 |
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| container_title | Bioscience, biotechnology, and biochemistry |
| container_volume | 68 |
| creator | KOMODA, Toshikazu YOSHIDA, Kayo ABE, Naoki SUGIYAMA, Yasumasa IMACHI, Misako HIROTA, Hiroshi KOSHINO, Hiroyuki HIROTA, Akira |
| description | A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C
26
H
33
NO
7
, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a β-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the
1
H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM. |
| doi_str_mv | 10.1271/bbb.68.104 |
| format | Article |
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26
H
33
NO
7
, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a β-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the
1
H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM.</description><identifier>ISSN: 0916-8451</identifier><identifier>EISSN: 1347-6947</identifier><identifier>DOI: 10.1271/bbb.68.104</identifier><language>eng</language><publisher>Tokyo: Japan Society for Bioscience, Biotechnology, and Agrochemistry</publisher><subject>Biological and medical sciences ; Fundamental and applied biological sciences. Psychology ; soybean lipoxygenase inhibitor ; Streptomyces</subject><ispartof>Bioscience, biotechnology, and biochemistry, 2004-01, Vol.68 (1), p.104-111</ispartof><rights>2004 by Japan Society for Bioscience, Biotechnology, and Agrochemistry 2004</rights><rights>2004 INIST-CNRS</rights><rights>Copyright Japan Science and Technology Agency 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c490t-dd85be345b8d0251462653271c856d2345ef6afad06eeeccbdfc1b7b30bb2a4e3</citedby><cites>FETCH-LOGICAL-c490t-dd85be345b8d0251462653271c856d2345ef6afad06eeeccbdfc1b7b30bb2a4e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,4022,27921,27922,27923</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=15789007$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>KOMODA, Toshikazu</creatorcontrib><creatorcontrib>YOSHIDA, Kayo</creatorcontrib><creatorcontrib>ABE, Naoki</creatorcontrib><creatorcontrib>SUGIYAMA, Yasumasa</creatorcontrib><creatorcontrib>IMACHI, Misako</creatorcontrib><creatorcontrib>HIROTA, Hiroshi</creatorcontrib><creatorcontrib>KOSHINO, Hiroyuki</creatorcontrib><creatorcontrib>HIROTA, Akira</creatorcontrib><title>Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp</title><title>Bioscience, biotechnology, and biochemistry</title><description>A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C
26
H
33
NO
7
, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a β-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the
1
H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM.</description><subject>Biological and medical sciences</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>soybean lipoxygenase inhibitor</subject><subject>Streptomyces</subject><issn>0916-8451</issn><issn>1347-6947</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><recordid>eNptkF9LwzAUxYMoOKcvfoKC6IPYmbRJmj7K8M9g6IPzOSTprXa0TU0ydd_ejE0E8ely7_2dw-EgdErwhGQFudZaT7iYEEz30IjktEh5SYt9NMIl4amgjByiI--XGMcDIyM0XUBwaoCgWttDcnOVqOTRfkCbzJvBfq1fofeQzPq3RjfBuqR2tkueg4Mh2G5twCd-OEYHtWo9nOzmGL3c3S6mD-n86X42vZmnhpY4pFUlmIacMi0qnDFCecZZHlMbwXiVxQfUXNWqwhwAjNFVbYgudI61zhSFfIwutr6Ds-8r8EF2jTfQtqoHu_KSFCKjIs8jePYHXNqV62M2SSgtBS4yTiN1uaWMs947qOXgmk65tSRYbtqUsU3JRVw38PnOUnmj2tqp3jT-V8EKUWJcRI5tuaavrevUp3VtJYNat9b9iPJ__L8BP36Gpw</recordid><startdate>20040101</startdate><enddate>20040101</enddate><creator>KOMODA, Toshikazu</creator><creator>YOSHIDA, Kayo</creator><creator>ABE, Naoki</creator><creator>SUGIYAMA, Yasumasa</creator><creator>IMACHI, Misako</creator><creator>HIROTA, Hiroshi</creator><creator>KOSHINO, Hiroyuki</creator><creator>HIROTA, Akira</creator><general>Japan Society for Bioscience, Biotechnology, and Agrochemistry</general><general>Japan Society for Bioscience Biotechnology and Agrochemistry</general><general>Oxford University Press</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>C1K</scope></search><sort><creationdate>20040101</creationdate><title>Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp</title><author>KOMODA, Toshikazu ; YOSHIDA, Kayo ; ABE, Naoki ; SUGIYAMA, Yasumasa ; IMACHI, Misako ; HIROTA, Hiroshi ; KOSHINO, Hiroyuki ; HIROTA, Akira</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c490t-dd85be345b8d0251462653271c856d2345ef6afad06eeeccbdfc1b7b30bb2a4e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Biological and medical sciences</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>soybean lipoxygenase inhibitor</topic><topic>Streptomyces</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>KOMODA, Toshikazu</creatorcontrib><creatorcontrib>YOSHIDA, Kayo</creatorcontrib><creatorcontrib>ABE, Naoki</creatorcontrib><creatorcontrib>SUGIYAMA, Yasumasa</creatorcontrib><creatorcontrib>IMACHI, Misako</creatorcontrib><creatorcontrib>HIROTA, Hiroshi</creatorcontrib><creatorcontrib>KOSHINO, Hiroyuki</creatorcontrib><creatorcontrib>HIROTA, Akira</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Bacteriology Abstracts (Microbiology B)</collection><collection>Environmental Sciences and Pollution Management</collection><jtitle>Bioscience, biotechnology, and biochemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>KOMODA, Toshikazu</au><au>YOSHIDA, Kayo</au><au>ABE, Naoki</au><au>SUGIYAMA, Yasumasa</au><au>IMACHI, Misako</au><au>HIROTA, Hiroshi</au><au>KOSHINO, Hiroyuki</au><au>HIROTA, Akira</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp</atitle><jtitle>Bioscience, biotechnology, and biochemistry</jtitle><date>2004-01-01</date><risdate>2004</risdate><volume>68</volume><issue>1</issue><spage>104</spage><epage>111</epage><pages>104-111</pages><issn>0916-8451</issn><eissn>1347-6947</eissn><abstract>A simple new assay was designed for lipoxygenase inhibitors. This assay was used to find the novel lipoxygenase inhibitor, tetrapetalone A (1). Tetrapetalone A (1), C
26
H
33
NO
7
, was isolated from Streptomyces sp. USF-4727 strain. Its planar structure was determined by spectroscopic evidence and by methylating with diazomethane to show the presence of a novel tetracyclic skeleton and a β-D-rhodinosyl moiety. The stereochemistry of 1 was investigated by the coupling constant in the
1
H-NMR spectrum, NOE correlations, modified Mosher's method and derivation. We have reported the structural elucidation of 1 in our previous paper. However, further investigation gave another structure for 1, which is described in this paper. Tetrapetalone A showed similar inhibitory activity against soybean lipoxygenase to the two well-known lipoxygenase inhibitors, kojic acid and NDGA, while methylated tetrapetalone A (2) showed little inhibitory activity, even at a concentration of 1 mM.</abstract><cop>Tokyo</cop><pub>Japan Society for Bioscience, Biotechnology, and Agrochemistry</pub><doi>10.1271/bbb.68.104</doi><tpages>8</tpages></addata></record> |
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| ispartof | Bioscience, biotechnology, and biochemistry, 2004-01, Vol.68 (1), p.104-111 |
| issn | 0916-8451 1347-6947 |
| language | eng |
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| source | J-STAGE Free; Oxford University Press Journals All Titles (1996-Current); Freely Accessible Japanese Titles; EZB-FREE-00999 freely available EZB journals; Free Full-Text Journals in Chemistry |
| subjects | Biological and medical sciences Fundamental and applied biological sciences. Psychology soybean lipoxygenase inhibitor Streptomyces |
| title | Tetrapetalone A, a Novel Lipoxygense Inhibitor from Streptomyces sp |
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