{"title":"岛青霉双蒽醌修饰物红霉素的氧化还原反应及生物转化研究。","authors":"S Mori, K Kawai, Y Nozawa, Y Ogihara","doi":"10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7","DOIUrl":null,"url":null,"abstract":"Rubroskyrin, a modified bis-anthraquinone pigment from Penicillium islandicum Sopp, was studied on the redox interaction with NADH-linked redox system of rat liver microsomes, comparing with luteoskyrin and rugulosin. It was found that rubroskyrin was enzymatically reduced by NADH/microsomes and was immediately autoxidized by dissolved oxygen, producing hydrogen peroxide (H2O2). Luteoskyrin and rugulosin did not exhibit such a redox reaction, consuming dissolved oxygen and producing H2O2. The H2O2 production was significantly accelerated by superoxide dismutase (SOD), suggesting the production of superoxide anion during the reduction-autoxidation cycles of rubroskyrin. The thin layer chromatographic (TLC) and spectrophotometric analyses revealed that rubroskyrin was biotransformed by the NADH/microsomes system to stable product(s) which was no longer enzymatically reduced by the NADH/microsome system. From these results it was speculated that the mutagenicity of rubroskyrin might result from the generation of active oxygen by the NADH/microsome-catalyzed redox reaction, and that the redox reaction-linked biotransformation might lead to the elimination of cytotoxicity of rubroskyrin, showing significantly less toxicity than those of luteoskyrin and rugulosin in vivo.","PeriodicalId":18777,"journal":{"name":"Natural toxins","volume":"6 2","pages":"85-90"},"PeriodicalIF":0.0000,"publicationDate":"1998-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7","citationCount":"3","resultStr":"{\"title\":\"The redox reaction and biotransformation of rubroskyrin, a modified bis-anthraquione from Penicillium islandicum Sopp.\",\"authors\":\"S Mori, K Kawai, Y Nozawa, Y Ogihara\",\"doi\":\"10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Rubroskyrin, a modified bis-anthraquinone pigment from Penicillium islandicum Sopp, was studied on the redox interaction with NADH-linked redox system of rat liver microsomes, comparing with luteoskyrin and rugulosin. It was found that rubroskyrin was enzymatically reduced by NADH/microsomes and was immediately autoxidized by dissolved oxygen, producing hydrogen peroxide (H2O2). Luteoskyrin and rugulosin did not exhibit such a redox reaction, consuming dissolved oxygen and producing H2O2. The H2O2 production was significantly accelerated by superoxide dismutase (SOD), suggesting the production of superoxide anion during the reduction-autoxidation cycles of rubroskyrin. The thin layer chromatographic (TLC) and spectrophotometric analyses revealed that rubroskyrin was biotransformed by the NADH/microsomes system to stable product(s) which was no longer enzymatically reduced by the NADH/microsome system. From these results it was speculated that the mutagenicity of rubroskyrin might result from the generation of active oxygen by the NADH/microsome-catalyzed redox reaction, and that the redox reaction-linked biotransformation might lead to the elimination of cytotoxicity of rubroskyrin, showing significantly less toxicity than those of luteoskyrin and rugulosin in vivo.\",\"PeriodicalId\":18777,\"journal\":{\"name\":\"Natural toxins\",\"volume\":\"6 2\",\"pages\":\"85-90\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"1998-01-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7\",\"citationCount\":\"3\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural toxins\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural toxins","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/(sici)1522-7189(199804)6:2<85::aid-nt19>3.0.co;2-7","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
The redox reaction and biotransformation of rubroskyrin, a modified bis-anthraquione from Penicillium islandicum Sopp.
Rubroskyrin, a modified bis-anthraquinone pigment from Penicillium islandicum Sopp, was studied on the redox interaction with NADH-linked redox system of rat liver microsomes, comparing with luteoskyrin and rugulosin. It was found that rubroskyrin was enzymatically reduced by NADH/microsomes and was immediately autoxidized by dissolved oxygen, producing hydrogen peroxide (H2O2). Luteoskyrin and rugulosin did not exhibit such a redox reaction, consuming dissolved oxygen and producing H2O2. The H2O2 production was significantly accelerated by superoxide dismutase (SOD), suggesting the production of superoxide anion during the reduction-autoxidation cycles of rubroskyrin. The thin layer chromatographic (TLC) and spectrophotometric analyses revealed that rubroskyrin was biotransformed by the NADH/microsomes system to stable product(s) which was no longer enzymatically reduced by the NADH/microsome system. From these results it was speculated that the mutagenicity of rubroskyrin might result from the generation of active oxygen by the NADH/microsome-catalyzed redox reaction, and that the redox reaction-linked biotransformation might lead to the elimination of cytotoxicity of rubroskyrin, showing significantly less toxicity than those of luteoskyrin and rugulosin in vivo.