{"title":"茜草根状茎中乌根素L、S、U和Z的全合成、绝对构型及细胞毒性评价","authors":"Cheng-Tin Lin, Jing-Jy Cheng, Huei-Ling You, Cheng-Hsun Hsieh, Chiao-Jou Pan, Ming-Jaw Don","doi":"10.1021/acs.jnatprod.4c01487","DOIUrl":null,"url":null,"abstract":"<p><p>This study describes the first and efficient syntheses of naturally occurring ugonins L (<b>1a</b>), S (<b>2a</b>, <b>2b</b>), U (<b>3</b>), and Z (<b>4</b>). Naturally occurring ugonin S has two stereoisomers. On the basis of their NMR and specific rotation data, the absolute configuration of <i>trans</i>-ugonin L (<b>1a</b>) was determined as 10<i>R</i>,11<i>R</i>, while the absolute configurations of <i>trans</i>-ugonin S (<b>2a</b>) and <i>cis</i>-ugonin S (<b>2b</b>) were determined to be 10<i>R</i>,11<i>R</i> and 10<i>R</i>,11<i>S</i>, respectively. The naturally occurring <i>cis</i>-ugonin U (<b>3</b>) presented the 10<i>S</i>,11<i>R</i> configuration. The naturally occurring <i>cis</i>-ugonin Z (<b>4</b>) was suggested to have a 10<i>S</i>,11<i>R</i> configuration. Four isomers of compound <b>2</b> and two isomers of compound <b>3</b> showed moderate cytotoxic activities against the CEM and H460 human cancer cell lines.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"785-796"},"PeriodicalIF":3.3000,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Total Syntheses, Absolute Configuration, and Cytotoxicity Evaluation of Ugonins L, S, U, and Z from the Rhizomes of <i>Helminthostachys zeylanica</i>.\",\"authors\":\"Cheng-Tin Lin, Jing-Jy Cheng, Huei-Ling You, Cheng-Hsun Hsieh, Chiao-Jou Pan, Ming-Jaw Don\",\"doi\":\"10.1021/acs.jnatprod.4c01487\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>This study describes the first and efficient syntheses of naturally occurring ugonins L (<b>1a</b>), S (<b>2a</b>, <b>2b</b>), U (<b>3</b>), and Z (<b>4</b>). Naturally occurring ugonin S has two stereoisomers. On the basis of their NMR and specific rotation data, the absolute configuration of <i>trans</i>-ugonin L (<b>1a</b>) was determined as 10<i>R</i>,11<i>R</i>, while the absolute configurations of <i>trans</i>-ugonin S (<b>2a</b>) and <i>cis</i>-ugonin S (<b>2b</b>) were determined to be 10<i>R</i>,11<i>R</i> and 10<i>R</i>,11<i>S</i>, respectively. The naturally occurring <i>cis</i>-ugonin U (<b>3</b>) presented the 10<i>S</i>,11<i>R</i> configuration. The naturally occurring <i>cis</i>-ugonin Z (<b>4</b>) was suggested to have a 10<i>S</i>,11<i>R</i> configuration. Four isomers of compound <b>2</b> and two isomers of compound <b>3</b> showed moderate cytotoxic activities against the CEM and H460 human cancer cell lines.</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":\" \",\"pages\":\"785-796\"},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2025-03-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Natural Products \",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.jnatprod.4c01487\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/3/13 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://doi.org/10.1021/acs.jnatprod.4c01487","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/13 0:00:00","PubModel":"Epub","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
摘要
本研究首次高效合成了天然存在的乌根素L （1a）、S （2a、2b）、U(3)和Z(4)。天然存在的乌根素S有两种立体异构体。根据它们的核磁共振和比旋数据，确定trans-ugonin L （1a）的绝对构型为10R、11R，而trans-ugonin S （2a）和顺式ugonin S （2b）的绝对构型分别为10R、11R和顺式ugonin S （2b）的绝对构型为10R、11R和10R、11S。自然产生的顺式乌根蛋白U(3)呈10S，11R构型。自然产生的顺式ugonin Z(4)被认为具有10S，11R构型。化合物2的4个同分异构体和化合物3的2个同分异构体对CEM和H460人癌细胞表现出中等的细胞毒活性。
Total Syntheses, Absolute Configuration, and Cytotoxicity Evaluation of Ugonins L, S, U, and Z from the Rhizomes of Helminthostachys zeylanica.
This study describes the first and efficient syntheses of naturally occurring ugonins L (1a), S (2a, 2b), U (3), and Z (4). Naturally occurring ugonin S has two stereoisomers. On the basis of their NMR and specific rotation data, the absolute configuration of trans-ugonin L (1a) was determined as 10R,11R, while the absolute configurations of trans-ugonin S (2a) and cis-ugonin S (2b) were determined to be 10R,11R and 10R,11S, respectively. The naturally occurring cis-ugonin U (3) presented the 10S,11R configuration. The naturally occurring cis-ugonin Z (4) was suggested to have a 10S,11R configuration. Four isomers of compound 2 and two isomers of compound 3 showed moderate cytotoxic activities against the CEM and H460 human cancer cell lines.
期刊介绍：
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
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