Alkaloids: Chemistry and Biology最新文献

{"title":"Cinchona Alkaloids-Derivatives and Applications.","authors":"Przemysław J Boratyński,&nbsp;Mariola Zielińska-Błajet,&nbsp;Jacek Skarżewski","doi":"10.1016/bs.alkal.2018.11.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.11.001","url":null,"abstract":"<p><p>Major Cinchona alkaloids quinine, quinidine, cinchonine, and cinchonidine are available chiral natural compounds (chiral pool). Unlike many other natural products, these alkaloids are available in multiple diastereomeric forms which are separated on an industrial scale. The introduction discusses in short conformational equilibria, traditional separation scheme, biosynthesis, and de novo chemical syntheses. The second section concerns useful chemical applications of the alkaloids as chiral recognition agents and effective chiral catalysts. Besides the Sharpless ethers and quaternary ammonium salts (chiral PTC), the most successful bifunctional organocatalysts are based on 9-amino derivatives: thioureas and squaramides. The third section reports the main transformations of Cinchona alkaloids. This covers reactions of the 9-hydroxyl group with the retention or inversion of configuration. Specific Cinchona rearrangements enlarging [2.2.2]bicycle of quinuclidine to [3.2.2] products are connected to the 9-OH substitution. The syntheses of numerous esterification and etherification products are described, including many examples of bi-Cinchona alkaloid ethers. Further derivatives comprise 9-N-substituted compounds. The amino group is introduced via an azido function with the inversion of configuration at the stereogenic center C9. The 9-epi-amino-alkaloids provide imines, amides, imides, thioureas, and squaramides. The syntheses of 9-carbon-, 9-sulfur-, and 9-selenium-substituted derivatives are discussed. Oxidation of the hydroxyl group of any alkaloid gives ketones, which can be selectively reduced, reacted with Grignard reagents, or subjected to the Corey-Chaykovsky reaction. The alkaloids were also partially degraded by splitting C4'-C9 or N1-C8 bonds. In order to immobilize Cinchona alkaloids the transformations of the 3-vinyl group were often exploited. Finally, miscellaneous functionalizations of quinuclidine, quinoline, and examples of various metal complexes of the alkaloids are considered.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"82 ","pages":"29-145"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.11.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37198964","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Contributors","authors":"","doi":"10.1016/s1099-4831(19)30007-0","DOIUrl":"https://doi.org/10.1016/s1099-4831(19)30007-0","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(19)30007-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"56576884","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Copyright","authors":"","doi":"10.1016/s1099-4831(19)30027-6","DOIUrl":"https://doi.org/10.1016/s1099-4831(19)30027-6","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"45 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(19)30027-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"56577006","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Copyright","authors":"","doi":"10.1016/s1099-4831(19)30005-7","DOIUrl":"https://doi.org/10.1016/s1099-4831(19)30005-7","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"1 1","pages":""},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(19)30005-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"56576830","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Pyrrolizidine Alkaloids.","authors":"Joaquín Tamariz,&nbsp;Eleuterio Burgueño-Tapia,&nbsp;Miguel A Vázquez,&nbsp;Francisco Delgado","doi":"10.1016/bs.alkal.2018.03.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.03.001","url":null,"abstract":"<p><p>Naturally occurring pyrrolizidine alkaloids (PAs) are isolated from plants and other sources. The interest of the scientific community in these compounds owes itself to their high toxicity and biological activity, as well as to the challenge of synthesizing their pyrrolizidine scaffold. This review encompasses a wide range of topics found in the literature from 1995 to date, including the occurrence, biosynthesis, toxicity (hepatotoxicity, genotoxicity, and tumorigenicity), biological activity, and pharmacological properties (glycosidase inhibitory activity) of these secondary metabolites. Particular attention is given to the chemistry of PAs, addressing general strategies for formal and total syntheses via amino-based substrates, pyrroles, and pyrrolidine-based derivatives.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"80 ","pages":"1-314"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.03.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40532752","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Benzoxazole Alkaloids: Occurrence, Chemistry, and Biology.","authors":"Sitaram Pal,&nbsp;Bhanu Manjunath,&nbsp;Sujit Ghorai,&nbsp;Swarnendu Sasmal","doi":"10.1016/bs.alkal.2017.12.002","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.12.002","url":null,"abstract":"<p><p>Benzoxazole alkaloids exhibit a diverse array of structures and interesting biological activities. In spite of the extensive research done on the synthesis and biology, till date there is no concise update on this class of alkaloids. This chapter summarizes the literature on benzoxazole alkaloids till March 2017, which covers their isolation, characterization, possible biosynthetic origins, biological activities, and major synthetic approaches. These alkaloids have been broadly classified in the context of their sources, namely (i) fungal origin, (ii) marine origin, and (iii) plant origin.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"79 ","pages":"71-137"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.12.002","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35842516","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Moschamine-Related Indole Alkaloids.","authors":"Chengfeng Xia,&nbsp;Xiaogang Tong","doi":"10.1016/bs.alkal.2017.12.004","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.12.004","url":null,"abstract":"<p><p>Moschamine-related alkaloids originate mainly from feruloylserotonin by cyclization or dimerization. This review provides a comprehensive overview on the achievements in the field of moschamine-related alkaloids. In the isolation part, a detailed structural characterization of moschamine-related alkaloids is followed by their spectral data. Besides the well-known antioxidative activities, other screened biological properties are also outlined. Since their isolation, different protocols have been developed to synthesize these alkaloids. The synthetic part is organized according to the different synthetic methodologies for the formation of key structural elements.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"79 ","pages":"139-189"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.12.004","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35842513","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Alkaloid Synthesis Using Organocatalysts.","authors":"Hayato Ishikawa,&nbsp;Shinya Shiomi","doi":"10.1016/bs.alkal.2017.12.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.12.001","url":null,"abstract":"<p><p>This chapter covers the literature since the advent, in the 21st century, of total syntheses of alkaloids using enantio- or diastereoselective organocatalytic reactions to construct the alkaloid scaffolds. The details of these alkaloid syntheses are described separately for each basic skeleton, including indole, indoline, oxindole, and piperidine alkaloids.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"79 ","pages":"1-70"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.12.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35842512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Preface.","authors":"Hans-Joachim Knölker","doi":"10.1016/S1099-4831(18)30008-7","DOIUrl":"https://doi.org/10.1016/S1099-4831(18)30008-7","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"79 ","pages":"ix"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1099-4831(18)30008-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35842518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Preface.","authors":"Hans-Joachim Knölker","doi":"10.1016/S1099-4831(18)30022-1","DOIUrl":"https://doi.org/10.1016/S1099-4831(18)30022-1","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"80 ","pages":"ix"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/S1099-4831(18)30022-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"40531743","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}