Alkaloids: Chemistry and Biology最新文献

{"title":"The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis.","authors":"Jeremy D Mason,&nbsp;Steven M Weinreb","doi":"10.1016/bs.alkal.2018.09.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.09.001","url":null,"abstract":"<p><p>The alstoscholarisines are a small family of biologically and structurally interesting polycyclic monoterpenoid indole alkaloids isolated from the leaf extracts of Alstonia scholaris. The alkaloids can be divided into three different subtypes based upon their structures and putative biogenesis: (1) (-)-alstoscholarisines A-E, (2) (+)-alstoscholarisine G, and (3) (+)-alstoscholarisines H-J. This review discusses the isolation, structure determination, biological activity, and proposed biosynthesis of these metabolites. In addition, synthetic studies on the alkaloids are described including total syntheses of racemic alstoscholarisines A-E, a total synthesis of (-)-alstoscholarisine A, and a synthesis of racemic alstoscholarisine H.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"81 ","pages":"115-150"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.09.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36944749","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":"Alkaloids of the Lauraceae.","authors":"Maria Madalena Rocha Silva Teles,&nbsp;Anderson Angel Vieira Pinheiro,&nbsp;Celidarque Da Silva Dias,&nbsp;Josean Fechine Tavares,&nbsp;José Maria Barbosa Filho,&nbsp;Emidio Vasconcelos Leitão Da Cunha","doi":"10.1016/bs.alkal.2018.11.002","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.11.002","url":null,"abstract":"<p><p>This chapter presents an overview of the chemistry and pharmacology of the alkaloids found in species of the Lauraceae family. The occurrence of alkaloids from Lauraceae species as well as their chemical structures is summarized in informative and easy-to-understand tables. Within the Lauraceae family, the genera Ocotea (195), Litsea (180), Cryptocarya (133), and Neolitsea (110) have led to the greater number of publications regarding alkaloids content. Valuable and comprehensive information about the structure of these alkaloids is provided. The alkaloids of the aporphine type, found in 22 of the 23 genera, represent the predominant group in this family. Many of the isolated alkaloids exhibit unique structures. From plants of this family, 22 different types of skeletons have been isolated, among them only the purine alkaloids are classified as pseudoalkaloids, and the types phenethylamines, phenethylcinnamides, and phthalidoisoquinoline are classified as protoalkaloids. The chapter is presented as a contribution for the scientific community, mainly to enable the search for alkaloids in species belonging to the Lauraceae family.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"82 ","pages":"147-304"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.11.002","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37037933","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":"Recent Progress in the Chemistry of Pandanus Alkaloids.","authors":"Mario A Tan,&nbsp;Hiromitsu Takayama","doi":"10.1016/bs.alkal.2018.12.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.12.001","url":null,"abstract":"<p><p>The genus Pandanus (Pandanaceae) is widely distributed in the tropical and subtropical regions. With about 700 species worldwide, three Pandanus species (P. amaryllifolius, P. utilis, and P. dubius) have been investigated and found to contain new alkaloids possessing a pyrrolidinyl-α,β-unsaturated γ-lactone, a γ-butylidene-α-methyl-α,β-unsaturated γ-lactam, and/or indolizidine residues. Several total syntheses of Pandanus alkaloids have been accomplished. Several pharmacological studies on Pandanus species, including scientific validations of their antibacterial, antiinflammatory, antidiarrheal, and cytotoxic activities, have been conducted in relation to their traditional folk medicine uses.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"82 ","pages":"1-28"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.12.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37037931","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(19)30030-6","DOIUrl":"https://doi.org/10.1016/S1099-4831(19)30030-6","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"82 ","pages":"ix"},"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)30030-6","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37198969","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":"Bisbenzylisoquinoline Alkaloids.","authors":"Carina Weber,&nbsp;Till Opatz","doi":"10.1016/bs.alkal.2018.07.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.07.001","url":null,"abstract":"<p><p>The present review covers the literature on bisbenzylisoquinoline alkaloids from 1999 through early 2018. About 500 natural products belong to this large alkaloid class, of which 65 were characterized for the first time in the period covered by this chapter. The review comprises a classification of bisbenzylisoquinoline alkaloids and gives an overview of the principal biosynthetic pathways. Furthermore, a list of the novel natural products as well as their available analytical data are included in this chapter. Special emphasis is given to the progress in the total synthesis of bisbenzylisoquinoline alkaloids. To accommodate the drastically increased number of publications concerning the biological and pharmacological evaluation, an overview on the most important biological findings is provided.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"81 ","pages":"1-114"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.07.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36889044","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(19)30008-2","DOIUrl":"https://doi.org/10.1016/S1099-4831(19)30008-2","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"81 ","pages":"ix-x"},"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)30008-2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36944752","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":"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}