Joaquín Tamariz, Eleuterio Burgueño-Tapia, Miguel A Vázquez, Francisco Delgado
{"title":"Pyrrolizidine Alkaloids.","authors":"Joaquín Tamariz, Eleuterio Burgueño-Tapia, Miguel A Vázquez, 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, Bhanu Manjunath, Sujit Ghorai, 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, 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, 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}
Aletta E van der Westhuyzen, Liliya V Frolova, Alexander Kornienko, Willem A L van Otterlo
{"title":"The Rigidins: Isolation, Bioactivity, and Total Synthesis-Novel Pyrrolo[2,3-d]Pyrimidine Analogues Using Multicomponent Reactions.","authors":"Aletta E van der Westhuyzen, Liliya V Frolova, Alexander Kornienko, Willem A L van Otterlo","doi":"10.1016/bs.alkal.2017.12.003","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.12.003","url":null,"abstract":"<p><p>Rigidins (2-6) are pyrrolopyrimidine alkaloids isolated from marine tunicates. Since their isolation, refinement of their total syntheses, and biochemical evaluation, interest toward this pyrrolo[2,3-d]pyrimidine scaffold as a medicinal candidate has been triggered. The derivatization of these natural products has led to the discovery of a novel range of 7-deazahypoxanthines, which exhibit extremely potent anticancer activity in human cancer cell lines. A major breakthrough toward the synthesis of rigidin and various rigidin analogues has been the application of multicomponent reactions (MCRs). The rapid assembly of molecular diversity and flexibility displayed by MCRs makes it an attractive strategy for the preparation of rigidin-inspired small molecules. Furthermore, a number of rigidin-like 7-deazaxanthine compounds have been reported in the literature and the popularity of implementing MCRs to construct these 7-deazaxanthines is highlighted here. It is our hope that the synthetic methods described in this chapter will result in the further generation of rigidin-inspired compounds that will move on from being \"hits\" into \"leads\" in the medicinal chemistry drug discovery pipeline and potentially into anticancer therapeutics.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"79 ","pages":"191-220"},"PeriodicalIF":0.0,"publicationDate":"2018-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.12.003","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35842517","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":"Galbulimima Alkaloids.","authors":"Uwe Rinner","doi":"10.1016/bs.alkal.2017.05.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.05.001","url":null,"abstract":"<p><p>This chapter provides a comprehensive overview of recent achievements in the area of Galbulimima alkaloids. Following a discussion of the isolation of Galbulimima alkaloids and structural features of members of this fascinating family of secondary metabolites, biological properties of selected compounds are briefly discussed. Furthermore, the proposed biosynthetic routes toward Galbulimima alkaloids are outlined. The main section of the chapter is devoted to a detailed discussion and comparison of all total syntheses of Galbulimima alkaloids published to date.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":" ","pages":"109-166"},"PeriodicalIF":0.0,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.05.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35297329","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":"Acridone Alkaloids.","authors":"Joseph P Michael","doi":"10.1016/bs.alkal.2017.06.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.06.001","url":null,"abstract":"<p><p>There have been substantial developments in the chemistry and biology of the acridone alkaloids in the 16years since the topic was last reviewed in this series of monographs (2000). The present survey covers the literature from mid-1999 to 2016. A brief overview of the biosynthesis of acridone alkaloids is followed by details of the occurrence and characterization of known alkaloids from new sources, and of novel alkaloids. The classes covered include simple acridone alkaloids, C-prenylacridones, furo[3,2-b]- and furo[2,3-c]acridones, pyrano[3,2-b]- and pyrano[2,3-c]acridones, and dimeric alkaloids containing acridone moieties. Syntheses of acridone alkaloids and certain analogs reported during the review period are comprehensively covered. The final section summarizes aspects of their bioactivity, including cytotoxicity and anticancer activity, antimicrobial and antiparasitic properties, and enzyme inhibition. The chapter concludes with a brief description of important bioactive synthetic analogs.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":" ","pages":"1-108"},"PeriodicalIF":0.0,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.06.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35343270","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":"Total Synthesis of Lundurine and Related Alkaloids: Synthetic Approaches and Strategies.","authors":"Shigeru Arai, Masaya Nakajima, Atsushi Nishida","doi":"10.1016/bs.alkal.2017.01.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2017.01.001","url":null,"abstract":"<p><p>This review focuses on the total synthesis of lundurines A-C. Their main structural feature is a unique cyclopropa[b]indole core that has been found only in these alkaloids. In addition to this characteristic structure, the biological activity makes them as attractive synthetic targets. However, almost two decades passed from their isolation and structural determination in 1995 to their first total synthesis. The first part of this review summarizes the synthetic approaches to the tri- and tetracyclic ring systems of lundurine as well as an inter- and intramolecular cyclopropanation strategy that gives the cyclopropa[b]indole core. The second part presents a detailed description of four total syntheses that were reported from 2014 to 2016. In addition, the asymmetric total synthesis of the related alkaloids grandilodine C and lapidilectine B is described.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":" ","pages":"167-204"},"PeriodicalIF":0.0,"publicationDate":"2017-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2017.01.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"35297331","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}