{"title":"The diterpenoid alkaloids.","authors":"Xiao-Yu Liu, Bo-Wen Ke, Yong Qin, Feng-Peng Wang","doi":"10.1016/bs.alkal.2021.08.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2021.08.001","url":null,"abstract":"<p><p>The diterpenoid alkaloids are a family of extremely important natural products that have long been a research hotspot due to their myriad of intricate structures and diverse biological properties. This chapter systematically summarizes the past 11 years (2009-2019) of studies on the diterpenoid alkaloids, including the \"so-called\" atypical ones, covering the classification and biogenetic relationships, phytochemistry together with 444 new alkaloids covering 32 novel skeletons and the corrected structures, chemical reactions including conversion toward toxoids, synthetic studies, as well as biological activities. It should be noted that the synthetic studies, especially the total syntheses of various diterpenoid alkaloids, are for the first time reviewed in this treatise. This chapter, in combination with our four previous reviews in volumes 42, 59, 67, and 69, will present to the readers a more completed and updated profile of the diterpenoid alkaloids.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"87 ","pages":"1-360"},"PeriodicalIF":0.0,"publicationDate":"2022-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"39927151","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":"The chemistry of Daphniphyllum alkaloids.","authors":"Jiaxin Zhong, Hui Wang, Quan Zhang, Shuanhu Gao","doi":"10.1016/bs.alkal.2021.01.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2021.01.001","url":null,"abstract":"<p><p>The triterpenoids Daphniphyllum alkaloids share the unique fused hexacyclic ring framework are isolated from the genus Daphniphyllum. These natural products possess comprehensive biological activities and exhibit excellent potential medicinal appliment. This review covers the reported isolation studies and biological activities of Daphniphyllum alkaloids spanning the period from 1966 to the beginning of 2020, In the meantime, the total synthesis of Daphniphyllum alkaloids will be emphatically summarized for supplement over this review series.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"85 ","pages":"113-176"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2021.01.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25430902","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":"Morphine alkaloids: History, biology, and synthesis.","authors":"Christopher Wicks, Tomas Hudlicky, Uwe Rinner","doi":"10.1016/bs.alkal.2021.04.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2021.04.001","url":null,"abstract":"<p><p>This chapter provides a short overview of the history of morphine since it's isolation by Sertürner in 1805. The biosynthesis of the title alkaloid as well as all total and formal syntheses of morphine and codeine published after 1996 are discussed in detail. The last section of this chapter provides a detailed overview of medicinally relevant derivatives of the title alkaloid.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"86 ","pages":"145-342"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"39450729","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":"Chemistry of the chippiine/dippinine/tronocarpine class of indole alkaloids.","authors":"Steven C Taylor, Steven M Weinreb","doi":"10.1016/bs.alkal.2020.07.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2020.07.001","url":null,"abstract":"<p><p>The chippiines/dippinines/tronocarpine are a family of biologically and structurally interesting polycyclic tryptamine-derived indole alkaloids isolated from the leaf and bark extracts of plants belonging to the Tabernaemontana genus. To date, 14 members of this family have been isolated and characterized. 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 approaches to tronocarpine and dippinine B core intermediates and total syntheses of (+)-dippinine B and (+)-tronocarpine.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"85 ","pages":"177-222"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2020.07.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25430903","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":"Aspidosperma and Strychnos alkaloids: Chemistry and biology.","authors":"Senzhi Zhao, Gopal Sirasani, Rodrigo B Andrade","doi":"10.1016/bs.alkal.2021.05.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2021.05.001","url":null,"abstract":"<p><p>Of Nature's nearly 3000 unique monoterpene indole alkaloids derived from tryptophan, those members belonging to the Aspidosperma and Strychnos families continue to impact the fields of natural products (i.e., isolation, structure determination, biosynthesis) and organic chemistry (i.e., chemical synthesis, methodology development) among others. This review covers the biological activity (Section 2), biosynthesis (Section 3), and synthesis of both classical and novel Aspidosperma (Section 4), Strychnos (Section 5), and selected bis-indole (Section 6) alkaloids. Technological advancements in genetic sequencing and bioinformatics have deepened our understanding of how Nature assembles these intriguing molecules. The proliferation of innovative synthetic strategies and tactics for the synthesis of the alkaloids covered in this review, which include contributions from over fifty research groups from around the world, are a testament to the creative power and technical skills of synthetic organic chemists. To be sure, Nature-the Supreme molecular architect and source of a dazzling array of irresistible chemical logic puzzles-continues to inspire scientists across multiple disciplines and will certainly continue to do so for the foreseeable future.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"86 ","pages":"1-143"},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"39450728","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}