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Alkaloids: Chemistry and Biology最新文献

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Biosynthesis, synthetic studies, and biological activities of the jadomycin alkaloids and related analogues. jadomycin生物碱及其类似物的生物合成、合成研究及生物活性。
Alkaloids: Chemistry and Biology Pub Date : 2020-01-01 Epub Date: 2020-03-09 DOI: 10.1016/bs.alkal.2020.02.001
Charles B de Koning, Kennedy J Ngwira, Amanda L Rousseau
{"title":"Biosynthesis, synthetic studies, and biological activities of the jadomycin alkaloids and related analogues.","authors":"Charles B de Koning,&nbsp;Kennedy J Ngwira,&nbsp;Amanda L Rousseau","doi":"10.1016/bs.alkal.2020.02.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2020.02.001","url":null,"abstract":"<p><p>The jadomycins are an expanding class of compounds produced from Streptomyces venezuelae, by diverting the normal biosynthesis which provides the antibiotic chloramphenicol. In the presence of amino acids, and either by heat shock, supplementation with ethanol, or when phage SV1 is added to the culture, the formation of substituted jadomycins and benzo[b]phenanthridines can be achieved. The first part of this review provides details of intermediates involved in the biosynthesis of the jadomycins and the related benzo[b]phenanthridines. Both the jadomycins and the benzo[b]phenanthridines share biosynthetic pathways with a large class of naturally occurring compounds known as the angucyclines. The biosynthetic pathways diverge when it is postulated that an intermediate quinone, such as 3-(2-formyl-6-hydroxy-4-methylphenyl)-8-hydroxy-1,4-naphthoquinone-2-carboxylic acid is formed. The quinone then undergoes reactions with amino acids and derivatives in the culture medium to ultimately afford a library of jadomycins and a few benzo[b]phenanthridines. The second part of the review initially details synthetic efforts toward the synthesis of the naturally occurring benzo[b]phenanthridine, phenanthroviridin, and then outlines methods that have been used to assemble a selection of jadomycins. Total syntheses of jadomycin A and B, derived from l-isoleucine, are described. In addition, the synthesis of the aglycon of jadomycins M, W, S, and T is outlined. These four jadomycins were derived from l-methionine, l-tryptophan, l-serine and l-threonine respectively. As a result of these synthetic efforts, the structures of jadomycin S and T have been revised. The third part of the review describes the reported antibacterial and anticancer activities of both the jadomycins and some naturally occurring benzo[b]phenanthridines.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"84 ","pages":"125-199"},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2020.02.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37944349","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}
引用次数: 7
Recent applications of the Wittig reaction in alkaloid synthesis. Wittig反应在生物碱合成中的最新应用。
Alkaloids: Chemistry and Biology Pub Date : 2020-01-01 Epub Date: 2020-03-25 DOI: 10.1016/bs.alkal.2020.02.002
Majid M Heravi, Vahideh Zadsirjan, Hoda Hamidi, Mansoureh Daraie, Tayebeh Momeni
{"title":"Recent applications of the Wittig reaction in alkaloid synthesis.","authors":"Majid M Heravi,&nbsp;Vahideh Zadsirjan,&nbsp;Hoda Hamidi,&nbsp;Mansoureh Daraie,&nbsp;Tayebeh Momeni","doi":"10.1016/bs.alkal.2020.02.002","DOIUrl":"https://doi.org/10.1016/bs.alkal.2020.02.002","url":null,"abstract":"<p><p>The Wittig reaction is the chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (the Wittig reagent) to afford an alkene and triphenylphosphine oxide. Noteworthy, this reaction results in the synthesis of alkenes in a selective and predictable fashion. Thus, it became as one of the keystone of synthetic organic chemistry, especially in the total synthesis of natural products, where the selectivity of a reaction is paramount of importance. A literature survey disclosed the existence of vast numbers of related reports and comprehensive reviews on the applications of this important name reaction in the total synthesis of natural products. However, the aim of this chapter is to underscore, the applications of the Wittig reaction in the total synthesis of one the most important and prevalent classes of natural products, the alkaloids, especially those showing important and diverse biological activities.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"84 ","pages":"201-334"},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2020.02.002","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37944350","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}
引用次数: 5
Contributors 贡献者
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 DOI: 10.1016/s1099-4831(19)30029-x
{"title":"Contributors","authors":"","doi":"10.1016/s1099-4831(19)30029-x","DOIUrl":"https://doi.org/10.1016/s1099-4831(19)30029-x","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"33 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)30029-x","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"56577074","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}
引用次数: 0
The Chemical Synthesis and Applications of Tropane Alkaloids. Tropane生物碱的化学合成及应用。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 Epub Date: 2018-09-07 DOI: 10.1016/bs.alkal.2018.06.001
Samson Afewerki, Jia-Xin Wang, Wei-Wei Liao, Armando Córdova
{"title":"The Chemical Synthesis and Applications of Tropane Alkaloids.","authors":"Samson Afewerki,&nbsp;Jia-Xin Wang,&nbsp;Wei-Wei Liao,&nbsp;Armando Córdova","doi":"10.1016/bs.alkal.2018.06.001","DOIUrl":"https://doi.org/10.1016/bs.alkal.2018.06.001","url":null,"abstract":"<p><p>Tropanes are an important class of alkaloid natural products that are found in plants all over the world. These compounds can exhibit significant biological activity and are among the oldest known medicines. In the early 19th century, tropanes were isolated, characterized, and synthesized by notable chemical researchers. Their significant biological activities have inspired tremendous research efforts toward their synthesis and the elucidation of their pharmacological activity both in academia and in industry. In this chapter, which addresses the developments in this field since 1994, the focus is on the synthesis of these compounds, and several examples of sophisticated synthetic protocols involving both asymmetric and catalytic approaches are described. In addition, the structures of more than 100 new alkaloids are included as well as the applications and pharmacological properties of some tropane alkaloids.</p>","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"81 ","pages":"151-233"},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/bs.alkal.2018.06.001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"36944750","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}
引用次数: 18
The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. 苦参碱生物碱:分离、结构测定、生物发生、生物学评价和合成。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 Epub Date: 2018-11-15 DOI: 10.1016/bs.alkal.2018.09.001
Jeremy D Mason, Steven M Weinreb
{"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}
引用次数: 4
Alkaloids of the Lauraceae. 樟科生物碱。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 Epub Date: 2019-02-26 DOI: 10.1016/bs.alkal.2018.11.002
Maria Madalena Rocha Silva Teles, Anderson Angel Vieira Pinheiro, Celidarque Da Silva Dias, Josean Fechine Tavares, José Maria Barbosa Filho, Emidio Vasconcelos Leitão Da Cunha
{"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}
引用次数: 8
Preface. 前言。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 DOI: 10.1016/S1099-4831(19)30030-6
Hans-Joachim Knölker
{"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}
引用次数: 0
Recent Progress in the Chemistry of Pandanus Alkaloids. 熊猫类生物碱化学研究进展。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 Epub Date: 2019-02-26 DOI: 10.1016/bs.alkal.2018.12.001
Mario A Tan, Hiromitsu Takayama
{"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}
引用次数: 7
Bisbenzylisoquinoline Alkaloids. 双苄基异喹啉生物碱。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 Epub Date: 2018-09-11 DOI: 10.1016/bs.alkal.2018.07.001
Carina Weber, Till Opatz
{"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}
引用次数: 28
Preface. 前言。
Alkaloids: Chemistry and Biology Pub Date : 2019-01-01 DOI: 10.1016/S1099-4831(19)30008-2
Hans-Joachim Knölker
{"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}
引用次数: 0
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