Alkaloids: Chemistry and Biology最新文献_第7页

Lycopodium alkaloids--synthetic highlights and recent developments. 石蒜生物碱——合成重点和最新进展。

Alkaloids: Chemistry and Biology Pub Date : 2013-01-01 DOI: 10.1016/b978-0-12-407774-4.00001-7

Peter Siengalewicz, Johann Mulzer, Uwe Rinner

引用次数: 34

Cephalostatins and ritterazines. 头孢他汀和瑞特拉嗪。

Alkaloids: Chemistry and Biology Pub Date : 2013-01-01 DOI: 10.1016/b978-0-12-407774-4.00002-9

Martín A Iglesias-Arteaga, Jacek W Morzycki

{"title":"Cephalostatins and ritterazines.","authors":"Martín A Iglesias-Arteaga, Jacek W Morzycki","doi":"10.1016/b978-0-12-407774-4.00002-9","DOIUrl":"https://doi.org/10.1016/b978-0-12-407774-4.00002-9","url":null,"abstract":"This review article is a tribute to the numerous chemists whose relentless effort for the last quarter of a century resulted in the isolation, identification, and finally the chemical synthesis of a family of bis-steroidal pyrazine alkaloids of marine origin. In the task of defeating cancer, the search for bioactive substances among the naturally occurring compounds is, without any doubt, a preferential approach. The remarkable contribution of Petitt, Fusetani, and their coworkers allowed to discover this family of marine alkaloids that emerge as potential therapeutic anticancer agents, although there is still a long way to go. The challenging and dangerous task of collecting living organisms from deep-waters was followed by a laborious isolation, elucidation of the complicated structures and biological tests. The outcome of this paramount effort was the identification of 45 compounds that stand, to date, as some of the most potent anticancer agents. The intriguing structures of the isolated alkaloids drew the attention of synthetic chemists, valiant enough to undertake the challenging task of synthesizing some of the most active members of the family. Fuchs, Heathcock, Winterfeldt, Suarez, Shair, and their associates pioneered in the establishment of feasible synthetic routes for the preparation of some of the naturally occurring compounds and a large number of synthetic analogs, allowing to establish SAR criteria that have guided the design of new synthetic analogs. Numerous analogs have been prepared to investigate the mechanism of action of bis-steroidal pyrazines, e.g. cephalostatin analogs bearing a strained spiroketal moiety. However, the mechanism of action and the biological target of these compounds remain far from being understood. Therefore, the rational design of simpler, yet highly active analogs seems at the current stage elusive. It is still 1 to clear why these compounds need to be dimeric to show high biological activity. Furthermore, it is not known whether the central pyrazine ring is simply a linker or has some additional function. This could be tested by examining the biological activity of steroidal dimers with other linkers, e.g. with a benzene ring. Such analogs have been actually prepared but without functional groups necessary for biological activity. The clinical trials of cephalostatins have got stuck due to a shortage of material. There is an urgent need to provide highly active, yet not too complex analogs, which could be available in substantial amounts for advanced pharmacological studies.","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"72 ","pages":"153-279"},"PeriodicalIF":0.0,"publicationDate":"2013-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/b978-0-12-407774-4.00002-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"32245037","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: 29

Polyhalogenated alkaloids in environmental and food samples. 环境和食品样品中的多卤化生物碱。

Alkaloids: Chemistry and Biology Pub Date : 2012-01-01 DOI: 10.1016/b978-0-12-398282-7.00003-5

Walter Vetter

引用次数: 12

Biosynthesis of halogenated alkaloids. 卤化生物碱的生物合成。

Alkaloids: Chemistry and Biology Pub Date : 2012-01-01 DOI: 10.1016/b978-0-12-398282-7.00002-3

Karl-Heinz van Pée

引用次数: 1

Occurrence of halogenated alkaloids. 卤化生物碱的出现。

Alkaloids: Chemistry and Biology Pub Date : 2012-01-01 DOI: 10.1016/b978-0-12-398282-7.00001-1

Gordon W Gribble

{"title":"Occurrence of halogenated alkaloids.","authors":"Gordon W Gribble","doi":"10.1016/b978-0-12-398282-7.00001-1","DOIUrl":"https://doi.org/10.1016/b978-0-12-398282-7.00001-1","url":null,"abstract":"Once considered to be isolation artifacts or chemical \"mistakes\" of nature, the number of naturally occurring organohalogen compounds has grown from a dozen in 1954 to >5000 today. Of these, at least 25% are halogenated alkaloids. This is not surprising since nitrogen-containing pyrroles, indoles, carbolines, tryptamines, tyrosines, and tyramines are excellent platforms for biohalogenation, particularly in the marine environment where both chloride and bromide are plentiful for biooxidation and subsequent incorporation into these electron-rich substrates. This review presents the occurrence of all halogenated alkaloids, with the exception of marine bromotyrosines where coverage begins where it left off in volume 61 of The Alkaloids. Whereas the biological activity of these extraordinary compounds is briefly cited for some examples, a future volume of The Alkaloids will present full coverage of this topic and will also include selected syntheses of halogenated alkaloids. Natural organohalogens of all types, especially marine and terrestrial halogenated alkaloids, comprise a rapidly expanding class of natural products, in many cases expressing powerful biological activity. This enormous proliferation has several origins: (1) a revitalization of natural product research in a search for new drugs, (2) improved compound characterization methods (multidimensional NMR, high-resolution mass spectrometry), (3) specific enzyme-based and other biological assays, (4) sophisticated collection methods (SCUBA and remote submersibles for deep ocean marine collections), (5) new separation and purification techniques (HPLC and countercurrent separation), (6) a greater appreciation of traditional folk medicine and ethobotany, and (7) marine bacteria and fungi as novel sources of natural products. Halogenated alkaloids are truly omnipresent in the environment. Indeed, one compound, Q1 (234), is ubiquitous in the marine food web and is found in the Inuit from their diet of whale blubber. Given the fact that of the 500,000 estimated marine organisms--which are the source of most halogenated alkaloids--only a small percentage have been investigated for their chemical content, it is certain that myriad new halogenated alkaloids are awaiting discovery. For example, it is estimated that nearly 4000 species of bryozoans have not been examined for their chemical content. The few species that have been studied contain some extraordinary halogenated alkaloids, such as hinckdentine A (610) and the chartellines (611-613). Of the estimated 1.5 million species of fungi, secondary metabolites have been characterized from only 5000 species. The future seems bright for the collector of halogenated alkaloids!","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"71 ","pages":"1-165"},"PeriodicalIF":0.0,"publicationDate":"2012-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/b978-0-12-398282-7.00001-1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"31080085","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: 43

The cylindrospermopsin alkaloids. 柱状精子素生物碱。

Alkaloids: Chemistry and Biology Pub Date : 2011-01-01 DOI: 10.1016/b978-0-12-391426-2.00001-3

Daniel M Evans, Patrick J Murphy

引用次数: 3

The pyrrolo[2,1-a]isoquinoline alkaloids. pyrrolo[2.1 -a]同位素生物碱。

Alkaloids: Chemistry and Biology Pub Date : 2011-01-01 DOI: 10.1016/b978-0-12-391426-2.00002-5

Ulrike Pässler, Hans-Joachim Knölker

引用次数: 20

Alkaloids from the genus Duguetia. 杜鹃属生物碱。

Alkaloids: Chemistry and Biology Pub Date : 2010-01-01 DOI: 10.1016/s1099-4831(10)06803-3

Edwin G Pérez, Bruce K Cassels

引用次数: 18

Galanthamine production by Leucojum aestivum cultures in vitro. 白姜体外培养产加兰他敏的研究。

Alkaloids: Chemistry and Biology Pub Date : 2010-01-01 DOI: 10.1016/s1099-4831(10)06805-7

Marina I Stanilova, Emil D Molle, Stanislav G Yanev

{"title":"Galanthamine production by Leucojum aestivum cultures in vitro.","authors":"Marina I Stanilova, Emil D Molle, Stanislav G Yanev","doi":"10.1016/s1099-4831(10)06805-7","DOIUrl":"https://doi.org/10.1016/s1099-4831(10)06805-7","url":null,"abstract":"The results described in these studies proved that the successful in vitro bioproduction of galanthamine from L. aestivum shoot-clumps required mainly the selection of in vitro clones with a genetically determined high ability to produce the desired alkaloids, although the expression of this ability could be additionally influenced by diverse exterior factors, such as some components of the nutrient medium, or the cultivation conditions of the ambience. Tissue differentiation was also of great importance for the biosynthetic capacity of the cultures. The most suitable inocula for in vitro biosynthesis of galanthamine in liquid medium were the directly regenerated shoot-clumps, ensuring high alkaloid concentrations between 1 and 2 mg/g DW for the selected clones. We observed astonishing clone-specific dynamics of the biosynthetic activity of all of the studied in vitro clones. The dynamics were obviously related to the strong biological clock of the species, persisting even in several-year old cultures. These dynamics did not coincide with those usual for the plants growing in situ and under controlled field conditions. In our opinion, the clone specificity of the biosynthetic dynamics could be due to the disturbance of the plant regulation mechanism under the equal conditions of the ambience in the culture room. The sharp decrease of the alkaloid concentrations were transient, followed by an increase, so that cultures were retaining their biosynthetic capacity. The biosynthesis of the main alkaloids, galanthamine and lycorine, was influenced by diverse stimulants such as substances causing stress (JA), feeding with alkaloid precursors (the amino acids phenylalanine and tyrosine, and CH), and physical treatment (acoustic waves). However, the course of the biosynthetic dynamics during the period of the treatments was always the most important factor for the success of secondary metabolism stimulation. As far as scaling-up of the in vitro biosynthesis of valuable compounds, a stable and predictable yield is required, and additional investigations aimed at the annulment of the effect plant biological clock on alkaloid biosynthesis are needed. The elucidation of the relative influences of the diverse factors modulating alkaloid biosynthesis was of great importance. The high galanthamine concentrations of the selected in vitro clones are a promising basis for future studies.","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"68 ","pages":"167-270"},"PeriodicalIF":0.0,"publicationDate":"2010-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(10)06805-7","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"28874373","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: 20

Chemistry and biology of Pancratium alkaloids. 水虎藤生物碱的化学和生物学。

Alkaloids: Chemistry and Biology Pub Date : 2010-01-01 DOI: 10.1016/s1099-4831(10)06801-x

Juan C Cedrón, M Del Arco-Aguilar, Ana Estévez-Braun, Angel G Ravelo

引用次数: 29