Christopher L Schardl, Daniel G Panaccione, Paul Tudzynski
{"title":"Ergot alkaloids--biology and molecular biology.","authors":"Christopher L Schardl, Daniel G Panaccione, Paul Tudzynski","doi":"10.1016/s1099-4831(06)63002-2","DOIUrl":"https://doi.org/10.1016/s1099-4831(06)63002-2","url":null,"abstract":"<p><p>EA have been a major benefit, and a major detriment, to humans since early in recorded history. Their medicinal properties have been used, and continue to be used, to aid in childbirth, with new uses being found in the treatment of neurological and cardiovascular disorders. The surprisingly broad range of pharmaceutical uses for EA stems from their affinities for multiple receptors for three distinct neurotransmitters (serotonin, dopamine, and adrenaline), from the great structural diversity of natural EA, and from the application of chemical techniques that further expand that structural diversity. The dangers posed by EA to humans and their livestock stem from the ubiquity of ergot fungi (Claviceps species) as parasites of cereals, and of related grass endophytes (Epichloë, Neotyphodium, and Balansia species) that may inhabit pasture grasses and produce toxic levels of EA. Further concerns stem from saprophytic EA producers in the genera Aspergillus and Penicillium, especially A. fumigatus, an opportunistic pathogen of humans. Numerous fungal species produce EA with a wide variety of structures and properties. These alkaloids are associated with plants in the families Poaceae, Cyperaceae, and Convolvulaceae, apparently because these plants can have symbiotic fungi that produce EA. Pharmacological activities of EA relate to their specific structures. Known as potent vasoconstrictors, the ergopeptines include a lysergic acid substituent with an amide linkage to a complex cyclol-lactam ring structure generated from three amino acids. Simpler lysergyl amides and clavines are more apt to have oxytonic or psychotropic activities. One of the lysergyl amides is LSD (5), the most potent hallucinogen known. The EA biosynthetic pathway in Claviceps species has been studied extensively for many decades, and recent studies have also employed epichloës and A. fumigatus. The early pathway, shared among these fungi, begins with the action of an aromatic prenyl transferase, DMATrp synthase, which links a dimethylallyl chain to L-tryptophan. When the dmaW gene encoding DMATrp synthase was cloned and sequenced, the predicted product bore no identifiable resemblance to other known prenyl transferases. The dma W genes of Claviceps species are present in clusters of genes, several of which also have demonstrated roles in EA biosynthesis. In many other fungi, dma W homologues are identifiable in otherwise very different gene clusters. The roles of DMA Trp synthase homologues in these other fungi are probably quite variable. One of them is thought to prenylate the phenolic oxygen of L-tyrosine, and another catalyzes the unusual reverse prenylation reaction in the biosynthesis of fumigaclavine C(10), an EA characteristic of A. fumigatus. The second step of the EA pathway is N-methylation of DMATrp (12) to form 13, which is then subjected to a series of oxidation/oxygenation and reduction reactions to generate, in order, chanoclavine-I (16), agroclavine (19), and ","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"63 ","pages":"45-86"},"PeriodicalIF":0.0,"publicationDate":"2006-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(06)63002-2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"26412666","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}
Lucia M Conserva, Cynara de Araújo B Pereira, José Maria Barbosa-Filho
{"title":"Alkaloids of the Hernandiaceae: occurrence and a compilation of their biological activities.","authors":"Lucia M Conserva, Cynara de Araújo B Pereira, José Maria Barbosa-Filho","doi":"10.1016/s1099-4831(05)62003-2","DOIUrl":"https://doi.org/10.1016/s1099-4831(05)62003-2","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"62 ","pages":"175-243"},"PeriodicalIF":0.0,"publicationDate":"2005-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(05)62003-2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25691322","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}
Ronaldo A Pilli, Giovanni B Rosso, Maria Da Conceição F De Oliveira
{"title":"The stemona alkaloids.","authors":"Ronaldo A Pilli, Giovanni B Rosso, Maria Da Conceição F De Oliveira","doi":"10.1016/s1099-4831(05)62002-0","DOIUrl":"https://doi.org/10.1016/s1099-4831(05)62002-0","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"62 ","pages":"77-173"},"PeriodicalIF":0.0,"publicationDate":"2005-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(05)62002-0","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25691321","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}
Emidio Vasconcelos Leitao Da-Cunha, Ivana Maria Fechinei, Diego Nunes Guedes, José Maria Barbosa-Filho, Marcelo Sobral Da Silva
{"title":"Protoberberine alkaloids.","authors":"Emidio Vasconcelos Leitao Da-Cunha, Ivana Maria Fechinei, Diego Nunes Guedes, José Maria Barbosa-Filho, Marcelo Sobral Da Silva","doi":"10.1016/s1099-4831(05)62001-9","DOIUrl":"https://doi.org/10.1016/s1099-4831(05)62001-9","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"62 ","pages":"1-75"},"PeriodicalIF":0.0,"publicationDate":"2005-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s1099-4831(05)62001-9","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25691320","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":"Clinical studies of camptothecin and derivatives.","authors":"Otto Soepenberg, Alex Sparreboom, Jaap Verweij","doi":"10.1016/s0099-9598(03)60001-5","DOIUrl":"https://doi.org/10.1016/s0099-9598(03)60001-5","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"60 ","pages":"1-50"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s0099-9598(03)60001-5","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"24055180","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":"Chemical and biological aspects of melanin.","authors":"D P Chakraborty, Shyamali Roy","doi":"10.1016/s0099-9598(03)60006-4","DOIUrl":"https://doi.org/10.1016/s0099-9598(03)60006-4","url":null,"abstract":"","PeriodicalId":35785,"journal":{"name":"Alkaloids: Chemistry and Biology","volume":"60 ","pages":"345-91"},"PeriodicalIF":0.0,"publicationDate":"2003-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1016/s0099-9598(03)60006-4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"24055184","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}