Progress in the chemistry of organic natural products最新文献

{"title":"The Laurencia Paradox: An Endless Source of Chemodiversity.","authors":"Maria Harizani,&nbsp;Efstathia Ioannou,&nbsp;Vassilios Roussis","doi":"10.1007/978-3-319-33172-0_2","DOIUrl":"https://doi.org/10.1007/978-3-319-33172-0_2","url":null,"abstract":"<p><p>Nature, the most prolific source of biological and chemical diversity, has provided mankind with treatments for health problems since ancient times and continues to be the most promising reservoir of bioactive chemicals for the development of modern drugs. In addition to the terrestrial organisms that still remain a promising source of new bioactive metabolites, the marine environment, covering approximately 70% of the Earth's surface and containing a largely unexplored biodiversity, offers an enormous resource for the discovery of novel compounds. According to the MarinLit database, more than 27,000 metabolites from marine macro- and microorganisms have been isolated to date providing material and key structures for the development of new products in the pharmaceutical, food, cosmeceutical, chemical, and agrochemical sectors. Algae, which thrive in the euphotic zone, were among the first marine organisms that were investigated as sources of food, nutritional supplements, soil fertilizers, and bioactive metabolites.Red algae of the genus Laurencia are accepted unanimously as one of the richest sources of new secondary metabolites. Their cosmopolitan distribution, along with the chemical variation influenced to a significant degree by environmental and genetic factors, have resulted in an endless parade of metabolites, often featuring multiple halogenation sites.The present contribution, covering the literature until August 2015, offers a comprehensive view of the chemical wealth and the taxonomic problems currently impeding chemical and biological investigations of the genus Laurencia. Since mollusks feeding on Laurencia are, in many cases, bioaccumulating, and utilize algal metabolites as chemical weaponry against natural enemies, metabolites of postulated dietary origin of sea hares that feed on Laurencia species are also included in the present review. Altogether, 1047 secondary metabolites, often featuring new carbocyclic skeletons, have been included.The chapter addresses: (1) the \"Laurencia complex\", the botanical description and the growth and population dynamics of the genus, as well as its chemical diversity and ecological relations; (2) the secondary metabolites, which are organized according to their chemical structures and are classified into sesquiterpenes, diterpenes, triterpenes, acetogenins, indoles, aromatic compounds, steroids, and miscellaneous compounds, as well as their sources of isolation which are depicted in tabulated form, and (3) the biological activity organized according to the biological target and the ecological functions of Laurencia metabolites. </p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"102 ","pages":"91-252"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-33172-0_2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34703231","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":"Ingenane Diterpenoids.","authors":"Giovanni Appendino","doi":"10.1007/978-3-319-33172-0_1","DOIUrl":"https://doi.org/10.1007/978-3-319-33172-0_1","url":null,"abstract":"<p><p>Despite a more recent isolation and chemical characterization when compared to phorbol, along with its chemical instability, limited distribution in Nature, and scarce availability, ingenol is the only Euphorbia diterpenoid that has undergone successful pharmaceutical development, with ingenol 3-angelate (ingenol mebutate, Picato(®)) entering the pharmaceutical market in 2012 for the treatment of actinic keratosis. The phytochemical, chemical, and biological literature on members of the ingenane class of diterpenoids is reviewed from their first isolation in 1968 through 2015, highlighting unresolved issues both common to phorboids (biogenesis, relationship between molecular targets, and in vivo activity) and specific to ingenol derivatives (two-dimensional representation, in-out stereoisomerism, versatility of binding mode to PKC, and inconsistencies in the structural elucidation of some classes of derivatives). The biogenesis of ingenol is discussed in the light of the Jakupovic proposal of a dissection between the formation of the macrocyclic Euphorbia diterpenoids and the phorboids, and the clinical development of ingenol mebutate is chronicled in the light of its \"reverse-pharmacology\" focus. </p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"102 ","pages":"1-90"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-33172-0_1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34703229","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":"Acetogenins from Annonaceae.","authors":"C. Liaw, Jing-Ru Liou, Tung‐Ying Wu, F. Chang, Y. Wu","doi":"10.1007/978-3-319-22692-7_2","DOIUrl":"https://doi.org/10.1007/978-3-319-22692-7_2","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"11 1","pages":"113-230"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88695629","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":"Erratum to: Dimeric Sesquiterpenoids.","authors":"Shang-Gao Liao,&nbsp;Jian-Min Yue","doi":"10.1007/978-3-319-22692-7_3","DOIUrl":"https://doi.org/10.1007/978-3-319-22692-7_3","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"101 ","pages":"E1"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-22692-7_3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"34318231","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":"Foreword. Methodology.","authors":"Kinghorn A D,&nbsp;Falk H,&nbsp;Kobayashi J","doi":"","DOIUrl":"","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"v-vi"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012985","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":"Structure elucidation of natural compounds by X-ray crystallography.","authors":"Ulrike Wagner,&nbsp;Christoph Kratky","doi":"10.1007/978-3-319-05275-5_1","DOIUrl":"https://doi.org/10.1007/978-3-319-05275-5_1","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"1-75"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-05275-5_1","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012986","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":"Mass spectrometry in natural product structure elucidation.","authors":"Herbert Budzikiewicz","doi":"10.1007/978-3-319-05275-5_2","DOIUrl":"https://doi.org/10.1007/978-3-319-05275-5_2","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"77-221"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-05275-5_2","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012987","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":"Nuclear magnetic resonance in the structural elucidation of natural products.","authors":"William F Reynolds,&nbsp;Eugene P Mazzola","doi":"10.1007/978-3-319-05275-5_3","DOIUrl":"https://doi.org/10.1007/978-3-319-05275-5_3","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"223-309"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-05275-5_3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012988","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":"Vibrational circular dichroism absolute configuration determination of natural products.","authors":"Pedro Joseph-Nathan,&nbsp;Bárbara Gordillo-Román","doi":"10.1007/978-3-319-05275-5_4","DOIUrl":"https://doi.org/10.1007/978-3-319-05275-5_4","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"311-452"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-05275-5_4","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012989","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 Series \"Progress in the Chemistry of Organic Natural Products\": 75 years of service in the development of natural product chemistry.","authors":"Rudolf Werner Soukup,&nbsp;Klara Soukup","doi":"10.1007/978-3-319-05275-5_5","DOIUrl":"https://doi.org/10.1007/978-3-319-05275-5_5","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":"100 ","pages":"453-588"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-319-05275-5_5","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"33012990","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}