{"title":"Progress in the Chemistry of Cytochalasans.","authors":"Hucheng Zhu, Chunmei Chen, Qingyi Tong, Yuan Zhou, Ying Ye, Lianghu Gu, Yonghui Zhang","doi":"10.1007/978-3-030-59444-2_1","DOIUrl":"https://doi.org/10.1007/978-3-030-59444-2_1","url":null,"abstract":"<p><p>Cytochalasans are a group of fungal-derived natural products characterized by a perhydro-isoindolone core fused with a macrocyclic ring, and they exhibit a high structural diversity and a broad spectrum of bioactivities. Cytochalasans have attracted significant attention from the chemical and pharmacological communities and have been reviewed previously from various perspectives in recent years. However, continued interest in the cytochalasans and the number of laboratory investigations on these compounds are both growing rapidly. This contribution provides a general overview of the isolation, structural determination, biological activities, biosynthesis, and total synthesis of cytochalasans. In total, 477 cytochalasans are covered, including \"merocytochalasans\" that arise by the dimerization or polymerization of one or more cytochalasan molecules with one or more other natural product units. This contribution provides a comprehensive treatment of the cytochalasans, and it is hoped that it may stimulate further work on these interesting natural products.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2021-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25540170","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":"Taccalonolide Microtubule Stabilizers.","authors":"Samantha S Yee, Lin Du, April L Risinger","doi":"10.1007/978-3-030-52966-6_3","DOIUrl":"https://doi.org/10.1007/978-3-030-52966-6_3","url":null,"abstract":"<p><p>Microtubule stabilizers are a mainstay in the treatment of many solid cancers and continue to find utility in combination therapy with molecularly targeted anticancer agents and immunotherapeutics. However, innate and acquired resistance to microtubule stabilizers can limit their clinical efficacy. The taccalonolides are a unique class of microtubule stabilizers isolated from plants of Tacca that circumvent clinically relevant mechanisms of drug resistance. Although initial reports suggested that the microtubule-stabilizing activity of the taccalonolides was independent of direct tubulin binding, additional studies have identified that potent C-22, C-23 epoxidized taccalonolides covalently bind the Aspartate 226 residue of β-tubulin and that this interaction is critical for their microtubule-stabilizing activity. The taccalonolides have distinct properties as compared to other microtubule stabilizers with regard to their biochemical effects on tubulin structure and dynamics that promote distinct cellular phenotypes. Some taccalonolides have demonstrated in vivo antitumor efficacy in drug-resistant tumor models with exquisite potency and long-lasting antitumor efficacy as a result of their irreversible target engagement. The recent identification of a site on the taccalonolide scaffold that is amenable to modification has provided evidence of the specificity of the taccalonolide-tubulin interaction. This also affords an opportunity to further optimize the targeted delivery of the taccalonolides to further improve their anticancer efficacy and potential for clinical development.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7800047/pdf/nihms-1657180.pdf","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"38700070","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Chemical Constituents of Ligularia Species (Asteraceae) and Their Diversity in East Asia.","authors":"Motoo Tori, Chiaki Kuroda","doi":"10.1007/978-3-030-53028-0_1","DOIUrl":"https://doi.org/10.1007/978-3-030-53028-0_1","url":null,"abstract":"<p><p>More than 100 Ligularia species and those of several related genera (Cremanthodium, Cacalia, Senecio, and others) in the plant family Senecioneae grow in East Asia. For many years, researchers have studied the chemical constituents of these plants, and terpenoids, flavonoids, sterols, alkaloids, and aromatic compounds have been isolated. Among these, in particular, numerous sesquiterpenoids were reported. In this contribution, relevant chemical studies are described mainly from literature reports appearing since 2000, inclusive of investigations performed by the present authors, on the diversity in secondary metabolites of Ligularia growing in the Hengduan Mountains area of China, focusing on eremophilane sesquiterpenoids and other metabolites. Terpenoids and aromatic compounds (totaling 1049), both new and known, are listed. Genetic studies and synthesis investigations are also reviewed briefly.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"25480115","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 Phytochemistry and Pharmacology of Hypericum.","authors":"Chuan-Yun Xiao, Qing Mu, Simon Gibbons","doi":"10.1007/978-3-030-52966-6_2","DOIUrl":"https://doi.org/10.1007/978-3-030-52966-6_2","url":null,"abstract":"<p><p>Hypericum L. is a genus of the family Hypericaceae within the dicotyledones. The constituents of Hypericum species are valued for their important biological properties. Their use is in the treatment of depression and as antibacterial agents has been well documented in the primary literature and in ethnobotanical reports. The present contribution gives a comprehensive summary of the chemical constituents of members of the genus Hypericum and their biological effects. A detailed account of the chemical constituents, including phloroglucinol derivatives, xanthones, dianthrones, and flavonoids, is included. These compounds show a diverse range of biological activities that include antimicrobial, cytotoxic, antidepressant-like, and antinociceptive effects.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"38701475","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}
Francisco A Macías, Alexandra G Durán, José M G Molinillo
{"title":"Allelopathy: The Chemical Language of Plants.","authors":"Francisco A Macías, Alexandra G Durán, José M G Molinillo","doi":"10.1007/978-3-030-52966-6_1","DOIUrl":"https://doi.org/10.1007/978-3-030-52966-6_1","url":null,"abstract":"<p><p>In Nature, the oldest method of communication between living systems is the chemical language. Plants, due to their lack of mobility, have developed the most sophisticated way of chemical communication. Despite that many examples involve this chemical communication process-allelopathy, there is still a lack of information about specific allelochemicals released into the environment, their purpose, as well as in-depth studies on the chemistry underground. These findings are critical to gain a better understanding of the role of these compounds and open up a wide range of possibilities and applications, especially in agriculture and phytomedicine. The most relevant aspects regarding the chemical language of plants, namely kind of allelochemicals, have been investigated, as well as their releasing mechanisms and their purpose will be described in this chapter.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"38701476","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":"Sesterterpenoids.","authors":"Takaaki Mitsuhashi, Ikuro Abe","doi":"10.1007/978-3-030-37865-3_1","DOIUrl":"https://doi.org/10.1007/978-3-030-37865-3_1","url":null,"abstract":"<p><p>Sesterterpenoids are known as a relatively small group of natural products. However, they represent a variety of simple to more complex structural types. This contribution focuses on the chemical structures of sesterterpenoids and how their structures are constructed in Nature.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37690826","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}
Zhen Liu, Marian Frank, Xiaoqin Yu, Haiqian Yu, Nam M Tran-Cong, Ying Gao, Peter Proksch
{"title":"Secondary Metabolites from Marine-Derived Fungi from China.","authors":"Zhen Liu, Marian Frank, Xiaoqin Yu, Haiqian Yu, Nam M Tran-Cong, Ying Gao, Peter Proksch","doi":"10.1007/978-3-030-37865-3_2","DOIUrl":"https://doi.org/10.1007/978-3-030-37865-3_2","url":null,"abstract":"<p><p>Marine-derived fungi play an important role in the search for structurally unique secondary metabolites, some of which show promising pharmacological activities that make them useful leads for drug discovery. Marine natural product research in China in general has made enormous progress in the last two decades as described in this chapter on fungal metabolites. This contribution covers 613 new natural products reported from 2001 to 2017 from marine-derived fungi obtained from algae, sponges, corals, and other marine organisms from Chinese waters. The genera Aspergillus (170 new natural products, 28%) and Penicillium (70 new natural products, 11%) were the main fungal producers of new natural products during the time period covered, whereas sponges (184 new natural products, 30%) were the most abundant source of new natural products, followed by corals (154 new natural products, 25%) and algae (130 new natural products, 21%). Close to 40% of all natural products covered in this contribution displayed various bioactivities. The major bioactivities reported were cytotoxicity against different cancer cell lines, antimicrobial (mainly antibacterial) activity, and antiviral activity, which accounted for 13%, 9%, and 3% of all natural products reported. In terms of structural classes, polyketides (188 new natural products, 31%) play a dominant role, and if prenylated polyketides and nitrogen-containing polyketides (included in meroterpenes and alkaloids in this contribution) are taken into account, their total number even exceeds 50%. Nitrogen-containing compounds including peptides (65 new natural products, 10%) and alkaloids (103 new natural products, 17%) are the second largest group.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2020-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37690827","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 Diversity and Biological Activity of African Propolis.","authors":"N. Blicharska, V. Seidel","doi":"10.1007/978-3-030-12858-6_3","DOIUrl":"https://doi.org/10.1007/978-3-030-12858-6_3","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85780048","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}
Darlon Irineu Bernardi, Fernanda Oliveira das Chagas, Afif Felix Monteiro, Gabriel Franco Dos Santos, Roberto Gomes de Souza Berlinck
{"title":"Secondary Metabolites of Endophytic Actinomycetes: Isolation, Synthesis, Biosynthesis, and Biological Activities.","authors":"Darlon Irineu Bernardi, Fernanda Oliveira das Chagas, Afif Felix Monteiro, Gabriel Franco Dos Santos, Roberto Gomes de Souza Berlinck","doi":"10.1007/978-3-030-01099-7_3","DOIUrl":"https://doi.org/10.1007/978-3-030-01099-7_3","url":null,"abstract":"<p><p>Endophytic Actinobacteria are a microbial group that is still poorly investigated. Their association with plants constitutes a unique trait conferring specific biological and chemical features to endophytic Actinobacteria. This contribution discusses aspects of endophytic actinobacterial biology and chemistry comprehensively, including the biosynthesis and total synthesis of secondary metabolites produced in culture. It also presents perspectives for the future of microbial bioactive natural products discovery, with emphasis on the secondary metabolism of endophytic Actinobacteria.</p>","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1007/978-3-030-01099-7_3","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37101992","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":"Bioactive Compounds Involved in the Life Cycle of Higher Plants.","authors":"H. Shigemori","doi":"10.1007/978-3-030-12858-6_2","DOIUrl":"https://doi.org/10.1007/978-3-030-12858-6_2","url":null,"abstract":"","PeriodicalId":20703,"journal":{"name":"Progress in the chemistry of organic natural products","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74401281","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}