Yuyang Wang , Yan-Ni Shi , Hao Xiang , Yi-Ming Shi
{"title":"Exploring nature's battlefield: organismic interactions in the discovery of bioactive natural products","authors":"Yuyang Wang , Yan-Ni Shi , Hao Xiang , Yi-Ming Shi","doi":"10.1039/d4np00018h","DOIUrl":"10.1039/d4np00018h","url":null,"abstract":"<div><div>Covering: up to March 2024.</div></div><div><div>Microbial natural products have historically been a cornerstone for the discovery of therapeutic agents. Advanced (meta)genome sequencing technologies have revealed that microbes harbor far greater biosynthetic capabilities than previously anticipated. However, despite the application of CRISPR/Cas-based gene editing and high-throughput technologies to activate silent biosynthetic gene clusters, the rapid identification of new natural products has not led to a proportional increase in the discovery rate of lead compounds or drugs. A crucial issue in this gap may be insufficient knowledge about the inherent biological and physiological functions of microbial natural products. Addressing this gap necessitates recognizing that the generation of functional natural products is deeply rooted in the interactions between the producing microbes and other (micro)organisms within their ecological contexts, an understanding that is essential for harnessing their potential therapeutic benefits. In this review, we highlight the discovery of functional microbial natural products from diverse niches, including those associated with humans, nematodes, insects, fungi, protozoa, plants, and marine animals. Many of these findings result from an organismic-interaction-guided strategy using multi-omic approaches. The current importance of this topic lies in its potential to advance drug discovery in an era marked by increasing antimicrobial resistance.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 11","pages":"Pages 1630-1651"},"PeriodicalIF":10.2,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/np/d4np00018h?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142337502","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Chemical synthesis and functional evaluation of glycopeptides and glycoproteins containing rare glycosyl amino acid linkages","authors":"","doi":"10.1039/d4np00017j","DOIUrl":"10.1039/d4np00017j","url":null,"abstract":"<div><div>Covering: 1987 to 2023</div></div><div><div>Naturally existing glycoproteins through post-translational protein glycosylation are highly heterogeneous, which not only impedes the structure–function studies, but also hinders the development of their potential medical usage. Chemical synthesis represents one of the most powerful tools to provide the structurally well-defined glycoforms. Being the key step of glycoprotein synthesis, glycosylation usually takes place at serine, threonine, and asparagine residues, leading to the predominant formation of the <em>O</em>- and <em>N</em>-glycans, respectively. However, other amino acid residues containing oxygen, nitrogen, sulfur, and nucleophilic carbon atoms have also been found to be glycosylated. These diverse glycoprotein linkages, occurring from microorganisms to plants and animals, play also pivotal biological roles, such as in cell–cell recognition and communication. The availability of these homogenous rare glycopeptides and glycoproteins can help decipher the glyco-code for developing therapeutic agents. This review highlights the chemical approaches for assembly of the functional glycopeptides and glycoproteins bearing these “rare” carbohydrate–amino acid linkages between saccharide and canonical amino acid residues and their derivatives.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 9","pages":"Pages 1403-1440"},"PeriodicalIF":10.2,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141416725","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Xiaorong Yang , Xiaolou Miao , Lixia Dai , Xiao Guo , Janar Jenis , Jiyu Zhang , Xiaofei Shang
{"title":"Isolation, biological activity, and synthesis of isoquinoline alkaloids†","authors":"Xiaorong Yang , Xiaolou Miao , Lixia Dai , Xiao Guo , Janar Jenis , Jiyu Zhang , Xiaofei Shang","doi":"10.1039/d4np00023d","DOIUrl":"10.1039/d4np00023d","url":null,"abstract":"<div><div>Covering: 2019 to 2023</div></div><div><div>Isoquinoline alkaloids, an important class of <em>N</em>-based heterocyclic compounds, have attracted considerable attention from researchers worldwide. To follow up on our prior review (covering 2014–2018) and present the progress of this class of compounds, this review summarizes and provides updated literature on novel isoquinoline alkaloids isolated during the period of 2019–2023, together with their biological activity and underlying mechanisms of action. Moreover, with the rapid development of synthetic modification strategies, the synthesis strategies of isoquinoline alkaloids have been continuously optimized, and the total synthesis of these classes of natural products is reviewed critically herein. Over 250 molecules with a broad range of bioactivities, including antitumor, antibacterial, cardioprotective, anti-inflammatory, neuroprotective and other activities, are isolated and discussed. The total synthesis of more than nine classes of isoquinoline alkaloids is presented, and thirteen compounds constitute the first total synthesis. This survey provides new indications or possibilities for the discovery of new drugs from the original naturally occurring isoquinoline alkaloids.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 11","pages":"Pages 1652-1722"},"PeriodicalIF":10.2,"publicationDate":"2024-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/np/d4np00023d?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142360793","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Retraction: Recent advances in total synthesis of protoberberine and chiral tetrahydroberberine alkaloids","authors":"Zhen-Xi Niu, Ya-Tao Wang and Jun-Feng Wang","doi":"10.1039/D4NP90039A","DOIUrl":"10.1039/D4NP90039A","url":null,"abstract":"<p >Retraction of ‘Recent advances in total synthesis of protoberberine and chiral tetrahydroberberine alkaloids’ by Zhen-Xi Niu <em>et al.</em>, <em>Nat. Prod. Rep.</em>, 2024, https://doi.org/10.1039/d4np00016a.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 9","pages":" 1457-1457"},"PeriodicalIF":10.2,"publicationDate":"2024-08-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/np/d4np90039a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141986908","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Biosynthesis, biological activities, and structure–activity relationships of decalin-containing tetramic acid derivatives isolated from fungi","authors":"","doi":"10.1039/d4np00013g","DOIUrl":"10.1039/d4np00013g","url":null,"abstract":"<div><p>Covering: up to December 2023</p></div><div><p>Decalin-containing tetramic acid derivatives, especially 3-decalinoyltetramic acids (3-DTAs), are commonly found as fungal secondary metabolites. Numerous biological activities of this class of compounds, such as antibiotic, antiviral, antifungal, antiplasmodial, and antiprotozoal properties, have been the subject of ongoing research. For this reason, these molecules have attracted a lot of interest from the scientific community and various efforts including semi-synthesis, co-culturing with bacteria and biosynthetic gene sequencing have been made to obtain more derivatives. In this review, 3-DTAs are classified into four major groups based on the absolute configuration of the bicyclic decalin ring. Their biosynthetic pathways, various biological activities, and structure–activity relationship are then introduced.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Pages 1294-1317"},"PeriodicalIF":10.2,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141445623","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Hot off the press","authors":"Robert A. Hill , Andrew Sutherland","doi":"10.1039/d4np90034k","DOIUrl":"10.1039/d4np90034k","url":null,"abstract":"<div><p>A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products such as nitidane from <em>Heteromurus nitidus</em>.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Pages 1214-1218"},"PeriodicalIF":10.2,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141873647","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Architecture of full-length type I modular polyketide synthases revealed by X-ray crystallography, cryo-electron microscopy, and AlphaFold2","authors":"","doi":"10.1039/d3np00060e","DOIUrl":"10.1039/d3np00060e","url":null,"abstract":"<div><p>Covering: up to the end of 2023</p></div><div><p>Type I modular polyketide synthases construct polyketide natural products in an assembly line-like fashion, where the growing polyketide chain attached to an acyl carrier protein is passed from catalytic domain to catalytic domain. These enzymes have immense potential in drug development since they can be engineered to produce non-natural polyketides by strategically adding, exchanging, and deleting individual catalytic domains. In practice, however, this approach frequently results in complete failures or dramatically reduced product yields. A comprehensive understanding of modular polyketide synthase architecture is expected to resolve these issues. We summarize the three-dimensional structures and the proposed mechanisms of three full-length modular polyketide synthases, Lsd14, DEBS module 1, and PikAIII. We also describe the advantages and limitations of using X-ray crystallography, cryo-electron microscopy, and AlphaFold2 to study intact type I polyketide synthases.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Pages 1219-1234"},"PeriodicalIF":10.2,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140157126","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Medium-sized peptides from microbial sources with potential for antibacterial drug development†","authors":"","doi":"10.1039/d4np00002a","DOIUrl":"10.1039/d4np00002a","url":null,"abstract":"<div><p>Covering: 1993 to the end of 2022</p></div><div><p>As the rapid development of antibiotic resistance shrinks the number of clinically available antibiotics, there is an urgent need for novel options to fill the existing antibiotic pipeline. In recent years, antimicrobial peptides have attracted increased interest due to their impressive broad-spectrum antimicrobial activity and low probability of antibiotic resistance. However, macromolecular antimicrobial peptides of plant and animal origin face obstacles in antibiotic development because of their extremely short elimination half-life and poor chemical stability. Herein, we focus on medium-sized antibacterial peptides (MAPs) of microbial origin with molecular weights below 2000 Da. The low molecular weight is not sufficient to form complex protein conformations and is also associated to a better chemical stability and easier modifications. Microbially-produced peptides are often composed of a variety of non-protein amino acids and terminal modifications, which contribute to improving the elimination half-life of compounds. Therefore, MAPs have great potential for drug discovery and are likely to become key players in the development of next-generation antibiotics. In this review, we provide a detailed exploration of the modes of action demonstrated by 45 MAPs and offer a concise summary of the structure–activity relationships observed in these MAPs.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Pages 1235-1263"},"PeriodicalIF":10.2,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140670631","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Advances in the total synthesis of bis- and tris-indole alkaloids containing N-heterocyclic linker moieties","authors":"","doi":"10.1039/d4np00012a","DOIUrl":"10.1039/d4np00012a","url":null,"abstract":"<div><p>The past several years have seen an increase in the discovery and isolation of natural products of the indole alkaloid class. Bis- and tris-indole alkaloids are classes of natural products that have been shown to display diverse, potent biological activities. Of particular interest are bis- and tris-indole alkaloids containing N-heterocyclic linker moieties. It has been reported that more than 85% of biologically active compounds contain one or more heterocyclic moieties; of these, N-heterocycles have been identified as the most prevalent. The goal of this review is to provide a detailed overview of the recent advances in isolation and total synthesis of bis- and tris-indole alkaloids that contain N-heterocyclic linker moieties. The known biological activities of these natural products will also be discussed.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Pages 1264-1293"},"PeriodicalIF":10.2,"publicationDate":"2024-08-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/np/d4np00012a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140652380","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kate M. J. de Mattos-Shipley and Thomas J. Simpson
{"title":"Correction: The ‘emodin family’ of fungal natural products–amalgamating a century of research with recent genomics-based advances","authors":"Kate M. J. de Mattos-Shipley and Thomas J. Simpson","doi":"10.1039/D4NP90035A","DOIUrl":"10.1039/D4NP90035A","url":null,"abstract":"<p >Correction for ‘The ‘emodin family’ of fungal natural products–amalgamating a century of research with recent genomics-based advances’ by Kate M. J. de Mattos-Shipley <em>et al.</em>, <em>Nat. Prod. Rep.</em>, 2023, <strong>40</strong>, 174–201, https://doi.org/10.1039/D2NP00040G.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 9","pages":" 1456-1456"},"PeriodicalIF":10.2,"publicationDate":"2024-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11310742/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141905072","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}