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Natural ten-membered lactones: sources, structural diversity, biological activity, and intriguing future† 天然十元内酯：来源、结构多样性、生物活性和有趣的未来。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-24 DOI: 10.1039/d3np00013c
Vsevolod Dubovik , Anna Dalinova , Alexander Berestetskiy
{"title":"Natural ten-membered lactones: sources, structural diversity, biological activity, and intriguing future†","authors":"Vsevolod Dubovik ,&nbsp;Anna Dalinova ,&nbsp;Alexander Berestetskiy","doi":"10.1039/d3np00013c","DOIUrl":"10.1039/d3np00013c","url":null,"abstract":"<div><p>Covering: 2012 to 2022</p></div><div><p>Ten-membered lactones (TMLs) are an interesting and diverse group of natural polyketides that are abundant in fungi and, to a lesser extent, in bacteria, marine organisms, and insects. TMLs are known for their ability to exhibit a wide spectrum of biological activity, including phytotoxic, cytotoxic, antifungal, antibacterial, and others. However, the random discovery of these compounds by scientific groups with various interests worldwide has resulted in patchy information about their distribution among different organisms and their biological activity. Therefore, despite more than 60 years of research history, there is still no common understanding of the natural sources of TMLs, their structural type classification, and most characteristic biological activities. The controversial nomenclature, incorrect or erroneous structure elucidation, poor identification of producing organisms, and scattered information on the biological activity of compounds – all these factors have led to the problems with dereplication and the directed search for TMLs. This review consists of two parts: the first part (Section 2) covers 104 natural TMLs, published between 2012 and 2022 (after the publishing of the previous review), and the second part (Section 3) summarizes information about 214 TMLs described during 1964–2022 and as a result highlights the main problems and trends in the study of these intriguing natural products.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Pages 85-112"},"PeriodicalIF":11.9,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"54227030","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}
引用次数: 0
Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers† 茚酮倍半萜及其低聚物的化学和生物活性。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-24 DOI: 10.1039/d3np00022b
Jun Luo , Danyang Zhang , Pengfei Tang , Nan Wang , Shuai Zhao , Lingyi Kong
{"title":"Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers†","authors":"Jun Luo ,&nbsp;Danyang Zhang ,&nbsp;Pengfei Tang ,&nbsp;Nan Wang ,&nbsp;Shuai Zhao ,&nbsp;Lingyi Kong","doi":"10.1039/d3np00022b","DOIUrl":"10.1039/d3np00022b","url":null,"abstract":"<div><p>Covering: 1925 to July 2023</p></div><div><p>Among the sesquiterpenoids with rich structural diversity and potential bioactivities, lindenane sesquiterpenoids (LSs) possess a characteristic <em>cis</em>, <em>trans</em>-3,5,6-carbocyclic skeleton and mainly exist as monomers and diverse oligomers in plants from the <em>Lindera</em> genus and Chloranthaceae family. Since the first identification of lindeneol from <em>Lindera strychnifolia</em> in 1925, 354 natural LSs and their oligomers with anti-inflammatory, antitumor, and anti-infective activities have been discovered. Structurally, two-thirds of LSs exist as oligomers with interesting skeletons through diverse polymeric patterns, especially Diels–Alder [4 + 2] cycloaddition. Fascinated by their diverse bioactivities and intriguing polycyclic architectures, synthetic chemists have engaged in the total synthesis of natural LSs in recent decades. In this review, the research achievements related to LSs from 1925 to July of 2023 are systematically and comprehensively summarized, focusing on the classification of their structures, chemical synthesis, and bioactivities, which will be helpful for further research on LSs and their oligomers.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Pages 25-58"},"PeriodicalIF":11.9,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41092304","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}
引用次数: 0
Structural insights into the diverse prenylating capabilities of DMATS prenyltransferases DMATS异丙基转移酶不同异丙基化能力的结构见解。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-24 DOI: 10.1039/d3np00036b
Evan T. Miller , Oleg V. Tsodikov , Sylvie Garneau-Tsodikova
{"title":"Structural insights into the diverse prenylating capabilities of DMATS prenyltransferases","authors":"Evan T. Miller ,&nbsp;Oleg V. Tsodikov ,&nbsp;Sylvie Garneau-Tsodikova","doi":"10.1039/d3np00036b","DOIUrl":"10.1039/d3np00036b","url":null,"abstract":"<div><p>Covering: 2009 up to August 2023</p></div><div><p>Prenyltransferases (PTs) are involved in the primary and the secondary metabolism of plants, bacteria, and fungi, and they are key enzymes in the biosynthesis of many clinically relevant natural products (NPs). The continued biochemical and structural characterization of the soluble dimethylallyl tryptophan synthase (DMATS) PTs over the past two decades have revealed the significant promise that these enzymes hold as biocatalysts for the chemoenzymatic synthesis of novel drug leads. This is a comprehensive review of DMATSs describing the structure–function relationships that have shaped the mechanistic underpinnings of these enzymes, as well as the application of this knowledge to the engineering of DMATSs. We summarize the key findings and lessons learned from these studies over the past 14 years (2009–2023). In addition, we identify current gaps in our understanding of these fascinating enzymes.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Pages 113-147"},"PeriodicalIF":11.9,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"71475658","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}
引用次数: 0
Huperzine alkaloids: forty years of total syntheses 石杉碱生物碱：四十年的全合成。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-24 DOI: 10.1039/d3np00029j
Bichu Cheng , Lili Song , Fener Chen
{"title":"Huperzine alkaloids: forty years of total syntheses","authors":"Bichu Cheng ,&nbsp;Lili Song ,&nbsp;Fener Chen","doi":"10.1039/d3np00029j","DOIUrl":"10.1039/d3np00029j","url":null,"abstract":"<div><p>Covering: up to 2023</p></div><div><p>Huperzine alkaloids are a group of natural products belonging to the <em>Lycopodium</em> alkaloids family. The representative member huperzine A has a unique structure and exhibits potent inhibitory activity against acetylcholine esterase (AChE). This subfamily of alkaloids provides a great opportunity for developing synthetic methodologies and asymmetric synthesis. The efforts towards the synthesis of huperzine A have cultivated dozens of total syntheses and a rich body of new chemistry. Impressive progress has also been made in the synthesis of other huperzine alkaloids. The total syntheses of huperzines B, U, O, Q and R, structure reassignment and total syntheses of huperzines K, M and N have been reported in the past decade. This review focuses on the synthetic organic chemistry and the biosynthesis and medicinal chemistry of huperzines are also covered briefly.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Pages 59-84"},"PeriodicalIF":11.9,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41186139","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}
引用次数: 0
Simple phenylpropanoids: recent advances in biological activities, biosynthetic pathways, and microbial production† 简单苯丙烷类化合物：生物活性、生物合成途径和微生物生产的最新进展。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-24 DOI: 10.1039/d3np00012e
Zhanpin Zhu , Ruibing Chen , Lei Zhang
{"title":"Simple phenylpropanoids: recent advances in biological activities, biosynthetic pathways, and microbial production†","authors":"Zhanpin Zhu ,&nbsp;Ruibing Chen ,&nbsp;Lei Zhang","doi":"10.1039/d3np00012e","DOIUrl":"10.1039/d3np00012e","url":null,"abstract":"<div><p>Covering: 2000 to 2023</p></div><div><p>Simple phenylpropanoids are a large group of natural products with primary C6–C3 skeletons. They are not only important biomolecules for plant growth but also crucial chemicals for high-value industries, including fragrances, nutraceuticals, biomaterials, and pharmaceuticals. However, with the growing global demand for simple phenylpropanoids, direct plant extraction or chemical synthesis often struggles to meet current needs in terms of yield, titre, cost, and environmental impact. Benefiting from the rapid development of metabolic engineering and synthetic biology, microbial production of natural products from inexpensive and renewable sources provides a feasible solution for sustainable supply. This review outlines the biological activities of simple phenylpropanoids, compares their biosynthetic pathways in different species (plants, bacteria, and fungi), and summarises key research on the microbial production of simple phenylpropanoids over the last decade, with a focus on engineering strategies that seem to hold most potential for further development. Moreover, constructive solutions to the current challenges and future perspectives for industrial production of phenylpropanoids are presented.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Pages 6-24"},"PeriodicalIF":11.9,"publicationDate":"2024-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41091109","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}
引用次数: 0
Correction: Biosynthesis, biological activities, and structure–activity relationships of decalin-containing tetramic acid derivatives isolated from fungi 更正：从真菌中分离出的含蜕皮激素的四元酸衍生物的生物合成、生物活性和结构-活性关系
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2024-01-01
Hyun Woo Kim , Jin Woo Lee , Sang Hee Shim
{"title":"Correction: Biosynthesis, biological activities, and structure–activity relationships of decalin-containing tetramic acid derivatives isolated from fungi","authors":"Hyun Woo Kim ,&nbsp;Jin Woo Lee ,&nbsp;Sang Hee Shim","doi":"","DOIUrl":"","url":null,"abstract":"<div><p>Correction for ‘Biosynthesis, biological activities, and structure–activity relationships of decalin-containing tetramic acid derivatives isolated from fungi’ by Hyun Woo Kim <em>et al.</em>, <em>Nat. Prod. Rep.</em>, 2024, <span>https://doi.org/10.1039/d4np00013g</span>.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 8","pages":"Page 1318"},"PeriodicalIF":10.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142040262","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}
引用次数: 0
Correction: Hot off the Press 更正：热销
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-01 DOI: 10.1039/d3np90056h
Robert A. Hill , Andrew Sutherland
{"title":"Correction: Hot off the Press","authors":"Robert A. Hill ,&nbsp;Andrew Sutherland","doi":"10.1039/d3np90056h","DOIUrl":"10.1039/d3np90056h","url":null,"abstract":"<div><p>Correction for ‘Hot off the Press’ by Robert A. Hill <em>et al.</em>, <em>Nat. Prod. Rep.</em>, 2023, <strong>40</strong>, 1816–1821, <span>https://doi.org/10.1039/d3np90052e</span>.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 1","pages":"Page 148"},"PeriodicalIF":11.9,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139083531","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}
引用次数: 0
Correction: The ‘emodin family’ of fungal natural products–amalgamating a century of research with recent genomics-based advances 更正：真菌天然产物 "大黄素家族"--一个世纪的研究与基于基因组学的最新进展相结合
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2024-01-01
Kate M. J. de Mattos-Shipley , 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 ,&nbsp;Thomas J. Simpson","doi":"","DOIUrl":"","url":null,"abstract":"<div><div>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, <span>https://doi.org/10.1039/D2NP00040G</span>.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 9","pages":"Page 1456"},"PeriodicalIF":10.2,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142356923","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}
引用次数: 0
Correction: Future antimalarials from Artemisia? A rationale for natural product mining against drug-refractory Plasmodium stages 更正：未来的青蒿抗疟药？针对难治性疟原虫阶段挖掘天然产品的理由。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-01-01 DOI: 10.1039/d4np90001d
Alexandre Maciuk , Dominique Mazier , Romain Duval
{"title":"Correction: Future antimalarials from Artemisia? A rationale for natural product mining against drug-refractory Plasmodium stages","authors":"Alexandre Maciuk ,&nbsp;Dominique Mazier ,&nbsp;Romain Duval","doi":"10.1039/d4np90001d","DOIUrl":"10.1039/d4np90001d","url":null,"abstract":"<div><p>Correction for ‘Future antimalarials from <em>Artemisia</em>? A rationale for natural product mining against drug-refractory <em>Plasmodium</em> stages’ by Alexandre Maciuk <em>et al.</em>, <em>Nat. Prod. Rep.</em>, 2023, <strong>40</strong>, 1130–1144, <span>https://doi.org/10.1039/D3NP00001J</span>.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"41 3","pages":"Page 512"},"PeriodicalIF":11.9,"publicationDate":"2024-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139477800","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}
引用次数: 0
Hot off the Press 刚出版的。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2023-12-04 DOI: 10.1039/D3NP90052E
Robert A. Hill and Andrew Sutherland
{"title":"Hot off the Press","authors":"Robert A. Hill and Andrew Sutherland","doi":"10.1039/D3NP90052E","DOIUrl":"10.1039/D3NP90052E","url":null,"abstract":"<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 alscholarine A from <em>Alstonia scholaris</em>.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 12","pages":" 1816-1821"},"PeriodicalIF":11.9,"publicationDate":"2023-12-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138476272","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}
引用次数: 0
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