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Total synthesis of isoflavonoids.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-02-11 DOI: 10.1039/d4np00060a
Mamoalosi A Selepe, Siyanda T Mthembu, Molahlehi S Sonopo
{"title":"Total synthesis of isoflavonoids.","authors":"Mamoalosi A Selepe, Siyanda T Mthembu, Molahlehi S Sonopo","doi":"10.1039/d4np00060a","DOIUrl":"https://doi.org/10.1039/d4np00060a","url":null,"abstract":"<p><p>Covering: 2012 to 2024Isoflavonoids are phenolic compounds with wide structural diversity and a plethora of biological activities. Owing to their structural variation and potential health-promoting and other benefits, they have been targeted for synthesis. Herein, we review the synthesis of natural isoflavonoids belonging to different classes that include isoflavones, isoflavanones, isoflavans, isoflavenes, pterocarpans, rotenoids, coumaronochromones, and coumestans. The synthetic methodologies employed and advancements in synthetic strategies are highlighted.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389554","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
Marine natural products.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-02-06 DOI: 10.1039/d4np00067f
Anthony R Carroll, Brent R Copp, Tanja Grkovic, Robert A Keyzers, Michèle R Prinsep
{"title":"Marine natural products.","authors":"Anthony R Carroll, Brent R Copp, Tanja Grkovic, Robert A Keyzers, Michèle R Prinsep","doi":"10.1039/d4np00067f","DOIUrl":"https://doi.org/10.1039/d4np00067f","url":null,"abstract":"<p><p>Covering: January to the end of December 2023This review covers the literature published in 2023 for marine natural products (MNPs), with 582 citations (541 for the period January to December 2023) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, the submerged parts of mangroves and other intertidal plants. The emphasis is on new compounds (1220 in 340 papers for 2023), together with the relevant biological activities, source organisms and country of origin. Pertinent reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included. An analysis of the progress in the study of prokaryote involvement in macro-invertebrate MNP production is discussed.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-02-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143254399","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.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-02-04 DOI: 10.1039/d5np90004b
Robert A Hill, Andrew Sutherland
{"title":"Hot off the press.","authors":"Robert A Hill, Andrew Sutherland","doi":"10.1039/d5np90004b","DOIUrl":"https://doi.org/10.1039/d5np90004b","url":null,"abstract":"<p><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 hyperzrone A from <i>Hypericum beanii</i>.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143187492","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
Advanced crystallography for structure determination of natural products.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-02-03 DOI: 10.1039/d4np00071d
Jian-Guo Song, Wen-Cai Ye, Ying Wang
{"title":"Advanced crystallography for structure determination of natural products.","authors":"Jian-Guo Song, Wen-Cai Ye, Ying Wang","doi":"10.1039/d4np00071d","DOIUrl":"https://doi.org/10.1039/d4np00071d","url":null,"abstract":"<p><p>Covering: up to 2025Crystallographic analysis has become the most reliable method for elucidating the structures of natural products, as it can provide absolute configurations with precise spatial arrangement information at the molecular level. However, obtaining high-quality and suitable-sized single crystals can be challenging for many natural products, making their structure determination difficult through traditional crystallography techniques. Recent advancements in this field have introduced innovative strategies to overcome the obstacle. These cutting-edge strategies include post-orientation of organic molecules within pre-prepared porous crystals (crystalline sponge method), co-crystallization of organic molecules with a crystalline mate through supramolecular interactions (crystalline mate method), encapsulation of organic molecules within inert oil nanodroplets (encapsulated nanodroplet crystallization method), and the use of electron diffraction and microscopy for nanocrystals (microcrystal electron diffraction method). This highlight delves into the fundamental principles, key characteristics, and representative applications of each strategy, as well as their respective advantages and limitations, aiming to guide researchers in choosing the most suitable crystallography approach for analyzing the structures of natural products.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143078060","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
The role and mechanisms of canonical and non-canonical tailoring enzymes in bacterial terpenoid biosynthesis.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-02-03 DOI: 10.1039/d4np00048j
Yuya Kakumu, Ayesha Ahmed Chaudhri, Eric J N Helfrich
{"title":"The role and mechanisms of canonical and non-canonical tailoring enzymes in bacterial terpenoid biosynthesis.","authors":"Yuya Kakumu, Ayesha Ahmed Chaudhri, Eric J N Helfrich","doi":"10.1039/d4np00048j","DOIUrl":"https://doi.org/10.1039/d4np00048j","url":null,"abstract":"<p><p>Covering: up to April 2024Terpenoids represent the largest and structurally most diverse class of natural products. According to textbook knowledge, this diversity arises from a two-step biosynthetic process: first, terpene cyclases generate a vast array of mono- and polycyclic hydrocarbon scaffolds with multiple stereocenters from a limited set of achiral precursors, a process extensively studied over the past two decades. Subsequently, tailoring enzymes further modify these complex scaffolds through regio- and stereocontrolled oxidation and other functionalization reactions, a topic of increasing interest in recent years. The resulting highly functionalized terpenoids exhibit a broad spectrum of unique biological activities, making them promising candidates for drug development. Recent advances in genome sequencing technologies along with the development and application of sophisticated genome mining tools have revealed bacteria as a largely untapped resource for the discovery of complex terpenoids. Functional characterization of a limited number of bacterial terpenoid biosynthetic pathways, combined with in-depth mechanistic studies of key enzymes, has begun to reveal the versatility of bacterial enzymatic processes involved in terpenoid modification. In this review, we examine the various tailoring reactions leading to complex bacterial terpenoids. We first discuss canonical terpene-modifying enzymes, that catalyze the functionalization of unactivated C-H bonds, incorporation of diverse functional groups, and oxidative and non-oxidative rearrangements. We then explore non-canonical terpene-modifying enzymes that facilitate oxidative rearrangement, cyclization, isomerization, and dimerization reactions. The increasing number of characterized tailoring enzymes that participate in terpene hydrocarbon scaffold fomation, rather than merely decorating pre-formed scaffolds suggests that a re-evaluation of the traditional two-phase model for terpenoid biosynthesis might be warranted. Finally, we address the potential and challenges of mining bacterial genomes to identify terpene biosynthetic gene clusters and expand the bacterial terpene biosynthetic and chemical space.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143078063","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
The fungal natural product class of the sorbicillinoids: structures, bioactivities, biosynthesis, and synthesis.
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-01-27 DOI: 10.1039/d4np00059e
Tobias M Milzarek, Tobias A M Gulder
{"title":"The fungal natural product class of the sorbicillinoids: structures, bioactivities, biosynthesis, and synthesis.","authors":"Tobias M Milzarek, Tobias A M Gulder","doi":"10.1039/d4np00059e","DOIUrl":"https://doi.org/10.1039/d4np00059e","url":null,"abstract":"<p><p>Covering 1948 up to October 2024Sorbicillinoids are a growing class of natural products (NPs) that stem from a variety of fungi including members of the orders <i>Hypocreales</i> and <i>Eurotiales</i>. This compound class is unique in its combination of structural complexity and pharmaceutically relevant biological activities. The majority of the sorbicillinoids, which are named after the common hexaketide precursor sorbicillin, exhibit anti-inflammatory, antimicrobial, cytotoxic, phytotoxic, and other selective enzyme inhibitory activities. Over the last eight decades, more than 170 sorbicillinoids, many with strong pharmaceutical potential, have been isolated and described in the literature. This review aims to provide an overview of the structural diversity, biosynthetic pathways, and synthetic studies of this exceptional NP class.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143045060","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
Sesterterpenoids: sources, structural diversity, biological activity, and data management. 酯萜类:来源、结构多样性、生物活性和数据管理。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-01-20 DOI: 10.1039/d4np00041b
Valeria Iobbi, Valentina Parisi, Mauro Giacomini, Francesco De Riccardis, Paola Brun, Laura Núñez-Pons, Giuliana Drava, Paolo Giordani, Maria Chiara Monti, Roberto Poggi, Ylenia Murgia, Nunziatina De Tommasi, Angela Bisio
{"title":"Sesterterpenoids: sources, structural diversity, biological activity, and data management.","authors":"Valeria Iobbi, Valentina Parisi, Mauro Giacomini, Francesco De Riccardis, Paola Brun, Laura Núñez-Pons, Giuliana Drava, Paolo Giordani, Maria Chiara Monti, Roberto Poggi, Ylenia Murgia, Nunziatina De Tommasi, Angela Bisio","doi":"10.1039/d4np00041b","DOIUrl":"https://doi.org/10.1039/d4np00041b","url":null,"abstract":"<p><p>Reviewing the literature published up to October 2024.Sesterterpenoids are one of the most chemically diverse and biologically promising subgroup of terpenoids, the largest family of secondary metabolites. The present review article summarizes more than seven decades of studies on isolation and characterization of more than 1600 structurally novel sesterterpenoids, supplemented by biological, pharmacological, ecological, and geographic distribution data. All the information have been implemented in eight tables available on the web and a relational database https://sesterterpenoids.unige.net/. The interface has two sections, one open to the public for reading only and the other, protected by an authentication mechanism, for timely updating of published results.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142996552","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
Unlocking hidden treasures: the evolution of high-throughput mass spectrometry in screening for cryptic natural products. 解锁隐藏的宝藏:高通量质谱法在筛选神秘天然产物中的演变。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-01-20 DOI: 10.1039/d4np00026a
Brett C Covington, Mohammad R Seyedsayamdost
{"title":"Unlocking hidden treasures: the evolution of high-throughput mass spectrometry in screening for cryptic natural products.","authors":"Brett C Covington, Mohammad R Seyedsayamdost","doi":"10.1039/d4np00026a","DOIUrl":"https://doi.org/10.1039/d4np00026a","url":null,"abstract":"<p><p>Covering: 1994 to 2024Historically, microbial natural product discovery has been predominantly guided by biological activity from crude microbial extracts with metabolite characterization proceeding one molecule at a time. Despite decades of bioactivity-guided isolations, genomic evidence now suggests that we have only accessed a small fraction of the total natural product potential from microorganisms and that the products of the vast majority of biosynthetic pathways remain to be identified. Here we describe recent advancements that have enabled high-throughput mass spectrometry and comparative metabolomics, which in turn facilitate high-throughput natural product discovery. These advancement promise to fully unlock the reservoir of microbial natural products.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142996553","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
Enzymatic ester bond formation strategies in fungal macrolide skeletons. 真菌大环内酯骨架的酶促酯键形成策略。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-01-20 DOI: 10.1039/d4np00050a
Jin-Mei Zhang, Guan-Yin Yuan, Yi Zou
{"title":"Enzymatic ester bond formation strategies in fungal macrolide skeletons.","authors":"Jin-Mei Zhang, Guan-Yin Yuan, Yi Zou","doi":"10.1039/d4np00050a","DOIUrl":"https://doi.org/10.1039/d4np00050a","url":null,"abstract":"<p><p>Covering: up to August 2024Macrolides, the core skeletons of numerous marketed drugs and bioactive natural products, have garnered considerable scientific interest owing to their structural diversity and broad spectrum of pharmaceutical activities. The formation of intramolecular ester bonds is a critical biocatalytic step in constructing macrolide skeletons. Here, we summarised enzymatic ester bond formation strategies in fungal polyketide (PK)-type, nonribosomal peptide (NRP)-type, and PK-NRP hybrid-type macrolides. In PK-type macrolides, ester bond formation is commonly catalysed by a <i>trans</i>-acting thioesterase (TE) or a <i>cis</i>-acting TE domain during the product release process. In NRP-type and PK-NRP hybrid-type macrolides, the ester bond is usually introduced through condensation (C) domain-catalysed esterification during the elongation or product release step. Although the TE and C domains share similarities in their catalytic mechanism, using hydroxyl groups as nucleophiles in an intramolecular nucleophilic attack, they differ in terms of the hydroxyl origin, the timing of ester bond formation, and domain location. Furthermore, some TE domains are utilized as chemoenzymatic catalysts to construct macrolides with different ring sizes. A comparison of ester bond formation between fungi and bacteria is also discussed. Exploring the biosynthetic pathways of fungal macrolides, elucidating the diverse strategies employed in the formation of ester bonds, and understanding the application of enzymes/domains in chemoenzymatic synthesis hold promise for the discovery of new bioactive macrolides in the future.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142996550","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
Human milk as a complex natural product. 母乳是一种复杂的天然产物。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2025-01-20 DOI: 10.1039/d4np00058g
Julie A Talbert, Steven D Townsend
{"title":"Human milk as a complex natural product.","authors":"Julie A Talbert, Steven D Townsend","doi":"10.1039/d4np00058g","DOIUrl":"https://doi.org/10.1039/d4np00058g","url":null,"abstract":"<p><p>Covering: up to the end of 2024Breastfeeding is one of the most effective ways to promote child health. However, characterizing the chemistry that fortifies the benefits of breastfeeding remains a grand challenge. Current efforts in the community are focused on characterizing the roles of the different carbohydrates, proteins, and fats in milk. The goal of this review is to highlight and describe current knowledge about the major classes of macromolecules in human milk and their potential role in infant health and wellness.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" ","pages":""},"PeriodicalIF":10.2,"publicationDate":"2025-01-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142996551","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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