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Biosynthesis of fungal terpenoids† 真菌萜类化合物的生物合成。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-05-22 DOI: 10.1039/d3np00052d
Pan Luo , Jia-Hua Huang , Jian-Ming Lv , Gao-Qian Wang , Dan Hu , Hao Gao
{"title":"Biosynthesis of fungal terpenoids†","authors":"Pan Luo ,&nbsp;Jia-Hua Huang ,&nbsp;Jian-Ming Lv ,&nbsp;Gao-Qian Wang ,&nbsp;Dan Hu ,&nbsp;Hao Gao","doi":"10.1039/d3np00052d","DOIUrl":"10.1039/d3np00052d","url":null,"abstract":"<div><p>Covering: up to August 2023</p></div><div><p>Terpenoids, which are widely distributed in animals, plants, and microorganisms, are a large group of natural products with diverse structures and various biological activities. They have made great contributions to human health as therapeutic agents, such as the anti-cancer drug paclitaxel and anti-malarial agent artemisinin. Accordingly, the biosynthesis of this important class of natural products has been extensively studied, which generally involves two major steps: hydrocarbon skeleton construction by terpenoid cyclases and skeleton modification by tailoring enzymes. Additionally, fungi (Ascomycota and Basidiomycota) serve as an important source for the discovery of terpenoids. With the rapid development of sequencing technology and bioinformatics approaches, genome mining has emerged as one of the most effective strategies to discover novel terpenoids from fungi. To date, numerous terpenoid cyclases, including typical class I and class II terpenoid cyclases as well as emerging UbiA-type terpenoid cyclases, have been identified, together with a variety of tailoring enzymes, including cytochrome P450 enzymes, flavin-dependent monooxygenases, and acyltransferases. In this review, our aim is to comprehensively present all fungal terpenoid cyclases identified up to August 2023, with a focus on newly discovered terpenoid cyclases, especially the emerging UbiA-type terpenoid cyclases, and their related tailoring enzymes from 2015 to August 2023.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139544001","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
Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review 揭开金盏花科生物碱的神秘面纱：从生物合成到抗病毒潜力--综述。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-05-22 DOI: 10.1039/d3np00044c
Thilina U. Jayawardena , Natacha Merindol , Nuwan Sameera Liyanage , Isabel Desgagné-Penix
{"title":"Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review","authors":"Thilina U. Jayawardena ,&nbsp;Natacha Merindol ,&nbsp;Nuwan Sameera Liyanage ,&nbsp;Isabel Desgagné-Penix","doi":"10.1039/d3np00044c","DOIUrl":"10.1039/d3np00044c","url":null,"abstract":"<div><p>Covering: 2017 to 2023 (now)</p></div><div><p>Amaryllidaceae alkaloids (AAs) are a unique class of specialized metabolites containing heterocyclic nitrogen bridging that play a distinct role in higher plants. Irrespective of their diverse structures, most AAs are biosynthesized <em>via</em> intramolecular oxidative coupling. The complex organization of biosynthetic pathways is constantly enlightened by new insights owing to the advancement of natural product chemistry, synthetic organic chemistry, biochemistry, systems and synthetic biology tools and applications. These promote novel compound identification, trace-level metabolite quantification, synthesis, and characterization of enzymes engaged in AA catalysis, enabling the recognition of biosynthetic pathways. A complete understanding of the pathway benefits biotechnological applications in the long run. This review emphasizes the structural diversity of the AA specialized metabolites involved in biogenesis although the process is not entirely defined yet. Moreover, this work underscores the pivotal role of synthetic and enantioselective studies in justifying biosynthetic conclusions. Their prospective candidacy as lead constituents for antiviral drug discovery has also been established. However, a complete understanding of the pathway requires further interdisciplinary efforts in which antiviral studies address the structure–activity relationship. This review presents current knowledge on the topic.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138827259","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
Phytochemical and pharmacological properties of the genus Alpinia from 2016 to 2023 2016 年至 2023 年阿尔皮纳属的植物化学和药理特性。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2024-05-08 DOI: 10.1039/D4NP00004H
Isoo Youn, Ah-Reum Han, Donglan Piao, Hwaryeong Lee, Hyunkyung Kwak, Yeju Lee, Joo-Won Nam and Eun Kyoung Seo
{"title":"Phytochemical and pharmacological properties of the genus Alpinia from 2016 to 2023","authors":"Isoo Youn, Ah-Reum Han, Donglan Piao, Hwaryeong Lee, Hyunkyung Kwak, Yeju Lee, Joo-Won Nam and Eun Kyoung Seo","doi":"10.1039/D4NP00004H","DOIUrl":"10.1039/D4NP00004H","url":null,"abstract":"<p>Covering 2016 up to the end of 2023</p><p> <em>Alpinia</em> is the largest genus of flowering plants in the ginger family, Zingiberaceae, and comprises about 500 species. Many <em>Alpinia</em> are commonly cultivated ornamental plants, and some are used as spices or traditional medicine to treat inflammation, hyperlipidemia, and cancers. However, only a few comprehensive reviews have been published on the phytochemistry and pharmacology of this genus, and the latest review was published in 2017. In this review, we provide an extensive coverage of the studies on <em>Alpinia</em> species reported from 2016 through 2023, including newly isolated compounds and potential biological effects. The present review article shows that <em>Alpinia</em> species have a wide spectrum of pharmacological activities, most due to the activities of diarylheptanoids, terpenoids, flavonoids, and phenolics.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":10.2,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2024/np/d4np00004h?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140875260","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
Recent advances in total synthesis of protoberberine and chiral tetrahydroberberine alkaloids. 原小檗碱和手性四氢小檗碱全合成的最新进展。
IF 10.2 1区 化学
Natural Product Reports Pub Date : 2024-05-07 DOI: 10.1039/d4np00016a
Zhen-Xi Niu, Ya-Tao Wang, Jun-Feng Wang
{"title":"Recent advances in total synthesis of protoberberine and chiral tetrahydroberberine alkaloids.","authors":"Zhen-Xi Niu, Ya-Tao Wang, Jun-Feng Wang","doi":"10.1039/d4np00016a","DOIUrl":"10.1039/d4np00016a","url":null,"abstract":"<p><p>Covering: Up to 2024Due to the widespread distribution of protoberberine alkaloids (PBs) and tetrahydroberberine alkaloids (THPBs) in nature, coupled with their myriad unique physiological activities, they have garnered considerable attention from medical practitioners. Over the past few decades, synthetic chemists have devised various total synthesis methods to attain these structures, continually expanding reaction pathways to achieve more efficient synthetic strategies. Simultaneously, the chiral construction of THPBs has become a focal point. In this comprehensive review, we categorically summarized the developmental trajectory of the total synthesis of these alkaloids based on the core closure strategies of protoberberine and tetrahydroberberine.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":10.2,"publicationDate":"2024-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140848928","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 热销产品
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d4np90015d
Robert A. Hill , Andrew Sutherland
{"title":"Hot off the Press","authors":"Robert A. Hill ,&nbsp;Andrew Sutherland","doi":"10.1039/d4np90015d","DOIUrl":"10.1039/d4np90015d","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 eugeniinaline A from <em>Leuconotis eugeniifolia</em>.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140590976","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
Polyamine-containing natural products: structure, bioactivity, and biosynthesis† 含多胺的天然产物：结构、生物活性和生物合成。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d2np00087c
Qingshan Long , Wen Zhou , Haibo Zhou , Ying Tang , Wu Chen , Qingshu Liu , Xiaoying Bian
{"title":"Polyamine-containing natural products: structure, bioactivity, and biosynthesis†","authors":"Qingshan Long ,&nbsp;Wen Zhou ,&nbsp;Haibo Zhou ,&nbsp;Ying Tang ,&nbsp;Wu Chen ,&nbsp;Qingshu Liu ,&nbsp;Xiaoying Bian","doi":"10.1039/d2np00087c","DOIUrl":"10.1039/d2np00087c","url":null,"abstract":"<div><p>Covering: 2005 to August, 2023</p></div><div><p>Polyamine-containing natural products (NPs) have been isolated from a wide range of terrestrial and marine organisms and most of them exhibit remarkable and diverse activities, including antimicrobial, antiprotozoal, antiangiogenic, antitumor, antiviral, iron-chelating, anti-depressive, anti-inflammatory, insecticidal, antiobesity, and antioxidant properties. Their extraordinary activities and potential applications in human health and agriculture attract increasing numbers of studies on polyamine-containing NPs. In this review, we summarized the source, structure, classification, bioactivities and biosynthesis of polyamine-containing NPs, focusing on the biosynthetic mechanism of polyamine itself and representative polyamine alkaloids, polyamine-containing siderophores with catechol/hydroxamate/hydroxycarboxylate groups, nonribosomal peptide-(polyketide)-polyamine (NRP-(PK)-PA), and NRP-PK-long chain poly-fatty amine (lcPFAN) hybrid molecules.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49687742","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 biosynthetic logic and enzymatic machinery of approved fungi-derived pharmaceuticals and agricultural biopesticides 经批准的真菌衍生药物和农业生物农药的生物合成逻辑和酶机制。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d3np00040k
Moli Sang , Peiyuan Feng , Lu-Ping Chi , Wei Zhang
{"title":"The biosynthetic logic and enzymatic machinery of approved fungi-derived pharmaceuticals and agricultural biopesticides","authors":"Moli Sang ,&nbsp;Peiyuan Feng ,&nbsp;Lu-Ping Chi ,&nbsp;Wei Zhang","doi":"10.1039/d3np00040k","DOIUrl":"10.1039/d3np00040k","url":null,"abstract":"<div><p>Covering: 2000 to 2023</p></div><div><p>The kingdom Fungi has become a remarkably valuable source of structurally complex natural products (NPs) with diverse bioactivities. Since the revolutionary discovery and application of the antibiotic penicillin from <em>Penicillium</em>, a number of fungi-derived NPs have been developed and approved into pharmaceuticals and pesticide agents using traditional “activity-guided” approaches. Although emerging genome mining algorithms and surrogate expression hosts have brought revolutionary approaches to NP discovery, the time and costs involved in developing these into new drugs can still be prohibitively high. Therefore, it is essential to maximize the utility of existing drugs by rational design and systematic production of new chemical structures based on these drugs by synthetic biology. To this purpose, there have been great advances in characterizing the diversified biosynthetic gene clusters associated with the well-known drugs and in understanding the biosynthesis logic mechanisms and enzymatic transformation processes involved in their production. We describe advances made in the heterogeneous reconstruction of complex NP scaffolds using fungal polyketide synthases (PKSs), non-ribosomal peptide synthetases (NRPSs), PKS/NRPS hybrids, terpenoids, and indole alkaloids and also discuss mechanistic insights into metabolic engineering, pathway reprogramming, and cell factory development. Moreover, we suggest pathways for expanding access to the fungal chemical repertoire by biosynthesis of representative family members <em>via</em> common platform intermediates and through the rational manipulation of natural biosynthetic machineries for drug discovery.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"138289727","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
Nitrile biosynthesis in nature: how and why? 自然界中的腈生物合成：如何进行？
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d3np00028a
Mingyu Liu , Shengying Li
{"title":"Nitrile biosynthesis in nature: how and why?","authors":"Mingyu Liu ,&nbsp;Shengying Li","doi":"10.1039/d3np00028a","DOIUrl":"10.1039/d3np00028a","url":null,"abstract":"<div><p>Covering: up to the end of 2023</p></div><div><p>Natural nitriles comprise a small set of secondary metabolites which however show intriguing chemical and functional diversity. Various patterns of nitrile biosynthesis can be seen in animals, plants, and microorganisms with the characteristics of both evolutionary divergence and convergence. These specialized compounds play important roles in nitrogen metabolism, chemical defense against herbivores, predators and pathogens, and inter- and/or intraspecies communications. Here we review the naturally occurring nitrile-forming pathways from a biochemical perspective and discuss the biological and ecological functions conferred by diversified nitrile biosyntheses in different organisms. Elucidation of the mechanisms and evolutionary trajectories of nitrile biosynthesis underpins better understandings of nitrile-related biology, chemistry, and ecology and will ultimately benefit the development of desirable nitrile-forming biocatalysts for practical applications.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139400947","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 shikimate pathway: gateway to metabolic diversity 莽草酸途径：通向代谢多样性的大门
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d3np00037k
Vikram V. Shende , Katherine D. Bauman , Bradley S. Moore
{"title":"The shikimate pathway: gateway to metabolic diversity","authors":"Vikram V. Shende ,&nbsp;Katherine D. Bauman ,&nbsp;Bradley S. Moore","doi":"10.1039/d3np00037k","DOIUrl":"10.1039/d3np00037k","url":null,"abstract":"<div><p>Covering: 1997 to 2023</p></div><div><p>The shikimate pathway is the metabolic process responsible for the biosynthesis of the aromatic amino acids phenylalanine, tyrosine, and tryptophan. Seven metabolic steps convert phosphoenolpyruvate (PEP) and erythrose 4-phosphate (E4P) into shikimate and ultimately chorismate, which serves as the branch point for dedicated aromatic amino acid biosynthesis. Bacteria, fungi, algae, and plants (yet not animals) biosynthesize chorismate and exploit its intermediates in their specialized metabolism. This review highlights the metabolic diversity derived from intermediates of the shikimate pathway along the seven steps from PEP and E4P to chorismate, as well as additional sections on compounds derived from prephenate, anthranilate and the synonymous aminoshikimate pathway. We discuss the genomic basis and biochemical support leading to shikimate-derived antibiotics, lipids, pigments, cofactors, and other metabolites across the tree of life.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139083476","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
Promoter engineering of natural product biosynthetic gene clusters in actinomycetes: concepts and applications 放线菌天然产物生物合成基因簇的启动子工程：概念与应用。
IF 11.9 1区 化学
Natural Product Reports Pub Date : 2024-04-24 DOI: 10.1039/d3np00049d
Chang-Hun Ji , Hyun-Woo Je , Hiyoung Kim , Hahk-Soo Kang
{"title":"Promoter engineering of natural product biosynthetic gene clusters in actinomycetes: concepts and applications","authors":"Chang-Hun Ji ,&nbsp;Hyun-Woo Je ,&nbsp;Hiyoung Kim ,&nbsp;Hahk-Soo Kang","doi":"10.1039/d3np00049d","DOIUrl":"10.1039/d3np00049d","url":null,"abstract":"<div><p>Covering 2011 to 2022</p></div><div><p>Low titers of natural products in laboratory culture or fermentation conditions have been one of the challenging issues in natural products research. Many natural product biosynthetic gene clusters (BGCs) are also transcriptionally silent in laboratory culture conditions, making it challenging to characterize the structures and activities of their metabolites. Promoter engineering offers a potential solution to this problem by providing tools for transcriptional activation or optimization of biosynthetic genes. In this review, we summarize the 10 years of progress in promoter engineering approaches in natural products research focusing on the most metabolically talented group of bacteria actinomycetes.</p></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-04-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"139519213","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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