Covering: 1976 to December 2023Chloranthaceae is comprised of four extant genera (Chloranthus, Sarcandra, Hedyosmum, and Ascarina), totaling about 80 species, many of which have been widely used as herbal medicines for diverse medical purposes. Chloranthaceae plants represent a rich source of structurally interesting and diverse secondary metabolites, with sesquiterpenoids and diterpenoids being the predominant structural types. Lindenane sesquiterpenoids and their oligomers, chemotaxonomical markers of the family Chloranthaceae, have shown a wide spectrum of bioactivities, attracting significant attention from organic chemists and pharmacologists. Recent achievements also demonstrated the research value of two unique structural types in this plant family, sesquiterpenoid-monoterpenoid heterodimers and meroterpenoids. This review systematically summarizes 682 structurally characterized terpenoids from 22 Chloranthaceae plants and their key biological activities as well as the chemical synthesis of selected terpenoids.
{"title":"Terpenoids of plants from Chloranthaceae family: chemistry, bioactivity, and synthesis.","authors":"Bin Zhou, Jian-Min Yue","doi":"10.1039/d4np00005f","DOIUrl":"https://doi.org/10.1039/d4np00005f","url":null,"abstract":"<p><p>Covering: 1976 to December 2023Chloranthaceae is comprised of four extant genera (<i>Chloranthus</i>, <i>Sarcandra</i>, <i>Hedyosmum</i>, and <i>Ascarina</i>), totaling about 80 species, many of which have been widely used as herbal medicines for diverse medical purposes. Chloranthaceae plants represent a rich source of structurally interesting and diverse secondary metabolites, with sesquiterpenoids and diterpenoids being the predominant structural types. Lindenane sesquiterpenoids and their oligomers, chemotaxonomical markers of the family Chloranthaceae, have shown a wide spectrum of bioactivities, attracting significant attention from organic chemists and pharmacologists. Recent achievements also demonstrated the research value of two unique structural types in this plant family, sesquiterpenoid-monoterpenoid heterodimers and meroterpenoids. This review systematically summarizes 682 structurally characterized terpenoids from 22 Chloranthaceae plants and their key biological activities as well as the chemical synthesis of selected terpenoids.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141160430","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}
Covering: up to the mid of 2023Plants secrete defense resins rich in small-molecule natural products under abiotic and biotic stresses. This comprehensive review encompasses the literature published up to mid-2023 on medicinal plant resin natural products from six main contributor genera, featuring 275 citations that refer to 1115 structurally diverse compounds. The scope of this review extends to include essential information such as the racemic nature of metabolites found in different species of plant resins, source of resins, and revised structures. Additionally, we carefully analyze the reported biological activities of resins, organizing them based on the their structures. The findings offer important insights into the relationship between their structure and activity. Furthermore, this detailed examination can be valuable for researchers and scientists in the field of medicinal plant resin natural products and will promote continued exploration and progress in this area.
{"title":"Medicinal plant resin natural products: structural diversity and biological activities.","authors":"Madhu Babu Sura, Yong-Xian Cheng","doi":"10.1039/d4np00007b","DOIUrl":"https://doi.org/10.1039/d4np00007b","url":null,"abstract":"<p><p>Covering: up to the mid of 2023Plants secrete defense resins rich in small-molecule natural products under abiotic and biotic stresses. This comprehensive review encompasses the literature published up to mid-2023 on medicinal plant resin natural products from six main contributor genera, featuring 275 citations that refer to 1115 structurally diverse compounds. The scope of this review extends to include essential information such as the racemic nature of metabolites found in different species of plant resins, source of resins, and revised structures. Additionally, we carefully analyze the reported biological activities of resins, organizing them based on the their structures. The findings offer important insights into the relationship between their structure and activity. Furthermore, this detailed examination can be valuable for researchers and scientists in the field of medicinal plant resin natural products and will promote continued exploration and progress in this area.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":null,"pages":null},"PeriodicalIF":11.9,"publicationDate":"2024-05-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141092398","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}
Ribosomally synthesized and posttranslationally modified peptides (RiPPs) continue to be a rich source of chemically diverse and bioactive peptide natural products. In recent years, cyclophane-containing RiPP natural products and their biosynthetic pathways have been more frequently encountered. This highlight will focus on bacterial monoaryl cyclophane-containing RiPPs. This class of RiPPs is produced by radical SAM/SPASM enzymes that form a crosslink between the aromatic ring and sidechain of two amino acid residues of the precursor peptide. Selected natural products from these pathways exhibit specific antibacterial activity against gram-negative pathogens. The approaches used to discover these pathways and products will be described and categorized as natural product-first or enzyme-first. The breadth of ring systems formed by the enzymes, enzyme mechanism, and recent reports of synthetic methods for constructing these ring systems will also be presented. Bacterial cyclophane-containing RiPPs and their biosynthetic enzymes represent an untapped source of scaffolds for drug discovery and tools for synthetic biology.
{"title":"Bacterial cyclophane-containing RiPPs from radical SAM enzymes","authors":"Chin-Soon Phan , Brandon I. Morinaka","doi":"10.1039/d3np00030c","DOIUrl":"10.1039/d3np00030c","url":null,"abstract":"<div><p>Covering: 2016 to 2023</p></div><div><p>Ribosomally synthesized and posttranslationally modified peptides (RiPPs) continue to be a rich source of chemically diverse and bioactive peptide natural products. In recent years, cyclophane-containing RiPP natural products and their biosynthetic pathways have been more frequently encountered. This highlight will focus on bacterial monoaryl cyclophane-containing RiPPs. This class of RiPPs is produced by radical SAM/SPASM enzymes that form a crosslink between the aromatic ring and sidechain of two amino acid residues of the precursor peptide. Selected natural products from these pathways exhibit specific antibacterial activity against gram-negative pathogens. The approaches used to discover these pathways and products will be described and categorized as natural product-first or enzyme-first. The breadth of ring systems formed by the enzymes, enzyme mechanism, and recent reports of synthetic methods for constructing these ring systems will also be presented. Bacterial cyclophane-containing RiPPs and their biosynthetic enzymes represent an untapped source of scaffolds for drug discovery and tools for synthetic biology.</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":"138476271","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}
Léa Barreda , Céline Brosse , Stéphanie Boutet , François Perreau , Loïc Rajjou , Loïc Lepiniec , Massimiliano Corso
Covering: up to 2023
Specialized metabolite (SM) modifications and/or decorations, corresponding to the addition or removal of functional groups (e.g. hydroxyl, methyl, glycosyl or acyl group) to SM structures, contribute to the huge diversity of structures, activities and functions of seed and plant SMs. This review summarizes available knowledge (up to 2023) on SM modifications in Brassicaceae and their contribution to SM plasticity. We give a comprehensive overview on enzymes involved in the addition or removal of these functional groups. Brassicaceae, including model (Arabidopsis thaliana) and crop (Brassica napus, Camelina sativa) plant species, present a large diversity of plant and seed SMs, which makes them valuable models to study SM modifications. In this review, particular attention is given to the environmental plasticity of SM and relative modification and/or decoration enzymes. Furthermore, a spotlight is given to SMs and related modification enzymes in seeds of Brassicaceae species. Seeds constitute a large reservoir of beneficial SMs and are one of the most important dietary sources, providing more than half of the world's intake of dietary proteins, oil and starch. The seed tissue- and stage-specific expressions of A. thaliana genes involved in SM modification are presented and discussed in the context of available literature. Given the major role in plant phytochemistry, biology and ecology, SM modifications constitute a subject of study contributing to the research and development in agroecology, pharmaceutical, cosmetics and food industrial sectors.
覆盖范围:截至 2023 年专门的代谢物(SM)修饰和/或装饰,相当于在 SM 结构上添加或去除官能团(如羟基、甲基、糖基或酰基),有助于种子和植物 SM 结构、活性和功能的巨大多样性。本综述总结了关于十字花科植物 SM 修饰的现有知识(截至 2023 年)及其对 SM 可塑性的贡献。我们全面概述了参与添加或去除这些功能基团的酶。十字花科植物,包括模式植物(拟南芥)和作物(油菜、荠菜),呈现出植物和种子 SM 的巨大多样性,这使它们成为研究 SM 修饰的宝贵模型。本综述特别关注 SM 的环境可塑性和相对修饰和/或装饰酶。此外,还重点介绍了十字花科物种种子中的 SMs 和相关修饰酶。种子蕴藏着大量有益的 SMs,是最重要的膳食来源之一,提供了全球一半以上的膳食蛋白质、油脂和淀粉摄入量。本文结合现有文献,介绍并讨论了参与 SM 修饰的 A. thaliana 基因在种子组织和阶段的特异性表达。鉴于 SM 在植物植物化学、生物学和生态学中的重要作用,SM 修饰是一个有助于农业生态学、制药、化妆品和食品工业部门研究和发展的研究课题。
{"title":"Specialized metabolite modifications in Brassicaceae seeds and plants: diversity, functions and related enzymes","authors":"Léa Barreda , Céline Brosse , Stéphanie Boutet , François Perreau , Loïc Rajjou , Loïc Lepiniec , Massimiliano Corso","doi":"10.1039/d3np00043e","DOIUrl":"10.1039/d3np00043e","url":null,"abstract":"<div><p>Covering: up to 2023</p></div><div><p>Specialized metabolite (SM) modifications and/or decorations, corresponding to the addition or removal of functional groups (<em>e.g.</em> hydroxyl, methyl, glycosyl or acyl group) to SM structures, contribute to the huge diversity of structures, activities and functions of seed and plant SMs. This review summarizes available knowledge (up to 2023) on SM modifications in Brassicaceae and their contribution to SM plasticity. We give a comprehensive overview on enzymes involved in the addition or removal of these functional groups. Brassicaceae, including model (<em>Arabidopsis thaliana</em>) and crop (<em>Brassica napus</em>, <em>Camelina sativa</em>) plant species, present a large diversity of plant and seed SMs, which makes them valuable models to study SM modifications. In this review, particular attention is given to the environmental plasticity of SM and relative modification and/or decoration enzymes. Furthermore, a spotlight is given to SMs and related modification enzymes in seeds of Brassicaceae species. Seeds constitute a large reservoir of beneficial SMs and are one of the most important dietary sources, providing more than half of the world's intake of dietary proteins, oil and starch. The seed tissue- and stage-specific expressions of <em>A. thaliana</em> genes involved in SM modification are presented and discussed in the context of available literature. Given the major role in plant phytochemistry, biology and ecology, SM modifications constitute a subject of study contributing to the research and development in agroecology, pharmaceutical, cosmetics and food industrial sectors.</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":"139696499","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}
Monoterpene indole alkaloids are the main sub-family of indole alkaloids with fascinating structures, stereochemistry, and diverse bioactivities (e.g., anticancer, anti-malarial and anti-arrhythmic etc.). Vallesamidine alkaloids and structurally more complex schizozygane alkaloids are small groups of rearranged monoterpene indole alkaloids with a unique 2,2,3-trialkylated indoline scaffold, while schizozygane alkaloids can generate a further rearranged skeleton, isoschizozygane, possessing a tetra-substituted, bridged tetrahydroquinoline core. In this review, the origin and structural features of vallesamidine and schizozygane alkaloids are introduced, and a discussion on the relationship of these alkaloids with aspidosperma alkaloids and a structural rearrangement hypothesis based on published studies is followed. Moreover, uncommon skeletons and potential bioactivities, such as anti-malarial and anti-tumour activities, make such alkaloids important synthetic targets, attracting research groups globally to accomplish total synthesis, resulting in impressive works on novel total synthesis, formal synthesis, and construction of key intermediates. These synthetic endeavours are systematically reviewed and highlighted with key strategies and efficiencies, providing different viewpoints on molecular structures and promoting the extension of chemical space and mining of new active scaffolds.
{"title":"Vallesamidine and schizozygane alkaloids: rearranged monoterpene indole alkaloids and synthetic endeavours","authors":"Xiangyu Zhang","doi":"10.1039/d3np00048f","DOIUrl":"10.1039/d3np00048f","url":null,"abstract":"<div><p>Covering 1963 to 2023</p></div><div><p>Monoterpene indole alkaloids are the main sub-family of indole alkaloids with fascinating structures, stereochemistry, and diverse bioactivities (<em>e.g.</em>, anticancer, anti-malarial and anti-arrhythmic <em>etc.</em>). Vallesamidine alkaloids and structurally more complex schizozygane alkaloids are small groups of rearranged monoterpene indole alkaloids with a unique 2,2,3-trialkylated indoline scaffold, while schizozygane alkaloids can generate a further rearranged skeleton, isoschizozygane, possessing a tetra-substituted, bridged tetrahydroquinoline core. In this review, the origin and structural features of vallesamidine and schizozygane alkaloids are introduced, and a discussion on the relationship of these alkaloids with aspidosperma alkaloids and a structural rearrangement hypothesis based on published studies is followed. Moreover, uncommon skeletons and potential bioactivities, such as anti-malarial and anti-tumour activities, make such alkaloids important synthetic targets, attracting research groups globally to accomplish total synthesis, resulting in impressive works on novel total synthesis, formal synthesis, and construction of key intermediates. These synthetic endeavours are systematically reviewed and highlighted with key strategies and efficiencies, providing different viewpoints on molecular structures and promoting the extension of chemical space and mining of new active scaffolds.</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":"139562646","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}
Since its initial disclosure in 1951, the Kornblum DeLaMare rearrangement has proved an important synthetic transformation and has been widely adopted as a biomimetic step in natural product synthesis. Utilising the base catalysed decomposition of alkyl peroxides to yield a ketone and alcohol has found use in many syntheses as well as a key strategic step, including the unmasking of furans, as a biomimetic synthetic tool, and the use of the rearrangement to install oxygen enantioselectively. Since ca. 1998, its impact as a synthetic transformation has grown significantly, especially given the frequency of use in natural product syntheses, therefore this 25 year time period will be the focus of the review.
{"title":"The Kornblum DeLaMare rearrangement in natural product synthesis: 25 years of innovation","authors":"Marc C. Kimber , Darren S. Lee","doi":"10.1039/d3np00058c","DOIUrl":"10.1039/d3np00058c","url":null,"abstract":"<div><p>Covering: 1998 up to the end of 2023</p></div><div><p>Since its initial disclosure in 1951, the Kornblum DeLaMare rearrangement has proved an important synthetic transformation and has been widely adopted as a biomimetic step in natural product synthesis. Utilising the base catalysed decomposition of alkyl peroxides to yield a ketone and alcohol has found use in many syntheses as well as a key strategic step, including the unmasking of furans, as a biomimetic synthetic tool, and the use of the rearrangement to install oxygen enantioselectively. Since <em>ca.</em> 1998, its impact as a synthetic transformation has grown significantly, especially given the frequency of use in natural product syntheses, therefore this 25 year time period will be the focus of the review.</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":"139641221","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}
Pan Luo , Jia-Hua Huang , Jian-Ming Lv , Gao-Qian Wang , Dan Hu , Hao Gao
Covering: up to August 2023
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.
{"title":"Biosynthesis of fungal terpenoids†","authors":"Pan Luo , Jia-Hua Huang , Jian-Ming Lv , Gao-Qian Wang , Dan Hu , 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}
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 via 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.
覆盖时间:2017年至2023年(现在)金丝桃科生物碱(AAs)是一类独特的含有杂环氮桥的特殊代谢物,在高等植物中发挥着独特的作用。无论其结构如何变化,大多数 AAs 都是通过分子内氧化偶联进行生物合成的。随着天然产物化学、合成有机化学、生物化学、系统和合成生物学工具及应用的发展,人们对生物合成途径的复杂组织结构不断有新的认识。这些工具和应用促进了新型化合物的鉴定、痕量级代谢物的定量、合成以及参与 AA 催化的酶的表征,从而使生物合成途径得以识别。从长远来看,对途径的全面了解有利于生物技术的应用。本综述强调了参与生物合成的 AA 专化代谢物的结构多样性,尽管这一过程尚未完全明确。此外,这项工作还强调了合成和对映体选择性研究在证明生物合成结论方面的关键作用。它们作为抗病毒药物发现的先导成分的潜在候选资格也已确立。然而,要全面了解这一途径,还需要进一步的跨学科努力,在抗病毒研究中解决结构与活性的关系问题。本综述介绍了目前有关这一主题的知识。
{"title":"Unveiling Amaryllidaceae alkaloids: from biosynthesis to antiviral potential – a review","authors":"Thilina U. Jayawardena , Natacha Merindol , Nuwan Sameera Liyanage , 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}
Covering 2016 up to the end of 2023Alpinia is the largest genus of flowering plants in the ginger family, Zingiberaceae, and comprises about 500 species. Many Alpinia 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 Alpinia species reported from 2016 through 2023, including newly isolated compounds and potential biological effects. The present review article shows that Alpinia species have a wide spectrum of pharmacological activities, most due to the activities of diarylheptanoids, terpenoids, flavonoids, and phenolics.
{"title":"Phytochemical and pharmacological properties of the genus <i>Alpinia</i> from 2016 to 2023.","authors":"Isoo Youn, Ah-Reum Han, Donglan Piao, Hwaryeong Lee, Hyunkyung Kwak, Yeju Lee, Joo-Won Nam, Eun Kyoung Seo","doi":"10.1039/d4np00004h","DOIUrl":"https://doi.org/10.1039/d4np00004h","url":null,"abstract":"<p><p>Covering 2016 up to the end of 2023<i>Alpinia</i> is the largest genus of flowering plants in the ginger family, Zingiberaceae, and comprises about 500 species. Many <i>Alpinia</i> 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 <i>Alpinia</i> species reported from 2016 through 2023, including newly isolated compounds and potential biological effects. The present review article shows that <i>Alpinia</i> 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":11.9,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","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":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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.
{"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":"https://doi.org/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":11.9,"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}