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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-24 DOI: 10.1039/d3np00013c
Vsevolod Dubovik , Anna Dalinova , Alexander Berestetskiy

Covering: 2012 to 2022

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.

涵盖范围:2012年至2022年,十元内酯(TML)是一组有趣而多样的天然聚酮,在真菌中含量丰富,在细菌、海洋生物和昆虫中含量较低。TML以其表现出广泛生物活性的能力而闻名,包括植物毒性、细胞毒性、抗真菌、抗菌等。然而,世界各地具有不同兴趣的科学团体对这些化合物的随机发现,导致了关于它们在不同生物体中的分布及其生物活性的不完整信息。因此,尽管有60多年的研究历史,但对TML的自然来源、结构类型分类和最具特征的生物活性仍然没有共识。有争议的命名法、不正确或错误的结构阐明、对产生生物体的鉴定不力以及关于化合物生物活性的零散信息——所有这些因素都导致了TML的去复制和定向搜索问题。本综述由两部分组成:第一部分(第2节)涵盖了2012年至2022年间(在上一篇综述发表后)发表的104个天然TML,第二部分(第3节)总结了1964-2022年间描述的214个TML的信息,因此强调了这些有趣的天然产物研究中的主要问题和趋势。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-24 DOI: 10.1039/d3np00022b
Jun Luo , Danyang Zhang , Pengfei Tang , Nan Wang , Shuai Zhao , Lingyi Kong

Covering: 1925 to July 2023

Among the sesquiterpenoids with rich structural diversity and potential bioactivities, lindenane sesquiterpenoids (LSs) possess a characteristic cis, trans-3,5,6-carbocyclic skeleton and mainly exist as monomers and diverse oligomers in plants from the Lindera genus and Chloranthaceae family. Since the first identification of lindeneol from Lindera strychnifolia 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.

覆盖范围:1925年-2023年7月在具有丰富结构多样性和潜在生物活性的倍半萜类化合物中,lindenane倍半萜(LSs)具有独特的顺式、反式-3,5,6-碳环骨架,主要以单体和多种低聚物的形式存在于Lindera属和Chlorantheaceae科植物中。自1925年首次从马钱子中鉴定出lindeneol以来,已发现354种具有抗炎、抗肿瘤和抗感染活性的天然LSs及其低聚物。在结构上,三分之二的LSs以具有有趣骨架的低聚物的形式存在,通过不同的聚合物模式,特别是Diels-Alder[4+2]环加成。合成化学家被其多样的生物活性和有趣的多环结构所吸引,近几十年来一直致力于天然LSs的全合成。本文系统、全面地总结了1925年至2023年7月LSs的相关研究成果,重点介绍了LSs的结构分类、化学合成和生物活性,这将有助于LSs及其低聚物的进一步研究。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-24 DOI: 10.1039/d3np00036b
Evan T. Miller , Oleg V. Tsodikov , Sylvie Garneau-Tsodikova

Covering: 2009 up to August 2023

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.

涵盖范围:2009年至2020年8月,丙基转移酶(PT)参与植物、细菌和真菌的初级和次级代谢,是许多临床相关天然产物(NP)生物合成的关键酶。在过去的二十年里,可溶性二甲基烯丙基色氨酸合成酶(DMATS)PT的持续生化和结构表征揭示了这些酶作为化学酶促合成新型药物先导的生物催化剂的重要前景。这是对DMATS的全面综述,描述了形成这些酶的机制基础的结构-功能关系,以及这些知识在DMATS工程中的应用。我们总结了过去14年(2009-2023年)这些研究的主要发现和经验教训。此外,我们还发现了目前我们对这些迷人酶的理解存在的差距。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-24 DOI: 10.1039/d3np00029j
Bichu Cheng , Lili Song , Fener Chen

Covering: up to 2023

Huperzine alkaloids are a group of natural products belonging to the Lycopodium 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.

涵盖范围:高达2023超级嗪生物碱是石松生物碱家族的一组天然产物。石杉碱A具有独特的结构,对乙酰胆碱酯酶(AChE)具有较强的抑制活性。该生物碱亚家族为开发合成方法和不对称合成提供了巨大的机会。石杉碱A的合成已形成数十种全合成方法和丰富的新化学体系。在合成其他石杉碱生物碱方面也取得了令人印象深刻的进展。在过去的十年中,人们报道了石杉碱B、U、O、Q和R的全合成,以及石杉碱K、M和N的结构重排和全合成。本文对石杉碱类化合物的合成有机化学、生物合成及药用化学进行了综述。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-24 DOI: 10.1039/d3np00012e
Zhanpin Zhu , Ruibing Chen , Lei Zhang

Covering: 2000 to 2023

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.

涵盖范围:2000-2023单苯基丙烷是一大类具有伯C6-C3骨架的天然产物。它们不仅是植物生长的重要生物分子,也是高价值行业的关键化学品,包括香料、营养品、生物材料和制药。然而,随着全球对简单苯丙烷类化合物的需求不断增长,直接植物提取或化学合成在产量、滴定度、成本和环境影响方面往往难以满足当前的需求。得益于代谢工程和合成生物学的快速发展,微生物从廉价可再生资源中生产天然产品为可持续供应提供了可行的解决方案。这篇综述概述了简单苯丙烷类化合物的生物活性,比较了它们在不同物种(植物、细菌和真菌)中的生物合成途径,并总结了过去十年中微生物生产简单苯丙烷的关键研究,重点是似乎最有潜力进一步开发的工程策略。此外,还提出了解决苯丙烷类化合物工业生产当前挑战的建设性解决方案和未来前景。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-01
Hyun Woo Kim , Jin Woo Lee , Sang Hee Shim

Correction for ‘Biosynthesis, biological activities, and structure–activity relationships of decalin-containing tetramic acid derivatives isolated from fungi’ by Hyun Woo Kim et al., Nat. Prod. Rep., 2024, https://doi.org/10.1039/d4np00013g.

Hyun Woo Kim 等人撰写的 "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 "的更正,Nat.Rep., 2024, .Rep., 2024, https://doi.org/10.1039/d4np00013g.
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引用次数: 0
Correction: Hot off the Press 更正:热销
IF 11.9 1区 化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-01 DOI: 10.1039/d3np90056h
Robert A. Hill , Andrew Sutherland

Correction for ‘Hot off the Press’ by Robert A. Hill et al., Nat. Prod. Rep., 2023, 40, 1816–1821, https://doi.org/10.1039/d3np90052e.

罗伯特-A-希尔等人撰写的《新闻热点》的更正,Nat.Rep., 2023, 40, 1816-1821, .Rep., 2023, 40, 1816-1821, https://doi.org/10.1039/d3np90052e.
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-01
Kate M. J. de Mattos-Shipley , Thomas J. Simpson
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 et al., Nat. Prod. Rep., 2023, 40, 174–201, https://doi.org/10.1039/D2NP00040G.
对 Kate M. J. de Mattos-Shipley 等人在 Nat.Rep.Rep., 2023, 40, 174-201, https://doi.org/10.1039/D2NP00040G。
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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 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2024-01-01 DOI: 10.1039/d4np90001d
Alexandre Maciuk , Dominique Mazier , Romain Duval

Correction for ‘Future antimalarials from Artemisia? A rationale for natural product mining against drug-refractory Plasmodium stages’ by Alexandre Maciuk et al., Nat. Prod. Rep., 2023, 40, 1130–1144, https://doi.org/10.1039/D3NP00001J.

对 Alexandre Maciuk 等人在 Nat.Nat.杂志上发表的 "来自青蒿的未来抗疟药?针对难治性疟原虫阶段的天然产品开采原理 "的更正,作者 Alexandre Maciuk 等人,Nat.Rep.Rep., 2023, 40, 1130-1144, https://doi.org/10.1039/D3NP00001J。
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引用次数: 0
Hot off the Press 刚出版的。
IF 11.9 1区 化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY Pub Date : 2023-12-04 DOI: 10.1039/D3NP90052E
Robert A. Hill and Andrew Sutherland

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 Alstonia scholaris.

个人选择了32篇最近的论文,涵盖了生物有机化学和新型天然产物(如Alstonia scholaris的alscholarine A)的当前发展的各个方面。
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引用次数: 0
期刊
Natural Product Reports
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