Natural Product Reports最新文献

英文中文

Modulators of the ubiquitin–proteasome system from natural products: chemical structures and their potential for drug discovery 天然产物中泛素-蛋白酶体系统的调节剂：化学结构及其药物发现的潜力。

IF 10.6 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-17 DOI: 10.1039/d5np00004a

Yuki Hitora , Sachiko Tsukamoto

Covering: up to 2024

The ubiquitin–proteasome system (UPS) plays a key role in regulating intracellular protein degradation and maintaining cellular homeostasis. Within the UPS, target proteins are polyubiquitinated through sequential reactions catalyzed by ubiquitination-related enzymes. These ubiquitinated proteins are then recognized and degraded by the 26S proteasome. Deubiquitinating enzymes cleave the formed polyubiquitin chains and regulate protein degradation, thereby contributing to precise regulation of the system. Dysregulation of the UPS is associated with cancer, immune disorders, and neurodegenerative diseases, making it a potential target for drug discovery. To date, a variety of natural products that target the UPS have been discovered and used in pharmaceutical development, and these compounds have provided important insights into the molecular mechanisms of UPS regulation. This review describes natural products that inhibit protein degradation in the UPS and activate protein degradation mediated by the 20S proteasome, thus clarifying their mechanisms of action and exploring their potential applications as therapeutic agents.

泛素-蛋白酶体系统（ubiquitin-proteasome system， UPS）在调节细胞内蛋白降解和维持细胞稳态中起着关键作用。在UPS中，目标蛋白通过泛素化相关酶催化的序列反应被多泛素化。这些泛素化蛋白随后被26S蛋白酶体识别和降解。去泛素化酶切割形成的多泛素链并调节蛋白质降解，从而有助于系统的精确调节。UPS的失调与癌症、免疫紊乱和神经退行性疾病有关，使其成为药物发现的潜在靶点。迄今为止，各种针对UPS的天然产物已经被发现并用于药物开发，这些化合物为UPS调节的分子机制提供了重要的见解。本文综述了抑制UPS蛋白降解和激活20S蛋白酶体介导的蛋白降解的天然产物，从而阐明了它们的作用机制，并探索了它们作为治疗药物的潜在应用前景。

{"title":"Modulators of the ubiquitin–proteasome system from natural products: chemical structures and their potential for drug discovery","authors":"Yuki Hitora , Sachiko Tsukamoto","doi":"10.1039/d5np00004a","DOIUrl":"10.1039/d5np00004a","url":null,"abstract":"<div><div>Covering: up to 2024</div></div><div><div>The ubiquitin–proteasome system (UPS) plays a key role in regulating intracellular protein degradation and maintaining cellular homeostasis. Within the UPS, target proteins are polyubiquitinated through sequential reactions catalyzed by ubiquitination-related enzymes. These ubiquitinated proteins are then recognized and degraded by the 26S proteasome. Deubiquitinating enzymes cleave the formed polyubiquitin chains and regulate protein degradation, thereby contributing to precise regulation of the system. Dysregulation of the UPS is associated with cancer, immune disorders, and neurodegenerative diseases, making it a potential target for drug discovery. To date, a variety of natural products that target the UPS have been discovered and used in pharmaceutical development, and these compounds have provided important insights into the molecular mechanisms of UPS regulation. This review describes natural products that inhibit protein degradation in the UPS and activate protein degradation mediated by the 20S proteasome, thus clarifying their mechanisms of action and exploring their potential applications as therapeutic agents.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 7","pages":"Pages 1120-1135"},"PeriodicalIF":10.6,"publicationDate":"2025-04-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143958516","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

Recent advances in the chemistry and biology of plant oxylipin hormones 植物氧脂素激素的化学和生物学研究进展。

IF 10.6 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-17 DOI: 10.1039/d5np00006h

Yuho Nishizato , Taichi Okumura , Kotaro Matsumoto , Minoru Ueda

Jasmonates, including jasmonic acid (JA) and its derivatives, are lipid-based signaling molecules critical for plant growth, development, and defense. Among these, jasmonoyl-l-isoleucine (JA-Ile) has been identified as a bioactive plant hormone that mediates various physiological responses. JA-Ile functions in planta as a ‘molecular glue’ in protein–protein associations to induce the defense-related gene expression for plant–pathogen and plant–insect communications, and it affects many aspects of plant development and stress responses. This review explores the historical journey of jasmonate research, emphasizing the discovery of JA-Ile, its biosynthesis, function as a molecular glue, and the ligand–receptor co-evolutional aspect. The elucidation of the SCFCOI1-JAZ receptor complex and the crystallization of this co-receptor system marked significant advancements in understanding the chemical background of jasmonate biology. This review focuses on the advances in the chemistry and biology of jasmonate bioscience in the past two decades.

茉莉酸盐，包括茉莉酸（JA）及其衍生物，是基于脂质的信号分子，对植物生长、发育和防御至关重要。其中，茉莉异亮氨酸（JA-Ile）是一种具有生物活性的植物激素，可介导多种生理反应。JA-Ile在植物中作为蛋白-蛋白结合的“分子胶”，诱导植物-病原体和植物-昆虫交流的防御相关基因表达，并影响植物发育和胁迫反应的许多方面。本文综述了茉莉酸盐研究的历史历程，重点介绍了JA-Ile的发现、其生物合成、分子胶的功能以及配体-受体的共同进化等方面。SCFCOI1-JAZ受体复合物的阐明和该共受体系统的结晶标志着对茉莉酸生物学化学背景的理解取得了重大进展。本文综述了近二十年来茉莉酸盐生物科学在化学和生物学方面的研究进展。

引用次数: 0

The bisintercalator family of nonribosomal peptides: structural diversity and biosynthetic mechanism 非核糖体肽双插层体家族：结构多样性和生物合成机制。

IF 10.6 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-17 DOI: 10.1039/d5np00003c

Xinjie Shi

Covering: up to February 2025

Among the numerous bioactive microbial natural products, a subset of nonribosomal peptides derived from actinobacteria is characterized by their C₂-symmetric macrocyclic scaffolds and referred to as bisintercalators due to their ability to bisintercalate into DNA molecules. This family of compounds exhibits excellent antimicrobial, antitumor and antiviral properties, making them promising candidates for drug development. New members of the bisintercalator family continue to be discovered, and significant advancement has been made in understanding their biosynthesis over the past two decades. These efforts have established the general biosynthetic pathways of bisintercalators, although some chemically intriguing enzymatic transformations remain to be fully elucidated. This review summarizes the sources and chemical structures of known bisintercalators, briefly discussing their bioactivities, and then highlights the biochemical reactions involved in assembling their sophisticated macrocyclic scaffolds.

在众多具有生物活性的微生物天然产物中，来源于放线菌的非核糖体肽的一个子集以其c2对称的大环支架为特征，由于其双插入DNA分子的能力而被称为双插子。该家族化合物具有优异的抗菌、抗肿瘤和抗病毒特性，使其成为药物开发的有希望的候选者。双插层化合物家族的新成员不断被发现，并且在过去二十年中对其生物合成的理解取得了重大进展。这些努力已经建立了双插层剂的一般生物合成途径，尽管一些化学上有趣的酶转化仍有待充分阐明。本文综述了已知双插入物的来源和化学结构，简要讨论了它们的生物活性，并重点介绍了组装它们的复杂大环支架所涉及的生化反应。

引用次数: 0

Unlocking marine treasures: isolation and mining strategies of natural products from sponge-associated bacteria† 解锁海洋宝藏：从海绵相关细菌中分离和开采天然产物的策略。

IF 10.6 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-17 DOI: 10.1039/d5np00013k

Jeong-A. Kim , Si-sun Choi , Jae Kyu Lim , Eung-Soo Kim

Covering: 2019 to early 2025

Marine sponges form unique ecosystems through symbiosis with diverse microbial communities, producing natural products including bioactive compounds. This review comprehensively addresses the key steps in the discovery of natural products from sponge-associated microorganisms, encompassing microbial isolation and cultivation, compound identification, and characterisation. Various cultivation methods, such as floating filter cultivation, microcapsule-based cultivation, and in situ systems, are examined to highlight their applications and strategies for overcoming limitations of conventional approaches. Additionally, the integration of genome-based methodologies and compound screening is explored to enhance the discovery of novel bioactive substances and establish a sustainable platform for natural product research. This review provides insights into the latest trends in sponge-associated microbial research and offers practical perspectives for expanding the utilization of marine biological resources.

海洋海绵通过与不同微生物群落的共生形成独特的生态系统，产生包括生物活性化合物在内的天然产物。本文综述了从海绵相关微生物中发现天然产物的关键步骤，包括微生物分离和培养、化合物鉴定和表征。各种培养方法，如浮动过滤培养，微胶囊为基础的培养，并在原位系统进行了审查，以突出其应用和策略，以克服传统方法的局限性。此外，我们还探索了基于基因组的方法和化合物筛选的整合，以加强新的生物活性物质的发现，并建立一个可持续的天然产物研究平台。本文综述了海绵相关微生物研究的最新动态，为扩大海洋生物资源的利用提供了实践展望。

引用次数: 0

Configurational assignments of type-I polyketide synthase (PKS)-derived natural products based on spectroscopic and chemical analysis: methodologies and case studies 基于光谱和化学分析的i型聚酮合成酶（PKS）衍生天然产物的构型分配：方法和案例研究。

IF 10.6 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-17 DOI: 10.1039/d4np00061g

Jinsheng Cui , Prima F. Hillman , Geum Jin Kim , Thinh T. M. Bui , Kyuho Moon , Sang-Jip Nam , Hyukjae Choi , Dong-Chan Oh

Covering: 1992 to 2024

Type-I polyketide synthase (PKS)-derived metabolites are structurally diverse bioactive natural products containing multiple stereogenic centres. This review focuses on the configurational analysis of type-I PKS-derived natural products, emphasizing the methodologies and challenges associated with determining their stereochemistry due to their complex structures with multiple chiral centres. Key strategies include J-based configuration analysis (JBCA), chemical derivatizations with chiral reagents, degradation methods, NMR spectroscopic analysis, and the exploitation of chiroptical properties. Case studies demonstrate the practical applications of these methods in elucidating the stereochemistry of type-I polyketide natural products.

i型聚酮合成酶（PKS）衍生的代谢物是结构多样的生物活性天然产物，含有多个立体中心。本文综述了1型pks衍生的天然产物的构型分析，强调了由于其具有多个手性中心的复杂结构而确定其立体化学的方法和挑战。关键策略包括基于j的构型分析（JBCA）、手性试剂的化学衍生化、降解方法、核磁共振光谱分析和手性特性的开发。实例研究证明了这些方法在阐明i型聚酮天然产物立体化学中的实际应用。

引用次数: 0

40 Years of Natural Product Reports 40年的天然产品报告。

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-04-09 DOI: 10.1039/D5NP90012C

A graphical abstract is available for this content

此内容的图形摘要可用

引用次数: 0

Illuminating the dark space of bioactive peptides with mass spectrometry 用质谱法照亮生物活性肽的黑暗空间。

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-03-11 DOI: 10.1039/D4NP00057A

Nicole C. Parsley and Leslie M. Hicks

Natural product peptides embody a suite of inherent bioactivities and serve as a template to inspire new chemistries and molecular scaffolds in drug discovery and agrotechnology. Mapping the vast and diverse bioactive peptidome, however, is largely obfuscated by unpredictable molecular transformations in both non-ribosomal sequences and highly post-translationally modified ribosomal protein products. Mass spectrometry is a powerful analytical technique with modern instrumentation achieving unprecedented resolving power, rapid and sensitive gas-phase separations, and versatile multistage fragmentation techniques. As such, mass spectrometry can be (1) leveraged to characterize traditionally difficult-to-sequence natural product peptide modifications via enhanced gas-phase technologies and (2) coupled with complementary ‘Omics’ approaches to predict peptide structure through transcripts, motifs, biosynthetic pathways, and the biomolecular machinery involved in peptide biogenesis. Herein, the challenges of and recent innovations in mass spectrometry towards the discovery and characterization of natural product bioactive peptides are profiled.

天然产物多肽包含一套固有的生物活性，并作为模板在药物发现和农业技术中激发新的化学和分子支架。然而，在非核糖体序列和高度翻译后修饰的核糖体蛋白产物中，不可预测的分子转化在很大程度上混淆了大量多样的生物活性肽dome的定位。质谱分析是一种强大的分析技术，现代仪器实现了前所未有的分辨率，快速和敏感的气相分离，以及多功能多级破碎技术。因此，质谱可以(1)通过增强的气相技术来表征传统上难以测序的天然产物肽修饰；(2)结合互补的“组学”方法，通过转录本、基序、生物合成途径和肽生物发生中涉及的生物分子机制来预测肽结构。本文介绍了质谱法在发现和表征天然产物生物活性肽方面所面临的挑战和最新的创新。

{"title":"Illuminating the dark space of bioactive peptides with mass spectrometry","authors":"Nicole C. Parsley and Leslie M. Hicks","doi":"10.1039/D4NP00057A","DOIUrl":"10.1039/D4NP00057A","url":null,"abstract":"<p >Natural product peptides embody a suite of inherent bioactivities and serve as a template to inspire new chemistries and molecular scaffolds in drug discovery and agrotechnology. Mapping the vast and diverse bioactive peptidome, however, is largely obfuscated by unpredictable molecular transformations in both non-ribosomal sequences and highly post-translationally modified ribosomal protein products. Mass spectrometry is a powerful analytical technique with modern instrumentation achieving unprecedented resolving power, rapid and sensitive gas-phase separations, and versatile multistage fragmentation techniques. As such, mass spectrometry can be (1) leveraged to characterize traditionally difficult-to-sequence natural product peptide modifications <em>via</em> enhanced gas-phase technologies and (2) coupled with complementary ‘Omics’ approaches to predict peptide structure through transcripts, motifs, biosynthetic pathways, and the biomolecular machinery involved in peptide biogenesis. Herein, the challenges of and recent innovations in mass spectrometry towards the discovery and characterization of natural product bioactive peptides are profiled.</p>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":" 6","pages":" 950-955"},"PeriodicalIF":10.2,"publicationDate":"2025-03-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.rsc.org/en/content/articlepdf/2025/np/d4np00057a?page=search","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143603231","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

Privileged natural product compound classes for anti-inflammatory drug development 开发抗炎药物的天然产物化合物类。

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-03-03 DOI: 10.1039/d4np00066h

Malcolm Z. Y. Choo , Julian A. T. Chua , Sean X. Y. Lee , Yuet Ang , W. S. Fred Wong , Christina L. L. Chai

Covering: up to early 2025

Privileged compound classes of anti-inflammatory natural products are those where there are many reported members that possess anti-inflammatory properties. The identification of these classes is of particular relevance to drug discovery, as they could serve as valuable starting points in developing effective and safe anti-inflammatory agents. The privileged compound classes of natural products include the polyphenols, coumarins, labdane diterpenoids, sesquiterpene lactones, isoquinoline and indole alkaloids, each offering a variety of molecular scaffolds and functional groups that enable diverse interactions with biological targets. From a medicinal chemistry point of view, natural products are both a boon and a bane. The multi-targeting nature of natural products is a boon in the treatment of multi-factorial diseases such as inflammation, but promiscuity, poor potency and pharmacokinetic properties are significant hurdles that must be addressed to ensure these compounds can be effectively used as therapeutics. In addition, there are continued controversies regarding the efficacies of some of these natural products that will continue to polarise their use. In this review, examples of natural products of six privileged compound classes will be discussed for their potential use and possible further development as anti-inflammatory drugs.

覆盖范围：到2025年初，抗炎天然产品的特权化合物类别是那些有许多报告成员具有抗炎特性的化合物。这些类别的鉴定与药物发现特别相关，因为它们可以作为开发有效和安全的抗炎药的有价值的起点。天然产物的特权化合物类别包括多酚，香豆素，labdane二萜，倍半萜内酯，异喹啉和吲哚生物碱，每一种都提供了各种分子支架和功能基团，能够与生物靶标进行不同的相互作用。从药物化学的角度来看，天然产物既是一种恩惠也是一种祸害。天然产物的多靶点特性在治疗多因素疾病（如炎症）方面是一个福音，但滥交、效力差和药代动力学特性是必须解决的重大障碍，以确保这些化合物可以有效地用作治疗药物。此外，关于其中一些天然产品的功效仍存在争议，这将继续使它们的使用两极分化。本文综述了六种特殊化合物类别的天然产物，讨论了它们作为抗炎药物的潜在用途和进一步开发的可能性。

{"title":"Privileged natural product compound classes for anti-inflammatory drug development","authors":"Malcolm Z. Y. Choo , Julian A. T. Chua , Sean X. Y. Lee , Yuet Ang , W. S. Fred Wong , Christina L. L. Chai","doi":"10.1039/d4np00066h","DOIUrl":"10.1039/d4np00066h","url":null,"abstract":"<div><div>Covering: up to early 2025</div></div><div><div>Privileged compound classes of anti-inflammatory natural products are those where there are many reported members that possess anti-inflammatory properties. The identification of these classes is of particular relevance to drug discovery, as they could serve as valuable starting points in developing effective and safe anti-inflammatory agents. The privileged compound classes of natural products include the polyphenols, coumarins, labdane diterpenoids, sesquiterpene lactones, isoquinoline and indole alkaloids, each offering a variety of molecular scaffolds and functional groups that enable diverse interactions with biological targets. From a medicinal chemistry point of view, natural products are both a boon and a bane. The multi-targeting nature of natural products is a boon in the treatment of multi-factorial diseases such as inflammation, but promiscuity, poor potency and pharmacokinetic properties are significant hurdles that must be addressed to ensure these compounds can be effectively used as therapeutics. In addition, there are continued controversies regarding the efficacies of some of these natural products that will continue to polarise their use. In this review, examples of natural products of six privileged compound classes will be discussed for their potential use and possible further development as anti-inflammatory drugs.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 5","pages":"Pages 856-875"},"PeriodicalIF":10.2,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143595763","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

Molecular insights fast-tracked: AI in biosynthetic pathway research 分子洞察快速追踪：人工智能在生物合成途径研究中的应用。

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-03-03 DOI: 10.1039/d4np00003j

Lijuan Liao , Mengjun Xie , Xiaoshan Zheng , Zhao Zhou , Zixin Deng , Jiangtao Gao

Covering: 2000 to 2025

This review explores the potential of artificial intelligence (AI) in addressing challenges and accelerating molecular insights in biosynthetic pathway research, which is crucial for developing bioactive natural products with applications in pharmacology, agriculture, and biotechnology. It provides an overview of various AI techniques relevant to this research field, including machine learning (ML), deep learning (DL), natural language processing, network analysis, and data mining. AI-powered applications across three main areas, namely, pathway discovery and mining, pathway design, and pathway optimization, are discussed, and the benefits and challenges of integrating omics data and AI for enhanced pathway research are also elucidated. This review also addresses the current limitations, future directions, and the importance of synergy between AI and experimental approaches in unlocking rapid advancements in biosynthetic pathway research. The review concludes with an evaluation of AI's current capabilities and future outlook, emphasizing the transformative impact of AI on biosynthetic pathway research and the potential for new opportunities in the discovery and optimization of bioactive natural products.

本综述探讨了人工智能（AI）在解决生物合成途径研究中的挑战和加速分子洞察方面的潜力，这对于开发具有生物活性的天然产品在药理学、农业和生物技术中的应用至关重要。它概述了与该研究领域相关的各种人工智能技术，包括机器学习（ML）、深度学习（DL）、自然语言处理、网络分析和数据挖掘。本文讨论了三个主要领域的人工智能应用，即途径发现和挖掘、途径设计和途径优化，并阐明了整合组学数据和人工智能以增强途径研究的好处和挑战。这篇综述还讨论了当前的局限性、未来的方向，以及人工智能和实验方法之间的协同作用对解锁生物合成途径研究的快速进展的重要性。本文最后对人工智能的当前能力和未来前景进行了评估，强调了人工智能对生物合成途径研究的变革性影响，以及在发现和优化生物活性天然产物方面的新机遇。

{"title":"Molecular insights fast-tracked: AI in biosynthetic pathway research","authors":"Lijuan Liao , Mengjun Xie , Xiaoshan Zheng , Zhao Zhou , Zixin Deng , Jiangtao Gao","doi":"10.1039/d4np00003j","DOIUrl":"10.1039/d4np00003j","url":null,"abstract":"<div><div>Covering: 2000 to 2025</div></div><div><div>This review explores the potential of artificial intelligence (AI) in addressing challenges and accelerating molecular insights in biosynthetic pathway research, which is crucial for developing bioactive natural products with applications in pharmacology, agriculture, and biotechnology. It provides an overview of various AI techniques relevant to this research field, including machine learning (ML), deep learning (DL), natural language processing, network analysis, and data mining. AI-powered applications across three main areas, namely, pathway discovery and mining, pathway design, and pathway optimization, are discussed, and the benefits and challenges of integrating omics data and AI for enhanced pathway research are also elucidated. This review also addresses the current limitations, future directions, and the importance of synergy between AI and experimental approaches in unlocking rapid advancements in biosynthetic pathway research. The review concludes with an evaluation of AI's current capabilities and future outlook, emphasizing the transformative impact of AI on biosynthetic pathway research and the potential for new opportunities in the discovery and optimization of bioactive natural products.</div></div>","PeriodicalId":94,"journal":{"name":"Natural Product Reports","volume":"42 5","pages":"Pages 911-936"},"PeriodicalIF":10.2,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143699074","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

Recent advances in the application of the isoxazoline route to aldols in the synthesis of natural products 异恶唑啉路线合成醛醇在天然产物中的应用进展。

IF 10.2 1区化学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Natural Product Reports

Pub Date : 2025-03-03 DOI: 10.1039/d4np00069b

Pavel Yu. Ushakov , Alexey Yu. Sukhorukov

Covering: 2000 to 2024

The cycloaddition of nitrile oxides with olefins (NOC), followed by reductive cleavage of the resulting isoxazolines, has been widely recognised as a convenient and powerful synthetic strategy for constructing the aldol motif in natural product synthesis. Different modes of NOC (intermolecular, fused and bridged intramolecular) enable the synthesis of diverse isoxazoline products, which can be converted into highly substituted cyclic and acyclic aldol frameworks. This review examines the advances in this field over the past 25 years. More than 50 total syntheses are discussed, encompassing various classes of natural compounds, including macrolides, alkaloids, terpenoids, steroids, pseudosugars, sulfolipids and some others. Moreover, the basic aspects of this methodology are outlined, including methods for the generation of nitrile oxides and isoxazoline ring cleavage, as well as stereochemical models for intramolecular nitrile oxide cycloaddition.

在天然产物合成中，丙烯腈氧化物与烯烃（NOC）的环加成，然后是所得到的异恶唑啉的还原裂解，已被广泛认为是构建醛醇基序的一种方便而有效的合成策略。不同的NOC模式（分子间、熔融和分子内桥接）可以合成不同的异恶唑啉产物，这些产物可以转化为高取代的环和无环醛醇框架。本文综述了过去25年来该领域的研究进展。讨论了50多种全合成方法，包括各种天然化合物，包括大环内酯类、生物碱类、萜类、类固醇、假糖、亚脂类等。此外，概述了该方法的基本方面，包括生成腈氧化物和异恶唑啉环裂解的方法，以及分子内腈氧化物环加成的立体化学模型。

引用次数: 0

首页上一页

下一页尾页

类型

全部化学•材料生命科学医学物理工程技术环境•农林材料科学地球科学法学管理学化学环境科学与生态学计算机科学教育学经济学农林科学人文科学生物学数学物理与天体物理心理学综合性期刊其他工业工程理学历史学农学文学信息工程

数据库

全部 ACS Publications Elsevier ieeexplore Springer The Royal Society of Chemistry Wiley

期刊

Natural Product Reports

全部 Acc. Chem. Res. ACS Applied Bio Materials ACS Appl. Electron. Mater. ACS Appl. Energy Mater. ACS Appl. Mater. Interfaces ACS Appl. Nano Mater. ACS Appl. Polym. Mater. ACS BIOMATER-SCI ENG ACS Catal. ACS Cent. Sci. ACS Chem. Biol. ACS Chemical Health & Safety ACS Chem. Neurosci. ACS Comb. Sci. ACS Earth Space Chem. ACS Energy Lett. ACS Infect. Dis. ACS Macro Lett. ACS Mater. Lett. ACS Med. Chem. Lett. ACS Nano ACS Omega ACS Photonics ACS Sens. ACS Sustainable Chem. Eng. ACS Synth. Biol. Anal. Chem. BIOCHEMISTRY-US Bioconjugate Chem. BIOMACROMOLECULES Chem. Res. Toxicol. Chem. Rev. Chem. Mater. CRYST GROWTH DES ENERG FUEL Environ. Sci. Technol. Environ. Sci. Technol. Lett. Eur. J. Inorg. Chem. IND ENG CHEM RES Inorg. Chem. J. Agric. Food. Chem. J. Chem. Eng. Data J. Chem. Educ. J. Chem. Inf. Model. J. Chem. Theory Comput. J. Med. Chem. J. Nat. Prod. J PROTEOME RES J. Am. Chem. Soc. LANGMUIR MACROMOLECULES Mol. Pharmaceutics Nano Lett. Org. Lett. ORG PROCESS RES DEV ORGANOMETALLICS J. Org. Chem. J. Phys. Chem. J. Phys. Chem. A J. Phys. Chem. B J. Phys. Chem. C J. Phys. Chem. Lett. Analyst Anal. Methods Biomater. Sci. Catal. Sci. Technol. Chem. Commun. Chem. Soc. Rev. CHEM EDUC RES PRACT CRYSTENGCOMM Dalton Trans. Energy Environ. Sci. ENVIRON SCI-NANO ENVIRON SCI-PROC IMP ENVIRON SCI-WAT RES Faraday Discuss. Food Funct. Green Chem. Inorg. Chem. Front. Integr. Biol. J. Anal. At. Spectrom. J. Mater. Chem. A J. Mater. Chem. B J. Mater. Chem. C Lab Chip Mater. Chem. Front. Mater. Horiz. MEDCHEMCOMM Metallomics Mol. Biosyst. Mol. Syst. Des. Eng. Nanoscale Nanoscale Horiz. Nat. Prod. Rep. New J. Chem. Org. Biomol. Chem. Org. Chem. Front. PHOTOCH PHOTOBIO SCI PCCP Polym. Chem.

﹀