Journal of Natural Products 最新文献_第4页

Addition to "Natural and Semisynthetic Chalcones as Dual FLT3 and Microtubule Polymerization Inhibitors". 添加到 "作为 FLT3 和微管聚合双重抑制剂的天然和半合成查耳酮"。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-11 DOI: 10.1021/acs.jnatprod.4c01252

Haleema Sadia Malik, Aishah Bilal, Rahim Ullah, Maheen Iqbal, Sardraz Khan, Ishtiaq Ahmed, Karsten Krohn, Rahman Shah Zaib Saleem, Hidayat Hussain, Amir Faisal

引用次数: 0

Nonenzymatic Sequestering of Formaldehyde into the Antibiotic Methylene-Bridged Dimer Phaeochromycin F by Streptomyces sp. OUCMDZ-4982 as a Possible Multipronged Chemical Defense Mechanism. 链霉菌 OUCMDZ-4982 非酶螯合作用将甲醛转化为抗生素亚甲基二聚体辉红霉素 F，可能是一种多管齐下的化学防御机制。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-08-07 DOI: 10.1021/acs.jnatprod.4c00702

Weihong Wang, Jiaxu Shang, Shupeng Yin, Kunyu Xia, Rui Ma, Weiming Zhu, Peng Fu

{"title":"Nonenzymatic Sequestering of Formaldehyde into the Antibiotic Methylene-Bridged Dimer Phaeochromycin F by Streptomyces sp. OUCMDZ-4982 as a Possible Multipronged Chemical Defense Mechanism.","authors":"Weihong Wang, Jiaxu Shang, Shupeng Yin, Kunyu Xia, Rui Ma, Weiming Zhu, Peng Fu","doi":"10.1021/acs.jnatprod.4c00702","DOIUrl":"10.1021/acs.jnatprod.4c00702","url":null,"abstract":"Metabolites with high chemical reactivity serve important roles in chemical defenses of organisms. Formaldehyde, as a simple and highly reactive small molecule, can be produced by microorganisms, plants, and animals. Its toxicity is well known, but information about its other biological functions remains scarce. Here, we report that the natural product SEK34b produced by Streptomyces species can react nonenzymatically with formaldehyde in water to yield the methylene-bridged dimer phaeochromycin F. This process can eliminate the toxic substance formaldehyde produced by Staphylococcus aureus. Furthermore, there is a substantial inhibitory impact of phaeochromycin F on S. aureus. We hypothesize that these constitute an integrated system of defense and attack of Streptomyces species against competitors. Our study indicates that formaldehyde can react with vancomycin and tigecycline under mild conditions to generate the derivatives bearing an imidazolidin-4-one moiety, thereby reducing the antibacterial activity of these antibiotics. These data provide a possible chemical interaction mechanism of bacteria involving the nonenzymatic reactions of formaldehyde with highly reactive natural products.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2580-2591"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141896016","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

MACE, an Open Access Database of Electron Impact Mass Spectra of Natural Products. MACE，天然产品电子碰撞质谱开放存取数据库。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 DOI: 10.1021/acs.jnatprod.4c01240

Stefan Schulz, Anton Möllerke

引用次数: 0

The Molecules Gateway: A Homogeneous, Searchable Database of 150k Annotated Molecules from Actinomycetes. 分子网关：一个包含 15 万个放线菌注释分子的同质可搜索数据库。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-25 DOI: 10.1021/acs.jnatprod.4c00857

Matteo Simone, Marianna Iorio, Paolo Monciardini, Massimo Santini, Niccolò Cantù, Arianna Tocchetti, Stefania Serina, Cristina Brunati, Thomas Vernay, Andrea Gentile, Mattia Aracne, Marco Cozzi, Justin J J van der Hooft, Margherita Sosio, Stefano Donadio, Sonia I Maffioli

{"title":"The Molecules Gateway: A Homogeneous, Searchable Database of 150k Annotated Molecules from Actinomycetes.","authors":"Matteo Simone, Marianna Iorio, Paolo Monciardini, Massimo Santini, Niccolò Cantù, Arianna Tocchetti, Stefania Serina, Cristina Brunati, Thomas Vernay, Andrea Gentile, Mattia Aracne, Marco Cozzi, Justin J J van der Hooft, Margherita Sosio, Stefano Donadio, Sonia I Maffioli","doi":"10.1021/acs.jnatprod.4c00857","DOIUrl":"10.1021/acs.jnatprod.4c00857","url":null,"abstract":"Natural products are a sustainable resource for drug discovery, but their identification in complex mixtures remains a daunting task. We present an automated pipeline that compares, harmonizes and ranks the annotations of LC-HRMS data by different tools. When applied to 7,400 extracts derived from 6,566 strains belonging to 86 actinomycete genera, it yielded 150,000 molecules after processing over 50 million MS features. The web-based Molecules Gateway provides a highly interactive access to experimental and calculated data for these molecules, along with the metadata related to extracts and producer strains. We show how the Molecules Gateway can be used to rapidly identify known hard to find microbial products, unreported analogs of known families and not yet described metabolites. The Molecules Gateway, which complements available repositories, contains annotated MS data, both acquired and computationally processed under an identical workflow, making it suitable for global analyses which reveal a large and untapped chemical diversity afforded by actinomycetes.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2615-2628"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491143","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision. 通过黄芪重新审视环黄芪醇：结构见解和构型修正。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-26 DOI: 10.1021/acs.jnatprod.4c00751

Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina

{"title":"Revisiting the Cyclocephagenols via Astragalus condensatus: Structural Insights and Configurational Revision.","authors":"Fadime Aydoğan, Pankaj Pandey, Frank R Fronczek, Daneel Ferreira, Ikhlas A Khan, Zulfiqar Ali, Amar G Chittiboyina","doi":"10.1021/acs.jnatprod.4c00751","DOIUrl":"10.1021/acs.jnatprod.4c00751","url":null,"abstract":"The phytochemical investigation of the MeOH extract of Astragalus condensatus roots led to the discovery of a new tetrahydropyran cycloartane-type triterpenoid, astracondensatol A (1), alongside six known cyclocephagenol derivatives (2, 3, 20, 32, 35, and 36). Elucidation of their structures involved 1D and 2D-NMR spectroscopy and mass data analysis. Upon comparing NMR spectroscopic data with prior literature, several carbon shift anomalies, particularly at C-24, prompted a reevaluation using quantum chemical calculations, resulting in the revision of the 24S to 24R absolute configuration for compound 2 and 38 other reported cyclocephagenol-type triterpenoids. X-ray crystallography data further supported the analysis in establishing the absolute configuration of compound 2. Ambiguous NOE correlations and publication bias could have played a significant role in miss-assigning the C-24 absolute configuration in tetrahydropyran cycloartane-type triterpenoids.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2657-2664"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491142","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Structurally Diverse Duclauxins from a Coral-Derived Talaromyces sp. and Insight into Determining the Configuration at C-1 of Heptacyclic Duclauxins by ¹H NMR. 来自珊瑚衍生的塔拉酵母菌的结构多样的杜鹃花素，以及通过 1H NMR 确定七环杜鹃花素 C-1 构型的启示。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-04 DOI: 10.1021/acs.jnatprod.4c00709

Hanxiao Zeng, Yaxing Wang, Chenyang Wang, Yahui Huang, Shuang Lin, Jiangchun Wei, Weiguang Sun, Fei Cao, Yonghui Zhang, Zhengxi Hu

{"title":"Structurally Diverse Duclauxins from a Coral-Derived Talaromyces sp. and Insight into Determining the Configuration at C-1 of Heptacyclic Duclauxins by 1H NMR.","authors":"Hanxiao Zeng, Yaxing Wang, Chenyang Wang, Yahui Huang, Shuang Lin, Jiangchun Wei, Weiguang Sun, Fei Cao, Yonghui Zhang, Zhengxi Hu","doi":"10.1021/acs.jnatprod.4c00709","DOIUrl":"10.1021/acs.jnatprod.4c00709","url":null,"abstract":"A chemical investigation of the coral-derived fungus Talaromyces sp. TJ403-AL05 led to the isolation of 18 duclauxin analogues (1-18), 14 of which, taladuxins A-N (1-14), are new and consist of the first example of duclauxin fused with one 1,6-dioxaspiro[4.5]decan-2-one moiety (1), as well as its biosynthetic product (2), and 12 6/6/6/5/6/6/6 heptacyclic derivatives (3-14). Comprehensive spectroscopic analyses, electronic circular dichroism (ECD) calculations, DP4+ probability analyses, single-crystal X-ray diffraction, and vibrational circular dichroism (VCD) calculations were employed to characterize their structures and revise the published structure of verruculosin B. An efficient 1H NMR method was established to discriminate 1R and 1S configurations at C-1 of 6/6/6/5/6/6/6 heptacyclic duclauxins according to chemical shift differences of diastereotopic methylene H2-11 or H2-12 (ΔδH-11 or ΔδH-12). Compounds 4, 7-8, 13-15, and 18 exhibited moderate inhibition of Arabidopsis thaliana 4-hydroxyphenylpyruvate dioxygenase (AtHPPD), with IC50 values ranging from 17.1 to 71.3 μM.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2592-2603"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142574985","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

MACE, an Open Access Database of Electron Impact Mass Spectra of Natural Products MACE，天然产品电子碰撞质谱开放存取数据库

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 DOI: 10.1021/acs.jnatprod.4c0124010.1021/acs.jnatprod.4c01240

Stefan Schulz, and , Anton Möllerke,

引用次数: 0

Pattern-Based Genome Mining Guides Discovery of the Antibiotic Indanopyrrole A from a Marine Streptomycete. 基于模式的基因组挖掘指导从海洋链霉菌中发现抗生素茚并吡咯 A。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 DOI: 10.1021/acs.jnatprod.4c00934

Douglas Sweeney, Alexander Bogdanov, Alexander B Chase, Gabriel Castro-Falcón, Alma Trinidad-Javier, Samira Dahesh, Victor Nizet, Paul R Jensen

{"title":"Pattern-Based Genome Mining Guides Discovery of the Antibiotic Indanopyrrole A from a Marine Streptomycete.","authors":"Douglas Sweeney, Alexander Bogdanov, Alexander B Chase, Gabriel Castro-Falcón, Alma Trinidad-Javier, Samira Dahesh, Victor Nizet, Paul R Jensen","doi":"10.1021/acs.jnatprod.4c00934","DOIUrl":"10.1021/acs.jnatprod.4c00934","url":null,"abstract":"Terrestrial actinomycetes in the genus Streptomyces have long been recognized as prolific producers of small-molecule natural products, including many clinically important antibiotics and cytotoxic agents. Although Streptomyces can also be isolated from marine environments, their potential for natural product biosynthesis remains underexplored. The MAR4 clade of largely marine-derived Streptomyces has been a rich source of novel halogenated natural products of diverse structural classes. To further explore the biosynthetic potential of this group, we applied pattern-based genome mining, leading to the discovery of the first halogenated pyrroloketoindane natural products, indanopyrrole A (1) and B (2), and the bioinformatic linkage of these compounds to an orphan biosynthetic gene cluster (BCG) in 20 MAR4 genomes. Indanopyrrole A displays potent broad-spectrum antibiotic activity against clinically relevant pathogens. A comparison of the putative indanopyrrole BGC with that of the related compound indanomycin provides new insights into the terminal cyclization and offloading mechanisms in pyrroloketoindane biosynthesis. Broader searches of public databases reveal the rarity of this BGC while also highlighting opportunities for discovering additional compounds in this uncommon class.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142685431","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp. Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-12 DOI: 10.1021/acs.jnatprod.4c01068

Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A Salim, Zeinab G Khalil, Robert J Capon

{"title":"Pullenvalenes E-H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.","authors":"Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A Salim, Zeinab G Khalil, Robert J Capon","doi":"10.1021/acs.jnatprod.4c01068","DOIUrl":"10.1021/acs.jnatprod.4c01068","url":null,"abstract":"Chemical profiling of soil-derived microbes collected under the auspices of the Australian citizen science initiative Soils for Science detected two fungi, Clonostachys sp. S4S-07771A07 and Coccidiodes sp. S4S-14879B01, capable of producing pullenvalenes, a rare class of triterpene glycoside. Cultivation profiling followed by scaled up cultivation and fractionation of the former yielded the known pullenvalenes A-D (1-4) and the new analogues E-H (5-8), with structures secured by detailed spectroscopic analysis and biogenetic considerations. This study reveals that the pullenvalenes 1-8 are produced by several genera of fungi (Clonostachys, Coccidiodes and Talaromyces) recovered from different geographic locations and substrates. We also draw attention to structural and biosynthetic similarities with the known Red Sea sponge metabolites neviotines A-D (9-12) and abudinols A-B (13-14), prompting speculation that the latter may be products of sponge-associated fungi.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2649-2656"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612710","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis. 来自铜绿微囊藻 NIES-4285 蓝藻的双同源含酪氨酸肽及其生物合成。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-10-30 DOI: 10.1021/acs.jnatprod.4c00972

Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino

{"title":"Doubly Homologated Tyrosine-Containing Peptides from the Cyanobacterium Microcystis aeruginosa NIES-4285 and Their Biosynthesis.","authors":"Chin-Soon Phan, Zhengyi Ling, Jakia Jerin Mehjabin, Kenichi Matsuda, Nurcahyo Iman Prakoso, Taiki Umezawa, Toshiyuki Wakimoto, Tatsufumi Okino","doi":"10.1021/acs.jnatprod.4c00972","DOIUrl":"10.1021/acs.jnatprod.4c00972","url":null,"abstract":"Chemical investigation of the cyanobacterium Microcystis aeruginosa NIES-4285 led to the isolation of six new natural products, microginins 705 (1), 719 (2), 733A (3), 733B (4), and 733C (5), and anabaenopeptin 885 (7), and three known compounds, anabaenopeptins 871 (6), B (8), and F (9). Planar structures and absolute configurations for 1-7 were determined by 2D NMR, HRMS, and Marfey's analyses. Microginin 733C (5), and anabaenopeptins 871 (6) and 885 (7) contained a unique residue of 2-amino-5-(4-hydroxyphenyl)pentanoic acid (Ahppa): doubly homologated tyrosine (di-hTyr). The biosynthetic origin of this nonproteinogenic amino acid di-hTyr was investigated, and it was found that MaHphABCDE are involved in the production of di-hTyr. In addition, biochemical characterization of aminotransferase MaHphE showed that it is a promiscuous enzyme. This result expanded the biocatalytic toolbox for amino acid homologation.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2629-2639"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142542874","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0