Journal of Natural Products 最新文献

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Antimycobacterial Activities of the Zanthoxylum leprieurii Metabolite Adubangoamide and Non-Natural Fagaramide Analogues.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-11 DOI: 10.1021/acs.jnatprod.4c01377
Benson Oloya, Jane Namukobe, Mandy Krüger, Willy Ssengooba, Eric Sperlich, George Kwesiga, Kevin Komakech, Matthias Heydenreich, Robert Byamukama, Bernd Schmidt
{"title":"Antimycobacterial Activities of the <i>Zanthoxylum leprieurii</i> Metabolite Adubangoamide and Non-Natural Fagaramide Analogues.","authors":"Benson Oloya, Jane Namukobe, Mandy Krüger, Willy Ssengooba, Eric Sperlich, George Kwesiga, Kevin Komakech, Matthias Heydenreich, Robert Byamukama, Bernd Schmidt","doi":"10.1021/acs.jnatprod.4c01377","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01377","url":null,"abstract":"<p><p><i>trans</i>-Fagaramide (<b>1</b>) and adubangoamide (<b>2</b>) are natural products with a cinnamic acid amide skeleton that have recently been isolated from <i>Zanthoxylum leprieurii</i>, a medicinal plant used locally in Uganda for the treatment of tuberculosis. Insufficient quantities of material from the natural source originally prevented the antimycobacterial evaluation of the new natural product <b>2</b>. Herein, a synthesis of <b>2</b> is reported, and its antimycobacterial activity was determined using the synthetic material. Adubangoamide (<b>2</b>) is three times more active against the drug-susceptible <i>M. tuberculosis</i> strain H<sub>37</sub>Rv than <i>trans</i>-fagaramide (<b>1</b>), with an MIC value of 10.0 μM. In addition, we synthesized eight non-natural analogues of <i>trans</i>-fagaramide (<b>1</b>, MIC = 32.0 μM against H<sub>37</sub>Rv strain), in which benzylamide groups mimic the isobutylamide part of the <i>trans</i>-fagaramide structure. Five out of eight synthetic analogues are more active than the parent natural product: <b>11b</b> (MIC = 6.0 μM), <b>11d</b> (21.0 μM), <b>11e</b> (6.1 μM), <b>11g</b> (17.0 μM), and <b>11h</b> (4.5 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389511","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
Anti-Inflammatory Dimeric and Trimeric Flavonoids from the Roots ofPistacia weinmannifolia.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-11 DOI: 10.1021/acs.jnatprod.4c01009
Seong Mi Lee, Hyung Won Ryu, Hyoung-Geun Kim, Yang Hee Jo, Kyoung Jin Park, Su Ui Lee, Eun Sol Oh, Sang Woo Lee, Sangho Choi, Wan-Yi Li, Bang Yeon Hwang, Sei-Ryang Oh
{"title":"Anti-Inflammatory Dimeric and Trimeric Flavonoids from the Roots of<i>Pistacia weinmannifolia</i>.","authors":"Seong Mi Lee, Hyung Won Ryu, Hyoung-Geun Kim, Yang Hee Jo, Kyoung Jin Park, Su Ui Lee, Eun Sol Oh, Sang Woo Lee, Sangho Choi, Wan-Yi Li, Bang Yeon Hwang, Sei-Ryang Oh","doi":"10.1021/acs.jnatprod.4c01009","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01009","url":null,"abstract":"<p><p>As part of an ongoing search for new anti-inflammatory agents from medicinal plants, five new dimeric and trimeric flavonoids (<b>1</b>-<b>5</b>) were isolated from the roots of <i>Pistacia weinmannifolia</i>. The structures of pistachalcone A (<b>1</b>), pistachalcone B (<b>2</b>), pistaflavanone A (<b>3</b>), pistachalcone C (<b>4</b>), and pistachalcone D (<b>5</b>) were elucidated by the analysis of spectroscopic data. The known compounds rhuschalcone II (<b>6</b>), rhuschalcone VI (<b>7</b>), and pauferrol B (<b>8</b>) were also isolated and identified. Our <i>in vitro</i> analysis found that compounds isolated from <i>P. weinmannifolia</i> root extract exert anti-inflammatory effects in phorbol myristate acetate (PMA)-induced NCI-H292 airway epithelial cells by the suppression of expression levels such as interleukin-8 (IL-8) and mucin 5AC (MUC5AC), which are closely related to the pulmonary inflammatory response in the pathogenesis of COPD. Therefore, these dihydrochalcone derivatives may have value as new starting materials for the development of drug candidates against COPD.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389510","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
Ion Mobility-Coupled Mass Spectrometry for Metallophore Detection.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-10 DOI: 10.1021/acs.jnatprod.4c00911
Bailey A Bell, Josephine M Anderson, Scott R Rajski, Tim S Bugni
{"title":"Ion Mobility-Coupled Mass Spectrometry for Metallophore Detection.","authors":"Bailey A Bell, Josephine M Anderson, Scott R Rajski, Tim S Bugni","doi":"10.1021/acs.jnatprod.4c00911","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00911","url":null,"abstract":"<p><p>Metal chelating small molecules (metallophores) play significant roles in microbial interactions and bacterial survival; however, current methods to identify metallophores are limited by low sensitivity, a lack of metal selectivity, and/or complicated data analysis. To overcome these limitations, we developed a novel approach for detecting metallophores in natural product extracts using ion mobility-coupled mass spectrometry (IM-MS). As a proof of concept, marine bacterial extracts containing known metallophores were analyzed by IM-MS with and without added metals, and the data were compared between conditions to identify metal-binding metabolites. Ions with changes in both mass and mobility were specific to metallophores, enabling their identification within these complex extracts. Additionally, we compared the use of direct infusion (DI) and liquid chromatography (LC) separation with IM-MS. For most samples, DI outperformed LC by minimizing the time required for data collection and simplifying analysis. However, for some samples, LC improved the detection of metallophores likely by reducing ion suppression. IM-MS was then used to identify 10 metallophores in an extract from a marine <i>Micromonospora</i> sp. Overall, incorporating IM-MS facilitated the rapid detection of metal-binding natural products in complex bacterial extracts through the comparison of mass and mobility data in the presence and absence of metals.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143389512","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
An Enantioselective Approach for the Structure Revision of Isolophanthin E and Syntheses of Proposed Structures of Isolophanthins A, B, and C.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-07 DOI: 10.1021/acs.jnatprod.4c01327
Sravya Surendran, Chandrendu K C, Goreti Rajendar
{"title":"An Enantioselective Approach for the Structure Revision of Isolophanthin E and Syntheses of Proposed Structures of Isolophanthins A, B, and C.","authors":"Sravya Surendran, Chandrendu K C, Goreti Rajendar","doi":"10.1021/acs.jnatprod.4c01327","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01327","url":null,"abstract":"<p><p>The first enantioselective total synthesis and structure revision of isolophanthin E and syntheses of proposed structures of isolophanthins A, B, and C are demonstrated. Natural product 3β-hydroxy-8,11,13,15-abietatetraene was directly synthesized utilizing an efficient cationic polyene cyclization, and it is used as a common intermediate in the synthesis of isolophanthins and related abietatriene natural products. Two distinct synthetic routes were established for the synthesis of different stereoisomers of isolophanthin E. Spectroscopic analysis and structural assignment of isolophanthin E stereoisomers provide valuable insights into the relative configuration of the C-2, C-3-dihydroxy A ring of similar terpenoids, aiding in the identification of their configuration. A total of seven diterpenoids were obtained using regioselective chloromethylation, Sharpless dihydroxylation, Cu(II) catalyzed allyl-benzyl coupling, epoxide-initiated polyene cyclization, Rubottom oxidation, and additive-controlled dihydroxylation as key synthetic steps.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143363167","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
SpectroIBIS: Automated Data Processing for Multiconformer Quantum Chemical Spectroscopic Calculations.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-07 DOI: 10.1021/acs.jnatprod.4c01321
Brodie W Bulcock, Yit-Heng Chooi, Gavin R Flematti
{"title":"SpectroIBIS: Automated Data Processing for Multiconformer Quantum Chemical Spectroscopic Calculations.","authors":"Brodie W Bulcock, Yit-Heng Chooi, Gavin R Flematti","doi":"10.1021/acs.jnatprod.4c01321","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01321","url":null,"abstract":"<p><p>Quantum chemical spectroscopic calculations have grown increasingly popular in natural products research for aiding the elucidation of chemical structures, especially their stereochemical configurations. These calculations have become faster with modern computational speeds, but subsequent data handling, inspection, and presentation remain key bottlenecks for many researchers. In this article, we introduce the SpectroIBIS computer program as a user-friendly tool to automate tedious tasks commonly encountered in this workflow. Through a simple graphical user interface, researchers can drag and drop Gaussian or ORCA output files to produce Boltzmann-averaged ECD, VCD, UV-vis and IR data, optical rotations, and/or <sup>1</sup>H and <sup>13</sup>C NMR chemical shifts in seconds. Also produced are formatted, publication-quality supplementary data tables containing conformer energies and atomic coordinates, saved to a DOCX file compatible with Microsoft Word and LibreOffice. Importantly, SpectroIBIS can assist researchers in finding common calculation issues by automatically checking for redundant conformers and imaginary frequencies. Additional useful features include recognition of conformer energy recalculations at a higher theory level, and automated generation of input files for quantum chemistry programs with optional exclusion of high-energy conformers. Lastly, we demonstrate the applicability of SpectroIBIS with spectroscopic calculations for five natural products. SpectroIBIS is open-source software available as a free desktop application (https://github.com/bbulcock/SpectroIBIS).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143363172","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
Machine Learning-Based Bioactivity Classification of Natural Products Using LC-MS/MS Metabolomics.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-07 DOI: 10.1021/acs.jnatprod.4c01123
Nathaniel J Brittin, Josephine M Anderson, Doug R Braun, Scott R Rajski, Cameron R Currie, Tim S Bugni
{"title":"Machine Learning-Based Bioactivity Classification of Natural Products Using LC-MS/MS Metabolomics.","authors":"Nathaniel J Brittin, Josephine M Anderson, Doug R Braun, Scott R Rajski, Cameron R Currie, Tim S Bugni","doi":"10.1021/acs.jnatprod.4c01123","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01123","url":null,"abstract":"<p><p>The rediscovery of known drug classes represents a major challenge in natural products drug discovery. Compound rediscovery inhibits the ability of researchers to explore novel natural products and wastes significant amounts of time and resources. This study introduces a novel machine learning framework that can effectively characterize the bioactivity of natural products by leveraging liquid chromatography tandem mass spectrometry and untargeted metabolomics analysis. This accelerates natural product drug discovery by addressing the challenge of dereplicating previously discovered bioactive compounds. Utilizing the SIRIUS 5 metabolomics software suite and <i>in-silico</i>-generated fragmentation spectra, we have trained a ML model capable of predicting a compound's drug class. This approach enables the rapid identification of bioactive scaffolds from LC-MS/MS data, even without reference experimental spectra. The model was trained on a diverse set of molecular fingerprints generated by SIRIUS 5 to effectively classify compounds based on their core pharmacophores. Our model robustly classified 21 diverse bioactive drug classes, achieving accuracies greater than 93% on experimental spectra. This study underscores the potential of ML combined with MFPs to dereplicate bioactive natural products based on pharmacophore, streamlining the discovery process and expediting improved methods of isolating novel antibacterial and antifungal agents.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143370111","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
A Model for STEM Education: The Role of Natural Products at Drew University.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-07 DOI: 10.1021/acs.jnatprod.5c00117
Vincent P Gullo
{"title":"A Model for STEM Education: The Role of Natural Products at Drew University.","authors":"Vincent P Gullo","doi":"10.1021/acs.jnatprod.5c00117","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00117","url":null,"abstract":"<p><p>At Drew University, the Research Institute for Scientists Emeriti (RISE) provides a unique research experience for students. RISE Fellows are successful industry research scientists who mentor undergraduate students on research projects. The students get the opportunity to work closely in the laboratory on projects of interest to both the student and the RISE Fellow. The projects are challenging, and the students have a first-hand experience in addressing \"real world\" research problems. Natural product research is central to the careers of many of the RISE Fellows and many of the projects in the program. For students, the variety of disciplines required in natural product research serves as outstanding scientific training. The success of the program is measured by the excellent student outcomes from the RISE program. For the RISE Fellows the reward is continuing to pursue their passion for discovery and helping to create the next generation of scientists. The RISE program can serve as an excellent STEM training model for other universities.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143363163","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
Purified Monascus Pigments: Biological Activities and Mechanisms of Action.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-05 DOI: 10.1021/acs.jnatprod.4c01008
Marketa Husakova, Petra Patakova
{"title":"Purified <i>Monascus</i> Pigments: Biological Activities and Mechanisms of Action.","authors":"Marketa Husakova, Petra Patakova","doi":"10.1021/acs.jnatprod.4c01008","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01008","url":null,"abstract":"<p><p><i>Monascus</i> pigments having yellow, orange, and red colors are widely studied for their potential beneficial properties. Many different biological activities have been reported regarding <i>Monascus</i> pigments and their derivatives, but the usual method is to test complex extracts from the mycelium of the fungus or from a fungus-fermented substrate. However, this review is mainly concerned with the biological activities of purified <i>Monascus</i> pigments. Both yellow (ankaflavin, monascin) and red (rubropunctamine, monascorubramine) <i>Monascus</i> pigments are proven antioxidants if used in concentrations of 10 μg/mL or higher. Antimicrobial activity against Gram-positive and Gram-negative bacteria and fungi has been observed with all <i>Monascus</i> pigments. However, the best antimicrobials are red <i>Monascus</i> pigments, and their amino acid derivatives (l-cysteine derivatives have MIC 4 μg/mL against <i>Enterococcus faecalis</i>). Yellow monaphilones and orange monaphilols seem to have the highest anti-inflammatory activity (IC<sub>50</sub> 1.7 μM of monaphilol D) and, together with red <i>Monascus</i> pigment derivatives, have mild antiobesity and antidiabetic activities. Further, monascin and ankaflavin in daily doses of 0.5 and 0.08 mg, respectively, lowered serum blood levels of low-density lipoprotein cholesterol complexes in rats on a high-fat diet. Orange <i>Monascus</i> pigments, rubropunctatin and monaphilols A and C, exhibit cytotoxic and antitumor activities (IC<sub>50</sub> 8-10 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143187728","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
Jejupeptins A and B: Polyketide-Cyclic Peptide Hybrids with Anti-Corticosterone Activity from Streptomyces sp. KCB15JA151.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-04 DOI: 10.1021/acs.jnatprod.4c01201
Jun-Pil Jang, Jongtae Roh, Gil Soo Kim, Jihun Park, Gwi Ja Hwang, Beomcheol Park, Hyeok-Won Lee, Shunji Takahashi, Young-Soo Hong, Sung-Kyun Ko, Jae-Hyuk Jang
{"title":"Jejupeptins A and B: Polyketide-Cyclic Peptide Hybrids with Anti-Corticosterone Activity from <i>Streptomyces</i> sp. KCB15JA151.","authors":"Jun-Pil Jang, Jongtae Roh, Gil Soo Kim, Jihun Park, Gwi Ja Hwang, Beomcheol Park, Hyeok-Won Lee, Shunji Takahashi, Young-Soo Hong, Sung-Kyun Ko, Jae-Hyuk Jang","doi":"10.1021/acs.jnatprod.4c01201","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01201","url":null,"abstract":"<p><p>Two new polyketide-cyclic peptide hybrids jejupeptins A <b>(1)</b> and B (<b>2</b>), together with a known compound eurystatin B (<b>3</b>), were isolated from a culture of <i>Streptomyces</i> sp. KCB15JA151. The chemical structures of the compounds were elucidated using a combination of 1D and 2D NMR spectroscopy and DP4+ probability analyses. Comprehensive spectroscopic analysis revealed that <b>1</b> and <b>2</b> are the first examples of hybrid peptide-polyketides possessing an unprecedented 4-amino-3-hydroxymethyl-3-methyl-2-oxopentanoic acid moiety. A plausible biosynthetic pathway for these compounds was proposed. Biological evaluation demonstrated that compounds <b>1</b> and <b>2</b> exhibit protective effects against corticosterone-induced apoptosis and cellular oxidative stress without any associated cytotoxicity.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143187725","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
Otitiglycomycins A and B: Glycolipids from the Strain Nocardia otitidiscavarum 20S-13 with Antiviral Activity against Zika Virus.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-03 DOI: 10.1021/acs.jnatprod.4c01302
Phuong-Y Mai, Élodie Marguerite, Jamal Ouazzani, Philippe Lopes, Pascal Retailleau, Jean-François Gallard, Xavier Moppert, Bernard Costa, Géraldine Le Goff, Chaker El Kalamouni, Erwan Poupon, Mehdi A Beniddir
{"title":"Otitiglycomycins A and B: Glycolipids from the Strain <i>Nocardia otitidiscavarum</i> 20S-13 with Antiviral Activity against Zika Virus.","authors":"Phuong-Y Mai, Élodie Marguerite, Jamal Ouazzani, Philippe Lopes, Pascal Retailleau, Jean-François Gallard, Xavier Moppert, Bernard Costa, Géraldine Le Goff, Chaker El Kalamouni, Erwan Poupon, Mehdi A Beniddir","doi":"10.1021/acs.jnatprod.4c01302","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01302","url":null,"abstract":"<p><p>The Zika virus (ZIKV), an emerging orthoflavivirus, presents a significant public health threat due to its rapid dissemination and association with severe neurological complications. The urgent need for effective antiviral agents has driven research into novel bioactive compounds derived from unique natural sources. Microorganisms inhabiting extreme environments are particularly promising for such discoveries due to their potential to produce unique metabolites. In this study, we explored microorganisms from the underexplored French Polynesian microbial mats known as \"Kopara\" to identify new bioactive natural products. Using a molecular networking-based dereplication strategy, we investigated various culture and extraction techniques of the strain <i>Nocardia otitidiscaviarum</i> 20-S13, leading to the discovery of two novel glycoglycerolipids, otitiglycomycins A and B (<b>1</b> and <b>2</b>). Structure elucidation of these compounds was achieved through NMR spectroscopy, X-ray crystallography, and TDDFT-specific rotation prediction. We found that otitiglycomycin A (<b>1</b>), but not otitiglycomycin B (<b>2</b>), suppresses ZIKV infection at non cytotoxic concentrations without effects on cell viability. Time-of-drug addition assays along with virus inactivation and binding assays demonstrated that <b>1</b> neutralizes ZIKV infectivity by preventing the virus from attaching to the host cell membrane.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-02-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143121828","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
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