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Biochemical and Structural Insights of the N-Methyltransferase CyaF in Cyanogramide Biosynthesis
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-07 DOI: 10.1021/acs.jnatprod.4c0139110.1021/acs.jnatprod.4c01391
Ruijie Chen, Qingbo Zhang, Liping Zhang, Chunyan Fang, Hanning Zhu, Weiming Zhu*, Changsheng Zhang and Yiguang Zhu*, 
{"title":"Biochemical and Structural Insights of the N-Methyltransferase CyaF in Cyanogramide Biosynthesis","authors":"Ruijie Chen,&nbsp;Qingbo Zhang,&nbsp;Liping Zhang,&nbsp;Chunyan Fang,&nbsp;Hanning Zhu,&nbsp;Weiming Zhu*,&nbsp;Changsheng Zhang and Yiguang Zhu*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0139110.1021/acs.jnatprod.4c01391","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01391https://doi.org/10.1021/acs.jnatprod.4c01391","url":null,"abstract":"<p ><i>N</i>-Methyltransferases involved in indole methylation have seldom been discovered in natural product biosynthesis. This study focuses on the enzyme CyaF, which catalyzes a critical <i>N</i>-methylation step of indole in the β-carboline skeleton during cyanogramide biosynthesis. Seven β-carboline analogues (<b>3</b>–<b>9</b>) were isolated from the recombinant strain <i>Streptomyces coelicolor</i> YF11/<i>cyaABC</i>, including three new compounds (<b>5</b>–<b>7</b>). <i>In vitro</i> assays revealed CyaF’s substrate flexibility. The crystal structure of the CyaF/<i>S</i>-adenosyl-<span>L</span>-homocysteine (SAH) complex, combined with the AlphaFold-predicted model and site-directed mutagenesis, elucidated the catalytic mechanism and structural features that enable CyaF to accommodate diverse substrates, highlighting its potential for biocatalytic applications.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"715–722 715–722"},"PeriodicalIF":3.3,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713866","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
Palladium-Catalyzed Late-Stage Functionalization of Natural Antitumor Drug: Synthesis and Bioactivity of 5-Aryl Camptothecins
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-07 DOI: 10.1021/acs.jnatprod.4c0134410.1021/acs.jnatprod.4c01344
Lian Sun, Xiao-Long Li, Qiu-Shan Huang, Wan-Sheng Ji, Xiaohuan Li, Jin-Bu Xu* and Feng Gao*, 
{"title":"Palladium-Catalyzed Late-Stage Functionalization of Natural Antitumor Drug: Synthesis and Bioactivity of 5-Aryl Camptothecins","authors":"Lian Sun,&nbsp;Xiao-Long Li,&nbsp;Qiu-Shan Huang,&nbsp;Wan-Sheng Ji,&nbsp;Xiaohuan Li,&nbsp;Jin-Bu Xu* and Feng Gao*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0134410.1021/acs.jnatprod.4c01344","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01344https://doi.org/10.1021/acs.jnatprod.4c01344","url":null,"abstract":"<p >Camptothecin (CPT) and its derivatives have garnered significant interest due to their potent anticancer activity. In this study, 62 novel CPT derivatives (<b>1a</b>–<b>31a</b> and <b>1b</b>–<b>31b</b>) were designed and synthesized through Pd-catalyzed late-stage modification at the C-5 position. The anticancer efficacy of these compounds against three human cancer cell lines was evaluated. Compounds 5<i>R</i>-<b>12a</b> (IC<sub>50</sub> = 0.05 ± 0.01 μM against HCT-116) and 5<i>R</i>-<b>6a</b> (IC<sub>50</sub> = 0.04 ± 0.03 μM against MCF-7) exhibited enhanced antitumor activity when compared to CPT. The preliminary mechanism of apoptosis was investigated through cell viability assays, protein expression, and docking analysis. The results indicated that compounds <b>12a</b> and <b>6a</b> exhibited a greater ability to induce apoptosis and G2/M phase arrest than did CPT. Docking results provided a possible explanation for the superior activity of the 5<i>R</i> configuration. This work would offer new insights for CPT lead compound development.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"706–714 706–714"},"PeriodicalIF":3.3,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713865","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
Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-04 DOI: 10.1021/acs.jnatprod.4c0124710.1021/acs.jnatprod.4c01247
Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N. Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N. Ninh, Djaja D. Soejarto, Joanna E. Burdette, James R. Fuchs, A. Douglas Kinghorn and Harinantenaina L. Rakotondraibe*, 
{"title":"Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam","authors":"Ermias Mekuria Addo,&nbsp;Daniel Adu-Ampratwum,&nbsp;Elizabeth N. Kaweesa,&nbsp;Garima Agarwal,&nbsp;Dmitriy Uchenik,&nbsp;Tran N. Ninh,&nbsp;Djaja D. Soejarto,&nbsp;Joanna E. Burdette,&nbsp;James R. Fuchs,&nbsp;A. Douglas Kinghorn and Harinantenaina L. Rakotondraibe*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0124710.1021/acs.jnatprod.4c01247","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01247https://doi.org/10.1021/acs.jnatprod.4c01247","url":null,"abstract":"<p >The tropical plant <i>Aglaia perviridis</i> is known to produce cyclopenta[<i>b</i>]benzofuran and other types of rocaglate derivatives including silvestrol (<b>3</b>) and 5‴-episilvestrol (<b>4</b>) that are of current pharmacological interest. In the present work, further investigation of <i>A. perviridis</i> roots collected in Vietnam has yielded two new rocaglate acetonide derivatives (<b>1</b> and <b>2</b>) and a known pentanor-3,4-<i>seco</i>-dammarane triterpenoid (<b>7</b>) found for the first time as a natural product, in addition to four known rocaglates (<b>3</b>–<b>6</b>). The structures of compounds <b>1</b> and <b>2</b> were confirmed by partial synthesis experiments, and their potential occurrence as extraction artifacts was investigated by targeted selective ion monitoring using UHPLC-MS. All compounds obtained were evaluated against a panel of four human cancer cell lines, in which the six rocaglate derivatives (<b>1</b>–<b>6</b>) tested all showed submicromolar potencies.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"662–670 662–670"},"PeriodicalIF":3.3,"publicationDate":"2025-03-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714144","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
Seven New Guanidine Derivatives and One New Hypoxanthine Derivative Isolated from the Scorpion Buthus martensii and Potential Anti-Neuroinflammatory Activity
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-03 DOI: 10.1021/acs.jnatprod.5c0004010.1021/acs.jnatprod.5c00040
Ke-Ming Li, Wei-Fen Li, Yong-Ming Yan, Guangyi Yang and Yong-Xian Cheng*, 
{"title":"Seven New Guanidine Derivatives and One New Hypoxanthine Derivative Isolated from the Scorpion Buthus martensii and Potential Anti-Neuroinflammatory Activity","authors":"Ke-Ming Li,&nbsp;Wei-Fen Li,&nbsp;Yong-Ming Yan,&nbsp;Guangyi Yang and Yong-Xian Cheng*,&nbsp;","doi":"10.1021/acs.jnatprod.5c0004010.1021/acs.jnatprod.5c00040","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00040https://doi.org/10.1021/acs.jnatprod.5c00040","url":null,"abstract":"<p >Twelve guanidine derivatives (<b>1</b>–<b>12</b>), including seven new compounds (martensiiagms A–G, <b>1</b>–<b>7</b>), one new hypoxanthine derivative (martensiiagm H, <b>13</b>), and 15 known compounds (<b>14</b>–<b>28</b>) were isolated from the whole body of <i>Buthus martensii</i> Karsch and identified by analysis of data. Subsequent biological evaluations revealed the anti-inflammatory activity of compound <b>1</b>. It attenuates the neuroinflammation and oxidative stress levels prompted by lipopolysaccharide. This attenuation is accomplished by a specific action on mitochondria, which, in turn, caused a significant decrease in reactive oxygen species and pro-inflammatory cytokines.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"821–829 821–829"},"PeriodicalIF":3.3,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714020","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
LC-MS Guided Discovery and Biosynthetic Pathway of Coprisamides E–H, Cinnamic Acid-Containing Metabolites from the Marine Algae-Derived Streptomyces thermolineatus NAK03196
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-03 DOI: 10.1021/acs.jnatprod.4c0143910.1021/acs.jnatprod.4c01439
Guo Dong Zhang, Zhi Wei Yang, Fang Zhou Yin, Zhang Yuan Yan, Zi Jun Xiong, Shuai Ma, Zhi Kai Guo* and Rui Hua Jiao*, 
{"title":"LC-MS Guided Discovery and Biosynthetic Pathway of Coprisamides E–H, Cinnamic Acid-Containing Metabolites from the Marine Algae-Derived Streptomyces thermolineatus NAK03196","authors":"Guo Dong Zhang,&nbsp;Zhi Wei Yang,&nbsp;Fang Zhou Yin,&nbsp;Zhang Yuan Yan,&nbsp;Zi Jun Xiong,&nbsp;Shuai Ma,&nbsp;Zhi Kai Guo* and Rui Hua Jiao*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0143910.1021/acs.jnatprod.4c01439","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01439https://doi.org/10.1021/acs.jnatprod.4c01439","url":null,"abstract":"<p >Four cinnamoyl-containing nonribosomal peptides (CCNPs), coprisamides E<b>–</b>H (<b>1</b>–<b>4</b>), were isolated from the marine algae-associated actinomycete strain <i>Streptomyces thermolineatus</i> NAK03196. Their structures were elucidated to be unreported coprisamides by comprehensive analyses of HRESIMS, 1D and 2D NMR spectroscopic data, Marfey’s method, and MS/MS analysis. Coprisamides E (<b>1</b>) and F (<b>2</b>) bear a characteristic nonproteinogenic amino acid, 2,3-diaminopropanoic acid. The biosynthetic pathways for these isolates were proposed through a comparison of their biosynthetic gene clusters with reported homologous gene clusters. Coprisamide E (<b>1</b>) exhibited weak antibacterial activity against the Gram-positive strain <i>Staphylococcus aureus</i>.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"862–870 862–870"},"PeriodicalIF":3.3,"publicationDate":"2025-03-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714012","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
Stereoanalysis of the Antiparasitic Natural Product Callunene and Its Synthetic Intermediates
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-03-02 DOI: 10.1021/acs.jnatprod.4c0142410.1021/acs.jnatprod.4c01424
Jiří Ferenczei, Vilém Blahout, Hana Dvořáková, Andrea Brancale, Petra Cuřínová*, Magdaléna Labíková, Michal Kohout, Vladimír Setnička and Pavla Perlíková*, 
{"title":"Stereoanalysis of the Antiparasitic Natural Product Callunene and Its Synthetic Intermediates","authors":"Jiří Ferenczei,&nbsp;Vilém Blahout,&nbsp;Hana Dvořáková,&nbsp;Andrea Brancale,&nbsp;Petra Cuřínová*,&nbsp;Magdaléna Labíková,&nbsp;Michal Kohout,&nbsp;Vladimír Setnička and Pavla Perlíková*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0142410.1021/acs.jnatprod.4c01424","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01424https://doi.org/10.1021/acs.jnatprod.4c01424","url":null,"abstract":"<p >The recent popularity of indoor farming has brought about problems with parasites spreading among pollinator colonies. The natural product callunene (<b>1</b>) can be used in the prophylaxis of bumblebees against <i>Crithidia</i> infection. Here, we report the synthesis of callunene (<b>1</b>), its enantioseparation, and a method for analyzing its optical purity. The approach was applied to determine the configuration of callunene extracted from heather honey. The proposed method is also applicable to the analysis of mixtures of diastereomers obtained during callunene synthesis, which allows the stereospecificity of individual reaction steps to be determined.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 3","pages":"723–731 723–731"},"PeriodicalIF":3.3,"publicationDate":"2025-03-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.jnatprod.4c01424","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143713951","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Correction to "Phenalenones and Polyesters from Talaromyces stipitatus and Structure Revision of Talaromycesone A".
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-01-29 DOI: 10.1021/acs.jnatprod.5c00035
Nirmal K Chaudhary, Daniel Vuong, Ernest Lacey, Andrew M Piggott, Peter Karuso
{"title":"Correction to \"Phenalenones and Polyesters from <i>Talaromyces stipitatus</i> and Structure Revision of Talaromycesone A\".","authors":"Nirmal K Chaudhary, Daniel Vuong, Ernest Lacey, Andrew M Piggott, Peter Karuso","doi":"10.1021/acs.jnatprod.5c00035","DOIUrl":"10.1021/acs.jnatprod.5c00035","url":null,"abstract":"","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"616"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057445","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
Identification of Isoliensinine as a Ferroptosis Suppressor with Iron-Chelating Activity. 鉴定具有铁螯合活性的异叶绿素抑制剂
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2024-08-19 DOI: 10.1021/acs.jnatprod.4c00471
Yijing Song, Min Li, You Li, Tianyi Zhang, Jiawei Zhang, Dan Han, Fuzhi Lian, Xuqing Liu, Xuexian Fang
{"title":"Identification of Isoliensinine as a Ferroptosis Suppressor with Iron-Chelating Activity.","authors":"Yijing Song, Min Li, You Li, Tianyi Zhang, Jiawei Zhang, Dan Han, Fuzhi Lian, Xuqing Liu, Xuexian Fang","doi":"10.1021/acs.jnatprod.4c00471","DOIUrl":"10.1021/acs.jnatprod.4c00471","url":null,"abstract":"<p><p>Ferroptosis is a type of regulated cell death driven by the iron-dependent accumulation of lipid peroxides. The high involvement of ferroptosis in diverse human diseases highlights the need for the identification of new chemotypes with anti-ferroptotic activity. Here, we performed a natural product library screening in HT1080 fibrosarcoma cells and identified licochalcone A (LA), isoeugenyl acetate (ISA), and isoliensinine (ISL) as suppressors of either RSL3- or IKE-induced ferroptosis. Mechanistically, ferroptosis resistance conferred by these compounds is mainly through GPX4/NRF2-independent mechanisms. Among them, only ISL could effectively rescue ferroptosis induced by FINO<sub>2</sub>, which is a stable oxidant of ferrous iron, suggesting that ISL may have the properties of an iron chelator. Consistent with the hypothesis, both computational tools and X-ray photoelectron spectroscopy supported the binding between ISL and iron ions. And ISL greatly inhibited excessive iron-dependent ferroptotic cell death through limiting intracellular iron accumulation. Furthermore, its iron chelator activity also protected mice from organ injury in an acute iron overload model. In conclusion, this study provided valuable insights for developing effective anti-ferroptosis agents from natural products, which represent a potential therapeutic strategy for treating ferroptosis-associated organ damage.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"245-254"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142002988","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 : 2025-02-28 Epub 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":"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":"502-512"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","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
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 : 2025-02-28 Epub 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":"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":"530-536"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","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
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