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Expression of Concern for "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091". 表达对 "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091 "的关注。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-22 Epub Date: 2024-11-13 DOI: 10.1021/acs.jnatprod.4c01237
Philip J Proteau
{"title":"Expression of Concern for \"Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived <i>Streptomyces virginiae</i> CMB-CA091\".","authors":"Philip J Proteau","doi":"10.1021/acs.jnatprod.4c01237","DOIUrl":"10.1021/acs.jnatprod.4c01237","url":null,"abstract":"","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2677"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612708","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
New Discorhabdin D Analogues from Latrunculia spp. Sponges. 从 Latrunculia spp.海绵中提取的新 Discorhabdin D 类似物。
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.4c01036
Maria Orfanoudaki, Masoumeh Dalilian, Lin Du, Cindy H Chau, William D Figg, Barry R O'Keefe, Tanja Grkovic
{"title":"New Discorhabdin D Analogues from <i>Latrunculia</i> spp. Sponges.","authors":"Maria Orfanoudaki, Masoumeh Dalilian, Lin Du, Cindy H Chau, William D Figg, Barry R O'Keefe, Tanja Grkovic","doi":"10.1021/acs.jnatprod.4c01036","DOIUrl":"10.1021/acs.jnatprod.4c01036","url":null,"abstract":"<p><p>Chemical profiles of <i>Latrunculia kaakaariki</i> and <i>Latrunculia brevis</i> were investigated, resulting in the isolation of five new discorhabdin D derivatives <b>1</b> and <b>3</b>-<b>6</b>. Their planar structures were solved by combination of NMR and HR-MS, while <i>J</i>-based configurational analysis, computational techniques, and semisynthetic methods were used for the establishment of their absolute configurations. New natural products were tested for their growth inhibitory activity against the NCI-60 human tumor cell line panel, and two compounds <b>5</b> and <b>6</b> showed low micromolar potency.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2640-2648"},"PeriodicalIF":3.3,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142491141","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
Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family. 扩大蓝藻二烷基间苯二酚巴托苷家族的多样性。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-20 DOI: 10.1021/acs.jnatprod.4c00832
João P A Reis, Sara Freitas, Tereza Procházková, Pedro N Leão
{"title":"Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family.","authors":"João P A Reis, Sara Freitas, Tereza Procházková, Pedro N Leão","doi":"10.1021/acs.jnatprod.4c00832","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00832","url":null,"abstract":"<p><p>The cyanobacterial dialkylresorcinol bartolosides were initially reported to feature glycosylated and halogenated moieties. Later, biosynthetic and <i>in vitro</i> studies showed that the chlorinated alkyl chains are utilized for a nucleophilic substitution with free fatty acid carboxylates from primary metabolism, generating bartoloside esters. Here, we applied a workflow based on PCR screening coupled to LC-HRESIMS and molecular network analysis with the aim of discovering additional bartoloside diversity. We report the annotation of 27 bartoloside and bartoloside ester derivatives, including the characterization of two new bartolosides, underlining the breadth of structures generated by bartoloside biosynthetic pathways. Some of the herein reported bartolosides feature hydroxylation in their side chains, a modification that has not been associated with this metabolite family.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142680035","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
Discovery of Sporachelins by Genome Mining of a Micromonospora Strain. 通过小孢子菌株基因组挖掘发现孢子囊蛋白
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-19 DOI: 10.1021/acs.jnatprod.4c00860
Xiaomeng Hao, Gang Wu, Hu Li, Xin Xiang, Jixiang Xu, Yuyu Liu, Zhongke Jiang, Shaowei Liu, Adeela Fatima, Maira Saleem, Feina Li, Zonggen Peng, Chenghang Sun
{"title":"Discovery of Sporachelins by Genome Mining of a <i>Micromonospora</i> Strain.","authors":"Xiaomeng Hao, Gang Wu, Hu Li, Xin Xiang, Jixiang Xu, Yuyu Liu, Zhongke Jiang, Shaowei Liu, Adeela Fatima, Maira Saleem, Feina Li, Zonggen Peng, Chenghang Sun","doi":"10.1021/acs.jnatprod.4c00860","DOIUrl":"10.1021/acs.jnatprod.4c00860","url":null,"abstract":"<p><p>Myxochelins are a group of catecholate siderophores encoded by <i>mxc</i> biosynthetic gene clusters (BGCs). They are mainly produced by myxobacteria and display a wide variety of bioactivities. Herein, we report a group of new myxochelins produced not by a myxobacterial strain but by an actinobacteria strain, <i>Micromonospora</i> sp. TMD166. They consisted of six new compounds, designated as sporachelins A (<b>1</b>), A1 (<b>2</b>), B (<b>3</b>), C (<b>4</b>), D (<b>5</b>), and E (<b>6</b>), and the known compound myxochelin A (<b>7</b>). The planar structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data, and the absolute configurations were confirmed by Marfey's analysis and chemical synthesis. The six sporachelins are the first examples of acylated derivatives at the primary alcohol of myxochelin A. These molecules were found to inhibit human 5-lipoxygenase. In addition, <b>1</b>-<b>7</b> exhibited antifibrotic activity in the TGFβ1-induced human hepatic cell line LX-2 by suppressing fibrosis-related genes <i>COL1A1</i>, <i>ACTA2</i>, and <i>TGFB1</i> expression. This is the first report of antifibrotic activity by myxochelins.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142666247","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
In Vitro Biological Target Screening and Colloidal Aggregation of Minor Cannabinoids. 小型大麻素的体外生物靶标筛选和胶体聚集。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-19 DOI: 10.1021/acs.jnatprod.4c00608
Michael F Santillo, Isabella S Glenn, Lu Paris, Robert L Sprando
{"title":"<i>In Vitro</i> Biological Target Screening and Colloidal Aggregation of Minor Cannabinoids.","authors":"Michael F Santillo, Isabella S Glenn, Lu Paris, Robert L Sprando","doi":"10.1021/acs.jnatprod.4c00608","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00608","url":null,"abstract":"<p><p>There is limited information on interactions between cannabinoids and many pharmacologically and toxicologically relevant targets in humans (e.g., receptors, ion channels, enzymes, and transporters). To address this data gap, seven cannabinoids were screened against a panel of 44 safety-related biological targets in competitive ligand binding or enzymatic activity assays. Diverse binding profiles were observed among the cannabinoids; however, colloidal aggregates were detected by dynamic light scattering and a detergent-sensitive enzyme inhibition assay. These aggregates may nonspecifically inhibit targets, yielding false positives. Although screening identified aggregates, additional testing is required to confirm cannabinoid aggregation in individual <i>in vitro</i> assays.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142674468","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
Tyrosinase Inhibitory Properties of Compounds Isolated from Artocarpus integer Roots. 从整叶蒿根中分离出的化合物对酪氨酸酶的抑制特性
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-18 DOI: 10.1021/acs.jnatprod.4c00957
Ittipon Siridechakorn, Dina Nur Shinta, Ardiansah Ardiansah, Paratchata Batsomboon, Nattaya Ngamrojanavanich, Siwattra Choodej, Khanitha Pudhom
{"title":"Tyrosinase Inhibitory Properties of Compounds Isolated from <i>Artocarpus integer</i> Roots.","authors":"Ittipon Siridechakorn, Dina Nur Shinta, Ardiansah Ardiansah, Paratchata Batsomboon, Nattaya Ngamrojanavanich, Siwattra Choodej, Khanitha Pudhom","doi":"10.1021/acs.jnatprod.4c00957","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00957","url":null,"abstract":"<p><p>A comprehensive phytochemical investigation of <i>Artocarpus integer</i> root extract led to the isolation of two new geranylated xanthones (<b>1</b> and <b>2</b>), one new geranylated flavone (<b>3</b>), one new flavanone (<b>4</b>), and one unique benzopyran (<b>5</b>), along with 16 known compounds. Structures of the new compounds were elucidated by a combination of spectroscopic and computational methods. Two different types of compounds, flavone <b>12</b> and arylbenzofuran <b>19</b>, displayed the most potent antityrosinase activity with IC<sub>50</sub> values of 1.7 ± 0.2 and 1.2 ± 0.1 μM, respectively. In addition, kinetic measurements and molecular docking simulations of compounds <b>12</b> and <b>19</b> were performed and revealed that compound <b>12</b> is a competitive inhibitor binding with the tyrosinase active site, while compound <b>19</b> is a noncompetitive tyrosinase inhibitor binding the enzyme at the allosteric site.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142646396","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
Discovery, Biosynthesis, Total Synthesis, and Biological Activities of Solanapyrones: [4 + 2] Cycloaddition-Derived Polyketides of Fungal Origin. Solanapyrones 的发现、生物合成、全合成和生物活性：源于真菌的 [4 + 2] 环加成多酮化合物。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-15 DOI: 10.1021/acs.jnatprod.4c00818
Roberto G S Berlinck, Elizabeth Skellam
{"title":"Discovery, Biosynthesis, Total Synthesis, and Biological Activities of Solanapyrones: [4 + 2] Cycloaddition-Derived Polyketides of Fungal Origin.","authors":"Roberto G S Berlinck, Elizabeth Skellam","doi":"10.1021/acs.jnatprod.4c00818","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00818","url":null,"abstract":"<p><p>Solanapyrones are metabolites bearing a 3,4-dehydrodecalin moiety isolated from cultures of different fungi that are associated with plant diseases. Research on solanapyrones resulted in the first report of a Diels-Alderase enzyme implicated in natural product biosynthesis related to the formation of the 3,4-dehydrodecalin core. In addition, several total syntheses of solanapyrones have been reported, which are also connected with the formation of the characteristic cycloaddition-derived 3,4-dehydrodecalin moiety. This Review provides the first comprehensive overview on the chemistry, biosynthesis, and biological activities of solanapyrones under the theme of synthetic and biosynthetic research progress on cycloaddition-derived secondary metabolites.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142638035","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
Discovery of Chalcone Derivatives as Bifunctional Molecules with Anti-SARS-CoV-2 and Anti-inflammatory Activities. 发现具有抗 SARS-CoV-2 和抗炎活性的双功能分子查尔酮衍生物
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-14 DOI: 10.1021/acs.jnatprod.4c00657
Xuwen Chen, Hongtao Li, Meiting Wang, Donghui Sun, Jiani Lu, Tong Zhu, Hongzhuan Chen, Lili Chen, Shunying Liu
{"title":"Discovery of Chalcone Derivatives as Bifunctional Molecules with Anti-SARS-CoV-2 and Anti-inflammatory Activities.","authors":"Xuwen Chen, Hongtao Li, Meiting Wang, Donghui Sun, Jiani Lu, Tong Zhu, Hongzhuan Chen, Lili Chen, Shunying Liu","doi":"10.1021/acs.jnatprod.4c00657","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00657","url":null,"abstract":"<p><p>Danshensu extracted with traditional Chinese medicine <i>Salvia miltiorrhiza</i> has a wide range of bioactivities. Danshensu containing a catechol moiety has a moderate inhibitory effect on SARS-CoV-2 3CL<sup>pro</sup> (IC<sub>50</sub> = 2.2 μM) by a reversible covalent interaction and exhibits good anti-inflammatory activity. To enhance the inhibitory activity, we introduced Michael receptors into the side chain of danshensu as a possible covalent warhead and blocked the covalent binding sites of catechol moiety to yield chalcone derivatives. The resulting chalcone derivatives, <b>A4</b> and <b>A7</b>, were found to inhibit SARS-CoV-2 3CL<sup>pro</sup> <i>in vitro</i> with IC<sub>50</sub> values of 83.2 and 261.3 nM, respectively. Furthermore, <b>A4</b> and <b>A7</b> inhibit viral replication in the SARS-CoV-2 replicon system with EC<sub>50</sub> values of 19.9 and 11.7 μM, respectively. Time-dependent inhibition experiment and mass spectrometry show that <b>A4</b> acted as a noncovalent mixed inhibitor, while <b>A7</b> likely binds covalently at Cys145. The interaction mechanism between SARS-CoV-2 3CL<sup>pro</sup> and <b>A4</b> or <b>A7</b> was characterized by molecular docking studies. Additionally, both <b>A4</b> and <b>A7</b> demonstrated potent anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. These promising results suggest that chalcone derivatives <b>A4</b> and <b>A7</b> can serve as bifunctional molecules with both antivirus and anti-inflammatory properties.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2024-11-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142612705","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
Expression of Concern for “Tepuazines A–E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091” 对 "Tepuazines A-E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomycese virginiae CMB-CA091" 表示关注
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-11-13 DOI: 10.1021/acs.jnatprod.4c0123710.1021/acs.jnatprod.4c01237
Philip J. Proteau*, 
{"title":"Expression of Concern for “Tepuazines A–E: Phenazine Glycosides from a Venezuelan Quartz-Rich (Tepui) Cave Soil-Derived Streptomyces virginiae CMB-CA091”","authors":"Philip J. Proteau*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0123710.1021/acs.jnatprod.4c01237","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01237https://doi.org/10.1021/acs.jnatprod.4c01237","url":null,"abstract":"","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 11","pages":"2677 2677"},"PeriodicalIF":3.3,"publicationDate":"2024-11-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142691416","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 : 2024-11-12 DOI: 10.1021/acs.jnatprod.4c0106810.1021/acs.jnatprod.4c01068
Yanan Wang, Jolynn Kiong, Amila Agampodi Dewa, Angela A. Salim, Zeinab G. Khalil and Robert J. Capon*, 
{"title":"Pullenvalenes E–H: Triterpenyl-Aminoglycosides from an Australian Soil-Derived Fungus, Clonostachys sp.","authors":"Yanan Wang,&nbsp;Jolynn Kiong,&nbsp;Amila Agampodi Dewa,&nbsp;Angela A. Salim,&nbsp;Zeinab G. Khalil and Robert J. Capon*,&nbsp;","doi":"10.1021/acs.jnatprod.4c0106810.1021/acs.jnatprod.4c01068","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01068https://doi.org/10.1021/acs.jnatprod.4c01068","url":null,"abstract":"<p >Chemical profiling of soil-derived microbes collected under the auspices of the Australian citizen science initiative Soils for Science detected two fungi, <i>Clonostachys</i> sp. S4S-07771A07 and <i>Coccidiodes</i> 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 (<b>1</b>–<b>4</b>) and the new analogues E–H (<b>5</b>–<b>8</b>), with structures secured by detailed spectroscopic analysis and biogenetic considerations. This study reveals that the pullenvalenes <b>1</b>–<b>8</b> are produced by several genera of fungi (<i>Clonostachys</i>, <i>Coccidiodes</i> and <i>Talaromyces</i>) 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 (<b>9</b>–<b>12</b>) and abudinols A–B (<b>13</b>–<b>14</b>), prompting speculation that the latter may be products of sponge-associated fungi.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"87 11","pages":"2649–2656 2649–2656"},"PeriodicalIF":3.3,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142685206","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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