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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 : 2024-12-27 Epub 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":"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":"2892-2906"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11686517/pdf/","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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Direct Identification of α-Bisabolol Enantiomers in an Essential Oil Using a Combined Ion Mobility-Mass Spectrometry/Quantum Chemistry Approach. 利用离子迁移率-质谱法/量子化学组合方法直接鉴定精油中的α-双香叶醇对映体
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2020-03-26 DOI: 10.1021/acs.jnatprod.9b00982
Erik Laurini, Stéphane Andreani, Alain Muselli, Sabrina Pricl, Aura Tintaru
{"title":"Direct Identification of α-Bisabolol Enantiomers in an Essential Oil Using a Combined Ion Mobility-Mass Spectrometry/Quantum Chemistry Approach.","authors":"Erik Laurini, Stéphane Andreani, Alain Muselli, Sabrina Pricl, Aura Tintaru","doi":"10.1021/acs.jnatprod.9b00982","DOIUrl":"10.1021/acs.jnatprod.9b00982","url":null,"abstract":"<p><p>Enantiomer-specific identification of chiral molecules in natural extracts is a challenging task, as many routine analytical techniques fail to provide selectivity in multicomponent mixtures. Here we describe an alternative approach, based on the combination of ion mobility-mass spectrometry (IM-MS) and quantum chemistry (QM), for the direct enantiomers differentiation in crude essential oils. The identification of α-bisabolol enantiomers contained in the raw essential oil (EO) from the Corsican <i>Xanthium italicum</i> fruits is reported as a proof-of-concept. Accordingly, IM-MS experiments performed in Ag<sup>+</sup>-doped methanol revealed the presence of both (+)- and (-)-α-bisabolol in the EO, while molecular simulations provided the structures of the two α-bisabolol enantiomer silver(I) adducts.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2887-2891"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"37771084","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
Phenalenones and Polyesters from Talaromyces stipitatus and Structure Revision of Talaromycesone A. 塔芳酮A的苯二烯酮和聚酯及其结构修正。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-16 DOI: 10.1021/acs.jnatprod.4c00885
Nirmal K Chaudhary, Daniel Vuong, Ernest Lacey, Andrew M Piggott, Peter Karuso
{"title":"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.4c00885","DOIUrl":"10.1021/acs.jnatprod.4c00885","url":null,"abstract":"<p><p>Investigation of the secondary metabolites of the filamentous fungus <i>Talaromyces stipitatus</i> led to the isolation of two new phenalenone dimers, talarohemiketal A (<b>1</b>) and talaroazasone A (<b>2</b>), and one new macrolide polyester, talaromacrolactone A (<b>3</b>), along with the reported oxyphenalenone dimers talaromycesone A (<b>4</b>), bacillisporin A (<b>5</b>), bacillisporin B (<b>6</b>), bacillisporin C (<b>7</b>), <i>epi</i>-bacillisporin F (<b>8</b>), and bacillisporin J (<b>9</b>), the phenalenone monomer funalenone (<b>10</b>), the polyesters 15G256α (<b>11</b>) and 15G256ν (<b>12</b>), and 6-hydroxymellein (<b>13</b>). Detailed analysis of 2D NMR correlations, supported by TDDFT calculations, led to the structural revision of talaromycesone A as <b>4</b> from previously reported structure <b>14</b>. In addition, the previously misassigned NMR spectra of compound <b>8</b> have been corrected.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2738-2745"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833106","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 : 2024-12-27 Epub 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":"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":"2709-2715"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11686503/pdf/","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":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Is Linalyl Anthranilate Indeed Found In Plant Samples? GC-MS Misidentifications in the Scientific Literature. 在植物样本中确实发现了芳樟苯甲酸酯吗？科学文献中的气相色谱-质谱鉴别错误。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-16 DOI: 10.1021/acs.jnatprod.4c01118
Katarzyna Pokajewicz, Tomasz Biernat, Piotr P Wieczorek
{"title":"Is Linalyl Anthranilate Indeed Found In Plant Samples? GC-MS Misidentifications in the Scientific Literature.","authors":"Katarzyna Pokajewicz, Tomasz Biernat, Piotr P Wieczorek","doi":"10.1021/acs.jnatprod.4c01118","DOIUrl":"10.1021/acs.jnatprod.4c01118","url":null,"abstract":"<p><p>Linalyl anthranilate (LNA) has been identified in a number of plant extracts and essential oils by various authors using gas chromatography-mass spectrometry (GC-MS). However, the reported retention behavior of LNA in these studies is inconsistent with the retention data provided in the NIST database. Therefore, the objective of this study was to determine whether the reports of LNA were the result of misidentifications in GC-MS analyses or if the linear NIST retention index was inaccurate. To accomplish this, linalyl anthranilate was synthesized in a two-step procedure, and the resulting product was authenticated using nuclear magnetic resonance (NMR) and GC-MS analyses. This is a new synthetic route to linalyl anthranilate. Subsequently, retention indices for linalyl anthranilate were determined on three commonly used GC phases: polydimethylsiloxane, 5% diphenyl-95% polydimethylsiloxane, and polyethylene glycol. The study confirmed the accuracy of the NIST retention data, establishing the linear retention index data for LNA on a semi-nonpolar GC column as 2051. However, LNA reported in the literature by various authors exhibited a retention index in the elution window of approximately 1000-1400, strongly suggesting that these reports were the result of GC-MS misidentifications. A review of all reported occurrences of LNA in natural samples found no credible evidence of its presence. In many cases, it appears to be a misidentification of linalyl acetate caused by the occurrence of an erroneous spectrum in the older versions of the NIST mass spectra database.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2839-2846"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142833104","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
Cyclopeptide Avellanins D-O with Antimalarial Activity from the Mariana Trench Anemone-Derived Hamigera ingelheimensis MSC5. 从马里亚纳海沟天葵提取的 Hamigera ingelheimensis MSC5 中提取的具有抗疟活性的环肽 Avellanins D-O。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-27 DOI: 10.1021/acs.jnatprod.4c00740
Hao Li, Yuling Chen, Bingqing Tang, Zhengjie Liu, Bo Peng, Jiajun Li, Han Gao, Sibao Wang, Zhiyong Li
{"title":"Cyclopeptide Avellanins D-O with Antimalarial Activity from the Mariana Trench Anemone-Derived <i>Hamigera ingelheimensis</i> MSC5.","authors":"Hao Li, Yuling Chen, Bingqing Tang, Zhengjie Liu, Bo Peng, Jiajun Li, Han Gao, Sibao Wang, Zhiyong Li","doi":"10.1021/acs.jnatprod.4c00740","DOIUrl":"10.1021/acs.jnatprod.4c00740","url":null,"abstract":"<p><p>Marine microorganisms are a treasure trove of natural products, especially those in extreme marine environments, which may produce novel natural products. Herein, biosynthetic gene cluster analysis combined with an integrated metabolomic strategy incorporating matrix-assisted laser desorption ionization-time-of-flight mass spectrometry (MALDI-TOF MS), nuclear magnetic resonance (NMR), and liquid chromatography-mass spectrometry/mass spectrometry (LC-MS/MS) based Global Natural Products Social Molecular Networking (GNPS) was used to discover new compounds from the Mariana trench anemone-derived fungus <i>Hamigera ingelheimensis</i> MSC5. As a result, 12 new cyclic pentapeptides, avellanins D-O (<b>1</b>-<b>12</b>), were isolated, together with a known cyclic pentapeptide avellanin C (<b>13</b>). All the structures and absolute configurations were elucidated using NMR, mass spectrometry, X-ray diffraction analysis, and Marfey's method. A plausible biosynthetic pathway for the avellanins was proposed based on the gene cluster analysis of <i>H. ingelheimensis</i> MSC5. Bioassay revealed that compound <b>6</b> exhibited potent antimalarial activity with an IC<sub>50</sub> value of 0.19 ± 0.09 μM.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2695-2708"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724536","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
Abietane Diterpenoids from the Rhizomes of Kaempferia roscoeana and Their Anti-Inflammatory Activities. 山奈根茎中的阿比坦二萜及其抗炎活性
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-27 DOI: 10.1021/acs.jnatprod.4c01127
Ratchanaporn Chokchaisiri, Apinya Kaisoda, Sarot Cheenpracha, Lucksagoon Ganranoo, Sareeya Bureekaew, Chutamas Thepmalee, Apichart Suksamrarn
{"title":"Abietane Diterpenoids from the Rhizomes of <i>Kaempferia roscoeana</i> and Their Anti-Inflammatory Activities.","authors":"Ratchanaporn Chokchaisiri, Apinya Kaisoda, Sarot Cheenpracha, Lucksagoon Ganranoo, Sareeya Bureekaew, Chutamas Thepmalee, Apichart Suksamrarn","doi":"10.1021/acs.jnatprod.4c01127","DOIUrl":"10.1021/acs.jnatprod.4c01127","url":null,"abstract":"<p><p>Six new abietane diterpenes, roscoeananes A-F (<b>1</b>-<b>6</b>), along with two known compounds (<b>7</b>-<b>8</b>) were isolated from the rhizomes of <i>Kaempferia roscoeana</i>. The structures of all compounds were elucidated by analysis of spectroscopic data, and the absolute configurations were assigned by a comparison of the theoretical and experimental electronic circular dichroism (ECD) spectra and a comparison with literature values. The unreported compound <b>5</b> is an ether-linked dimer of roscoeanane B (<b>2</b>). Most of the isolated compounds were tested for their nitric oxide inhibitory effects in lipopolysaccharide-activated RAW264.7 cells. Among them, roscoeanane A (<b>1</b>) was found to reduce NO levels in murine macrophage cells with an IC<sub>50</sub> value of 3.58 ± 0.95 μM and exhibited low cytotoxicity (IC<sub>50</sub> > 50 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2847-2854"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142737784","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 Cyclic Lipopeptides, Octaminomycins C and D, by Engineering LysR Transcriptional Regulator of Streptomyces sp. 链霉菌LysR转录调控因子在环脂肽octaminomycin C和D中的应用
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-12-13 DOI: 10.1021/acs.jnatprod.4c01047
Joon Soo An, Jung Min Kim, Jaeho Han, Jun Young Lee, Sang-Jip Nam, Sang Kook Lee, Yeo Joon Yoon, Dong-Chan Oh
{"title":"Discovery of Cyclic Lipopeptides, Octaminomycins C and D, by Engineering LysR Transcriptional Regulator of <i>Streptomyces</i> sp.","authors":"Joon Soo An, Jung Min Kim, Jaeho Han, Jun Young Lee, Sang-Jip Nam, Sang Kook Lee, Yeo Joon Yoon, Dong-Chan Oh","doi":"10.1021/acs.jnatprod.4c01047","DOIUrl":"10.1021/acs.jnatprod.4c01047","url":null,"abstract":"<p><p>New lipodepsipeptides, octaminomycins C and D (<b>1</b> and <b>2</b>), were discovered in an engineered <i>Streptomyces</i> sp. strain overexpressing the LysR transcriptional regulator family. The structures of <b>1</b> and <b>2</b> were elucidated by comprehensive analysis of their UV, HRMS, and NMR data. The absolute configurations were determined using spectroscopic analysis, the advanced Marfey's method, and genomic analysis. Genomic analysis enabled the identification of the nonribosomal peptide synthetase (NRPS) biosynthetic pathway of the octaminomycins.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2822-2828"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142816771","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
Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp., with Selective Activity against Dirofilaria immitis (Heartworm). Goondolinones A and B: Terpenyl-quinolin-4(1H)-ones from an Australian Volcanic Crater Soil-Derived Actinomadura sp.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-24 DOI: 10.1021/acs.jnatprod.4c01146
Jianying Han, David F Bruhn, Dana C Roberts, Erica J Burkman, Yovany Moreno, Paul V Bernhardt, Angela A Salim, Robert J Capon
{"title":"Goondolinones A and B: Terpenyl-quinolin-4(1<i>H</i>)-ones from an Australian Volcanic Crater Soil-Derived <i>Actinomadura</i> sp., with Selective Activity against <i>Dirofilaria immitis</i> (Heartworm).","authors":"Jianying Han, David F Bruhn, Dana C Roberts, Erica J Burkman, Yovany Moreno, Paul V Bernhardt, Angela A Salim, Robert J Capon","doi":"10.1021/acs.jnatprod.4c01146","DOIUrl":"10.1021/acs.jnatprod.4c01146","url":null,"abstract":"<p><p>A chemical investigation of the Australian pasture soil-derived <i>Actinomadura</i> sp. S4S-00245B09, supported by chemical, bioactivity and cultivation profiling, yielded a new class of terpenyl-quinolin-4(1<i>H</i>)-ones, goondolinones A and B (<b>1</b> and <b>2</b>), featuring an unprecedented fused seven-membered ether. Structures were assigned to <b>1</b> and <b>2</b> on the basis of detailed spectroscopic analysis, including X-ray analysis of <b>1</b>, and biosynthetic considerations. Goondolinone A (<b>1</b>) lacks antibacterial or antifungal properties, is noncytotoxic to two human carcinoma cell lines, but exhibits selective inhibition of the motility of heartworm <i>Dirofilaria immitis</i> microfilaria (EC<sub>50</sub> 5.1 μM) and L4 larvae (EC<sub>50</sub> 21.4 μM). As a new anthelmintic scaffold, future understanding of the structure activity relationship and mechanism of action of <b>1</b> could inform the discovery of new treatments for heartworm and other filarial diseases, capable of safeguarding the health and welfare of companion animals.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2855-2862"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142708598","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
Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis. Goondomycins A-H: Carbocyclic ansa-Polyketides from an Australian Pasture Streptomyces with Selective Activity against Dirofilaria immitis.
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-12-27 Epub Date: 2024-11-26 DOI: 10.1021/acs.jnatprod.4c00987
Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon
{"title":"Goondomycins A-H: Carbocyclic <i>ansa</i>-Polyketides from an Australian Pasture <i>Streptomyces</i> with Selective Activity against <i>Dirofilaria immitis</i>.","authors":"Jianying Han, David F Bruhn, Dana C Roberts, Erica Burkman, Yovany Moreno, Angela A Salim, Robert J Capon","doi":"10.1021/acs.jnatprod.4c00987","DOIUrl":"10.1021/acs.jnatprod.4c00987","url":null,"abstract":"<p><p>A bioassay-guided chemical investigation of an Australian pasture-soil-derived <i>Streptomyces</i> sp. yielded the rare carbocyclic <i>ansa</i>-polyketide kendomycin (<b>1</b>) along with a series of new analogues, goondomycins A-H (<b>2</b>-<b>9</b>), featuring unprecedented carbo/heterocyclic scaffolds and chromophores, with structures assigned by detailed spectroscopic analysis, chemical and biochemical transformations, and biosynthetic considerations. Goondomycins B (<b>2</b>) and F (<b>7</b>) are noteworthy in being potent motility inhibitors of heartworm <i>Dirofilaria immitis</i> microfilaria (EC<sub>50</sub> 0.3 and 0.5 μM) and L4 larvae (EC<sub>50</sub> 1.4 and 1.8 μM), while exhibiting no significant antibacterial and antifungal activity or cytotoxicity to mammalian cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"2810-2821"},"PeriodicalIF":3.3,"publicationDate":"2024-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142724537","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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