Journal of Natural Products 最新文献

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Chemoreactive 2,5-Diketopiperazines from a Penicillium sp., Structure Revision of Reported Analogues and Proposed Facile Transformation Pathways. 一种青霉菌的化学活性 2,5-二酮哌嗪、已报道类似物的结构修订以及拟议的简便转化途径。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-12 DOI: 10.1021/acs.jnatprod.4c00478
Quan T Khong, Emily A Smith, Karen L Wendt, Masoumeh Dalilian, Ekaterina I Goncharova, Isaac Brownell, Robert H Cichewicz, Curtis J Henrich, John A Beutler, Barry R O'Keefe, Lin Du
{"title":"Chemoreactive 2,5-Diketopiperazines from a <i>Penicillium</i> sp., Structure Revision of Reported Analogues and Proposed Facile Transformation Pathways.","authors":"Quan T Khong, Emily A Smith, Karen L Wendt, Masoumeh Dalilian, Ekaterina I Goncharova, Isaac Brownell, Robert H Cichewicz, Curtis J Henrich, John A Beutler, Barry R O'Keefe, Lin Du","doi":"10.1021/acs.jnatprod.4c00478","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00478","url":null,"abstract":"<p><p>Merkel cell carcinoma (MCC) is a rare and aggressive cutaneous cancer. Two new prenylated indole 2,5-diketopiperazine alkaloids, brevianamides E1 (<b>1</b>) and E2 (<b>2</b>), were isolated from a <i>Penicillium</i> fungus. Both compounds showed moderate cytotoxic activity against select MCC cell lines (i.e., MCC13, MKL-1, UISO, and WaGa) in the low micromolar range. The relative and absolute configurations of <b>1</b> and <b>2</b> were determined by combined approaches, including NOESY spectroscopy, DFT ECD and DP4 plus calculations, and Marfey's reaction. Literature research and the comparison of NMR and ECD data led to the structure revision of three previously reported natural analogues, notoamides K and P and asperversiamide L. The structurally unstable <b>1</b> and <b>2</b> underwent steady interconversion under neutral aqueous conditions. Investigation of the degradation of <b>2</b> in acidic methanol solutions led to the identification of a new methoxylated derivative (<b>6</b>) and two new ring-opened products (<b>7</b> and <b>8</b>) with the rearranged, elongated, 4-methylpent-3-ene side chain. The facile transformation of <b>2</b> to <b>7</b> and <b>8</b> was promoted by the intrinsic impurity (i.e., formaldehyde) of HPLC-grade methanol through the aza-Cope rearrangement.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141588932","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 Uncommon Tryptophan-Containing Diketopiperazines from Aspergillus homomorphus CBS 101889 Using an Aspergillus nidulans Heterologous Expression System. 利用黑曲霉异源表达系统从同型曲霉 CBS 101889 中发现不常见的含色氨酸的二酮哌嗪。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-11 DOI: 10.1021/acs.jnatprod.4c00113
Cory B Jenkinson, Shu-Yi Lin, Mary Villarreal, C Elizabeth Oakley, David H Sherman, Ching-Kuo Lee, Clay C C Wang, Berl R Oakley
{"title":"Discovery of Uncommon Tryptophan-Containing Diketopiperazines from <i>Aspergillus homomorphus</i> CBS 101889 Using an <i>Aspergillus nidulans</i> Heterologous Expression System.","authors":"Cory B Jenkinson, Shu-Yi Lin, Mary Villarreal, C Elizabeth Oakley, David H Sherman, Ching-Kuo Lee, Clay C C Wang, Berl R Oakley","doi":"10.1021/acs.jnatprod.4c00113","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00113","url":null,"abstract":"<p><p>Fungal secondary metabolite (SM) biosynthetic gene clusters (BGCs) containing dimethylallyltryptophan synthases (DMATSs) produce structurally diverse prenylated indole alkaloids with wide-ranging activities that have vast potential as human therapeutics. To discover new natural products produced by DMATSs, we mined the Department of Energy Joint Genome Institute's MycoCosm database for DMATS-containing BGCs. We found a DMATS BGC in <i>Aspergillus homomorphus</i> CBS 101889, which also contains a nonribosomal peptide synthetase (NRPS). This BGC appeared to have a previously unreported combination of genes, which suggested the cluster might make novel SMs. We refactored this BGC with highly inducible promoters into the model fungus <i>Aspergillus nidulans</i>. The expression of this refactored BGC in <i>A</i>. <i>nidulans</i> resulted in the production of eight tryptophan-containing diketopiperazines, six of which are new to science. We have named them homomorphins A-F (<b>2</b>, <b>4</b>-<b>8</b>). Perhaps even more intriguingly, to our knowledge, this is the first discovery of C4-prenylated tryptophan-containing diketopiperazines and their derivatives. In addition, the NRPS from this BGC is the first described that has the ability to promiscuously combine tryptophan with either of two different amino acids, in this case, l-valine or l-<i>allo</i>-isoleucine.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141578157","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
NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of Carpesium abrotanoides L. 核磁共振引导从胭脂虫果实中分离出抗炎性胡罗卜素内酯
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-10 DOI: 10.1021/acs.jnatprod.4c00338
Lu Fu, Can-Can Wang, Wenyue Tian, Zhiyan Liu, Meng-Yu Bao, Jiazheng Liu, Wei Zhang, Li-Ping Bai, Zhi-Hong Jiang, Guo-Yuan Zhu
{"title":"NMR-Guided Isolation of Anti-inflammatory Carabranolides from the Fruits of <i>Carpesium abrotanoides</i> L.","authors":"Lu Fu, Can-Can Wang, Wenyue Tian, Zhiyan Liu, Meng-Yu Bao, Jiazheng Liu, Wei Zhang, Li-Ping Bai, Zhi-Hong Jiang, Guo-Yuan Zhu","doi":"10.1021/acs.jnatprod.4c00338","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00338","url":null,"abstract":"<p><p>Carabranolides present characteristic NMR resonances for the cyclopropane moiety, which distinctly differ from those of other compounds and were used for an NMR-guided isolation in this study. As a result, 11 undescribed carabranolides (<b>1</b>-<b>11</b>), along with five known ones (<b>12</b>-<b>16</b>), were isolated from the fruits of <i>Carpesium abrotanoides</i> L. Compounds <b>1</b>-<b>11</b> are new esters of carabrol at C-4 with different carboxylic acids. Their structures were elucidated by HRESIMS and NMR spectroscopic data analysis. The biological evaluation showed that compounds <b>2</b>-<b>4</b>, <b>15</b>, and <b>16</b> exhibited significant inhibitory activity against LPS-induced NO release with an IC<sub>50</sub> value of 5.6-9.1 μM and dose-dependently decreased iNOS protein expression in RAW264.7 cells.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141578158","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
Characterization of Sesquiterpene Dimers from the Flowers of Inula japonica and the Structural Revisions of Related Compounds. 茵陈花中半萜二聚体的表征及相关化合物的结构修正
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-09 DOI: 10.1021/acs.jnatprod.4c00269
Zheng Niu, Chun-Yan Chen, Yan Zhou, Guan-Ke Liu, Bing-Yang Zhang, Mahmood Brobbey Oppong, De-Qin Zhang, Tie Yao, Feng Qiu
{"title":"Characterization of Sesquiterpene Dimers from the Flowers of <i>Inula japonica</i> and the Structural Revisions of Related Compounds.","authors":"Zheng Niu, Chun-Yan Chen, Yan Zhou, Guan-Ke Liu, Bing-Yang Zhang, Mahmood Brobbey Oppong, De-Qin Zhang, Tie Yao, Feng Qiu","doi":"10.1021/acs.jnatprod.4c00269","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00269","url":null,"abstract":"<p><p>Sesquiterpene dimers are mainly found in the Asteraceae family. However, conflicting reports on the structures of these compounds can be found in the literature. Herein, we describe ten sesquiterpene dimers isolated from the flowers of <i>Inula japonica</i>, including configurational revisions of japonicone H (<b>1</b>-<b>1</b>), japonicone D (<b>2</b>-<b>1</b>), inulanolide A (<b>4</b>-<b>1</b>), japonicone X (<b>5</b>-<b>1</b>), and inulanolide F (<b>5</b>-<b>2</b>) to compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>5</b>, respectively. Five new related metabolites (<b>3</b> and <b>6</b>-<b>9</b>) are also described. Application of GIAO NMR/DP4+ analyses and ECD/OR calculations enabled us to revise the absolute configurations of an additional 13 sesquiterpene dimers isolated from plants of the genus <i>Inula</i>. Compounds <b>1</b>, <b>2</b>, <b>4</b>, and <b>6</b> exhibited inhibition of nitric oxide production in lipopolysaccharide activated RAW264.7 macrophages with IC<sub>50</sub> values of 4.07-10.00 μM.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141561970","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
Genome-Driven Discovery of Antiviral Atralabdans A-C from the Soil-Dwelling Streptomyces atratus. 基因组驱动从土栖链霉菌中发现抗病毒的 Atralabdans A-C。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-08 DOI: 10.1021/acs.jnatprod.4c00225
Ling Shen, Yanyan Wang, Chengxin Liu, Wula Alateng, Yuxin Wang, Axel Zeeck, Weiguang Wang, Peng Zhang, Yanhong Wei, Xiaofeng Cai
{"title":"Genome-Driven Discovery of Antiviral Atralabdans A-C from the Soil-Dwelling <i>Streptomyces atratus</i>.","authors":"Ling Shen, Yanyan Wang, Chengxin Liu, Wula Alateng, Yuxin Wang, Axel Zeeck, Weiguang Wang, Peng Zhang, Yanhong Wei, Xiaofeng Cai","doi":"10.1021/acs.jnatprod.4c00225","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00225","url":null,"abstract":"<p><p>Heterologous expression of an <i>atr</i> terpenoid gene cluster derived from <i>Streptomyces atratus</i> Gö66 in <i>S. albus</i> J1074 led to the discovery of three novel labdane diterpenoids featuring an unprecedented 6/6/5-fused tricyclic skeleton, designated as atralabdans A-C (<b>1</b>-<b>3</b>), along with a known compound, labdanmycin A. Compounds <b>1</b>-<b>3</b> were identified through extensive spectroscopic analysis, including NMR calculations with DP4+ probability analysis, and a comparative assessment of experimental and theoretical electronic circular dichroism (ECD) spectra. A plausible biosynthetic pathway for these compounds was proposed. Compounds <b>1</b>-<b>3</b> exhibited inhibitory activity against the human neurotropic coxsackievirus B3 (CVB3); <b>1</b> was the most potent, surpassing the positive control ribavirin with a higher therapeutic index.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141557403","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
Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant Turraea delphinensis. 热带植物 Turraea delphinensis 中萜类化合物的分离、特征和抗增殖活性。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-06 DOI: 10.1021/acs.jnatprod.4c00313
Hayato Kouno, Saidanxia Amuti, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, Masuo Goto, David J Newman, Barry R O'Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto
{"title":"Isolation, Characterization, and Antiproliferative Activity of Terpenoids from the Tropical Plant <i>Turraea delphinensis</i>.","authors":"Hayato Kouno, Saidanxia Amuti, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, Masuo Goto, David J Newman, Barry R O'Keefe, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto","doi":"10.1021/acs.jnatprod.4c00313","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00313","url":null,"abstract":"<p><p>The isolation, structure determination, and biological evaluation of constituents from the organic extract of <i>Turraea delphinensis</i> Wahlert (Meliaceae) resulted in the isolation of 51 secondary metabolites, including 14 new terpenoids (six cycloartanes, four tirucallanes/euphanes, three limonoids, and a 7-keto sterol). Among the new compounds, <b>1</b> is the first triterpenoid with a trioxaspiro[4.4]nonane side chain, while <b>11</b>-<b>13</b> are the first 17-γ-lactone tetranortriterpenoids with four oxygenated functional groups at C-1, -3, -6, and -7. The isolated compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a vinblastine-resistant cell line.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141544150","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
Natural Products Have Increased Rates of Clinical Trial Success throughout the Drug Development Process. 天然产品在整个药物开发过程中的临床试验成功率更高。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-06 DOI: 10.1021/acs.jnatprod.4c00581
Daniel Domingo-Fernández, Yojana Gadiya, António José Preto, Christoph A Krettler, Sarah Mubeen, August Allen, David Healey, Viswa Colluru
{"title":"Natural Products Have Increased Rates of Clinical Trial Success throughout the Drug Development Process.","authors":"Daniel Domingo-Fernández, Yojana Gadiya, António José Preto, Christoph A Krettler, Sarah Mubeen, August Allen, David Healey, Viswa Colluru","doi":"10.1021/acs.jnatprod.4c00581","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00581","url":null,"abstract":"<p><p>Natural products (NPs) or their derivatives represent a large proportion of drugs that successfully progress through clinical trials to approval. This study explores the presence of NPs in both early- and late-stage drug discovery to determine their success rate, and the factors or features of natural products that contribute to such success. As a proxy for early drug development stages, we analyzed patent applications over several decades, finding a consistent proportion of NP, NP-derived, and synthetic-compound-based patent documents, with the latter group outnumbering NP and NP-derived ones (approximately 77% vs 23%). We next assessed clinical trial data, where we observed a steady increase in NP and NP-derived compounds from clinical trial phases I to III (from approximately 35% in phase I to 45% in phase III), with an inverse trend observed in synthetics (from approximately 65% in phase I to 55% in phase III). Finally, <i>in vitro</i> and <i>in silico</i> toxicity studies revealed that NPs and their derivatives were less toxic alternatives to their synthetic counterparts. These discoveries offer valuable insights for successful NP-based drug development, highlighting the potential benefits of prioritizing NPs and their derivatives as starting points.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141544151","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
Structure Revision of the Fungal Phytotoxin Cavoxin and of Its Corresponding Chroman-4-one Cavoxone by X-ray Crystallography. 通过 X 射线晶体学修正真菌植物毒素 Cavoxin 及其对应的 Chroman-4-one Cavoxone 的结构。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-05 DOI: 10.1021/acs.jnatprod.4c00531
Angela Tuzi, Marianna Carbone, Maria Letizia Ciavatta, Antonio Evidente
{"title":"Structure Revision of the Fungal Phytotoxin Cavoxin and of Its Corresponding Chroman-4-one Cavoxone by X-ray Crystallography.","authors":"Angela Tuzi, Marianna Carbone, Maria Letizia Ciavatta, Antonio Evidente","doi":"10.1021/acs.jnatprod.4c00531","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00531","url":null,"abstract":"<p><p>Cavoxin (<b>1</b>) was isolated as the main phytotoxin produced by <i>Phoma cava</i> Schulzer, a toxigenic fungus isolated from <i>Castanea</i> spp. Its structure was determined by 1D NMR and MS in 1985 along with that of the corresponding chroman-4-one cavoxone (<b>2</b>), an artifact formed by acid treatment of <b>1</b>. Since that time cavoxin was shown to be phytotoxic, antifungal, antifeedant, herbicidal, and antirust with potential application in agriculture and medicine. During a study aimed at improving cavoxin's production by <i>P. cava</i>, single crystals for X-ray diffractometric analysis were obtained. The X-ray crystallography characterization confirmed only in part the structure proposed for cavoxin (<b>1</b>), revealing a different substitution pattern on the aromatic ring, as depicted in the revised structure <b>3</b>.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141532818","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
Triplinones A-H: Anti-Inflammatory Arylalkenyl α,β-Unsaturated-δ-Lactones Isolated from the Leaves of Australian Rainforest Plant Cryptocarya triplinervis (Lauraceae). Triplinones A-H:从澳大利亚热带雨林植物 Cryptocarya triplinervis(月桂科)叶中分离出的抗炎芳基烯基 α、β-不饱和-δ-内酯。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-04 DOI: 10.1021/acs.jnatprod.4c00454
Paayal Kumar, Matthew Wallis, Xian Zhou, Feng Li, Darren C Holland, Paul Reddell, Gerald Münch, Ritesh Raju
{"title":"Triplinones A-H: Anti-Inflammatory Arylalkenyl α,β-Unsaturated-δ-Lactones Isolated from the Leaves of Australian Rainforest Plant <i>Cryptocarya triplinervis</i> (Lauraceae).","authors":"Paayal Kumar, Matthew Wallis, Xian Zhou, Feng Li, Darren C Holland, Paul Reddell, Gerald Münch, Ritesh Raju","doi":"10.1021/acs.jnatprod.4c00454","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00454","url":null,"abstract":"<p><p>Our ongoing exploration of Australian rainforest plants for the biodiscovery of anti-inflammatory agents led to the isolation and structural elucidation of eight new arylalkenyl α,β-unsaturated-δ-lactones, triplinones A-H (<b>1-8</b>), from the leaves of the Australian rainforest plant <i>Cryptocarya triplinervis</i> B. Hyland (Lauraceae). The chemical structures of these compounds were established by NMR spectroscopic data analysis, while their relative and absolute configurations were established using a combination of Mosher ester analysis utilizing both Riguera's and Kishi's methods, ECD experiments, and X-ray crystallography analysis. Compounds <b>1-8</b> exhibited good inhibitory activities toward nitric oxide (NO) production in lipopolysaccharide (LPS) and interferon (IFN)-γ induced RAW 264.7 macrophages, in particular compounds <b>1-3</b> and <b>5</b>, with IC<sub>50</sub> values of 7.3 ± 0.5, 6.0 ± 0.3, 5.6 ± 0.3, and 5.4 ± 2.5 μM, respectively.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141532819","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
Iron(III) Binding Properties of PF1140, a Fungal N-Hydroxypyridone, and Activity against Mycoplasma genitalium. 真菌 N-羟基吡啶酮 PF1140 的铁(III)结合特性及对生殖支原体的活性。
IF 3.3 2区 生物学
Journal of Natural Products Pub Date : 2024-07-03 DOI: 10.1021/acs.jnatprod.4c00209
Thilini Peramuna, Caroline M Kim, Laarni Kendra T Aguila, Karen L Wendt, Gwendolyn E Wood, Robert H Cichewicz
{"title":"Iron(III) Binding Properties of PF1140, a Fungal <i>N</i>-Hydroxypyridone, and Activity against <i>Mycoplasma genitalium</i>.","authors":"Thilini Peramuna, Caroline M Kim, Laarni Kendra T Aguila, Karen L Wendt, Gwendolyn E Wood, Robert H Cichewicz","doi":"10.1021/acs.jnatprod.4c00209","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00209","url":null,"abstract":"<p><p><i>Mycoplasma genitalium</i> is a sexually transmitted bacterium associated with urogenital disease syndromes in the US and worldwide. The global rise in drug resistance in <i>M. genitalium</i> necessitates the development of novel drugs to treat this pathogen. To address this need, we have screened extracts from a library of fungal isolates assembled through the University of Oklahoma Citizen Science Soil Collection Program. Analysis of one of the bioactive extracts using bioassay-guided fractionation led to the purification of the compound PF1140 (<b>1</b>) along with a new and several other known pyridones. The <i>N</i>-hydroxy pyridones are generally regarded as siderophores with high binding affinity for iron(III) under physiological conditions. Results from UV-vis absorption spectroscopy-based titration experiments revealed that <b>1</b> complexes with Fe<sup>3+</sup>. As <i>M. genitalium</i> does not utilize iron, we propose that the PF1140-iron complex induces cytotoxicity by facilitating the cellular uptake of iron, which reacts with endogenous hydrogen peroxide to produce toxic hydroxyl radicals.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-07-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141489959","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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