Journal of Natural Products 最新文献_第9页

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 : 2025-02-28 Epub 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 ofPistacia weinmannifolia.","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":"10.1021/acs.jnatprod.4c01009","url":null,"abstract":"As part of an ongoing search for new anti-inflammatory agents from medicinal plants, five new dimeric and trimeric flavonoids (1-5) were isolated from the roots of Pistacia weinmannifolia. The structures of pistachalcone A (1), pistachalcone B (2), pistaflavanone A (3), pistachalcone C (4), and pistachalcone D (5) were elucidated by the analysis of spectroscopic data. The known compounds rhuschalcone II (6), rhuschalcone VI (7), and pauferrol B (8) were also isolated and identified. Our in vitro analysis found that compounds isolated from P. weinmannifolia 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.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"314-321"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","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

Fatuamide A, a Hybrid PKS/NRPS Metallophore from a Leptolyngbya sp. Marine Cyanobacterium Collected in American Samoa.

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.4c01051

Kelsey L Alexander, C Benjamin Naman, Arihiro Iwasaki, Alfonso Mangoni, Tiago Leao, Raphael Reher, Daniel Petras, Hyunwoo Kim, Eva Ternon, Eduardo J E Caro-Diaz, Evgenia Glukhov, Jana A Mitrevska, Nicole E Avalon, Brendan M Duggan, Lena Gerwick, William H Gerwick

{"title":"Fatuamide A, a Hybrid PKS/NRPS Metallophore from a Leptolyngbya sp. Marine Cyanobacterium Collected in American Samoa.","authors":"Kelsey L Alexander, C Benjamin Naman, Arihiro Iwasaki, Alfonso Mangoni, Tiago Leao, Raphael Reher, Daniel Petras, Hyunwoo Kim, Eva Ternon, Eduardo J E Caro-Diaz, Evgenia Glukhov, Jana A Mitrevska, Nicole E Avalon, Brendan M Duggan, Lena Gerwick, William H Gerwick","doi":"10.1021/acs.jnatprod.4c01051","DOIUrl":"10.1021/acs.jnatprod.4c01051","url":null,"abstract":"A structurally novel metabolite, fatuamide A (1), was discovered from a laboratory cultured strain of the marine cyanobacterium Leptolyngbya sp., collected from Faga'itua Bay, American Samoa. A bioassay-guided approach using NCI-H460 human lung cancer cells directed the isolation of fatuamide A, which was obtained from the most cytotoxic fraction. The planar structure of fatuamide A was elucidated by integrated NMR and MS/MS analysis, and a combination of bioinformatic and computational approaches was used to deduce the absolute configuration at its eight stereocenters. A putative hybrid PKS/NRPS biosynthetic gene cluster responsible for fatuamide A production was identified from the sequenced genomic DNA of the cultured cyanobacterium. The biosynthetic gene cluster possessed elements that suggested fatuamide A binds metals, and this metallophore property was demonstrated by native metabolomics and indicated a preference for binding copper. The producing strain was found to be highly resistant to toxicity from elevated copper concentrations in culture media.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"322-335"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11877528/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062329","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

SpectroIBIS: Automated Data Processing for Multiconformer Quantum Chemical Spectroscopic Calculations.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub 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":"10.1021/acs.jnatprod.4c01321","url":null,"abstract":"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 1H and 13C 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).","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"495-501"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","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

Controlins I-X, Resin Glycosides from the Seeds of Convolvulus tricolor and Their Biological Activities.

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.4c01182

Yu-Xin Li, Xu-Jia He, Yan Chen, Jin-Ping Gu, Tian-Zi Qi, Hong Gu, Xin-Yi Zhu, Min Yang, Yu-Cheng Gu, Bai Ling, Guang-Tong Chen, Wen-Li Wang, Jia-Lie Luo, Bo-Yi Fan

{"title":"Controlins I-X, Resin Glycosides from the Seeds of Convolvulus tricolor and Their Biological Activities.","authors":"Yu-Xin Li, Xu-Jia He, Yan Chen, Jin-Ping Gu, Tian-Zi Qi, Hong Gu, Xin-Yi Zhu, Min Yang, Yu-Cheng Gu, Bai Ling, Guang-Tong Chen, Wen-Li Wang, Jia-Lie Luo, Bo-Yi Fan","doi":"10.1021/acs.jnatprod.4c01182","DOIUrl":"10.1021/acs.jnatprod.4c01182","url":null,"abstract":"Ten new resin glycosides, controlins I-X (1-10), were isolated from the seeds of Convolvulus tricolor. Their structures were established by spectroscopic analysis as well as by chemical means. Compounds were identified as glycosidic acid methyl esters, considered as artifacts generated via transesterification with MeOH from natural resin glycosides. Compound 1 is the first nonasaccharide resin glycoside, while compounds 2-7 are rare octasaccharide resin glycosides. Compounds 5, 6, and 8 could inhibit the nitric oxide production in lipopolysaccharide-induced BV-2 cells, while compounds 3, 5, and 7 exhibited neuroprotective effects on H2O2-induced damage in PC12 cells. Compounds 6 and 7 could dose-dependently alleviate the dyskinesia in the UM0001 strain of Caenorhabditis elegans, a double transgenic line of Aβ and pro-aggregation tau, suggesting an anti-Alzheimer's activity, reported for resin glycosides for the first time.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"415-426"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143062311","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

Aurovertins from a Marine-Derived Penicillium Species and Nonenzymatic Reactions in Their Formation.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-01-25 DOI: 10.1021/acs.jnatprod.4c01436

Shan Cheng, Yanchao Xu, Meng Kang, Weiming Zhu, Liping Wang, Peng Fu

引用次数: 0

Pestones A and B from a Fungus Pestalotiopsis sp. Bound to Mutant p53 and Changed Its Conformation.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-02-14 DOI: 10.1021/acs.jnatprod.4c01440

Yusaku Sadahiro, Misaki Okubo, Yuki Hitora, Natsuko Hitora-Imamura, Shunsuke Kotani, Sachiko Tsukamoto

{"title":"Pestones A and B from a Fungus Pestalotiopsis sp. Bound to Mutant p53 and Changed Its Conformation.","authors":"Yusaku Sadahiro, Misaki Okubo, Yuki Hitora, Natsuko Hitora-Imamura, Shunsuke Kotani, Sachiko Tsukamoto","doi":"10.1021/acs.jnatprod.4c01440","DOIUrl":"10.1021/acs.jnatprod.4c01440","url":null,"abstract":"Oncogenic mutant p53 is one of the targets for cancer therapy, and the development of anticancer drugs that reactivate mutant p53 is a promising strategy. The extract of fungus Pestalotiopsis sp. changed mutant p53 to wild-type-like p53 in Saos-2 (p53R175H) cells, as shown by fluorescent immunostaining, and bioassay-guided purification of the extract afforded new dimeric epoxyquinoids, pestones A and B (1 and 2), and a known compound, rosnecatrone (3). The relative and absolute configurations of 1 and 2 were determined based on the spectroscopic data and semisynthesis from 3. Compounds 1 and 2 altered the conformation of mutant p53 in Saos-2 (p53R175H) cells, as shown by immunofluorescence staining. The cellular thermal shift assay analysis showed that 1 increased the thermostability of mutant p53 in Saos-2 (p53R175H) cells, suggesting the direct binding of 1 to mutant p53. Compounds 1 and 2 exhibited cytotoxic activities against Saos-2 (p53R175H) cells with IC50 values of 1.0 and 1.1 μM, respectively. Compound 1 was found to induce apoptosis in Saos-2 (p53R175H) cells by flow cytometry analysis and decreased tumor growth in vivo using a mouse model with HuCCT1 (p53R175H) cells.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"546-553"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143424622","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

Correction to "Discovery of Unusual Sesterterpenoids from Colquhounia coccinea var. mollis and Their Metabolic Implications".

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-02-12 DOI: 10.1021/acs.jnatprod.5c00120

Shu-Xi Jing, Ran Fu, Chun-Huan Li, Cedric L Hugelshofer, Yi-Ming Shi, Shi-Hong Luo, Yan-Chun Liu, Yan Liu, Sheng-Hong Li

引用次数: 0

Cyclic Peptide Natural Product Inspired Inhibitors of the Free-Living Amoeba Balamuthia mandrillaris. 受环肽天然产物启发的自由生活变形虫 Balamuthia mandrillaris 抑制剂。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-02-13 DOI: 10.1021/acs.jnatprod.4c00834

Chenyang Lu, Samantha Nelson, Gabriela Coy, Chris Neumann, Elizabeth I Parkinson, Christopher A Rice

{"title":"Cyclic Peptide Natural Product Inspired Inhibitors of the Free-Living Amoeba Balamuthia mandrillaris.","authors":"Chenyang Lu, Samantha Nelson, Gabriela Coy, Chris Neumann, Elizabeth I Parkinson, Christopher A Rice","doi":"10.1021/acs.jnatprod.4c00834","DOIUrl":"10.1021/acs.jnatprod.4c00834","url":null,"abstract":"Balamuthia mandrillaris is a pathogenic free-living amoeba (pFLA) that can cause infection of the central nervous system (CNS), called Balamuthia amoebic encephalitis (BAE), as well as cutaneous and systemic diseases. Patients infected with B. mandrillaris have a high mortality rate due to a lack of effective treatments. A nonoptimized antimicrobial drug regimen is typically recommended; however, it has poor antiparasitic activity and can cause various and severe side effects. Cyclic peptides exhibit a broad spectrum of antimicrobial activities but are underexplored for their antiamoebic activity. In this study, we evaluated the anti-B. mandrillaris effect of Synthetic Natural Product Inspired Cyclic Peptides (SNaPP) mined from ∼500 biosynthetic gene clusters of various bacterial species. The predicted natural product-43 (pNP-43; BICyP1), identified from the SNaPP library, and its derivates displayed a significant inhibition against B. mandrillaris trophozoites, with five pNPs having IC50s ≤ 5 μM. Furthermore, all hit natural product inspired peptides demonstrated minimal to no hemolytic and cytotoxic effects on human red blood cells (RBCs) and immortalized human carcinoma cells, respectfully. Our study is the first to demonstrate the anti-B. mandrillaris effects of cyclic peptides, offering a promising new direction for drug development.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"274-281"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11877501/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143412371","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

Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri. 生物发光蘑菇加特纳新乳菇共轭长链脂肪酸的驱虫潜能

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-01-04 DOI: 10.1021/acs.jnatprod.4c00546

Maria D A Oliveira, Teresinha de Jesus A Dos S Andrade, Joaquim S C Junior, Nerilson Marques Lima, Hugo G Machado, Jioji N Tabudravu, Francisco das Chagas L Pinto, Lucas Fukui-Silva, Monique C Amaro, Josué de Moraes, Dulce Helena S Silva, Antônia Maria das Graças L Citó, Chistiane Mendes Feitosa

{"title":"Anthelmintic Potential of Conjugated Long-Chain Fatty Acids Isolated from the Bioluminescent Mushroom Neonothopanus gardneri.","authors":"Maria D A Oliveira, Teresinha de Jesus A Dos S Andrade, Joaquim S C Junior, Nerilson Marques Lima, Hugo G Machado, Jioji N Tabudravu, Francisco das Chagas L Pinto, Lucas Fukui-Silva, Monique C Amaro, Josué de Moraes, Dulce Helena S Silva, Antônia Maria das Graças L Citó, Chistiane Mendes Feitosa","doi":"10.1021/acs.jnatprod.4c00546","DOIUrl":"10.1021/acs.jnatprod.4c00546","url":null,"abstract":"With praziquantel being the sole available drug for schistosomiasis, identifying novel anthelmintic agents is imperative. A chemical investigation of the fruiting body of the bioluminescent mushroom Neonothopanus gardneri Berk. resulted in the isolation of new conjugated long-chain fatty acids (8E,10E,12S,13S)-12,13-dihydroxy-7-oxo-octadeca-8,10-dienoic acid (1) and (7S,8S,9E,11E)-7,8-dihydroxy-13-oxo-octadeca-9,11-dienoic acid (2) and three previously described compounds, (7R,8R,9Z)-7,8-dihydroxyoctadec-9-enoic acid (3), (2E)-dec-2-ene-1,10-dioic acid (4), and a ketolactone marasmeno-1,15-dione (5). Their planar structures were elucidated based on 1D and 2D NMR and MS/MS spectroscopic analyses. Compound 3 displayed significant antiparasitic activity against Schistosoma mansoni ex vivo (EC50 < 10 μM). No toxicity was observed in mammalian cells or Caenorhabditis elegans.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"255-261"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11877520/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142925810","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

Serinophospholipids: A Third Type of Natural Phospholipid Discovered in a Thermophilic Bacterium.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-02-28 Epub Date: 2025-01-28 DOI: 10.1021/acs.jnatprod.4c01141

Mikhail Vyssotski, Kirill Lagutin, Andrew MacKenzie, Kevin Mitchell, Arran W Stewart, Dawn Scott, Matthew B Stott, Benjamin J Compton

{"title":"Serinophospholipids: A Third Type of Natural Phospholipid Discovered in a Thermophilic Bacterium.","authors":"Mikhail Vyssotski, Kirill Lagutin, Andrew MacKenzie, Kevin Mitchell, Arran W Stewart, Dawn Scott, Matthew B Stott, Benjamin J Compton","doi":"10.1021/acs.jnatprod.4c01141","DOIUrl":"10.1021/acs.jnatprod.4c01141","url":null,"abstract":"Phospholipids are an essential constituent of cells with all life thought to produce these compounds with either a glycerol or sphingoid moiety at their core. For the first time, we demonstrate that a thermophilic bacterium, Limisphaera ngatamarikiensis NGM72.4T, produces a third type of phospholipid, serinophospholipids, which are distinct from glycero- and sphingophospholipids by featuring a serinol backbone instead. We show that the major serinophospholipid metabolites are N,O-diacylserinophospho-N-methylethanolamine and N,O-diacylserinophosphoethanolamine, and that serinophospholipids constitute up to 38% of the phospholipid mass. Furthermore, we demonstrate that these metabolites are further differentiated from \"traditional\" bacterial glycerophospholipids by their backbone configuration. In contrast to bacterial glycerophospholipids, which have an sn-glycerol-3-phosphate (G3P) architecture, the newly discovered serinophospholipids have an (S)-configured serinol core that is equivalent to the sn-glycerol-1-phosphate (G1P) arrangement characteristic of Archaea.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"373-383"},"PeriodicalIF":3.3,"publicationDate":"2025-02-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143057460","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