Journal of Natural Products 最新文献

Molecular Networking-Driven Discovery of Antifungal Azaphilone Dimers from the Marine-Derived Fungus Humicola sp. HK1-8. 海洋源真菌Humicola sp. HK1-8抗真菌Azaphilone二聚体的分子网络发现。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-16 DOI: 10.1021/acs.jnatprod.5c00531

Min Chen, Zhong-Hui Li, Xia-Hao Zhu, Li Shen, Long Chen, Tian-Chi Wu, Li-Kui Zhang, Juan-Juan Wang, Chang-Yun Wang

引用次数: 0

Isolation of Verrucosins A-E from a Marine Verrucosispora sp. Reveals a Unifying Biosynthetic Hypothesis for Linear and Macrocyclic Polyketides. 从海洋疣胞菌中分离疣胞素a - e揭示了线性和大环聚酮的统一生物合成假说。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-13 DOI: 10.1021/acs.jnatprod.5c00373

Darren C Holland, Reiko Iizumi, Vikram V Shende, William Fenical

{"title":"Isolation of Verrucosins A-E from a Marine Verrucosispora sp. Reveals a Unifying Biosynthetic Hypothesis for Linear and Macrocyclic Polyketides.","authors":"Darren C Holland, Reiko Iizumi, Vikram V Shende, William Fenical","doi":"10.1021/acs.jnatprod.5c00373","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00373","url":null,"abstract":"As part of our long-standing program evaluating the biosynthetic complexity and biomedical potential of natural products from marine microbes, our attention was drawn to culture extracts from a Verrucosispora sp. (strain TAA-831), which produced multiple compounds with unique UV absorbance signatures and HRMS data. Large-scale fermentation and targeted isolation afforded verrucosins A-E (1-5), a mixture of linear and macrocyclic polyketides whose structures were determined through a synergistic combination of experimental, computational, and genomic approaches. The conserved sequence of methyl malonate and malonate motifs across the verrucosins implied a shared biosynthetic origin despite structural divergence as linear and cyclic congeners. Targeted genome mining revealed a lone type I/type III hybrid polyketide synthase biosynthetic gene cluster, vrs, that is likely responsible for verrucosin production. This revelation demonstrates for the first time that linear 3,5-dihydroxybenzenic (1 and 2) and cyclic ansamycin (3-5) polyketides can be naturally produced by a single biosynthetic gene cluster. The identification of the vrs cluster and bioinformatic prediction of the stereoselectivity of the embedded reductive domains within the modular type I polyketide synthase reinforced the NMR and computational stereochemical assignments for the co-isolates, particularly the stereochemically complex linear verrucosins (1 and 2).","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144281700","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

The Extraordinary Benefit of Nature's Chemistry to Health, Society, and the Economy. 自然化学对健康、社会和经济的非凡益处。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-12 DOI: 10.1021/acs.jnatprod.5c00554

Bradley S Moore, David J Newman

引用次数: 0

Carboxylic Acid Tailoring in Thioquinolobactin Biosynthesis. 巯基喹啉菌素生物合成中的羧酸裁剪。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-11 DOI: 10.1021/acs.jnatprod.5c00331

Xuan Wang, Xiaolin Tian, Jiawei Guo, Fangyuan Cheng, Mingyu Liu, Shanmin Zheng, Yangliu Feng, Ying Lv, Yuanning Li, Shengying Li, Xingwang Zhang

引用次数: 0

Antimycobacterial Muraymycins Isolated from Streptomyces sp. NRRL 30475 Using OSMAC and Precursor-Feeding Strategies. 利用OSMAC和前体取食策略从Streptomyces sp. NRRL 30475中分离出抗细菌的muraymycin。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-10 DOI: 10.1021/acs.jnatprod.5c00405

Fengjuan Zhou, Jiawen Sun, Rui Zhang, Hanyang Peng, Yunyao Ren, Youjuan Zhu, Yongdi Sun, Steven G Van Lanen, Wei Chen, Xiachang Wang

{"title":"Antimycobacterial Muraymycins Isolated from Streptomyces sp. NRRL 30475 Using OSMAC and Precursor-Feeding Strategies.","authors":"Fengjuan Zhou, Jiawen Sun, Rui Zhang, Hanyang Peng, Yunyao Ren, Youjuan Zhu, Yongdi Sun, Steven G Van Lanen, Wei Chen, Xiachang Wang","doi":"10.1021/acs.jnatprod.5c00405","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00405","url":null,"abstract":"Three mutant strains of Streptomyces sp. NRRL 30471 were screened with eight different media based on \"One Strain Many Compounds\" (OSMAC) and precursor-feeding strategies. Five new muraymycins, D5-D9 (4-8), together with three known congeners were isolated and identified from Streptomyces sp. NRRL 30475 using an optimized BPM23A medium containing methionine, leucine, and arginine (each 1.5 g/L). Structures of new compounds were elucidated using HR-MS and NMR spectroscopic data. Muraymycin D6 (5) represents the first natural muraymycin with phosphorylation at the 3'-OH of the ribofuranoside moiety. Muraymycin D9 (8) features a unique dehydrocyclization of the carboxyl of a valine with the epicapreomycidine imide of the peptide moiety, forming an isopropyl hydantoin structure. Except for muraymycin D8 (7), which lacked the ribofuranose, all isolated muraymycins (1-6 and 8) displayed potent antimycobacterial activity against Mycolicibacterium smegmatis (MIC = 2-32 μg/mL). Specifically, the activities of 1-4 and 6 were even better than those of the positive control isoniazid (MIC = 16 μg/mL). Moreover, muraymycins D1, D2, D4, and D5 (1-4) had antimycobacterial effects against M. tuberculosis with MIC values in the range of 8-16 μg/mL. This finding highlights muraymycin nucleoside has potential for the development of antituberculosis antibiotics.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144256644","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

Comptonellins A-H, Highly Potent Antiviral Ternatin-type Cyclopeptides from Comptonella drupacea. Comptonellins A-H：一种高效抗病毒的孔普氏菌ternatin型环肽。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-10 DOI: 10.1021/acs.jnatprod.5c00318

Cécile Apel, Juliano Haddad, Charline Herrscher, Clément Grisel, Justine Girard, Florent Olivon, Cyril Poullain, Jean-François Gallard, Stéphanie Boutet, Fanny Roussi, Sandy Desrat, Chaker El Kalamouni, Marc Litaudon

{"title":"Comptonellins A-H, Highly Potent Antiviral Ternatin-type Cyclopeptides from Comptonella drupacea.","authors":"Cécile Apel, Juliano Haddad, Charline Herrscher, Clément Grisel, Justine Girard, Florent Olivon, Cyril Poullain, Jean-François Gallard, Stéphanie Boutet, Fanny Roussi, Sandy Desrat, Chaker El Kalamouni, Marc Litaudon","doi":"10.1021/acs.jnatprod.5c00318","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00318","url":null,"abstract":"An antiviral screening of plant extracts from Rutaceae and Annonaceae families led to the isolation of a series of new cycloheptapeptides, comptonellins A-H (1-8), along with the known ternatin (9). These compounds were isolated from the ethyl acetate bark extract of Comptonella drupacea (Labill.) Guillaumin, an endemic Rutaceae species of New Caledonia. Following targeted isolation guided by multi-informative molecular networks, the structures of compounds 1-9 were elucidated through a comprehensive analysis of spectroscopic data. This revealed novel molecules featuring previously unreported and noncanonical amino acids. The absolute configuration of stereocenters was partially determined by advanced Marfey's method. Biological evaluation against Zika virus demonstrated the potent antiviral properties of comptonellin A and comptonellins C-G, with IC50 values ranging from 7 to 240 nM. Further investigations revealed that comptonellin A displayed broad-spectrum antiviral activity, inhibiting Dengue virus, Ross River virus, and SARS-CoV-2. These findings highlight comptonellins as promising antiviral scaffolds, supporting further investigation into their therapeutic potential against emerging viral infections.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144264812","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 Aaptamine Analogues from Australian Marine Sponge Aaptos lobata as Mitochondrial Modulators. 来自澳大利亚海绵Aaptos lobata的新的aap胺类似物作为线粒体调节剂。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-10 DOI: 10.1021/acs.jnatprod.5c00364

Emmanuel A Makinde, Linlin Ma, George D Mellick, Merrick Ekins, Yunjiang Feng

{"title":"New Aaptamine Analogues from Australian Marine Sponge Aaptos lobata as Mitochondrial Modulators.","authors":"Emmanuel A Makinde, Linlin Ma, George D Mellick, Merrick Ekins, Yunjiang Feng","doi":"10.1021/acs.jnatprod.5c00364","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00364","url":null,"abstract":"Mitochondrial dysfunction has been implicated in many neurodegenerative diseases, such as Parkinson's disease, and mitoprotective metabolites may hold the key to potentially effective treatments. In this study, comprehensive chemical investigation of an Australian marine sponge, Aaptos lobata, led to the isolation of three new aaptamine-type 1H-benzo[de][1,6]-naphthyridine alkaloids, namely 3,6'-diaaptamine (2), aaptanone A (3) and 8-demethylaaptamine (4), alongside four known compounds, 8,8',9,9'-tetramethoxy-1H,1'H-3,3'-bibenzo[de][1,6]naphthyridine (5), aaptanone (6), 9-methoxy-N-demethylaaptanone (7) and aaptamine (1). The structures of these compounds were determined using an analysis of spectroscopic data. Biological evaluation in SH-SY5Y using 6-OHDA as neurotoxin revealed that compounds 2, 3, 4, 5 and 7 displayed potent mitoprotective activity, effectively attenuating cell death with apparent EC50 values ranging from 0.05 μM to 1.06 μM. These compounds also mitigated mitochondrial membrane depolarization with apparent EC50 values between 0.021 μM and 0.78 μM. These findings highlight the therapeutic potential of A. lobata-derived alkaloids as promising candidates for mitochondria-targeted drug development.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144264813","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

Molecular Networking Reveals Indolo-Sesquiterpene Hybrids from the Marine-Derived Fungus Aspergillus terreus N4-9. 海洋来源真菌土曲霉N4-9的吲哚-倍半萜杂合体的分子网络研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-10 DOI: 10.1021/acs.jnatprod.5c00423

Min Chen, Bao-Cong Hao, Ruo-Nan Ji, Long Chen, Xiao-Jian Zhou, Li Shen, Juan-Juan Wang, Li-Kui Zhang

{"title":"Molecular Networking Reveals Indolo-Sesquiterpene Hybrids from the Marine-Derived Fungus Aspergillus terreus N4-9.","authors":"Min Chen, Bao-Cong Hao, Ruo-Nan Ji, Long Chen, Xiao-Jian Zhou, Li Shen, Juan-Juan Wang, Li-Kui Zhang","doi":"10.1021/acs.jnatprod.5c00423","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00423","url":null,"abstract":"Tandem mass spectrometry (MS/MS)-based molecular networking has emerged as a powerful tool for rapid dereplication of known compounds and discovery of novel structural analogues within the same metabolite class. In this study, the chemical diversity of indolo-sesquiterpene hybrids from the mangrove rhizosphere soil-derived fungus, Aspergillus terreus N4-9, was investigated by using molecular networking strategies. The known indolo-sesquiterpene hybrid terreuside B (1) along with three new analogues, terreusides C-E (2-4), were targeted isolation from the fungal cultures. Additionally, three putative new congeners, terreusides F-H (8-10), were tentatively identified through systematic analysis of their characteristic MS/MS fragmentation patterns. Detailed fragmentation studies revealed two predominant cleavage pathways for these hybrids related to fracture of the methylene bridge connecting Rings A and B (Type I) and furan opening in Ring C (Type II). Compound 2 demonstrated significant growth inhibitory activity against human gastric cancer SGC-7901 cells with an IC50 value of 6.25 μM.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144256645","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

Zoanthamine-Type Alkaloids Derived from Cultured Zoanthus kuroshio with Therapeutic Potential Against Osteoporosis. 从培养的黑斑草中提取的抗骨质疏松的斑蝥素类生物碱。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-09 DOI: 10.1021/acs.jnatprod.5c00457

Ngoc-Thac Pham, Bo-Rong Peng, Huong-Giang Le, You-Song Cheng, Yun-Shiuan Chen, Thanh Hao Huynh, Lo-Yun Chen, Le Anh Tuan Nguyen, Dang T Nguyen, Yu-Chia Chang, Jui-Hsin Su, Mohamed El-Shazly, Mei-Hsien Lee, Kuei-Hung Lai

{"title":"Zoanthamine-Type Alkaloids Derived from Cultured Zoanthus kuroshio with Therapeutic Potential Against Osteoporosis.","authors":"Ngoc-Thac Pham, Bo-Rong Peng, Huong-Giang Le, You-Song Cheng, Yun-Shiuan Chen, Thanh Hao Huynh, Lo-Yun Chen, Le Anh Tuan Nguyen, Dang T Nguyen, Yu-Chia Chang, Jui-Hsin Su, Mohamed El-Shazly, Mei-Hsien Lee, Kuei-Hung Lai","doi":"10.1021/acs.jnatprod.5c00457","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00457","url":null,"abstract":"Extracts of the zoanthid from Zoanthus kuroshio (ZK) exhibited significant in vitro antiosteoporotic activity in MG-63 cells, prompting the use of Global Natural Products Social Molecular Networking (GNPS) to identify alkaloid-rich fractions. Subsequently, five new zoanthamine-type alkaloids, norzoabenzaldehyde (1), norzoazepanol (2), 3-acetoxynorzoanthaminone (3), 11-hydroxynorzoanthamide B (4), and 11-hydroxyzoanthamide B (5), were isolated. Structural elucidation was achieved by spectroscopic analyses, time-dependent density functional theory nuclear magnetic resonance (TDDFT-NMR) calculations, and electronic circular dichroism (ECD). The alkaloid 3-hydroxynorzoanthamine exhibited notable alkaline phosphatase activity and promoted mineralization, with an IC50 value of 20 μM, underscoring its potential as a promising lead compound for the development of osteoporosis therapeutics.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144256646","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 Mining of Fungal Aza-Polycyclic Natural Products Derived from Arginine-Containing Cyclodipeptides. 含精氨酸环二肽真菌aza -多环天然产物的基因组挖掘。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-06-09 DOI: 10.1021/acs.jnatprod.5c00455

Kanji Niwa, David A Delgadillo, Danielle A Yee, Chuhang Luo, Flora Fan, Kunal K Jha, Hosea M Nelson, Yi Tang

{"title":"Genome Mining of Fungal Aza-Polycyclic Natural Products Derived from Arginine-Containing Cyclodipeptides.","authors":"Kanji Niwa, David A Delgadillo, Danielle A Yee, Chuhang Luo, Flora Fan, Kunal K Jha, Hosea M Nelson, Yi Tang","doi":"10.1021/acs.jnatprod.5c00455","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00455","url":null,"abstract":"Arginine-containing cyclodipeptide synthases (RCDPSs) from fungi constitute a new family of tRNA-dependent enzymes that can biosynthesize cyclo-Arg-Xaa dipeptides. The incorporation of an arginine residue significantly expands the chemical space of guanidine-containing natural products. Here, we mined fungal biosynthetic gene clusters (BGCs) containing different RCDPS to discover aza-polycyclic natural products. The pno BGC from Aspergillus pseudonomius produced pentacyclic pyrroloindoline diketopiperazines (DKPs) of which the arginine side chain is oxidatively cyclized into a guanidino-proline. Two RCDPS-encoding BGCs, car and esh from Aspergillus carlsbadensis and Eupenicillium shearii, respectively, produced DKPs connected to five- and seven-membered spirocycles as a result of oxidative cyclization of the guanidino group catalyzed by α-ketoglutarate/Fe(II)-dependent oxygenases. The esh pathway involves a tandem cyclization and epimerization to generate the guanidino-bridged tricyclo-[3.31,2.2.2]-piperazinedione core. The aza-polycyclic structures characterized in this work demonstrate the potential of using RCDPS as a starting point for the discovery of new natural products.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144245350","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