Journal of Natural Products 最新文献_第8页

Discovery of Rearranged Steroids from Cultures of Penicillium soli as Inhibitors of Idiopathic Pulmonary Fibrosis 从青霉菌培养物中发现重排类固醇作为特发性肺纤维化抑制剂。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-26 DOI: 10.1021/acs.jnatprod.6c00334

Ming Chen, Xueqi Lan, Xue Gong, Xinye Huang, Dechao Meng, Weiguang Sun, Chao Zhao*, Changxing Qi* and Yonghui Zhang*,

{"title":"Discovery of Rearranged Steroids from Cultures of Penicillium soli as Inhibitors of Idiopathic Pulmonary Fibrosis","authors":"Ming Chen, Xueqi Lan, Xue Gong, Xinye Huang, Dechao Meng, Weiguang Sun, Chao Zhao*, Changxing Qi* and Yonghui Zhang*, ","doi":"10.1021/acs.jnatprod.6c00334","DOIUrl":"10.1021/acs.jnatprod.6c00334","url":null,"abstract":"Idiopathic pulmonary fibrosis (IPF) is a severe lung disease characterized by high disability and mortality rates. During our ongoing research on bioactive natural products from fungi, six ergosterol-type steroids (1–6), including five previously unknown compounds, penisterones A–E (1–5), were isolated from cultures of Penicillium soli TJ507, using HSQC-based DeepSAT analysis. The structures of these compounds were elucidated via comprehensive spectroscopic analyses, NMR chemical shift calculations with DP4+ probability analysis, single-crystal X-ray diffraction, and electronic circular dichroism calculations. Compound 1 is the first ergosterol-type natural product with a 14,15-seco framework based on a 1(10→6)-abeo-18,22-cyclosterol core. Compound 6 exhibited antifibrotic activity by suppressing TGF-β1-driven fibroblast activation and extracellular matrix production in NIH/3T3 cells. The same compound alleviated the pathological changes in the bleomycin-induced IPF mice, that might provide a potential lead compound in the drug development for IPF.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1857–1867"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148024903","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 “An Unusual Ring Pattern in the Rosβ Lanthipeptide of the Two-Component Lantibiotic Roseocin” 对“双组分玫瑰红素的玫瑰β蓝肽中不寻常的环状模式”的修正。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-19 DOI: 10.1021/acs.jnatprod.6c00581

Emily K. Desormeaux, Lingyang Zhu, Youran Luo, Sandeep Chaudhary, Dipti Sareen and Wilfred A. van der Donk*,

引用次数: 0

Enantioselective NP-HPLC Resolution of Usnic Acid and Isousnic Acid with Revised Absolute Configuration and NMR Assignment of Isousnic Acid 用修正的异音酸绝对构型和核磁共振配位法分离异音酸和异音酸。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-06-09 DOI: 10.1021/acs.jnatprod.6c00283

Dagmar Ísleifsdóttir, Maonian Xu, Kenichi Ishida, Rebecca L. Davis, Maia Biwersi, John L. Sorensen, Elvar Örn Viktorsson and Elín Soffía Ólafsdóttir*,

{"title":"Enantioselective NP-HPLC Resolution of Usnic Acid and Isousnic Acid with Revised Absolute Configuration and NMR Assignment of Isousnic Acid","authors":"Dagmar Ísleifsdóttir, Maonian Xu, Kenichi Ishida, Rebecca L. Davis, Maia Biwersi, John L. Sorensen, Elvar Örn Viktorsson and Elín Soffía Ólafsdóttir*, ","doi":"10.1021/acs.jnatprod.6c00283","DOIUrl":"10.1021/acs.jnatprod.6c00283","url":null,"abstract":"Usnic acid (UA) enantiomers are abundant lichen compounds with diverse bioactivities, including potent antibiotic effects. In contrast, isousnic acid (isoUA) enantiomers are relatively scarce, and their biological functions and biosynthetic mechanisms remain poorly understood. Future studies on UA isomers would greatly benefit from a robust, optimized, and validated enantioselective chromatographic method that resolves all four isomers in a single run. This study aimed to (i) assign the absolute configuration of isoUA through integrated experimental and computational ECD analyses; (ii) perform a comprehensive structural characterization and clarify NMR assignments of isoUA relative to previous reports; (iii) develop and validate a chiral normal-phase HPLC method for simultaneous separation of (+)-isoUA (1), (−)-isoUA (2), (+)-UA (3), and (−)-UA (4). The absolute configurations of the isoUA enantiomers were assigned as (S) for (+)-isoUA (1) and (R) for (−)-isoUA (2). Examination of NMR data for isoUA revealed misassignments in some prior studies. Importantly, the developed HPLC method achieved baseline resolution of 1–4, enabling quantification in lichen specimens. This study emphasizes the importance of accurate enantiomeric structural elucidation before chiral method development and paves the way for future biosynthetic investigations and the precise detection of these enantiomers in lichen samples.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1802–1810"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148209244","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

Engineering Bacillus Subtilis and Fermentation Process Optimization for High-Level Production of Pulcherriminic Acid 工程枯草芽孢杆菌及高产白垩二酸发酵工艺优化。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-06-05 DOI: 10.1021/acs.jnatprod.6c00175

Xinglei Zhuang, Shuangxiao Chen, Yukang Xie, Tong Zhang, Aleksandra Djukić-Vuković, Qiyuan Chen, Minghua Ji* and Junsong Sun*,

{"title":"Engineering Bacillus Subtilis and Fermentation Process Optimization for High-Level Production of Pulcherriminic Acid","authors":"Xinglei Zhuang, Shuangxiao Chen, Yukang Xie, Tong Zhang, Aleksandra Djukić-Vuković, Qiyuan Chen, Minghua Ji* and Junsong Sun*, ","doi":"10.1021/acs.jnatprod.6c00175","DOIUrl":"10.1021/acs.jnatprod.6c00175","url":null,"abstract":"Pulcherriminic acid (PA) is a typical microbial natural cyclic dipeptide and secondary metabolite. It serves as the biosynthetic precursor of pulcherrimin, an iron-chelating siderophore with promising potential for agricultural biocontrol. Low inherent biosynthesis severely limits its practical exploitation as a bioactive natural product. Here, we screened five Bacillus subtilis strains and selected 164T7P as the metabolic engineering chassis. Replacing the native promoter of the yvmC-cypX cluster with the xylose-inducible T7 promoter increased PA titer by 7.18-fold to 0.201 g/L. Knockout of abrB or spoIVB enhanced PA formation, whereas codY deletion suppressed its biosynthesis. Further optimization of carbon source, l-leucine supplementation and FeCl3 concentration raised the titer to 1.284 g/L at 0.6 g/L FeCl3. With glycerol as the primary feedstock supplemented with l-leucine and FeCl3, fed-batch fermentation in a 5-L bioreactor achieved a final PA titer of 3.91 g/L, the highest reported titer of this natural product to date. This study establishes an efficient biosynthetic platform for high-level production of PA and facilitates further development of this bioactive microbial natural product.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1738–1746"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148161158","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

Anthracaurisin A─Discovery of a Cytotoxic Nor-Sesquiterpene Dimer from Patagonian Anthracophyllum discolor 炭疽菌素A─从巴塔哥尼亚炭疽菌中发现的一种细胞毒性非倍半萜二聚体。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-06-11 DOI: 10.1021/acs.jnatprod.6c00531

Bastien Petit, Ines Michrafy, Jordan Nafie, Grayce E. Dyer, Erin M. Marshall, Cristian Riquelme, Jaime R. Cabrera-Pardo, James A. Strother and Sandra Loesgen*,

{"title":"Anthracaurisin A─Discovery of a Cytotoxic Nor-Sesquiterpene Dimer from Patagonian Anthracophyllum discolor","authors":"Bastien Petit, Ines Michrafy, Jordan Nafie, Grayce E. Dyer, Erin M. Marshall, Cristian Riquelme, Jaime R. Cabrera-Pardo, James A. Strother and Sandra Loesgen*, ","doi":"10.1021/acs.jnatprod.6c00531","DOIUrl":"10.1021/acs.jnatprod.6c00531","url":null,"abstract":"Fungal natural products, also called secondary metabolites (SMs), continue to inspire chemists and drug development. Around 30,000 fungal SMs are known, mainly from filamentous fungi of the phylum Ascomycota. Only 5% of all fungal species are described today, and even fewer have been cultured or chemically screened, which makes fungi an untapped reservoir for chemical discovery. The phylum Basidiomycota harbors chemically talented fungi such as the psilocybin producer Psilocybe cubensis (Agaricales, Hymenogastraceae), but other members like the genus Anthracophyllum (Agaricales, Omphalotaceae) remain largely genetically and chemically underexplored although new species are being discovered frequently. Here, we present the chemical and bioactivity exploration of a Chilean Anthracophyllum discolor fungus. We discovered anthracaurisin A, the first fungal nor-sesquiterpene homodimer with potent cytotoxic activity in vitro and in vivo, isolated one new and several known illudins, and established their absolute configurations.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1995–2007"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.6c00531","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148215511","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

Discovery of Quebrachamine-like Indole Alkaloids with Ferroptosis Inhibitory Activity from Catharanthus roseus Using HSQC-Based DeepSAT 利用HSQC-Based DeepSAT技术发现玫瑰花中具有抑制铁下垂活性的类蒽醌吲哚生物碱。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-20 DOI: 10.1021/acs.jnatprod.6c00088

Feng Qin, Fan-Fan Wang, Jianan Guo, Gang Wei, Zhaoguo Hong, Qiu-Rong Liu, Dezhao Lu, Cai-Yi Wang*, Xiao-Dong Luo* and Heng-Shan Wang*,

引用次数: 0

Cell-Free Synthesis of Cannabistilbene I: A Dual Acting Anti-Inflammatory from Cannabis sativa 大麻二酚I的无细胞合成：一种从大麻中提取的双作用抗炎物质。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-15 DOI: 10.1021/acs.jnatprod.6c00318

Kelly F. Boddington, Eric Soubeyrand, Kristen Van Gelder, Colby Perrin, Taylor J. B. Forrester, Jennifer Holborn, José A. Casaretto, M. Sameer Al-Abdul-Wahid, Mathew L. Piotrowski, Jakob Magolan, Jasmin Lalonde, Matthew S. Kimber, Steven J. Rothstein and Tariq A. Akhtar*,

{"title":"Cell-Free Synthesis of Cannabistilbene I: A Dual Acting Anti-Inflammatory from Cannabis sativa","authors":"Kelly F. Boddington, Eric Soubeyrand, Kristen Van Gelder, Colby Perrin, Taylor J. B. Forrester, Jennifer Holborn, José A. Casaretto, M. Sameer Al-Abdul-Wahid, Mathew L. Piotrowski, Jakob Magolan, Jasmin Lalonde, Matthew S. Kimber, Steven J. Rothstein and Tariq A. Akhtar*, ","doi":"10.1021/acs.jnatprod.6c00318","DOIUrl":"10.1021/acs.jnatprod.6c00318","url":null,"abstract":"Despite the potential of Cannabis bibenzyls to remedy acute and chronic inflammation, their relative scarcity, in planta, has hindered applications for them in mainstream therapeutic efforts. Here, we describe the biocatalytic synthesis of cannabistilbene I (1), a prototypical Cannabis bibenzyl, and demonstrate its utility as an anti-inflammatory agent. A Cannabis O-methyltransferase (CsOMT1) was first identified that catalyzes the 3-hydroxymethylation of dihydroresveratrol (2) to produce pinobistilbene (3). Structural characterization of CsOMT1 revealed that the substrate-binding pocket requires the ethyl bridge on 2 to twist with a dihedral angle of −110°, thereby explaining why less flexible aromatics such as stilbenes serve as poor enzymatic substrates. Next, a prenyltransferase (CloQ) from the Gram-positive bacterium Streptomyces was shown to prenylate the 3′-position of the B-ring on 3 into 1. Using these two enzymes, a cell-free method was then developed to synthesize 1 and the compound was shown to inhibit both microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase enzyme activity, in vitro, more effectively than the leading commercially available inhibitors. Together, these results establish a platform for producing cannabistilbene I (1) that circumvents the challenges of traditional “chemical synthesis”, and which is amenable to produce similar value-added compounds that are not easily accessible from nature.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1842–1856"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.6c00318","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147947200","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

Design and Synthesis of Verlamelin A Derivatives with Antifungal Activity against Alternaria spp. 具有抗真菌活性的Verlamelin A衍生物的设计与合成。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-05-29 DOI: 10.1021/acs.jnatprod.6c00381

Xin Sun, Yuecheng Fang, Huayan Xu, Junfeng Wang, Bin Wang*, Yonghong Liu* and Shengrong Liao*,

{"title":"Design and Synthesis of Verlamelin A Derivatives with Antifungal Activity against Alternaria spp.","authors":"Xin Sun, Yuecheng Fang, Huayan Xu, Junfeng Wang, Bin Wang*, Yonghong Liu* and Shengrong Liao*, ","doi":"10.1021/acs.jnatprod.6c00381","DOIUrl":"10.1021/acs.jnatprod.6c00381","url":null,"abstract":"Verlamelin A is a macrocyclic antifungal depsipeptide. In this study, a series of derivatives (1a–15a, 17a, 1b– 17b) were developed by replacing the l-Gln residue in verlamelin A with other proteinogenic l-amino acids. Biological evaluation revealed that compound 8b, substituted with an l-Thr residue, exhibited enhanced antifungal activity and an expanded spectrum against four plant pathogens─Alternaria alternata, Alternaria solani, Alternaria tenuissima, and Alternaria longipes─with minimum inhibitory concentration (MIC) values ranging from 4 to 32 μg/mL. Compound 12b, substituted with an l-Glu residue, showed antifungal activity against A. alternata, A. solani, and A. longipes, with MIC values ranging from 2 to 64 μg/mL. Both compounds demonstrated dose-dependent inhibitory effects on the mycelial growth of A. tenuissima and A. alternata, respectively. Structure–activity relationship studies indicated that compounds with the R configuration at the C-5 position of the tetradecanoic acid moiety exhibited broader spectrum of activity and greater potency than their S-configured counterparts. In vivo fruit infection assays showed that compounds 8b and 12b possessed curative efficacy, protecting tomatoes and apples from damage caused by these pathogens. With low toxicity, compounds 8b and 12b represent promising lead compounds for further development as antifungal agents to combat pathogens in agriculture.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1913–1923"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148051305","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

Pyrenoids A–P: Ring-Rearranged Tropolonic Sesquiterpenoids with Anti-Neuroinflammatory Effects from the Marine Mesophotic Sponge-Associated Fungus Pyrenochaeta sp. NBUF199 类Pyrenoids A-P：具有抗神经炎症作用的环重排Tropolonic倍半萜类化合物，来自海洋中孔海绵相关真菌Pyrenochaeta sp. nbuf1999。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-06-11 DOI: 10.1021/acs.jnatprod.6c00524

Chanting Lai, Jiaxin Tian, Qianjing Zheng, Shuji Huang, Rong Zhang, Rundong Liu, Bin Wu, Wenhan Lin, Shan He, Weiyi Wang*, Pengcheng Yan* and Tingting Wang*,

{"title":"Pyrenoids A–P: Ring-Rearranged Tropolonic Sesquiterpenoids with Anti-Neuroinflammatory Effects from the Marine Mesophotic Sponge-Associated Fungus Pyrenochaeta sp. NBUF199","authors":"Chanting Lai, Jiaxin Tian, Qianjing Zheng, Shuji Huang, Rong Zhang, Rundong Liu, Bin Wu, Wenhan Lin, Shan He, Weiyi Wang*, Pengcheng Yan* and Tingting Wang*, ","doi":"10.1021/acs.jnatprod.6c00524","DOIUrl":"10.1021/acs.jnatprod.6c00524","url":null,"abstract":"Sixteen new ring-rearranged tropolonic sesquiterpenoids, pyrenoids A–P (1–16), along with four known congeners (17–20), were isolated from the fungus Pyrenochaeta sp. associated with the mesophotic sponge Cinachyrella sp. at a depth of 71.8 m. Their structures were elucidated by detailed spectroscopic analysis, single-crystal X-ray diffraction studies, and quantum chemical calculations. Pyrenoids A–J (1–10) are sesquiterpene-tropolone hybrids featuring a ring-rearranged tropolone moiety that forms a new 5/5 bicyclic system. In contrast, pyrenoid K (11) possesses a new ring-contracted framework resulting from the transformation of a seven-membered ring to a five-membered tropolone unit. Biological evaluation revealed that pyrenoid C (3) dose-dependently suppressed lipopolysaccharide (LPS)-induced production of NO and pro-inflammatory cytokines (IL-1β, IL-6, and TNF-α) in BV-2 microglial cells at noncytotoxic concentrations. Further mechanistic investigations, guided by transcriptomic profiling, indicated that this antineuroinflammatory effect is mediated through the suppression of NF-κB signaling by inhibiting p65 phosphorylation at Ser536 and its nuclear translocation.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"89 6","pages":"1983–1994"},"PeriodicalIF":3.7,"publicationDate":"2026-06-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148222100","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 the 5-Chlorokynurenine Pathway in Lodopyridone Biosynthesis Lodopyridone生物合成中5-氯尿氨酸途径的发现。

IF 3.7 2区生物学

Journal of Natural Products Pub Date : 2026-06-26 Epub Date: 2026-06-12 DOI: 10.1021/acs.jnatprod.6c00490

Mariah J. Avila, Tian Lan and Bradley S. Moore*,

引用次数: 0