Journal of Natural Products 最新文献

Ouhanamide, an Antiparasitic Linear Lipopeptide from a Marine Okeania sp. Cyanobacterium. 海洋蓝藻属的抗寄生线状脂肽Ouhanamide。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-16 DOI: 10.1021/acs.jnatprod.5c00281

Mizuho Niiyama, Naoaki Kurisawa, Kairi Umeda, Ghulam Jeelani, Adnan Luthfi Agusta, Tomoyoshi Nozaki, Kiyotake Suenaga

引用次数: 0

Mining for Halogenated Metabolites of Aetokthonos hydrillicola, the "Eagle Killer" Cyanobacterium. “鹰杀手”蓝藻Aetokthonos hydrillicola卤化代谢物的开采。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-16 DOI: 10.1021/acs.jnatprod.5c00161

Franziska Schanbacher, Valerie I C Rebhahn, Markus Schwark, Steffen Breinlinger, Lenka Štenclová, Kristin Röhrborn, Peter Schmieder, Heike Enke, Susan B Wilde, Timo H J Niedermeyer

{"title":"Mining for Halogenated Metabolites of Aetokthonos hydrillicola, the \"Eagle Killer\" Cyanobacterium.","authors":"Franziska Schanbacher, Valerie I C Rebhahn, Markus Schwark, Steffen Breinlinger, Lenka Štenclová, Kristin Röhrborn, Peter Schmieder, Heike Enke, Susan B Wilde, Timo H J Niedermeyer","doi":"10.1021/acs.jnatprod.5c00161","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00161","url":null,"abstract":"The cyanobacterium Aetokthonos hydrillicola has recently become famous as the \"eagle killer\", producing the biindole alkaloid aetokthonotoxin (AETX), a pentabrominated neurotoxin causing the wildlife disease vacuolar myelinopathy. HPLC-HRMS2 analysis of extracts from environmental samples of the cyanobacterium revealed the presence of AETX derivatives and biosynthetic intermediates of the cyanobacterial neurotoxin. Mass spectrometry-based molecular networking and other advanced computational data mining techniques were employed to explore the chemical space of natural AETX derivatives. We identified a total of 43 biosynthetic intermediates and derivatives of AETX, including several iodinated derivatives, a rare halogenation in specialized metabolites of freshwater organisms. Structural characterization of these metabolites showed that most of them are AETX derivatives with varying substitution patterns of the bromo or iodo substituents, but also, AETX biosynthetic intermediates and other biindole derivatives were detected. Cytotoxicity assays of two isolated derivatives and AETX showed that they differ markedly in their activity.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074929","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

Anti-Inflammatory Furylidene Tetronic Acid Derivatives from an Endophytic Fungus Hypoxylon monticulosum ZZ14. 内生真菌Hypoxylon monticulosum ZZ14的抗炎呋喃二烯酸衍生物。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-16 DOI: 10.1021/acs.jnatprod.5c00291

Yufang Bi, Yuelun Xu, Tianzhi Li, Tao Yuan

{"title":"Anti-Inflammatory Furylidene Tetronic Acid Derivatives from an Endophytic Fungus Hypoxylon monticulosum ZZ14.","authors":"Yufang Bi, Yuelun Xu, Tianzhi Li, Tao Yuan","doi":"10.1021/acs.jnatprod.5c00291","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00291","url":null,"abstract":"Naturally occurring furylidene tetronic acids were rare and structurally unique, typically with a furylidene connected to a furan-2,4-(3H, 5H)dione (tetronic acid moiety). In the current study, seven furylidene tetronic acid derivatives (1-7) were isolated and identified from the endophytic fungus Hypoxylon monticulosum ZZ14, including three new ones, hypoxytetronic acids A and B (1 and 2) and 2',3'-dihydronodulisporacid A methyl ester (3). Compounds 1 and 2 possess an unusual skeleton, with two tetrahydrofurans attached to the tetronic acid moiety. Their absolute configurations were elucidated by custom-DP4+ probability analysis of NMR chemical shifts and ECD calculations. Nodulisporacid A methyl ester (7) significantly inhibited the production of interleukin 6 (IL-6), interleukin 10 (IL-10), nitric oxide (NO), and inducible nitric oxide synthase (iNOS), comparable to the positive control dexamethasone. Several analogues of nodulisporacid A methyl ester were synthesized, and structure-activity relationship studies were performed, suggesting that the conjugated fragment of 1/2/3/1'/2'/3' and the methyl ester group may be the pharmacophores.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144074927","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

Cordycepsterols A-C, Anti-Inflammatory C₃₀ Ergosterols with a 6/6/6/5/6-Fused Ring System from Cordyceps militaris. 蛹虫草甾醇a - c，抗炎C30麦角甾醇与6/6/6/5/6-融合环系统。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-15 DOI: 10.1021/acs.jnatprod.5c00452

Zhi-Ang Chen, Hong-Fei Li, Shan-Shan Huang, Tian Jin, Wen-Zhe Xie, Juan He, Tao Feng

引用次数: 0

Discovery of Antibacterial Azaphilone Hybrid Metabolites from Marine-Derived Aspergillus terreus PPS1. 海洋源地曲霉PPS1中抗菌氮蚜酮杂交代谢物的发现。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-08 DOI: 10.1021/acs.jnatprod.5c00187

Yao-Yao Zheng, Xiu Zhang, Ya-Hui Zhang, Meng-Qi Zhang, Zhiqing Liu, Pingyuan Wang, Guang-Shan Yao, Chang-Yun Wang

引用次数: 0

Gut Microbiome-Derived Metabolism Screen System Reveals Dehydrogenation Metabolism of Isorhynchophylline. 肠道微生物衍生代谢筛选系统揭示异羟基苯甲酸脱氢代谢。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-08 DOI: 10.1021/acs.jnatprod.5c00069

Yang Lin, Zheng-Meng Jiang, Xin Liu, Xing-Xing Ji, Ning-Ning Zhang, Zhi-Lu Yu, Shang-Zhen Li, Zi-Yuan Wang, Ze-Bin Weng, Chang-Jiang-Sheng Lai, E-Hu Liu

{"title":"Gut Microbiome-Derived Metabolism Screen System Reveals Dehydrogenation Metabolism of Isorhynchophylline.","authors":"Yang Lin, Zheng-Meng Jiang, Xin Liu, Xing-Xing Ji, Ning-Ning Zhang, Zhi-Lu Yu, Shang-Zhen Li, Zi-Yuan Wang, Ze-Bin Weng, Chang-Jiang-Sheng Lai, E-Hu Liu","doi":"10.1021/acs.jnatprod.5c00069","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00069","url":null,"abstract":"Plant-derived natural products are commonly consumed orally and can be structurally modified by the gut microbiota, potentially altering their biological activity. However, high-throughput studies on their microbial metabolism remain limited. This study applied an in vitro screening system for microbiome-derived metabolism using liquid chromatography-mass spectrometry to analyze the metabolism of 200 natural products by human gut microbiota, and successfully annotated 118 natural products metabolized by gut microbiota. For the first time, metabolic reactions of isorhynchophylline and wilforgine in the intestine were documented. Notably, a substantial increase in the plasma concentration of isocorynoxeine was observed in human microbiota-colonized rats following isorhynchophylline administration compared to those without colonization, suggesting that the dehydrogenation of isorhynchophylline by gut microbiota observed in the in vitro screening system also occurs in vivo. 16S rRNA gene sequencing further revealed an increased abundance of Klebsiella and Escherichia-Shigella following isorhynchophylline administration, suggesting that these genera may influence its microbial transformation or pharmacological activity.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953189","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

Dimeric Acylphloroglucinol Derivatives with Anti-MRSA Activities from Chamelaucium uncinatum. 具有抗mrsa活性的二聚酰基间苯三酚衍生物。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-05 DOI: 10.1021/acs.jnatprod.5c00163

Qian Huang, Ni-Ping Li, Song Ang, Wei Huang, Jia-Qing Cao, Ji-Hong Gu, Lei Wang, Zhen-Long Wu, Wen-Cai Ye

{"title":"Dimeric Acylphloroglucinol Derivatives with Anti-MRSA Activities from Chamelaucium uncinatum.","authors":"Qian Huang, Ni-Ping Li, Song Ang, Wei Huang, Jia-Qing Cao, Ji-Hong Gu, Lei Wang, Zhen-Long Wu, Wen-Cai Ye","doi":"10.1021/acs.jnatprod.5c00163","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00163","url":null,"abstract":"Chamelauciumols A-I (1-9), nine undescribed dimeric acylphloroglucinol derivatives, were isolated from the aerial parts of Chamelaucium uncinatum. Structurally, compound 1 featured a new carbon skeleton characterized by an unprecedented prenyl-substituted methanodibenzo[b,f][1,5]dioxocin core. Compounds 2 and 3 represented new dimeric scaffolds, consisting of two methylated acylphloroglucinol derivatives linked via prenyl units. Compounds 4-9 were new phloroglucinol dimers with various linkage patterns. The structures and absolute configurations of these compounds were elucidated by comprehensive spectroscopic data, single-crystal X-ray diffraction analysis, and electronic circular dichroism calculation. Besides, the antibacterial activities against Gram-positive and Gram-negative bacterial strains of the isolates were evaluated. Compounds 3 and 4 exhibited potent inhibitory effects against methicillin-resistant Staphylococcus aureus with minimum inhibitory concentration values ranging from 0.5 to 1 μg/mL. A preliminary study on the mechanism of action revealed that compounds 3 and 4 exerted anti-MRSA effects through disrupting bacterial cell membrane integrity. Additionally, compounds 3 and 4 also demonstrated remarkable antibiofilm activities.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955517","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

Lyciumines A and B: Two Pyrrole-Fused Alkaloids from the Fruits of Lycium barbarum. 枸杞果实中两种吡咯融合生物碱的研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-04 DOI: 10.1021/acs.jnatprod.5c00385

Yan-Jie Zhu, Xiang-Yang Dai, Yi-Lin Zhao, Yu-Guo Ma, Zhen-Zhu Zhao, Cheng-Fu Su, Zhi-You Hao, Dongdong Wang, Hui Chen

引用次数: 0

Discovery and Biosynthesis of Indole-Functionalized Metabolites from the Human Blood Bacterium, Paracoccus sanguinis, and Their Anti-Skin Aging Activity. 血副球菌吲哚功能化代谢物的发现和生物合成及其抗皮肤衰老活性

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-02 DOI: 10.1021/acs.jnatprod.4c01354

Won Min Lee, Si-Young Ahn, Gyu Sung Lee, InWha Park, Jonghwan Kim, Seung Hwan Lee, Sullim Lee, Chung Sub Kim

{"title":"Discovery and Biosynthesis of Indole-Functionalized Metabolites from the Human Blood Bacterium, Paracoccus sanguinis, and Their Anti-Skin Aging Activity.","authors":"Won Min Lee, Si-Young Ahn, Gyu Sung Lee, InWha Park, Jonghwan Kim, Seung Hwan Lee, Sullim Lee, Chung Sub Kim","doi":"10.1021/acs.jnatprod.4c01354","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01354","url":null,"abstract":"The human microbiome plays a crucial role in health and disease, with microbial metabolites acting as key mediators of physiological processes. While extensive research has focused on gut-derived microbes, the metabolic contributions of blood-derived bacteria remain underexplored. Here, we investigate the facultative anaerobe Paracoccus sanguinis, a Gram-negative bacterium isolated from human blood, and its metabolome, revealing insights into its potential impacts on health and disease. Using advanced analytical methods, we characterized 12 metabolites (1-12), including six novel compounds (1-3, 9, 10, and 12). Biosynthetic studies demonstrated that these metabolites are derived through enzymatic and nonenzymatic pathways. Functional evaluations revealed significant antiaging activities for 1, 6, and 11 in TNF-α-stimulated normal human dermal fibroblasts (NHDFs), including suppression of reactive oxygen species (ROS), inhibition of matrix metalloproteinase-1 (MMP-1) secretion, and reduction of inflammatory cytokines interleukin (IL)-6 and IL-8. Among the tested compounds, 11 exhibited the highest antiaging efficacy, highlighting its potential as a candidate for therapeutic applications targeting skin aging. This study elucidates the biosynthetic pathways of P. sanguinis metabolites and their antiskin aging activity, underscoring their potential in modulating skin health and offering novel insights into the functional roles of blood-derived microbiota in human health.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955063","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

Asteltoxins I-T: Polyketides from a Plant Endophytic Strain of Pochonia bulbillosa. 星钻毒素I-T：一种球孢水蛭内生菌株的聚酮类化合物。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-04-30 DOI: 10.1021/acs.jnatprod.5c00303

Chun-Lun Qin, Zheng Li, Zi-Jian Huang, Jin-Ling Chang, Junjun Liu, Fang-Fang Duan, Xiaoyi Wei, Han-Li Ruan

{"title":"Asteltoxins I-T: Polyketides from a Plant Endophytic Strain of Pochonia bulbillosa.","authors":"Chun-Lun Qin, Zheng Li, Zi-Jian Huang, Jin-Ling Chang, Junjun Liu, Fang-Fang Duan, Xiaoyi Wei, Han-Li Ruan","doi":"10.1021/acs.jnatprod.5c00303","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00303","url":null,"abstract":"Asteltoxins I-T (1-12), 12 asteltoxin-type polyketides, together with four known analogues (13-16), were isolated from an endophytic fungus Pochonia bulbillosa KNI755. Their structures, including absolute configurations, were determined by extensive spectroscopic analysis, single-crystal X-ray diffraction, and electronic circular dichroism (ECD) calculations. Compound 1 featured a tetrahydro-2H-pyran-linked asteltoxin heterodimer incorporating a clavatol unit. Compounds 2 and 3 demonstrated unique tetrahydro-1,4-oxazine-linked asteltoxin heterodimers comprising a diphenyl ether unit. Compounds 4-7 presented unusual 1,4-dioxane-linked asteltoxin heterodimers also containing a diphenyl ether unit. Compounds 1-7 were immunosuppressive against concanavalin A (ConA)-induced T cell proliferation and lipopolysaccharide (LPS)-induced B cell proliferation with EC50 values ranging from 9.2 to 26 μM and from 6.3 to 27 μM, respectively. Compound 1 exhibited inhibitory activity against the HCT116 human cancer cell line with an IC50 value of 10 μM.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955892","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