Journal of Natural Products 最新文献_第2页

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 : 2025-05-23 Epub 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":"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":"1120-1129"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","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

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 : 2025-05-23 Epub 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

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 : 2025-05-23 Epub 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":"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":"1160-1171"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","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

The Pathogenic Fungal Genus Corynespora: A Prolific Source of Bioactive Secondary Metabolites. 致病真菌Corynespora属：生物活性次生代谢物的多产来源。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-24 DOI: 10.1021/acs.jnatprod.5c00145

Yi Hua, Gangao Hu, Titi Ying, Jiangwei Pan, Zhenyi Zhou, Cuixian Zhang, Hong Wang, Bin Wei

引用次数: 0

Total Synthesis and Reconfirmation of the Absolute Configuration of (3R,4S)-6-Acetyl-3-hydroxy-7-methoxy-2,2-dimethylchroman-4-yl(Z)-2-methylbut-2-enoate Isolated from Ageratina grandifolia. 桔梗中(3R,4S)-6-乙酰-3-羟基-7-甲氧基-2,2-二甲基铬-4-基(Z)-2-甲基丁-2-烯酸酯的全合成及绝对构型的再确认

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-28 DOI: 10.1021/acs.jnatprod.5c00269

Sanket S Shete, Swetha Balamurugan, D Srinivasa Reddy

引用次数: 0

Heterologous Expression of the Fellutanine Biosynthetic Gene Cluster and Characterization of the Dual Prenylation of cyclo(l-Trp-l-Trp) by a Single DMATS Enzyme. 费芦氨酸生物合成基因簇的异源表达及单DMATS酶对环（l-Trp-l-Trp）双戊酰化的表征

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-27 DOI: 10.1021/acs.jnatprod.4c01116

Wei-Peng Chen, Wei Lin, Wei Chen, Shu-Zhen Chen, Jian-Bin Xiao, Xing-Tong Chen, Chao Chen, Fan Cai, Ming-Liang Zhang, Qin Li, Huai-Dong Zhang, Li Li, Hui Zhang

{"title":"Heterologous Expression of the Fellutanine Biosynthetic Gene Cluster and Characterization of the Dual Prenylation of cyclo(l-Trp-l-Trp) by a Single DMATS Enzyme.","authors":"Wei-Peng Chen, Wei Lin, Wei Chen, Shu-Zhen Chen, Jian-Bin Xiao, Xing-Tong Chen, Chao Chen, Fan Cai, Ming-Liang Zhang, Qin Li, Huai-Dong Zhang, Li Li, Hui Zhang","doi":"10.1021/acs.jnatprod.4c01116","DOIUrl":"10.1021/acs.jnatprod.4c01116","url":null,"abstract":"2,5-Diketopiperazines (2,5-DKPs) are recognized for their structural rigidity and diverse bioactivities, making them significant in drug discovery. However, the stereochemical complexity of 2,5-DKPs presents challenges in chemical synthesis, particularly concerning indole derivatives such as indole diketopiperazines (IDKPs). Prenylation and oxidation further diversify these structures, enhancing their bioactivity and membrane affinity. Despite recent advances, the biosynthetic pathways of IDKPs, especially those involving dual prenylation, remain inadequately understood. In this study, the fellutanine biosynthetic gene cluster from Nannizzia fulva was cloned and heterologously expressed in Aspergillus nidulans. A partially oxidized intermediate in the fellutanine biosynthetic pathway was characterized. The dimethylallyl tryptophan synthase (DMATS) enzyme FelB was shown to catalyze consecutive prenylations at two C-2 positions of cyclo(l-Trp-l-Trp) in both in vivo and in vitro assays. Additionally, comparative studies with the known DMATS enzyme OkaC revealed differences in the regioselectivity. Furthermore, the biprenylation mechanism of FelB and OkaC was elucidated through molecular docking and active site analysis.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1111-1119"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956549","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

Biosynthesis of a N-Acetylated Tricyclic Carbazole with Antithrombotic Activity. 具有抗血栓活性的n -乙酰化三环咔唑的生物合成。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-22 DOI: 10.1021/acs.jnatprod.5c00179

Jiaming Luo, Yaoyao Shen, Ke Liu, Li Li Hong, Ming Yang, Ning Li, Hai Deng, Hou-Wen Lin, Yongjun Zhou

{"title":"Biosynthesis of a N-Acetylated Tricyclic Carbazole with Antithrombotic Activity.","authors":"Jiaming Luo, Yaoyao Shen, Ke Liu, Li Li Hong, Ming Yang, Ning Li, Hai Deng, Hou-Wen Lin, Yongjun Zhou","doi":"10.1021/acs.jnatprod.5c00179","DOIUrl":"10.1021/acs.jnatprod.5c00179","url":null,"abstract":"Tricyclic carbazoles are significant pharmacophores. Herein, heterologous expression of the carbazole-3,4-quinone (1) biosynthetic pathway in the chassis host Streptomyces albus J1074 yielded a previously chemosynthesized orthoquinone carbazole (2) and three new N-acetylated carbazoles (3-5). Their structures were established by a combination of HR-ESI-MS, NMR, and X-ray crystallographic analysis. Compound 2, the deaminated precursor of 4 and 5, was enzymatically synthesized, indicating the substrate tolerance of the key enzymes in the bacterial tricyclic-carbazole biosynthetic pathway. Mutagenetic analysis revealed an arylamine N-acetyltransferase homologous gene required for the production of compounds 3-5. Bioactivity analysis using the zebrafish model demonstrated that compound 5 has significant antithrombotic activity, potentially by downregulating the genes involved in the platelet activation and coagulation cascade. These findings expand the natural strategies for structural diversification of the tricyclic carbazole alkaloids.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1172-1180"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143952466","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

Bioactive Sesterterpenoids from the Mangrove-Derived Aspergillus sp. GXIMD 03023. 红树曲霉菌GXIMD 03023的生物活性酯萜。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-22 DOI: 10.1021/acs.jnatprod.5c00182

Jia-Li He, Yu Wang, Xiang-Xi Yi, Yu-Man Gan, Yong-Hong Liu, Cheng-Hai Gao, Kai Liu, Meng Bai

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 : 2025-05-23 Epub 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":"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":"1225-1236"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","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

Allantofuranone Biosynthesis and Precursor-Directed Mutasynthesis of Hydroxylated Analogues. 尿囊呋喃酮生物合成及羟基化类似物前体定向突变合成。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-18 DOI: 10.1021/acs.jnatprod.5c00197

Carsten Wieder, Claudia Simon-Sánchez, Johannes C Liermann, Rainer Wiechert, Karsten Andresen, Eckhard Thines, Till Opatz, Anja Schüffler

引用次数: 0