Journal of Natural Products 最新文献

Isolation and Identification of Xanthone, Benzofuran, and Spirolactone Derivatives from Dinemasporium parastrigosum KT4144 and Their Plausible Biosynthetic Pathways. parastrigosum KT4144中山酮、苯并呋喃和螺内酯衍生物的分离鉴定及其生物合成途径

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-26 DOI: 10.1021/acs.jnatprod.5c00376

Kosei Kirisawa, Shusuke Sato, Atsushi Minami, Hayato Maeda, Kazuaki Tanaka, Masaru Hashimoto

{"title":"Isolation and Identification of Xanthone, Benzofuran, and Spirolactone Derivatives from Dinemasporium parastrigosum KT4144 and Their Plausible Biosynthetic Pathways.","authors":"Kosei Kirisawa, Shusuke Sato, Atsushi Minami, Hayato Maeda, Kazuaki Tanaka, Masaru Hashimoto","doi":"10.1021/acs.jnatprod.5c00376","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00376","url":null,"abstract":"The structurally distinct dinemaxanthones A (1) and B (2), dinemafuran (3), and dinemaspirone (4) were isolated from the fungus Dinemasporium parastrigosum KT4144. Their structures were elucidated primarily through spectroscopic analyses and validated via NMR chemical shift calculations. These analyses revealed that while the density functional theory (DFT) functional ωB97X-D, which has previously yielded reliable results, tends to overestimate van der Waals interactions in highly conformationally flexible compounds, leading to increased chemical shift deviations between the calculated and experimental data. In contrast, the more traditional B3LYP functional more accurately reproduced their conformational distributions, yielding more preferable results. Additionally, electron circular dichroism (ECD) spectral computations established the absolute configurations of 1-4. Structural characterization indicated that these metabolites belong to the xanthone family of fungal natural products. Genome sequence analysis of the producer strain provided insights into their biosynthetic origins, suggesting a pathway from the common intermediate monodictyphenone (6) to compounds 1-4.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.3,"publicationDate":"2025-05-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144148667","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

Peganutonin A: Computationally Informed Synthesis of Its Revised Structure. 聚脲素A：其修正结构的计算信息合成。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-04-25 DOI: 10.1021/acs.jnatprod.5c00322

N Sathya Sai Saranya, Rahul Choudhury, Prathmesh R Supekar, Srinivas Beduru, Craig M Williams, Mikhail E Elyashberg, Andrei G Kutateladze, Roderick W Bates, D Srinivasa Reddy

引用次数: 0

Combining the Strengths of MS and NMR in Biochemometrics: A Case Study on Buddleja officinalis. 在生物化学计量学中结合 MS 和 NMR 的优势：百日草案例研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2024-11-06 DOI: 10.1021/acs.jnatprod.4c00847

Andreas Wasilewicz, Alexander Areesanan, Benjamin Kirchweger, Sven Nicolay, Eva Waltenberger, Mehdi A Beniddir, Carsten Gründemann, Judith M Rollinger, Ulrike Grienke

{"title":"Combining the Strengths of MS and NMR in Biochemometrics: A Case Study on Buddleja officinalis.","authors":"Andreas Wasilewicz, Alexander Areesanan, Benjamin Kirchweger, Sven Nicolay, Eva Waltenberger, Mehdi A Beniddir, Carsten Gründemann, Judith M Rollinger, Ulrike Grienke","doi":"10.1021/acs.jnatprod.4c00847","DOIUrl":"10.1021/acs.jnatprod.4c00847","url":null,"abstract":"Biochemometrics has emerged as promising strategy for the targeted identification of bioactive constituents from natural sources. It is based on the correlation of bioactivity data with chemical data to reveal constituents contributing to activity. Providing complementary data and structural information, MS- and NMR-based biochemometric approaches have both been separately applied in the past. The herein presented study is dedicated to the evaluation of a combined MS- and NMR-based biochemometric workflow for the unambiguous identification of bioactives. As an example, a flower extract of Buddleja officinalis Maxim. was selected to unravel bioactive constituents in the context of dry eye disease pathology. While NMR-based biochemometrics relies on heterocovariance analysis (HetCA) of 1H NMR spectra using the previously established ELINA approach, a biochemometric molecular network was generated for the MS-based approach. Both analyses were performed in parallel and were ultimately combined to increase their power to identify the bioactive constituents from the complex mixture. As a result, phenylethanoid glycosides and triterpene saponins were discovered as main contributors for the antioxidant and cytotoxic effects of the extract. This article illustrates the advantages, opportunities, and limitations of MS and NMR in the context of biochemometrics.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1099-1110"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142580834","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

Contignasterines, Anti-Inflammatory 2-Aminoimidazole Steroids from the Sponge Neopetrosia cf. rava Collected in the Bismarck Sea. 俾斯麦海新褐藻中含有抗炎的2-氨基咪唑类甾体。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-03-07 DOI: 10.1021/acs.jnatprod.5c00118

Juan Ortega-Vidal, Maggie M Reddy, Nadia Pérez-Fuentes, Rebeca Alvariño, Svenja Burth, Amparo Alfonso, Carmen Vale, Jorge R Virués-Segovia, Augustine Mungkaje, Luis M Botana, Olivier P Thomas

引用次数: 0

Isoechinulin-Type Diketopiperazines with Anti-monocyte Adhesion Activities from a Sponge-Associated Aspergillus sp. 海绵相关曲霉菌抗单核细胞粘附活性的异青霉素型二酮哌嗪类。

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.5c00077

Weihao Chen, Jianheng Ma, Mengjing Cong, Xiaoyan Pang, Xiuping Lin, Shengrong Liao, Bin Yang, Xuefeng Zhou, Junfeng Wang, Yonghong Liu

{"title":"Isoechinulin-Type Diketopiperazines with Anti-monocyte Adhesion Activities from a Sponge-Associated Aspergillus sp.","authors":"Weihao Chen, Jianheng Ma, Mengjing Cong, Xiaoyan Pang, Xiuping Lin, Shengrong Liao, Bin Yang, Xuefeng Zhou, Junfeng Wang, Yonghong Liu","doi":"10.1021/acs.jnatprod.5c00077","DOIUrl":"10.1021/acs.jnatprod.5c00077","url":null,"abstract":"Seven new isoechinulin-type diketopiperazines (DKPs), asperfatsines A-G (1-7), along with five known analogues (8-12), were isolated from cultures of a sponge-associated Aspergillus sp. SCSIO41034. The structural elucidations, including the determination of absolute configurations, were accomplished by comprehensive analyses utilizing NMR spectroscopy, HRESIMS, gas chromatography-mass spectrometry (GC-MS), Marfey's method, Mo2(OAc)4-induced circular dichroism, modified Mosher's method, and electronic circular dichroism (ECD) calculations. Asperfatsines A-C represent the first three cases of isoechinulin-type DKPs possessing three distinct long-chain fatty acid moieties. Pretreatment with 1, 3, 4, and 8 in tumor necrosis factor α (TNF-α)-stimulated human umbilical vein endothelial cells led to a reduction in the adhesion of THP-1 monocytes. Compound 4 downregulates the gene expression of cell adhesion molecules in a dose-dependent manner. These findings suggest that isoechinulin-type DKPs represent promising candidates with core molecular frameworks that may serve as a foundation for developing antivascular inflammation therapies.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1143-1152"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143950744","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 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 : 2025-05-23 Epub 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 : 2025-05-23 Epub 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":"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":"1130-1142"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","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

Precursor-Directed Biosynthesis of Phenylpyrrole Analogues in Myrothecium verrucaria. 苯基吡咯类似物在疣状结核分枝杆菌中的前体定向生物合成。

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.5c00238

Miaomiao Chai, Wei Li, Bing Wang, Xiaomin Zhang, Dehai Li, Zhenzhen Zhang, Zhenhui Wang, Xueqian He

引用次数: 0

Two-Step Flow Amidation of Natural Phenolic Acids as Antiradical and Antimicrobial Agents. 天然酚酸作为抗自由基和抗菌药物的两步流动酰胺化研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-05-23 Epub Date: 2025-03-31 DOI: 10.1021/acs.jnatprod.5c00131

Desirée Pecora, Anna M Magni, Sara Vicinanza, Francesca Annunziata, Salvatore Princiotto, Silvia Donzella, Gabriele Meroni, Piera A Martino, Nicoletta Basilico, Silvia Parapini, Paola Conti, Chiara Borsari, Lucia Tamborini

{"title":"Two-Step Flow Amidation of Natural Phenolic Acids as Antiradical and Antimicrobial Agents.","authors":"Desirée Pecora, Anna M Magni, Sara Vicinanza, Francesca Annunziata, Salvatore Princiotto, Silvia Donzella, Gabriele Meroni, Piera A Martino, Nicoletta Basilico, Silvia Parapini, Paola Conti, Chiara Borsari, Lucia Tamborini","doi":"10.1021/acs.jnatprod.5c00131","DOIUrl":"10.1021/acs.jnatprod.5c00131","url":null,"abstract":"Natural hydroxycinnamic acid amides (HCAAs) and riparins offer significant health benefits. However, their extraction from natural sources is difficult, and traditional synthetic methods remain wasteful, raising the need for more efficient alternatives. In this work, a two-step chemo-enzymatic flow method for the efficient esterification and amidation of phenolic acids was developed and successfully applied to the synthesis of riparin derivatives and HCAAs. The flow Fischer esterification was optimized using vanillic acid as a model starting material and SiliaBond Tosic Acid (SCX-3) as an immobilized acid catalyst, achieving a quantitative yield in a short residence time. The following amidation step, catalyzed by immobilized Candida antarctica lipase B, was optimized in toluene, leading to the desired amides. The synthesized compounds were evaluated for their radical scavenging, antibacterial, and antileishmanial properties. Overall, this work disclosed a novel approach for the efficient synthesis of riparin derivatives and HCAAs with interesting biological properties.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"1153-1159"},"PeriodicalIF":3.3,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143750268","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 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