Journal of Natural Products 最新文献

{"title":"Editorial for the Special Issue in Honor of Sheo Singh.","authors":"Gerald Bills, Gordon M Cragg, Olga Genilloud, David J Newman, Gino M Salituro","doi":"10.1021/acs.jnatprod.4c01403","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01403","url":null,"abstract":"","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"1-2"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027460","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}

{"title":"Semisynthesis of Nocarterphenyl A and Its Analogues.","authors":"Yong Wang, Yanchao Xu, Dan Wu, Dongyang Wang, Peng Fu, Weiming Zhu, Liping Wang","doi":"10.1021/acs.jnatprod.4c01198","DOIUrl":"10.1021/acs.jnatprod.4c01198","url":null,"abstract":"<p><p><i>p</i>-Terphenyl compounds are known to possess a diverse range of biological activities, making the synthesis of novel <i>p</i>-terphenyl derivatives a significant research objective. In this study, we report the first synthesis of nocarterphenyl A (<b>1</b>), characterized by a thiazole-fused <i>p</i>-terphenyl framework. Furthermore, we synthesized 18 additional analogs, including the naturally occurring compound 5-methoxy-4,7-bis(4-methoxyphenyl)benzo[<i>d</i>]thiazol-6-ol (<b>9</b>), employing a similar synthetic approach. Notably, compounds <b>12</b>, <b>13</b>, <b>15</b>-<b>17</b>, and <b>19</b> demonstrated potent inhibitory effects against protein tyrosine phosphatase 1B (PTP1B), exhibiting IC₅₀ values ranging from 2.2 to 7.9 μM, which are lower than that of oleanolic acid (13.2 μM). Additionally, compound <b>14</b> was found to inhibit α-glucosidase from human colorectal adenocarcinoma (Caco-2) cells with an IC₅₀ value of 10.4 μM, which is also lower than that of acarbose (11.2 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"133-140"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142890682","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}

{"title":"Pyridoxal 5'-Phosphate (PLP)-Dependent β- and γ-Substitution Reactions Forming Nonproteinogenic Amino Acids in Natural Product Biosynthesis.","authors":"Taku Mizutani, Ikuro Abe","doi":"10.1021/acs.jnatprod.4c01226","DOIUrl":"10.1021/acs.jnatprod.4c01226","url":null,"abstract":"<p><p>Living organisms synthesize various nonproteinogenic amino acids (NPAAs) as the building blocks of natural products. These NPAAs are often biosynthesized by pyridoxal 5'-phosphate (PLP)-dependent enzymes, which catalyze β- or γ- substitutions. These enzymes contribute to the structural diversification of NPAAs by installing new functional groups to amino acid side chains. Recent developments in genome mining have led to the identification of various PLP-dependent enzymes catalyzing β- or γ- substitutions, which form NPAAs in secondary metabolism. This short review summarizes recently investigated PLP-enzymes catalyzing β- or γ-substitutions in the biosynthesis of NPAAs by covering the literature published from 2015 through 2024.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"211-230"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142862529","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}

{"title":"Preparation, Modification, Quantitation, and Dentin Biomodification Activity of Selectively Enriched Proanthocyanidins.","authors":"Shu-Xi Jing, José Guilherme Neves, Walleska Liberato, Daneel Ferreira, Ana K Bedran-Russo, James B McAlpine, Shao-Nong Chen, Guido F Pauli","doi":"10.1021/acs.jnatprod.4c01213","DOIUrl":"10.1021/acs.jnatprod.4c01213","url":null,"abstract":"<p><p>To date, quantitative analysis of proanthocyanidin (PAC) containing materials including plant extracts and fractions depends on colorimetric assays or phloroglucinolysis/thiolysis combined with UV-HPLC analysis. Such assays are of limited accuracy, particularly lack specificity, require extensive sample preparation and degradation, and need appropriate physical reference standards. To address this analytical challenge and toward our broader goal of developing new plant-sourced biomaterials that chemically and mechanically modulate the properties of dental tissue for clinical interventions, we have characterized 12 different PAC DESIGNER (Depletion and Enrichment of Select Ingredients Generating Normalized Extract Resources) materials. The DESIGNER approach is carried out by using either centrifugal partition chromatography (CPC) or size-exclusion chromatography (SEC) for the selective enrichment of trimeric and tetrameric PACs. Moreover, the rare but biologically interesting A-type PAC DESIGNERs can now be generated successfully from their natural AB-type PAC precursors via phenol-oxidative intramolecular coupling initiated by a mixture of the stable radicals, 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). Furthermore, to ensure the quality and stability of PAC DESIGNER materials, we developed a quantitative analysis of the total PAC content of the DESIGNER materials in the form of a quantitative NMR (qNMR) method using a non-PAC internal calibrant combined with diol-HPLC. The total PAC content was, thus, determined to be in a range of 67.5-96.9% by qNMR. We highlight the complementarity of diol-HPLC and qNMR to accurately assess the amount of PACs across a range of concentrations and PAC stability in the DESIGNER materials. This quantitative methodology paves the way to generate standardized DESIGNER and other PAC-containing materials and to perform rigorous quality control for dental (pre)clinical studies of PACs.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"152-161"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142976735","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}

{"title":"Retraction of \"Direct Identification of α-Bisabolol Enantiomers in an Essential Oil Using a Combined Ion Mobility-Mass Spectrometry/Quantum Chemistry Approach\".","authors":"Erik Laurini, Stéphane Andreani, Alain Muselli, Sabrina Pricl, Aura Tintaru","doi":"10.1021/acs.jnatprod.4c01444","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c01444","url":null,"abstract":"","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 1","pages":"231"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027466","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}

{"title":"Natural and Semisynthetic Immunomodulatory Luakuliide Labdane Diterpenoids.","authors":"Jennie L Ramirez-Garcia, Elysha-Rose K Grant, Antonio Salamat, Mathew D Anker, Scott A Cameron, Michelle Kelly, S Vailala Matoto, Jacqueline M Barber, Peter T Northcote, Jenni W Williams-Spence, Anne C La Flamme, Joanne E Harvey, A Jonathan Singh, Robert A Keyzers","doi":"10.1021/acs.jnatprod.4c01218","DOIUrl":"10.1021/acs.jnatprod.4c01218","url":null,"abstract":"<p><p>Spectroscopy-guided isolation of extracts of the Tongan marine sponge <i>Hyattella</i> cf. <i>intestinalis</i> (Lamarck, 1814) has resulted in the reisolation of the labdane diterpenoid luakuliide A (<b>1</b>) and one new congener, luakulialactam A (<b>2</b>). In addition to establishing the absolute configuration of <b>1</b>, synthetic modifications to the luakuliide framework at key positions has created a set of six derivatives (<b>3</b>-<b>8</b>) which were used to interrogate a structure-activity relationship relating to the immunomodulatory effects of luakuliide A. This revealed that compounds <b>4</b>, <b>5</b>, and <b>6</b>, bearing substituted furan motifs, show potent activity in primary macrophages by inhibiting pro-inflammatory cytokine production, while upregulating cellular metabolism and anti-inflammatory IL-10 production at nanomolar concentrations. This is an activity profile consistent with macrophages modulated toward an anti-inflammatory phenotype associated with wound-healing and resolution of inflammation.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"162-174"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142880692","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}

{"title":"Macrocyclic Compounds with Diverse Skeletons from the Roots of <i>Myrica nana</i> and Their Spasmolytic Activity.","authors":"Liyuan Zhang, Ziliang Wang, Yuxiao Li, Shenghai Yang, Wenting Chen, Yanhong Li, Kai Tian, Yan Yuan, Xishan Bai, Xiangzhong Huang","doi":"10.1021/acs.jnatprod.4c01209","DOIUrl":"10.1021/acs.jnatprod.4c01209","url":null,"abstract":"<p><p>Six undescribed macrocyclic compounds, including diarylhexanoids (<b>1</b> and <b>2</b>), a diarylhexanoid glucoside (<b>3</b>), diarylheptanoids (<b>4</b> and <b>5</b>), and an aceroside (<b>6</b>), were isolated from the roots of <i>Myrica nana</i> Cheval., along with 11 known analogues (<b>7</b>-<b>17</b>). The structures were elucidated by spectroscopic analysis, as well as by calculated optical rotatory dispersion and derivatization reactions. Metabolites <b>1</b>-<b>3</b>, with a rare macrocyclic diarylhexane skeleton, differ from the familiar macrocyclic diarylheptanoids. The spasmolytic activity of the isolated compounds was evaluated on acetylcholine-induced contraction of isolated rat ileum. All isolated compounds exhibited significant spasmolytic activities with an EC₅₀ ranging from 1.4 to 5.1 μM. The spasmolytic mechanism of action of compound <b>1</b> could be related to the NO production, blockade of muscarinic receptors, K⁺ efflux, and cytosolic calcium reduction.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"141-151"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142890681","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}

{"title":"Cardenolides in <i>Asclepias syriaca</i> Seeds: Exploring the Legacy of Tadeus Reichstein.","authors":"Paola Rubiano-Buitrago, Ronald A White, Amy P Hastings, Frank C Schroeder, Anurag A Agrawal, Christophe Duplais","doi":"10.1021/acs.jnatprod.4c00960","DOIUrl":"10.1021/acs.jnatprod.4c00960","url":null,"abstract":"<p><p>The common milkweed <i>Asclepias syriaca</i> is widespread in North America and produces cardenolide toxins that deter herbivores by targeting the transmembrane enzyme Na⁺/K⁺-ATPase. In 1979, Nobel Laureate Tadeus Reichstein elucidated the structure of novel cardenolides isolated from <i>A. syriaca</i> roots and proposed structures for several other cardenolides that could not be confirmed. In this study, we investigate the cardenolide composition of <i>A. syriaca</i> seeds, focusing on their abundance and <i>in vitro</i> inhibitory potency on the sensitive porcine Na⁺/K⁺-ATPase and that of the highly resistant large milkweed bug, <i>Oncopeltus fasciatus</i>. We identify five previously unreported cardenolides (<b>1</b>-<b>5</b>), three of which are predominantly found in seeds, in addition to the known syrioside (<b>6</b>), aspecioside (<b>7</b>), and the 2-thiazoline ring-containing cardenolide labriformin (<b>8</b>). Glucopyranosyl-allomethylosyl-12-deoxy aspecioside (<b>5</b>) is distinguished by lack of oxidation at C-12, and compounds <b>2</b>, <b>3</b>, <b>6</b>, and <b>8</b> contain a rare 1,4-dioxane motif. Inhibitory efficacy of the isolated cardenolides for sensitive and resistant enzymes appears to be correlated. Finally, we confirmed the structure of compound <b>2</b>, originally proposed by Tadeus Reichstein, and are pleased to share his original 1979 handwritten manuscript.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"49-57"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142845311","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}

{"title":"Cyclopenta[<i>bc</i>]benzopyran Derivatives and Limonoids from <i>Aglaia edulis</i> with Cytotoxic and Anti-DENV Activity.","authors":"Ping Yi, Jian-Fei Qiu, Xiao-Meng Yang, Fei-Fei Chen, Jue Yang, Juan Liu, Jun Jin, Lian-Xin Qi, Xiao-Jiang Hao, Jia-Hong Wu, Chun-Mao Yuan","doi":"10.1021/acs.jnatprod.4c01194","DOIUrl":"10.1021/acs.jnatprod.4c01194","url":null,"abstract":"<p><p>Eighteen cyclopenta[<i>b</i>]benzopyran derivatives (<b>1</b>-<b>5</b> and <b>11</b>-<b>23</b>) and 10 limonoids (<b>6</b>-<b>10</b> and <b>24</b>-<b>28</b>) were identified from <i>Aglaia edulis</i>, including 10 undescribed compounds (<b>1</b>-<b>10</b>), all of which were identified by analysis of spectroscopic data, electronic circular dichroism calculations, and X-ray crystallography studies. Nine compounds displayed significant cytotoxic activity against three cancer cells, with IC₅₀ values of 3-900 nM. Sixteen compounds demonstrated potent antiviral activity on the dengue virus, with selectivity index values between 13.0 and 532.6. A mechanism of action investigation revealed that compound <b>11</b> may function as an eIF4E activator, which could suppress the expression of the E protein, thereby conferring significant activity against the dengue virus.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"119-132"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929901","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}

{"title":"Structural Similarity in Natural Products Leading to Sample Misidentification: A Case Study of the Bisbenzylisoquinoline Alkaloids Oxyacanthine and Berbamine.","authors":"Yan Cheng, Davlat Akramov, Lola Yakhshilikova, Chengwei Zhu, Jie Lu, Jin Suo, Santhosh Pugazh, Hongjian Qin, Safomuddin Abduahadi, Jishan Qin, Tianwen Hu, Jingshan Shen, Feipu Yang, Haji A Aisa","doi":"10.1021/acs.jnatprod.4c01109","DOIUrl":"10.1021/acs.jnatprod.4c01109","url":null,"abstract":"<p><p>The similar structures of natural compounds and the absence of NMR data for commercial products raise the risk of misidentification. This work reports a case in which purchased samples labeled as \"berbamine\" from 14 suppliers are oxyacanthine (<b>1</b>). The NMR data of all purchased samples were consistent. The X-ray crystallography characterization of one sample revealed it to be <b>1</b>. The NMR data of <b>1</b> were fully assigned for the first time. Berbamine (<b>2</b>) was isolated from the roots of <i>Berberis sieboldii</i> Miq. The NMR data of <b>2</b> were assigned, and its crystal structure was reported for the first time. The authors intend to raise awareness and support the academic/industrial community through a study of this misidentification case.</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"191-198"},"PeriodicalIF":3.3,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142941396","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}