Journal of Natural Products 最新文献_第2页

Phenolics and Phenolic Glycosides from Wrightia pubescens and Their Hepatoprotective Activities.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI: 10.1021/acs.jnatprod.4c01040

Xingxiang Chen, Ping Yi, Hang Lv, Mimi Zhang, Junwei Yang, Zengguang Zhang, Zhilong Zhao, Yu Mu, Li Han, Xueshi Huang

{"title":"Phenolics and Phenolic Glycosides from Wrightia pubescens and Their Hepatoprotective Activities.","authors":"Xingxiang Chen, Ping Yi, Hang Lv, Mimi Zhang, Junwei Yang, Zengguang Zhang, Zhilong Zhao, Yu Mu, Li Han, Xueshi Huang","doi":"10.1021/acs.jnatprod.4c01040","DOIUrl":"10.1021/acs.jnatprod.4c01040","url":null,"abstract":"Thirty compounds including 13 new phenolic glycosides (1-6, 9-15) and 17 known aromatic compounds and aromatic glycosides (7-8, 16-30) were isolated from the roots of Wrightia pubescens. The structures of the new phenolic glycosides were established by extensive NMR spectroscopic data analysis as well as chemical derivatization method. The isolated compounds were evaluated for their hepatoprotective activities using cell model of acetaminophen (APAP)-induced HepG2 cells. The results indicated that phenolic glycosides (2, 4, 5, 7, 8, 11, 13) pretreatment enhanced the cells viability and reduced the levels of aspartate aminotransferase (AST), alanine aminotransferase (ALT). The hepatoprotective mechanism of a representative new compound, wrightioside D (4), was further investigated. Compound 4 exhibited hepatoprotective effects via reducing oxidative stress by attenuating ROS formation and inhibiting apoptosis in APAP-treated HepG2 cells.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"631-643"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143514094","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

(±)-Feionemycin A and Chromonemycins A-D, Rearranged Aromatic Polyketides Uncovered by Type II Polyketide Gene Cluster Expression.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI: 10.1021/acs.jnatprod.4c01433

Xiaofei Huang, Xiao Xu, Luning Zhou, Jiayi Li, Chuanteng Ma, Wenxue Wang, Qian Che, Dehai Li, Tianjiao Zhu, Guojian Zhang

引用次数: 0

Total Syntheses, Absolute Configuration, and Cytotoxicity Evaluation of Ugonins L, S, U, and Z from the Rhizomes of Helminthostachys zeylanica.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-13 DOI: 10.1021/acs.jnatprod.4c01487

Cheng-Tin Lin, Jing-Jy Cheng, Huei-Ling You, Cheng-Hsun Hsieh, Chiao-Jou Pan, Ming-Jaw Don

引用次数: 0

Chromene Dimers from Cultures of Basidiomycete Panus similis.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-26 DOI: 10.1021/acs.jnatprod.4c01475

Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka

{"title":"Chromene Dimers from Cultures of Basidiomycete Panus similis.","authors":"Somporn Palasarn, Prattana Tanyapanyachon, Vanicha Vichai, Phongeun Sysouphanthong, Kevin D Hyde, Nattika Saengkrit, Masahiko Isaka","doi":"10.1021/acs.jnatprod.4c01475","DOIUrl":"10.1021/acs.jnatprod.4c01475","url":null,"abstract":"Four chromene dimers, panusimilins A-D (1-4) (racemic mixtures), and two previously undescribed chromanes (5a/5b and 6a/6b) were isolated from cultures of basidiomycete Panus similis TBRC-BCC 52578. Interestingly, synthetic compounds closely related to panusimilins A-C (1-3) were previously reported, which were produced by Lewis acid promoted dimerization of a plant-derived chromene, precocene II. In the present study, panusimilins were isolated from the culture broth extract of the fungus P. similis. The chromane monomers were shown to be a non-racemic mixture of enantiomers, and their absolute configurations were elucidated by conversion to Mosher ester derivatives. The isolated compounds were evaluated for their cytotoxic activities. Among them, 2,2-dimethyl-3,4,6-trihydroxychromane (6a/6b) showed selective activity to NCI-H187 cells (IC50 9.1 μM). On the other hand, panusimilin B (2) exhibited antioxidant activity in the DPPH radical scavenging assay (IC50 66 μM).","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"777-784"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143514074","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

Efficient and Selective Biosynthesis of a Precursor-Directed FK506 Analogue: Paving the Way for Click Chemistry.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-10 DOI: 10.1021/acs.jnatprod.4c00394

Dušan Goranovič, Branko Jenko, Barbara Ramšak, Ajda Podgoršek Berke, Leon Bedrač, Jaka Horvat, Martin Šala, Damjan Makuc, Guilhermina M Carriche, Luana Silva, Aleksandra Lopez Krol, Alen Pšeničnik, María Beatriz Durán Alonso, Martina Avbelj, Stojan Stavber, Janez Plavec, Tim Sparwasser, Rolf Müller, Gregor Kosec, Štefan Fujs, Hrvoje Petković

{"title":"Efficient and Selective Biosynthesis of a Precursor-Directed FK506 Analogue: Paving the Way for Click Chemistry.","authors":"Dušan Goranovič, Branko Jenko, Barbara Ramšak, Ajda Podgoršek Berke, Leon Bedrač, Jaka Horvat, Martin Šala, Damjan Makuc, Guilhermina M Carriche, Luana Silva, Aleksandra Lopez Krol, Alen Pšeničnik, María Beatriz Durán Alonso, Martina Avbelj, Stojan Stavber, Janez Plavec, Tim Sparwasser, Rolf Müller, Gregor Kosec, Štefan Fujs, Hrvoje Petković","doi":"10.1021/acs.jnatprod.4c00394","DOIUrl":"10.1021/acs.jnatprod.4c00394","url":null,"abstract":"The medically important immunosuppressant FK506 is a structurally complex macrolactone biosynthesized by a combined polyketide synthase and a nonribosomal peptide synthetase enzyme complex. Its acyltransferase domain 4 (AT4) selects an unusual extender unit, resulting in an allyl moiety on carbon 21 of the macrolactone backbone. Based on the AT4 domain, chemobiosynthetic processes have been developed that enable the introduction of diverse moieties at the carbon 21 position. However, the novel moieties that were introduced into the polyketide backbone are chemically inert. Reported here is a novel and efficient chemobiosynthetic approach that ensures high titer of an FK506 analogue containing a propargyl moiety. The novel FK506 analogue displays lower immunosuppression activity than FK506 with significantly reduced cytotoxicity. More importantly, the propargyl moiety contains a terminal alkyl group, which makes click chemistry reactions possible; this approach may potentially be translated to other medically important drugs of polyketide origin.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"619-630"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143583945","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

Characterization of an Iterative Halogenase Acting on Ribosomal Peptides Underlies the Combinatorial Biosynthesis Logic of Lasso Peptides.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-20 DOI: 10.1021/acs.jnatprod.4c01199

Jin-Long Lu, Jiao-Jiao Cui, Zhe-Yang Hu, Jin-Ming Di, Yuan-Yuan Li, Jiang Xiong, Yu-Meng Jiao, Kun Gao, Jian Min, Shangwen Luo, Shi-Hui Dong

{"title":"Characterization of an Iterative Halogenase Acting on Ribosomal Peptides Underlies the Combinatorial Biosynthesis Logic of Lasso Peptides.","authors":"Jin-Long Lu, Jiao-Jiao Cui, Zhe-Yang Hu, Jin-Ming Di, Yuan-Yuan Li, Jiang Xiong, Yu-Meng Jiao, Kun Gao, Jian Min, Shangwen Luo, Shi-Hui Dong","doi":"10.1021/acs.jnatprod.4c01199","DOIUrl":"10.1021/acs.jnatprod.4c01199","url":null,"abstract":"Halogenation is commonly utilized in medicinal chemistry for the improvement of drug leads. Flavin-dependent halogenases (FDHs) are ubiquitous across all domains of life, yet iterative FDHs are rare in the biosynthesis of ribosomally synthesized and post-translationally modified peptides (RiPPs). Herein, we characterize a novel iterative FDH, ChlH, which orchestrates nonsequential chlorination of two specific Trp within the core peptide of a lasso precursor containing three Trp. Biochemical and computational studies enable the characterization of ChlH, which employs unique protein-peptide interactions (PPIs) between its distinct N- and C-terminal motifs and a crucial recognition sequence (RS-II) downstream of RS-I in the leader peptide. Previous studies have demonstrated the indispensability of RS-I for lasso peptide biosynthesis, while RS-II was considered to be replaceable. Furthermore, we find that the core peptide substantially contributes to the PPI. Bioinformatic analysis reveals the prevalence of homologous FDHs in the biosynthetic gene clusters (BGCs) of various RiPP classes. Heterologous expression of the chl BGC yields non-, mono-, and dichlorinated lasso peptides, with chlorination, particularly dichlorination, enhancing their antibacterial activity. This study expands the FDH activity spectrum to include iterative catalysis on ribosomal peptides and underscores the significance of RS-II in tailoring enzymes for the combinatorial biosynthesis of lasso peptides.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"650-661"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143456244","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

Gymnopeptides C and D, Highly N-Methylated Fungal Cyclopeptides.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-27 DOI: 10.1021/acs.jnatprod.4c01132

Márton Weber, Miklós Dékány, Andrea Nedves Nagyné, Csenge Anna Felegyi-Tóth, Suratno Suratno, Balázs Krámos, Enikő Bodó, Zoltán Béni, Attila Ványolós

引用次数: 0

Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-04 DOI: 10.1021/acs.jnatprod.4c01247

Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe

{"title":"Additional Bioactive Silvestrol Analogs from the Roots of Aglaia perviridis Collected in Vietnam.","authors":"Ermias Mekuria Addo, Daniel Adu-Ampratwum, Elizabeth N Kaweesa, Garima Agarwal, Dmitriy Uchenik, Tran N Ninh, Djaja D Soejarto, Joanna E Burdette, James R Fuchs, A Douglas Kinghorn, Harinantenaina L Rakotondraibe","doi":"10.1021/acs.jnatprod.4c01247","DOIUrl":"10.1021/acs.jnatprod.4c01247","url":null,"abstract":"The tropical plant Aglaia perviridis is known to produce cyclopenta[b]benzofuran and other types of rocaglate derivatives including silvestrol (3) and 5‴-episilvestrol (4) that are of current pharmacological interest. In the present work, further investigation of A. perviridis roots collected in Vietnam has yielded two new rocaglate acetonide derivatives (1 and 2) and a known pentanor-3,4-seco-dammarane triterpenoid (7) found for the first time as a natural product, in addition to four known rocaglates (3-6). The structures of compounds 1 and 2 were confirmed by partial synthesis experiments, and their potential occurrence as extraction artifacts was investigated by targeted selective ion monitoring using UHPLC-MS. All compounds obtained were evaluated against a panel of four human cancer cell lines, in which the six rocaglate derivatives (1-6) tested all showed submicromolar potencies.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"662-670"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143555348","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

Palladium-Catalyzed Late-Stage Functionalization of Natural Antitumor Drug: Synthesis and Bioactivity of 5-Aryl Camptothecins.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-03-07 DOI: 10.1021/acs.jnatprod.4c01344

Lian Sun, Xiao-Long Li, Qiu-Shan Huang, Wan-Sheng Ji, Xiaohuan Li, Jin-Bu Xu, Feng Gao

{"title":"Palladium-Catalyzed Late-Stage Functionalization of Natural Antitumor Drug: Synthesis and Bioactivity of 5-Aryl Camptothecins.","authors":"Lian Sun, Xiao-Long Li, Qiu-Shan Huang, Wan-Sheng Ji, Xiaohuan Li, Jin-Bu Xu, Feng Gao","doi":"10.1021/acs.jnatprod.4c01344","DOIUrl":"10.1021/acs.jnatprod.4c01344","url":null,"abstract":"Camptothecin (CPT) and its derivatives have garnered significant interest due to their potent anticancer activity. In this study, 62 novel CPT derivatives (1a-31a and 1b-31b) were designed and synthesized through Pd-catalyzed late-stage modification at the C-5 position. The anticancer efficacy of these compounds against three human cancer cell lines was evaluated. Compounds 5R-12a (IC50 = 0.05 ± 0.01 μM against HCT-116) and 5R-6a (IC50 = 0.04 ± 0.03 μM against MCF-7) exhibited enhanced antitumor activity when compared to CPT. The preliminary mechanism of apoptosis was investigated through cell viability assays, protein expression, and docking analysis. The results indicated that compounds 12a and 6a exhibited a greater ability to induce apoptosis and G2/M phase arrest than did CPT. Docking results provided a possible explanation for the superior activity of the 5R configuration. This work would offer new insights for CPT lead compound development.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":"706-714"},"PeriodicalIF":3.3,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143575605","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

Ohauamines A-D, Structurally Unprecedented Tricyclic Depsi-tripeptides from the New Zealand Ascidian Pycnoclavella kottae.

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2025-03-28 Epub Date: 2025-02-20 DOI: 10.1021/acs.jnatprod.5c00033

Dan Chen, Florent Rouvier, Robert Keyzers, Marie-Lise Bourguet-Kondracki, Jean Michel Brunel, Melissa M Cadelis, Brent R Copp

引用次数: 0