Journal of Natural Products 最新文献_第5页

Phytotoxic Hemiketal-Containing Polyketides from the Endophytic Fungus Trichoderma koningiopsis WZ-196 with the OSMAC Strategy and Molecular Network Technology 利用OSMAC策略和分子网络技术从内生真菌koningiopsis WZ-196中提取植物毒性半块状多酮。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-11 DOI: 10.1021/acs.jnatprod.5c00616

Xin-Jing Li, Rui Zhang, Hao-Feng Huang, Xin-Nian Wang, Zhe Wang*, Li Feng* and Jia Wang*,

{"title":"Phytotoxic Hemiketal-Containing Polyketides from the Endophytic Fungus Trichoderma koningiopsis WZ-196 with the OSMAC Strategy and Molecular Network Technology","authors":"Xin-Jing Li, Rui Zhang, Hao-Feng Huang, Xin-Nian Wang, Zhe Wang*, Li Feng* and Jia Wang*, ","doi":"10.1021/acs.jnatprod.5c00616","DOIUrl":"10.1021/acs.jnatprod.5c00616","url":null,"abstract":"Thirty highly oxidized hemiketal-containing polyketides, including 10 new ones (1–10) and 20 known analogues (11–30), were obtained from the endophytic fungus Trichoderma koningiopsis WZ-196 with the OSMAC strategy in combination with molecular network analysis. Their structures were elucidated through comprehensive spectroscopic analysis, together with NMR and ECD calculations. The phytotoxic activities of all compounds were evaluated using Arabidopsis thaliana (dicotyledonous) and Oryza sativa (monocotyledonous) as model systems. The results showed that most compounds exhibited significant inhibitory effects on seedling growth. Notably, compound 9 demonstrated the strongest phytotoxic activity against A. thaliana with an IC50 value of 8.09 μM, while 24 markedly suppressed the growth of O. sativa with an IC50 value of 9.42 μM, outperforming the commercial herbicide glyphosate under identical experimental conditions. These findings highlight the potential of hemiketal-containing polyketides derived from endophytic fungi as promising candidates for developing novel bioherbicides.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"1936–1949"},"PeriodicalIF":3.6,"publicationDate":"2025-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144820148","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

Molecular Networking-Driven Discovery of an Unprecedented Cyclotetrapeptide and Potent Anti-MDR P-Glycoprotein Modulating Piperazines from Aspergillus templicola 由分子网络驱动的天门曲霉中前所未有的环四肽和有效的抗mdr p糖蛋白调节哌嗪的发现。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-07 DOI: 10.1021/acs.jnatprod.5c00766

Teng Cai, Nanjin Ding, Weiguang Sun, Jingzu Sun, Haohua Zhu, Qiang He, Baosong Chen, Peng Zhang, Hanli Ruan, Hongwei Liu, Yonghui Zhang* and Xiaofeng Cai*,

{"title":"Molecular Networking-Driven Discovery of an Unprecedented Cyclotetrapeptide and Potent Anti-MDR P-Glycoprotein Modulating Piperazines from Aspergillus templicola","authors":"Teng Cai, Nanjin Ding, Weiguang Sun, Jingzu Sun, Haohua Zhu, Qiang He, Baosong Chen, Peng Zhang, Hanli Ruan, Hongwei Liu, Yonghui Zhang* and Xiaofeng Cai*, ","doi":"10.1021/acs.jnatprod.5c00766","DOIUrl":"10.1021/acs.jnatprod.5c00766","url":null,"abstract":"Multidrug resistance (MDR) remains a significant challenge in cancer chemotherapy. Seeking novel MDR modulators, we employed a molecular networking (MN)-guided strategy to explore the endophytic fungus Aspergillus templicola. This led to the targeted isolation of an unprecedented cyclotetrapeptide, templicolamide A (1, featuring a rare β-enamino acid), and four piperazine derivatives (2–5), including the new helvamide E (2) with a unique bicyclic scaffold. The structures were elucidated through extensive spectroscopic analysis and comparison with literature data, with the absolute configuration of compound 1 further confirmed by advanced Marfey’s method and ECD calculations and that of compound 2 confirmed by single-crystal X-ray diffraction. All isolates were evaluated for their antipaclitaxel (PTX) resistance activity in P-glycoprotein (P-gp)-overexpressing tumor cell lines. Notably, the piperazine derivatives, particularly compound 3 (a known structure), exhibited potent MDR reversal. Mechanistic studies demonstrated that 3 reversed MDR primarily through direct binding to P-gp and inhibiting its efflux function, without affecting its expression. In vivo, the PTX + 3 combination achieved effective tumor regression and apoptosis in a xenograft model with no observable toxicity. Our findings broaden the structural diversity of fungal MDR modulators and underscore the potential of specific nontoxic piperazine scaffolds as promising anti-MDR therapeutic leads.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"2008–2017"},"PeriodicalIF":3.6,"publicationDate":"2025-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144797645","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

Integrating MassQL and Molecular Networking to Identify Bioactive Compounds in Idesia polycarpa Maxim. 利用MassQL和分子网络技术鉴定山梨的生物活性成分。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-05 DOI: 10.1021/acs.jnatprod.5c00551

Bo-Yeong Yu, Kyu Hyeong Lee, Myeong Ji Kim, Jingxuan Wen, Young-Sam Keum, Hyunwoo Kim

{"title":"Integrating MassQL and Molecular Networking to Identify Bioactive Compounds in Idesia polycarpa Maxim.","authors":"Bo-Yeong Yu, Kyu Hyeong Lee, Myeong Ji Kim, Jingxuan Wen, Young-Sam Keum, Hyunwoo Kim","doi":"10.1021/acs.jnatprod.5c00551","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00551","url":null,"abstract":"Idesia polycarpa Maxim (Salicaceae) is a well-studied plant producing various hydroxycyclohexenone (HCH) ester derivatives, which constitute most of its secondary metabolites. However, these major metabolites have been reported as unrelated to the alpha-melanocyte stimulating hormone (α-MSH) induced microphthalmia-associated transcription factor (MITF) expression observed in B16F10 melanoma cells, suggesting they may not be responsible for the antimelanogenic effect previously seen with the crude extract. To resolve this discrepancy and identify the bioactive metabolites in the crude extracts, the chemical diversity of I. polycarpa was reanalyzed using Mass Spec Query Language (MassQL)-enhanced molecular networking analysis, which indicated the presence of molecular families of phenolic glycosides without HCH esters. Following the MassQL-guided strategy to uncover the compounds responsible for the bioactivity, a targeted isolation study yielded five previously undescribed compounds and three known compounds, consistent with the MassQL annotations. Notably, one of the isolated non-HCH ester compounds, compound 1, demonstrated significant inhibition of α-MSH-induced melanogenesis via tyrosinase inhibition and MITF downregulation. This finding provides a potential explanation for the previously observed antimelanogenic activity of the crude extract, addressing the inconsistency associated with the major metabolites.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144783017","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

Alteration in Amino Acid Composition and Configuration in Cyanobacterial Peptides Affects Biological Activity 蓝藻多肽氨基酸组成和结构的改变影响生物活性。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-03 DOI: 10.1021/acs.jnatprod.5c00619

Runjie Xia, Hannuo Xie, Allyson M. Solorzano Mahmud and Matthew J. Bertin*,

{"title":"Alteration in Amino Acid Composition and Configuration in Cyanobacterial Peptides Affects Biological Activity","authors":"Runjie Xia, Hannuo Xie, Allyson M. Solorzano Mahmud and Matthew J. Bertin*, ","doi":"10.1021/acs.jnatprod.5c00619","DOIUrl":"10.1021/acs.jnatprod.5c00619","url":null,"abstract":"Cyanobacterial blooms are a significant environmental concern due to their production of toxic metabolites with potential impacts on ecosystem and human health. Microcystin-LR and microcystin congeners are a major concern with respect to human exposure and intoxication, but there are hundreds of characterized cyanobacterial peptides and metabolites that are of interest for their environmental impact in a variety of classes such as cyanopeptolins/micropeptins, microviridins, microginins, and anabaenopeptins. In this study, we report the isolation and characterization of new micropeptins (1–4), a new ferintoic acid (5) a new microginin (6), and three new microviridins (7–9) from a cyanobacterial bloom sample. The new micropeptins, in particular, exhibited unprecedented modifications in their amino acid composition and configuration, which differentiate them from previously known variants. Certain alterations significantly influenced their biological activity with respect to chymotrypsin inhibition and human neutrophil elastase inhibition, highlighting the potential ecological and biomedical relevance of these compounds. We report d-amino acid incorporation into the micropeptins for the first time providing new insights into the chemical diversity of cyanobacterial natural products. These results have important implications for understanding biosynthetic flexibility, the development of bioactive agents for therapeutic applications, and highlight the need for reference materials for mass spectrometry-based metabolite annotation.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"1950–1957"},"PeriodicalIF":3.6,"publicationDate":"2025-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144768149","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

A New Era for the Journal of Natural Products 天然产物杂志的新时代。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-01 DOI: 10.1021/acs.jnatprod.5c00935

Bradley S. Moore*,

引用次数: 0

Surface Plasmon Resonance Guided Identification of Quinolone Alkaloids from the Fruits of Tetradium ruticarpum as FSP1 Inhibitors 表面等离激元共振引导下鉴定龙柏果实中喹诺酮类生物碱为FSP1抑制剂。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-08-01 DOI: 10.1021/acs.jnatprod.5c00595

Qi-Mei Tan, Mu Li, Jiang-Min Zhu, Bill Zhereng Liao, Ling-Yi Kong* and Jian-Guang Luo*,

{"title":"Surface Plasmon Resonance Guided Identification of Quinolone Alkaloids from the Fruits of Tetradium ruticarpum as FSP1 Inhibitors","authors":"Qi-Mei Tan, Mu Li, Jiang-Min Zhu, Bill Zhereng Liao, Ling-Yi Kong* and Jian-Guang Luo*, ","doi":"10.1021/acs.jnatprod.5c00595","DOIUrl":"10.1021/acs.jnatprod.5c00595","url":null,"abstract":"Ferroptosis suppressor protein 1 (FSP1), a key regulator of ferroptosis that functions independently of glutathione, has become a vital therapeutic target in ferroptosis research. However, the discovery of FSP1 inhibitors remains a significant challenge, particularly given the absence of natural FSP1 inhibitors. In this study, surface plasmon resonance (SPR)-guided fractionation of the fruit extract of Tetradium ruticarpum (FTR) led to the isolation of 12 quinolone alkaloids, including ten known compounds (1–10) and two new ones (11 and 12). Compounds 1–9 all inhibited FSP1, among which 2–4 were the most potent (IC50 = 0.47 ± 0.12, 0.29 ± 0.17, and 0.52 ± 0.98 μM, respectively), exceeding the positive control icFSP by more than 50-fold. This study represents the first identification of natural FSP1 inhibitors. Our findings highlight the potential of quinolone alkaloids as novel agents targeting FSP1 and underscore the importance of exploring natural products for the development of new ferroptosis modulators.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"1919–1927"},"PeriodicalIF":3.6,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144764200","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

Total Synthesis and Antimicrobial Evaluation of Bisoflavolin D: A Novel Biflavonoid from Streptomyces sp. 链霉菌中新型类黄酮生物黄素D的合成及抗菌性能评价

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-07-30 DOI: 10.1021/acs.jnatprod.5c00720

Na Wang, Zhengwen Li, Hefei Shi, Mengqi Wang, Yufei Che, Fei Tan, Chunran Zhang and Hongbo Dong*,

引用次数: 0

Discovery of Spiroketal Acids and Antarmycin Analogues from Deep-Sea Derived Pseudonocardia antarctica and Its ΔantB3 Mutant Strain 深海南极伪心菌及其ΔantB3突变株中螺旋酮酸和抗霉素类似物的发现。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-07-29 DOI: 10.1021/acs.jnatprod.5c00639

Zhenbin Zhou, Zhuo Shang, Naying Gong, Jiafan Yang, Xiaohua Li, Hua Zhang, Xinpeng Tian, Junying Ma* and Jianhua Ju*,

{"title":"Discovery of Spiroketal Acids and Antarmycin Analogues from Deep-Sea Derived Pseudonocardia antarctica and Its ΔantB3 Mutant Strain","authors":"Zhenbin Zhou, Zhuo Shang, Naying Gong, Jiafan Yang, Xiaohua Li, Hua Zhang, Xinpeng Tian, Junying Ma* and Jianhua Ju*, ","doi":"10.1021/acs.jnatprod.5c00639","DOIUrl":"10.1021/acs.jnatprod.5c00639","url":null,"abstract":"This study reports the discovery of eight new polyketide natural products from the deep-sea actinomycete Pseudonocardia antarctica SCSIO 07407 and its ΔantB3 mutant strain. Through OSMAC (One Strain Many Compounds)-based fermentation, six new spiroketal acid derivatives, namely, semiantarmycins B–G (1–6) and a spiroketal-polyketoester hybrid (7), were isolated from the wild-type strain. In parallel, a new antarmycin analogue, namely, antarmycin D (8), was obtained from the ΔantB3 mutant strain, in which the glycosyl 2,3-dehydratase encoding gene was disrupted. Structure elucidation using HR-ESIMS, 1D/2D NMR, and biosynthetic analysis revealed 1–3 feature a C-11 epimerized spiroketal core glycosylated with vancosamine or glucose, whereas 6 and 5 exhibit sequential dehydration and reduction at C-12/C-13. Compound 7 is the first reported spiroketal-polyketoester hybrid, and macrodiolide 8 incorporates rhamnose glycosylation along with C-11 methylation. Bioactivity screening revealed that 8 exhibits cytotoxicity against five cancer cell lines, including HCT116, SW480, MCF7, MDA-MB-468, and BT-549 with IC50 values ranging from 2.02 to 7.65 μM. This work expands the chemical diversity of spiroketal acids and macrodiolides, highlighting deep-sea actinomycetes as an underexplored source of structurally unique and biologically active natural products.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"1970–1979"},"PeriodicalIF":3.6,"publicationDate":"2025-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144726006","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

Value Addition to African Natural Product-Based Drug Discovery Initiatives 非洲基于天然产品的药物发现计划的增值。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-07-29 DOI: 10.1021/acs.jnatprod.5c00446

Godfrey Mayoka*, Peter Mubanga Cheuka, Phanankosi Moyo, Godwin Akpeko Dziwornu and Denzil Beukes,

引用次数: 0

Discovery of Structurally Diverse γ-Pyrone-Type Diterpenoids Produced by the Fungus Mariannaea sp. FKR-1011 from Zamami Island Zamami岛Mariannaea sp. FKR-1011产γ- pyroone型二萜结构多样性的发现。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-07-29 DOI: 10.1021/acs.jnatprod.5c00223

Kazuki Tani, Miyu Wakatsuki, Masahiro Wada, Kenichi Nonaka, Yuta Kikuchi, So-ichiro Kimura, Yoshihiro Watanabe, Rei Hokari, Tomoyasu Hirose, Masako Honsho, Yukihiro Asami, Hayama Tsutsumi, Yuki Inahashi, Masato Iwatsuki, Hidehito Matsui, Toshiaki Sunazuka, Hideaki Hanaki, Toshiaki Teruya and Takahiro Ishii*,

{"title":"Discovery of Structurally Diverse γ-Pyrone-Type Diterpenoids Produced by the Fungus Mariannaea sp. FKR-1011 from Zamami Island","authors":"Kazuki Tani, Miyu Wakatsuki, Masahiro Wada, Kenichi Nonaka, Yuta Kikuchi, So-ichiro Kimura, Yoshihiro Watanabe, Rei Hokari, Tomoyasu Hirose, Masako Honsho, Yukihiro Asami, Hayama Tsutsumi, Yuki Inahashi, Masato Iwatsuki, Hidehito Matsui, Toshiaki Sunazuka, Hideaki Hanaki, Toshiaki Teruya and Takahiro Ishii*, ","doi":"10.1021/acs.jnatprod.5c00223","DOIUrl":"10.1021/acs.jnatprod.5c00223","url":null,"abstract":"Seven γ-pyrone-type diterpenoids, including four new compounds (candelalides D–G (1–4)) and three known compounds (candelalides A–C (5–7)), were isolated from the solid culture material of the fungus Mariannaea sp. strain FKR-1011, obtained from Zamami Island, Okinawa, Japan. The chemical structures and relative configurations of 1–4 were determined by spectroscopic analysis such as FT-IR, NMR, and HR-ESI-MS. The absolute configurations of 1–4 were determined through extensive spectroscopic data analysis and TDDFT-ECD calculations. The isolated compounds were tested for biological activity, revealing antibacterial activity against methicillin-resistant Staphylococcus aureus in combination with β-lactam antibiotics and antimalarial activity against Plasmodium falciparum K1 and FCR3 strains.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 8","pages":"1871–1878"},"PeriodicalIF":3.6,"publicationDate":"2025-07-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144740659","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