Journal of Natural Products 最新文献_第2页

Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from Cannabis sativa L. 新型大麻素大麻二酚的化学合成、抗炎活性及提取[j]。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-25 DOI: 10.1021/acs.jnatprod.5c00826

Luca Pozzi, Andrea Gotti, Marco Fumagalli, Andrea Citarella, Valerio Fasano, Giuseppe Paladino, Umberto Ciriello, Salvatore Princiotto, Francesca Annunziata, Giulia Martinelli, Enrico Sangiovanni, Andrea Pinto, Mario Dell'Agli, Daniele Passarella

{"title":"Cannabizetol, a Novel Cannabinoid: Chemical Synthesis, Anti-inflammatory Activity and Extraction from Cannabis sativa L.","authors":"Luca Pozzi, Andrea Gotti, Marco Fumagalli, Andrea Citarella, Valerio Fasano, Giuseppe Paladino, Umberto Ciriello, Salvatore Princiotto, Francesca Annunziata, Giulia Martinelli, Enrico Sangiovanni, Andrea Pinto, Mario Dell'Agli, Daniele Passarella","doi":"10.1021/acs.jnatprod.5c00826","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00826","url":null,"abstract":"We report the first isolation of a previously unknown cannabinoid, cannabizetol (CBGD, 7), from Cannabis sativa extracts, representing the third member of the rare class of methylene-bridged dimeric cannabinoids. The availability of a chemically synthesized standard was crucial for its unequivocal identification, thus confirming the natural occurrence of this new compound. In addition to this structural discovery, we demonstrate that cannabizetol exhibits remarkable antioxidant and skin anti-inflammatory activity, significantly higher than that observed for the known dimeric cannabinoid cannabitwinol (CBDD, 6). These results highlight cannabizetol as a promising bioactive metabolite with potential dermatological applications. To further enable its study, we developed a continuous flow approach to optimize the preparation of these dimers, achieving a substantial reduction in reaction times.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-09-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145135914","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

Actinomycetoquinones A-E, Anthraquinone-γ-Pyrones Discovered from Marine-Derived Actinomycetospora sp. Bacterium. 从海洋源放线菌孢子菌中发现放线菌醌A-E、蒽醌γ- pyroones。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-25 DOI: 10.1021/acs.jnatprod.5c00578

Fan Zhang, Christopher D Roberts, Tae Hyun Lee, Doug R Braun, Zachary D Bennett, Shaurya Chanana, Song Guo, Gene E Ananiev, Ilia A Guzei, Scott R Rajski, Thomas C Brunold, Tim S Bugni

引用次数: 0

The Role of Nucleotide Sequencing in Natural Product Drug Discovery. 核苷酸测序在天然产物药物发现中的作用。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-25 DOI: 10.1021/acs.jnatprod.5c00876

Samantha C Waterworth

引用次数: 0

Discovery of Isonitrile Lipopeptide Chalkophores from Pathogenic Mycobacteria. 致病性分枝杆菌中异腈脂肽荧光团的发现。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-23 DOI: 10.1021/acs.jnatprod.5c00904

Kaimin Jia, Helen Sun, Quang Kim Huynh, Dunya Al Marzooqi, Yongle Du, Yiyan Zhou, Wenjun Zhang

{"title":"Discovery of Isonitrile Lipopeptide Chalkophores from Pathogenic Mycobacteria.","authors":"Kaimin Jia, Helen Sun, Quang Kim Huynh, Dunya Al Marzooqi, Yongle Du, Yiyan Zhou, Wenjun Zhang","doi":"10.1021/acs.jnatprod.5c00904","DOIUrl":"10.1021/acs.jnatprod.5c00904","url":null,"abstract":"The virulence-associated isonitrile lipopeptide (INLP) biosynthetic gene cluster is conserved across Mycobacterium tuberculosis and many nontuberculous mycobacteria (NTM) pathogens, yet the corresponding mycobacterial metabolites have not been fully characterized, and their biological functions are still debated. Here, we report a precursor neutral loss chromatography based mass spectrometry strategy that enables the targeted discovery of INLPs from Mycobacterium fortuitum, a fast-growing NTM pathogen. By monitoring a characteristic neutral loss of 27.1 Da corresponding to hydrogen cyanide, we identified a family of INLPs directly from bacterial culture extracts. Structural elucidation of a representative compound using NMR and high-resolution MS revealed a distinctive terminal methylated carboxyl group, contrasting with previously reported INLPs bearing linear alcohol, acetal, or cyclic motifs. Bioinformatic analysis and in vitro enzymatic assays identified a methyltransferase encoded within the INLP BGC responsible for methyl ester formation. Furthermore, metal-binding assays demonstrated selective chelation of Cu(I) and Cu(II) by the isolated INLP, but no detectable interaction with Zn(II), suggesting a role in copper homeostasis. These findings represent the first full structural characterization of an INLP from pathogenic mycobacteria, expand our understanding of the enzymes involved in INLP modification, and unequivocally support the copper-binding activity of INLPs from these pathogens.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-09-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC12462896/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145129564","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

引用次数: 0

Targeted and Untargeted Mass Spectrometry Do Not Detect Grayanane-Type Toxins in Monotropa uniflora L. 靶向质谱法和非靶向质谱法均不能检测到单叶草中格雷烷型毒素。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-22 DOI: 10.1021/acs.jnatprod.5c00805

Savannah G Anez, Daghan B Flail, Eric P Burkhart, Joshua J Kellogg

引用次数: 0

Threonyl-tRNA Synthetase Is the Target of Borrelidin Insecticidal Activity against Silkworms. Borrelidin对家蚕杀虫活性的作用靶点：苏酰trna合成酶。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-22 DOI: 10.1021/acs.jnatprod.5c00737

Aoi Kimishima, Yukihiro Asami, Naozumi Kondo, Sota Negami, Sota Honma, Yukiko Ujie

引用次数: 0

Cytotoxic Triterpene Glycosides from Mexican Sea Cucumber Holothuria inornata. 墨西哥海参的细胞毒性三萜苷。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-21 DOI: 10.1021/acs.jnatprod.5c00716

Esteban López-Sampedro, Roberto Arreguin-Espinosa, Ana M Simonet

{"title":"Cytotoxic Triterpene Glycosides from Mexican Sea Cucumber Holothuria inornata.","authors":"Esteban López-Sampedro, Roberto Arreguin-Espinosa, Ana M Simonet","doi":"10.1021/acs.jnatprod.5c00716","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.5c00716","url":null,"abstract":"Sea cucumbers (Holothuriidae) are highly valued in traditional medicine and are recognized for their diverse bioactivities, which are largely attributed to their rich triterpene glycoside content. Given that Holothuria inornata was chemically uncharacterized, this study describes the bioassay-guided isolation of these compounds. Nine sulfated saponins were purified, and their structures were elucidated using UPLC-QTOF/HR-ESI-MSn and comprehensive NMR spectroscopy. Six new compounds were identified, including inornatosides A-C (1-3) and 22R-holothurin B (6), all possessing a holostane-type aglycone, alongside inornatosides D (4) and E (5), which feature unique aglycones. Cytotoxic assays revealed that inornatoside B (2) exhibited potent cytotoxic activity against human mammary adenocarcinoma (MCF-7) and human lung adenocarcinoma (SKLU-1) cell lines, with IC50 values between 0.47 and 0.50 μM surpassing the efficacy of the positive control. These findings not only expand the chemical diversity of holothurins but also position H. inornata as a promising source of anticancer compounds.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":" ","pages":""},"PeriodicalIF":3.6,"publicationDate":"2025-09-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145111587","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

Design, Synthesis, and Antibacterial Activity of Long-Chain Alkyl-Substituted DemethyloxyAaptamine Derivatives 长链烷基取代去甲基氧胺衍生物的设计、合成及抗菌活性研究。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-18 DOI: 10.1021/acs.jnatprod.5c00571

Yingqiu Liu, , , Wei Wu, , , Haitao Xue, , , Shu-Ping Wang, , , Jing Xu, , , Tao Zhang*, , , Hou-Wen Lin*, , and , Hongze Liao*,

{"title":"Design, Synthesis, and Antibacterial Activity of Long-Chain Alkyl-Substituted DemethyloxyAaptamine Derivatives","authors":"Yingqiu Liu, , , Wei Wu, , , Haitao Xue, , , Shu-Ping Wang, , , Jing Xu, , , Tao Zhang*, , , Hou-Wen Lin*, , and , Hongze Liao*, ","doi":"10.1021/acs.jnatprod.5c00571","DOIUrl":"10.1021/acs.jnatprod.5c00571","url":null,"abstract":"Demethyloxyaaptamine, isolated from the marine sponge Aaptos aaptos, features a 1H-benzo[de][1,6]naphthyridine core and exhibits potent antibacterial activity. To systematically investigate its underexplored antibacterial properties and facilitate structural optimization, we constructed a focused library of 28 C-3 alkylamino–substituted derivatives of demethyloxyaaptamine via regioselective functionalization. In vitro evaluation against Staphylococcus aureus revealed that several derivatives possess minimum inhibitory concentrations (MICs) superior to vancomycin. Structure–activity relationship analysis (SAR) demonstrated that the incorporation of moderately hydrophobic alkylamino groups at the C-3 position markedly improved antimicrobial efficacy. Mechanistic investigations demonstrated that these compounds inhibit bacterial growth by targeting bacterial membrane. Together, these findings validate demethyloxyaaptamine as a privileged scaffold for targeting drug-resistant Gram-positive pathogens and deliver critical SAR insights to guide the design of next-generation antibiotics.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2097–2106"},"PeriodicalIF":3.6,"publicationDate":"2025-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145079078","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

Ulleungpeptins A and B: Antiangiogenic Lipohexapeptides Containing E/Z-Decadienoic Acid Moieties from Streptomyces sp. 13F051 ulleungpeptin A和B：来自链霉菌sp. 13F051的含有E/ z -十二烯酸片段的抗血管生成脂六肽。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-15 DOI: 10.1021/acs.jnatprod.5c00880

Gwi Ja Hwang, , , Jongtae Roh, , , Kyung Taek Heo, , , Byeongsan Lee, , , Sangkeun Son, , , Young-Sam Kim, , , Jun-Pil Jang, , , Sung-Kyun Ko*, , , Young-Soo Hong*, , and , Jae-Hyuk Jang*,

引用次数: 0

Chlorinated Guaiane-Type Sesquiterpene Lactones of Natural Origin 天然来源的氯代愈创烷型倍半萜内酯。

IF 3.6 2区生物学

Journal of Natural Products Pub Date : 2025-09-12 DOI: 10.1021/acs.jnatprod.5c00844

Xinge Huang, , , Hongliang Li, , , Hui Lu, , , Haji Akber Aisa*, , and , Jun Li*,

{"title":"Chlorinated Guaiane-Type Sesquiterpene Lactones of Natural Origin","authors":"Xinge Huang, , , Hongliang Li, , , Hui Lu, , , Haji Akber Aisa*, , and , Jun Li*, ","doi":"10.1021/acs.jnatprod.5c00844","DOIUrl":"10.1021/acs.jnatprod.5c00844","url":null,"abstract":"Organohalogen natural products play a crucial role in drug research, with halogenation generally enhancing the bioactivity of natural compounds. Chlorinated natural compounds, a major category of organohalogens, are found in both marine and terrestrial environments. Among these, terpenoids are abundant compounds with diverse structures. Guaiane-type sesquiterpene lactones, with a [5,7,5] tricyclic skeleton, are one such class. Since the first examples in 1968, 102 natural chlorinated guaiane-type sesquiterpene lactones has been isolated from Asteraceae family plants. These compounds exhibit significant structural diversity, with chlorine located at various positions, including C-1, C-2, C-3, C-4, C-5 in the cyclopentyl, and C-13, C-14, C-15, and C-18 at the C-8 substituent. Determining the structure of these compounds, especially regarding chlorine position and stereochemistry, is challenging, with some structures revised using chemical computational techniques. Although few studies have examined their bioactivity, these compounds exhibit various bioactivities, including cytotoxic, anti-inflammatory, melanogenesis and tyrosinase stimulation, antimicrobial, antiviral, neuroprotective, inhibition effects on butyrylcholinesterase and acetylcholinesterase, and hematopoietic stem cell expansion activities. This review summarizes the natural origin, structural and NMR characteristics, and bioactivities of these rare compounds, offering an overview of their current research status, future pharmaceutical potential, and highlighting existing gaps and further directions.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":"88 9","pages":"2279–2300"},"PeriodicalIF":3.6,"publicationDate":"2025-09-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145051407","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