Journal of Natural Products 最新文献

Mass Spectrometry Imaging of Coniine and Other Hemlock Alkaloids after On-Tissue Derivatization Reveals Distinct Alkaloid Distributions in the Plant. 组织衍生化后的柯尼碱和其他铁杉生物碱质谱成像揭示了植物中不同的生物碱分布。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-06-21 DOI: 10.1021/acs.jnatprod.4c00445

Diana A Barrera-Adame, Sabine Schuster, Timo H J Niedermeyer

{"title":"Mass Spectrometry Imaging of Coniine and Other Hemlock Alkaloids after On-Tissue Derivatization Reveals Distinct Alkaloid Distributions in the Plant.","authors":"Diana A Barrera-Adame, Sabine Schuster, Timo H J Niedermeyer","doi":"10.1021/acs.jnatprod.4c00445","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00445","url":null,"abstract":"Specialized metabolites play important roles in plants and can, for example, protect plants from predators or pathogens. Alkaloids, due to their pronounced biological activity on higher animals, are one of the most intriguing groups of specialized metabolites, and many of them are known as plant defense compounds. Poison hemlock, Conium maculatum, is well-known for its high content of piperidine alkaloids, of which coniine is the most famous. The distribution, localization, and diversity of these compounds in C. maculatum tissues have not yet been studied in detail. The hemlock alkaloids are low molecular weight compounds with relatively high volatility. They are thus difficult to analyze on-tissue by MALDI mass spectrometry imaging due to delocalization, which occurs even when using an atmospheric pressure ion source. In this manuscript, we describe an on-tissue derivatization method that allows the subsequent determination of the spatial distribution of hemlock alkaloids in different plant tissues by mass spectrometry imaging. Coniferyl aldehyde was found to be a suitable reagent for derivatization of the secondary amine alkaloids. The imaging analysis revealed that even chemically closely related hemlock alkaloids are discretely distributed in different plant tissues. Additionally, we detected a yet undescribed hemlock alkaloid in Conium maculatum seeds.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-06-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141430891","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

First Bioprospecting Study of Skin Host-Defense Peptides in Odontophrynus americanus. 首次对美洲齿蟾的皮肤宿主防御肽进行生物勘探研究。

IF 3.3 2区生物学

Journal of Natural Products Pub Date : 2024-06-20 DOI: 10.1021/acs.jnatprod.4c00184

Natalia L Cancelarich, Miriam Arrulo, Sariah Trillo Gugliotti, Eder A Barbosa, Daniel C Moreira, Néstor G Basso, Luis Orlando Pérez, Cátia Teixeira, Paula Gomes, Beatriz G de la Torre, Fernando Albericio, Peter Eaton, José R S A Leite, Mariela M Marani

{"title":"First Bioprospecting Study of Skin Host-Defense Peptides in Odontophrynus americanus.","authors":"Natalia L Cancelarich, Miriam Arrulo, Sariah Trillo Gugliotti, Eder A Barbosa, Daniel C Moreira, Néstor G Basso, Luis Orlando Pérez, Cátia Teixeira, Paula Gomes, Beatriz G de la Torre, Fernando Albericio, Peter Eaton, José R S A Leite, Mariela M Marani","doi":"10.1021/acs.jnatprod.4c00184","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00184","url":null,"abstract":"The adaptation of amphibians to diverse environments is closely related to the characteristics of their skin. The complex glandular system of frog skin plays a pivotal role in enabling these animals to thrive in both aquatic and terrestrial habitats and consists of crucial functions such as respiration and water balance as well as serving as a defensive barrier due to the secretion of bioactive compounds. We herein report the first investigation on the skin secretion of Odontophrynus americanus, as a potential source of bioactive peptides and also as an indicator of its evolutionary adaptations to changing environments. Americanin-1 was isolated and identified as a neutral peptide exhibiting moderate antibacterial activity against E. coli. Its amphipathic sequence including 19 amino acids and showing a propensity for α-helix structure is discussed. Comparisons of the histomorphology of the skin of O. americanus with other previously documented species within the same genus revealed distinctive features in the Patagonian specimen, differing from conspecifics from other Argentine provinces. The presence of the Eberth-Katschenko layer, a prevalence of iridophores, and the existence of glycoconjugates in its serous glands suggest that the integument is adapted to retain skin moisture. This adaptation is consistent with the prevailing aridity of its native habitat.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3,"publicationDate":"2024-06-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141430890","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

UPLC-Q-TOF-MS/MS-Based Targeted Discovery of Chetomin Analogues from Chaetomium cochliodes. 基于 UPLC-Q-TOF-MS/MS 的从 Chaetomium cochliodes 中靶向发现 Chetomin 类似物的方法。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-18 DOI: 10.1021/acs.jnatprod.4c00215

Jian-Zi Liu, Yan-Duo Wang, Hui-Qi Fang, Gui-Bo Sun, Gang Ding

引用次数: 0

Facile Halogenation of Antimicrobial Peptides As Demonstrated by Producing Bromotryptophan-Labeled Nisin Variants with Enhanced Antimicrobial Activity. 通过产生具有更强抗菌活性的溴色氨酸标记的 Nisin 变体证明了抗菌肽的简易卤化。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-18 DOI: 10.1021/acs.jnatprod.4c00118

Longcheng Guo, Oscar P Kuipers, Jaap Broos

{"title":"Facile Halogenation of Antimicrobial Peptides As Demonstrated by Producing Bromotryptophan-Labeled Nisin Variants with Enhanced Antimicrobial Activity.","authors":"Longcheng Guo, Oscar P Kuipers, Jaap Broos","doi":"10.1021/acs.jnatprod.4c00118","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00118","url":null,"abstract":"Antimicrobial peptides (AMPs) have raised significant interest, forming a potential new class of antibiotics in the fight against multi-drug-resistant bacteria. Various AMPs are ribosomally synthesized and post-translationally modified peptides (RiPPs). One post-translational modification found in AMPs is the halogenation of Trp residues. This modification has, for example, been shown to be critical for the activity of the potent AMP NAI-107 from Actinoallomurus. Due to the importance of organohalogens, establishing methods for facile and selective halogen atom installation into AMPs is highly desirable. In this study, we introduce an expression system utilizing the food-grade strain Lactococcus lactis, facilitating the efficient incorporation of bromo-Trp (BrTrp) into (modified) peptides, exemplified by the lantibiotic nisin with a single Trp residue or analogue incorporated at position 1. This provides an alternative to the challenges posed by halogenase enzymes, such as poor substrate selectivity. Our method yields expression levels comparable to that of wild-type nisin, while BrTrp incorporation does not interfere with the post-translational modifications of nisin (dehydration and cyclization). One brominated nisin variant exhibits a 2-fold improvement in antimicrobial activity against two tested pathogens, including a WHO priority pathogen, while maintaining the same lipid II binding and bactericidal activity as wild-type nisin. The work presented here demonstrates the potential of this methodology for peptide halogenation, offering a new avenue for the development of diverse antimicrobial products labeled with BrTrp.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":5.1,"publicationDate":"2024-06-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141416654","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

Rogersonins C-F, 9H-Imidazo[2,1-i]purine-Incorporating Adenine-Polyketide Hybrids from an Ophiocordyceps-Associated Clonostachys rogersoniana. Rogersonins C-F，9H-咪唑并[2,1-i]嘌呤内含腺嘌呤-多酮杂交体，来自一种与麦角菌相关的 Clonostachys rogersoniana。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-18 DOI: 10.1021/acs.jnatprod.4c00266

Xintong Hou, Ruikun Wang, Chunyan Zhang, Yang Xu, Shuaiming Zhu, Yang Zhang, Xingzhong Liu, Yongsheng Che

引用次数: 0

Minor Cannabinoids as Inhibitors of Skin Inflammation: Chemical Synthesis and Biological Evaluation. 作为皮肤炎症抑制剂的小分子大麻素：化学合成与生物学评价。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-18 DOI: 10.1021/acs.jnatprod.4c00212

Alice Maiocchi, Marco Fumagalli, Manuel Vismara, Asja Blanco, Umberto Ciriello, Giuseppe Paladino, Stefano Piazza, Giulia Martinelli, Valerio Fasano, Mario Dell'Agli, Daniele Passarella

引用次数: 0

Xanthone Inhibitors of Unfolded Protein Response Isolated from Calophyllum caledonicum. 从钙叶菊中分离出的抑制折叠蛋白反应的黄酮。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-13 DOI: 10.1021/acs.jnatprod.4c00328

Marine Chambaud, Anne-Marie Le Ray, Racha Hamzi, Thomas Charpentier, Nadège Blon, Dimitri Bréard, Pierre Le Pogam, Marc Litaudon, Vincent Dumontet, Nelly Bataillé-Simoneau, Thomas Guillemette, Philippe Simoneau, Andreas Schinkovitz, David Guilet, Guillaume Viault, Pascal Richomme

引用次数: 0

Discovery of Kebanmycins with Antibacterial and Cytotoxic Activities from the Mangrove-Derived Streptomyces sp. SCSIO 40068. 从红树林产链霉菌 SCSIO 40068 中发现具有抗菌和细胞毒性活性的 Kebanmycins。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-11 DOI: 10.1021/acs.jnatprod.4c00232

Mengran Zhao, Wenjun Zhang, Chunfang Yang, Liping Zhang, Huarong Huang, Yiguang Zhu, Disna Ratnasekera, Changsheng Zhang

{"title":"Discovery of Kebanmycins with Antibacterial and Cytotoxic Activities from the Mangrove-Derived Streptomyces sp. SCSIO 40068.","authors":"Mengran Zhao, Wenjun Zhang, Chunfang Yang, Liping Zhang, Huarong Huang, Yiguang Zhu, Disna Ratnasekera, Changsheng Zhang","doi":"10.1021/acs.jnatprod.4c00232","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00232","url":null,"abstract":"Mangrove derived actinomycetes are a rich reservoir of bioactive natural products and play important roles in pharmaceutical chemistry. In a screen of actinomycetes from mangrove rhizosphere sedimental environments, the isolated strain Streptomyces sp. SCSIO 40068 displayed strong antibacterial activity. Further fractionation of the extract yielded four new compounds kebanmycins A-D (1-4) and two known analogues FD-594 (5) and the aglycon (6). The structures of 1-6 were determined based on extensive spectroscopic data and single-crystal X-ray diffraction analysis. 1-3 featured a fused pyranonaphthaxanthene as an integral part of a 6/6/6/6/6/6 polycyclic motif, and showed bioactivity against a series of Gram-positive bacteria and cytotoxicity to several human tumor cells. In addition, the kebanmycins biosynthetic gene cluster (keb) was identified in Streptomyces sp. SCSIO 40068, and KebMT2 was biochemically characterized as a tailoring sugar-O-methyltransferase, leading to a proposed biosynthetic route to 1-6. This study paves the way to further investigate 1 as a potential lead compound.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":5.1,"publicationDate":"2024-06-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141304823","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

Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells. 深海发酵真菌赤曲霉 YPGA10 的麦角甾醇衍生物和 25,28-二羟麦角甾醇诱导人结肠癌 SW620 细胞凋亡的作用

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-10 DOI: 10.1021/acs.jnatprod.4c00154

Zhen Zhang, Yuanli Li, Huannan Wang, Wei Xu, Chunying Wang, Huabin Ma, Fang Zhong, Jiazhi Ou, Zhuhua Luo, Hai-Bin Luo, Zhongbin Cheng

{"title":"Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells.","authors":"Zhen Zhang, Yuanli Li, Huannan Wang, Wei Xu, Chunying Wang, Huabin Ma, Fang Zhong, Jiazhi Ou, Zhuhua Luo, Hai-Bin Luo, Zhongbin Cheng","doi":"10.1021/acs.jnatprod.4c00154","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.4c00154","url":null,"abstract":"Ten new ergone derivatives (1-10) and five known analogues (11-15) were isolated from the deep-sea-derived fungus Aspergillus terreus YPGA10. The structures including the absolute configurations were established by detailed analysis of the NMR spectroscopic data, HRESIMS, ECD calculation, and coupling constant calculation. All the structures are characterized by a highly conjugated 25-hydroxyergosta-4,6,8(14),22-tetraen-3-one nucleus. Structurally, compound 2 bearing a 15-carbonyl group and compounds 5-7 possessing a 15β-OH/OCH3 group are rarely encountered in ergone derivatives. Bioassay results showed that compounds 1 and 11 demonstrated cytotoxic effects on human colon cancer SW620 cells with IC50 values of 8.4 and 3.1 μM, respectively. Notably, both compounds exhibited negligible cytotoxicity on the human normal lung epithelial cell BEAS-2B. Compound 11 was selected for preliminary mechanistic study and was found to inhibit cell proliferation and induce apoptosis in human colon cancer SW620 cells. In addition, compound 1 displayed cytotoxic activity against five human leukemia cell lines with IC50 values ranging from 5.7 to 8.9 μM. Our study demonstrated that compound 11 may serve as a potential candidate for the development of anticolorectal cancer agents.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":5.1,"publicationDate":"2024-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141295084","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 Screening of 10,240 NatureBank Fractions Identifies Nematicidal Activity in Agelasine-Containing Extracts from Sponges. 对10,240个NatureBank提取物的筛选发现了海绵中含褐藻素提取物的杀线虫活性。

IF 5.1 2区生物学

Journal of Natural Products Pub Date : 2024-06-09 DOI: 10.1021/acs.jnatprod.3c01212

Gastón Risi, Miaomiao Liu, Franco Vairoletti, Ronald J Quinn, Gustavo Salinas

{"title":"A Screening of 10,240 NatureBank Fractions Identifies Nematicidal Activity in Agelasine-Containing Extracts from Sponges.","authors":"Gastón Risi, Miaomiao Liu, Franco Vairoletti, Ronald J Quinn, Gustavo Salinas","doi":"10.1021/acs.jnatprod.3c01212","DOIUrl":"https://doi.org/10.1021/acs.jnatprod.3c01212","url":null,"abstract":"Nematode infections affect a fifth of the human population, livestock, and crops worldwide, imposing a burden to global public health and economies, particularly in developing nations. Resistance to commercial anthelmintics has increased over the years in livestock infections and driven the pursuit for new drugs. We herein present a rapid, cost-effective, and automated assay for nematicide discovery using the free-living nematode Caenorhabditis elegans to screen a highly diverse natural product library enriched in bioactive molecules. Screening of 10,240 fractions obtained from extracts of various biological sources allowed the identification of 7 promising hit fractions, all from marine sponges. These fractions were further assayed for nematicidal activity against the sheep nematode parasite Haemonchus contortus and for innocuity in zebrafish. The most active extracts against parasites and innocuous toward vertebrates belong to two chemotypes. High-performance liquid chromatography (HPLC) coupled with nuclear magnetic resonance (NMR) revealed that the most abundant compound in one chemotype is halaminol A, an aminoalcohol previously identified in a small screen against H. contortus. Terpene-nucleotide hybrids known as agelasines predominate in the other chemotype. This study reinforces the power of C. elegans for nematicide discovery from large collections and the potential of the chemical diversity derived from marine invertebrate biota.","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":5.1,"publicationDate":"2024-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141295083","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