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- Author:
- Kaitlyn Varela; Hafij Al Mahmud; Hadi D. Arman; Luis R. Martinez; Catherine A. Wakeman; Francis K. Yoshimoto
- Source:
- Journal of natural products 2022 v.85 no.4 pp. 951-962
- ISSN:
- 1520-6025
- Subject:
- Cryptococcus neoformans; Plasmodium falciparum; Staphylococcus aureus; air; aromatic compounds; aromatization; artemisinin; autoxidation; bioactive properties; biosynthesis; fungi; malaria; minimum inhibitory concentration; parasites; pathogens
- Abstract:
- ... Dihydroartemisinic acid (DHAA) is a plant natural product that undergoes a spontaneous endoperoxide-forming cascade reaction to yield artemisinin in the presence of air. The endoperoxide functional group gives artemisinin its biological activity that kills Plasmodium falciparum, the parasite that causes malaria. To enhance our understanding of the mechanism of this cascade reaction, 2,3-didehydrod ...
- DOI:
- 10.1021/acs.jnatprod.1c01101
- https://doi.org/10.1021/acs.jnatprod.1c01101
- Author:
- Lei Wang; Virginia Linares-Otoya; Yang Liu; Ute Mettal; Michael Marner; Lizbeth Armas-Mantilla; Sabine Willbold; Tibor Kurtán; Luis Linares-Otoya; Till F. Schäberle
- Source:
- Journal of natural products 2022 v.85 no.4 pp. 1039-1051
- ISSN:
- 1520-6025
- Subject:
- Aspergillus flavus; Bacillus subtilis; Caenorhabditis elegans; Candida albicans; Escherichia coli; Flavobacterium; Listeria monocytogenes; Mycobacterium smegmatis; Staphylococcus aureus; Tenacibaculum; biochemical pathways; biosynthesis; decarboxylation; imidazoles; metabolites; minimum inhibitory concentration; phenethylamine; phenylalanine; spectral analysis; transporters
- Abstract:
- ... The bacterial genus Tenacibaculum has been associated with various ecological roles in marine environments. Members of this genus can act, for example, as pathogens, predators, or episymbionts. However, natural products produced by these bacteria are still unknown. In the present work, we investigated a Tenacibaculum strain for the production of antimicrobial metabolites. Six new phenethylamine (P ...
- DOI:
- 10.1021/acs.jnatprod.1c01173
- https://doi.org/10.1021/acs.jnatprod.1c01173
- Author:
- Kai Jiang; Xiaoli Yan; Zixin Deng; Chun Lei; Xudong Qu
- Source:
- Journal of natural products 2022 v.85 no.4 pp. 943-950
- ISSN:
- 1520-6025
- Subject:
- Bacillus subtilis; Staphylococcus aureus; Streptomyces kanamyceticus; biocatalysis; genome; transferases
- Abstract:
- ... Genome mining and biocatalytic modification of chemical structures are critical methods to develop new antibiotics. In this study, eight new fasamycins (3, 4, 6, and 8–12) along with five known analogues (1, 2, 5, 7, and 13) were obtained by the overexpression of two phosphopantetheinyl transferases (PPtases) in Streptomyces kanamyceticus and biocatalytic transformation with two halogenases. These ...
- DOI:
- 10.1021/acs.jnatprod.1c01089
- https://doi.org/10.1021/acs.jnatprod.1c01089
- Author:
- Mamadou A. Baldé; Emmy Tuenter; Mohamed S. Traoré; Laura Peeters; An Matheeussen; Paul Cos; Guy Caljon; Tom Vermeyen; Wouter Herrebout; Aliou M. Balde; Kenn Foubert; Luc Pieters
- Source:
- Journal of natural products 2021 v.84 no.3 pp. 666-675
- ISSN:
- 1520-6025
- Subject:
- Candida albicans; Plasmodium falciparum; Staphylococcus aureus; Terminalia; antimalarials; antiplasmodial properties; bark; mass spectrometry; nuclear magnetic resonance spectroscopy; phytochemicals; triterpenoids
- Abstract:
- ... Phytochemical investigation of the n-BuOH extract of the roots of Terminalia albida Sc. Elliot (Combretaceae) led to the isolation and identification of 10 oleanane triterpenoids (1–10), among which six new compounds, i.e., albidanoside A (2), albidic acid A (4), albidinolic acid (5), albidienic acid (8), albidolic acid (9), and albidiolic acid (10), and two triterpenoid aglycones, i.e., albidic a ...
- DOI:
- 10.1021/acs.jnatprod.0c01119
- https://doi.org/10.1021/acs.jnatprod.0c01119
- Author:
- Katherine Yasmin M. Garcia; Chayanard Phukhamsakda; Mark Tristan J. Quimque; Kevin D. Hyde; Marc Stadler; Allan Patrick G. Macabeo
- Source:
- Journal of natural products 2021 v.84 no.7 pp. 2053-2058
- ISSN:
- 1520-6025
- Subject:
- Dothideomycetes; Spartium junceum; Staphylococcus aureus; fungi; mass spectrometry; polyketides; spectral analysis
- Abstract:
- ... Sparticols A (1) and B (2), two catechol-bearing naphthalenedioxy derivatives, were isolated from the submerged culture of the Spanish broom inhabiting Dothideomycetes fungus, Sparticola junci. The structures of 1 and 2 were established by NMR spectroscopic analysis and high-resolution mass spectrometry. The 8S absolute configuration of their β-hydroxy functionalities was determined by ECD-TDDFT. ...
- DOI:
- 10.1021/acs.jnatprod.1c00415
- https://doi.org/10.1021/acs.jnatprod.1c00415
- Author:
- Divinah K. Nyamboki; Kibrom G. Bedane; Khadija Hassan; Lukas Brieger; Carsten Strohmann; Michael Spiteller; Josphat C. Matasyoh
- Source:
- Journal of natural products 2021 v.84 no.5 pp. 1453-1458
- ISSN:
- 1520-6025
- Subject:
- Bersama; Staphylococcus aureus; X-ray diffraction; bark; bufadienolides; cell lines; cytotoxicity; neoplasm cells
- Abstract:
- ... Three new bufadienolides, namely, paulliniogenin A (1), paulliniogenin B (2), and 16β-formyloxybersamagenin 1,3,5-orthoacetate (3), together with two known bufadienolides and six known phenolic substances, were isolated from the stem bark of Bersama abyssinica subsp. abyssinica and B. abyssinica subsp. paullinioides. The structures of the compounds were elucidated based on their NMR and HRMS data ...
- DOI:
- 10.1021/acs.jnatprod.0c01141
- https://doi.org/10.1021/acs.jnatprod.0c01141
- Author:
- Xia Cheng; Xiao Liang; Fei-Hua Yao; Xiao-Bo Liu; Shu-Hua Qi
- Source:
- Journal of natural products 2021 v.84 no.11 pp. 2945-2952
- ISSN:
- 1520-6025
- Subject:
- Staphylococcus aureus; X-ray diffraction; antibacterial properties; fungi; quantum mechanics; spectroscopy; triterpenoids
- Abstract:
- ... Simplifusidic acids A–K (1–11), 11 new fusidane-type nortriterpenoids, were isolated from the marine-derived fungus Simplicillium sp. SCSIO 41513. Compound 1 possessed an unprecedented fusidane triterpene skeleton with a 6/6/7/5/5 polycyclic system. Their structures were elucidated by spectroscopic methods, and their absolute configurations were further determined by quantum chemical calculations ...
- DOI:
- 10.1021/acs.jnatprod.1c00776
- https://doi.org/10.1021/acs.jnatprod.1c00776
- Author:
- Tessa B. Moyer; Jessie L. Allen; Lindsey N. Shaw; Leslie M. Hicks
- Source:
- Journal of natural products 2021 v.84 no.2 pp. 444-452
- ISSN:
- 1520-6025
- Subject:
- Acinetobacter baumannii; Amaranthus tricolor; Enterobacter cloacae; Enterococcus faecium; Klebsiella pneumoniae; Staphylococcus aureus; antimicrobial peptides; bioactive properties; computer simulation; disulfides; genomics; lipids; mass spectrometry; peptidomics; prediction; proteolysis
- Abstract:
- ... Traditional medicinal plants are rich reservoirs of antimicrobial agents, including antimicrobial peptides (AMPs). Advances in genomic sequencing, in silico AMP predictions, and mass spectrometry-based peptidomics facilitate increasingly high-throughput bioactive peptide discovery. Herein, Amaranthus tricolor aerial tissue was profiled via MS-based proteomics/peptidomics, identifying AMPs predicte ...
- DOI:
- 10.1021/acs.jnatprod.0c01203
- https://doi.org/10.1021/acs.jnatprod.0c01203
- Author:
- Ziwei Yao; Changli Sun; Yuhui Xia; Fang Wang; Liwu Fu; Junying Ma; Qinglian Li; Jianhua Ju
- Source:
- Journal of natural products 2021 v.84 no.8 pp. 2217-2225
- ISSN:
- 1520-6025
- Subject:
- Candida albicans; Enterococcus faecium; Staphylococcus aureus; Streptomyces; antibiotic resistance; biosynthesis; cytotoxicity; mutants
- Abstract:
- ... Through precursor-directed biosynthesis, feeding halogenated (F-, Cl-, Br-, I-) or methoxy-substituted 4-methyl-3-hydroxyanthranilic acid (4-MHA) analogues to the acnGHLM-deleted mutant strain of Streptomyces costaricanus SCSIO ZS0073 led to the production of ten new actinomycin analogues (4–13). Several of the actinomycin congeners displayed impressive antimicrobial activities, with MIC values sp ...
- DOI:
- 10.1021/acs.jnatprod.1c00294
- https://doi.org/10.1021/acs.jnatprod.1c00294
- Author:
- Sonja L. Knowles; Christopher D. Roberts; Mario Augustinović; Laura Flores-Bocanegra; Huzefa A. Raja; Kimberly N. Heath-Borrero; Joanna E. Burdette; Joseph O. Falkinham III; Cedric J. Pearce; Nicholas H. Oberlies
- Source:
- Journal of natural products 2021 v.84 no.4 pp. 1254-1260
- ISSN:
- 1520-6025
- Subject:
- Clonostachys; Staphylococcus aureus; enantiomers; fungi; phylogeny; secondary metabolites
- Abstract:
- ... Four new bislactones, dihydroacremonol (1), clonostachyone (2), acremodiol B (3), and acremodiol C (4), along with one known compound, hymeglusin (5), were isolated from cultures of two fungal strains (MSX59876 and MSX59260). Both strains were identified based on phylogenetic analysis of molecular data as Clonostachys spp.; yet, they biosynthesized a suite of related, but different, secondary meta ...
- DOI:
- 10.1021/acs.jnatprod.0c01309
- https://doi.org/10.1021/acs.jnatprod.0c01309
- Author:
- Ying Jin; Nuerbiye Aobulikasimu; Zengguang Zhang; Chengbin Liu; Bixuan Cao; Bin Lin; Peipei Guan; Yu Mu; Yi Jiang; Li Han; Xueshi Huang
- Source:
- Journal of natural products 2020 v.83 no.12 pp. 3545-3553
- ISSN:
- 1520-6025
- Subject:
- Amycolatopsis; Bacillus subtilis; Escherichia coli; Staphylococcus aureus; aromatic compounds; culture media; dose response; metabolites; spectral analysis
- Abstract:
- ... Eleven metabolites, six echinosporins (1–6), four dibenzoyls (7–10), and an aromatic compound (11), were isolated from the fermentation broth of lichen-associated Amycolatopsis hippodromi. The structures of the new compounds (1–5, 8–11) were elucidated by comprehensive spectroscopic analysis including data from experimental and calculated ECD spectra. Amycolasporins A–C (1–3) demonstrated antibact ...
- DOI:
- 10.1021/acs.jnatprod.0c00547
- https://doi.org/10.1021/acs.jnatprod.0c00547
- Author:
- George F. Neuhaus; Sandra Loesgen
- Source:
- Journal of natural products 2020 v.84 no.1 pp. 37-45
- ISSN:
- 1520-6025
- Subject:
- Aspergillus; Enterococcus faecium; Staphylococcus aureus; fungi; mass spectrometry; metabolites; multiple drug resistance; sesquiterpenoids
- Abstract:
- ... Bioactivity-guided isolation of Aspergillus ustus led to the discovery of five new drimane sesquiterpenes, named ustusal A, ustusolate F and G, and ustusoic acid A and B, 1–5 respectively. Structural elucidation of these fungal terpenes relied on 1D and 2D NMR techniques, high-resolution mass spectrometry, and chiroptical properties. Their relative configurations were determined by NMR methods, wh ...
- DOI:
- 10.1021/acs.jnatprod.0c00910
- https://doi.org/10.1021/acs.jnatprod.0c00910
- Author:
- Jin-Ling Chang; Hong-Zhe Xu; Jia Zhou; Ming Zhou; Xuke Zhang; Yuanqiang Guo; Han-Li Ruan
- Source:
- Journal of natural products 2020 v.83 no.12 pp. 3606-3613
- ISSN:
- 1520-6025
- Subject:
- Candida albicans; Escherichia coli; Penicillium; Staphylococcus aureus; circular dichroism spectroscopy; density functional theory; fermentation; fungi; moieties; spectral analysis; thiophene
- Abstract:
- ... Ten novel (1, 2, 3a, 3b, 4a, 4b, 5a, 5b, 6a, and 6b) furancarboxylic acids including four pairs of epimers (3a, 3b; 4a, 4b; 5a, 5b; 6a, 6b), together with seven known analogues (7a, 7b, 8a, 8b, 9a, 9b, and 10), were isolated from the fermentation of the soil-derived fungus Penicillium sp. sb62. Their structures were established on the basis of spectroscopic data analysis, and the absolute configur ...
- DOI:
- 10.1021/acs.jnatprod.0c00758
- https://doi.org/10.1021/acs.jnatprod.0c00758
- Author:
- Mario Wibowo; Charlotte H. Gotfredsen; Elisa Sassetti; Jette Melchiorsen; Mads Hartvig Clausen; Lone Gram; Ling Ding
- Source:
- Journal of natural products 2020 v.83 no.12 pp. 3519-3525
- ISSN:
- 1520-6025
- Subject:
- Candida albicans; Staphylococcus aureus; Streptomyces; Vibrio anguillarum; alanine; cytotoxicity; humans; neoplasm cells
- Abstract:
- ... Azoxy compounds belong to a small group of natural products sharing a common functional group with the general structure RN = N⁺(O–)R. Three new azoxides, azodyrecins A–C (1–3), were isolated from a soil-derived Streptomyces sp. strain P8-A2. The cis-alkenyl unit in 1–3 was found to readily isomerize to the trans-congeners (4–6). The structures of the new compounds were determined by detailed spec ...
- DOI:
- 10.1021/acs.jnatprod.0c00339
- https://doi.org/10.1021/acs.jnatprod.0c00339
- Author:
- Ignacio Gutiérrez-del-Río; Nelly Brugerolle de Fraissinette; Raquel Castelo-Branco; Flavio Oliveira; João Morais; Saúl Redondo-Blanco; Claudio J. Villar; María José Iglesias; Raquel Soengas; Virginio Cepas; Yuly López Cubillos; Giacomo Sampietro; Liliana Rodolfi; Felipe Lombó; Sara M. Soto González; Fernando López Ortiz; Vitor Vasconcelos; Mariana A. Reis
- Source:
- Journal of natural products 2020 v.83 no.6 pp. 1885-1890
- ISSN:
- 1520-6025
- Subject:
- Candida parapsilosis; Cyanobacteria; Staphylococcus aureus; Staphylococcus hominis; biofilm; chlorinated fatty acids; coagulase negative staphylococci; data collection; dodecanoic acid; esters; fungi; lactic acid; mass spectrometry; nuclear magnetic resonance spectroscopy
- Abstract:
- ... Four natural lactylates of chlorinated fatty acids, chlorosphaerolactylates A–D (1–4), were isolated from the methanolic extract of the cyanobacterium Sphaerospermopsis sp. LEGE 00249 through a combination of bioassay-guided and MS-guided approaches. Compounds 1–4 are esters of (mono-, di-, or tri)chlorinated lauric acid and lactic acid, whose structures were assigned on the basis of spectrometric ...
- DOI:
- 10.1021/acs.jnatprod.0c00072
- https://doi.org/10.1021/acs.jnatprod.0c00072
- Author:
- Davide Righi; Robin Huber; Alexey Koval; Laurence Marcourt; Sylvain Schnee; Anaïs Le Floch; Verena Ducret; Remo Perozzo; Concetta C. de Ruvo; Nicole Lecoultre; Emilie Michellod; Samad N. Ebrahimi; Elisabeth Rivara-Minten; Vladimir L. Katanaev; Karl Perron; Jean-Luc Wolfender; Katia Gindro; Emerson F. Queiroz
- Source:
- Journal of natural products 2020 v.83 no.8 pp. 2347-2356
- ISSN:
- 1520-6025
- Subject:
- Botrytis cinerea; Pseudomonas aeruginosa; Staphylococcus aureus; anti-infective agents; antibacterial properties; biotransformation; breasts; carcinoma; cytotoxicity; enzyme activity; epithelial cells; human cell lines; humans; liver; multiple drug resistance; pterostilbene; resveratrol; solubility
- Abstract:
- ... The biotransformation of a mixture of resveratrol and pterostilbene was performed by the protein secretome of Botrytis cinerea. Several reaction conditions were tested to overcome solubility issues and to improve enzymatic activity. Using MeOH as cosolvent, a series of unusual methoxylated compounds was generated. The reaction was scaled-up, and the resulting mixture purified by semipreparative HP ...
- DOI:
- 10.1021/acs.jnatprod.0c00071
- https://doi.org/10.1021/acs.jnatprod.0c00071
- Author:
- Carla Menegatti; Vitor Bruno Lourenzon; Diego Rodríguez-Hernández; Weilan Gomes da Paixão Melo; Leonardo Luiz Gomes Ferreira; Adriano Defini Andricopulo; Fabio Santos do Nascimento; Mônica Tallarico Pupo
- Source:
- Journal of natural products 2020 v.83 no.3 pp. 610-616
- ISSN:
- 1520-6025
- Subject:
- Leishmania infantum; Melipona scutellaris; Paenibacillus larvae; Staphylococcus aureus; Streptomyces; amino acids; anti-infective agents; entomopathogens; microorganisms; nuclear magnetic resonance spectroscopy; pollinators; social insects; stingless bees
- Abstract:
- ... Social insects establish complex interactions with microorganisms, some of which play defensive roles in colony protection. The important role of pollinators such as the stingless bee Melipona scutellaris in nature encouraged us to pursue efforts to study its associated microbiota. Here we describe the discovery of two novel cyclic hexadepsipeptides, meliponamycin A (1) and meliponamycin B (2), fr ...
- DOI:
- 10.1021/acs.jnatprod.9b01011
- https://doi.org/10.1021/acs.jnatprod.9b01011
- Author:
- KH Ahammad Uz Zaman; Zhenquan Hu; Xiaohua Wu; Shaobin Hou; Jennifer Saito; Tamara P. Kondratyuk; John M. Pezzuto; Shugeng Cao
- Source:
- Journal of natural products 2020 v.83 no.3 pp. 730-737
- ISSN:
- 1520-6025
- Subject:
- Aspergillus terreus; Escherichia coli; Staphylococcus aureus; chemical derivatives; fumagillin; inhibitory concentration 50; mass spectrometry; moieties; mountains; nuclear magnetic resonance spectroscopy; soil; transcription factor NF-kappa B; Hawaii (island)
- Abstract:
- ... Two new helvolic acid analogues (1 and 2) and one new fumagillin derivative containing an octahydroisobenzofuran moiety (3), together with four known compounds (4–7), were isolated from an Aspergillus terreus, isolated from soil collected from Mauna Kea, the highest mountain in Hawaii. Compound 4 was recorded in SciFinder with a CAS Registry Number of 1379525-35-5, but it was not documented in the ...
- DOI:
- 10.1021/acs.jnatprod.9b01190
- https://doi.org/10.1021/acs.jnatprod.9b01190
- Author:
- Ya-Pei Liu; Quan Dai; Wen-Xuan Wang; Juan He; Zheng-Hui Li; Tao Feng; Ji-Kai Liu
- Source:
- Journal of natural products 2020 v.83 no.5 pp. 1725-1729
- ISSN:
- 1520-6025
- Subject:
- Psathyrella; Salmonella enterica; Staphylococcus aureus; biochemical pathways; diterpenoids; spectroscopy
- Abstract:
- ... Two skeletally novel tetracyclic diterpenoids, psathyrins A (1) and B (2), have been characterized from cultures of the basidiomycete Psathyrella candolleana. Their structures including absolute configurations were established by means of spectroscopic methods, as well as ECD calculations. They possess a novel 5/5/4/6-fuesd ring system, for which the biosynthetic pathway is proposed. Compounds 1 a ...
- DOI:
- 10.1021/acs.jnatprod.0c00269
- https://doi.org/10.1021/acs.jnatprod.0c00269
- Author:
- Natalia L. Cancelarich; Natalia Wilke; Marı́a L. Fanani; Daniel C. Moreira; Luis O. Pérez; Eder Alves Barbosa; Alexandra Plácido; Renato Socodato; Camila C. Portugal; João B. Relvas; Beatriz G. de la Torre; Fernando Albericio; Néstor G. Basso; José R. Leite; Mariela M. Marani
- Source:
- Journal of natural products 2020 v.83 no.4 pp. 972-984
- ISSN:
- 1520-6025
- Subject:
- Escherichia coli; Leptodactylidae; Staphylococcus aureus; antimicrobial peptides; antimicrobial properties; cell structures; databases; endangered species; frogs; indigenous species; innate immunity; models; natural resources conservation; permeability; skin glands; therapeutics; Argentina
- Abstract:
- ... The skin glands of amphibian species hold a major component of their innate immunity, namely a unique set of antimicrobial peptides (AMPs). Although most of them have common characteristics, differences in AMP sequences allow a huge repertoire of biological activity with varying degrees of efficacy. We present the first study of the AMPs from Pleurodema somuncurence (Anura: Leptodactylidae: Leiupe ...
- DOI:
- 10.1021/acs.jnatprod.9b00906
- https://doi.org/10.1021/acs.jnatprod.9b00906