scholarly journals Antibacterial Alkaloids and Polyketide Derivatives from the Deep Sea-Derived Fungus Penicillium cyclopium SD-413

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 553
Author(s):  
Yan-He Li ◽  
Xiao-Ming Li ◽  
Xin Li ◽  
Sui-Qun Yang ◽  
Xiao-Shan Shi ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Deep Sea ◽  
Density Functional ◽  
Pathogenic Bacteria ◽  
Micrococcus Luteus ◽  
Vibrio Anguillarum ◽  
2D Nmr ◽  
Edwardsiella Tarda ◽  
Spectrometric Analysis ◽  
Mic Minimum Inhibitory Concentration

Nine secondary metabolites (1–9), including two new polyketide derivatives 9-dehydroxysargassopenilline A (4) and 1,2-didehydropeaurantiogriseol E (5), along with seven known related secondary metabolites (1–3 and 6–9), were isolated and identified from the deep sea-derived fungus Penicilliumcyclopium SD-413. Their structures were elucidated on the basis of 1D/2D NMR spectroscopic and mass spectrometric analysis and the absolute configurations were determined by the combination of NOESY correlations and time-dependent density functional (TDDFT) ECD calculations. Compounds 1–9 inhibited some pathogenic bacteria including Escherichia coli, E. ictaluri, Edwardsiella tarda, Micrococcus luteus, Vibrio anguillarum, and V. harveyi, with MIC (minimum inhibitory concentration) values ranging from 4 to 32 μg/mL.

scholarly journals Antimicrobial Sesquiterpenoid Derivatives and Monoterpenoids from the Deep-Sea Sediment-Derived Fungus Aspergillus versicolor SD-330

Marine Drugs ◽  
2019 ◽  
Vol 17 (10) ◽  
pp. 563 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xiao-Ming Li ◽  
Xiu-Li Yin ◽  
Xin Li ◽  
Bin-Gui Wang
Keyword(s):  
Deep Sea ◽  
Pathogenic Bacteria ◽  
Vibrio Anguillarum ◽  
Antimicrobial Activities ◽  
Crystallographic Analysis ◽  
Edwardsiella Tarda ◽  
Aspergillus Versicolor ◽  
Deep Sea Sediment ◽  
X Ray ◽  
The Absolute

Two new antimicrobial bisabolane-type sesquiterpenoid derivatives, ent-aspergoterpenin C (compound 1) and 7-O-methylhydroxysydonic acid (2), and two new butyrolactone-type monoterpenoids, pestalotiolactones C (3) and D (4), along with a known monoterpenoid pestalotiolactone A (5) and four known bisabolane sesquiterpenoids (6−9), were isolated and identified from the deep-sea sediment-derived fungus Aspergillus versicolor SD-330. The structures of these compounds were elucidated on the basis of spectroscopic analysis, and the absolute configurations of the new compounds 1−4 were determined by the combination of NOESY and TDDFT-ECD calculations and X-ray crystallographic analysis. Additionally, we first determined and reported the absolute configuration of the known monoterpenoid pestalotiolactone A (5) through the X-ray crystallographic experiment. All of these isolated compounds were evaluated for antimicrobial activities against human and aquatic pathogenic bacteria. Compounds 1, 2, 6 and 9 exhibited selective inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio anguillarum and V. harveyi, with MIC values ranging from 1.0 to 8.0 μg/mL.

scholarly journals 20-Nor-Isopimarane Epimers Produced by Aspergillus wentii SD-310, a Fungal Strain Obtained from Deep Sea Sediment

Marine Drugs ◽  
2018 ◽  
Vol 16 (11) ◽  
pp. 440 ◽  
Author(s):  
Xiao-Dong Li ◽  
Xin Li ◽  
Xiao-Ming Li ◽  
Gang-Ming Xu ◽  
Yang Liu ◽  
...  
Keyword(s):  
Deep Sea ◽  
Density Functional ◽  
Pathogenic Bacteria ◽  
Pathogenic Fungi ◽  
Antimicrobial Activities ◽  
Crystallographic Analysis ◽  
Edwardsiella Tarda ◽  
Separation And Purification ◽  
Deep Sea Sediment ◽  
Aspergillus Wentii

Four new uncommon 20-nor-isopimarane diterpenoid epimers, aspewentins I−L (1–4), together with a new methylated derivative of 3, aspewentin M (5), were isolated from the deep sea sediment-derived fungus Aspergillus wentii SD-310. The very similar structures of these epimers made the separation and purification procedures difficult. The structures of compounds 1–5 were illustrated based on spectroscopic analysis, and the absolute configurations of compounds 1–5 were unambiguously determined by the combination of NOESY, time-dependent density functional (TDDFT)-ECD calculations, and X-ray crystallographic analysis. These metabolites represented the rare examples of 20-nor-isopimarane analogues possessing a cyclohexa-2,5-dien-1-one moiety. These compounds were tested for antimicrobial activities against human and aquatic pathogenic bacteria, as well as plant-pathogenic fungi. While compounds 1 and 2 exhibited inhibitory activities against zoonotic pathogenic bacteria such as Escherichia coli, Edwardsiella tarda, Vibrio harveyi, and V. parahaemolyticus, compound 5 showed potent activity against the plant pathogen Fusarium graminearum.

scholarly journals Two New Piperazine-Triones from a Marine-Derived Streptomycetes sp. Strain SMS636

Marine Drugs ◽  
2019 ◽  
Vol 17 (3) ◽  
pp. 186 ◽  
Author(s):  
Xiuli Xu ◽  
Jiahui Han ◽  
Rui Lin ◽  
Steven Polyak ◽  
Fuhang Song
Keyword(s):  
Staphylococcus Aureus ◽  
Minimum Inhibitory Concentration ◽  
Secondary Metabolites ◽  
Deep Sea ◽  
Spectroscopic Analysis ◽  
Inhibitory Concentration ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Bacillus Calmette Guerin ◽  
Methicillin Resistant

Two new piperazine-triones lansai E and F (1, 2), together with four known secondary metabolites lansai D (3), 1-N-methyl-(E,Z)-albonoursin (4), imidazo[4,5-e]-1,2,4-triazine (5), and streptonigrin (6) were isolated from a deep-sea-derived Streptomycetes sp. strain SMS636. The structures of the isolated compounds were confirmed by comprehensive spectroscopic analysis, including HRESIMS, 1D and 2D NMR. Compound 4 exhibited moderate antibacterial activities against Staphylococcus aureus and methicillin resistant S. aureus (MRSA) with Minimum Inhibitory Concentration (MIC) values of 12.5 and 25 μg/mL, respectively. Compound 6 displayed significant antibacterial activities against S. aureus, MRSA and Bacillus Calmette-Guérin (BCG) with MIC values of 0.78, 0.78 and 1.25 μg/mL, respectively.

scholarly journals Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4596 ◽  
Author(s):  
Yu-Jing Liu ◽  
Jian-Long Zhang ◽  
Chen Li ◽  
Xue-Gen Mu ◽  
Xiao-Li Liu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Pathogenic Bacteria ◽  
2D Nmr ◽  
Aspergillus Sydowii ◽  
Isolation And Identification ◽  
Spectrometric Data ◽  
Lead Compounds ◽  
Acid Analogue ◽  
Chorismic Acid ◽  
Quantum Chemical Computations

Marine-derived fungi are considered to be valuable producers of bioactive secondary metabolites used as lead compounds with medicinal importance. In this study, chemical investigation of the seawater-derived fungus Aspergillus sydowii SW9 led to the isolation and identification of one new quinazolinone alkaloid, 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one (1), one new aromatic bisabolene-type sesquiterpenoid, (2) and one new chorismic acid analogue (3), as well as two known alkaloids (compounds 4 and 5). Their structures were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 2 and 3 were assigned by the analysis of ECD spectra aided by quantum chemical computations. Compounds 1, 2, and 4 exhibited selective inhibitory activities against the human pathogenic bacteria Escherichia coli, Staphylococcus aureus, S. epidermidis, and Streptococcus pneumoniae, with MIC values ranging from 2.0 to 16 μg/mL.

scholarly journals Secondary metabolites of Antarctic fungi antagonistic to aquatic pathogenic bacteria

2018 ◽  
Vol 13 (1) ◽  
pp. 11-21 ◽  
Author(s):  
Huibin Zhao ◽  
Chuner Cai ◽  
Xiaoyu Liu ◽  
Binghua Jiao ◽  
Bo Chen ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Secondary Metabolites ◽  
Molecular Identification ◽  
Streptococcus Agalactiae ◽  
Aeromonas Hydrophila ◽  
Pathogenic Bacteria ◽  
Vibrio Anguillarum ◽  
Fermentation Liquor ◽  
Ph Curve ◽  
First Time

AbstractPolar microbial derived antibiotics have potential as alternatives to traditional antibiotics in treating fish against pathogenic bacteria. In this paper, 23 strains of polar fungi were fermented to detect bacteriostatic products on three aquatic pathogenic bacteria, subsequently the active fungus was identified. It was indicated that secondary metabolites of 23 strains weredistinct; of these, the extract of strain B-7 (belonging toBjerkanderaaccording to molecular identification) demonstrated a strong antibacterial activity toStreptococcus agalactiae,Vibrio anguillarumandAeromonas hydrophilaATCC7966 by Kirby-Bauerpaper strip method. During one fermentation cycle, the pH curve of the fermentation liquor became lowest (4.0) on the 4thday and rose back to 7.6 finally after 5 days, The residual sugar curve was decreased before stablising on the 6thday. It is presumed that a large amount of alkaline secondary metabolites might have been produced during fermentation. This study focuses on antagonism between aquatic pathogenic bacteria and fermentation metabolites from Antarctic fungi for the first time, which may provide data on research of antibiotics against aquatic pathogenic bacteria.

scholarly journals Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 157
Author(s):  
Jin Yang ◽  
Lizhi Gong ◽  
Miaomiao Guo ◽  
Yu Jiang ◽  
Yi Ding ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Density Functional ◽  
Pathogenic Bacteria ◽  
Pathogenic Fungi ◽  
Human Monocyte ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Planar Structures ◽  
Monocyte Cell ◽  
Aspergillus Sp

Six new prenylated indole diketopiperazine alkaloids, asperthrins A–F (1–6), along with eight known analogues (7–14), were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Their planar structures and absolute configurations were elucidated by HR-ESI-MS, 1D/2D NMR data, and time-dependent density functional theory (TDDFT)/ECD calculation. The isolated compounds were assayed for their inhibition against three agricultural pathogenic fungi, four fish pathogenic bacteria, and two agricultural pathogenic bacteria. Compound 1 exhibited moderate antifungal and antibacterial activities against Vibrioanguillarum, Xanthomonas oryzae pv. Oryzicola, and Rhizoctoniasolani with minimal inhibitory concentration (MIC) values of 8, 12.5, and 25 μg/mL, respectively. Furthermore, 1 displayed notable anti-inflammatory activity with IC50 value of 1.46 ± 0.21 μM in Propionibacteriumacnes induced human monocyte cell line (THP-1).

Antimicrobial properties of actively purified secondary metabolites isolated from different marine organisms

2020 ◽  
Vol 21 ◽  
Author(s):  
Nilushi Indika Bamunu Arachchige ◽  
Fazlurrahman Khan ◽  
Young-Mog Kim
Keyword(s):  
Secondary Metabolites ◽  
Pathogenic Bacteria ◽  
Antimicrobial Agents ◽  
Bacterial Species ◽  
Antimicrobial Properties ◽  
Antimicrobial Effect ◽  
Cost Effective ◽  
Resistance Mechanisms ◽  
Marine Organisms ◽  
Antimicrobial Compounds

Background: The treatment of infection caused by pathogenic bacteria becomes one of the serious concerns globally. The failure in the treatment was found due to the exhibition of multiple resistance mechanisms against the antimicrobial agents. Emergence of resistant bacterial species has also been observed due to prolong treatment using conventional antibiotics. To combat these problems, several alternative strategies have been employed using biological and chemically synthesized compounds as antibacterial agents. Marine organisms considered as one of the potential sources for the isolation of bioactive compounds due to the easily available, cost-effective, and eco-friendly. Methods: The online search methodology was adapted for the collection of information related to the antimicrobial properties of marine-derived compounds. These compound has been isolated and purified by different purification techniques, and their structure also characterized. Furthermore, the antibacterial activities have been reported by using broth microdilution as well as disc diffusion assays. Results: The present review paper describes the antimicrobial effect of diverse secondary metabolites which are isolated and purified from the different marine organisms. The structural elucidation of each secondary metabolite has also been done in the present paper, which will help for the in silico designing of the novel and potent antimicrobial compounds. Conclusion: A thorough literature search has been made and summarizes the list of antimicrobial compounds that are isolated from both prokaryotic and eukaryotic marine organisms. The information obtained from the present paper will be helpful for the application of marine compounds as antimicrobial agents against different antibiotic-resistant human pathogenic bacteria.

scholarly journals Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽  
2020 ◽  
Vol 19 (1) ◽  
pp. 9
Author(s):  
Ya-Ping Liu ◽  
Sheng-Tao Fang ◽  
Zhen-Zhen Shi ◽  
Bin-Gui Wang ◽  
Xiao-Nian Li ◽  
...  
Keyword(s):  
Deep Sea ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
Penicillium Oxalicum ◽  
Marine Phytoplankton ◽  
Cold Seep ◽  
Phytoplankton Species ◽  
X Ray ◽  
X Ray Crystallography ◽  
Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

scholarly journals Chemical Elicitors Induce Rare Bioactive Secondary Metabolites in Deep-Sea Bacteria under Laboratory Conditions

Metabolites ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 107
Author(s):  
Rafael de Felício ◽  
Patricia Ballone ◽  
Cristina Freitas Bazzano ◽  
Luiz F. G. Alves ◽  
Renata Sigrist ◽  
...  
Keyword(s):  
Natural Products ◽  
Secondary Metabolites ◽  
Natural Product ◽  
Deep Sea ◽  
Chemical Space ◽  
Bacterial Genome ◽  
Vast Number ◽  
Bacterial Metabolites ◽  
Laboratory Conditions ◽  
Deep Sea Bacteria

Bacterial genome sequencing has revealed a vast number of novel biosynthetic gene clusters (BGC) with potential to produce bioactive natural products. However, the biosynthesis of secondary metabolites by bacteria is often silenced under laboratory conditions, limiting the controlled expression of natural products. Here we describe an integrated methodology for the construction and screening of an elicited and pre-fractionated library of marine bacteria. In this pilot study, chemical elicitors were evaluated to mimic the natural environment and to induce the expression of cryptic BGCs in deep-sea bacteria. By integrating high-resolution untargeted metabolomics with cheminformatics analyses, it was possible to visualize, mine, identify and map the chemical and biological space of the elicited bacterial metabolites. The results show that elicited bacterial metabolites correspond to ~45% of the compounds produced under laboratory conditions. In addition, the elicited chemical space is novel (~70% of the elicited compounds) or concentrated in the chemical space of drugs. Fractionation of the crude extracts further evidenced minor compounds (~90% of the collection) and the detection of biological activity. This pilot work pinpoints strategies for constructing and evaluating chemically diverse bacterial natural product libraries towards the identification of novel bacterial metabolites in natural product-based drug discovery pipelines.

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