Ent-homocyclopiamine B, a Prenylated Indole Alkaloid of Biogenetic Interest from the Endophytic Fungus Penicillium concentricum

Ent-homocyclopiamine B (1), a new prenylated indole alkaloid bearing an alicyclic nitro group along with 2-methylbutane-1,2,4-triol (2) were isolated from an endophytic fungus Penicillium concentricum of the liverwort Trichocolea tomentella (Trichocoleaceae). The structure of 1 was elucidated through extensive spectroscopic analyses and comparison with data reported for a structurally related nitro-bearing Penicillium metabolite, clopiamine C (3), which contain an indolizidine ring instead of the quinolizine ring in 1. The new compound, ent-homocyclopiamine B, exhibited slight growth inhibition against Gram-positive bacteria. Based on the reported biosynthesis of related compounds and the isolation of the mevalonic acid derived compound 2-methyl-1,2,4-butanetriol (2), we proposed that ent-homocylopiamine B (1) was biosynthesized from lysine and prenyl group-producing mevalonic pathway.

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In Vitro Antitumor Activity of Endophytic and Rhizosphere Gram-Positive Bacteria from Ibervillea sonorae (S. Watson) Greene against L5178Y-R Lymphoma Cells

International Journal of Environmental Research and Public Health ◽

10.3390/ijerph19020894 ◽

2022 ◽

Vol 19 (2) ◽

pp. 894

Author(s):

Ricardo Romero-Arguelles ◽

César Iván Romo-Sáenz ◽

Karla Morán-Santibáñez ◽

Patricia Tamez-Guerra ◽

Ramiro Quintanilla-Licea ◽

...

Keyword(s):

Antitumor Activity ◽

Growth Inhibition ◽

Mononuclear Cells ◽

Colorimetric Assay ◽

Human Peripheral Blood ◽

Antitumor Effects ◽

Lymphoma Cells ◽

Gram Positive ◽

Peripheral Blood Mononuclear ◽

Gram Positive Bacteria

Plant-associated microorganisms represent a potential source of new antitumor compounds. The aim of the present study was to isolate endophytic and rhizosphere Gram-positive bacteria from Ibervillea sonorae and produce extracts with antitumor activity. Methanol and ethyl acetate extracts were obtained from 28 d bacterial fermentation, after which murine L5178Y-R lymphoma cells growth inhibition was evaluated at concentrations ranging from 15.62 µg/mL to 500 µg/mL by the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide reduction colorimetric assay. IC50 and the selectivity index (SI) were calculated and compared with healthy control human peripheral blood mononuclear cells (PBMC). Identification of the isolated strains was performed using the 16S ribosomal gene and by MALDI-TOF MS mass spectrometry. The endophytic and rhizosphere bacterial extracts from strains ISE-B22, ISE-B26, ISE-B27, ISS-A01, ISS-A06, and ISS-A16 showed significant (p < 0.05) L5178Y-R cell growth inhibition, compared with an untreated control. The rhizosphere Micromonospora echinospora isolate ISS-A16 showed the highest (90.48%) percentage of lymphoma cells growth inhibition and SI (19.1) for PBMC, whereas the Bacillus subtilis ISE-B26 isolate caused significant (p < 0.01) growth inhibition (84.32%) and a SI of 5.2. Taken together, results of the present study evidenced antitumor effects by I. sonorae endophytic and rhizosphere bacteria culture extracts. Further research will involve the elucidation of the compounds that exert the antitumor activity and their evaluation in pre-clinical studies.

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Antimicrobial activities of Antarctic sponges

Antarctic Science ◽

10.1017/s0954102092000270 ◽

1992 ◽

Vol 4 (2) ◽

pp. 179-183 ◽

Cited By ~ 20

Author(s):

J.B. McClintock ◽

J.J. Gauthier

Keyword(s):

Antimicrobial Activity ◽

Growth Inhibition ◽

Antimicrobial Activities ◽

Marine Sponges ◽

Gram Negative Bacteria ◽

Gram Positive ◽

Strong Activity ◽

Gram Negative ◽

Gram Positive Bacteria ◽

Antarctic Marine

Methanol-toluene extracts of 17 common Antarctic marine sponges collected from shallow waters in McMurdo Sound in October–December 1989 were tested for suppression of growth of bacteria (gram-positive and negative), yeasts and fungi. Weak to moderate levels of antimicrobial activity occurred in all sponges. Antimicrobial activity was more common when gram-negative bacteria were exposed to sponge extracts; 47% of the sponge extracts caused growth inhibition in one or more gram-positive bacteria, while 100% of the extracts caused growth inhibition in gram-negative bacteria. Particularly strong activity was observed against two species of gram-positive bacteria exposed to extracts of the sponge Latrunculia apicalis and against one strain of gram-negative bacterium exposed to extracts of the sponge Haliclona sp. Antimicrobial responses against yeasts and fungi were generally non-existent or weak, with the exception of the yeast Candida tropicalis, which was strongly inhibited by extracts of the sponges Homaxonella balfourensis, Dendrilla membranosa, Kirkpatrickia variolosa, Gellius benedeni, Cinachyra antarctica and Scolymastia joubinia. Antimicrobial activity in these polar sponges is widespread but generally weaker than that found in temperate and tropical sponges.

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Barakacin: A Thiazolyl-indole Alkaloid Isolated from a Ruminal Pseudomonas sp.

Zeitschrift für Naturforschung B ◽

10.5560/znb.2011-0277 ◽

2012 ◽

Vol 67 (5) ◽

pp. 417-420 ◽

Cited By ~ 11

Author(s):

Imene Zendah ◽

Khaled A. Shaaban ◽

Elisabeth Helmke ◽

Armin Maier ◽

Heinz H. Fiebig ◽

...

Keyword(s):

Pseudomonas Aeruginosa ◽

Carboxylic Acid ◽

Structure Elucidation ◽

Biological Activities ◽

Indole Alkaloid ◽

Ecological Niches ◽

Pseudomonas Sp ◽

Ruminal Bacterium ◽

Spectroscopic Analyses ◽

Related Compounds

A new thiazolyl-indole alkaloid, barakacin (1), has been isolated from the ruminal bacterium Pseudomonas aeruginosa strain ZIO. On the basis of detailed spectroscopic analyses and comparison with the data of related compounds, its structure has been determined as 2-{4-[bis-(1H-indol-3- yl)-methyl]-thiazol-2-yl}-phenol. In addition, the known compounds phenazine-1-carboxylic acid, 3-(hydroxyacetyl)-indole, indole-3-carbaldehyde, and glycolipid A were isolated. The discovery of compounds with a new skeleton emphasizes the importance for exploring new ecological niches like the rumen of bovines for the detection of new natural products. This paper describes the fermentation, isolation, structure elucidation and biological activities of compound 1.

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New Metabolites from Endophytic Fungus Chaetomium globosum CDW7

Molecules ◽

10.3390/molecules23112873 ◽

2018 ◽

Vol 23 (11) ◽

pp. 2873 ◽

Cited By ~ 9

Author(s):

Wei Yan ◽

Ling-Ling Cao ◽

Yang-Yang Zhang ◽

Ran Zhao ◽

Shuang-Shuang Zhao ◽

...

Keyword(s):

Endophytic Fungus ◽

Protective Efficacy ◽

Indole Alkaloid ◽

Chaetomium Globosum ◽

Ionization Mass ◽

In Vivo Test ◽

Sclerotinia Rot ◽

Spectroscopic Analyses ◽

New Metabolites

Five metabolites including two new ones, prochaetoviridin A (1) and chaetoindolin A (2), were isolated from the endophytic fungus Chaetomium globosum CDW7. Compounds 1 and 2 were characterized as an isocoumarin and an indole alkaloid derivative, respectively, with their structures elucidated by comprehensive spectroscopic analyses including high-resolution electrospray ionization mass spectrometry (HR-ESI-MS), NMR, and circular dichroism (CD) comparison. Compounds 3–5 were identified as chaetoviridin A, chaetoglobosin R, and chaetoglobosin T, respectively. Chaetoviridin A (3) exhibited antifungal activity against Sclerotinia sclerotiorum with an EC50 value of 1.97 μg/mL. In vivo test showed that 3 displayed a protective efficacy of 64.3% against rape Sclerotinia rot at the dosage of 200 μg/mL, comparable to that of carbendazim (69.2%).

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Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity

Marine Drugs ◽

10.3390/md16080289 ◽

2018 ◽

Vol 16 (8) ◽

pp. 289 ◽

Cited By ~ 7

Author(s):

Decha Kumla ◽

José Pereira ◽

Tida Dethoup ◽

Luis Gales ◽

Joana Freitas-Silva ◽

...

Keyword(s):

Antibacterial Activity ◽

Growth Inhibition ◽

Marine Sponge ◽

Multidrug Resistant ◽

Gram Positive ◽

Gram Negative ◽

Chromone Derivatives ◽

Gram Positive Bacteria ◽

Resistant Strains

A previously unreported chromene derivative, 1-hydroxy-12-methoxycitromycin (1c), and four previously undescribed chromone derivatives, including pyanochromone (3b), spirofuranochromone (4), 7-hydroxy-6-methoxy-4-oxo-3-[(1E)-3-oxobut-1-en-1-yl]-4H-chromene-5-carboxylic acid (5), a pyranochromone dimer (6) were isolated, together with thirteen known compounds: β-sitostenone, ergosterol 5,8-endoperoxide, citromycin (1a), 12-methoxycitromycin (1b), myxotrichin D (1d), 12-methoxycitromycetin (1e), anhydrofulvic acid (2a), myxotrichin C (2b), penialidin D (2c), penialidin F (3a), SPF-3059-30 (7), GKK1032B (8) and secalonic acid A (9), from cultures of the marine sponge- associated fungus Penicillium erubescens KUFA0220. Compounds 1a–e, 2a, 3a, 4, 7–9, were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 8 exhibited an in vitro growth inhibition of all Gram-positive bacteria whereas 9 showed growth inhibition of methicillin-resistant Staphyllococus aureus (MRSA). None of the compounds were active against Gram-negative bacteria tested.

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Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

Beilstein Journal of Organic Chemistry ◽

10.3762/bjoc.16.177 ◽

2020 ◽

Vol 16 ◽

pp. 2100-2107

Author(s):

Ken-ichi Nakashima ◽

Junko Tomida ◽

Tomoe Tsuboi ◽

Yoshiaki Kawamura ◽

Makoto Inoue

Keyword(s):

Antibacterial Activity ◽

Endophytic Fungus ◽

Spectroscopic Analysis ◽

Gram Positive ◽

Electronic Circular Dichroism ◽

Gram Positive Bacteria ◽

Circular Dichroism Data ◽

Circular Dichroïsm ◽

Weak Antibacterial Activity ◽

Modified Mosher’S Method

Two new azaphilones, namely muyocopronones A (1) and B (2), were isolated from the cultures of an endophytic fungus Muyocopron laterale ECN279. Their structures were elucidated by extensive spectroscopic analysis. Their absolute configurations were determined using the modified Mosher’s method and through comparisons of experimental and calculated electronic circular dichroism data. In addition, muyocopronone B (2) was found to exhibit a weak antibacterial activity against some Gram-positive bacteria.

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Muscodor sp. IBRL OS-94, A Promising Endophytic Fungus of Ocimum sanctum with Antimicrobial Activity

Pharmaceutical Sciences ◽

10.34172/ps.2020.79 ◽

2020 ◽

Vol 27 (2) ◽

pp. 268-280

Author(s):

Mohd Taufiq Mat Jalil ◽

Nabila Husna Hairudin ◽

Darah Ibrahim

Keyword(s):

Antimicrobial Activity ◽

Endophytic Fungus ◽

Disk Diffusion ◽

Ocimum Sanctum ◽

Gram Positive ◽

Gram Negative ◽

Fungal Extract ◽

Gram Positive Bacteria ◽

Agar Plug ◽

Diffusion Assay

Background: An endophytic fungus, Muscodor sp. IBRL OS-94 isolated from the leaf of Ocimum sanctum was believed to possess significant antimicrobial activity and several assays were carried out to evaluate its pharmaceutical potential. Methods: Agar plug diffusion and the disk diffusion assays were performed to evaluate the antimicrobial activity of the fungal extract. Also, the broth microdilution assay was done to investigate the minimum inhibitory concentration (MIC) of the fungal extract. Meanwhile, the scanning electron microscope (SEM) was employed to observe the structural degeneration of the microbial cells treated to the extract. Results: The results revealed that fungal isolate showed favorable antimicrobial activity through agar plug diffusion assay and the disk diffusion assay demonstrated that most of the test microorganisms were susceptible to extracellular extract compared to extracellular extract. As for the MIC and MLC values, the extracellular fungal extract exerted a bactericidal/fungicidal effect against all five Gram-positive bacteria, four Gram-negative bacteria, one yeast, and none of the test fungi. Meanwhile, the intracellular fungal extract exhibited bactericidal/fungicidal activity against three Gram-positive bacteria, one Gram-negative bacterium, and one yeast. The structural degeneration study via SEM revealed that various cell abnormalities including severe damage to the cell wall which led to microbial cell death. Conclusion: The present study suggests the fungal extract from Muscodor sp. IBRLOS-94 as an antimicrobial agent.

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Influence of Cell Wall Composition on the Fossilisation of Bacteria and the Implications for the Search for Early Life Forms

International Astronomical Union Colloquium ◽

10.1017/s0252921100015025 ◽

1997 ◽

Vol 161 ◽

pp. 491-504 ◽

Cited By ~ 3

Author(s):

Frances Westall

Keyword(s):

Cell Wall ◽

Life Forms ◽

Cation Binding ◽

Positive Bacterium ◽

Gram Positive ◽

Gram Positive Bacteria ◽

Transmission Electron ◽

Hydrothermal Sediments ◽

Identification Of Bacteria ◽

The Difference

AbstractThe oldest cell-like structures on Earth are preserved in silicified lagoonal, shallow sea or hydrothermal sediments, such as some Archean formations in Western Australia and South Africa. Previous studies concentrated on the search for organic fossils in Archean rocks. Observations of silicified bacteria (as silica minerals) are scarce for both the Precambrian and the Phanerozoic, but reports of mineral bacteria finds, in general, are increasing. The problems associated with the identification of authentic fossil bacteria and, if possible, closer identification of bacteria type can, in part, be overcome by experimental fossilisation studies. These have shown that not all bacteria fossilise in the same way and, indeed, some seem to be very resistent to fossilisation. This paper deals with a transmission electron microscope investigation of the silicification of four species of bacteria commonly found in the environment. The Gram positiveBacillus laterosporusand its spore produced a robust, durable crust upon silicification, whereas the Gram negativePseudomonas fluorescens, Ps. vesicularis, andPs. acidovoranspresented delicately preserved walls. The greater amount of peptidoglycan, containing abundant metal cation binding sites, in the cell wall of the Gram positive bacterium, probably accounts for the difference in the mode of fossilisation. The Gram positive bacteria are, therefore, probably most likely to be preserved in the terrestrial and extraterrestrial rock record.

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Microanatomy of the Periplasm of Bacillus Licheniformis

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100065365 ◽

1971 ◽

Vol 29 ◽

pp. 262-263

Author(s):

B.K. Ghosh

Keyword(s):

Cell Wall ◽

Plasma Membrane ◽

Bacillus Licheniformis ◽

External Environment ◽

Permeability Barrier ◽

Periplasmic Space ◽

Modified Technique ◽

Gram Positive ◽

Gram Negative ◽

Gram Positive Bacteria

Periplasm of bacteria is the space outside the permeability barrier of plasma membrane but enclosed by the cell wall. The contents of this special milieu exterior could be regulated by the plasma membrane from the internal, and by the cell wall from the external environment of the cell. Unlike the gram-negative organism, the presence of this space in gram-positive bacteria is still controversial because it cannot be clearly demonstrated. We have shown the importance of some periplasmic bodies in the secretion of penicillinase from Bacillus licheniformis.In negatively stained specimens prepared by a modified technique (Figs. 1 and 2), periplasmic space (PS) contained two kinds of structures: (i) fibrils (F, 100 Å) running perpendicular to the cell wall from the protoplast and (ii) an array of vesicles of various sizes (V), which seem to have evaginated from the protoplast.

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Rapid demonstration of septic or infectious arthritis due to Gram-negative bacteria

Proceedings, annual meeting, Electron Microscopy Society of America ◽

10.1017/s0424820100123830 ◽

1992 ◽

Vol 50 (1) ◽

pp. 686-687

Author(s):

Jacob S. Hanker ◽

Paul R. Gross ◽

Beverly L. Giammara

Keyword(s):

Chronic Arthritis ◽

Blood Cultures ◽

Gram Negative Bacteria ◽

Infectious Arthritis ◽

Bacterial Arthritis ◽

Gram Positive ◽

Gram Negative ◽

Gram Positive Bacteria

Blood cultures are positive in approximately only 50 per cent of the patients with nongonococcal bacterial infectious arthritis and about 20 per cent of those with gonococcal arthritis. But the concept that gram-negative bacteria could be involved even in chronic arthritis is well-supported. Gram stains are more definitive in staphylococcal arthritis caused by gram-positive bacteria than in bacterial arthritis due to gram-negative bacteria. In the latter situation where gram-negative bacilli are the problem, Gram stains are helpful for 50% of the patients; they are only helpful for 25% of the patients, however, where gram-negative gonococci are the problem. In arthritis due to gram-positive Staphylococci. Gramstained smears are positive for 75% of the patients.

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