Soluble cuticular wax composition and antimicrobial activity of the fruits of Chaenomeles species and an interspecific hybrid

Plants of the genus Chaenomeles Lindl. (Rosaceae) naturally grow in Southeast Asia and represent the richest resource of biologically active compounds with beneficial properties for humans. Plants of C. japonica (Thunb.) Lindl. and C. speciosa (Sweet) Nakai species, and interspecific hybrid C. × superba (Frahm) Rehder (C. japonica × C. speciosa, Superba group) have been successfully introduced in the steppe zone of Ukraine and bear fruits. In this study, we evaluated chemical composition of fruit cuticular waxes and antimicrobial activity of fruit extracts. The soluble waxes were characterized using gas chromatography-mass spectrometry (GC-MS), and 26–36 compounds, representing 91.7–96.6% of the total soluble cuticular waxes, were identified. Waxes of Chaenomeles fruits belonged to six classes, namely fatty acids, alcohols, aldehydes, esters, ethers and alkanes. Aldehydes 7-hexadecenal and heptacosanal, and alkanes hexatriacontane and tetrapentacontane were the main constituents in the soluble cuticular waxes of C. speciosa and C. × superba fruits, accounting for more than half of the total contents. However, alkane tetrapentacontane, alcohol 8,10-hexadecadien-1-ol and heptacosanal prevailed in C. japonica fruit waxes. Isopropanolic fruit extracts exhibited dose-dependent antimicrobial activity against four Gram-negative bacteria, five Gram-positive bacteria and one fungal strain in the disc diffusion assay. In general, extracts from the Chaenomeles fruits demonstrated higher activity against Gram+ bacteria than Gram- strains. The strongest inhibiting activity was shown against Staphylococcus epidermidis (by the fruit extracts of C. × superba and C. speciosa), Micrococcus lysodeikticus and Candida albicans (both by C. × superba fruit extract). Results of the study confirmed accumulation of the bioactive compounds in the fruit waxes of different Chaenomeles species and antimicrobial ability of Chaenomeles fruits as well. These findings revealed the bioactive compounds in fruit cuticular waxes and suggested health-promoting properties of introduced Chaenomeles species.

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The Search for Biologically Active Compounds in the Series of N-ethoxyethylpiperidine Derivatives

Eurasian Chemico-Technological Journal ◽

10.18321/ectj822 ◽

2019 ◽

Vol 21 (2) ◽

pp. 125

Author(s):

U.B. Issayeva ◽

G.S. Akhmetova ◽

U.M. Datkhayev ◽

M.T. Omyrzakov ◽

K.D. Praliyev ◽

...

Keyword(s):

Antimicrobial Activity ◽

Biologically Active ◽

Hydroxyl Group ◽

Diffusion Method ◽

Acylation Reaction ◽

Gram Positive Bacteria ◽

Cyclopropanecarboxylic Acid ◽

Yeast Fungus ◽

Acid Esters

With the aim to introduce fragment of cyclopropane and fragments of p-, m-, o-fluorophenyls into the structures of N-ethoxyethylpiperidines, acylation of oxime and phenylacetylenic alcohol of 1-(2-ethoxyethyl)-4-ketopiperidine by cyclopropanecarbonylchloride was carried out; on the basis of 1-(2-ethoxyethyl)-4-ethynyl-4-hydroxypiperidine (cascaine alcohol), acylation by 4-fluoro-, 3-fluoro-, 2-fluorobenzoylchlorides was carried out with formation of the corresponding piperidine containing hydrochlorides of cyclopropanecarboxylic acid esters and para-, meta-, ortho-fluorobenzoic esters. Acylation reaction on the hydroxyl group of compounds is carried out in absolute dioxane, the acylating agents are cyclopropanecarbonylchloride, p-, m-, o-fluorobenzoyl chlorides taken in excess. The obtained esters of cyclopropanecarboxylic and para-, meta-, ortho-fluorobenzoic acids are crystalline substances with a clear melting point, well soluble in water, ethanol, acetone. P-fluorobenzoates are obtained with better yields, m-fluorobenzoates occupy an intermediate position, and o-fluorobenzoates are formed with the lowest yields. The best yields of fluorobenzoates are obtained using dioxane as a solvent. Para-, meta-, ortho-fluorobenzoic esters of 1-(2-ethoxyethyl)-4-ethynyl-4-hydroxypiperidine coded A-4 – A-6 were studied for the presence of antimicrobial activity, the actions of these preparations were evaluated in vitro in relation to strains of gram-positive bacteria Staphylococcus aureus, Bacillus subtilis, gram-negative strains of Escheriсhia coli, Pseudomonas aeruginosa and to yeast fungus Сandida albicans by the diffusion method into agar (holes). Introduction of fluorine atom into the structure of cascaine lead to manifestation of antimicrobial activity.

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Synthesis and Evaluation of Antimicrobial and Cytotoxic Activity of Oxathiine-Fused Quinone-Thioglucoside Conjugates of Substituted 1,4-Naphthoquinones

Molecules ◽

10.3390/molecules25163577 ◽

2020 ◽

Vol 25 (16) ◽

pp. 3577

Author(s):

Yuri E. Sabutski ◽

Ekaterina S. Menchinskaya ◽

Ludmila S. Shevchenko ◽

Ekaterina A. Chingizova ◽

Artur R. Chingizov ◽

...

Keyword(s):

Antimicrobial Activity ◽

Cytotoxic Activity ◽

Antimicrobial Activities ◽

Biologically Active ◽

Hydroxyl Group ◽

Diffusion Method ◽

Gram Positive ◽

Gram Positive Bacteria ◽

High Cytotoxic Activity ◽

Derivatives Of

A series of new tetracyclic oxathiine-fused quinone-thioglycoside conjugates based on biologically active 1,4-naphthoquinones and 1-mercapto derivatives of per-O-acetyl d-glucose, d-galactose, d-xylose, and l-arabinose have been synthesized, characterized, and evaluated for their cytotoxic and antimicrobial activities. Six tetracyclic conjugates bearing a hydroxyl group in naphthoquinone core showed high cytotoxic activity with EC50 values in the range of 0.3 to 0.9 μM for various types of cancer and normal cells and no hemolytic activity up to 25 μM. The antimicrobial activity of conjugates was screened against Gram-positive bacteria (Staphylococcus aureus, Bacillus cereus), Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), and fungus Candida albicans by the agar diffusion method. The most effective juglone conjugates with d-xylose or l-arabinose moiety and hydroxyl group at C-7 position of naphthoquinone core at concentration 10 µg/well showed antimicrobial activity comparable with antibiotics vancomicin and gentamicin against Gram-positive bacteria strains. In liquid media, juglone-arabinosidic tetracycles showed highest activity with MIC 6.25 µM. Thus, a positive effect of heterocyclization with mercaptosugars on cytotoxic and antimicrobial activity for group of 1,4-naphthoquinones was shown.

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Lilium Philadelphicum Flower as a Novel Source of Antimicrobial Agents: A Study of Bioactivity, Phytochemical Analysis and Partial Identification of Antimicrobial Metabolites

10.20944/preprints202103.0203.v1 ◽

2021 ◽

Author(s):

Shefali Singh ◽

Vineeta Singh ◽

Alaa Alhazami ◽

B.N. Mishra ◽

Shafiul Haque ◽

...

Keyword(s):

Cell Viability ◽

Bioactive Compounds ◽

Bioactive Compound ◽

Biologically Active ◽

Gas Chromatography Mass Spectrometry ◽

Achromobacter Xylosoxidans ◽

Phytochemical Analysis ◽

Antimicrobial Potential ◽

Compound Concentration

The members of the Liliaceae family have been regarded as an excellent source of biologically active compounds. However, the work on antimicrobial potential and characterization of the bioactive fractions of Lilium philadelphicum flower is limited and needs to be explored. The present study reports the antimicrobial potential, anti-inflammatory and anticancer potential of the bioactive fraction extracted from the flower of L. philadelphicum (Red Lily) and characterization of these bioactive compounds. The antimicrobial activity was tested against nine different Gram-positive and Gram-negative bacterial strains. The minimum inhibitory concentration (MIC) values of methanolic extract of L. philadelphicum flower against Acinetobacter bouvetii, Achromobacter xylosoxidans, Bacillus subtilis MTCC 121, Candida albicans MTCC 183, Klebsiella pneumoniae MTCC 3384, and Salmonella typhi MTCC 537 were 25, 50, 12.5, 50, 100 and 50 μg mL-1, respectively. The phytochemical analysis of the extract reveals the presence of phenols, flavonoids, tannins, terpenoids, glycosides, coumarins, and quinones. The cytotoxicity of the partially purified compound against the HepG2 cell line in MTT assay demonstrates up to 90% cell viability with a bioactive compound concentration of 50 μg/ml. However, with the increase in bioactive compound concentration up to 1000 μg/ml results into nearly 80% cell viability, just a minor decline in cell viability suggests the importance of bioactive compounds for suitable therapeutic applications. Spectroscopic studies of the bioactive compound by UV-Visible spectroscopy, FT-Infra Red spectroscopy, Gas Chromatography-Mass Spectrometry (GCMS) as well as its phytochemical analysis suggests the presence of terpenoids moiety, responsible for the antimicrobial property of L. philadelphicum flower.

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Chemical composition and antimicrobial activity of extracts from thyme and rosemary against Staphylococcus aureus and Candida albicans

BioResources ◽

10.15376/biores.15.4.9656-9671 ◽

2020 ◽

Vol 15 (4) ◽

pp. 9656-9671

Author(s):

Akram Sabzikar ◽

Seyyed Khalil Hosseinihashemi ◽

Younes Shirmohammadli ◽

Abbas Jalaligoldeh

Keyword(s):

Staphylococcus Aureus ◽

Antimicrobial Activity ◽

Candida Albicans ◽

Chemical Composition ◽

Inhibition Zone ◽

Gas Chromatography Mass Spectrometry ◽

Diffusion Method ◽

Rosemary Extract ◽

Gram Positive Bacteria ◽

Main Components

Different concentrations of ethanolic extracts of thyme (Zataria multiflora) and rosemary (Rosmarinus officinalis) were evaluated to determine their antimicrobial activity using the agar-well diffusion method. The values of inhibition zone diameter (IZD) for Candida albicans fungus and Staphylococcus aureus Gram-positive bacteria were determined. The bioactivities of two various extracts were studied, and the chemical composition of the extracts were identified using gas chromatography-mass spectrometry (GC-MS) technique. The results of the test showed that at concentrations of 10% and 40% thyme extract, the values of IZD were 12.5 mm and 23.3 mm, respectively, against the growth of S. aureus, which were higher than C. albicans (7.0 mm and 22.5 mm, respectively). The rosemary extract at concentrations of 20% and 60% showed lower antibacterial activity against S. aureus (4.7 mm and 8.7 mm IZD, respectively) and lower antifungal activity against C. albicans (12.2 mm and 1.7 mm IZD, respectively). At a concentration of 40% thyme extract, the highest antibacterial (23.3 mm IZD) and antifungal (22.5 mm IZD) activities were observed. The GC/MS analysis showed that carvacrol (52.3%), linalool L (16%), and thymol (9.6%) were the main components of thyme extract, while in the rosemary extract β-amyrone (18.0%), verbenone (8.0%), and 1,8-cineole (7.26%) were the major constituents.

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Antimicrobial Activity of Ultrasonic Extracts of Two Chemotypes of Thymus serpyllum L. of Central Kazakhstan and their Polyphenolic Profiles

Open Access Macedonian Journal of Medical Sciences ◽

10.3889/oamjms.2021.5520 ◽

2021 ◽

Vol 9 (A) ◽

pp. 61-67

Author(s):

Svetlana Ivasenko ◽

Perizat Orazbayeva ◽

Krystyna Skalicka–Wozniak ◽

Agnieszka Ludwiczuk ◽

Alexandr Marchenko ◽

...

Keyword(s):

Antimicrobial Activity ◽

Wide Spectrum ◽

Biological Properties ◽

Climatic Conditions ◽

Biologically Active ◽

Gram Positive Bacteria ◽

Quantitative Content ◽

Two Samples ◽

Thymus Serpyllum ◽

Bacteria And Fungi

BACKGROUND: The medicinal plant of Thymus serpyllum L. in nature, depending on the geographical region, climatic conditions, and growing environment, is represented with some chemotypes. Composition and quantitative content of the basic groups of the biologically active substances can be differed, and thus their biological properties are also various. AIM: The aim of the study was to determine possibility of the using the ultrasonic extracts of two chemotypes of T. serpyllum L. of Central Kazakhstan as an antimicrobial agent against test strains of microorganisms. MATERIALS AND METHODS: Two samples of T. serpyllum were extracted with 70% ethanol using ultrasound. The polyphenol content of the ultrasound extracts was determined using the LC-ultraviolet-ESI- tandem mass spectrometry technique. A study of an antimicrobial activity of the ultrasonic extracts was performed with eight strains of Gram-positive bacteria, six strains of Gram-negative bacteria, and four cultures of fungi. RESULTS: The ultrasonic extracts of two chemotypes of T. serpyllum L. are similar in composition of phenolic compounds but differ in a quantitative content of phenolic acids and flavonoids, except for a rosmarinic acid. The ultrasonic extracts have a wide spectrum of antimicrobial activity, exhibit the bactericidal or bacteriostatic activity against all tested bacteria and fungi at a concentration of 0.0625–20 mg/ml, but differ in their strength of action against test strains of microorganisms. CONCLUSION: The ultrasonic extracts of two chemotypes of T. serpyllum L. of Central Kazakhstan can be considered as a potential drug with a wide spectrum of antimicrobial activity. The results of chromatographic analysis will be used for standardization of a drug.

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Synthesis and Antimicrobial Activity of Burkholderia-Related 4-Hydroxy-3-Methyl-2-Alkenylquinolones (HMAQs) and Their N-Oxide Counterparts

10.26434/chemrxiv.11859144 ◽

2020 ◽

Author(s):

Marianne Piochon ◽

Pauline M. L. Coulon ◽

Armand Caulet ◽

Marie-Christine Groleau ◽

Eric Déziel ◽

...

Keyword(s):

Antimicrobial Activity ◽

Biologically Active ◽

Specific Class ◽

Gram Positive ◽

Carbonate Group ◽

Gram Positive Bacteria ◽

Alkenyl Chain ◽

Optimized Conditions ◽

Burkholderia Ambifaria

ABSTRACT: The Burkholderia genus offers a promising potential in medicine because of the diversity of biologically active natural products encoded in its genome. Some pathogenic Burkholderia spp. biosynthesize a specific class of antimicrobial 2-alkyl-4(1H)-quinolones, i.e., 4-hydroxy-3-methyl-2-alkenylquinolones (HMAQs) and their N-oxide derivatives (HMAQNOs). Herein, we report the synthesis of a series of six HMAQs and HMAQNOs featuring a trans-∆<sup>2</sup> double bond at the C2-alkyl chain. The quinolone scaffold was obtained via the Conrad-Limpach approach while the (E)-2-alkenyl chain was inserted through Suzuki-Miyaura cross-coupling under microwave radiation without noticeable isomerization according to the optimized conditions. Subsequent oxidation of enolate-protected HMAQs cleanly led to the formation of HMAQNOs following cleavage of the ethyl carbonate group. Synthetic HMAQs and HMAQNOs were in vitro evaluated for their antimicrobial activity against different Gram-negative and Gram-positive bacteria as well as against fungi and yeasts. The biological results support and extend the potential of HMAQs and HMAQNOs as antimicrobials, especially against Gram-positive bacteria. We also confirm the involvement of HMAQs in the autoregulation of the Hmq system in Burkholderia ambifaria.

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Biologically active binaphthol-scaffolded imidazolium salts

MedChemComm ◽

10.1039/c3md00293d ◽

2014 ◽

Vol 5 (4) ◽

pp. 436-440 ◽

Cited By ~ 20

Author(s):

Marc Vidal ◽

Claude-Rosny Elie ◽

Shirley Campbell ◽

Audrey Claing ◽

Andreea R. Schmitzer

Keyword(s):

Antimicrobial Activity ◽

Lipid Membrane ◽

Biologically Active ◽

Imidazolium Salts ◽

Gram Positive ◽

Gram Positive Bacteria

This work describes the antimicrobial activity and selectivity for Gram-positive bacteria of imidazolium-functionalized binols, as a result of their insertion into the lipid membrane and alteration of its permeability.

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Health-Promoting Capacities of In Vitro and Cultivated Goji (Lycium chinense Mill.) Fruit and Leaves; Polyphenols, Antimicrobial Activity, Macro- and Microelements and Heavy Metals

Molecules ◽

10.3390/molecules25225314 ◽

2020 ◽

Vol 25 (22) ◽

pp. 5314

Author(s):

Arleta Kruczek ◽

Marcelina Krupa-Małkiewicz ◽

Sabina Lachowicz ◽

Jan Oszmiański ◽

Ireneusz Ochmian

Keyword(s):

Heavy Metals ◽

Antimicrobial Activity ◽

Nutritional Value ◽

Positive Impact ◽

The Public ◽

Gram Positive Bacteria ◽

Health Promoting ◽

Goji Berries ◽

Daily Allowance

There is a growing interest among the public in fruit with a positive impact on human health. Two goji berry cultivars (‘No. 1’ and ‘New Big’) were propagated in vitro, grown in an orchard and then evaluated for macro- and microelements and harmful heavy metals (i.e., Pb, Ni, and Cd). The leaves and fruit were also assessed for nutritional value, polyphenols and the antimicrobial activity of the leaves. ‘New Big’ was characterized by a higher content of macro elements in the leaves (in vitro and orchard) and a higher content of microelements in the fruit. The harmful substances content was below the minimum value. Furthermore, neither the fruit nor the leaves contained cadmium. This study also indicated that leaves had a higher content of polyphenols compared to the fruit. The fruits were characterized by their health-promoting capacities, while the leaves were characterized by their antibacterial activity. Among the Gram-positive bacteria, the most sensitive strain was Bacillus subtilis, and among the Gram-negative bacteria, it was Proteus vulgaris. Taking into consideration the Recommended Daily Allowance (RDA) for minerals, goji berries can be declared to be a source of Cu, Fe, Mn, Zn and P.

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Chemical profile and antimicrobial activity of extractable compounds of Betula litwinowii (Betulaceae) buds

Open Chemistry ◽

10.1515/chem-2015-0019 ◽

2015 ◽

Vol 13 (1) ◽

Cited By ~ 8

Author(s):

Valery A. Isidorov ◽

Róża Bagan ◽

Lech Szczepaniak ◽

Izabela Swiecicka

Keyword(s):

Antimicrobial Activity ◽

Folk Medicine ◽

Biologically Active ◽

Chemical Profile ◽

Active Components ◽

Volatile Elements ◽

Gram Positive Bacteria ◽

History Of ◽

Extractable Compounds

AbstractIn spite of the long history of therapeutic use of buds from different birch species in folk medicine the existing information on their chemical composition is insufficient. The main goal was to develop a method for GC-MS determination of the chemical profile of birch buds as well as their antimicrobial activity. 150 substances of different classes were identified in Betula litwinowii buds. The volatile elements of the buds were mainly represented by sesquiterpene compounds. Ether extracts also contained other biologically active components such as flavonoids and triterpenoids. However, a particular feature of this fraction was the high content of sesquiterpene phenylpropenoids, including esters of ferulic and caffeic acids with caryophyllene-type alcohols that had not been previously found in any biological samples. Apart from carbohydrates, a series of free amino acids were detected in methanol extracts. The antimicrobial activity of the ether extracts of the buds was observed against all of the microorganisms tested, with MIC values from 0.04 to 0.08 mg mL-1 for Gram-positive bacteria and Candida albicans. However, their inhibitory activities against tested Gram-negative bacteria were rather occasional.

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The antimicrobial activity of polyfloral honey and its awareness among urban consumers in Slovakia

Potravinarstvo Slovak Journal of Food Sciences ◽

10.5219/1621 ◽

2021 ◽

Vol 15 ◽

pp. 467-474

Author(s):

Peter Šedík ◽

Kristína Predanócyová ◽

Elena Horská ◽

Miroslava Kačániová

Keyword(s):

Antimicrobial Activity ◽

Consumer Research ◽

Urban Areas ◽

Biologically Active ◽

Maximum Temperature ◽

Winter Period ◽

Gram Negative Bacteria ◽

Gram Positive Bacteria ◽

Equality Of Means ◽

Very High

The current interdisciplinary research studies the antimicrobial activity of selected polyfloral kinds of honey (n = 30) against three microorganisms (gram-positive bacteria Enterococcus faecalis, gram-negative bacteria Salmonella enterica, and one yeast Candida krusei) as well as investigates consumer behavior and awareness towards honey healing properties. Consumer research involved 617 honey consumers living in urban areas. T-test for Equality of means, non-parametric tests, and descriptive statistics were applied. Results showed that antimicrobial activity was found in all honey samples with a concentration of 50%. Nevertheless, better activity was obtained in honey samples from urban beekeepers compared to samples from retail stores. Results of consumer research showed that honey is mostly used as food (sweetener in beverages, ingredient in the recipe, or direct consumption) and as medicine mainly during the winter period. The consumer awareness towards honey healing effects was very high (97%), however, 1/3 of respondents were not able to list any specific examples, and only 11 % mentioned antibacterial activity. Furthermore, more than 70% of respondents did not know to explain the term “medical honey” and more than 50% of respondents are not aware of the maximum temperature used for heating honey without decreasing its biologically active compounds.

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