Influence of Chemical Modifications of Polyhydroxyalkanoate-Derived Fatty Acids on Their Antimicrobial Properties

Snoch, Wojciech; Stępień, Karolina; Prajsnar, Justyna; Staroń, Jakub; Szaleniec, Maciej; Guzik, Maciej

doi:10.3390/catal9060510

Cited by 13 publications

(19 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Being precursors of prostaglandins, lipoxin (peak 62; m/z 353.2317, C 20 H 33 O 5 + ), oxolipoxin (peak 66; m/z 351.2159, C 20 H 31 O 5 + ), linolenic acid (peak 89; m/z 279.2332, C 18 H 31 O 2 + ) and its methyl ester (peak 98; m/z 293.2487, C 19 H 33 O 2 + ) exhibited anti-inflammatory effects [ 56 ]. Moreover, some hydroxylated fatty acids were present as major peaks and showed additional water molecule loss, aside from their cytotoxic and antimicrobial capacity [ 57 ]. For example, hydroxylinolenic acid (293.215, C 18 H 29 O 3 − ) and hydroxyolinoleic acid (295.2303, C 18 H 31 O 3 − ) revealed 2 amu mass differences attributed to the extra double bond with fragment ions at m/z 275 and 277, respectively due to the subsequent loss of one water molecule.…”

Section: Resultsmentioning

confidence: 99%

Chemical Profile of Launaea nudicaulis Ethanolic Extract and Its Antidiabetic Effect in Streptozotocin-Induced Rats

et al. 2021

View full text Add to dashboard Cite

Launaea nudicaulis is used in folk medicine worldwide to treat several diseases. The present study aimed to assess the antidiabetic activity of L. nudicaulis ethanolic extract and its effect on diabetic complications in streptozotocin-induced hyperglycemic rats. The extract was orally administrated at 250 and 500 mg/kg/day for 5-weeks and compared to glibenclamide as a reference drug at a dose of 5 mg/kg/day. Administration of the extract exhibited a potential hypoglycemic effect manifested by a significant depletion of serum blood glucose concurrent with a significant elevation in serum insulin secretion. After 5-weeks, extract at 250 and 500 mg/kg/day decreased blood glucose levels by about 53.8 and 68.1%, respectively, compared to the initial values (p ≤ 0.05). The extract at the two dosages prevented weight loss of rats from the 2nd week till the end of the experiment, compared to diabetic control rats. The extract further exhibited marked improvement in diabetic complications including liver, kidney and testis performance, oxidative stress, and relative weight of vital organs, with respect to diabetic control. Histopathological examinations confirmed the previous biochemical analysis, where the extract showed a protective effect on the pancreas, liver, kidney, and testis that degenerated in diabetic control rats. To characterize extract composition, UPLC-ESI–qTOF-MS identified 85 chromatographic peaks belonging to flavonoids, phenolics, acyl glycerols, nitrogenous compounds, and fatty acids, with four novel phenolics reported. The potential anti-diabetic effect warrants its inclusion in further studies and or isolation of the main bioactive agent(s).

show abstract

Section: Resultsmentioning

confidence: 99%

Chemical Profile of Launaea nudicaulis Ethanolic Extract and Its Antidiabetic Effect in Streptozotocin-Induced Rats

et al. 2021

View full text Add to dashboard Cite

show abstract

“…The hydroxylated acid methyl esters were analyzed by gas chromatography. Modification of the resultant methyl esters of monomers was conducted as described previously [29]. The obtained monomers were converted into their acidic forms using Candida antarctica lipase B under aqueous conditions to obtain sodium salts.…”

Section: Preparation Of Unmodified and Modified Polyhydroxynonanoate Monomersmentioning

confidence: 99%

“…PHAs can serve as material for manufacturing of nontoxic implants and other medical devices. They also are often used as media for drug delivery upon implantation [28][29][30]. To date, more than 150 different (R)-3-hydroxyacids have been reported, thus creating endless possibilities for further modifications [31].…”

Section: Introductionmentioning

confidence: 99%

“…The first one enables the synthesis of a wide range of SFAEs, the latter, on the other hand, enables the introduction of various moieties into the SFAE molecule. Recently, we have reported routes towards synthesis of (R)-3-hydroxyacidbased glucose esters with fluorine modified analogues [29]. Here, we expanded the glucose esters library with galactose and lactose SFAE versions and tested the whole collection of compounds against human melanoma and prostate cancer cells in vitro.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

In Search of Effective Anticancer Agents—Novel Sugar Esters Based on Polyhydroxyalkanoate Monomers

Snoch

Wnuk

Witko

et al. 2021

IJMS

Self Cite

View full text Add to dashboard Cite

Cancer is one of the deadliest illness globally. Searching for new solutions in cancer treatments is essential because commonly used mixed, targeted and personalized therapies are sometimes not sufficient or are too expensive for common patients. Sugar fatty acid esters (SFAEs) are already well-known as promising candidates for an alternative medical tool. The manuscript brings the reader closer to methods of obtaining various SFAEs using combined biological, chemical and enzymatic methods. It presents how modification of SFAE’s hydrophobic chains can influence their cytotoxicity against human skin melanoma and prostate cancer cell lines. The compound’s cytotoxicity was determined by an MTT assay, which followed an assessment of SFAEs’ potential metastatic properties in concentrations below IC50 values. Despite relatively high IC50 values (63.3–1737.6 μM) of the newly synthesized SFAE, they can compete with other sugar esters already described in the literature. The chosen bioactives caused low polymerization of microtubules and the depolymerization of actin filaments in nontoxic levels, which suggest an apoptotic rather than metastatic process. Altogether, cancer cells showed no propensity for metastasis after treating them with SFAE. They confirmed that lactose-based compounds seem the most promising surfactants among tested sugar esters. This manuscript creates a benchmark for creation of novel anticancer agents based on 3-hydroxylated fatty acids of bacterial origin.

show abstract

“…The identities of quinic acid, tannic acid, apigenin and gallic FULL PAPER Phenolic compounds with less-complex structures possess antimicrobial activities and play essential roles in killing antibiotic-resistant pathogens. Snoch et al (2019) suggested phenylvaleric acid, which is one of the phenolic acids, has a strong antibacterial effect towards S. aureus, C. albicans and E. coli. Quinic acid also has strong antibacterial properties where it can easily attack the intracellular cell of bacteria.…”

Section: Presence Of Phenolic Constituent In Sugarcane Molasses Extractmentioning

confidence: 99%

Evaluation of phenolic constituent, antioxidant and antibacterial activities of sugarcane molasses towards foodborne pathogens

Shafiqa-Atikah¹,

M.A.R.²,

Mahyudin³

et al. 2020

Food Res.

View full text Add to dashboard Cite

The employment of chemical synthetic as an antimicrobial agent in inhibiting microbial growth has become a major concern due to adverse health impact, food safety crisis and the pressure on food manufacturers. Essential bioactive compound in sugarcane molasses, a by-product from a sugar refinery process could be effective as an alternative antimicrobial substance. However, their antimicrobial properties are not understandable. This study aimed 1) to detect the total phenolic compounds present in sugarcane molasses extract and 2) to determine the antioxidants and antibacterial activities of sugarcane molasses extract towards foodborne pathogens. The phenolic compounds of sugarcane molasses extract were determined by UHPLC-MSMS. Antioxidant activities were estimated by a total phenolic compound assay and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Meanwhile, antibacterial activities were carried out via disc diffusion, minimum inhibition concentrations (MICs) and minimum bactericidal concentrations (MBCs) assays. In this study, several extracted compounds were identified in sugarcane molasses extract and included gallic acid, phenylvaleric acids, quinic acid, tannic acid and 6-C-glucosyl-8-C-arabinosyl apigenin or arabinoysl-glucosylapigenin. The sugarcane molasses extract showed high total phenolic compounds with values of 7.6 mg GAE/g extract. Meanwhile, antioxidant activities of sugarcane molasses extract were also found high and the 50% inhibitory concentration (IC 50 value) was about 0.79 mg QE/g. The inhibition zone against four foodborne pathogens, Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella enterica serovar Typhimurium ranged from 8.82±0.3 mm to 25.05±1.6 mm. Meanwhile, the MICs of sugarcane molasses extract ranged from 3.125% to 6.25% v/v and MBCs were 6.25% to >12.5% v/v. In conclusion, sugarcane molasses extract is rich in phenolic compounds and has the potential to be applied as the natural antioxidant and antibacterial compounds.

show abstract

Influence of Chemical Modifications of Polyhydroxyalkanoate-Derived Fatty Acids on Their Antimicrobial Properties

Cited by 13 publications

References 44 publications

Chemical Profile of Launaea nudicaulis Ethanolic Extract and Its Antidiabetic Effect in Streptozotocin-Induced Rats

Chemical Profile of Launaea nudicaulis Ethanolic Extract and Its Antidiabetic Effect in Streptozotocin-Induced Rats

In Search of Effective Anticancer Agents—Novel Sugar Esters Based on Polyhydroxyalkanoate Monomers

Evaluation of phenolic constituent, antioxidant and antibacterial activities of sugarcane molasses towards foodborne pathogens

Contact Info

Product

Resources

About