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BMC Microbiology Dec 2022The demand for natural coloring and preservative agents in food industry is increasing day by day as a result of awareness of the negative health effects of synthetic...
Irradiation impact on biological activities of Anthraquinone pigment produced from Talaromyces purpureogenus and its evaluation, characterization and application in beef burger as natural preservative.
BACKGROUND
The demand for natural coloring and preservative agents in food industry is increasing day by day as a result of awareness of the negative health effects of synthetic color preservatives. Consumers want foods with less processing, a longer shelf life, and clear labels that list only natural ingredients and food additives with familiar names that promote good health. In order to meet consumer demands and regain consumers' confidence in the safety of food products, the food industry was compelled to search for natural alternatives with strong antibacterial and antioxidant properties. Therefore, the objective of this study was to produce a microbial pigment that not only serve as food coloring agents but also provide health advantages owing to their bioactivities. Additionally, the potential use of anthraquinone pigment (AQP) as a natural food preservative compared to gamma irradiation was also examined to extend the shelf life of the beef burger and improve its hygienic quality.
RESULTS
This study used Talaromyces purpureogenus AUMC2603 to produce the red natural pigment, which was identified as an anthraquinone pigment (AQP). According to the results, gamma (γ) radiation had no significant effect on AQP's antibacterial properties. However, it has a negative, considerable effect on antioxidant activity, where a large dose of γ-ray may change the antioxidant components and lessen the AQP's capacity to scavenge free radicals. Additionally, the γ ray-treated AQP had a strong cytotoxic activity in relation to a high γ-ray dose. As a result, it is suggested that AQP-containing foods should not be irradiated. The extracted AQP was applied as a food additive to improve the quality and increase the shelf life of beef burgers. Significant antibacterial and antioxidant action has been shown at 2% (w/v) AQP. The findings demonstrated that the treatment of beef burger with AQP decreased the initial total bacterial count and psychrophilic bacteria and extended the shelf-life of beef burger in comparison to the control (beef burger with no addition of AQP, butylated hydroxytoluene (BHT) or gamma radiation treatment). On the other hand, there was no substantial difference in the overall amount of mold and yeast or coliform at zero time. According to sensory characteristics, beef burgers had a shelf life of 6 days for controls and 9, 12, and 15 days for AQP-treated samples at 0.5, 1 and 2%, respectively, compared to γ- irradiated samples, 9 and 21 days, at 3 and 5 Kilo Gray (KGy), respectively.
CONCLUSIONS
This research provides a natural red pigment from Talaromyces purpureogenus with potent biological activities as antimicrobials and antioxidants to be applied as coloring, additive, and preservative agent in the food industry. Also, the tested pigment offers a powerful alternative to gamma irradiation for extending the shelf life of food products.
Topics: Animals; Cattle; Antioxidants; Colony Count, Microbial; Anti-Bacterial Agents; Anthraquinones
PubMed: 36581795
DOI: 10.1186/s12866-022-02734-4 -
PloS One 2024In the search for better anticancer drugs, computer-aided drug design (CADD) techniques play an indispensable role in facilitating the lengthy and costly drug discovery...
BACKGROUND
In the search for better anticancer drugs, computer-aided drug design (CADD) techniques play an indispensable role in facilitating the lengthy and costly drug discovery process especially when natural products are involved. Anthraquinone is one of the most widely-recognized natural products with anticancer properties. This review aimed to systematically assess and synthesize evidence on the utilization of CADD techniques centered on the anthraquinone scaffold for cancer treatment.
METHODS
The conduct and reporting of this review were done in accordance to the Preferred Reporting Items for Systematic Reviews and Meta-analysis (PRISMA) 2020 guideline. The protocol was registered in the "International prospective register of systematic reviews" database (PROSPERO: CRD42023432904) and also published recently. The search strategy was designed based on the combination of concept 1 "CADD or virtual screening", concept 2 "anthraquinone" and concept 3 "cancer". The search was executed in PubMed, Scopus, Web of Science and MedRxiv on 30 June 2023.
RESULTS
Databases searching retrieved a total of 317 records. After deduplication and applying the eligibility criteria, the final review ended up with 32 articles in which 3 articles were found by citation searching. The CADD methods used in the studies were either structure-based alone (69%) or combined with ligand-based methods via parallel (9%) or sequential (22%) approaches. Molecular docking was performed in all studies, with Glide and AutoDock being the most popular commercial and public software used respectively. Protein data bank was used in most studies to retrieve the crystal structure of the targets of interest while the main ligand databases were PubChem and Zinc. The utilization of in-silico techniques has enabled a deeper dive into the structural, biological and pharmacological properties of anthraquinone derivatives, revealing their remarkable anticancer properties in an all-rounded fashion.
CONCLUSION
By harnessing the power of computational tools and leveraging the natural diversity of anthraquinone compounds, researchers can expedite the development of better drugs to address the unmet medical needs in cancer treatment by improving the treatment outcome for cancer patients.
Topics: Anthraquinones; Humans; Neoplasms; Antineoplastic Agents; Drug Design; Molecular Docking Simulation; Computer-Aided Design; Drug Discovery
PubMed: 38776291
DOI: 10.1371/journal.pone.0301396 -
Chemical & Pharmaceutical Bulletin 2014Certain amide-containing anthraquinone, xanthone, and carbazole derivatives have been synthesized and evaluated in vitro for their antiproliferative activities against a...
Certain amide-containing anthraquinone, xanthone, and carbazole derivatives have been synthesized and evaluated in vitro for their antiproliferative activities against a panel of human cancer cell lines including nasopharyngeal carcinoma (NPC-TW01), lung carcinoma (NCI-H661), and leukemia (Jurkat). Among them, 2-(9,10-dioxo-9,10-dihydroanthracen-2-yloxy)-N-(naphthalen-2-yl)acetamide (13) was the most active against NPC-TW01 with an IC50 value of 2.62 µM while its xanthone and dibenzofuran counterparts, 14 and 15, were inactive with an IC50 value of 16.10 and 11.09 µM, respectively. Studies on NPC-TW01 cell cycle distribution revealed that compound 13 inhibited proliferation of NPC-TW01 by the alteration of cell division and the accumulation of cells in G0/G1 phase.
Topics: Amides; Anthraquinones; Carbazoles; Cell Line, Tumor; Cell Proliferation; G1 Phase; Humans; Resting Phase, Cell Cycle; Xanthones
PubMed: 24390500
DOI: 10.1248/cpb.c13-00617 -
Molecules (Basel, Switzerland) Feb 2022belongs to the genus and is classified as an invasive parasitic plant in agriculture. Despite other species being widely used in herbal medicine due to their... (Review)
Review
belongs to the genus and is classified as an invasive parasitic plant in agriculture. Despite other species being widely used in herbal medicine due to their antimicrobial, antioxidant, antitumor, and anti-inflammatory effects, there are almost no information about the potential of confertus for the treatment of various diseases. In this review we analyzed scientific articles revealing properties of plant's substances against cancer, diabetes, pathogenic bacterial invasions, viruses, inflammation, and oxidative stress for the past 20 years. Compounds dominating in each composition of solvents for extraction were discussed, and common thin layer chromatography(TLC) and high performance liquid chromatography(HPLC) methods for efficient separation of the plant's extract are included. Physico-chemical properties such as solubility, hydrophobicity (Log P), pKa of flavonoids, anthraquinones, and other derivatives are very important for modeling of pharmacokinetic and pharmacodynamics. An overview of clinical studies for abounded selected substances of species is presented.
Topics: Anthraquinones; Anti-Bacterial Agents; Anti-Inflammatory Agents; Antineoplastic Agents, Phytogenic; Antioxidants; Flavonoids; Rumex
PubMed: 35208994
DOI: 10.3390/molecules27041204 -
Chemical & Pharmaceutical Bulletin Nov 2018Seven anthraquinones including two new compounds namely capillasterquinones A and B (1 and 2) and one new butenolide namely capillasterolide (8) were isolated and...
Seven anthraquinones including two new compounds namely capillasterquinones A and B (1 and 2) and one new butenolide namely capillasterolide (8) were isolated and structurally elucidated from the crinoid Capillaster multiradiatus. The inhibitory effect of compounds 1-8 on lipopolysaccharide (LPS)-induced nitric oxide (NO) production as well as inhibition of 1 on expressions of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) proteins in RAW264.7 cells were also evaluated. As the obtained results, capillasterquinone A (1) showed strong NO production inhibitory activity with an IC of 5.89±0.11 µM. In addition, compound 1 reduced the LPS-induced iNOS and COX-2 expressions in a dose-dependent manner.
Topics: 4-Butyrolactone; Animals; Anthraquinones; Cyclooxygenase 2; Dose-Response Relationship, Drug; Echinodermata; Enzyme Inhibitors; Lipopolysaccharides; Mice; Molecular Structure; Nitric Oxide; Nitric Oxide Synthase Type II; RAW 264.7 Cells; Structure-Activity Relationship
PubMed: 30135325
DOI: 10.1248/cpb.c18-00472 -
Cells Jan 2022Anthraquinone derivatives exhibit various biological activities, e.g., antifungal, antibacterial and in vitro antiviral activities. They are naturally produced in many...
Anthraquinone derivatives exhibit various biological activities, e.g., antifungal, antibacterial and in vitro antiviral activities. They are naturally produced in many fungal and plant families such as Rhamnaceae or Fabaceae. Furthermore, they were found to have anticancer activity, exemplified by mitoxantrone and pixantrone, and many are well known redox-active compounds. In this study, various nature inspired synthetic anthraquinone derivatives were tested against colon, prostate, liver and cervical cancer cell lines. Most of the compounds exhibit anticancer effects against all cell lines, therefore the compounds were further studied to determine their IC-values. Of these compounds, 1,4-bis(benzyloxy)-2,3-bis(hydroxymethyl)anthracene-9,10-dione () exhibited the highest cytotoxicity against PC3 cells and was chosen for a deeper look into its mechanism of action. Based on flow cytometry, the compound was proven to induce apoptosis through the activation of caspases and to demolish the ROS/RNS and NO equilibrium in the PC3 cell line. It trapped cells in the G2/M phase. Western blotting was performed for several proteins related to the effects observed. Compound enhanced the production of PARP and caspase-3. Moreover, it activated the conversion of LC3A/B-I to LC3A/B-II showing that also autophagy plays a role in its mechanism of action, and it caused the phosphorylation of p70 s6 kinase.
Topics: Adenine; Anthraquinones; Apoptosis; Autophagy; Caspases; Cell Line, Tumor; Cell Survival; DNA Topoisomerases; Drug Screening Assays, Antitumor; Emodin; Enzyme Activation; G2 Phase; Humans; Inhibitory Concentration 50; Mitosis
PubMed: 35011730
DOI: 10.3390/cells11010168 -
Marine Drugs Jul 2023New anthraquinone derivatives acruciquinones A-C (-), together with ten known metabolites, were isolated from the obligate marine fungus KMM 4696. Acruciquinone C is...
New anthraquinone derivatives acruciquinones A-C (-), together with ten known metabolites, were isolated from the obligate marine fungus KMM 4696. Acruciquinone C is the first member of anthraquinone derivatives with a 6/6/5 backbone. The structures of isolated compounds were established based on NMR and MS data. The absolute stereoconfigurations of new acruciquinones A-C were determined using ECD and quantum chemical calculations (TDDFT approach). A plausible biosynthetic pathway of the novel acruciquinone C was proposed. Compounds - and - showed a significant antimicrobial effects against growth, and acruciquinone A (), dendryol B (), coniothyrinone B (), and ω-hydroxypachybasin () reduced the activity of a key staphylococcal enzyme, sortase A. Moreover, the compounds, excluding , inhibited urease activity. We studied the effects of anthraquinones , , , and and coniothyrinone D () in an in vitro model of skin infection when HaCaT keratinocytes were cocultivated with . Anthraquinones significantly reduce the negative impact of on the viability, migration, and proliferation of infected HaCaT keratinocytes, and acruciquinone A () revealed the most pronounced effect.
Topics: Staphylococcus aureus; Ascomycota; Staphylococcal Infections; Anthraquinones
PubMed: 37623712
DOI: 10.3390/md21080431 -
Ambio Aug 2023The detection of anthraquinone in tea leaves has raised concerns due to a potential health risk associated with this species. This led the European Union to impose a...
The detection of anthraquinone in tea leaves has raised concerns due to a potential health risk associated with this species. This led the European Union to impose a maximum residue limit (MRL) of 0.02 mg/kg for anthraquinone in dried tea leaves. As atmospheric contamination has been identified as one of the possible sources of anthraquinone residue, this study investigates the contamination resulting from the deposition of atmospheric anthraquinone using a global chemical transport model that accounts for the emission, atmospheric transport, chemical transformation, and deposition of anthraquinone on the surface. The largest contribution to the global atmospheric budget of anthraquinone is from residential combustion followed by the secondary formation from oxidation of anthracene. Simulations suggest that atmospheric anthraquinone deposition could be a substantial source of the anthraquinone found on tea leaves in several tea-producing regions, especially near highly industrialized and populated areas of southern and eastern Asia. The high level of anthraquinone deposition in these areas may result in residues in tea products exceeding the EU MRL. Additional contamination could also result from local tea production operations.
Topics: Anthraquinones; Plant Leaves; Food Contamination; Atmosphere; Tea
PubMed: 37115429
DOI: 10.1007/s13280-023-01858-9 -
Chemosphere Jan 2022"Green" pyrotechnics seek to remove known environmental pollutants and health hazards from their formulations. This chemical engineering approach often focuses on...
"Green" pyrotechnics seek to remove known environmental pollutants and health hazards from their formulations. This chemical engineering approach often focuses on maintaining performance effects upon replacement of objectionable ingredients, yet neglects the chemical products formed by the exothermic reaction. In this work, milligram quantities of a lab-scale pyrotechnic red smoke composition were functioned within a thermal probe for product identification by pyrolysis-gas chromatography-mass spectrometry. Thermally decomposed ingredients and new side product derivatives were identified at lower relative abundances to the intact organic dye (as the engineered sublimation product). Side products included chlorination of the organic dye donated by the chlorate oxidizer. Machine learning quantitative structure-activity relationship models computed impacts to health and environmental hazards. High to very high toxicities were predicted for inhalation, mutagenicity, developmental, and endocrine disruption for common military pyrotechnic dyes and their analogous chlorinated side products. These results underscore the need to revise objectives of "green" pyrotechnic engineering.
Topics: Anthraquinones; Coloring Agents; Mutagens; Smoke; Nicotiana
PubMed: 34523441
DOI: 10.1016/j.chemosphere.2021.131845 -
Chemical & Pharmaceutical Bulletin 2022Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together...
Three new sulfated naphthopyrone derivatives namely delicapyrons F-H (1-3) and two new sulfated anthraquinone derivatives namely delicaquinons A (4) and B (5), together with 6-methoxycomaparvin-5-methylether-8-O-sodium sulfate (6), 6-methoxycomaparvin-8-O-sodium sulfate (7), comaparvin-8-O-sodium sulfate (8), and 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone-6-O-sodium sulfate (9) were isolated from the Vietnamese crinoid Comanthus delicata. Their chemical structures were elucidated by extensive analysis of the one dimensional (1D) and 2D-NMR, high resolution electrospray ionization quadrupole time-of-flight (HR-ESI-QTOF) mass spectra as well as calculation of optical rotation. In addition, significant cytotoxicity was observed for 6 against LNCaP (prostate cancer) cell line with IC value of 20.29 ± 2.43 µM, whereas moderate or weak cytotoxic effects were observed for 1-3 and 5-8 on SK-Mel-2 (melanoma) cell line and 7 and 8 against LNCaP cell line, with IC values ranging from 49.96 ± 1.74 to 76.92 ± 5.85 µM.
Topics: Animals; Anthraquinones; Antineoplastic Agents; Asian People; Echinodermata; Humans; Neoplasms
PubMed: 35491198
DOI: 10.1248/cpb.c21-00904