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International Journal of Toxicology Sep 2020The Expert Panel for Cosmetic Ingredient Safety (Panel) reviewed the safety of polyenes, which are reported to function in cosmetics primarily as film formers and... (Review)
Review
The Expert Panel for Cosmetic Ingredient Safety (Panel) reviewed the safety of polyenes, which are reported to function in cosmetics primarily as film formers and viscosity increasing agents. The Panel reviewed relevant data related to these ingredients, not inggaps in the available safety data for some of the polyenes in this safety assessment. The data available for many of the ingredients are sufficient and can be extrapolated to support the safety of the entire group because of the similarities in the chemical structures, chemical properties, use concentrations, and reported functions across the group. The Panel concluded that polyenes were safe in cosmetics in the present practices of use and concentration described in this safety assessment.
Topics: Animals; Consumer Product Safety; Cosmetics; Humans; Polyenes; Risk Assessment; Toxicity Tests
PubMed: 32975153
DOI: 10.1177/1091581820952385 -
Journal of Natural Products Aug 2023Turonicin A () was isolated from sp. MST-123921, which was recovered from soil collected on the banks of the Turon River in New South Wales, Australia. Turonicin A ()...
Turonicin A () was isolated from sp. MST-123921, which was recovered from soil collected on the banks of the Turon River in New South Wales, Australia. Turonicin A () is an amphoteric linear polyene polyketide featuring independent pentaene and tetraenone chromophores and is structurally related to linearmycins A-C (-). The structure of was determined by detailed spectroscopic analysis and comparison to literature data. Bioinformatic analysis of the linearmycin biosynthetic gene cluster also allowed the previously unresolved absolute stereostructures of - to be elucidated. Turonicin A () exhibited very potent activity against the fungi (MIC 0.0031 μg/mL, 2.7 nM) and (MIC 0.0008 μg/mL, 0.7 nM), moderate activity against the bacteria (MIC 0.097 μg/mL, 85 nM) and (MIC 0.39 μg/mL, 340 nM), and no cytotoxicity against human fibroblasts, making it an attractive candidate for further development as a potential next-generation antibiotic scaffold.
Topics: Humans; Antifungal Agents; Polyketides; Streptomyces; Australia; Anti-Bacterial Agents; Polyenes; Microbial Sensitivity Tests
PubMed: 37526586
DOI: 10.1021/acs.jnatprod.3c00144 -
Free Radical Research Dec 2020We previously demonstrated that coencapsulation of the potent antioxidant astaxanthin (Asx) and tocotrienols into liposomes results in synergistically higher...
We previously demonstrated that coencapsulation of the potent antioxidant astaxanthin (Asx) and tocotrienols into liposomes results in synergistically higher antioxidative activity than the calculated additive activity of each individual antioxidant-containing liposome, due to intermolecular interactions between terminal ring moieties of the two antioxidants and the polyene chain and the triene moiety. We reported that intermolecular interactions depend on the stereochemistry of Asx, and change the electronic state of the Asx polyene moiety. Based on these findings, we hypothesised that antioxidants that interact with Asx at the terminal ring and polyene moieties may enhance the antioxidative activity. Herein, we selected two candidate antioxidants, capsaicin (Cap) and resveratrol, based on their structures, in which the compounds exhibit similar characteristics to tocotrienols. We evaluated the antioxidative capacities of liposomes coencapsulating Asx and the selected candidates. Based on hydroxyl radical scavenging activity, Cap was found to synergistically enhance the antioxidative activity of Asx at an optimal Asx/Cap ratio. Intermolecular interactions between Asx and Cap are necessary for the synergistic effect, and the Asx stereoisomer 3,3'-form (Asx-) was predicted to most potently interact. Liposomes coencapsulating Asx- and Cap exhibited clear synergistic antioxidative activity at an optimal ratio, whereas liposomes coencapsulating the other Asx stereoisomer and Cap did not demonstrate such activity. Computational chemistry analysis showed that changes in the electronic state of the polyene moiety of Asx- are crucial for the synergistic activity. These results suggest that antioxidants that can change the electronic state of Asx via intermolecular interactions may enhance the function of Asx.
Topics: Antioxidants; Humans; Models, Molecular; Xanthophylls
PubMed: 31718328
DOI: 10.1080/10715762.2019.1693042 -
Carbohydrate Polymers Mar 2015Plasticized chitosan and polyethylene blends were produced through a single-pass extrusion process. Using a twin-screw extruder, chitosan plasticization was achieved in...
Plasticized chitosan and polyethylene blends were produced through a single-pass extrusion process. Using a twin-screw extruder, chitosan plasticization was achieved in the presence of an acetic acid solution and glycerol, and directly mixed with metallocene polyethylene, mPE, to produce a masterbatch. Different dilutions of the masterbatch (2, 5 and 10 wt% of plasticized chitosan), in the presence of ethylene vinyl acetate, EVA, were subsequently achieved in single screw film extrusion. Very small plasticized chitosan domains (number average diameter <5 μm) were visible in the polymeric matrix. The resulting films presented a brown color and increasing haze with chitosan plasticized content. Mechanical properties of the mPE films were affected by the presence of plasticized chitosan, but improvement was observed as a result of some compatibility between mPE and chitosan in the presence of EVA. Finally the incorporation of plasticized chitosan affected mPE water vapor permeability while oxygen permeability remained constant.
Topics: Chitosan; Glycerol; Mechanical Phenomena; Optical Phenomena; Oxygen; Permeability; Plasticizers; Polyenes; Temperature; Vinyl Compounds; Volatilization; Water
PubMed: 25498623
DOI: 10.1016/j.carbpol.2014.09.058 -
Molecules (Basel, Switzerland) Jun 2019is a small but well-known genus of actinomycetes for production of ansamitocin, the payload component of antibody-drug conjugates against cancers. However, the...
is a small but well-known genus of actinomycetes for production of ansamitocin, the payload component of antibody-drug conjugates against cancers. However, the secondary metabolite production profile of ATCC 31565, the most famous producer of ansamitocin, has never been fully explored. Our antiSMASH analysis of the genomic DNA of ATCC 31565 revealed a NRPS-PKS gene cluster for polyene macrolactam. The gene cluster is very similar to gene clusters for mirilactam and salinilactam, two 26-membered polyene macrolactams from and , respectively. Guided by this bioinformatics prediction, we characterized a novel 26-membered polyene macrolactam from ATCC 31565 and designated it pretilactam. The structure of pretilactam was elucidated by a comprehensive analysis of HRMS, 1D and 2D-NMR, with absolute configuration of chiral carbons predicted bioinformatically. Pretilactam features a dihydroxy tetrahydropyran moiety, and has a hexaene unit and a diene unit as its polyene system. A preliminary antibacterial assay indicated that pretilactam is inactive against and .
Topics: Actinobacteria; Biosynthetic Pathways; Chromatography, Liquid; Genes, Bacterial; Genome, Bacterial; Genome-Wide Association Study; Lactams; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Structure; Multigene Family; Open Reading Frames; Polyenes; Secondary Metabolism
PubMed: 31248172
DOI: 10.3390/molecules24122281 -
Applied Microbiology and Biotechnology Sep 2023Fungichromin is a polyene macrolide antibiotic with potent killing activity against a broad range of agricultural pathogens and filamentous fungi and a wide range of...
Fungichromin is a polyene macrolide antibiotic with potent killing activity against a broad range of agricultural pathogens and filamentous fungi and a wide range of potential applications. The production of fungichromin is still hampered by poor fermentation yield and high cost. In this study, the whole genome sequencing of fungichromin-producing Streptomyces sp. WP-1 was conducted, and the fungichromin biosynthetic gene cluster was identified. Comparative analysis revealed that the fungichromin biosynthetic gene cluster contains two regulatory genes, ptnF, and ptnR. The roles of ptnF and ptnR were determined through knockout and complementation. The yield of fungichromin was increased by overexpressing these two regulatory genes, as well as the crotonyl CoA reductase/carboxylase gene ptnB in Streptomyces sp. WP-1. The yield of fungichromin was increased to 8.5 g/L using a combination of genetic engineering and a medium optimization strategy, which is the highest fermentation titer recorded. KEY POINTS: • Confirmation of the positive regulation of ptnF and ptnR on fungichromin. • Improvement of fungichromin production by the construction of ptnF, ptnR, and ptnB overexpression strains. • Improvement of fungichromin production by the addition of soybean oil and copper ions at optimal concentration.
Topics: Streptomyces; Macrolides; Genetic Engineering; Polyenes; Multigene Family
PubMed: 37417973
DOI: 10.1007/s00253-023-12672-4 -
Chembiochem : a European Journal of... May 2022δ-Hydroxy-β-keto esters and δ,β-dihydroxy esters are characteristic structural motifs of statin-type natural products and drug candidates. Here, we describe the...
δ-Hydroxy-β-keto esters and δ,β-dihydroxy esters are characteristic structural motifs of statin-type natural products and drug candidates. Here, we describe the synthesis of functionalized δ-hydroxy-β-keto esters in good yields and excellent enantioselectivities using Chan's diene and modified Mukaiyama-aldol reaction conditions. Diastereoselective reduction of δ,β-dihydroxy esters afforded the respective syn- and anti-diols, and saponification yielded the corresponding acids. All products were evaluated for their anti-inflammatory properties, which uncovered a surprising structure-activity relationship.
Topics: Anti-Inflammatory Agents; Biological Products; Esters; Polyenes; Structure-Activity Relationship
PubMed: 35244320
DOI: 10.1002/cbic.202200073 -
Organic Letters Mar 2022A formal synthesis of FR252921, a potent macrocyclic immunosuppressive agent, and a six-step synthesis of vitamin A have been demonstrated. The application of a...
A formal synthesis of FR252921, a potent macrocyclic immunosuppressive agent, and a six-step synthesis of vitamin A have been demonstrated. The application of a ruthenium-catalyzed step-economic and environmentally benign strategy for the highly stereo- and chemoselective construction of valuable polyene motifs of FR252921 and vitamin A highlights the syntheses. The key features for the synthesis FR252921 include preparation of the triene moiety followed by two consecutive peptide couplings of the three fragments.
Topics: Biological Products; Lactams; Lactones; Polyenes; Vitamin A
PubMed: 35274951
DOI: 10.1021/acs.orglett.2c00546 -
Applied and Environmental Microbiology Apr 2021A group of polyene macrolides mainly composed of two constituents was isolated from the fermentation broth of Men-myco-93-63, which was isolated from soil where potato...
A group of polyene macrolides mainly composed of two constituents was isolated from the fermentation broth of Men-myco-93-63, which was isolated from soil where potato scabs were repressed naturally. One of these macrolides was roflamycoin, which was first reported in 1968, and the other was a novel compound named Men-myco-A, which had one methylene unit more than roflamycoin. Together, they were designated RM. This group of antibiotics exhibited broad-spectrum antifungal activities against 17 plant-pathogenic fungi, with 50% effective concentrations (EC) of 2.05 to 7.09 μg/ml and 90% effective concentrations (EC) of 4.32 to 54.45 μg/ml, which indicates their potential use in plant disease control. Furthermore, their biosynthetic gene cluster was identified, and the associated biosynthetic assembly line was proposed based on a module and domain analysis of polyketide synthases (PKSs), supported by findings from gene inactivation experiments. Men-myco-93-63 is a biocontrol strain that has been studied in our laboratory for many years and exhibits a good inhibitory effect in many crop diseases. Therefore, the identification of antimicrobial metabolites is necessary and our main objective. In this work, chemical, bioinformatic, and molecular biological methods were combined to identify the structures and biosynthesis of the active metabolites. This work provides a new alternative agent for the biological control of plant diseases and is helpful for improving both the properties and yield of the antibiotics via genetic engineering.
Topics: Ascomycota; Bacterial Proteins; Biological Control Agents; Biosynthetic Pathways; Macrolides; Multigene Family; Mycelium; Plant Diseases; Polyenes; Streptomyces
PubMed: 33637575
DOI: 10.1128/AEM.03157-20 -
The Journal of Organic Chemistry Apr 2022An efficient cobalt-catalyzed geometrical isomerization of 1,3-dienes is described. In the combination of a CoCl precatalyst with an amido-diphosphine-oxazoline ligand,...
An efficient cobalt-catalyzed geometrical isomerization of 1,3-dienes is described. In the combination of a CoCl precatalyst with an amido-diphosphine-oxazoline ligand, the geometrical isomerization of / mixtures of 1,3-dienes proceed in a stereoconvergent manner, affording () isomers in high stereoselectivity. This facile transformation features a broad substrate scope with good functional group tolerance and could be scaled up to the gram scale smoothly with a catalyst loading of 1 mol %.
Topics: Catalysis; Cobalt; Isomerism; Polyenes
PubMed: 35275485
DOI: 10.1021/acs.joc.1c03164