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Wrocław, Poland

Wincza E.,Wroclaw University of Technology | Lochynski S.,Wroclaw University of Technology | Lochynski S.,Institute of Cosmetology
Arkivoc | Year: 2012

Starting from (+)-3-carene 1, naturally occurring bicyclic, monoterpene hydrocarbon, (-)-cis- carane-4-one 3 was obtained as a result of the two-step synthesis. Our investigations were focused on the optimization of chemical Baeyer-Villiger reaction of 3 leading to å-lactones. A mixture of terpenoid lactones 4a, 4b was obtained and next separated using column chromatography. The pure compounds were subjected to the evaluation of antifeedant activity towards three species of storage insects. Fusarium culmorum, Fusarium oxysporum and Aspergillus niger were chosen among six fungal strains to perform microbiological Baeyer- Villiger oxidation. As a result, three derivatives were isolated and characterized by spectroscopic methods. ©ARKAT-USA, Inc.

Strub D.,Wroclaw University of Technology | Balcerzak L.,Wroclaw University of Technology | Lochynski S.,Institute of Cosmetology
Current Organic Chemistry | Year: 2014

In this article we present (+)-3-carene as a valuable source for the synthesis of compounds with various odoriferous properties. Described compounds consist of carane, bicyclo[3.1.0]hexane, and gem-dimethylcyclohexane system in their structure. Olfactory comparative analysis with regard to the structure has been discussed. Fragrance of molecules varies from different fruit notes to floral and woody. Future prospects regarding application of biocatalysts towards synthesis of compounds with olfactory properties are briefly discussed and the synthesis details are also presented to show the simplicity of the preparation of some valuable fragrant molecules. The major part of our study has been previously described only in patents that in our opinion makes this paper a valuable data source of olfactory characteristics of low-molecular compounds derived from (+)-3-carene. © 2014 Bentham Science Publishers.

Koziol A.,Wroclaw University of Technology | Stryjewska A.,Wroclaw University of Technology | Librowski T.,Jagiellonian University | Salat K.,Jagiellonian University | And 4 more authors.
Mini-Reviews in Medicinal Chemistry | Year: 2014

Monoterpenes, the major components of essential oils, belong to the group of isoprenoids containing ten carbon atoms. Being widely distributed in the plant kingdom they are extensively used in cuisine and human health care products. Studies have shown that both natural monoterpenes and their synthetic derivatives are endowed with various pharmacological properties including antifungal, antibacterial, antioxidant, anticancer, antiarrhythmic, anti-aggregating, local anesthetic, antinociceptive, anti-inflammatory, antihistaminic and anti-spasmodic activities. Monoterpenes act also as regulators of growth, heat, transpiration, tumor inhibitors, inhibitors of oxidative phosphorylation, insect repellants, feline and canine attractants and antidiabetics. These interesting activities which might be potentially used not only in pharmaceutical, but also food and cosmetic industries are discussed below. © 2014 Bentham Science Publishers

Jolanta P.,Wroclaw University of Technology | Jan S.D.,Wroclaw University of Technology | Agata K.,Wroclaw University of Technology | Stanislaw L.,Wroclaw University of Technology | Stanislaw L.,Institute of Cosmetology
Mini-Reviews in Organic Chemistry | Year: 2014

Limonoids are chemically classified on the basis of the four rings, marked as A, B, C and D in the intact triterpene nucleus with various oxidative modifications. The structural variations of limonoids found in Rutaceae species are lesser than in species of Meliaceae. Limonoids isolated from the plant family Meliaceae are more complex with very high degree of oxidation and structural rearrangements. Limonoids family exhibits a wide spectrum of biological properties, such as cytostatic, antimalarial, anti-inflammatory, antifeedant, antiviral, neuroprotective and a number of other activities like antimicrobial acitivity. © 2014 Bentham Science Publishers.

Szebesczyk A.,Institute of Cosmetology | Olshvang E.,Weizmann Institute of Science | Shanzer A.,Weizmann Institute of Science | Carver P.L.,University of Michigan | Gumienna-Kontecka E.,Wroclaw University
Coordination Chemistry Reviews | Year: 2016

Innovative strategies are needed to address the current lack of clinically available antifungal drugs and for diagnostic techniques. 'Repurposing' of antifungal drugs, similar to techniques currently being utilized with 'older' antibacterial drugs in order to combat widespread resistance in the face of a dearth of new drugs, could prove beneficial. Although as yet very limited for fungi, a siderophore-based 'Trojan Horse' strategy, in the form of siderophore-antibiotic conjugates, siderophore-fluorescent probe conjugates, or Ga(III)-siderophore complexes, reveals potential clinical relevance and provides a strategy for targeting fungal infections through drug delivery, imaging, and in diagnostics. The application of siderophores against pathogenic fungi is evolving but is still far from its full potential, and further studies are needed to demonstrate their advantages and limitations.One of the biggest obstacles in developing fungus-specific diagnostics and side-effects-free therapeutics is that apart from the fungal cell wall, fungi are metabolically similar to mammalian cells; thus, pathogen-specific targets are extremely limited. One of the few fundamental differences between fungal and mammalian cells lies in the iron acquisition system. The most common mechanism is mediated by small organic chelators - siderophores, often essential for fungal virulence and pathogenicity. Fungi synthesize mainly hydroxamate-type siderophores, which are excreted into the environment, and bind ferric ions with high affinity and selectivity. Delivery of iron-loaded siderophores back to the pathogen occurs via specific membrane receptors and transport proteins.Natural siderophores are generally not species-specific; they exhibit broad-spectrum activity and can be recognized by various types of microorganisms. Moreover, they generally miss proper sites for incorporating additional functionalities; e.g. fluorescent probes, surface-adhesive moieties or drug molecules, to be used for imaging and/or as therapeutic conjugates smuggled into microbial species via siderophore recognition and a 'Trojan Horse' strategy. Biomimetic analogues can overcome both these limitations and offer novel tools for both diagnostics and therapeutics. Siderophore mimics with a narrow spectrum of activity offer the possibility of developing selective diagnostic tools, while those with broad-spectrum activity may find therapeutic applications as antifungal drug delivery tools. © 2016 Elsevier B.V.

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