Stanisław Lochyński

• Prof.
• Professor (Full) at Wrocław University of Science and Technology

Due to market and legislative expectations, there is a constant need to explore new potential antimicrobial agents for functional perfumery. In this study, we evaluated the antimicrobial activity of 53 low molecular oximes and the corresponding carbonyl compounds against Escherichia coli, Enterococcus hirae, Pseudomonas aeruginosa, Bacillus cereus,...

Cyanobacteria are characterized by a very high tolerance to environmental factors. They are found in salt water, fresh water, thermal springs, and Antarctic waters. The wide spectrum of habitats suitable for those microorganisms is related to their particularly effective metabolism; resistance to extreme environmental conditions; and the need for o...

Terpenoids with lactone moieties have been indicated to possess high bioactivity. Certain terpenoid lactones exist in nature, in plants and animals, but they can also be obtained by chemical synthesis. Terpenoids possessing lactone moieties are known for their cytotoxic, anti-inflammatory, antimicrobial, anticancer, and antimalarial activities. Mor...

Oximes, which are highly bioactive molecules, have versatile uses in the medical sector and have been indicated to possess biological activity. Certain oximes exist in nature in plants and animals, but they are also obtained by chemical synthesis. Oximes are known for their anti-inflammatory, antimicrobial, antioxidant and anticancer activities. Mo...

Oximes, which are highly bioactive molecules, have versatile uses in the medical sector and have been indicated to possess biological activity. Certain oximes exist in nature in plants and animals, but they are also obtained by chemical synthesis. Oximes are known for their anti-inflammatory, antimicrobial, antioxidant and anticancer activities. Mo...

Urease is an important virulence factor for a variety of pathogenic bacteria strains such as Helicobacter pylori, which colonizes human gastric mucosa, and Proteus sp., responsible for urinary tract infections. Specific inhibition of urease activity could be a promising adjuvant strategy for eradication of these pathogens. Due to the interesting an...

Incorporation of the Beckmann rearrangement into the presented research resulted in the formation of nitrogen-containing terpenoid derivatives originating from naturally occurring compounds. Both starting monoterpenes and obtained derivatives were subjected to estimation of their antibacterial potential. In the presented study, Staphylococcus aureu...

In the synthesis performed in this study, derivatives of 4‐tert‐butylcyclohexanone 1 were obtained using typical reactions of organic synthesis. The bioactivity of the selected compounds was evaluated. 1‐(Bromomethyl)‐8‐tert‐butyl‐2‐oxaspiro[4.5]decan‐3‐one (5) was characterized by attractant properties against larvae and a weak feeding deterrent a...

Terpenoid derivatives, which contain a preserved carane system in their structure, exhibit a broad spectrum of biological activities. Among them, we can distinguish insecticides, structures with pharmacological application etc. In the presented paper, the substrate - (–)-cis-caran-trans-4-ol was transformed using the reactions of typical organic sy...

Cardiovascular diseases are described as the leading cause of morbidity and mortality in modern societies. Therefore, the importance of cardiovascular diseases prevention is widely reflected in the increasing number of reports on the topic among the key scientific research efforts of the recent period. The importance of essential fatty acids (EFAs)...

γ -Lactones are well known organic compounds. They can be isolated from many different plants, e.g. from Asteraceae (Compositae) family. They are used as active ingredients of various medicinal herbs and exhibit a variety of biological activities, i.e. antiviral, antibacterial, anticancer, antimalarial, anti-inflammatory and others. Among described...

3(RS)-Hydroxy-2-methylenebutanenitrile was synthesized from acetaldehyde and acrylonitrile with DABCO as a catalyst. Optimization of the reaction conditions was conducted because some literature procedures were not reproducible. Asymmetric transesterification of the Morita-Baylis-Hillman adduct was carried out using ten lipases. The hydroxyl-nitril...

Polyunsaturated fatty acids (PUFAs) are crucial for our health and wellbeing; therefore, they have been widely investigated for their roles in maintaining human health and in disease treatment. Most Western diets include significant amount of saturated and omega-6 fatty acids and insufficient quantity of omega-3; however, the balance between omega-...

Novel semi-synthetic fragrant compounds were prepared from both isomers of carvone. Deprotonation of (+) and (−)-carvone oximes with sodium hydride and subsequent O-Alkylation with various alkyl halides in DMSO resulted in 18 ethers. Scents of most synthesized compounds are agreeable. A shift of fragrance is observed between substrates. The scent o...

Background: Anxiety-related disorders are among the most common mental illnesses in the world for which benzodiazepines, buspirone and antidepressant drugs remain the first-line treatment. These drugs have good efficacy but they have numerous disadvantages, such as drug abuse potential, delayed onset of action or tolerance. A literature review rev...

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 pharmacolo...

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 hig...

Monoterpenes are widely used in food technology, cosmetic and pharmaceutical industries and as compounds of agricultural importance. It is known that compounds comprising this class can be transformed by a variety of organisms, namely by: bacteria, fungi, yeasts, plants or isolated enzymes. Biotransformations as one of the most important tools of g...

O-alkylation of (+) and (-)-fenchone oximes with various alkyl halides led to 20 novel ethers. Better results were obtained when mild reaction conditions were employed (i.e., aprotic, polar solvent and room temperature). The hydrolytic kinetic resolution of the O-glycidyl derivative was carried out using cobalt-salen catalysts. The best results wer...

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 va...

Fermented tea broth (known as Kombucha) has been used for ages in many countries, especially in Japan, Russia, China and Eastern Europe. Nowadays, this beverage is generally regarded a universal natural medicament having a strengthening effect on the human body. Kombucha beverage is popular because of its favourable effect on human health. Its comp...

Pharmaceutical biotechnology has a long tradition and is rooted in the last century, first exemplified by penicillin and streptomycin as low molecular weight biosynthetic compounds. Today, pharmaceutical biotechnology still has its fundamentals in fermentation and bioprocessing, but the paradigmatic change affected by biotechnology and pharmaceutic...

Monoclonal antibodies, modern vaccines and gene therapy have become a major field in modern biotechnology, especially in the area of human health and fascinating developments achieved in the past decades are impressive examples of an interdisciplinary interplay between medicine, biology and engineering. Among the classical products from cells one c...

Industrial biotechnology has been defined as the use and application of biotechnology for the sustainable processing and production of chemicals, materials and fuels. It makes use of biocatalysts such as microbial communities, whole-cell microorganisms or purified enzymes. In the review these processes are described. Drug design is an iterative pro...

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 ε-lactones. A mixture of terpenoid lactones 4a, 4b was obtained and next separated us...

Biotransformations are a standard tool of green chemistry and thus are following the rules of sustainable development. In this article, we describe the most common types of reactions conducted by microorganisms applied towards synthesis of chiral terpenoid derivatives. Potential applications of obtained products in various areas of industry and agr...

Previous studies of the propranolol monoterpene derivative (-)-4-[2-hydroxy-3-(N-isopropylamino)-propoxyimino]-cis-carane hydrochloride (KP-23) and its diastereoisomers, KP-23R and KP-23S, demonstrated different effects on the cyclic AMP generating system as well as anti-inflammatory, analgesic, antihistaminic and antioxidant activity. The present...

In the search of new chiral derivatives with olfactory properties we performed stereoselective reactions mediated by different strains of microorganisms such as Aspergillus niger, Fusarium oxysporum, Fusarium culmorum, Hansenula anomala and Streptomyces lusitanus StA. Oxidation of (+)-3-carene with O2 and CrO3 led to (+)-3-carene-5-one and (−)-3-ca...

L-Carnitine is an endogenous molecule involved in fatty acid metabolism, biosynthesized within the human body using amino acids: L-lysine and L-methionine, as substrates. L-Carnitine can also be found in many foods, but red meats, such as beef and lamb, are the best choices for adding carnitine into the diet. Good carnitine sources also include fis...

Two anal, methods (spectrophotometry, spectrofluorometry) were tested for their applicability for enzymatic detn. of total and free L-carnitine contents in cow, goat and sheep milk samples. The samples were preliminary prepd. by hydrolysis with KOH at 60°C for 1 h, neutralization with HCIO4 and ultrafiltration and then analyzed after enzymatic acet...

Several novel cyclopropyl-rigidified γ- and δ-amino acids 3–4 have been prepared starting from monoterpene (+)-3-carene 2. These compounds are proposed as chiral analogues of γ-aminobutyric acid (GABA) 1 and are expected to be of interest as potential inhibitors of GABA receptors.

gamma-Amino butyric acid is an extremely important inhibitory neurotransmitter in the mammalian central nervous system and is essential for the overall balance between neuronal excitation and inhibition. It is well documented that GABA deficiency is associated with several important neurological disorders such as Huntington's chorea, Parkinson's an...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Starting from (+)-3-carene 1, several chiral fragrant compounds with the bicyclo[3.1.0]hexane system were synthesized. These compounds were used as substrates for the biotransformation with lipases as biocatalysts. Pure diastereoisomers were obtained and their absolute configuration was confirmed by X-ray crystallography. The olfactory properties o...

Gene therapy has become a promising technique for the treatment of cancer. Nevertheless, the success of gene therapy depends on the effectiveness of the vector. The challenge of a gene carrier is to deliver exogenous DNA from the site of administration into the nucleus of the appropriate target cell. Polymer-based vectors are biologically safe, hav...

In this work we aimed at finding a concise method for the design of the new pharmacologically active compound 6, which is a precursor to obtaining non-protein amino acid 7 considered as GABA analogue, furthermore it can be used to construct enantiopure, conformationally restricted peptides. For this purpose the Schmidt reaction was applied.

In this work we aimed at finding a concise method for the design of the new pharmacologically active compound 6, which is a precursor to obtaining non-protein amino acid 7 considered as GABA analogue, furthermore it can be used to construct enantiopure, conformationally restricted peptides. For this purpose the Schmidt reaction was applied.

The present study was designed to investigate the central nervous system activity of terpene GABA (and piracetam) derivatives designated as BF-1, BF-2, BF-3, BF-4, BF-5, BF-6. We assessed their anticonvulsant activity in the two main mouse models of seizures (MES-test, PTZ-test), an antidepressant-like effect in the forced swim test (FST), as well...

Chiral iodo- 9, bromo- 10 and hydroxylactones 12 condensed with the carane system were obtained. In each case, the synthetic pathway led to an enantiomerically pure diastereoisomer to generate two stereogenic centers. Iodo- 9 and bromolactone 10 possess a γ-lactone group while the hydroxylactone 12 possesses a δ-lactone moiety situated trans to the...

Starting from (+)-3-carene I several chiral fragrant compounds with the bicyclo[3.1.0]hexane system 4-6 and 10-20 were synthesized. These compounds are structural analogues of naturally occurring fragrant compounds, such as ionones and damascones, and possess either an endo- or an exo-cyclic double bond in the bicyclo[3.1.0]hexane moiety. The absol...

Molecular dynamics (MD) simulations of two hydrated palmitoyloleoylphosphatidylcholine (POPC) bilayers each containing eight carane derivative (KP-23) local anesthetic (LA) molecules in neutral (POPC-LA) or protonated (POPC-LAH) forms were carried out to investigate the effect of KP-23 and its protonation on the bilayer. 3-ns trajectories were used...

Molecular dynamics (MD) simulations of two hydrated palmitoyloleoylphosphatidylcholine (POPC) bilayers each containing eight carane derivative (KP-23) local anesthetic (LA) molecules in neutral (POPC-LA) or protonated (POPC-LAH) forms were carried out to investigate the effect of KP-23 and its protonation on the bilayer. 3-ns trajectories were used...

Starting from (+)-3-carene 1 several spirolactones with carane backbone were synthesized. δ-Hydroxy-γ-lactone 5 was obtained by acidic lactonization of a γ,δ-epoxy ester. Iodolactone 8 and bromolactone 9 were products of iodolactonization of γ,δ-unsaturated acid 7 and bromolactonization of γ,δ-unsaturated ester 3 respectively. The halo lactones wer...

We have developed a stereoselective hydrolytic kinetic resolution process for diastereoisomeric mixtures of epoxyiminocarene intermediates in the presence of (R,R)-(−)-(salen)Co(III)OAc catalyst, this was applied as the first step in the synthesis of novel chiral aminohydroxyiminocarane derivatives with local anaesthetic activity. The absolute conf...

Starting from (+)-3-carene, nine new odoriferous derivatives were obtained. In comparison with (+)-3-carene, compounds synthesized contain at C-10 substituents such as methylcarbethoxy, 2-hydroxyethyl and 2-acetoxyethyl. The (+)-3-carenyl-10-acetaldehyde (10) and its acyclic and cyclic acetals were also synthesized. The odour characteristics of com...

Th e paper rep ort s on str u ctura l investi gation and phase analysis of a newly synthesi zed p otent lo cal anesthetic with chiral molecula r structure . A bsolute structure and absolute conÙguration on four chiral centres was determined using micro crystal li ne single -cry stal di ˜racti on with anomalous scattering of X -ray radiation azimuth...

Our previously conducted pharmacological screening led as to the discovery of the strong local anesthetic activity of the compound designated as KP-23. Earlier crystallographic studies revealed that the compound KP-23 crystallized in diastereoisomeric form in lowest symmetry. The aim of these comparative investigations was to evaluate anesthetic ac...

Comparative investigations of hydroxyamine carane derivative and its R,S-diastereo-isomers with strong local anesthetic activity. T. LIBROWSKI, R. CZARNECKI, S. LO-CHYÑSKI, B. FR¥CKOWIAK, M. PASENKIEWICZ-GIERULA, J. GROCHOWSKI, P. SERDA. Pol. J. Pharmacol., 2001, 53, 535–539. Our previously conducted pharmacological screening led as to the discover...

The syntheses and stereochemistry of two new amino acids obtained from the monoterpene ketones (−)-cis-caran-trans-4-one and (−)-menthone via appropriate lactams are presented. The configuration of all stereogenic centers is confirmed by X-ray crystallography.

The synthesis of four new derivatives of cis-hydroxy-cis-dihydropinol with allyl-, epoxyalkyl-, hydroxyalkyl- and ketoalkyl-groups substituted on the cyclohexane ring is presented. The cis-orientation of hydroxyl group at C-2 and the configuration of all stereogenic centers is confirmed by X-ray crystallography.

The paper reports on structural investigation and phase analysis of a newly synthesized potent local anesthetic with chiral molecular structure. Absolute structure and absolute configuration on four chiral centres was determined using microcrystalline single-crystal diffraction with anomalous scattering of X-ray radiation azimuthal scan technique....

A few derivatives of natural, bicyclic monoterpenes, which are propranolol analogs, were synthetized. Those compounds were studied pharmacologically in order to determine their toxicity, antiarrhythmic activity in selected experimental models of arrhythmia, the local anesthetic effect and influence on the cardiovascular system. The tested compounds...

Esters of N,N-diethylaminoacetic acid and hydroxyamines, obtained from structurally different natural monoterpenes, were pharmacologically examined. It was proved that salts of the obtained compounds had local anesthetic properties in infiltration anesthesia, compounds 9, 6 and 8 having been more potent than lidocaine. Compounds 7-9 slightly increa...

From the essential oil of Artemisia salsoloides the oxygenated monoterpenes 1, and 3–8 could be isolated. The easy formation of the hydroperoxide 2 from 1 suggests a biogenetic pathway from geraniol/nerol to 3. By comparison, the synthesized 8 exhibits mushroom and celery odor, typical of fractions of the A. salsoloides oil containing 8.

Synthesis and physicochemical and pharmacological properties of 10 analogs of 2-[2-(6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethoxy]N, N-diethylamino ethane (3) have been described. The compounds possess toxicity close to or lower than the parent compound--myrtecaine, have no antiarrhythmic activity but some of them (15, 16, 22, 24), similarly as c...

1H NMR spectra of 21 5-substituted-thianthreniumyl perchlorates are reported that allow chemical shift and structural assignments to be made.

Reactions of thianthrene cation radical perchlorate (Th.+ClO4-) with R4Sn, R = methyl (Me), ethyl (Et), n-butyl (Bu), phenyl (Ph), and vinyl, in acetonitrile took place cleanly in the stoichiometric ratio Th.+ClO4-/R4Sn 2:1. Oxidative cleavage of R4Sn occurred into R3Sn3+, that was assayed as R3SnCl, and the radical R.. The latter was primarily tra...

Reactions of dialkylmercurials (R2Hg) with thianthrene cation radical perchlorate (Th.+ClO4-) in acetonitrile solution have been studied in quantitative detail. Evidence was obtained from reactions of MeHgR (R = Et, i-Pr, t-Bu) that reaction begins with electron transfer rather than with electrophilic cleavage of an alkyl-mercury bond. That is, eac...

The alcohol (II) is prepared starting from (+)-3-carene (I) via the bromide (VIII).

A new group of juvenoids with the 5,5-dimethylcyclohex-3-ene system was obtained by a multi-step synthesis starting from (+)-3-carene (1). Esters 15, 16 and 18 were synthesized by the Wadsworth-Emmons reaction of ketone 14 or aldehyde 17 with appropriate phosphonates. Esters 19 and 20 were obtained by the Claisen rearrangement of allylic alcohol 21...

New cyclic juvenoids containing the 3,3-dimethylcyclohexane (esters16,18,22,26, and ethers28 a, b) or the 5,5-dimethyl-2-cyclohexene system (esters15,17,21,25, and ethers27 a,b) have been obtained by a several-step synthesis starting from dimedone (1). The compounds obtained exhibited morphogenetic activity against larvae ofDysdercus cingulatus and...

Aus (+)-3-Caren (I) wird über den Aldehyd (II) unter Erhaltung der Konfiguration an den Brückenkopf-C-Atomen das Bicyclohexen (III) dargestellt, dessen Hydrierung zu einem Gemisch (96 :4) der Cyclohexane (IVa) und (IVb) führt.