Ismail KiranEskisehir Osmangazi University | ESOGU · Department of Chemistry
Ismail Kiran
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Introduction
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January 2000 - present
Publications
Publications (77)
Cedramber (cedrol methyl ether) (1) is a fragrance compound used in cosmetics such as soap, detergents, creams, lotions and perfumes. New cedrol derivatives are of interest in this context. Here we report the first biotransformation reaction of cedramber by Aspergillus niger ATCC 10549. The conversion afforded two known cedrol derivatives namely, 1...
Background
A pentacyclic lupenane-type natural triterpenoid, betulin, has attracted attention in medicinal chemistry since it exhibited a variety of biological activities including anticancer activity.
Objective
In the present work, it was aimed to obtain derivatives of betulin through bacterial biotransformation and investigate its anticancer act...
β-Caryophyllene and longifolene are sesquiterpenes with characteristic aroma properties, which are primary constituents of essential oils and important ingredients commonly used in food, perfumery, cosmetics, detergents and pharmaceuticals, which create a worldwide market. β-Caryophyllene and longifolene were converted through microbial biotransfor...
Oleic acid is an unsaturated fatty acid found in significant quantities in various edible oils. Scientific studies have shown that oleic acid and its derivatives exhibit a variety of biological activities including antimicrobial and anticancer activities. In the present work, biotransformation of oleic acid was carried out initially using 27 differ...
Ionols are important flavour and fragrance compounds both in natural and synthetic aroma blends that are used in many daily products. α-Ionol has been converted for the first time to 3-oxo-α-ionone by microbial biotransformation using the plant pathogenic fungi Aspergillus niger NRRL 326 and Fusarium culmorum (freshly isolated) over 7 d at 25 °C at...
Cyclademol (1) was converted for the first time to 1-(4-hydroxy-3,3-dimethylcyclohexyl) ethanone (2) and 4-(1-hydroxyethyl)-2,2-dimethylcyclohexanol (3) with 31.2 and 15.1% yields by Aspergillus niger and Neurospora crassa, respectively. The resulting metabolite structures were established by FT-IR, MS and NMR spectroscopic studies, respectively. I...
Abietic acid, a natural compound, belongs to the abietane diterpene group occuring widely in trees [1]. Recent studies have shown that it exhibits diverse biological and pharmacological activities which include cardiovascular activity [2], in vitro testosterone 5α-reductase inhibitory activity [3] and anticancer activity [4].
In this study, it was...
Abiyetik asit (1), diterpen yapısına sahip bir bileşik olup, kolofan ve çam reçinesinden elde edilmektedir. Son dönemlerde gerçekleştirilen biyolojik aktivite çalışmalarında abiyetik asidin antikanser ve antimikrobiyal etki başta olmak üzere pek çok biyolojik aktivite gösterdiği ortaya konmuştur. Çalışmamızda, yeni ve etkili bir antikanserojen ilaç...
Background:
A monoterpene, perillyl alcohol, has attracted attention in medicinal chemistry since it exhibited chemo-preventive and therapeutic properties against a variety of cancers.
Objective:
In the present work, it was aimed to obtain derivatives of perillyl alcohol through microbial biotransformation and investigate their anticancer activi...
Biotransformation of abietic acid was carried out initially using 28 different microbial strains. Among the evaluated, Mucor ramannianus produced a known metabolite 2α-hydroxy-dehydroabietic acid whereas Neurospora crassa yielded two known metabolites of 7β-hydroxy-dehydroabietic and 1β-hydroxy-dehydroabietic acids in 12.7, 15.5 and 20.1% yields, r...
Caryophyllene and longifolene are two sesquiterpenes with aroma properties and primary constituents of essential oils [1]. Aroma compounds are highly important ingredients commonly used in food, perfumery, cosmetics, detergents and pharmaceutical industries and create a worldwide market. Their productions are mostly based on chemical synthesis or e...
Results The results showed that 2α-hydroxy-dehydroabietic acid was the most effective compound against A549 cell line with an IC 50 value of 320.77 and SI value of 156. On the other hand, 7β-hydroxy-dehydroabietic acid was found to be the most effective and selective antiproliferative agent against HepG2 cell line with an IC 50 value of 196.57 µg/m...
Oleic acid is an unsaturated fatty acid present in various vegetable oils such as hazelnut, sunflower and olive and found as glyceryl esters in animal fats by 30%. It is known that oxygenated fatty acids are effective against some cancer types (Bastida et al., 1999). Therefore derivatization of oleic acid is an important field of study. In this stu...
Oleic acid is a saturated fatty acid present in various vegetable oils such as hazelnut, sunflower and olive and found as glyceryl esters in animal fats by 30%. It is known that oxygenated fatty acids are effective against some cancer types [1]. Therefore derivatization of oleic acid is an important field of study. In this study, we aimed at obtain...
Oleic acid is an unsaturated fatty acid present in various vegetable oils such as hazelnut. It is known that oxygenated and unsaturated hydroxy fatty acids are involved in the defensive plant responses against pathogenic microorganisms. In this study, it was aimed to study the possible antimicrobial activities of oleic acid derivatives obtained thr...
Oleic acid is a mono-unsaturated fat found in significant quantities in various edible oils. Scientific studies have shown that consuming olive oil may help to lower the levels of harmful low-density lipoproteins in the bloodstream. It is also known that plants use oxygenated and unsaturated fatty acids against pathogenic microorganisms. Molecular...
References Oleic acid is a saturated fatty acid present in various vegetable oils such as hazelnut. It is known that oxygenated and unsaturated hydroxy fatty acids are involved in the defensive plant responses against pathogenic microorganisms [1,2]. In this study, it was aimed to study the possible antimicrobial activities of oleic acid derivative...
Isophorone (3,5,5-trimethyl-2-cyclohexen-1-one), a monoterpene, and the structurally related 1,8-cineole and camphor, have demonstrated a protective effect against cancer, biological activity against a variety of microorganisms, and anti-oxidant properties. The derivatization of isophorone is, therefore, an important field of xenobiochemistry, phar...
S-(-)-Perillyl alcohol (p-mentha-1, 8-diene-7-ol) (1) (500 mg) was converted by Fusarium heterosporium ATCC 15625 over 10 days at 25 degrees C to a new metabolite, 1,2-dihydroxyperillyl alcohol (p-mentha-8-en-1,2,7-triol) (3) in a yield of 13% (70 mg). The structure of 3 was established by IR and NMR spectroscopic, specific rotation, and mass spect...
Removal of dyes from wastewaters causes a big concern from the environmental point of view due to their extreme toxicity towards aquatic life and humans. Commonly used traditional methods to treat these effluents are ineffective because dyes show resistance to many chemicals, oxidizing agents, and light. In this context, the biosorption process has...
Incubation of alpha-cedrol and caryophyllene oxide with Neurospora crassa afforded 12beta-hydroxy cedrol, 10alpha-hydroxy cedrol, and 3beta-hydroxy cedrol, and 12beta-hydroxy caryophyllene oxide as major metabolites, respectively. The antibacterial and radical scavenging activities of the metabolites were evaluated in vitro using broth microdilutio...
The mutagenic activities of four steroid hormone derivatives, namely 6β-hydroxyandrost-4-ene-3,17-dione (1), 6β-acetoxyandrost-4-ene-3,17- dione (2), 17β-acetoxy-androst- 4- ene-3,6-dione (3) and cholest-4-ene-3,17-dione (4), were studied with umu test using Salmonella typhitnurium NM2009 and NM3009 strains. The results showed that the highest muta...
Biosorption potential of dried Neurospora crassa for Burazol Blue ED was studied with respect to pH, equilibrium time, biomass concentration and temperature to determine equilibrium and kinetic model parameters. The most suitable pH, equilibrium time and biomass concentration were determined as 1±0.2, 60min and 1.6g L−1, respectively, at 20°C±1.0....
Biosorption potential of dried anaerobic sludge (DAS) for Burazol Blue ED (BB) was studied with respect to pH, equilibrium time, initial dye concentrations and temperature to determine equilibrium and kinetic models. The most suitable pH, equilibrium time and initial dye concentration were determined as 0.5+/-0.03, 75 min and 150 mg/L, respectively...
To determine the protective effects of a fungal metabolite of demethoxyviridine (DMV) and its derivative, 1-alpha-hydroxy-DMV in the livers of 2-month-old male Spraque-Dawley rats treated with diethylnitrosamine (DEN) and 2-acetylaminflourene (2-AAF).
This study was performed in the Department of Medical Biology, Faculty of Medicine, Eskisehir Osma...
BACKGROUND: This paper evaluates the biosorption of Reactive Orange 122 dye (RO 122) by dried Penicillium restrictum cells. The aim was to determine the pH, contact time, temperature and dye concentration for the applicability of biomass as an alternative biosorbent for the removal of RO 122.
RESULTS: Optimum initial pH and equilibrium time for RO...
Biosorption of Reactive Black 5 (RB 5) dye onto dried Penicillium restrictum biomass was studied with respect to pH, contact time, biosorbent and dye concentrations. The effect of temperature on the biosorption efficiency was also carried out and the kinetic parameters were determined. Optimum initial pH, equilibrium time and biomass concentration...
The purpose of this work was to evaluate the adsorption potential of Capsicum annuum seeds, in a batch system for the removal of lead(II) ions from aqueous solutions. The experimental results showed that this agricultural by‐product was effective in removing lead(II) ions. The FT‐IR analysis indicated that the mechanism involved in adsorption of le...
Equilibrium, kinetics and thermodynamic studies on the removal of Acid Red 57 (AR57) by biosorption onto dried Cephalosporium aphidicola (C. aphidicola) cells have been investigated in a batch system with respect to pH, contact time and temperature. The results showed that the equilibrium time was attained within 40 min and the maximum biosorption...
Congress Abstract Sesquiterpenes are natural products mainly obtained from essential oils with a vast spectrum of bioactivities [1]. In recent years the use of sesquiterpenes as starting material in the microbial biotransformation of new compounds has been of great interest to chemical, cosmetic and pharmaceutical industries [1–3]. Within this scop...
Biosorption of Acid Red 57 (AR57) on to Neurospora crassa was studied with variation of pH, contact time, biosorbent and dye concentrations and temperature to determine equilibrium and kinetic models. The AR57 biosorption was fast and equilibrium was attained within 40 min. Langmuir, Freundlich and Dubinin–Radushkevich (D–R) isotherm models were ap...
Biosorption of lead(II) onto Cephalosporium aphidicola was examined and the effects of pH, contact time, biosorbent and lead(II) concentrations and temperature on biosorption were investigated. The nature of the possible cell and metal ion interactions was examined by the FTIR technique. The lead(II) biosorption was fast and equilibrium was attaine...
The sorption of Pb(II) and Cu(II) ions from aqueous solutions by raw and pretreated Neurospora crassa fungal biomass was investigated in the batch mode. The influence of solution pH, equilibrium time and initial metal ion concentration using dried N. crassa cells as well as pretreatment on the sorption capacity of the biomass at optimum conditions...
Pb(II) ions were found to be accumulated extracellularly on the surface of Botrytis cinerea. The rate and extent of accumulation were affected by pH, contact time and initial Pb(II) ion concentrations. The Pb(II) sorption capacities of heat inactivated, detergent, NaOH, DMSO and AcOH pretreated B. cinerea cells were determined as 107.10 ± 1.87, 57....
Adsorption of copper ions onto Capsicum annuum (red pepper) seeds was investigated with the variation in the parameters of pH, contact time, adsorbent and copper(II) concentrations and temperature. The nature of the possible adsorbent and metal ion interactions was examined by the FTIR technique. The copper(II) adsorption equilibrium was attained w...
The in vitro antibacterial and antifungal activities of demethoxyviridin and some synthetic analogues were evaluated by the agar diffusion method. The minimum inhibitory concentrations (MIC) of the active compounds were also determined by the agar dilution method. Demethoxyviridin (1) showed moderate antibacterial activity against most of the strai...
Racemic diisophorone (500 mg) was converted by Cephalosporium aphidicola and Neurospora crassa over 10 days at 25 degrees C to 8beta-hydroxydiisophorone in yields of 10% (52 mg) and 20% (103 mg), respectively. The structure was established by IR, specific rotation, mass spectral, 1D and 2D-NMR studies.
The removal of Cr(VI) from aqueous solutions by live and pretreated Neurospora crassa fungal biomass was investigated in the batch mode. The influence of solution pH, contact time and initial metal ion concentration as well as pretreatment of biomass on the biosorption efficiency were studied. All pretreatment methods were found to increase the bio...
The microbial transformation of racemic diisophorone was investigated using the plant pathogen Aspergillus niger as a biocatalyst. Incubation of diisophorone with Aspergillus niger gave 8α-hydroxy-diisophorone, 10-hydroxydiisophorone and 17-hydroxydiisophorone on the basis of their spectroscopic data including two-dimensional NMR analysis, nOe and...
The oxidation of readily available steroidal 3-chloro-3,5-dienes with chromic acid is shown to give the corresponding 4-ene-3,6-diones.
The effect of replacing a hydroxyl group by a methoxyl group on the microbiological hydroxylation of some steroids by the fungus, Cephalosporium aphidicola, has been examined.
The kinetically controlled alkylation of pregnenolone acetate has been used to prepare the 21,21-dimethyl analogue which was then converted into 21,21-dimethylprogesterone.
A tricyclic steroidal des-ring D-androstane derived from the Koster-Logemann ketone has been shown to undergo a backbone Westphalen rearrangement. The structures of the products have been established by X-ray crystallography.
17-Chloroandrosta-4,16-dien-3-one is hydroxylated at C-6β, C-11%alpha; and C-15β by the fungus Cephalosporium aphidicola.
Dehydroisoandrosterone was formylated at C-16 by a Vilsmeier reaction and by condensation with methyl formate. The product of the latter reaction was converted to 16-acetylandrosta-4,16-dien-3-one and its X-ray crystal structure was determined.
The kinetically controlled alkylation of pregnenolone acetate has been used to prepare the 21,21-dimethyl analogue which was then converted into 21,21-dimethylprogesterone.
Although steroids possessing a 4-formyl substituent undergo reduction on incubation with Mucor plumbeus, they do not appear to be substrates for efficient microbiological hydroxylation by this organism indicating that the structural requirements for these two enzyme systems are different.
The epoxidation of 6β-acetoxyandrosta-2,4-diene-17-one, 6β-acetoxypregna-2,4-diene-20-one and the corresponding 6-ketones with m-chloroperbenzoic acid is shown to give, unexpectedly, the 4α,5α-monoepoxides.
The epoxidation of 6β-acetoxyandrosta-2,4-diene-17-one, 6β-acetoxypregna-2,4-diene-20-one and the corresponding 6-ketones with m-chloroperbenzoic acid is shown to give, unexpectedly, the 4α,5α-monoepoxides.
The syntheses of a C-4:C-6 furano-steroid by the base-catalysed cyclization of 6α-acetoxyandrost-4-ene-3,17-dione and of a C-4:C-6 tetrahydrofuran by the cyclization of 3β,6β-dihydroxy-4β-hydroxymethylandrostan-17-one, are described.
The syntheses of a C-4:C-6 furano-steroid by the base-catalysed cyclization of 6α-acetoxyandrost-4-ene-3,17-dione and of a C-4:C-6 tetrahydrofuran by the cyclization of 3β,6β-dihydroxy-4β-hydroxymethylandrostan-17-one, are described.
The chromic acid oxidation of steroidal 2,4- and 3,5-dienes and 2,4,6-trienes is shown to take place at the secondary termini of the alkenes rather than at the allylic positions and is rationalized in terms of a sequence of 1:4-additions of chromic acid.
The chromic acid oxidation of steroidal 2,4- and 3,5-dienes and 2,4,6-trienes is shown to take place at the secondary termini of the alkenes rather than at the allylic positions and is rationalized in terms of a sequence of 1:4-additions of chromic acid.
The transannular directing effect of a 2α,3α-, 2β,3β- and 5α,6α-epoxide on the epoxidation of a 5-ene and a 2-ene, respectively, is shown to increase the proportion of epoxidation of the anti face of the alkene when compared to the unsubstituted 2- and 5-androstenes.
Unlike other acidic systems, the tetracyanoethylene catalysed methanolysis of androstane 2,3-epoxides proceeds normally without giving products arising from the transannular participation of a 5α,6α-epoxide, a 5α-hydroxy group or a 5(6)-ene.
Unlike other acidic systems, the tetracyanoethylene catalysed methanolysis of androstane 2,3-epoxides proceeds normally without giving products arising from the transannular participation of a 5α,6α-epoxide, a 5α-hydroxy group or a 5(6)-ene.
The transannular directing effect of a 2α,3α-, 2β,3β- and 5α,6α-epoxide on the epoxidation of a 5-ene and a 2-ene, respectively, is shown to increase the proportion of epoxidation of the anti face of the alkene when compared to the unsubstituted 2- and 5-androstenes.
The X-ray crystal structures of 6β-toluene-p-sulfonyloxymethyl-5β-hydroxy-B-norandrostane-3,17-dione (7) and 6β-methoxycarbonyl-3β,5β-dihydroxy-B-norandrostan-17-one (8) reveal that ring A exists in a twisted boat form in these 5β-B-norandrostanes.
The X-ray crystal structures of 6β-toluene- p-sulfonyloxymethyl-5β-hydroxy-B-norandrostane-3,17-dione (7) and 6β-methoxycarbonyl-3β,5β-dihydroxy-B-norandrostan-17-one (8) reveal that ring A exists in a twisted boat form in these 5β-B-norandrostanes.
The tetracyanoethylene catalysed methanolysis of 17β-acetoxy-4β,5β:6α,7α-diepoxyandrostane afforded 17β-acetoxy-4α,7α-oxido-5β-hydroxy-6β-methoxyandrostane in which the methanolysis product of the 6α,7α-epoxide has participated in the cleavage of the 4β,5β-epoxide; the reaction is modified however by an adjacent 3β-hydroxy group.
The tetracyanoethylene catalysed methanolysis of 17β-acetoxy- 4β,5β:6α,7α-diepoxyandrostane afforded 17β-acetoxy-4α,7α-oxido-5β- hydroxy-6β-methoxyandrostane in which the methanolysis product of the 6α, 7α-epoxide has participated in the cleavage of the 4β,5β-epoxide; the reaction is modified however by an adjacent 3β-hydroxy group.
The preparation of some substituted androstane 4- and 6-ketones is described revealing further examples of neighbouring group participation between substituents at C-4 and C-6; the X-ray crystal structure of androstane-4,6,17-trione showed that it existed in a form that was a hybrid of the Δ4- and Δ6-enolates.
The preparation of some substituted androstane 4- and 6-ketones is described revealing further examples of neighbouring group participation between substituents at C-4 and C-6; the X-ray crystal structure of androstane-4,6,17-trione showed that it existed in a form that was a hybrid of the Δ ⁴ - and Δ ⁶ -enolates.
The epoxidation of some androsta-4,6-dienes with m-chloroperbenzoic acid has been shown to give the 4β,5β;6α,7α-diepoxides, the stereochemistry can be rationalized in terms of the directing effect of one epoxide on the facial selectivity of the second epoxidation.
The epoxidation of some androsta-4,6-dienes with m-chloroperbenzoic acid has been shown to give the 4β, 5β; 6α, 7α-diepoxides, the stereochemistry can be rationalized in terms of the directing effect of one epoxide on the facial selectivity of the second epoxidation.
Syntheses are described of the aromatase inhibitor, androst-5-ene-4,7,17-trione, its 17β-acetate and A-nor analogue, A-norandrost-5-ene-3,7,17-trione, starting from dehydroisoandrosterone and testosterone.
Routes are described for the preparation of 4-chloroandrosta-3,5-diene-7,17-dione and the corresponding 17 beta-acetate starting from the readily available testosterone and dehydroisoandrosterone acetates.
Projects
Projects (4)
In this project, we aim at obtaining molecules which might show high biological activities starting with oleic acid using biotechnological methods and investigate possible antimicrobial, anticancer and cytotoxic activities of these molecules as potential active ingredients of novel drugs.
In this project, we aim to synthesize derivates of isophorone structurally similar to caffeic acid, a potato phytoalexin and one of the compounds found in Artemisia filifolia plant. We will investigate biological activities of these molecules as potential active ingredients of novel drugs. We expect to generate a positive accretion to our country medicine sector, greatly depending on foreign countries
The main objective of this study is to obtain natural derivatives of sesquiterpenes through microbial biotransformations in one step and investigate their ability as potential smell and odor substances.
