Tutik Dwi Wahyuningsih
Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Jl. Sekip Utara, Yogyakarta 55281

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SYNTHESIS OF FLAVANONE-6-CARBOXYLIC ACID DERIVATIVES FROM SALICYLIC ACID DERIVATIVE Mardjan, Muhammad Idham Darussalam; Ambarwati, Retno; Matsjeh, Sabirin; Wahyuningsih, Tutik Dwi; Haryadi, Winarto
Indonesian Journal of Chemistry Vol 12, No 1 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (339.57 KB) | DOI: 10.22146/ijc.21374

Abstract

Synthesis of flavanone-6-carboxylic acid derivatives had been conducted via the route of chalcone. The synthesis was carried out from salicylic acid derivative, i.e. 4-hydroxybenzoic acid, via esterification, Fries rearrangement, Claisen-Schmidt condensation and 1,4-nucleophilic addition reactions. Structure elucidation of products was performed using FT-IR, 1H-NMR, GC-MS and UV-Vis spectrometers. Reaction of 4-hydroxybenzoic acid with methanol catalyzed with sulfuric acid produced methyl 4-hydroxybenzoate in 87% yield. The acid-catalyzed-acetylation of the product using acetic anhydride gave methyl 4-acetoxybenzoate in 75% yield. Furthermore, solvent-free Fries rearrangement of methyl 4-acetoxybenzoate in the presence of AlCl3 produced 3-acetyl-4-hydroxybenzoic acid as the acetophenone derivatives in 67% yield. Then, Claisen-Schmidt condensation of the acetophenone and benzaldehyde derivatives of p-anisaldehyde and veratraldehyde in basic condition gave 2'-hydroxychalcone-5'-carboxylic acid derivatives  in 81 and 71 % yield, respectively. Finally, the ring closure reaction of the chalcone yielded the corresponding flavanone-6-carboxylic acids in 67 and 59% yield, respectively.
SYNTHESIS OF 2-METHOXY-4,6-DI(PROP-1-ENYL)PHENOL FROM EUGENOL AND ITS ACTIVITY AS AN ANTIOXIDANT Hernawan, Hernawan; Purwono, Bambang; Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 12, No 2 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (325.695 KB) | DOI: 10.22146/ijc.21360

Abstract

Synthesis and antioxidant activity of 2-methoxy-4,6-di(prop-1-enyl) phenol from eugenol have been investigated. Synthesis was conducted through three stages of reaction. The first step was CTAB micellar catalytic O-allylation reaction at room temperature, to give 4-allyl-1-(allyloxy)-2-methoxybenzene (2). Compound (2) was subsequently heated for Claisen rearrangement and produced 2,4-diallyl-6- methoxyphenol (3). The final steps was isomerization of compound (3) in alkaline conditions in ethylene glycol, to yield 2-methoxy-4,6-di(prop-1-enyl) phenol (4). Antioxidant activity test was conducted by TBARS and DPPH methods. TBARS test showed that the compound (4) at a concentration of 50 ?M could inhibit the oxidation of linoleic acid shown by the increasing of time lag phase (96 ± 2.94 min), reducing the rate of propagation (± 54.54%) and reducing of malonal dialdehyde (MDA) formation (68.04 ± 0.84%). The DPPH test revealed that compound (4) indicated DPPH free radical scavenging activity with IC50 107.66 ?M and comparable with IC50 for BHT 107.37 ?M.
IMPROVED SYNTHESIS OF 2',6'-DIHYDROXY-3,4-DIMETHOXY CHALCONE BY GRINDING TECHNIQUE TO SYNTHESIZE 5-HYDROXY-3',4'-DIMETHOXY FLAVONE VH, Elfi Susanti; Matsjeh, Sabirin; Mustofa, Mustofa; Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 14, No 2 (2014)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (335.751 KB) | DOI: 10.22146/ijc.21255

Abstract

5-hydroxy-3',4'-dimethoxy flavone can be efficiently synthesized in two steps via the formation of 2',6'-dihydroxy-3,4-dimethoxy chalcone with good results. 2',6'-dihydroxy-3,4-dimethoxy chalcone as reactants for synthesis of flavones was prepared through Claisen-Schmidt condensation reaction between 2,6-dihydroxyacetophenones,3,4-dimethoxybenzaldehyde and solid NaOH in mortar for 15 min. The yield of the product (70%) is higher than conventional method (65%). This chalcone then oxidatively cyclized with iodine to form 5-hydroxy-3',4'-dimethoxy flavone (yield 62%). Compounds synthesized were characterized by spectroscopic (IR, 1H-NMR, and 13C-NMR).
SYNTHESIS OF NOVEL INDOLO[3,2-C]QUINOLINES; ETHYL 3-CHLORO-9,11-DIMETHOXY INDOLO[3,2-C]QUINOLINE-6-CARBOXYLATE Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 5, No 3 (2005)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (259.685 KB) | DOI: 10.22146/ijc.21786

Abstract

?-Carboline and its derivatives are significant due to their pharmacological importance. The synthesis of indolo[3,2-c]quinolines as a benzo analog of ?-carboline has been carried out via an oxime ether intermediate. Reaction of 2'-glyoxylic ester with hydroxylamine hydrochloride in the presence of sodium acetate afforded the oxime acetate in 82%. It was then treated with natrium and fluoro-2,4-dinitrobenzene in ethanol to give an orange solid of oxime ether acetate which is in subsequent treatment with a base yielded a pale yellow solid of indolo[3,2-c]carboline in 43%.
Identification of Pediococcus Strains Isolated from Feces of Indonesian Infants With in vitro Capability to Consume Prebiotic Inulin and to Adhere on Mucus ., Widodo; Anindita, Nosa Septiana; Taufiq, Tiyas Tono; Wahyuningsih, Tutik Dwi
Indonesian Journal of Biotechnology Vol 17, No 2 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (244.164 KB)

Abstract

The aim of this experiment was to identify isolates obtained from feces of Indonesian infants and to evaluate their capability as probiotics. Identification of isolates was carried out based on morphology, physiology and biochemical identifications, and molecular identification based on 16S rRNA sequence. Morphological and physiological identification was carried out based on Gram staining, shape, motility, spore formation and catalase production. Biochemical identifications based on production of CO2 and NH3 from glucose, the ability to grow on different temperature (10 and 45°C) and pH (4.4 and 9.6), and different salt concentration (6.5 and 18%). Probiotics capability of isolates was assayed on the ability to grow on low pH (pH 2.0), on different bile salts concentration (0.3; 0.5; 1.0 and 1.5%), the capacity to grow on media with inulin as the only carbon source, and in vitro adhesion ability on porcine mucin. Morphological, physiological and biochemical identification suggest that all of isolates belong to lactic acid bacteria. Further molecular identification of five isolates showedthat isolates AA, BE and BK were strains of Pediococcus acidilactici (similarity 99%), while isolate AP and AG were strains of Lactobacillus casei (similarity 99-100%). Probiotic assays showed that more than 80% of cells of Pediococcus acidilactici isolates AA, BE and BK were viable after grown on pH 2.0 for 90 min, and around 80% of cells from the same isolates were survived on media supplemented with bile salt 1.5% for 2 h. All of isolates had high adhesion capacity as seen by more than 75% of cells attached on pig gastric mucin. Investigationof isolates to grow on inulin showed Pediococcus acidilactici isolate BE was able to consume inulin as the only carbon source. It is concluded that Pediococcus acidilactici isolate BE was a candidate probiotics and subject to further in vivo evaluation using animal models to examine their beneficial health effects.Key word : Pediococcus acidilactici, Lactobacillus casei, human origin and probiotics.
Identification of Pediococcus Strains Isolated from Feces of Indonesian Infants With in vitro Capability to Consume Prebiotic Inulin and to Adhere on Mucus Widodo, W.; Anindita, Nosa Septiana; Taufiq, Tiyas Tono; Wahyuningsih, Tutik Dwi
Indonesian Journal of Biotechnology Vol 17, No 2 (2012)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (244.164 KB) | DOI: 10.22146/ijbiotech.7859

Abstract

The aim of this experiment was to identify isolates obtained from feces of Indonesian infants and to evaluate their capability as probiotics. Identification of isolates was carried out based on morphology, physiology and biochemical identifications, and molecular identification based on 16S rRNA sequence. Morphological and physiological identification was carried out based on Gram staining, shape, motility, spore formation and catalase production. Biochemical identifications based on production of CO2 and NH3 from glucose, the ability to grow on different temperature (10 and 45°C) and pH (4.4 and 9.6), and different salt concentration (6.5 and 18%). Probiotics capability of isolates was assayed on the ability to grow on low pH (pH 2.0), on different bile salts concentration (0.3; 0.5; 1.0 and 1.5%), the capacity to grow on media with inulin as the only carbon source, and in vitro adhesion ability on porcine mucin. Morphological, physiological and biochemical identification suggest that all of isolates belong to lactic acid bacteria. Further molecular identification of five isolates showedthat isolates AA, BE and BK were strains of Pediococcus acidilactici (similarity 99%), while isolate AP and AG were strains of Lactobacillus casei (similarity 99-100%). Probiotic assays showed that more than 80% of cells of Pediococcus acidilactici isolates AA, BE and BK were viable after grown on pH 2.0 for 90 min, and around 80% of cells from the same isolates were survived on media supplemented with bile salt 1.5% for 2 h. All of isolates had high adhesion capacity as seen by more than 75% of cells attached on pig gastric mucin. Investigationof isolates to grow on inulin showed Pediococcus acidilactici isolate BE was able to consume inulin as the only carbon source. It is concluded that Pediococcus acidilactici isolate BE was a candidate probiotics and subject to further in vivo evaluation using animal models to examine their beneficial health effects.Key word : Pediococcus acidilactici, Lactobacillus casei, human origin and probiotics.
SYNTHESIS OF DIOXO-DIOXANE AND DIOXO-DIOXEPANE ETHYL OLEATE DERIVATIVES AS BIO-LUBRICANT BASE STOCKS Wahyuningsih, Tutik Dwi; Kurniawan, Yehezkiel Steven
Indonesian Journal of Chemistry ARTICLE IN PRESS
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (304.802 KB) | DOI: 10.22146/ijc.42317

Abstract

In this study, two novel compounds, i.e., ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate and ethyl 8-(3-octyl-5,7-dioxo-1,4-dioxepan-2-yl)octanoate were prepared from oleic acid as the starting material. Both compounds were obtained from the esterification of the ethyl 9,10-dihydroxyoctadecanoate with dicarboxylic acids in the presence of p-toluenesulfonic acid as a catalyst. The chemical structures of the synthesized products were confirmed by FTIR, 1H-NMR, and MS spectrometers. The bio-lubricant properties of the products, such as density, total acid number, total base number, and iodine value, were determined and the effect of the dioxane and dioxepane heterocyclic rings to their bio-lubricant properties was discussed. The esterification of ethyl 9,10-dihydroxyoctadecanoate with oxalic acid gave ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate compound in 93.9% yield, while the esterification of ethyl 9,10-dihydroxyoctadecanoate with malonic acid gave ethyl 8-(3-octyl-5,7-dioxo-1,4-dioxepan-2-yl)octanoate compound in 89.6% yield. The density and total base number of the products were close to the standard commercial lubricant values. Meanwhile, the total acid number and the iodine value of the ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate were smaller than the standard commercial lubricant, showing that this compound is a promising bio-lubricant in a real application.
BIOSURFACTANTS PRODUCTION BY PSEUDOMONAS AERUGINOSA USING SOYBEAN OIL AS SUBSTRATE Suryanti, Venty; Hastuti, Sri; Wahyuningsih, Tutik Dwi; Mudasir, Mudasir; Muliawati, Dina Ika
Indonesian Journal of Chemistry Vol 9, No 1 (2009)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (1183.444 KB) | DOI: 10.22146/ijc.21570

Abstract

Optimization condition of the biosurfactants production by P. aeruginosa using soybean oil as substrate has been examined. The media containing 10% v/v of the soybean oil and 6 days of the fermentation time was the optimum condition for the biosurfactants production. The extraction technique using different solvent polarity (n-hexane, chloroform, ethyl acetate and buthanol, respectively) was applied for the isolation of the biosurfactants. The biosurfactant was found in the extract chloroform of the crude biospasoy (biosurfactants obtained from soybean oil as substrate) which then is called chlo-biospasoy. The chlo-biospasoy was identified as rhamnolipids which had oil in water (o/w) emulsion type, had the CMC of 860 mg/L and could reduced the surface tension of the water from 72 mN/m to 52 mN/m. The chlo-biospasoy could be used as an emulsifier to form emulsion between water and hydrocarbon such as palm oil, benzene, premium or toluene with various stability. The results indicated that chlo-biospasoy could be used as an emulsifying and emulsion-stabilizing agent.
SYNTHESIS OF NEW ACTIVATED INDOLES; 3-(4’-BROMOPHENYL)-4,6-DIMETHOXY-2-METHYLINDOLE Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 4, No 3 (2004)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (199.846 KB) | DOI: 10.22146/ijc.21853

Abstract

3-(4'-Bromophenyl)-4,6-dimethoxy-2-methylindole has been synthesized from 4,6-dimethoxyaniline via the modified Bischler method. Reaction of 4,6-dimethoxyaniline with 2,4-dibromopropiophenone gave an aniline ketone in 85%, and then it was protected to give the amido ketone as a white solid. Cyclization of amido ketone was performed by trifluoroacetic acid and subsequent deprotection with potassium hydroxide in methanol afforded a white solid of 3-(4'-bromophenyl)-4,6-dimethoxy-2-methylindole in 86%.
Method Development for the Analysis of Pharmaceuticals with Acethylcholinesterase Activity in Water Using HPLC-DAD and Solid Phase Extraction Wardhana, Samuel Budi; Kolb, Marit; Bahadir, Müfit; Purwono, Bambang; Wahyuningsih, Tutik Dwi
Indonesian Journal of Chemistry Vol 14, No 1 (2014)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (493.285 KB) | DOI: 10.22146/ijc.21263

Abstract

An SPE followed by HPLC-DAD method with ion pair chromatography technique to analyze pharmaceuticals with acethylcholinesterase activity including pyridostigmine (PYR), galathamine (GAL), neostigmine (NEO), eserine (ESE), and donepezil (DON) in water samples was developed. Acetylcholinesterase (AChE) inhibitors have been used to treat less severe dementias such as Alzheimer’s disease. Chromatographic separation was achieved using reversed-phase SymmetryShield column using gradient system with mobile phase consisting of H2O/ACN (99:1, v/v) as mobile phase A with 10 mM sodium 1-hexanesulfonate and 0.1% acetic acid (HAc). The HPLC/DAD method was linear between concentrations of 5 to 100 ng/μL. The IDL and IQL ranged from 0.50 to 1.25 ng/μL and 1.5 to 3.0 ng/μL, respectively. SPE was used to extract and clean up the target substances in spiked pure water, tap water, and wastewater samples. The application of extraction method of 5 target substances in wastewater sample was divided into 2 parts: Oasis WCX (6 mL, 500 mg) for PYR and Oasis HLB (6 mL, 200 mg) for GAL, NEO, ESE and DON. The developed SPE and HPLC/DAD method is applicable for quantification of the 5 target substances in water samples in a concentration range > 50 µg/L and assumable lower for DON (> 25 µg/L).