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Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells Ekowati, Juni; Rudyanto, Marcellino; Sasaki, Shigeru; Budiati, Tutuk; Sukardiman, .; Hermawan, Adam; Meiyanto, Edy
Indonesian Journal of Cancer Chemoprevention Vol 1, No 1 (2010)
Publisher : Indonesian Research Gateway

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (4.399 KB)

Abstract

Ethyl p-methoxycinnamate, major ingredient of Kaempferia galanga rhizome, have been reported not only has analgesic – anti inflammatory activities like NSAIDs which inhibited cyclooxygenase, but also inhibit tumor cell proliferation in specimen of mouse epidermis. Therefore, it will be interesting to carry out  synthetic studies on the derivates of ethyl  p-methoxycinnamate and searching their citotoxic activity on WiDr cell. We wish to report of structure modification on carboxyl moiety of  ethyl p-methoxycinnamate  and  evaluation on their citotoxic activity  on WiDr cell. Isolation of ethyl p-methoxycinnamate from Kaempferia galanga rhizome was carried out by percolation with ethanol 96% as solvent. Hydrolysis of ethyl p-methoxycinnamate in basic condition was performed to obtain p-methoxycinnamic acid. Preparation of some thiourea derivates of ethyl  p-methoxycinnamate was carried out  by microwave irradiation. Citotoxicity assay was carried out by MTT method for 48 h.   Modification  of  carboxyl  group  of  ethyl  p-methoxycinnamate to its thiourea form could be carried out by microwave irradiation gave; (E)-3-(4-methoxyphenyl)-N-(phenylcarba- mothioyl)acrylamide (50%); (E)-3-(4-methoxyphenyl)-N-(4-methoxyphenylcarbamothi- oyl)acrylamide (26%) and (E)-3-(4-methoxyphenyl)-N-(4-methylphenylcarbamothioyl) acrylamide (54%), yield calculated for 2 step from the acid chloride. All compounds showed no citotoxic effect on WiDr cell at 48 h incubation.
HUBUNGAN STRUKTUR TURUNAN N-KLOROBENZOILAMOKSISILIN DAN AKTIVITAS ANTIBAKTERINYA TERHADAP Pseudomonas aeruginosa ATCC 27853 Kusumowati, Ika Trisharyanti Dian; Siswandono, .; Rudyanto, Marcellino
JFIOnline | Print ISSN 1412-1107 | e-ISSN 2355-696X Vol 5, No 3 (2011)
Publisher : Indonesian Research Gateway

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Abstract

The aim of this research is to determine structure-activity relationship N-chlorobenzoylamoxicillin derivatives against Pseudomonas aeruginosa ATCC 27853. Antibacterial activities of the N-benzoylamoxicillin­ derivatives against Pseudomonas aeruginosa ATCC 27853 were tested using dilution method. The result showed that there was significance MIC of amoxycillin with N-benzoylamoxycillin, N-2-chlorobenzoylamoxycillin, and N-3-chlorobenzoylamoxycillin. Non linier regression between log MIC and lypophilic parameter N-chlorobenzoylamoxycillin derivatives showed -log KHM = 3,963 p2 - 3,001 p - 2,477, r = 0,906. To see more clearly quantitative strucuture-activity relationship of N-benzoylamoxicillin derivatives, further similar studies need to be done by increasing numbers of another N-benzoylamoxicillin derivative compounds.  ABSTRAK Penelitian ini bertujuan mengetahui hubungan struktur-aktivitas antibakteri senyawa-senyawa turunan N-kolorobenzoilamoksisilin terhadap Pseudomonas aeruginosa ATCC 27853. Uji aktivitas antibakteri turunan senyawa N-klorobenzoilamoksisilin terhadap Pseudomonas aeruginosa ATCC 27853 dilakukan dengan metode dilusi. Nilai KHM menunjukkan adanya perbedaan aktivitas yang bermakna antara amoksisilin dengan N-benzoilamoksisilin, N-2-klorobenzoilamoksisilin, dan N-3-klorobenzoilamoksisilin. Persamaan non linier log KHM dengan sifat lipofilik senyawa turunan N-klorobenzoilamoksisilin diperoleh -log KHM = 3,963 p2 - 3,001 p - 2,477, dengan harga r = 0,906.
HUBUNGAN STRUKTUR TURUNAN N-KLOROBENZOILAMOKSISILIN DAN AKTIVITAS ANTIBAKTERINYA TERHADAP Pseudomonas aeruginosa ATCC 27853 Kusumowati, Ika Trisharyanti Dian; Siswandono, .; Rudyanto, Marcellino
Jurnal Farmasi Indonesia Vol 5, No 3 (2011)
Publisher : Jurnal Farmasi Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.35617/jfi.v5i3.49

Abstract

The aim of this research is to determine structure-activity relationship N-chlorobenzoylamoxicillin derivatives against Pseudomonas aeruginosa ATCC 27853. Antibacterial activities of the N-benzoylamoxicillin­ derivatives against Pseudomonas aeruginosa ATCC 27853 were tested using dilution method. The result showed that there was significance MIC of amoxycillin with N-benzoylamoxycillin, N-2-chlorobenzoylamoxycillin, and N-3-chlorobenzoylamoxycillin. Non linier regression between log MIC and lypophilic parameter N-chlorobenzoylamoxycillin derivatives showed -log KHM = 3,963 p2 - 3,001 p - 2,477, r = 0,906. To see more clearly quantitative strucuture-activity relationship of N-benzoylamoxicillin derivatives, further similar studies need to be done by increasing numbers of another N-benzoylamoxicillin derivative compounds.  ABSTRAK Penelitian ini bertujuan mengetahui hubungan struktur-aktivitas antibakteri senyawa-senyawa turunan N-kolorobenzoilamoksisilin terhadap Pseudomonas aeruginosa ATCC 27853. Uji aktivitas antibakteri turunan senyawa N-klorobenzoilamoksisilin terhadap Pseudomonas aeruginosa ATCC 27853 dilakukan dengan metode dilusi. Nilai KHM menunjukkan adanya perbedaan aktivitas yang bermakna antara amoksisilin dengan N-benzoilamoksisilin, N-2-klorobenzoilamoksisilin, dan N-3-klorobenzoilamoksisilin. Persamaan non linier log KHM dengan sifat lipofilik senyawa turunan N-klorobenzoilamoksisilin diperoleh -log KHM = 3,963 p2 - 3,001 p - 2,477, dengan harga r = 0,906.
SINTESIS N-3-CHLOROBENZOYLAMOXICILLIN DAN UJI AKTIVITAS ANTIBAKTERINYA TERHADAP Pseudomonas aeruginosa ATCC 27853 Ika T. D. Kusumowati Siswandono; Marcellino Rudyanto
Farmasains : Jurnal Farmasi dan Ilmu Kesehatan Vol. 1 No. 2 (2011): Oktober 2010 - Maret 2011
Publisher : Universitas Muhammadiyah Malang

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22219/far.v1i2.1166

Abstract

N-3-chlorobenzoylamoxicillin were prepared by reacting 3-chlorobenzoylchloride with amine group of amoxicillin (acylation reaction). The reaction is nucleophilic substitution reaction in which primary amine group of the amoxicillin, which was nucleophilic in nature, attack C=O groups of benzoyl chloride-derivatives which has positive charge. The results showed that percentages of N-3-chlorobenzoylamoxicillin were 75%, respectively. Rf value of the resulting compounds different from Rf value of the amoxicillin. The structures were identified by Infra Red Spectrophotometry and Nuclear Magnetic Resonance (1H-NMR) Spectrometry. The results of the spectral analysis showed that spectra of amoxicillin and N-3-chlorobenzoylamoxicillin had changed significantly. The resulting structure was well fitted to the expected compounds. Antibacterial activities of N-3-chlorobenzoylamoxicillin­ against Pseudomonas aeruginosa ATCC 27853 were tested using dilution method. Minimum Inhibition Concentration achieved in the research represented the lowest level that can inhibit bacterial growth adequately. Analysis of the Minimum Inhibition Concentration on Pseudomonas aeruginosa ATCC 27853 showed significant differences between amoxicillin and N-3-chlorobenzoylamoxicillin.
REVITALISASI USAHA KECIL MENENGAH DHARMA BOGA BOJONEGORO MELALUI PELATIHAN CARA PRODUKSI DAN REGISTRASI PANGAN YANG BAIK SERTA HALAL Isnaeni; Noor Erma Nasution; Sugijanto; Hadi Poerwono; Juni Ekowati; Siswandono; Marcellino Rudyanto; Kholis Amalia Nofianti; Achmad Syahrani; Suzana
Panrita Abdi - Jurnal Pengabdian pada Masyarakat Vol. 5 No. 2 (2021): Jurnal Panrita Abdi - April 2021
Publisher : LP2M Universitas Hasanuddin

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20956/pa.v5i2.5754

Abstract

Abstract. The independence of food supply in Indonesia is supported by the abundant diversity of natural ingredients from vegetable, animal and mineral sources. Compared to drugs, dependence on food products in other countries is relatively lower, because the fabrication requires facilities and infrastructure that can be fulfilled domestically. The regulatory system managed by the Republic of Indonesia Drug and Food Control Agency (BPOM-RI) has been implemented to ensure that food products consumed by the public are of high quality, nutritious, safe, halal, and affordable and with a taste that satisfies user communities. Circular-worthy products must at least meet the registration requirements of halal aspects, maximum microbial limits and chemical contamination. The growth of Micro, Small and Medium Enterprises (MSMEs) is also facilitated by the government. Dharma Boga is one of the Small and Medium Enterprises (UKM) in Klangon sub-district, Bojonegoro which is engaged in food production for more than 10 years. Some problems related to registration, halal certification and handling of production, especially food additives that meet requirements, has been communicated to the Community Service Team (PENMAS) Faculty of Pharmacy, Airlangga University (FFUA). Alhamdulillah, PENMAS activities with training materials on how to produce and register good and halal food have been carried out with satisfactory results, although it still needs to be followed up with a partnership for the MSME revitalization program in the future. Of the three parameters used to measure participants' understanding of training material, the average obtained more than 30% showed an increase. For the introduction of the halal logo and the dangers of formaldehyde, 100% of the message is understood. The training involved experts and stakeholders in the authority of the East Java Indonesian Ulama Council and the teaching staff and the Airlangga University Faculty of Pharmacy Testing Service Unit.         Abstrak. Kemandirian penyediaan pangan di Indonesia didukung oleh diversitas bahan alam yang melimpah baik dari sumber nabati, hewani, maupun mineral. Dibandingkan obat, ketergantungan produk pangan pada negara lain relatif lebih rendah, karena fabrikasinya membutuhkan fasilitas dan infrastruktur yang dapat terpenuhi di dalam negeri. Sistem regulasi yang dikelola oleh Badan Pengawas Obat dan Makanan Republik Indonesia (BPOM-RI) telah diberlakukan untuk menjamin produk makanan yang dikonsumsi masyarakat berkualitas, bergizi, aman, halal, dan terjangkau serta dengan rasa yang memuaskan selera masyarakat. Produk yang laik edar minimal harus memenuhi persyaratan registrasi dari aspek halal, batas maksimum mikroba dan cemaran bahan kimia. Tumbuh kembangnya Usaha Mikro, Kecil dan Menengah (UMKM) juga difasilitasi oleh pemerintah. Dharma Boga adalah salah satu Usaha Kecil Menengah (UKM) di kecamatan Klangon, Bojonegoro yang bergerak dibidang produksi makanan selama lebih dari 10 tahun. Beberapa permasalahan terkait registrasi, sertifikasi halal dan penanganan produksi terutama bahan tambahan makanan yang memenuhi persyaratan, telah dikomunikasikan kepada Tim Pengabdian kepada Masyarakat (PENMAS) Fakultas Farmasi Univeritas Airlangga (FFUA). Alhamdulillah kegiatan PENMAS dengan materi pelatihan cara produksi dan registrasi pangan yang baik serta halal telah dilaksanakan dengan hasil yang memuaskan, walaupun masih perlu ditindaklanjuti dengan jalinan kerjasama untuk program revitalisasi UMKM di masa mendatang. Dari tiga parameter yang digunakan untuk mengukur pemahaman peserta terhadap materi pelatihan, rerata yang diperoleh lebih dari 30% menunjukkan peningkatan. Untuk pengenalan logo halal dan bahaya formalin, 100% peserta sudah paham. Pelatihan melibatkan pakar dan pemangku kewenangan dari Majelis Ulama Indonesia Jawa Timur dan para staf pengajar serta Unit Layanan Pengujian Fakultas Farmasi Universitas Airlangga.
Structure Modification of Ethyl p-methoxycinnamate Isolated from Kaempferia galanga Linn. and Citotoxicity Assay of The Products on WiDr Cells Juni Ekowati; Marcellino Rudyanto; Shigeru Sasaki; Tutuk Budiati; Sukardiman -; Adam Hermawan; Edy Meiyanto
Indonesian Journal of Cancer Chemoprevention Vol 1, No 1 (2010)
Publisher : Indonesian Society for Cancer Chemoprevention

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.14499/indonesianjcanchemoprev1iss1pp12-18

Abstract

Ethyl p-methoxycinnamate, major ingredient of Kaempferia galanga rhizome, have been reported not only has analgesic – anti inflammatory activities like NSAIDs which inhibited cyclooxygenase, but also inhibit tumor cell proliferation in specimen of mouse epidermis. Therefore, it will be interesting to carry out synthetic studies on the derivates of ethyl p-methoxycinnamate and searching their citotoxic activity on WiDr cell. We wish to report of structure modification on carboxyl moiety of ethyl p-methoxycinnamate  and  evaluation on their citotoxic activity  on WiDr cell. Isolation of ethyl p-methoxycinnamate from Kaempferia galanga rhizome was carried out by percolation with ethanol 96% as solvent. Hydrolysis of ethyl p-methoxycinnamate in basic condition was performed to obtain p-methoxycinnamic acid. Preparation of some thiourea derivates of ethyl p-methoxycinnamate was carried out  by microwave irradiation. Citotoxicity assay was carried out by MTT method for 48 h.Modification of carboxyl group of ethyl p-methoxycinnamate to its thiourea form could be carried out by microwave irradiation gave; (E)-3-(4-methoxyphenyl)-N-(phenylcarba- mothioyl)acrylamide (50%); (E)-3-(4-methoxyphenyl)-N-(4-methoxyphenylcarbamothi- oyl)acrylamide (26%) and (E)-3-(4-methoxyphenyl)-N-(4-methylphenylcarbamothioyl) acrylamide (54%), yield calculated for 2 step from the acid chloride. All compounds showed no citotoxic effect on WiDr cell at 48 h incubation.Keywords :  ethyl p-methoxycinnamate, microwave irradiation, Kaempferia galanga, citotoxicity, WiDr cell
The Effect of Methyl and Chloro Substituent Compounds in Amida Derivatives Synthesis from p-Metoxicynamic Acid with Microwaves Irradiation Ruri Intan Nurcahyaningtyas; Juni Ekowati Ekowati; Marcellino Rudyanto
Berkala Ilmiah Kimia Farmasi Vol. 7 No. 2 (2020): DESEMBER
Publisher : Universitas Airlangga

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (304.52 KB) | DOI: 10.20473/bikfar.v7i2.29300

Abstract

Background: The difference in the nature of these aromatic amine substituents, i.e. methyl and chloro will affect the N atom of aniline as a nucleophile to attack the carbonyl C atom in the p-methoxcycinnamoyl chloride in the synthesis two amides derivate of p-methoxycinnamic acid, namely N-(p-methylphenyl)-p-methoxycinnamide and N-(p-chlorophenyl)-p-methoxycinnamide. Aim: to obtain the N-(p-methylphenyl)-p-methoxycinnamide and the N-(p-chlorophenyl)-p-metoxicinamide compound from p-methoxycinamic acid using the microwave irradiation method as source of energy. Beside that, it also to determine the effect of the presence of methyl and chloro substituents in para position of aromatic amines in the yields of reactions. Method: The reactions were carried out by microwave irradiation at three powers, i.e 120 watts, 200 watts, 280 watts. After separation and purification steps, the products were identified by spectrometric methods. Result: At power of 200 watts for reaction time of 7.5 minutes, the yield of N-(p-methylphenyl)-p-methoxycinamide is larger than N-(p-chlorophenyl)-p-methoxycinnamamide. The percentage of the product synthesis of N-(p-methylphenyl)-p-methoxycinamide was 51.84% and the percentage of N-(p-chlorophenyl)-p-methoxycinnamamide was to 47.20%. Conclusion: The effect of substituent methyl is increase the percentage yield of N-(p-methylphenyl)-p-methoxycinamide compound than that substituent chloro of N-(p-chlorophenyl)-p-methoxycinamide compound under the same reaction conditions. Based on the identification of the structure of the synthesized compound using a UV spectrophotometer, infrared spectrophotomers and 1H-NMR spectrometer it can be concluded that the synthesized compounds are N-(p-methylphenyl)-p-methoxycinnamide and N- (p-chlorophenyl)-p-methoxycinnamide.  
Isolasi dan Karakterisasi Agarosa dari Rumput Laut Gracilaria verrucosa ZAINAL ABIDIN; MARCELLINO RUDYANTO; SUDJARWO SUDJARWO
JURNAL ILMU KEFARMASIAN INDONESIA Vol 13 No 1 (2015): JIFI
Publisher : Fakultas Farmasi Universitas Pancasila

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Abstract

: Agar is complex polysaccharide which could be isolated from group Rhodophyta of seaweeds, sucs as Gracilaria verrucosa. Agar consists of two components, namely agarose and agaropectin. Agarose is neutral polysaccharide, while agaropectin is polysaccharide that contain sulphate, so agarose could be used for gel electrophoresis. The use of NaOH solution was aimed to hydrolyzes the agar to form 3,6-anhydro-L-galactose, whereas the use of propylene glycol was to separates agarose from agaropectin. This research was aimed to isolate agarosa from Gracilaria verrucosa using NaOH solution with the concentrations of 4%, 6%, 8%, 10% and propylene glycol of 30, 50 and 70 mL. The agarose obtained was giving specivic absorbtion band in IR spectrum with wave number in the region of 930 and 890 cm-1, and there were absorbtion band in the region of 860 and 830 cm-1, indicated that the agarose still contained sulphate. The increase of NaOH concentration and propylene glycol volume caused drawback sulphate and ash content, constant melted temperature and gel temperature but increase gel strength. The best amount of agarose was obtained with the use of NaOH 10% and 70 mL of propylene glycol, with the characteristics were: ash content of 2.0035±0.0429% (w/w), sulphate content of 0.3236±0.0131% (w/w), melted temperature of 34 oC, gel temperature of 90 oC, gel strength of 432.195±26.172 g/cm2 and degree of electroendosmosis of 0.20±0.005.
SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE Marcellino Rudyanto; Lanny Hartanti
Indonesian Journal of Chemistry Vol 8, No 2 (2008)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (78.964 KB) | DOI: 10.22146/ijc.21626

Abstract

Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde.
ONE-STEP CONVERSION OF EUGENOL TO METHYL ISOEUGENOL USING MICROWAVE IRRADIATION IN SOLVENT-FREE CONDITIONS Marcellino Rudyanto; Lanny Hartanti
Indonesian Journal of Chemistry Vol 6, No 3 (2006)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (193.996 KB) | DOI: 10.22146/ijc.21734

Abstract

A research on conversion of eugenol to methyl isoeugenol via one-step reaction with microwave irradiation has been carried out. Mixtures containing eugenol, sodium or potassium carbonate as solid support, with or without sodium or potassium hydroxide as base, with or without tetrabutylammonium bromide as phase transfer catalyst, with dimethyl sulfate as the methylating agent were irradiated in a domestic microwave oven for 20 - 50 seconds. It was revealed that one-step methylation and isomerization required combinations of sodium or potassium hydroxide base and tetrabutylammonium bromide. Without combination of base and TBAB only one product, i.e. methyl eugenol, was formed.