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Direct Amidation of ethyl p-methoxycinnamate to Produce N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide Ismiarni Komala; Supandi Supandi; Muhammad Mirza Hardiansyah
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 4, No. 1, Mei 2018
Publisher : Syarif Hidayatullah State Islamic University

Ethyl p-methoxycinnamate (EPMC) (1) is found as a major natural ester in the rhizome of Kaempferia galanga (kencur) and has been known to have various pharmacological activities. The previous study has reported the synthesis of N,N-bis-(2-hydroxyethyl)-p-methoxycinnamamide (2) by using microwave-assisted direct amidation of EPMC (1) with diethanolamine. In this research, we attempt to synthesize of 2 by using a conventional direct amidation of EPMC (1) with diethanolamine. The reaction was conducted without adding any coupling reagents or catalyst. Structure of the synthetic product was determined by using analysis of GC-MS, IR, and 1H-NMR spectroscopic data and then compared to the previously reported.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7300

Microwave-Assisted Claisen-Schmidt Condensation Reaction of Ethyl p-methoxycinnamate to Synthesize p-Methoxystyryl Ketone Derivatives and Evaluate Anti-inflammatory Activity of Synthetic Products Ismiarni Komala; Supandi Supandi; Nurmeilis Nurmeilis; Yardi Yardi; Ofa Suzanti Betha; Nurkhyati Putri Indriyani; Moethia Moethia; Muhamad Beny Setiawan; Ghilman Dharmawan; Putri Hayati Nufus; Noni Tri Utami
Journal of Mathematical and Fundamental Sciences Vol. 53 No. 1 (2021)
Publisher : Institute for Research and Community Services (LPPM) ITB

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.5614/j.math.fund.sci.2021.53.1.6

The rhizome of Kaempferia galanga has been known to contain ethyl p-methoxycinnamate (EPMC) (1) as a main component, which has anti-inflammatory properties. Previously we have reported the structural modification of EPMC (1) to form another ester, nitrostyrene, and cinnammamide derivatives and then studied their structure-activity relationships as anti-inflammatory agent. In continuing our research, in this paper, we report the microwave-assisted Claisen-Schmidt condensation of EPMC (1) to synthesize a series of p-methoxystyryl ketones followed by a study of their anti-inflammatory activity. The reaction begins with microwave-assisted cleavage oxidation of hydrolyzed product of EPMC, p-methoxycinnamic acid (2) with Ca(NO3)2 for the synthesis of p-methoxybenzaldehyde (3). Furthermore, 3 was reacted with acetophenone, ethyl methyl ketone and acetone via microwave-assisted Claisen-Schmidt condensation for the synthesis of (E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one (5a) (E)-1-(4-methoxyphenyl)pent-1-en-3-one (5b) and (E)-4-(4-methoxyphenyl)but-3-en-2-one (5c), respectively. The reaction products were characterized using spectroscopic techniques and were then tested for anti-inflammatory activity using in vitro anti-denaturation of protein assay. It was found that converting EPMC (1) to 5a and 5b reduced anti-inflammatory activity, while 5c retained anti-denaturation activity with an IC50 of 72.8 µg/ml.

Structure-Activity Relationship Study on the Ethyl p-Methoxycinnamate as an Anti-Inflammatory Agent Ismiarni Komala; Supandi Supandi; Nurhasni Nurhasni; Ofa Suzanti Betha; Eka Putri; Syarifatul Mufidah; Muhammad Fikry Awaludin; Mida Fahmi; Muhammad Reza; Nurkhayati Putri Indriyani
Indonesian Journal of Chemistry Vol 18, No 1 (2018)
Publisher : Universitas Gadjah Mada

Ethyl p-methoxycinnamate (EPMC) (1) has been isolated as a major compound from the rhizome of Kaempferia galanga together with the other compound ethyl cinnamate (2). As reported in the literature, EPMC (1) exhibited a significant in vitro and in vivo anti-inflammatory activity. In this research, we investigated the anti-inflammatory activity of compounds 1 and 2 by using anti-denaturation of heat bovine serum albumin (BSA) method. In order to analyze active sites that are responsible for the anti-inflammatory activity, therefore, it is necessary to conduct structural modification of EPMC (1). The structural modification was performed through re-esterification reaction by using conventional and assistance of the unmodified microwave oven. Evaluation of the results of the bioassay indicated that the ester and methoxy functional groups of EPMC (1) play an important role for the anti-inflammatory activity.

Cytotoxic Activity of the Indonesian Fern Angiopteris angustifolia C. Presl and Liverwort Mastigophora diclados (Birs. ex Web) Nees Against Breast Cancer Cell Lines (MCF-7) Ismiarni Komala; Stevani Sitorus; Fitri Ratna Dewi; Nurmeilis Nurmeilis; Laifa Annisa Hendarmin
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 8, No. 1, May 2022
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v8i1.22645

Breast cancer is the most frequent cancer among women worldwide, and it is also the main cause of death from cancer. Fern Angiopteris angustifolia C. Presl and Liverwort Mastigophora diclados (Birs.ex Web) Nees are the plants that grow in Indonesia that are limited explored for their phytochemical and biological activity. This study aims to evaluate the cytotoxic effect of ethanolic extracts leaves of A. angustifolia and M. diclados against breast cancer cell lines (MCF-7). The MTT assay was used to determine cytotoxic activity, which revealed that the ethanol extract of A. Angustifolia and M. diclados exhibited cytotoxic activity with an IC50 value of 121.8 ± 13.3 and 29.2 ±1.4 µg /mL, respectively.

Pengembangan dan Evaluasi Stabilitas Formulasi Gel yang Mengandung Etil p-metoksisinamat Nelly Suryani; Deani Nurul Mubarika; Ismiarni Komala
Pharmaceutical and Biomedical Sciences Journal (PBSJ) Vol 1, No 1 (2019)
Publisher : UIN Syarif Hidayatullah Jakarta

Etil p-metoksisinamat (EPMS) merupakan senyawa utama aktif anti-inflamasi yang terdapat dalam rimpang kencur (Kaempferia galanga). Tujuan penelitian ini adalah untuk mengembangkan sediaan gel yang mengandung EPMS dengan menggunakan kombinasi HPMC dan karbopol 940 sebagai gelling agent. Sediaan gel di buat dalam tiga formula F1, F2 dan F3 dengan variasi persentase kombinasi HPMC : karbopol 940 yang digunakan masing-masingnya adalah 0,4 : 0,4%, 0,5 : 0,5%, dan 1.0 : 0,5%. Masing-masing formula selanjutnya dievaluasi sifat fisik dan kimianya. Hasil evaluasi fisik menunjukkan bahwa secara organoleptis ketiga formula F1, F2 dan F3 memenuhi syarat sediaan gel, serta stabil ketika dilakukan pengujian sentrifugasi dan cycling test. Formuala F2 merupakan sediaan terbaik dalam pembuatan sediaan gel EPMS. Evaluasi stabilitas kimia menunjukkan bahwa kadar EPMS dalam sediaan gel hari ke- 0, 7, 14, dan 21 berada dalam rentang 91–100%. Sediaan gel mengalami penurunan kadar EPMS masing-masingnya sebesar 9% (F1), 5% (F2) dan 6%, (F3).

Optimization of Reaction Condition for Synthesis of 4-Methoxychalcone from Ethyl p-methoxycinnamate Ismiarni Komala; Muhamad Beny Setiawan; Yardi Yardi
Pharmaceutical and Biomedical Sciences Journal (PBSJ) Vol 4, No 2 (2022)
Publisher : UIN Syarif Hidayatullah Jakarta

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/pbsj.v4i2.30028

Ethyl p-methoxycinnamate (1) is the main secondary metabolite found in Kaempferia galanga Linn and has various interesting pharmacological activities, including anti-inflammatory, sedative, vasorelaxant, and antiangiogenic activities. This study aimed to optimize the conditions for the conversion of 1 to 4-methoxychalcone (2) using a conventional synthetic reaction. The conversion was initiated by the hydrolysis of 1 to p-methoxycinnamic acid (3) and 3 to 4-methoxybenzaldehyde (4), and continued with the Claisen-Schmidt reaction of 4 with acetophenone (5). The temperature (room temperature and 45 °C) and ratio of 4 to 5 (1:1 and 1:2) were varied to determine the optimal conditions for the reaction. The results suggested that the reaction of 4 with 5 gave the best yield (42.1 %) when conducted at room temperature in a ratio of 4 to 5 (1:1). The structure of the reaction product was elucidated by spectroscopic analysis and compared with previously published data

Optimization of Reaction Condition for Synthesis of 4-Methoxychalcone from Ethyl p-methoxycinnamate Ismiarni Komala; Muhamad Beny Setiawan; Yardi Yardi
Pharmaceutical and Biomedical Sciences Journal (PBSJ) Vol 4, No 2 (2022)
Publisher : UIN Syarif Hidayatullah Jakarta

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/pbsj.v4i2.30028

Ethyl p-methoxycinnamate (1) is the main secondary metabolite found in Kaempferia galanga Linn and has various interesting pharmacological activities, including anti-inflammatory, sedative, vasorelaxant, and antiangiogenic activities. This study aimed to optimize the conditions for the conversion of 1 to 4-methoxychalcone (2) using a conventional synthetic reaction. The conversion was initiated by the hydrolysis of 1 to p-methoxycinnamic acid (3) and 3 to 4-methoxybenzaldehyde (4), and continued with the Claisen-Schmidt reaction of 4 with acetophenone (5). The temperature (room temperature and 45 °C) and ratio of 4 to 5 (1:1 and 1:2) were varied to determine the optimal conditions for the reaction. The results suggested that the reaction of 4 with 5 gave the best yield (42.1 %) when conducted at room temperature in a ratio of 4 to 5 (1:1). The structure of the reaction product was elucidated by spectroscopic analysis and compared with previously published data

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