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Sintesis, Karakterisasi Struktur, dan Kajian Molecular Docking Senyawa Turunan 4’-Metoksi Flavonol sebagai Antagonis Reseptor Estrogen Alpha (ER-a) pada Kanker Payudara Ihsan Ikhtiarudin; Rahma Dona; Neni Frimayanti; Rahayu Utami; Nurul Susianti; Abdi Wira Septama
Jurnal Riset Kimia Vol. 13 No. 2 (2022): September
Publisher : Universitas Andalas

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.25077/jrk.v13i2.553

Abstract

A long period of drug administration in breast cancer chemotherapy can cause various side effects. These situations encourage researchers to search for and develop alternative anticancer drugs through various approaches. This study aimed to synthesize a flavonol derivative (TF4) and to study the interactions of the synthesized compound with ER-α as one of the targeted receptors in breast cancer treatment. The synthesis was carried out using the stirring method and the study of interactions of TF4 with ER-α was performed through molecular docking against ER-α crystal structures bound to an antagonist (PDB ID: 3ERT) and agonist (PDB ID: 1A52). The synthesis of TF4 produced crude product in 58 % yield and pure product in 6 % yield. The structure of TF4 was confirmed by spectroscopic analyses including UV, FT-IR, 1D, and 2D NMR. The docking results showed that the TF4 does not form any conventional hydrogen bond with ER-α. However, it can form carbon-hydrogen (C--H) bonds and van der Walls interactions with several important residues on the active site of ER-α. In addition, the binding free energy values of TF4 (-9.14 and -9.50 kcal/mol) are more negative than estradiol (E2) as one of the natural ligands for ER-α. Thus, it can be estimated that TF4 can be bounded easier on the active site of ER-α than its natural ligand. It may presume that it can act as an estrogen antagonist because of the similarity in interactions and binding poses compared to TAM, TOR, dan 4-OHT as reference drug molecules.
Sintesis Dan Studi Molecular Docking Senyawa Pirazolo-Piridin Turunan Analog Kurkumin Monoketon Sebagai Inhibitor Enzim COX-2 Enda Mora; Adel Zamri; Hilwan Y. Teruna; Neni Frimayanti; Ihsan Ikhtiarudin; Putri Rizki Rahmadani; Vella kurnia Wahyuni
Jurnal Penelitian Dan Pengkajian Ilmiah Eksakta Vol 1 No 2 (2022): Jurnal Hasi Penelitian Dan Pengkajian Ilmiah Eksakta - JPPIE
Publisher : LPPM Universitas Dharma Andalas

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.47233/jppie.v2i1.799

Abstract

The new pyrazolo-pyridine compounds derived from monoketone curcumin analogues (P4Cl and P2CL) were synthesized in two stages. The first stage was the synthesis of curcumin monoketone (Cs) analogue through the Claisen-Schmidt reaction in the heating method using reflux. The second step was the synthesis of P2CL and P4Cl through nucleophilic addition and intramolecular cyclization in the heating method using a Monowave 50 apparatus. The structures of the compounds P2CL and P4Cl were confirmed by spectroscopic analysis including UV-Vis, FT-IR, 1H-NMR and HRMS. Based on molecular docking studies, the compounds P2Cl and P4Cl have weak potential as COX-2 enzyme inhibitors with a binding free energy value of -4.02 kcal/mol and an RMSD of 1.19.
FORMULASI DAN UJI AKTIVITAS TABIR SURYA SEDIAAN KRIM EKSTRAK ETANOL DAUN MARPUYAN (Rhodamnia cinerea Jack): FORMULATION AND SUNSCREEN ACTIVITY OF CREAM CONTAINING MARPUYAN LEAVES (Rhodamnia cinerea Jack) EXTRACT ETHANOL Musyirna Rahmah Nst; Deni Anggraini; Gressy Novita; Mustika Furi; Ihsan Ihtiarudin
Medical Sains : Jurnal Ilmiah Kefarmasian Vol 8 No 2 (2023)
Publisher : Sekolah Tinggi Farmasi Muhammadiyah Cirebon

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.37874/ms.v8i2.778

Abstract

Sinar matahari memiliki manfaat bagi kesehatan. Sering terpapar sinar matahari menyebabkan kulit kemerahan, peradangan, dan menyebabkan terjadinya kanker kulit. Salah satu cara untuk melindungi kulit dari sinar matahari yaitu dengan menggunakan tabir surya. Daun marpuyan (Rhodamnia cinerea Jack) mempunyai kandungan flavonoid total dan fenolik total yang tinggi serta memiliki aktivitas antioksidan yang sangat kuat sehingga dapat digunakan sebagai bahan aktif alami krim tabir surya. Tujuan penelitian ini adalah memformulasi dan mengevaluasi krim tabir surya ekstrak etanol daun marpuyan (Rhodamnia cinerea Jack) serta mengetahui nilai persen transmisi eritema (%Te), persen transmisi pigmentasi (%Tp), dan nilai Sun Protection Factor (SPF). Dibuat empat formula dengan variasi konsentrasi ekstrak etanol daun marpuyan dalam krim yaitu, F0 (0%), F1 (0,1% b/b), F2 (0,5% b/b), dan F3 (1% b/b). Hasil menunjukkan nilai SPF F0, F1, F2, dan F3 berturut-turut 1,05; 4,68 (proteksi sedang); 4,74 (proteksi sedang); dan 9,36 (proteksi maksimal). Nilai SPF antar formula berbeda signifikan yang mana konsentrasi ekstrak berbanding lurus dengan nilai SPF. Kata kunci : Tabir surya, daun marpuyan, formulasi, Sun Protection Factor (SPF)
PENENTUAN TOTAL FENOLIK, FLAVONOID DAN UJI AKTIVITAS ANTIOKSIDAN EKSTRAK DAN FRAKSI DAUN KEDABU (Sonneratia ovata Backer) Mustika Furi; Nursinta Al Basit; Ihsan Ikhtiarudin; Rahayu Utami
JFIOnline | Print ISSN 1412-1107 | e-ISSN 2355-696X Vol. 12 No. 1 (2020): Jurnal Farmasi Indonesia
Publisher : Pengurus Pusat Ikatan Apoteker Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (363.827 KB) | DOI: 10.35617/jfionline.v12i1.56

Abstract

Kedabu (Sonneratia ovata Backer) is plant that belongs to family Lytheraceae which has been used as traditional medicine. Determination of total phenolic and total flavonoid content as well as antioxidant activity of extract and fractions of its leaves have been conducted by colorimetric method using photometric measurements. The Folin Ciocalteu and gallic acid was used as reagent and standard for total phenolic determination, meanwhile AlCl3 and quercetin was prepared for total flavonoid content test. Antioxidant activity assay was performed using DPPH free radical scavenging method. Based on the result, it showed that ethyl acetate fraction afforded the highest total phenolic and total flavonoid content with values of 232 mgGAE/g and 180 mgQE/g, respectively. As for the antioxidant activity, the ethyl acetate fractions also demonstrated the most potential activity among others fraction and extract with IC50 value of 12,47 µg/mL.
SINTESIS DAN STUDI MOLECULAR DOCKING SENYAWA PIRAZOLO-PIRIDIN TERSUBSTITUSI METOKSI TURUNAN KURKUMIN MONOKARBONIL SEBAGAI INHIBITOR ENZIM SIKLOOKSIGENASE-2 Enda Mora; Adel Zamri; Hilwan Yuda Teruna; Neni Frimayanti; Ihsan Ikhtiarudin; Shafira Melsonia
Jurnal Penelitian Farmasi Indonesia Vol 12 No 1 (2023): JPFI
Publisher : Pusat Penelitian dan Pengabdian Masyarakat (P3M) Sekolah Tinggi Ilmu Farmasi Riau

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.51887/jpfi.v12i1.1763

Abstract

Scaffold pirazol maupun piazolo-piridin telah dilaporkan memiliki potensi aktivitas biologis yang menarik dan terdapat pada berbagai struktur senyawa obat yang telah disetujui oleh food and drug administration (FDA). Pada penelitian ini, senyawa pirazolo-piridin tersubstitusi metoksi sebagai turunan dari analog kurkumin monokarbonil telah disintesis melalui dua tahap reaksi. Tahap pertama adalah sintesis analog kurkumin monokarbonil tersubsitusi metoksi melalui reaksi kondensasi Claisen-Schmidt dengan bantuan iradiasi microwave. Tahap kedua adalah sintesis senyawa pirazolo-piridin melalui reaksi adisi nukleofilik yang diikuti oleh reaksi siklisasi intramolekular dalam reaktor tertutup, monowave 50. Kemurnian produk hasil sintesis telah dipastikan melalui analisis HPLC. Struktur senyawa pyrazolo-piridin telah dikonfirmasi melalui analisis spektroskopi UV-Vis, FT-IR, dan 1H-NMR. Berdasarkan studi molecular docking, senyawa tersebut  tidak menunjukkan potensi aktivitas yang baik sebagai inhibitor enzim siklooksigenase-2 (COX-2), karena hanya memiliki nilai energi bebas pengikatan sebesar -5,98 kcal/mol. Selain itu, pirazolo piridin tersubstitusi metoksi juga tidak dapat membentuk satupun ikatan hidrogen dengan sisi aktif COX-2. Di sisi lain, celecoxib sebagai kontrol positif memiliki energi bebas pengikatan sebesar -11,97 kcal/mol dan dapat membentuk ikatan hidrogen dengan residu asam amino Gln178, Leu338, Arg499, dan Phe504 pada sisi aktif COX-2 (PDB ID: 3LN1). Pyrazol and pyrazolopyridine scaffolds have been reported to have many interesting biological activities and present in various structures of drug compounds that have been approved by the food and drug administration (FDA). In this study, a methoxy-substituted pyrazolo-pyridine compound as derivative of monocarbonyl curcumin analogs was synthesized in two steps of reaction. The first step was the synthesis of monocarbonyl curcumin analog through the Claisen-Schmidt condensation with the assist of microwave irradiation. The second step is the synthesis of pyrazolopyridine through nucleophilic addition followed by intramolecular cyclization in a closed-vessel reactor, monowave 50. The purity of synthesized product was confirmed by HPLC analysis, and the structure has been confirmed through UV-Vis, FT-IR, and 1H NMR spectroscopic analyses. Based on the molecular docking study, the pyrazolo-pyridine did not show good activity as cyclooxygenase-2 (COX-2) inhibitor, because it only has a binding free energy of -5.98 kcal/mol. In addition, methoxy-substituted pyrazolo-pyridin also can not form any hydrogen bonds with the active site of COX-2. On the other hand, celecoxib as a positive control has a binding free energy of -11.97 kcal/mol and can form hydrogen bonds with Gln178, Leu338, Arg499, and Phe504 amino acid residues on the active site of COX-2 (PDB ID: 3LN1).
Cytotoxic Activity of Ethyl Acetate Extract from Voacanga foetida (Bl.) Rolfe Leaves Against T47D Breast Cancer Cells Adriani Susanty; Mira Febrina; Dian Sanita Putri; Ihsan Ikhtiarudin; Fatma Sri Wahyuni; Dachriyanus Dachriyanus
Borneo Journal of Pharmacy Vol. 6 No. 1 (2023): Borneo Journal of Pharmacy
Publisher : Institute for Research and Community Services Universitas Muhammadiyah Palangkaraya

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.33084/bjop.v6i1.3499

Abstract

The cytotoxicity of ethyl acetate extract from Tampa badak (Voacanga foetida (Bl.) Rolfe) leaves against Artemia salina leach larvae was determined using the brine shrimp lethality test (BSLT) method and was evaluated against T47D breast cancer cells using MTT assay method. The result of BSLT showed a consistent result with MTT assay, which is the result obtained that ethyl acetate extract is very toxic against A. salina Leach larvae with LC50 value of 8.61 µg/mL and very cytotoxic against T47D breast cancer cells with IC50 values of 0.87; 0.66; and 0.95 µg/mL at the 24, 48 and 72 hours of incubation times, respectively. The MTT assay data were analyzed using a two-way ANOVA statistical method to see the effect of the dependent variable (concentration and time) on the independent variable (% viability). Based on the statistical test result, there is a difference in % viability between concentrations of 0.1; 1; and 10 µg/mL (p <0.05), but the length of incubation does not affect % viability (p >0.05).
FORMULASI DAN UJI AKTIVITAS TABIR SURYA SEDIAAN KRIM EKSTRAK ETANOL DAUN MARPUYAN (Rhodamnia cinerea Jack): FORMULATION AND SUNSCREEN ACTIVITY OF CREAM CONTAINING MARPUYAN LEAVES (Rhodamnia cinerea Jack) EXTRACT ETHANOL Musyirna Rahmah Nst; Deni Anggraini; Gressy Novita; Mustika Furi; Ihsan Ihtiarudin
Medical Sains : Jurnal Ilmiah Kefarmasian Vol 8 No 2 (2023)
Publisher : Sekolah Tinggi Farmasi Muhammadiyah Cirebon

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.37874/ms.v8i2.778

Abstract

Sinar matahari memiliki manfaat bagi kesehatan. Sering terpapar sinar matahari menyebabkan kulit kemerahan, peradangan, dan menyebabkan terjadinya kanker kulit. Salah satu cara untuk melindungi kulit dari sinar matahari yaitu dengan menggunakan tabir surya. Daun marpuyan (Rhodamnia cinerea Jack) mempunyai kandungan flavonoid total dan fenolik total yang tinggi serta memiliki aktivitas antioksidan yang sangat kuat sehingga dapat digunakan sebagai bahan aktif alami krim tabir surya. Tujuan penelitian ini adalah memformulasi dan mengevaluasi krim tabir surya ekstrak etanol daun marpuyan (Rhodamnia cinerea Jack) serta mengetahui nilai persen transmisi eritema (%Te), persen transmisi pigmentasi (%Tp), dan nilai Sun Protection Factor (SPF). Dibuat empat formula dengan variasi konsentrasi ekstrak etanol daun marpuyan dalam krim yaitu, F0 (0%), F1 (0,1% b/b), F2 (0,5% b/b), dan F3 (1% b/b). Hasil menunjukkan nilai SPF F0, F1, F2, dan F3 berturut-turut 1,05; 4,68 (proteksi sedang); 4,74 (proteksi sedang); dan 9,36 (proteksi maksimal). Nilai SPF antar formula berbeda signifikan yang mana konsentrasi ekstrak berbanding lurus dengan nilai SPF. Kata kunci : Tabir surya, daun marpuyan, formulasi, Sun Protection Factor (SPF)
Synthesis and Evaluation of Some Sulfonamide-Substituted of 1,3,5-Triphenyl Pyrazoline Derivatives as Tyrosinase Enzyme Inhibitors Herfindo, Nofal; Frimayanti, Neni; ikhtiarudin, Ihsan; eryanti, Yum; zamri, Adel
Molekul Vol 18 No 2 (2023)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2023.18.2.6936

Abstract

Pyrazoline is well-known as heterocycles compound that can exhibit many biological effects. In this work, we synthesized a series of sulfonamide-substituted 1,3,5-triphenyl pyrazoline compounds as a promising tyrosinase inhibitor agent. These compounds prepared by multicomponent reaction of corresponding aldehyde, ketone, and hydrazine using seal-vessel reactor. Pyrazolines compound were tested for their tyrosinase inhibitor activity through in vitro assay. The test result found that compound 4c, 4d, and 4e possessed better tyrosinase inhibitory activity compared to the reference drug, kojic acid. Compound 4c exhibited the strongest tyrosinase inhibitory effect with an IC50 value of 30.14 µM. The results suggested that hydroxyl and methoxy substituent at para position are preferable. Furthermore, molecular docking studies result match the pattern of in vitro assay where the compound will provide a stronger binding interaction and lower binding free energies.
Sintesis C-dots dari Gula Pasir dan Asam Sitrat untuk Deteksi Logam Berat Yanto, Yanto; Dona, Rahma; Ikhtiarudin, Ihsan
Photon: Jurnal Sain dan Kesehatan Vol. 14 No. 1 (2023): Jurnal Photon
Publisher : LPPM Universitas Muhammadiyah Riau

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.37859/jp.v14i1.4214

Abstract

Heavy metal contamination is one of the problems in pharmaceutical products. Carbon dots are a practical and economical method of heavy metal detection to reduce heavy metal contamination in pharmaceutical products. Carbon dots have been successfully synthesized by microwave irradiation from sugar table doped with urea fertilizer (CD-GU) and citric acid doped with urea fertilizer (CD-AU). The success of the synthesis of carbon dots can be seen from their properties that produce a blue to green luminescence when excited with a 405 nm laser and an orange to red luminescence when excited with a 532 nm laser. When excited with a 405 nm laser, CD-GU produces a strong light blue luminescence, while CD-AU produces a strong green luminescence. CD-GU and CD-AU also exhibit orange luminescence when excited with a 532 nm laser. The intensity of luminescence of carbon dots will decrease when interacting with heavy metals so that it can be applied for heavy metal detection. The results of this study revealed that CD-GU and CD-AU can be used to detect heavy metals.
Isolation and Cytotoxic Activity Test of Alkaloids from Dichloromethane Fraction of Bark of Tampa Badak (Voacanga foetida (Blume) Rolfe) Against T47D Cell Line Adriani Susanty; Nurdina Putri; Ihsan Ikhtiarudin; Novia Sinata; Dira Dira; Fatma Sri Wahyuni; Dachriyanus Dachriyanus
Journal of Tropical Pharmacy and Chemistry Vol. 7 No. 2 (2023): J. Trop. Pharm. Chem.
Publisher : Faculty of Pharmacy, Universitas Mulawarman, Samarinda, Indonesia, 75117, Gedung Administrasi Fakultas Farmasi Jl. Penajam, Kampus UNMUL Gunung Kelua, Samarinda, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.25026/jtpc.v7i2.583

Abstract

Cancer is a problem in the health sector because this disease has an increasing incidence of morbidity and mortality. While the treatment still leaves some drug side effects, which cause discomfort for cancers sufferers. The arises because most cancer drugs work non-selectively. Because of some of the problems above, it is necessary to encourage the search for alternative drugs treatment of cancer. Voacanga foetida (Blume) Rolfe (Apocynaceae) is a species of plant from the genus Voacanga known as the tampa badak from West Sumatra. This plant is known to be source of indole alkaloids and also bis-indole alkaloids potential as cancer drugs. Therefore, in this study we are interested to explore the potency of this plant as natural product sources with potential cytotoxic activity. The study was started from the isolation process and continued by characterization of the isolated compounds and then testing their cytotoxic activity T47D breast cancer cell line. The isolation process of alkaloid compounds were performed by acid-base extraction, liquid-liquid fractionation, and followed by separation using column chromatography. Then,the potency of cytotoxic activity of the isolates were screened through Brine Shrimp Lethality Test (BSLT) method and evaluated by MTT assay. The structure of three isolated alkaloids (VFB-DB1.1; VFB-DB2.1; and VFB-DB2.2) were charachterized using spectroscopic analyses, including UV and FT-IR. One isolated compound (VFB-DB1.1) was also characterized using 1H NMR spectroscopy. Based on the similarity of 1H NMR spectra of isolated compound when compared with the literature, compound VFB-DB1.1 was identified as voacangine. Then, the BSLT and MTT assay result showed that VFB-DB1.1 exhibited LC50 value of 15.8 µg/mL againt Artemia salina L.and IC50 value of 8.9 µg/mL against T47D breast cancer cells, respectively.