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REAKSI PENATAAN ULANG FRIES PADA EUGENIL ASETAT Kusmiyati, .; Matsjeh, Sabirin; Jumina, .
PHARMACIANA Vol 1, No 1: Mei 2011
Publisher : PHARMACIANA

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Telah dilakukan reaksi penataan ulang Fries pada eugenil asetat yang bertujuan untuk mengetahui pengaruh gugus allil yang terdapat dalam eugenil asetat. Reaksi penataan ulang Fries eugenil asetat dilakukan dengan pemanasan menggunakan katalis AlCl3, pelarut diklorometana pada temperatur 120 °C selama 3 jam. Identifikasi struktur hasil sintesis dilakukan dengan menggunakan Spektrometri inframerah (IR) dan GC-MS. Hasil penelitian ini menunjukkan bahwa reaksi penataan ulang Fries pada eugenil asetat tidak terjadi, namun membentuk dimer eugenil asetat yang berupa cairan kental coklat kehitaman.

SINTESIS TURUNAN ASETOFENON DARI 1-(4-ASETOKSIFENIL-3-METOKSI)-2-PROPANIL FORMAT Kusmiyati, .; Matsjeh, Sabirin; Jumina, .
PHARMACIANA Vol 2, No 1: Mei 2012
Publisher : PHARMACIANA

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Telah dilakukan sintesis senyawa turunan Asetofenon dari 1-(4-asetoksifenil-3-metoksi)-2-propanil format melalui reaksi penataan ulang Fries yang bertujuan untuk menghasilkan senyawa turunan orto hidroksi asetofenon sebagai bahan dasar sintesis senyawa Flavonoid. Reaksi penataan ulang Fries 1-(4-asetoksifenil-3-metoksi)-2-propanil format dilakukan dengan pemanasan menggunakan katalis AlCl3, pelarut diklorometana pada temperatur 120 °C selama 3 jam. Identifikasi struktur senyawa hasil sintesis dilakukan dengan menggunakan spektrofotometri Infra Merah (IR) dan GC-MS. Penataan ulang Fries tehadap 1-(4-asetoksifenil-3-metoksi)-2-propanil format menghasilkan 1-(2-hidroksi-3 -metoksi-5-propenil)-asetofenon dengan hasil samping 1-(2-hidroksi-3-metoksi- 5-propanil)-asetofenon, masing-masing rendemennya sebesar 43,26% dan 9,84%.

GREEN REDUKSI P- ANISALDEHIDA DAN VANILIN Firdaus, Maulidan; Jumina, Jumina; Anwar, Chairil; Lerrick, Reinner I
Alchemy Jurnal Penelitian Kimia Vol 7, No 1 (2008)
Publisher : Alchemy Jurnal Penelitian Kimia

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Sintesis menggunakan prosedur sederhana, efisien energi, dan relatif cepat untuk mereduksiÂ p-anisaldehida dan vanilin berdasarkan prinsip - prinsipÂ green chemistryÂ telah dilakukan. reduksiÂ p-anisaldehida dilakukan dengan cara penggerusanÂ p-anisaldehida dan NaBH4Â dengan jumlah mol yang sama pada pemperatur kamar tanpa pelarut. reduksi vanilin dilakukan dengan NaBH4Â pada temperatur kamar dengan sejumlah kecil pelarut metanol menggunakan mortar dan pestel. penentuan struktur produk reaksi dilakukan dengan metode spektroskopi (IR,Â 1H-NMR, dan GC-MS). pada penelitian ini, reduksiÂ p-anisaldehida dan vanilin menghasilkan 4-metoksibenzil alkohol dan 4-hidroksi-3-metoksibenzil alkohol dngan rendemen berturut-turut sebesar 98% dan 89%.

ISOLASI, IDENTIFIKASI, DAN ELUSIDASI STRUKTUR SENYAWA ALKALOID DALAM EKSTRAK METANOL-ASAM NITRAT DARI BIJI MAHONI BEBAS MINYAK (Swietenia macrophylla, King) Mursiti, S; Matsjeh, S; -, Jumina; -, Mustofa
Jurnal MIPA Vol 36, No 2 (2013): October 2013
Publisher : Jurnal MIPA

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Abstrak __________________________________________________________________________________________ Telah dilakukan penelitian tentang isolasi, identifikasi, dan elusidasi strukturÂ senyawa alkaloid dalam ekstrak metanol-asam nitrat dari biji mahoni bebas minyak (Swietenia macrophylla King). Biji mahoni diambil minyaknya dengan cara ekstraksi soxhlet menggunakan pelarut petroleum eter selama 8 jam. Isolasi senyawa alkaloid menggunakan metanol dan larutan asam nitrat 10%. Sebanyak satu gram ampas biji mahoni bebas minyak dicampur dengan 1 mL larutan asam nitrat 10%, kemudian ditambah 5 mL metanol dalam erlenmeyer bertutup disertai pengocokan selama 5 menit pada suhu 60oC menggunakan penangas air, setelah itu disaring, ditambah 1 mL larutan amonia 10%, kemudian disaring, dan dipekatkan. Ekstrak kemudian dianalisis dengan KLT, kemudian dipisahkan dengan kromatografi kolom. Sebagai penyerap pada kolom digunakan silika gel 40, panjang kolom 27 cm, diameter 2,8 cm, eluen yang digunakanÂ adalah kloroform:metanol (95:5), dan jumlah tetesan 15-20Â per menit. Setiap fraksi yang diperoleh dari kromatografi kolom dianalisis dengan KLT menggunakan lampu UV. Uji alkaloid menggunakan pereaksi Dragendorff 130 dan 132. Fraksi yang positif merupakan fraksi yang mengandung alkaloid. Kemudian fraksi ini dianalisis lebih lanjut untuk identifikasi struktur dengan GC, spektrometer IR, UV, dan 1HNMR. Hasil analisis menunjukkan bahwa dalam ekstrak diperkirakan terdapat senyawa alkaloid yakni 3,4,5-trietil-6-metoksi-2-metil-1,2-dihidro-piridin. Â Abstract __________________________________________________________________________________________ It has been conducted a research on the isolation, identification and structural elucidation of alkaloid compounds in methanol-nitric acid extract of the oil-free mahogany seeds (Swietenia macrophylla, King). The oil was taken from mahogany seed by Soxhlet extraction and using petroleum ether solvent for 8 hours, while the isolation of alkaloid compound used methanol and 10 % nitric acid solution. A gram of oil-free mahogany slag was mixed with 1 mL of 10 % nitric acid solution, then it was added with 5 mL of methanol in a cap erlenmeyer and stirred for 5 min at 60 Â°C by using water bath, after that it was filtered and added by 1 mL of 10 % ammonia solution, then it was filtered and concentrated. The extract was analyzed by TLC and separated by column chromatography. As absorbent, it used silica gel column 40 with length of 27 cm, diameter 2.8 cm, while the eluent that was used was chloroform : methanol (95:5), and the number of droplets was 15-20 per minute. Each fraction obtained from column chromatography was analyzed by TLC using UV light. While, alkaloids test was analyzed by using Dragendorff reagent 130 and 132. Positive fraction is the fraction containing alkaloids, then this fraction was analyzed further more to identify the structure by using GC, IR spectrometer, UV and 1HNMR. The analysis showed that the extract was estimated that there are alkaloid compounds consisting of 3,4,5-triethyl-6-methoxy-2-methyl-1,2-dihydro-pyridine.

UJI AKTIVITAS PENGHAMBATAN POLIMERISASI HEME (1)-N-(2-NITROBENZIL)-1,10- FENANTROLINIUM IODIDA DAN (1)-N-(4-NITROBENZIL)-1,10- FENANTROLINIUM IODIDA SECARA IN VITRO Nurani, Laela Hayu; Utami, Dwi; Widyaningsih, Wahyu; Narwanti, Iin; Nurwening, Eti; Jumina, Jumina
Pharmaciana Vol 4, No 2 (2014): Pharmaciana
Publisher : Universitas Ahmad Dahlan

The inhibitory activity of heme polymerization of (1)-N-(2-nitrobenzyl)-1,10- phenantrolinium iodide and (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide have been done. This study aims to analyse the (1)-N-(2-nitrobenzyl)-1,10-phenantrolinium iodide and (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide as inhibitory of polimerization heme. Analysis of heme inhibtory polimerization activity used the experimental in vitro method. The activity showed by IC50 (the capable concentration of extract to inhibiting polymerization heme by 50% ). The IC50 value acquired by probit analysis. Assess IC50 of (1)-N-(2-nitrobenzyl)- 1,10-phenantrolinium iodide not to be identified, (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide and chloroquine by successively are 0,571Â±0,071; 25,498Â±1,876 mg/mL. The result showed the (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide had the highest value of the heme polymerization inhibitory activity than chloroquin, (1)-N-(2-nitrobenzyl)-1,10- phenantrolinium iodide hadnât the heme polymerization inhibitory activity.

REAKSI PENATAAN ULANG FRIES PADA EUGENIL ASETAT kusmiyati, kusmiyati; Matsjeh, Sabirin; Jumina, Jumina
Pharmaciana Vol 1, No 1 (2011): Pharmaciana
Publisher : Universitas Ahmad Dahlan

Fries Rearrangement of eugenyl acetate in order to study allilic substituentgroup influence has been done. Fries rearrangement of eugenyl acetate was done byheating at 120Â°C for 3 hours under AlCl3, dichloromethane as the catalyst and solvent,respectively. The structure of the compound was identified using Infra Redspectrometry (IR) and GC-MS. The result of te research showed that rearrangementfries of eugenyl acetate are not formed, but yielded lightly brown oil of dimmer.

SINTESIS TURUNAN ASETOFENON DARI 1-(4-ASETOKSIFENIL-3-METOKSI)-2-PROPANIL FORMAT Kusmiyati, Kusmiyati; Matsjeh, Sabirin; Jumina, Jumina
Pharmaciana Vol 2, No 1 (2012): Pharmaciana
Publisher : Universitas Ahmad Dahlan

The Synthesis of acetophenone derivative from 1-(4-acetoxyphenyl-3-methoxy)-2-propanyl formate through Fries Rearrangement in order to produceortho hidroxy acetophenone derivative as starting material of Flavanoid compound hasbeen done. The reaction of 1-(4-acetoxyphenyl-3-methoxy)-2-propanyl formate wasdone by heating at 120 Â°C for 3 hours under AlCl3, dichloromethane as the catalyst andsolvent, respectively. The structure of the compound was identified using Infra Redspectrometry (IR) dan GC-MS. Fries rearrangement of 1-(4-acetoxyphenil-3-methoxy)-2-propanyl formate produce 1-(2-hyidroxy-3-methoxy-5-propenyl)-acetophenone and 1-(2-hyidroxy-3-methoxy-5-propanyl)-acetophenone as sideproduct with product rendemen were 43.26% and 9.48%, respectively.

ISOLASI, IDENTIFIKASI, DAN ELUSIDASI STRUKTUR SENYAWA ALKALOID DALAM EKSTRAK METANOL-ASAM NITRAT DARI BIJI MAHONI BEBAS MINYAK (Swietenia macrophylla, King) Mursiti, S; Matsjeh, S; -, Jumina; -, Mustofa
Indonesian Journal of Mathematics and Natural Sciences Vol 36, No 2 (2013): October 2013
Publisher : Universitas Negeri Semarang

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Abstrak __________________________________________________________________________________________ Telah dilakukan penelitian tentang isolasi, identifikasi, dan elusidasi strukturÂ senyawa alkaloid dalam ekstrak metanol-asam nitrat dari biji mahoni bebas minyak (Swietenia macrophylla King). Biji mahoni diambil minyaknya dengan cara ekstraksi soxhlet menggunakan pelarut petroleum eter selama 8 jam. Isolasi senyawa alkaloid menggunakan metanol dan larutan asam nitrat 10%. Sebanyak satu gram ampas biji mahoni bebas minyak dicampur dengan 1 mL larutan asam nitrat 10%, kemudian ditambah 5 mL metanol dalam erlenmeyer bertutup disertai pengocokan selama 5 menit pada suhu 60oC menggunakan penangas air, setelah itu disaring, ditambah 1 mL larutan amonia 10%, kemudian disaring, dan dipekatkan. Ekstrak kemudian dianalisis dengan KLT, kemudian dipisahkan dengan kromatografi kolom. Sebagai penyerap pada kolom digunakan silika gel 40, panjang kolom 27 cm, diameter 2,8 cm, eluen yang digunakanÂ adalah kloroform:metanol (95:5), dan jumlah tetesan 15-20Â per menit. Setiap fraksi yang diperoleh dari kromatografi kolom dianalisis dengan KLT menggunakan lampu UV. Uji alkaloid menggunakan pereaksi Dragendorff 130 dan 132. Fraksi yang positif merupakan fraksi yang mengandung alkaloid. Kemudian fraksi ini dianalisis lebih lanjut untuk identifikasi struktur dengan GC, spektrometer IR, UV, dan 1HNMR. Hasil analisis menunjukkan bahwa dalam ekstrak diperkirakan terdapat senyawa alkaloid yakni 3,4,5-trietil-6-metoksi-2-metil-1,2-dihidro-piridin. Â Abstract __________________________________________________________________________________________ It has been conducted a research on the isolation, identification and structural elucidation of alkaloid compounds in methanol-nitric acid extract of the oil-free mahogany seeds (Swietenia macrophylla, King). The oil was taken from mahogany seed by Soxhlet extraction and using petroleum ether solvent for 8 hours, while the isolation of alkaloid compound used methanol and 10 % nitric acid solution. A gram of oil-free mahogany slag was mixed with 1 mL of 10 % nitric acid solution, then it was added with 5 mL of methanol in a cap erlenmeyer and stirred for 5 min at 60 Â°C by using water bath, after that it was filtered and added by 1 mL of 10 % ammonia solution, then it was filtered and concentrated. The extract was analyzed by TLC and separated by column chromatography. As absorbent, it used silica gel column 40 with length of 27 cm, diameter 2.8 cm, while the eluent that was used was chloroform : methanol (95:5), and the number of droplets was 15-20 per minute. Each fraction obtained from column chromatography was analyzed by TLC using UV light. While, alkaloids test was analyzed by using Dragendorff reagent 130 and 132. Positive fraction is the fraction containing alkaloids, then this fraction was analyzed further more to identify the structure by using GC, IR spectrometer, UV and 1HNMR. The analysis showed that the extract was estimated that there are alkaloid compounds consisting of 3,4,5-triethyl-6-methoxy-2-methyl-1,2-dihydro-pyridine.

Synthesis of 1-(4-Ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium Bromide and Its Evaluation as Antiplasmodium through Heme Polymerization Inhibitory Activity (HPIA) Assay Fitriastuti, Dhina; Alfiyah, Viny; Mustofa, Mustofa; Jumina, Jumina; Mardjan, Muhammad Idham Darussalam
Makara Journal of Science Vol. 25, No. 1
Publisher : UI Scholars Hub

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This study describes the development of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent. The salt, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, was prepared using vanillin as the starting material in four simple synthetic steps. First, the alkylation of vanillin using diethyl sulfate produced 4-ethoxy-3-methoxybenzaldehyde in 79% yield. Second, the reduction of the protected vanillin by NaBH4 through the grinding method allowed us to obtain 4-ethoxy-3-methoxybenzyl alcohol in 96% yield. Next, the bromination of the benzyl alcohol under solvent-free condition led to the formation of the corresponding benzyl bromide, which in turn underwent bimolecular nucleophilic substitution with 1,10-phenanthroline to produce the desired product, that is, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide, in 58% yield. The evaluation of N-benzyl-1,10-phenantrolinium salt as an antiplasmodium agent was conducted through heme polymerization inhibitory activity (HPIA) assay. The results showed that the phenantroline salt and chloroquine displayed the HPIA half maximal inhibitory concentrations of 3.63 and 4.37 mM, respectively. Therefore, 1-(4-ethoxy-3-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide displays desirable HPIA and has a great potential to be further developed as an antiplasmodium.

Synthesis, Biological Activity, and Molecular Docking Study of Xanthenol and Its Disproportionation Products as Anticancer and Antimalarial Agents Pratama, Ardhya Ayu; Jumina, Jumina; Anwar, Chairil
Makara Journal of Science Vol. 28, No. 2
Publisher : UI Scholars Hub

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Xanthone and its derivatives are well known for their broad biological activities. This research aims to investigate the anticancer and antimalarial activities of synthesized xanthenol and xanthene compounds and to elucidate their mechanisms of action through molecular docking. The xanthenol compound was obtained through xanthone reduction with sodium triacetoxyborohydride, and xanthene synthesis was studied through three different reaction conditions: uncatalyzed and catalyzed by Lewis acid or Bronsted acid. The reduction reaction produced xanthenol in 30.50% yield, whereas the three reaction conditions produced xanthene and xanthone in 39.35–75.48% yield. An anticancer assay for Vero, WiDr, HeLa, and T47D cell lines was evaluated with a microculture tetrazolium assay, and an antimalarial activity test was examined using the heme polymerization inhibition method. The xanthene compound showed the lowest IC50 value (44 µg/mL) among the products in the T47D cell line. Meanwhile, the antimalarial assay showed that the xanthone compound could inhibit heme polymerization, with an IC50 value of 114 µg/mL. The molecular docking study revealed that the anticancer activity of xanthene occurred through the inhibition of the cyclooxygenase-2 (COX-2) enzyme, and the antimalarial activity of xanthone occurred through the inhibition of the Plasmodium falciparum lactate dehydrogenase enzyme. These results showed that xanthene and xanthone compounds are potential anticancer and antimalarial drugs, respectively.

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