scholarly journals ANTIOXIDANT ACTIVITY OF 2,6,4’-TRIHYDROXY-4-METHOXY BENZOPHENONE FROM ETHYL ACETATE EXTRACT OF LEAVES OF MAHKOTA DEWA (Phaleria macrocarpa (Scheff.) Boerl.)

2011 ◽  
Vol 11 (2) ◽  
pp. 180-185 ◽  
Author(s):  
Susilawati Susilawati ◽  
Sabirin Matsjeh ◽  
Harno Dwi Pranowo ◽  
Chairil Anwar

Mahkota dewa plant (Phaleria macrocarpa (Scheff.) Boerl.) which is included into family of Thymelaeaceae is one of Indonesia's traditional medicines. Chemical constituent has been isolated from ethyl acetate extract of leaves of mahkota dewa. Sample was extracted with methanol, concentrated then extracted by n-hexane, chloroform and ethyl acetate. The ethyl acetate extract was separated and fractionated by column chromatography. The first fraction was purified by TLC preparative and recrystalization. Compound was isolated as red-brown spherical crystal in 8 mg (m.p. 129-131 °C). Its spot gave dark fluoroscence at TLC plate (UV366) with Rf of 0.3 at TLC chromatogram with eluent of n-hexane : ethyl acetate (7:3); 0.6 with n-hexane : ethyl acetate (1:1); 0.9 with -hexane : ethyl acetate (4:6). This compound was dissolved in methanol. Compound was identified by UV, IR, 1H NMR, 13C NMR and NMR 2 dimension (HMQC, COSY, HMBC and DEPT-135) spectroscopic as 2,6,4'-trihydroxy-4-methoxybenzophenon. This compound as well as the ethyl acetate extract showed antioxidant activity on DPPH with IC50 was 10.57 and 101.06 μg/mL, respectively. This compound showed strong antioxidant activity on DPPH, almost to the standard antioxidant activity of quercetin (IC50 of 2.93 μg/mL)

2012 ◽  
Vol 12 (1) ◽  
pp. 62-69 ◽  
Author(s):  
Susilawati Susilawati ◽  
Sabirin Matsjeh ◽  
Harno Dwi Pranowo ◽  
Chairil Anwar

Mahkota dewa (Phaleria macrocarpa (Scheff.) Boerl.) which is belong to family of Thymelaeaceae is one of Indonesian traditional medicines. Chemical constituent has been isolated from bark of mahkota dewa. Sample was extracted with methanol. Concentrated methanol extract was extracted by n-hexane, chloroform and ethyl acetate. A Compound that separated and purified by column chromatography from ethyl acetate extract is a red spherical crystal (m.p. 94-95 °C). Its spot gave yellow fluorescence at TLC plate (UV366) and has optical rotation of -9.3°(c. 2 mg/mL, methanol). Structure elucidation by UV, IR, 1H-NMR, 13C-NMR and NMR 2 dimension (HMQC, COSY, HMBC and DEPT-135) spectroscopy show that the compound gives a name macronone. Computational chemistry calculation using Hyperchem on the level of semiempirical method PM3 was confirmed the conformation of macronone. DPPH method shows that macronone has lower antioxidant activity compare to the ethyl acetate extract.


2017 ◽  
Vol 18 (02) ◽  
pp. 137-145
Author(s):  
Melindra Mulia

Coumarin has been isolated and characteritated from rind of  Citrus nobilis Lour by maseration methode with methanol. After fractionation by n-hexane and ethyl acetate, collected the phase ethyl acetate which positive of coumarin. From ethyl acetate extract coumarin have been isolated by column chromatography. The isolation results was obtain 2,159 g of pure white needle-shape crystalline with the melting point of 126,2-127,60C. Structure of the isolated coumarine was elucidated by spectroscopic methodes, UV-Vis,13C-NMR, 1H-NMR, 2D-NMR (DEPT/HSQC, COSY, NOESY, HMBC) and IR spectra. Based on the spectra data the isolated coumarine is marmin.


1970 ◽  
Vol 7 (1) ◽  
pp. 71-74 ◽  
Author(s):  
Md Enamul Haque ◽  
Md Nahidul Islam ◽  
Dipankar Das Gupta ◽  
Mahbub Hossain ◽  
Hossain Uddin Shekhar ◽  
...  

Two triterpenoids, phragmalin triacetate (1) and lupeol (2) were isolated from an ethyl acetate extract of the stem bark of Crataeva nurvala (Capparidaceae) by repeated chromatography over silica gel. The structures of these compounds were determined by spectroscopic analyses (UV, IR, 1H NMR, 13C NMR and EIMS). This is the first report of the systematic phytochemical investigation and the presence of these compounds 1 and 2 from this plant. Key words: Crataeva, Capparidaceae, Phragmalin triacetate and Lupeol.  DOI = 10.3329/dujps.v7i1.1221 Dhaka Univ. J. Pharm. Sci. 7(1): 71-74, 2008 (June)


2014 ◽  
Vol 16 (2) ◽  
pp. 82-86 ◽  
Author(s):  
Chandra Risdian ◽  
Tjandrawati Mozef ◽  
Puspa D.N Lotulung

Daun sukun (Artocarpus altilis) sudah lama dijadikan sebagai obat tradisional untuk mengatasi berbagai penyakit seperti liver cirrhosis, hipertensi, dan diabetes. Ekstrak etil asetat dari daun sukun juga berpotensi menghambat pertumbuhan sel kanker. Beberapa senyawa yang telah diketahui sebagai agen antikanker di dalam ekstrak etil asetat daun sukun adalah golongan geranil flavonoid. Akan tetapi, senyawa pyranoflavoid belum dilaporkan dapat ditemukan pada daun sukun. Untuk itu, penelitian ini bertujuan untuk mengisolasi senyawa pyranoflavonoid dari ekstrak etil asetat daun sukun dan menguji aktivitasnya sebagai antikanker. Daun sukun diekstraksi dengan etanol 70% kemudian dilakukan partisi dengan petroleum eter dan etil asetat. Ekstrak etil asetat yang diperoleh difraksinasi dengan kromatografi kolom silica gel dengan gradient elusi heksan-etil asetat sehingga diperoleh senyawa kristal berwarna kuning, AA3. Senyawa AA3 kemudian diidentifikasi dengan spektrofotometer UV-Vis, LC-MS, 1H-NMR dan 13C-NMR dan diperoleh hasil bahwa senyawa AA3 tersebut adalah siklokomunol yang merupakan golongan pyranoflavonoid. Uji antikanker siklokomunol dengan MCF-7 dan T47D menunjukkan adanya aktivitas antikanker dengan nilai IC50 masing-masing adalah 75.46 µM dan 36.20 µM selama 48 jam.Kata kunci:Artocarpus altilis, siklokomunol, antikanker, MCF-7, T47D. Leaves of breadfruit Artocarpus altilis (Parkinson) Fosberg has long been used as traditional medicine to overcome a variety of diseases such as liver cirrhosis, hypertension, and diabetes. Ethyl acetate extract of the leaves of breadfruit also potentially inhibit the growth of cancer cells. Several compounds have been known as an anticancer agent in the ethyl acetate extract of leaves of breadfruit is belong to geranyl flavonoid group. However, the compound belong to pyranoflavoid group has not been reported can be found on the leaves of breadfruit. Therefore, this study aims to isolate the pyranoflavonoid compound from ethyl acetate extract of leaves of breadfruit and tested as an anticancer agent. Breadfruit leaves were extracted with 70% ethanol and then made a partition with petroleum ether and ethyl acetate. Ethyl acetate extract obtained was fractionated by silica gel column chromatography with gradient elution of hexane-ethyl acetate to obtain a yellow crystalline compound, AA3. AA3 compound was identified by UV-Vis spectrophotometer, LC-MS, 1H-NMR and 13C-NMR and obtained results that AA3 compound is siklokomunol which is belong to pyranoflavonoid group. Anticancer test of siklokomunol with MCF-7 and T47D showed anticancer activity with IC50 values of each are 75.46 µM and 36.20 µM, respectively, for 48 hours.Keywords: Artocarpus altilis, siklokomunol, anticancer, MCF-7, T47D.


2017 ◽  
Vol 19 (1) ◽  
pp. 11-17
Author(s):  
Dede Sukandar ◽  
Siti Nurbayti ◽  
Tarso Rudiana ◽  
Tsalats Wahyul Husna

Active compounds with antioxidant activity were isolated from ethyl acetate extract of namnam stem (C. cauliflora L.) that had undergone maceration and fractionation by gravity column chromatography. The compounds were later identified by by using UV-Vis Spectrophotometry, FTIR, LCMS and 1H-NMR. Ethyl acetate extract of namnam stem showed considerably high antioxidant activity (IC50 value 4.68 ± 0.035 ppm). The results of analysis by UV-Vis and FTIR showed carbonyl group conjugated with an aromatic ring at band I (λmax 330.22 nm), chromophore group of alkene (C=C) at band II (λmax 268.67 nm) and functional groups such as O−H (3343.91 cm-1), C=O (1729.23 cm-1), C=C (1652.64 and 1611.99 cm-1), C−O (1269.89) and C−H ortho (738.23 cm-1). LCMS (m/z 270.9246) and 1H-NMR data showed seven proton signals on the aromatic ring at carbon position C-3 at δH 6.86 ppm (1H, s), C-6 at δH 5.95 ppm (1H, d, J=1.95 Hz), C-8 at δH 6.25 ppm (1H, d, J= 1.95 Hz), C-2’ and C-6’ at δH 7.03 ppm (2H, d, J=7.87 Hz), C-3’ and C-5’ at δH 6.87 ppm (2H, d, J= 7.87 Hz) so that the structure was identified as a flavonoid which was 4 ', 5,7-trihydroxy-flavones or known as apigenin. The isolated apigenin had very strong antioxidant activity, as shown by IC50 value of 5.18 ± 0.014 ppm.


2019 ◽  
Vol 54 (3) ◽  
pp. 275-282 ◽  
Author(s):  
MM Haque ◽  
N Sultana ◽  
SMT Abedin ◽  
SE Kabir

A phytochemical investigation was conducted on the flowers of Nyctanthesarbor-tristis Linn. For isolation of compounds, the dried flower’s powder was successively extracted with n-hexane, dichloromethane, ethyl acetate and methanol. The extracts were fractionated using different chromatographic techniques and four compounds were isolated. Stigmasterol (1) from n-hexane, rengyolone (2) from dichloromethane and two other compounds namely, 2-phenylethyl β-D-glucopyranoside (3) and n-tetradecyl-β-D-glucopyranoside (4) from ethyl acetate extract, were isolated. These compounds (1-4) were characterized on the basis of IR, 1H NMR, 13C NMR, DEPT-135 NMR. Compounds 1 and 3 were isolated for the first time from this plant while compound 4 has been isolated and completely characterized from this plant as well as from the natural sources. Bangladesh J. Sci. Ind. Res.54(3), 275-282, 2019


2015 ◽  
Vol 9 (1) ◽  
pp. 1 ◽  
Author(s):  
Adlis Santoni ◽  
Sabariah ◽  
Mai Efdi

A brine shrimp toxic compound has been isolated from Mangifera foetida L. steam bark. Based on spectroscopic data (IR,1H- NMR, 13C-NMR 1D and 2D), the structure of this compound was identified as mangiferenes B, C30H47O2. In this study, the n-hexane, ethyl acetate, methanol extracts and isolated compound showed toxic effects (LC50 471.9543; 534.5209, 678.4421, and 22.1615 μg/mL, respectively). The toxicity degree among the three extracts and isolated compound is isolated compound > n-hexane extract > ethyl acetate extract > methanol extract.


2019 ◽  
Vol 57 (3) ◽  
pp. 294
Author(s):  
Ho Dac Hung ◽  
Doan Huy Tien ◽  
Nguyen Thi Ngoan ◽  
Ba Thi Duong ◽  
Do Quoc Viet ◽  
...  

The first study on chemical constituents and biological activities of fruits of Dipterocarpus retusus Blume (Dipterocarpaceae.) growing in Vietnam was reported. Column chromatography of the ethyl acetate extract led to the isolation of five compounds: eleutherol (1), 3, 5, 4' - trihydroxy - trans - stilbene (2), polydatin (3) and β-sitosterol (4), β-sitosterol-3-O-β-D-glucopyranoside (5). Their structures were elucidated based on the NMR spectroscopic methods and comparison with literature date. The extracts from fruits of D. retusus Blume by n-hexane, ethyl acetate and butanol, consecutively, were evaluated for antioxidative and cytotoxic activities.


2015 ◽  
Vol 15 (2) ◽  
pp. 179-186
Author(s):  
Susilawati Susilawati ◽  
Sabirin Matsjeh ◽  
Harno Dwi Pranowo ◽  
Chairil Anwar

Mahkota dewa plant (Phaleria macrocarpa (Scheff.) Boerl.) which is belong to family of Thymelaeaceae is one of Indonesia's traditional medicines. The aim of this research is to isolate secondary metabolites from ethyl acetate extract of leave and fruit of mahkota dewa and to determine the molecular structure of isolated compounds using spectroscopic method and to know the antibacterial activity of the isolated compound. Sample was extracted with methanol, concentrated then extracted by n-hexane, chloroform and ethyl acetate. The compounds were separated and purified with column chromatography. The compound 1 was isolated from ethyl acetate extract of leave as white needle amorphous solid as 45 mg. The compound was identified by spectroscopic as 4,6-dihydroxy-4’-methoxybenzophenon-2-O-β-D-glucopyranoside and named isophalerin B. From the test results of antibacterial activity showed that the compound 1 (10 mg/mL) in ethanol has a weak activity against the bacteria S. aureus and E. coli. The compound 2 was isolated from ethyl acetate extract of fruit as peach needle crystal as 10 mg. The compound was identified by spectroscopic as 4,6-dihydroxy-4’-methoxybenzophenon-2-O-α-D-glucopyranoside and named isophalerin A.


2019 ◽  
Vol 22 (5) ◽  
pp. 179-183 ◽  
Author(s):  
Sri Purwanti ◽  
Wulan Tri Wahyuni ◽  
Irmanida Batubara

Jernang resin is secretion of jernang rattan (Daemonorops draco, Arecaceae family) fruits which is endemic in Southeast Asia. This resin has various biological activities and empirically used as wound healing, headache medicines, and fever remedies by Anak Dalam ethnic group from Jambi. This study was performed to evaluate the antioxidant activity of nonpolar fraction of D. draco resin which collected from Jambi Province, Sumatera, Indonesia. Resin was extracted with n-hexane, ethyl acetate, and methanol respectively. The antioxidant properties of the extracts were then evaluated using 1,1-diphenyl-2picryl-hidrazyl radical scavenging assay. The most active extract was further fractionated using n-hexane and methanol and separated using column chromatography and preparative thin layer chromatography. Separation of the extract was conducted through antioxidant assay-guided fractionation. Characterization of the active fraction was carried out by infrared spectroscopy. The result shows that ethyl acetate extract provides higher antioxidant activity (IC50 = 27.61 µg/mL) compare to methanol and n-hexane extracts. N-hexane fraction of ethyl acetate extract used for further separation using column and preparative thin layer chromatography due to its antioxidant activity. Separation using column chromatography resulting in 9 fractions (F.1-9). Fraction F.5 provide high antioxidant activity (IC50 = 17.27 µg/mL) and further separated using preparative thin layer chromatography resulting two fractions with lower antioxidant activity F.5.1 (IC50 = 85.18 µg/mL) and F.5.2 (IC50 = 34.94 µg/mL). Characterization of fraction F.5.2 using infrared spectroscopy showed that component in fraction F.5.2 contains NH-substituted benzene.


Sign in / Sign up

Export Citation Format

Share Document