Isolasi dan Identifikasi Senyawa Terpena Hasil Pirolisis Getah Karet Alam (Hevea Brasiliensis)

Isolation and identification of terpenes obtained from the pyrolisis of natural rubber (Hevea brasiliensis) latex have been conducted. The latex was pyrolized under reduced pressure without any solvent. The pyrolysis products contains water, protein and rubber oil. The rubber oil was separated and identified using GC-MS.The results showed that the rubber oil contained 22 compounds. According to literature review, 12 compounds were identified as terpene, including monoterpene, sesquiterpene and diterpene. Monoterpene compounds were isolimonene, l-limonene, P-felandrene, d-limonene and camphene. The identified sesquitterpenes were 2,4a,8,8-tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropane [d] naphthalene, P-farnasene, a-amorphene, y-amorphene and bisabolene. The analyzed diterpenes were abietadiene and kaurene. The dominant terpene was d-limonene. The d-limonene was isolated using fractional distillation and had the purity of 96.79%

Isolasi dan Identifikasi Senyawa Terpena Hasil Pirolisis Getah Karet Alam (Hevea brasiliensis)

Isolation and identification of terpenes obtained from the pyrolisis of natural rubber (Hevea brasiliensis) latex have been conducted. The latex was pyrolized under reduced pressure without any solvent. The pyrolysis products contains water, protein and rubber oil. The rubber oil was separated and identified using GC-MS.The results showed that the rubber oil contained 22 compounds. According to literature review, 12 compounds were identified as terpene, including monoterpene, sesquiterpene and diterpene. Monoterpene compounds were isolimonene, l-limonene, P-felandrene, d-limonene and camphene. The identified sesquitterpenes were 2,4a,8,8-tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropane [d] naphthalene, P-farnasene, a-amorphene, y-amorphene and bisabolene. The analyzed diterpenes were abietadiene and kaurene. The dominant terpene was d-limonene. The d-limonene was isolated using fractional distillation and had the purity of 96.79%

SINTESIS DAN UJI AKTIVITAS SENYAWA (1)-N-(n-BUTIL)- DAN (1)-N-(t-BUTIL)-1,10-FENANTROLINIUM SEBAGAI SENYAWA POTENSIAL ANTIMALARIA BARU

The synthesis of (1)-N-(n- buthyl)- dan (1)-N-(t-buthyl)-1,10-phenanthrolinium with 1,10-phenanthroline monohydrate as starting material through two steps has been carried out. The first step of reaction is chlorination and bromination of n-buthyl-alcohol/t-buthyl alcohol using HCl and HBr, respectively. The result of reaction is nbuthyl bromide 2 (colourless liquid, 70.92%) and t-buthyl chloride 4 (colourless liquid, 92.36%), respectively. The second step of reaction is alkylation of 1,10-phenanthroline 5 using n-buthyl bromide and t-buthyl chloride reagents that its was refluxed for 21 and 23 h, respectively. The results of reaction are (1)-N-(n- buthyl)-1,10fenantrolinium bromida 6 and (1)-n-(t-buthyl)-1,10-fenantrolinium chloride 7 in yield from 84.70% and 78.16%, respectively. The results of testing in in vitro antiplasmodial activity at chloroquine-resistant P. falciparum FCR3 strain to (1)-N-(n-buthyl)- and (1)-N-(t-buthyl)-1,10- phenanthrolinium obtained that (1)-N-(n-buthyl)-1,10phenanthrolinium bromide 6 has higher antimalarial activity (IC50 : 0.03±0.01 µM) than antimalarial activity of (1)-n-(t-buthyl)-1,10-phenanthrolinium chloride 7 (IC50 : 2.09±0.08 µM). While, the results of testing in in vitro antiplasmodial activity at chloroquine-resistant P. falciparum D10 strain to (1)-N-(n-buthyl)- and (1)-N-(t-buthyl)1,10-f phenanthrolinium obtained that (1)-N-(n-butil)-1,10- phenanthrolinium bromide 6 has higher antimalarial activity (IC50 : 1.40±0.82 µM) than antimalarial activity of (1)-n-(t-buthyl)-1,10- phenanthrolinium chloride 7 (IC50 : 2.24±0.05 µ

QUANTITAVE STRUCTURE-ACTIVITY RELATIONSHIP ANALYSIS (QSAR) OF ANTIMALARIAL 1,10-PHENANTHROLINE DERIVATIVES COMPOUNDS

Quantitative Electronic Structure-Activity Relationship (QSAR) analysis of a series of 1,10-phenanthroline derivatives as antiplasmodial compounds have been conducted using atomic net charges (q), dipole moment (μ) ELUMO, EHOMO, polarizability (α) and log P as the descriptors. The descriptors were obtained from computational chemistry method using semi-empirical PM3. Antiplasmodial activities were taken as the activity of the drugs  against  chloroquine-resistant Plasmodium falciparum FCR3 strain and are presented as the value of ln (1/IC50) where IC50 is an effective concentration inhibiting 50% of the parasite growth. The best model of QSAR model was determine by multiple linear regression method and giving equation of QSAR: ln 1/IC50  =  3.732 + (5.098) qC5 + (7.051) qC7 + (36.696) qC9 + (41.467) qC11 -(135.497) qC12 + (0.332) μ -                    (0.170) α + (0.757) log P. The equation was significant on the 95% level with statistical parameters: n=16; r=0.987; r2= 0.975; SE=0.317;  Fcalc/Ftable = 15.337 and gave the PRESS=0.707. Its means that there were only a relatively few deviations between the experimental and theoretical data of antimalarial activity.   Keywords: QSAR, antimalarial, semi-empirical method, 1,10-phenanthroline

SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-ALKYL- AND (1)-N-BENZYL-6-NITRO-1,10-PHENANTHROLINIUM SALTS AS NEW POTENTIAL ANTIMALARIAL AGENTS

The synthesis of 5-nitro-1,10-phenanthroline hydrate 2 derivatives from 1,10-phenanthroline monohydrate as starting material has been carried out. The 5-nitro-1,10-phenanthroline hydrate 2 was obtained through nitration reaction using H2SO4 and HNO3 as catalyst and reagent, respectively. Synthesis of (1)-N-alkyl-6-nitro- and (1)-N-benzyl-6-nitro-1,10-phenanthrolinium have been prepared using dimethyl sulphate (DMS), diethyl sulphate (DES), benzyl chloride, benzyl bromine, and benzyl iodide. The reagents of benzyl bromine, and benzyl iodide were synthesized from benzyl chloride using NaBr in ethanol absolute and NaI in acetone, respectively. The five compounds of 5-nitro-1,10-phenanthroline hydrate 2 derivatives were conducted to evaluate the in vitro antiplasmodial activity. The in vitro antiplasmodial was evaluated on strains of Plasmodium falciparum FCR-3 resistant chloroquine and D10 sensitive chloroquine. The 50% inhibition concentration (IC50) of the five compounds ranged from 2.41±1.41 to 0.07±0.01 μM. The results showed that the (1)-N-benzyl-6-nitro-1,10-phenanthrolinium iodide had highest antiplasmodial activity

SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE

Synthesis of (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide from 1,10-phenanthroline monohydrate and 4-methoxybenzaldehyde as starting material and evaluation of its antiplasmodial activities have been carried out. The 4-methoxybenzyl alcohol was prepared from 4-methoxy-benzaldehyde using sodium borohydride (NaBH4) reagent and ethanol absolute solution. The mixture was refluxed for 3 h. To yield colorless dilution compound with 90.41 % in efficiency. Furthermore, bromination of 4-methoxybenzyl alcohol with phosphorus bromide (PBr3) was conducted by refluxing for 3 h. The product of this reaction was yellow liquid of 4-methoxybenzyl bromide, 79.03% yield and 95.34 % purity. The final step of reaction was benzylation of 1,10-phenanthroline monohydrate with 4-methoxybenzyl bromide reagent. It was conducted by refluxing in aceton for 8 h at 55 oC. The yield of the reaction was (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide (77.63%). It is pink solid form, and its melting point is 192-193 oC. Identification of the product was carried out by means of GC-MS, IR and 1H-NMR spectrometers. The in vitro antiplasmodial activity on chloroquine-resistant Plasmodium falciparum FCR-3 strain and chloroquine sensitive P. falciparum D10 strain for (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide were determined by microscopic method. The result showed that after 72 h incubation, it has IC50 0.93±0.02 µM and 1.21±0.09 µM, respectively.   Keywords: 1,10-phenanthroline,  (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide, 4 methoxybenzaldehyde, antiplasmodial activitie

SINTESIS DAN UJI AKTIVITAS ANTIMALARIA SENYAWA (1)-N-BENZIL-1,10- FENANTROLINIUM BROMIDA

A synthetic methods was employed to prepare (1)-N-benzyl)-1,10-phenanthroliniumbromide 4 from 1,10phenanthroline 3 and benzylchloride 1 through substitution and alkylation reactions. The compound (1)-Nbenzyl)-1,10-phenanthroliniumbromide 4 was tested through antiplasmodial test. The benzylbromide 2 was synthesized through substitution reaction of benzylchloride 1 and NaBr which has a yield of 74.25%. The (1)-N-benzyl)-1,10-phenanthroliniumbromide 4 was synthesized from 1,10-phenanthroline 3 using benzylbromide 2 reagents which refluxed for 8 hours with 84.04% yields. The results of testing in in vitro antiplasmodial activity at chloroquine-resistant Plasmodium falciparum FCR3 strain to (1)-N-benzyl)-1,10-  phenanthroliniumbromide 4 has high antimalarial activity (IC50 : 0.10±0.04 µM

PHOSPHOLIPIDS FROM PUMPKIN (<i>Cucurbita moschata</i> (Duch.) Poir) SEED KERNEL OIL AND THEIR FATTY ACID COMPOSITION

The phospholipids (PL) of pumpkin (Cucurbita moschata (Duch) Poir) seed kernel and their fatty acid composition were investigated. The crude oil was obtained by maceration with isopropanol followed by steps of extraction yielded polar lipids. The quantitative determination of PLs content of the dried pumpkin seed kernel and their polar lipids were calculated based on the elemental phosphorus (P) contents which was determined by means of spectrophotometric methods. PL classes were separated from polar lipids via column chromatography. The fatty acid composition of individual PL was identified by gas chromatography-mass spectrometry (GC-MS). The total of PL in the pumpkin seed kernels was 1.27% which consisted of phosphatidylcholine (PC), phosphatidylserine (PS) and phosphatidyletanolamine (PE). The predominant fatty acids of PL were oleic and palmitic acid in PC and PE while PS's fatty acid were dominantly consisted of oleic acid and linoleic acid

SYNTHESIS AND ANTIPLASMODIAL ACTIVITY TESTING OF (1)-N-(4-METHOXYBENZYL)-1,10-PHENANTHROLINIUM BROMIDE COMPOUND

Synthesis of (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide from 1,10-phenanthroline monohydrate and 4-methoxybenzaldehyde as starting material and evaluation of its antiplasmodial activities have been carried out. The 4-methoxybenzyl alcohol compound was prepared from 4-methoxy-benzaldehyde using sodium borohydride (NaBH4) reagent and ethanol absolute solution. The mixture was refluxed for 3 h. Then it yielded colorless dilution compound with 90.41% in efficiency. Furthermore, bromination of 4-methoxybenzyl alcohol with phosphorus bromide (PBr3) was conducted by refluxing for 3 h. The product of this reaction was yellow liquid of 4-methoxybenzyl bromide, 79.03% yield and 95.34% purity. The final step of reaction was benzylation of 1,10-phenanthroline monohydrate with 4-methoxybenzyl bromide reagent. It was conducted by refluxing in aceton for 8 h at 55oC. The yield of the reaction was (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide (77.63%). It is pink solid form, and its melting point is 192-193oC. Identification of the product was carried out by means of GC-MS, IR and 1H-NMR spectrometers. The in vitro antiplasmodial activity on chloroquine-resistant Plasmodium falciparum FCR-3 strain and chloroquine sensitive P. falciparum D10 strain for (1)-N-(4-methoxybenzyl)-1,10-phenanthroline bromide were determined by microscopic method. The result showed that after 72 h incubation, it has IC50 0.93&plusm