Chairil Anwar

New eremophilane and dichlororesorcinol derivatives produced by endophytes isolated from Ficus ampelas

The novel compound, 11-O-methylpetasitol (1), was isolated from Penicillium sp. N-175-1, and two new compounds, cosmochlorins D (5) and E (6), were isolated from Phomopsis sp. N-125. In addition, three known eremophilane sesquiterpenes, sporogen-AO1 (2), petasol (3) and 6-dehydropetasol (4), were isolated from Penicillium sp. N-175-1. The structures of 1, 5 and 6 were elucidated by a combination of extensive spectroscopic analyses, including 2D NMR, high-resolution electrospray ionization time-of-flight mass spectrometry (HRESITOFMS) and chemical reactions. Compounds 2, 3, 5 and 6 exhibited cytotoxicity to HL60 and 2 and 3 to HeLa cells. Furthermore, 2 and 3 showed robust growth-restoring activity of a Saccharomyces cerevisiae (cdc2-1 rad9Δ) mutant strain, whereas 5 and 6 exhibited minor growth-restoring activity in this strain. Thus, these compounds may inhibit the growth of HL60 and HeLa cells by blocking the cell cycle, and they may be utilized as new lead compounds that act as inhibitors of survival signal transduction pathways.

Synthesis of 7-hydroxy-4’-methoxyflavanone and 7-hydroxy-4’-methoxyflavone as a candidate anticancer against cervical (HeLa) cancer cell and colon (WiDr) cancer cell by in vitro

The compound 7-hydroxy-4’-methoxyflavanone and 7-hydroxy-4’-methoxyflavone have been synthesized through cyclization reaction of 2 ’, 4’-dihydroxy-4-methoxychalcone (1,3-diphenyl-2-propene-1-one). The 2 ’, 4’-dihydroxy-4-methoxychalcone were synthesized through Claisen-Schmidt condensation from 2,4-dihydroxyacetophenone and 4-methoxybenzaldehyde (anisaldehyde) in aqueous KOH as a catalyst in ethanol. The 7-hydroxy-4’-methoxyflavanone has been synthesized through cyclization reaction of 2 ’, 4’-dihydroxy-4-methoxychalcone by Oxa-Michael addition reaction with sulfuric acid as a catalyst in ethanol. The 7-hydroxy-4’-methoxyflavone has been synthesized through oxidative cyclization reaction of 2 ’, 4’-dihydroxy-4-methoxychalcone using I2 in DMSO as a catalyst with a mole ratio (1: 1) mol. All these producets were characterized by FT-IR, GC-MS, and 1H-NMR and 13C-NMR spectrometer. Both of these compounds were tested citotoxycity activity as an anticancer against cervical and colon cancer cells (HeLa and WiDr ...

Synthesis of 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone as a candidate anticancer against cervical (WiDr), colon (HeLa), and breast (T47d) cancer cell lines in vitro

The compound 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone have been synthesized through Claisen-Schmidt reaction from 2-hydroxyacetophenone and 2,4-dihydroxyacetophenone with 4-hydroxy-3-methoxy benzaldehida (vanillin) in aqueous KOH 40% and KSF montmorillonite as catalyst in methanol. All these products were characterized by FT-IR, TLC Scanner, GC-MS, MS-Direct, and 1H-NMR and 13C-NMR spectrometer. Both of these compounds were tested citotoxycity activity as an anticancer against cervical, colon, and breast cancer cells (Hela, WiDr, and T47D cell lines) using MTT assay in vitro. Dose series given test solution concentration on Hela, WiDr, and T47D cells started from 6,25; 25; 50 and 100 µg/mL with incubation treatment for 24 hours. The result of study showed that the 2’,4-dihydroxy-3-methoxychalcone as bright yellow crystal with the melting point of 114-115 °C and the yield of 13.77% and the 2’,4’,4-trihydroxy-3-methoxychalcone as bright yellow crystals with the melting point of 195-197 °C and the yield of 6%. Other 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone also exhibited cytotoxic activity against the cancer cell lines, with the 2’,4’,4-trihydroxy-3-methoxychalcone showed greater activities than the 2’,4-dihydroxy-3-methoxychalcone in WiDr cell lines. The 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone exhibited strong anticancer activities with IC50 value below 20 µg/mL. The activity of 2’,4’,4-trihydroxy-3-methoxychalcone showed the most active against Hela and WiDr cell lines with IC50 value 8.53 and 2.66 µg/mL respectively, than T47D cell lines with IC50 value 24.61 µg/mL. The test results cytotoxic of 2’,4-dihydroxy-3-methoxychalcone showed the most active against Hela and WiDr cell lines with IC50 value 12.80, 19.57 µg/mL than T47D cell lines with IC50 value of 20.73 µg/mL. IC50 value indicated that 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone potential as inhibitors in Hela, WiDr and T47D cell lines.The compound 2’,4-dihydroxy-3-methoxychalcone and 2’,4’,4-trihydroxy-3-methoxychalcone have been synthesized through Claisen-Schmidt reaction from 2-hydroxyacetophenone and 2,4-dihydroxyacetophenone with 4-hydroxy-3-methoxy benzaldehida (vanillin) in aqueous KOH 40% and KSF montmorillonite as catalyst in methanol. All these products were characterized by FT-IR, TLC Scanner, GC-MS, MS-Direct, and 1H-NMR and 13C-NMR spectrometer. Both of these compounds were tested citotoxycity activity as an anticancer against cervical, colon, and breast cancer cells (Hela, WiDr, and T47D cell lines) using MTT assay in vitro. Dose series given test solution concentration on Hela, WiDr, and T47D cells started from 6,25; 25; 50 and 100 µg/mL with incubation treatment for 24 hours. The result of study showed that the 2’,4-dihydroxy-3-methoxychalcone as bright yellow crystal with the melting point of 114-115 °C and the yield of 13.77% and the 2’,4’,4-trihydroxy-3-methoxychalcone as bright yellow crystals with the melting point...

Synthesis of Curcumin Analogues Monoketone from Cinnamaldehyde and their Inhibition Assay against Alpha-Glucosidase Enzyme

The synthesis of curcumin analogues monoketone as target compounds from cinnamaldehyde and inhibition assay against alpha-glucosidase enzyme had been performed. The stepwise of synthesis was performed by aldol condensation Claisen-Schmidt reaction andused ketones variation to give curcumin analogues monoketone. The antidiabetic activity of curcumin analogues was carried out by inhibition test against alpha-glucosidase enzyme isolated from rotten rice (Oryza sativa). The first step of synthesis was started by reacting cinnamaldehyde and monoketones such as acetone (curcumin analog A [(1E,3E,6E,8E)-1,9-diphenyl-1,3,6,8-nanotetraen-5-one]), cyclopentanone (curcumin analog B [(2E,5E)-2,5-bis ((E)-3-phenylallylidene) cyclopentanone], and cyclohexanone (curcumin analog C [(2E,6E)-2,6-bis [(E)-3-phenylallylidene] cyclohexanone]) in ethanol as solvent. The synthesis was carried out in base condition (KOH) by stirring at 52 °C for 50 minutes. The structures of all products were identified by using FTIR, direct inlet-MS, 1H-and 13C-NMR. Futhermore, the activity of curcumin analogues was tested against with alpha-glucosidase enzyme inhibition. The results show that the curcumin analogues (A-C) were yielded in 85.57; 72.15; and 82.97%, respectively as yellow solid. The melting point of curcuminanalogues (A-C) were at 116.60-122.40; 196.20-200.10; and 142.30-148.10 °C, respectively. The inhibition of alpha-glucosidase enzyme indicated that the curcumin analog B was potential to inhibit alpha-glucosidase enzyme with the highest activity by giving inhibition percentage of about 70.71% at 2.5 mM.

Complete Chemo Type of Three Species of Basils (Ocimum basilicum) Grown in Indonesia

Abstract The three species of basil (Ocimum basilicum) i.e. lemon basil (O. citriodorum), purple basil (O. canum) and green basil (O. violaceum) had been analyzed to derived their complete chemo type. Ten series of time difference in wilting of aerial part of basil were plotted in different harvesting period. Each accession of Ocimum species underwent air dried preparations varying from 0 day (fresh) to 4 months (very dry), respectively. Steam distillation was subjected in each process to collect an essential oil state. The analysis of chemical components was conducted using Gas chromatography/Mass spectrometry (GC-MS). Results was obtained by analysis of similar compounds that found during series of wilting time. The frequence (in percentage) of their appearance used as a basis of complete chemo type determination. The complete chemo type of lemon basil, purple basil, and green basil suggested to be listed as major compound followed by minor constituents set in descending order of concentrations. The complete chemo type of lemon basil could be written as : trans-citral > cis-citral>cis-α-bisabolene>(-)-caryophyllene oxide>trans-caryophyllene>α-bergamotene >(E)-β-farnesene > germacrene D>β-bisabolene>β-sesqui phellandrene; also for purple basil : methyl eugenol>1,8-cineole>germacrene-D>β-elemene>δ-guaiene>camphor>germacrene-B>l-linalool>α-guaiene>α-humulene>α- copaene>bornyl acetate; and for green basil : methyl chavicol>methyl eugenol>1,8-cineole>α-amorphene > β-elemene>trans-caryophyllene>α-bergamotene. This result could be used as accomplished of chemo taxonomy or solving a taxonomical problem in basils.