Demethylation of Quinine Using Anhydrous Aluminium Trichloride

Quinine is a natural alkaloid having a methoxy group bound to quinoline ring and an allyl group bound to quinuclidine ring. Demethylation of quinine applying strong acid such as HBr or HI at high temperature was unsuccessful. The aim of this research was to obtain demethylated quinine by means of mild and selective demethylation procedure to prevent the addition reaction of allyl group. Selective demethylation of quinine has been carried out using anhydrous aluminium trichloride as reagent. The demethylation product was achieved in 68.12% yield by mole ratio of quinine to anhydrous aluminium trichloride of 1 to 4 in dried methylene chloride under nitrogen atmosphere. The reaction was firstly carried out at 0°C for 4 h and after the reaction mixture reached room temperature, the reaction was continued up to 24 h

Analyzing the Interaction of Andrographolide and Neoandrographolide, Diterpenoid Compounds From Andrographis Paniculata (Burm.F) Nees, to Cyclooxygenase-2 Enzyme by Docking Simulation

Cyclooxygenase (COX), an enzyme involved in the conversion of arachidonic acid to prostaglandins, exists in two isoforms, which are COX-1 and COX-2. Despite the similarities of COX-1 and COX-2, the two isoforms show subtle differences in amino acid composition at the active sites. Since COX-1 has isoleucine, a bulkier amino acid at position 523 than COX-2's valine, it allows COX-2 to have a larger space in its active site. Andrographolide reduces COX-2 expression induced by PAF and fMLP in HL60/neutrophils. Neoandrographolide inhibits COX-2 expression at the translational level. The purpose of this study is to examine the binding modes of andrographolide and neoandrographolide against COX-1 and COX-2 in terms of hydrogen bonds and docking energy, to understand their antiinflammatory property. The docking simulation indicates that both andrographolide and neoandrographolide are able to be located in the COX-2's binding pocket but not in the COX-1's. It confirms that COX-1's binding pocket is smaller than COX-2's. Based on this study, both andrographolide and neoandrographolide show selective inhibitory property to COX-2. Their selectivity are due to their specific interaction with Arg 513 in the binding pocket of COX-2, which is also shown by SC-558, a COX-2 selective inhibitor

Inhibitory Activity of Andrographolide and Andrograpanin on the Rate of PGH2 Formation

Cyclooxygenase (COX) or prostaglandin H2 synthase (PGHS) catalyzes the conversion of arachidonic acid into prostaglandins. Nonsteroidal anti-inflammatory drugs (NSAIDs) work by inhibiting both COX-1 and COX-2 isoforms, thus disturbing this reaction. In Indonesia, Andrographis paniculata (local name: sambiloto), is empirically used to reduce inflammation by consuming the herb tea of this plant. This work studied the inhibitory activity of andrographolide and andrograpanin, diterpenoids of the plant, on the rate of prostaglandin formation. Previous works have proven that andrographolide inhibited PGE2 production in LPS-induced human fibroblast cells. This study was performed by measuring the absorbance of TMPD (tetramethyl-p-phenyldiamine) oxidized by andrographolide and andrograpanin. Acetosal was used as a control drug. The rate of PGH2 formations on either COX-1 or COX- 2 was affected by andrographolide and andrograpanin. Andrographolide and andrograpanin interact longer with COX-1 than COX-2. Andrographolide shows weak inhibition on the rate of PGH2 formation, whilst andrograpanin might be further developed for potential antiinflammatory drugs. Keywords: Andrographis paniculata, anti-inflammatory, COX, cyclooxygenase, prostaglandi

SERBUK PANDAN WANGI (Pandanus amaryllifolius Roxb.) DAN PEMANFAATANNYA SEBAGAI PENAMBAH AROMA PADA MAKANAN

Telah dilakukan penelitian telaah fitokimia daun pandan (Pandanus amaryllifolius Roxb.) dan pemanfaatannya sebagai penambah aroma pada makanan. Tujuan  penelitian ini adalah untuk mengetahui pembuatan serbuk dari daun pandan wangi dengan metode Freeze Dry dan pemanfaatannya sebagai penambah aroma pada makanan. Hasil skrining fitokimia dari daun pandan wangi mengandung senyawa flavonoid, alkaloid, saponin, tanin dan polifenol. Penentuan kadar air dari daun pandan wangi didapat 11% dan kadar abu 6,375%. Dari hasil test Friedman, didapat bahwa serbuk pandan wangi yang paling banyak adalah formula C yaitu serbuk pandan wangi hasil Freeze Dry tanpa ampas

Demethylation of Quinine Using Anhydrous Aluminium Trichloride

Quinine is a natural alkaloid having a methoxy group bound to quinoline ring and an allyl group bound to quinuclidine ring. Demethylation of quinine applying strong acid such as HBr or HI at high temperature was unsuccessful. The aim of this research was to obtain demethylated quinine by means of mild and selective demethylation procedure to prevent the addition reaction of allyl group. Selective demethylation of quinine has been carried out using anhydrous aluminium trichloride as reagent. The demethylation product was achieved in 68.12% yield by mole ratio of quinine to anhydrous aluminium trichloride of 1 to 4 in dried methylene chloride under nitrogen atmosphere. The reaction was firstly carried out at 0°C for 4 h and after the reaction mixture reached room temperature, the reaction was continued up to 24 h

Zingiber officinale var. Rubrum Reduces the Rate of Prostaglandin Production

In Indonesia, red ginger (Zingiber officinale var. Rubrum) is usually used as topical pain reducer by directly applying the fresh rhizome. The aim of this research was to provide information regarding the pharmacological activity of Z. officinale var. Rubrum rhizome infusion on the rate of prostaglandin production. The Z. officinale var. Rubrum rhizome used in this research was purchased from Research Institute for Spices and Medicinal Plants (Balittro) Manoko Lembang, West Java, Indonesia. This research was conducted by applying TMPD (N,N,N’,N’-tetramethyl-p-phenylendiamine) as the reagent. COX-1 and COX-2 enzyme inhibitory activity can be seen from TMPD chromogenic changes that occur during PGG2 reduction to PGH2. Phytochemical screening showed that flavonoid, quinone, and monoterpenoid/sesquiterpenoid were detected in both dried rhizomes and the water extract. Three spots were detected on thin-layer chromatography system which employing chloroform-methanol (5:5) as the eluent. The rate of prostaglandin formations either by Z. officinale var. Rubrum rhizome infusion or acetylsalicylic acid on COX-1 is slower (at 25th minutes) rather than COX-2 (5th minutes). We concluded that the rhizome of Z. officinale var. Rubrum reduces the rate of prostaglandin production. The rhizome of red ginger reduces the rate of prostaglandin production, which is slower in COX-1 than in COX-2. This plant could be further developed as anti-inflammatory drug candidate. Keywords: acetosal, antiinflammation, cyclooxygenase, NSAIDs, red ginge