Extraction Of The Crown Glycosides A And Its Derivatives

Mahkota Dewa (Phaleria macrocarpa [Scheff.] Boerl) was widely distributed in Indonesia, empirically, the stems,leaves and fruits of which were used to control many diseases such as cancer,impotency,hemorrhoid,diabetes mellitus,allergies,liver and heart diseases,kidney disorders,blood diseases,rheumatism,high blood pressure,stroke,migraine,various skin diseases,acne, and so forth. In this dissertation, the chemical components of Mahkota Dewa had been investigated systematically. Some derivatives of Mahkoside A were designed and synthesized based on the extraction and isolation of the plant. The vitro bioactivity of them were studies.1. Five compounds were isolated from the fruits of Mahkota Dewa by using various chromatogrm and were elucidated by NMR, HR-MS, IR, et al. The structural of the compounds were: myristic acid,β-sitosterol-3-O-β-D-glucoside,Mahkoside A,mangiferin, glucose.2. To develope a method of extract of the content of Mahkoside A in the seed of Mahkota Dewa. The Mahkoside A was determined by spectrophotometry with Mahkoside A standard, using ultrasonic extraction and reflux extraction, respectively. The ultrasonic extraction was better than reflux extraction and was simple, reproducible and suitable for the determination of Mahkoside A. The method of isolation of the content of Mahkoside A in the seed of Mahkota Dewa was studies based on the analyses of the chemical components. Mahkoside A was isolated and purified. The method was simple and had high extraction yield.3. Mahkoside A was a new derivative of benzophenone, which often exhibited a wide range of biological and pharmacological activities, e.g., antioxidant, cytotoxic, antiinflammatory, antimicrobial, antifungal, and inhibitory effects on xanthine oxidase and monoamine oxidase. In order to study the structure-activity relationship of Mahkoside A derivatives, the target compound 6-O-alkylamine derivatives were synthesized via selective protection, hydrolyze, reacting with dibromoethane, subsequent substitution of bromo group with different amino groups and deprotection. On the other hand, We attempted to use the basic PTC conditions (Bu₄NBr, K₂CO₃, CHCl₃/H₂O) in the glycosylation of benzophenone 4b with 2, 3, 6-tri-O-acetyl-4-chloro-4-deoxy-α-D-galactopyranosidyl bromide and successfully gave 4h. The structures of the derivatives were confirmed by IR, NMR, HR-MS spectra. The 4, 4'-di-O-benzyl group on 4h were then completly cleaved by hydrogenolysis in the catalysis of Pd-C under normal pressure and the acetate groups on the sugar moiety were removed with NaOH in methanol to afford new glycoside 4i.4. 12 compounds were prepared and ten of them were new compounds. The vitro bioactivity of Mahkoside A derivatives were studies. Preliminary structure-activity relationship study showed compounds 4d and 4e having obvious cytotoxic activities (IC₅₀: 30.0and 12.5μg·mL^-1,respectively).In conclusion, the method of extract of the content of Mahkoside A in the seed of Mahkota Dewa was studies based on the analyses of the chemical components, using ultrasonic extraction and reflux extraction, respectively. The derivatives were designed and synthesized. 17 compounds were isolated and synthesized altogether, and 10 of them were new compounds. Their structures were confirmed by IR, NMR, HR-MS spectra. The vitro bioactivity of them was studies.