STUDY ON SYNTHESIS AT LABORATORY SCALE AND STRUCTURE DETERMINATION OF VINIFERIFURAN
Main Article Content
Abstract
Background: Viniferifuran is a secondary metabolite belonging to the dimer group of stilben polyphenols, containing benzofuran rings in the structure. This compound was reported to possess high and diverse biological effects such as antioxidant, anti-inflammatory, anti-cancer, protecting cells from radiation damage. Objectives: In this study, we synthesized viniferifuran from monomer resveratrol at laboratory scale. Materials and methods: Viniferifuran was synthesized through four stages: From resveratrol, biomimetic reaction was done with using FeCl3 catalyst to form a mixture; Through purifying by using classical column chromatography, we obtained a viniferin mixture; Next, we acetylated this mixture and continued doing aromatic reaction with 2,3Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to convert dihydrobenzofuran to benzofuran; After that, alkalization of the product would yield pure viniferifuran; The product after synthesis was conducted to identify the structure by modern spectral method NMR. Results: After reaction and refining steps, we were successful to obtain viniferifuran from resveratrol. The study described the implementation process, the conditions of each reaction phase and interpreted the structural spectrum. Conclusion: We built successfully the synthesis process of viniferifuran at laboratory scale, based on specific experimental conditions at Can Tho University of Medicine and Pharmacy laboratory. The research results have the potential to be applied in the synthesis of pharmaceutical chemistry, serving the synthesis of new potential bioactive compounds.
Article Details
Keywords
viniferifuran, polyphenol, resveratrol, natural compounds, organic chemosynthesis, spectral analysis methods, MS, NMR
References
2. J. Ito, Y. Takaya, Y. Oshima and M. Niwa (1999), New Oligostilbenes Having a Benzofuran from Vitis vinifera 'Kyohou'. Tetrahedron, 55, pp 2529-2544.
3. Jiang M., Li R., Chen Y., Zheng Q., Fan S., & Liu P. (2014), A Combined Experimental and Computational Study of Vam 3, a Derivative of Resveratrol, and Syk Interaction. International Journal of Molecular Sciences, 15(9), pp 17188–17203.
4. Jung Y., Singh D. K., & Kim I. (2016) , Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G. Beilstein Journal of Organic Chemistry, 12, pp 2689–2693.
5. Krzyzanowski, A., Saleeb, M., & Elofsson, M. (2018), Synthesis of Indole-, Benzo[b]thiophene-, and Benzo[b]selenophene-Based Analogues of the Resveratrol Dimers Viniferifuran and (±)-Dehydroampelopsin B. Organic Letters, 20(21), pp 6650-6654.
6. Mattio, L.M., Dallavalle, S., Musso, L. et al. (2019), Antimicrobial activity of resveratrolderived monomers and dimers against foodborne pathogens. Scientific Reports, 9(1).
7. Snyder, S.A., Zografos, A.L. and Lin (2007), Total synthesis of resveratrol based natural products: A chemoselective solution. Angewandte Chemie International Edition, 46, pp 8186-8191.
8. Vo, D. D., & Elofsson, M. (2016), Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues - Investigation of Demethylation Strategies. Advanced Synthesis & Catalysis, 358(24), pp 4085–4092.
9. Yi-tang Li, Chun-suo Yao, Jin-ye Bai, Mao Lin, Gui-fang Cheng (2006), Antiinflammatory effect of amurensin H on asthma-like reaction induced by allergen in sensitized mice. Acta Pharmacologica Sinica, 27, pp 735–740.
10. Zhu W, Sun S, Yang F, Zhou K. (2018), UHPLC/MS Identifying Potent α-glucosidase Inhibitors of Grape Pomace via Enzyme Immobilized Method. Journal of Food Science, 83(4), pp 1131-1139.