Sustainable Synthesis of Flavone Employing TiO2 Nanoparticles as an Efficient Catalyst

Öz

Green method of producing the beneficial chemical molecule flavone using titanium dioxide (TiO2) nanoparticles as nanocatalysts Flavones, a class of naturally occurring compounds, are widely recognized for their broad-spectrum pharmacological properties, including antibacterial and antifungal activities. In this study, TiO2 nanoparticles were derived and characterized using TLC and FTIR techniques for determination of completion of reaction and functional group. The TiO2 showed a superior catalytic activity in oxidative cyclization reaction of 2’-hydroxyacetophenone with benzaldehyde at mild conditions. The nanocatalyst efficiently catalyzed the reaction re sulting in high yield formation of flavone Flavone has been extensively studied for their multifaceted pharmacological activities including antimicrobial tests.

Anahtar Kelimeler

• Nanotechnology
• Nanocatalyst
• Extraction
• Chalcone
• Flavone
• Antimicrobial activities.

Destekleyen Kurum

G H Raisoni University, Saikheda, Madhya Pradesh, India

Etik Beyan

This study shows that making organic flavone works best when you use TiO2 with the right particle size and surface area. The process is pretty simple fast reactions, good yields, and you only get one main product. Plus, it’s environmentally friendly. Thanks to nanotechnology, we can use nano extraction and nano separation to boost the yield even more

Teşekkür

Thank you

TiO2 Nanoparçacıklarının Etkin Bir Katalizör Olarak Kullanılmasıyla Flavonun Sürdürülebilir Sentezi

Öz

Faydalı kimyasal molekül flavone'un titanyum dioksit (TiO2) nanopartikülleri nanokatalizör olarak kullanılarak yeşil yöntemle üretilmesi Flavonlar, doğal olarak oluşan bileşikler sınıfı olup, antibakteriyel ve antifungal aktiviteler de dahil olmak üzere geniş spektrumlu farmakolojik özellikleri ile yaygın olarak bilinmektedir. Bu çalışmada, TiO2 nanopartikülleri türetilmiş ve reaksiyonun tamamlanmasının ve fonksiyonel grubun belirlenmesi için TLC ve FTIR teknikleri kullanılarak karakterize edilmiştir. TiO2, hafif koşullar altında 2'-hidroksiasetofenonun benzaldehit ile oksidatif siklizasyon reaksiyonunda üstün bir katalitik aktivite göstermiştir. Nanokatalizör, reaksiyonu verimli bir şekilde katalize ederek yüksek verimde flavone oluşumuna yol açmıştır. Flavonlar, antimikrobiyal testler de dahil olmak üzere çok yönlü farmakolojik aktiviteleri nedeniyle kapsamlı bir şekilde incelenmiştir.

Anahtar Kelimeler

• Nanoteknoloji
• Nanokatalizör
• Ekstraksiyon
• Kalkon
• Flavon
• Antimikrobiyal aktiviteler.

Destekleyen Kurum

GH Raisoni Üniversitesi, Saikheda, Madhya Pradesh, Hindistan

Etik Beyan

Bu çalışma, organik flavon üretiminin doğru parçacık boyutu ve yüzey alanına sahip TiO2 kullanıldığında en iyi sonucu verdiğini göstermektedir. İşlem oldukça basit, hızlı reaksiyonlar, iyi verim ve sadece tek bir ana ürün elde ediyorsunuz. Ayrıca, çevre dostudur. Nanoteknoloji sayesinde, verimi daha da artırmak için nano ekstraksiyon ve nano ayırma yöntemlerini kullanabiliriz.

Teşekkür

Teşekkür ederim

Kaynakça

1. R. Kshatriya, V.P. Jejurkar, S. Saha, In memory of Prof. Venkataraman: Recent advances in methodologies of flavone, Tetrahedron, 74, 2018, 811-833.
2. D. Sharma, S. Kumar, J.K. Makrandi, Solid phase Baker-Venkataraman rearrangement under solvent-free condition using grinding technique, Green Chem Lett Rev, 2, 2009, 53-55.
3. D. Liu, J. Yu, J. Cheng, Copper-catalyzed oxidative cyclization of chalcone and benzylic amine leading to 2,5-diaryl oxazoles via carbon-carbon double bond cleavage, Tetrahedron, 70, 2014, 1149-1153.
4. T.P.T. Cushnie, A.J. Lamb, Antimicrobial activity of flavonoids, Int J Antimicrob Agents, 26, 2005, 343-356.
5. M.S.S. Chagas, M.D. Behrens, C.J. Moragas-Tellis, G.X.M. Penedo, A.R. Silva, C.F. Gonçalves-de-Albuquerque, Flavonols and flavones as potential anti-inflammatory, antioxidant, and antibacterial compounds, Oxid Med Cell Longev, 2022, 9966750.
6. A. Ullah, M. Munir, S.L. Badshah, N. Khan, L. Ghani, B. Poulson, A. Emwas, M. Jaremko, Important flavonoids and their role as a therapeutic agent, Molecules, 25, 2020, 5243.
7. K.E. Heim, A.R. Tagliaferro, D.J. Bobilya, Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships, J Nutr Biochem, 13, 2002, 572-584.
8. N. De Meyer, A. Haemers, L. Mishra, H.K. Pandey, L.A.C. Pieters, D.A. Vanden Berghe, A.J. Vlietinck, 4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity, J Med Chem, 34, 1991, 736-746.

9. A.N. Panche, A.D. Diwan, S.R. Chandra, Flavonoids: an overview, J Nutr Sci, 5, 2016, e47.
10. M.L. Chávez-González, L. Sepúlveda, D.K. Verma, H.A. Luna-García, L.V. Rodríguez-Durán, A. Ilina, C.N. Aguilar, Conventional and emerging extraction processes of flavonoids, Processes, 8, 2020, 434.
11. M. Yoshida, M. Hayashi, S. Hinkley, T. Iwasaki, M. Shimizu, Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of alkynoylphenols, Tetrahedron, 67, 2011, 9993-9997.
12. D. Mulugeta, A review of synthesis methods of chalcones, flavonoids, and coumarins, Sci J Chem, 10, 2022, 41-52.
13. S. Jain, S. Kumar, B.Y. Lamba, J. Patra, N. Mahindroo, Nanocatalysts: Applications in synthesis of chalcones-a review, Synth Commun, 51, 2021, 1-12.
14. S. Abdolmohammadi, TiO2 nanoparticles as an effective catalyst for the synthesis of hexahydro-2-quinolinecarboxylic acids derivatives, Chin Chem Lett, 23, 2012, 1003-1006.
15. K.V. Sashidhara, M. Kumar, A. Kumar, A novel route to synthesis of flavone from salicylaldehyde and acetophenone derivatives, Tetrahedron Lett, 53, 2012, 2355-2359.
16. H. Wang, A.D. Campiglia, Direct determination of benzo[a]pyrene in water samples by a gold nanoparticle-based solid phase extraction method and laser-excited time-resolved Shpol'skii spectrometry, Talanta, 83, 2010, 233-240.
17. S.O. Majekodunmi, A review on centrifugation in the pharmaceutical industry, Am J Biomed Eng, 5, 2015, 67-78.
18. S. Tripathi, R. Kapoor, L.D.S. Yadav, Visible light activated radical denitrative benzoylation of β-nitrostyrenes: A photocatalytic approach to chalcones, Adv Synth Catal, 360, 2018, 1407-1413.
19. A. Wang, F. Zhang, L. Huang, X. Yin, H. Li, Q. Wang, Z. Zeng, T. Xie, New progress in biocatalysis and biotransformation of flavonoids, J Med Plants Res, 4, 2010, 847-856.
20. Z. Wang, L. Yang, X. Yang, X. Zhang, Advances in the first total synthesis of natural flavonoids, Synth Commun, 43, 2013, 3093-3114.
21. M.A. Pfaller, D.J. Diekema, Epidemiology of invasive candidiasis: a persistent public health problem, Clin Microbiol Rev, 20, 2007, 133-163.
22. F. Farhadi, B. Khameneh, M. Iranshahi, M. Iranshahy, Antibacterial activity of flavonoids and their structure-activity relationship: An update review, Phytother Res, 33, 2019, 13-40.
23. E.U. Mughal, M. Ayaz, Z. Hussain, A. Hasan, A. Sadiq, M. Riaz, A. Malik, S. Hussain, M.I. Choudhary, Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones, Bioorg Med Chem, 14, 2006, 4704-4711.
24. J.B. Harborne, Advances in flavonoid research since 1992, Phytochemistry, 55, 2000, 481-504.
25. U. Diebold, The surface science of titanium dioxide, Surf Sci Rep, 48, 2003, 53-229.
26. M.A. Behnajady, N. Modirshahla, R. Hamzavi, Investigation of the effect of sol-gel synthesis variables on structural and photocatalytic properties of TiO2 nanoparticles, Desalination, 278, 2011, 10-17.
27. A.H. Lu, E.L. Salabas, F. Schüth, Magnetic nanoparticles: synthesis, protection, functionalization, and application, Angew Chem Int Ed, 46, 2007, 1222-1244.
28. J.H. Clark, S.J. Tavener, Alternative solvents: shades of green, Org Process Res Dev, 11, 2007, 149-155.
29. D. Astruc, Nanoparticles and Catalysis, 2008, Weinheim, Wiley-VCH.
30. A. Fujishima, T.N. Rao, D.A. Tryk, Titanium dioxide photocatalysis, J Photochem Photobiol C, 1, 2000, 1-21.
31. P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, 2000, Oxford, Oxford University Press.
32. V. Polshettiwar, R.S. Varma, Green chemistry by nano-catalysis, Green Chem, 12, 2010, 743-754.
33. A. Corma, H. Garcia, Supported gold nanoparticles as catalysts for organic reactions, Chem Soc Rev, 37, 2008, 2096-2126.
34. M. Aravind, M. Amalanathan, M.S.M. Mary, Synthesis of TiO2 nanoparticles by chemical and green synthesis methods and their multifaceted properties, SN Appl Sci, 3, 2021, 1-10.
35. H. Venkatachalam, Y. Nayak, B.S. Jayashree, Synthesis, characterization and antioxidant activities of synthetic chalcones and flavone, APCBEE Procedia, 3, 2012, 209-213.
36. R.N.S. Santiago, P.T.C. Freire, A.M.R. Teixeira, P.N. Bandeira, H.S. Santos, T.L.G. Lemos, C.A.N. Ferraz, FT-Raman and FT-IR spectra and DFT calculations of chalcone (2E)-1-(4-aminophenyl)-3-phenyl-prop-2-en-1-one, Vib Spectrosc, 97, 2018, 1-7.
37. Y. Erdoğdu, O. Ünsalan, M.T. Güllüoğlu, Vibrational analysis of flavone, Turk J Phys, 33, 2009, 249-260.
38. Y. Yong, S. Ahn, D. Hwang, H. Yoon, G. Jo, Y.H. Kim, S.H. Kim, D. Koh, Y. Lim, 1H and 13C NMR spectral assignments of 2′-hydroxychalcones, Magn Reson Chem, 51, 2013, 364-370.
39. Y. Park, B.H. Moon, E. Lee, Y. Lee, Y. Yoon, J.H. Ahn, Y. Lim, 1H and 13C-NMR data of hydroxyflavone derivatives, Magn Reson Chem, 45, 2007, 674-679.
40. D.W. Aksnes, A. Standnes, Ø.M. Andersen, Complete assignment of the 1H and 13C NMR spectra of flavone and its A-ring hydroxyl derivatives, Magn Reson Chem, 34, 1996, 820-823.