DOI: https://doi.org/10.14710/jksa.23.2.51-60

Microwave-assisted synthesis of 1-(4-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one and its activities as an antioxidant, sunscreen, and antibacterial

1Sekolah Tinggi Ilmu Farmasi Riau, Indonesia

2Universitas Riau, Indonesia

Received: 9 Dec 2019; Revised: 10 Feb 2020; Accepted: 24 Feb 2020; Published: 29 Feb 2020.
Open Access Copyright 2020 Jurnal Kimia Sains dan Aplikasi under http://creativecommons.org/licenses/by-sa/4.0.

Citation Format:
Cover Image
Abstract
Chalcone analogs have been reported to have a variety of exciting biological activities, such as anticancer, anti-inflammatory, antioxidant, photoprotective, antibacterial, and antidiabetic activities. Therefore, analogs of these compounds have been widely synthesized as intermediate compounds or target molecules in the discovery of bioactive compounds to be applied in the pharmaceutical field. The purpose of this study is to synthesize chalcone analog compounds (E)-1-(4-hydroxyphenyl)-3-(4-methoxyphenyl) prop-2-en-1-on with the microwave irradiation method and explore some of the biological activities of these compounds, including testing the antioxidant activity by 1,1-diphenyl-2-picrylhydrazyl (DPPH) method, in vitro sunscreen activity by microplate method, and antibacterial activity by disk diffusion method. DPPH test results indicate that the compound has weak antioxidant activity, with an IC50 value of 300.43 µg/mL. However, the compound showed excellent potential as a UV B and UV A filter at a concentration of 150 µg/mL with a value of %Te of 0.73±0.10% (sunblock), %Tp of 0.07±0.00% (sunblock), SPF value of 21.10±1.46 (ultra-protection) and potentially better than benzophenone-3 as a standard sunscreen. Then, disk diffusion testing showed that the compound had weak antibacterial activity against Staphylococcus aureus and did not show antibacterial activity against Escherichia coli bacteria at test concentrations of 30, 60, and 120 µg/disk.

Note: This article has supplementary file(s).

Fulltext View|Download |  Research Results
(E)-1-(4-hidroksifenil)-3-(4-metoksifenil)prop-2-en-1-on
Subject Analog kalkon, antioksidan, DPPH, tabir surya, difusi cakram
Type Research Results
  Download (555KB)    Indexing metadata
Email colleagues
Keywords: chalcone analog; antioxidant; DPPH, sunscreen; disk diffusion
Funding: DPRM Kementrian Riset Teknologi dan Pendidikan Tinggi (KEMENRISTEK DIKTI) melalui hibah Penelitian Dosen Pemula (PDP) tahun 2019 dengan nomor kontrak penelitian 06.15.LP2M.STIFAR.V.2019.

Article Metrics:

Article Info
Section: Research Articles
Language : EN
Most cited articles
Hidrorengkah Fraksi Berat Minyak Bumi Menggunakan Katalis Lempung Terpilar Aluminium Berpengemban Nikel Antioxidant Activity of Daemonorops draco Resin New Chemicals and Routes for the Preparation of Gelatin/HA Composites using the Wet Precipitation Method Studi Filogeni dan Uji Potensi Bioremediasi serta Enzim Termostabil Ekstraseluler Isolat Geobacillus sp. dari Sumber Air Panas Gedong Songo Sintesis Bahan Hibrida Amino-Silika dari Abu Sekam Padi Melalui Proses Sol-Gel More cited articles
  1. N. K. Sahu, S. S. Balbhadra, J. Choudhary and D. V. Kohli, Exploring Pharmacological Significance of Chalcone Scaffold: A Review, Current Medicinal Chemistry, 19, 2, (2012), 209-225 http://dx.doi.org/10.2174/092986712803414132
  2. Zhou Tiezhong, Xu Ming Deng and Jia Zhang Qiu, Antimicrobial activity of licochalcone E against Staphylococcus aureus and its impact on the production of staphylococcal alpha-toxin, Journal of microbiology and biotechnology, 22, 6, (2012), 800-805 https://doi.org/10.4014/jmb.1112.12020
  3. Ismiyarto Ismiyarto, Suyanti Suyanti, Ngadiwiyana Ngadiwiyana, Purbowatiningrum Ria Sarjono and Nor Basid Adiwibawa Prasetya, Synthesis of 4-Hydroxy-2-Methylchalcone from meta-Cresol Formilation Product and Its Activities as an Antibacteria, Jurnal Kimia Sains dan Aplikasi, 21, 4, (2018), 193-197 https://doi.org/10.14710/jksa.21.4.193-197
  4. Florian George and Toufik Fellague, Compose Chimique De Derive Azote De Chalcone, Procede D’obtention D’un Tel Compose Chimique, Composition Cosmetique Et/Ou Ftltrante Contenant Un Tel Compose Chimique, in: O.M.d.l.P. Intellectuelle (Ed.), France, 2003, pp. 38
  5. Serge Forestier, Claudine Moire and Gerard Lang, Cosmetic composition containing hydroxylated chalcone derivatives and its use for protecting the skin and the hair against luminous radiations, new hydroxylated chalcone derivatives employed and process for their preparation, in: U.S.P. DOCUMENTS (Ed.), L'Oreal, Paris, France, United State, 1989,
  6. Silvina Quintana Lazópulos, Federico Svarc, Gabriel Sagrera and Lelia Dicelio, Absorption and Photo-Stability of Substituted Dibenzoylmethanes and Chalcones as UVA Filters, Cosmetics, 5, 2, (2018), https://doi.org/10.3390/cosmetics5020033
  7. Ihsan Ikhtiarudin, Nesa Agistia, Tria Harlianti and Adel Zamri, Sintesis dan Potensi Aktivitas Tabir Surya Senyawa Analog Kalkon Turunan 3’-Hidroksiasetofenon dan 4-Metoksibenzaldehid, Jurnal Photon, 10, 1, (2019), 1-12
  8. Ihsan Ikhtiarudin, Lelani, Adel Zamri, Hilwan Yuda Teruna and Yuharmen, Sintesis dan Uji Toksisitas Senyawa Analog Kalkon Turunan 2’-Hidroksiasetofenon dan Halobenzaldehid, Jurnal Photon, 5, 1, (2014), 57-63
  9. Ihsan Ikhtiarudin, Neni Frimayanti, Hilwan Y Teruna and Adel Zamri, Microwave-assisted synthesis, molecular docking study and in vitro evaluation of halogen substituted flavonols against P388 Murine leukemia cells, Applied Science and Technology, 1, 1, (2017), 375-381
  10. Neni Frimayanti, Jasril Jasril, Ihsan Ikhtiarudin, Syilfia Hasti and Anisa Indah Reza, Microwave-Assisted Synthesis, in Silico Studies and in Vivo Evaluation for Antidiabetic Activity of New Brominated Pyrazoline Analogues, Thai Journal of Pharmaceutical Sciences (TJPS), 43, 2, (2019), 83-89
  11. Nora M. Rateb and Hussein F. Zohdi, Atom-Efficient, Solvent-Free, Green Synthesis of Chalcones by Grinding, Synthetic Communications, 39, 15, (2009), 2789-2794 https://doi.org/10.1080/00397910802664244
  12. Jae-Chul Jung, Yongnam Lee, Dongguk Min, Mankil Jung and Seikwan Oh, Practical Synthesis of Chalcone Derivatives and Their Biological Activities, Molecules, 22, 11, (2017), https://doi.org/10.3390/molecules22111872
  13. Edmont V. Stoyanov, Yves Champavier, Alain Simon and Jean-Philippe Basly, Efficient liquid-Phase synthesis of 2′-Hydroxychalcones, Bioorganic & Medicinal Chemistry Letters, 12, 19, (2002), 2685-2687 https://doi.org/10.1016/S0960-894X(02)00553-X
  14. Tahseen Razzaq and C. Oliver Kappe, On the Energy Efficiency of Microwave-Assisted Organic Reactions, ChemSusChem, 1, 1‐2, (2008), 123-132 https://doi.org/10.1002/cssc.200700036
  15. Jonathan R. Dimmock, N. Murthi Kandepu, Mark Hetherington, J. Wilson Quail, Uma Pugazhenthi, Athena M. Sudom, Mahmood Chamankhah, Patricia Rose, Eric Pass, Theresa M. Allen, Sarah Halleran, Jen Szydlowski, Bulent Mutus, Marie Tannous, Elias K. Manavathu, Timothy G. Myers, Erik De Clercq and Jan Balzarini, Cytotoxic Activities of Mannich Bases of Chalcones and Related Compounds, Journal of Medicinal Chemistry, 41, 7, (1998), 1014-1026 https://doi.org/10.1021/jm970432t
  16. S Sathiya Moorthi, K Chinnakali, S Nanjundan, P Selvam, H-K Fun and X-L Yu, 3-(3-Hydroxyphenyl)-1-(4-methoxyphenyl) prop-2-en-1-one, Acta Crystallographica Section E: Crystallographic Communications, 61, 3, (2005), o743-o745 https://doi.org/10.1107/S1600536805004915
  17. Halise I. Gul, Kadir O. Yerdelen, Mustafa Gul, Umashankar Das, Bulbul Pandit, Pui-Kai Li, Hasan Secen and Fikrettin Sahin, Synthesis of 4′-Hydroxy-3′-piperidinomethylchalcone Derivatives and Their Cytotoxicity Against PC-3 Cell Lines, Archiv der Pharmazie, 340, 4, (2007), 195-201 https://doi.org/10.1002/ardp.200600072
  18. Halise Inci Gul, Murat Cizmecioglu, Sevil Zencir, Mustafa Gul, Pakize Canturk, Mustafa Atalay and Zeki Topcu, Cytotoxic activity of 4′-hydroxychalcone derivatives against Jurkat cells and their effects on mammalian DNA topoisomerase I, Journal of Enzyme Inhibition and Medicinal Chemistry, 24, 3, (2009), 804-807 https://doi.org/10.1080/14756360802399126
  19. Daniela I. Batovska and Iva Todorova Todorova, Trends in Utilization of the Pharmacological Potential of Chalcones, Current Clinical Pharmacology, 5, 1, (2010), 1-29 https://doi.org/10.2174/157488410790410579
  20. Bio-Rad Laboratories Inc., SpectraBase; SpectraBase Compound ID=1PXrd97MNom SpectraBase Spectrum ID=8HbcjN7xboX, in, 2020,
  21. Ram Pratap, Mavurapu Satyanarayana, Chandeshwar Nath, Ram Raghubir, Anju Puri, Ramesh Chander, Priti Tiwari, Brajendra Kumar Tripathi and Arvind Kumar Srivastava, Oxy Substituted Chailcones as Anthyperglycemic and Antdyslipidemicagents, in, United State, 2006, pp. 19
  22. Philip Molyneux, The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity, Songklanakarin Journal of Science and Technology, 26, 2, (2004), 211-219
  23. Yueting Lu, Rudi Hendra, Aaron J. Oakley and Paul A. Keller, Efficient synthesis and antioxidant activity of coelenterazine analogues, Tetrahedron Letters, 55, 45, (2014), 6212-6215 https://doi.org/10.1016/j.tetlet.2014.09.065
  24. L. R. Fukumoto and G. Mazza, Assessing Antioxidant and Prooxidant Activities of Phenolic Compounds, Journal of Agricultural and Food Chemistry, 48, 8, (2000), 3597-3604 https://doi.org/10.1021/jf000220w
  25. MR Marjoni and A Zulfisa, Antioxidant activity of methanol extract/fractions of senggani leaves (Melastoma candidum D. Don), Pharmaceutica Analytica Acta, 8, 8, (2017), 1-6 https://doi.org/10.4172/2153-2435.1000557
  26. M.S. Balsam and E. Sagarin, Cosmetics, Science and Technology, Krieger Publishing Company, 1992
  27. Elizângela Abreu Dutra, Daniella Almança Gonçalves da Costa e Oliveira, Erika Rosa Maria Kedor-Hackmann and Maria Inês Rocha Miritello Santoro, Determination of sun protection factor (SPF) of sunscreens by ultraviolet spectrophotometry, Revista Brasileira de Ciências Farmacêuticas, 40, (2004), 381-385 https://doi.org/10.1590/S1516-93322004000300014
  28. Fitriyanti Jumaetri Sami, Syamsu Nur and Megawati M Martani, Uji Aktivitas Tabir Surya pada Beberapa Spesies dari Family Zingiberaceae dengan Metode Spektrofotometri, As-Syifaa Jurnal Farmasi, 7, 2, (2015), 164-173
  29. Vivi Anggia, Amri Bakhtiar and Dayar Arbain, The Isolation of xanthones from trunk latex of Garcinia mangostana Linn. and their antimicrobial activities, Indonesian Journal of Chemistry, 15, 2, (2015), 187-193 https://doi.org/10.22146/ijc.21213
  30. Melzi Octaviani, Haiyul Fadhli and Erenda Yuneistya, Uji Aktivitas Antimikroba Ekstrak Etanol Kulit Bawang Merah (Allium cepa L.) dengan Metode Difusi Cakram, Pharmaceutical Sciences & Research, 6, 1, (2019), 62-68 https://doi.org/10.7454/psr.v6i1.4333
  31. E. W. C. Chan, Y. Y. Lim and Mohammed Omar, Antioxidant and antibacterial activity of leaves of Etlingera species (Zingiberaceae) in Peninsular Malaysia, Food Chemistry, 104, 4, (2007), 1586-1593 https://doi.org/10.1016/j.foodchem.2007.03.023
  32. Adel Zamri, Hilwan Yuda Teruna and Ihsan Ikhtiarudin, The influences of power variations on selectivity of synthesis reaction of 2’-hydroxychalcone analogue under microwave irradiation, Molekul, 11, 2, (2016), 299-307 http://dx.doi.org/10.20884/1.jm.2016.11.2.220
  33. Sindhu Mathew, T. Emilia Abraham and Zainul Akmar Zakaria, Reactivity of phenolic compounds towards free radicals under in vitro conditions, Journal of Food Science and Technology, 52, 9, (2015), 5790-5798 https://doi.org/10.1007/s13197-014-1704-0
  34. Satish Balasaheb Nimse and Dilipkumar Pal, Free radicals, natural antioxidants, and their reaction mechanisms, RSC Advances, 5, 35, (2015), 27986-28006 https://doi.org/10.1039/C4RA13315C
  35. E. Bendary, R. R. Francis, H. M. G. Ali, M. I. Sarwat and S. El Hady, Antioxidant and structure–activity relationships (SARs) of some phenolic and anilines compounds, Annals of Agricultural Sciences, 58, 2, (2013), 173-181 https://doi.org/10.1016/j.aoas.2013.07.002
  36. Yogesh Murti, A Goswam and Pradeep Mishra, Synthesis and antioxidant activity of some chalcones and flavanoids, International Journal of PharmTech Research, 5, 2, (2013), 811-818
  37. Siti Hasanah, Islamudin Ahmad and Laode Rijai, Profil Tabir Surya Ekstrak dan Fraksi Daun Pidada Merah (Sonneratia caseolaris L.), Jurnal Sains dan Kesehatan, 1, 4, (2015), 175-180 https://doi.org/10.25026/jsk.v1i4.36
  38. Marvin E Wala, Suryantom Edy and Defny S Wewengkang, Aktivitas Antioksidan Dan Tabir Surya Fraksi Dari Ekstrak Lamun (Syringodium isoetifolium), Pharmacon, 4, 4, (2015), 282-289
  39. Ponnurengam Malliappan Sivakumar, Sobana Priya and Mukesh Doble, Synthesis, Biological Evaluation, Mechanism of Action and Quantitative Structure–Activity Relationship Studies of Chalcones as Antibacterial Agents, Chemical Biology & Drug Design, 73, 4, (2009), 403-415 https://doi.org/10.1111/j.1747-0285.2009.00793.x
  40. Terry J. Beveridge, Structures of Gram-Negative Cell Walls and Their Derived Membrane Vesicles, Journal of Bacteriology, 181, 16, (1999), 4725

Last update:

  1. (E)-5-Benzyl-7-(3,4-dimethoxybenzylidene)-3-(3,4-dimethoxyphenyl)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3c] Pyridine

    Enda Mora, Adel Zamri, Hilwan Y. Teruna, Neni Frimayanti, Ihsan Ikhtiarudin, Noval Herfindo, Elsa Natia Rindiana. Molbank, 2021 (3), 2021. doi: 10.3390/M1240

  2. (E)-4-(3-(3-(4-Methoxyphenyl)acryloyl)phenoxy)butyl 2-Hydroxybenzoate

    Ihsan Ikhtiarudin, Rahma Dona, Neni Frimayanti, Rahayu Utami, Emma Susanti, Mentari Mentari, Nurmaida Nurmaida, Nesa Agistia, Noval Herfindo, Adel Zamri. Molbank, 2021 (1), 2021. doi: 10.3390/M1195

  3. Antifungal Potential of Secondary Metabolites Derived from Arcangelisia flava (L.) Merr.: An Analysis of In Silico Enzymatic Inhibition and In Vitro Efficacy against Candida Species

    Rudi Hendra, Aulia Agustha, Neni Frimayanti, Rizky Abdulah, Hilwan Yuda Teruna. Molecules, 29 (10), 2024. doi: 10.3390/molecules29102373

  4. Microwave-assisted synthesis and antioxidant activity of a hydrazone, (E)-1-(4-methoxybenzylidene)-2- phenylhydrazine

    Jasril, Yuana Nurulita, Nur Afriana, Ihsan Ikhtiarudin, Neni Frimayanti. THE 2ND SCIENCE AND MATHEMATICS INTERNATIONAL CONFERENCE (SMIC 2020): Transforming Research and Education of Science and Mathematics in the Digital Age, 2331 , 2021. doi: 10.1063/5.0042010

Last update: 2026-09-05 06:40:13

No citation recorded.