Review on Chemical-Biological Fields of Chalcone Compounds

Authors

  • Nagham Mahmood Aljamali Author
  • Shaymaa Hamzah Daylee Author
  • Afaq Jaber Kadhium Author

DOI:

https://doi.org/10.5281/zenodo.10441313

Keywords:

chalcone, aldol, application, carbanion, reaction

Abstract

Chalcones as a chemical compound became an object of sustained interest in each fields( academia besides and industry). Currently, numerous chalcones derivatives are applied  to treatment of viral disorders, cardiovascular infections, parasitic toxicities, pain, gastritis, besides  stomach tumor, as well as like food flavors with cosmetic formulation ingredients. However, abundant of the medicinal potential of chalcones is remain  not utilized. The aim of this survey  is to refer to chalcone importance, applications, preparations, reactions besides to  scientists in the pharmacological screening of formatted chalcones, studying importance of chalcone, with preparation of pharmacologically active chalcones  with their biological activities. Certainly occurring chalcones have been applied  in traditional medicine to numerous years; however, topical scientific advances have appeared  that these compounds  have a capacious range of biological activities in a multiplicity of organisms. A survey on the main sources of chalcones besides the main compounds  events convoluted in the modes of exploit of these natural compounds is achieved. Chalcones are chemical  compounds with a broad spectrum of biological activities, that are of great concentration in agriculture to control weeds besides  unwanted pests.

References

Abe, I. and Morita, H. (2010). "Structure and function of the chalcone synthase superfamily of plant type III polyketide synthases". Natural Product Reports 27, 809–38.

Altman, F. (1976). Tetrazolium salts and formazans. Prog. Histochem. Cytochem. 9, 1–56. Angius, F., Floris, A., 2015. Liposomes and MTT cell viability assay: an incompatible affair. Toxicol. In Vitro 29, 314–319.

AseelMahmoodJawad., Mostafa, N. M. S., Thanaa, A. H., Nadia, H. O. and NaghamMahmoodAljamali. (2019). Review on Chalcone (Preparation ,Reactions, Medical and Bio Applications). International Journal of Chemical Synthesis and Chemical Reactions 5, 16–27.

Austin, M. and Noel, J. (2003). "The chalcone synthase superfamily of type III polyketide synthases". Nat Prod Rep 20, 79–110.

Aziz, D. (2006). Assessment of bovine sperm viability by MTT reduction assay. Anim. Reprod. Sci 92, 1–8.

Berlowska, J., Kregiel, D., Klimek, L., Orzeszyna, B. and Ambroziak, W. (2006). Novel yeast cell dehydrogenase activity assay in situ. Pol. J. Microbiol. 55, 127–131.

Bernas, T. and Dobrucki, J. (2000). The role of plasma membrane in bioreduction of two tetrazolium salts, MTT,and CTC. Arch. Biochem. Biophys 380, 108–116.

Bernas, T. and Dobrucki, J. (2002). Mitochondrial and nonmitochondrial reduction of MTT: interaction of MTT with TMRE, JC-1, and NAO mitochondrial fluorescent probes. Cytometry 47, 236–242.

Bernas, T. and Dobrucki, J. (2004). Backscattered light confocal imaging of intracellular MTT-formazan crystals. Microsc. Res. Tech 64, 126–134.

Berridge, M., Herst, P. and Tan, A. (2015). Tetrazolium dyes as tools in cell biology: new insights into their cellular reduction. Biotechnol. Annu. Rev 11, 127–152.

Berridge, M. and Tan, A. (1993). Subcellular localization, substrate dependence and involvement of mitochondrial electron transport in MTT reduction. Arch. Biochem. Biophys 303, 474–482.

Bradley, P., Kress, N., Hornberger, B., Dallinger, R. and Woodruff, W. (1981). Vibrational spectroscopy of the electronically excited state. 5. Time-resolved resonance Raman study of tris(bipyridine) ruthenium(II) and related complexes. Definitive evidence for the “localized” MLCT state. J. Am. Chem. Soc 103, 7441–7446.

Cain, C., Saslowsky, D., Walker, R. and Shirley, B. (1997). "Expression of chalcone synthase and chalconeisomerase proteins in Arabidopsis seedlings". Plant Mol. Biol. 35, 377–81.

Carmichael, J., DeGraff, W., Gazdar, A., Minna, J. and Mitchell, J. (1987). Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of chemosensitivity testing. Cancer Res 47, 936–942.

Choi, O., Wu, C., Kang, S., Ahn, J., Uhm, T. and Hong, Y. (2011). "Biosynthesis of plant-specific phenylpropanoids by construction of an artificial biosynthetic pathway in Escherichia coli". Journal of Industrial Microbiology and Biotechnology 38, 1657–65.

Crosby, K., Pietra, B., Gadella, T. and Winkel, B. (2011). "Förster resonance energy transfer demonstrates a flavonoidmetabolon in living plant cells that displays competitive interactions between enzymes". FEBS Lett 585, 2193–8.

Dao, T., Linthorst, H. and Verpoorte, R. (2011). "Chalcone synthase and its functions in plant resistance". Phytochem Rev. 10, 397–412.

David, U. (2015). Synthesis and pharmacological applications of chalcones- a review. International Journal of Chemical Sciences 13, 459–500.

Fabiane, L., Michel, G., Andra, T. and Santos, A. (2003). Trypanocida and leshmanicidal properties of substitution containing chalcones. Am. Soc. Microbiol 47, 1449–1451.

Fabio, S., Benvenuti, S., Costantino, L. and Vampa, G. (1998). Synthesis and activity of a new series of chalcone as aldose reductase inhibitor. Eur. J. Med. Chem 33, 859–866.

Garn, H., Krause, H., Enzmann, V. and Drossler, K. (1994). An improved MTT assay using the electron-coupling agent menadione. Journal of Immunological Methods 168, 253–256.

Hinderer, W. and Seitz, H. (1985). "Chalcone synthase from cell suspension cultures of Daucuscarota L". Arch BiochemBiophys. 240, 265–72.

Hrazdina, G. and Wagner, G. (1985). "Metabolic pathways as enzyme complexes: evidence for the synthesis of phenylpropanoids and flavonoids on membrane associated enzyme complexes". Arch. Biochem. Biophys 237, 88–100.

Hu, B., Yao, H., Peng, X., Wang, R., Li, F., Wang, Z., Zhao, M. and Jin, L. (2019). Overexpression of Chalcone Synthase Improves Flavonoid Accumulation and Drought Tolerance in Tobacco. Preprints 6, 103 –110.

Hzardina, G. and Jensen, R. (1992). "Spatial organization of enzymes in plant metabolic pathways". Annu Rev Plant Physiol Plant Mol Biol. 43, 241–67.

Intisar, O. A., Nuha, S. S., Zainab, M. J. and NaghamMahmoodAljamali. (2017). "Synthesis of New Organic Compounds Via Three Components Reaction with Studying of (Identification ,Thermal Behavior, Bioactivity on Bacteria of Teeth)". Journal of Global Pharma Technology 11, 157–164.

Jez, J., Bowman, M., Dixon, R. and Noel, J. (2000). "Structure and mechanism of the evolutionarily unique plant enzyme chalconeisomerase". Nat. Struct. Biol 7, 786–91.

Jiang, C., Schommer, C., Kim, S.-Y. and Suh, D.-Y. (2006). "Cloning and Characterization of Chalcone Synthase from the moss Physcomitrella patens". Phytochemistry 67, 2531–2540.

Kane, M., Steele, C. and Grabau, L. (1997). Early-maturing soybean cropping system: I. Yield responses to planting date. Agron. J., 89, 454–458.

Kim, S., Park, M., Lee, M., Sung, S. and Park, E. (2002). Flavonoids of Inula Britannica protect cultured cortical cells from necrotic cell death by glutamate. Free Radical Biology and Medicine 32, 596–604.

Kim, S., Zo, J., Kim, M. and Hwang, KK.and Chae, I. (2003). Naringin suppresses the mitogenic effect of lysophosphatidylcholine on vascular smooth muscle cells. Nutrition Research 23, 1671–1683.

Kreuzaler, F. and Hahlbrock, K. (1972). "Enzymatic synthesis of aromatic compounds in higher plants: formation of naringenin (5,7,4’-trihydroxyflavanone) from p-coumaroyl coenzyme A and malonyl coenzyme A". FEBS Let 28, 69–72.

Le, B., Jean-Christophe., Pouget, C., Fagnere, C., Basly, J.-P., Chulia, A.-J. and Habrioux, G. (2001). "Chalcones are potent inhibitors of aromatase and 17 β-hydroxysteroid dehydrogenase activities". Life Sciences. 68, 751–61.

Leusink, A. J. and Noltes, J. G. (1966). "Reaction of organo-tin hydrides with α,β-unsaturated ketones". Tetrahedron Letters 7, 2221–5.

Lim, S., Loh, H., Ting, K., Bradshaw, T. and Zeenathul, N. (2013). Acalyphawilkesiana ethyl acetate extract enhances the in vitro cytotoxic effects of α-tocopherol in human brain and lung cancer cells. International Journal of Bioscience, Biochemistry and Bioinformatics 3, 335–340.

Lim, S., Ting, K., Bradshaw, T., Zeenathul, N., Wiart, C., Khoo, T., Lim, K. and Loh, H. (2011). Acalyphawilkesiana extracts induce apoptosis by causing single strand and double strand DNA breaks. Journal of Ethnopharmacology 138, 616–623.

Lin, H., Juan, S., Shen, S., Hsu, F. and Chen, Y. (2003). Inhibition of lipopolysaccharide-induced nitric oxide production by flavonoids in RAW264.7 macrophages involved heme oxygenase-1. Biochemical Pharmacology 66, 1821–1832.

Lin, Y., Zhou, Y., Flavin, M., Zhou, L., Nie, W. and Chen, F. (2002). Chalcones and flavonoids as anti tuberculosis agents. Bioorg. Med. Chem 10, 2795–2802.

McLaughlin, P. and Weihrauch, J. (1979). Vitamin E content of foods. Journal of the American Dietetic Association. 75, 647–665.

M.S., S. and et, a. (1990). Insect antifeedant activity associated with compounds isolated from species of Lonchocarpus and Tephrosia. J Chem Ecol 16, 365–80.

NaghamMahmoodAljamali (2014). Synthesis and Investigation of Formazane compounds (Azo– Imine) and their complexes. Asian J. Research Chem 7, 225–231.

NaghamMahmoodAljamali (2015a). Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)". Research J. Pharm. and Tech 8, 78–84.

NaghamMahmoodAljamali (2015b). Intisar ObaidAlfatlawi. 2015. "Synthesis of Sulfur Heterocyclic Compounds and Study of Expected Biological Activity". Research J. Pharm. and Tech 8, 1225– 1242.

NaghamMahmoodAljamali (2015c). "Synthesis and Chemical Identification of Macro Compounds of (Thiazol and Imidazol)". Research J. Pharm. and Tech, 8, 78–84.

NaghamMahmoodAljamali (2016). "Synthesis and Biological Study of Hetero (Atoms and Cycles) Compounds". Der Pharma- Chemica 8, 40–48.

NaghamMahmoodAljamali (2018a). "Reactions and Mechanisms"., 1 Edt.,. IJMRA Publication.

NaghamMahmoodAljamali (2018b). "Review :General Princeples in Chemistry". 5, 60– 91.

NaghamMahmoodAljamali (2019). "The Various Preparation Methods in Synthetic Chemistry". 1Edt. ,Evincepub Publishing house.

NaghamMahmoodAljamali., Alaa, A. H. and Intisar, O. A. (2019a). Review on Organic Ligands with Their Various Applications. International Journal of Chem-informatics Research 5, 41–53.

NaghamMahmoodAljamali., AseelMahmoodJawad., Aseel, F. K. and Nour, A. A. (2019b). Review in Chemical Structures of Common

Compounds. International Journal of Chemical Synthesis and Chemical Reactions 5, 1–15.

NaghamMahmoodAljamali., RashaNeama, H., AafaqJaberAlnajem., Ali, J. and AfaqJaberKadhium. (2016). Studying of (Chemical, Physical, Biological)–Applications of Oxo-Sulfur Derivatives.,. Journal of Natural Sciences Research 6, 7.

Naida, I. M. A., Nadia, I. M., Alkurbasy, N. I. and Al-kirbasee., N. E. (2015). NATURAL BOND ORBITAL (NBO) POPULATION ANALYSIS

OF OS3 (CO) 10M-PH2PC (ME) 2PPH2. Journal of Research in Applied, Natural and Social Sciences 1, 111–118.

Napoli, C., Lemieux, C. and Jorgensen, R. (1990). "Introduction of a Chimeric Chalcone Synthase Gene into Petunia Results in Reversible Co-Suppression of Homologous Genes in trans". Plant Cell 2, 279–289.

Natarajan, M., Mohan, S., Martinez, B., Meltz, M. and Herman, T. (2000). Antioxidant compounds interfere with the 3-(4, 5- dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide cytotoxic assay. Cancer Detection and Prevention. 24, 405–414.

Nemes, Z., Dietz, R. and Luth, J. (1979). The pharmacological relevance of vital staining with neutral red. Experientia 35, 1475–1476.

Nikolic, K. and Agababa, D. (2009). Design and QSAR study of analogs of γ-tocotrienol with enhanced antiproliferative activity against human breast cancer cells. Journal of Molecular Graphics and Modelling 27, 777–783.

Peng, L., Wang, B. and Ren, P. (2005). Reduction of MTT by flavonoids in the absence of cells. Colloids and Surfaces B:Biointerfaces 45, 108–111.

RajaaAbdulAmeerGhafilm. and Ghafil, R. A. (2019). "Schiffchalconederivatives (preparation, investigation, antibacterial assay)". Int. J. Pharm. Res 11, 657–666.

RanaNeama., NaghamMahmoodAljamali., RanaNeamaAtiya. and MjedJeri. (2014). Synthesis, Identification of Heterocyclic Compounds and Study of Biological Activity. Asian J. Research Chem 7, 664–676.

Repetto, G., delPeso, A. and Zurita, J. (2008). Neutral red uptake assay for the estimation of cell viability/cytotoxicity. Nature Protocols 3, 1125–1131.

Sakai, M., Okabe, M., Tachibana, H. and Yamada, K. (2006). Apoptosis induction by γ-tocotrienol in human hepatoma Hep3B cells. Journal of Nutritional Biochemistry 17, 672–676.

Sangeetha, V., Govindarajan, M., Kanagathara, N., Marchewka, M., Gunasekaran, S. and Anbalagan, G. (2014). Vibrational, DFT, thermal and dielectric studies on 3-nitrophenol-1,3,5-triazine- 2,4,6-triamine (2/1).SpectrochimicaActa Part A:. Molecular and BiomolecularSpectroscopy 118, 1025.

Saslowsky, D. and Winkel-Shirley, B. (2001). "Localization of flavonoid enzymes in Arabidopsis roots". The Plant Journal 27, 37–48.

Schulze, L., Becker, A., Schulr, W., Hahlbrock, K. and Dangl, J. (1989). "Functional architecture of the lightresponsive chalcone synthase promoter from parsley". Plant Cell 1, 707–14.

Shoemaker, M., Cohen, I. and Campbell, M. (2004). Reduction of MTT by aqueous herbal extracts in the absence of cells. Journal of Ethnopharmacology 93, 381–384.

Star, A. (1980). Frond exudate flavonoids as allelopathic agents in Pityrogramma. Bull Torrey Bot Club 107, 146–53.

Sun, W., Xu, W., Liu, H., Liu, J., Wang, Q., Zhou, J., Dong, F. and Chen, B. (2009). γ -tocotrienol induces mitochondria-mediated apoptosis in human gastric adenocarcinoma SGC-7901 cells. Journal of Nutritional Biochemistry 20, 276–284.

Svetaz, L. and et, a. (2004). Antifungal chalcones and new caffeic acid esters from Zuccagniapunctata acting against soybean infecting fungi. J Agric Food Chem 52, 3297–300.

Sylvie, D., Richard, F., John, H., Alex, K. and Nicholas, J. (1998). Potent antimitotic and cell growth inhibitory properties of substituted chalcones. Bioorg. Med. Chem. Lett., 8, 1051–1056.

Takahashi, K. and Loo, G. (2004). Disruption of mitochondria during tocotrienol-induced apoptosis in MDA-MB-231 human breast cancer cells. Biochemical Pharmacology 67, 315–324.

Thirunarayanan, G. and Vanangamudi, G. (2014). Synthesis, spectral studies, antimicrobial and insect antifeedant activities of some substituted styryl 42 -fluorophenyl ketones. Arabian J Chem 7, 1055–64.

Thom, S., Horobin, R., Seidler, E. and Barer, M. (1993). Factors affecting the selection and use of tetrazolium salts as cytochemical indicators of microbial viability and activity. Journal of Applied Bacteriology 74, 433–443.

Tohge, T., Yonekura-Sakakibara, K., Niida, R., Wantanabe- Takahasi, A. and Saito, K. (2007). "Phytochemical genomics in Arabidopsis thaliana: A case study for functional identification of flavonoid biosynthesis genes". Pure and Applied Chemistry 79, 811–23.

VanBlokland, R., VanderGeest, N., MolJNM. and Kooter, J. (1994). "Transgene-mediated suppression of chalcone synthase expression in Petunia hybrida results from an increase in RNA turnover". Plant J 6, 861–77.

Venkatesan, P. and Sumathi, S. (2009). "Piperidinemediated synthesis ofn-heterocyclic chalcones and their antibacterial activity". Journal of Heterocyclic Chemistry 47, 81–84.

Verpoorte, R. and Alfermann, A. (2000). Metabolic engineering of plant secondary metabolism. Dordrecht. Kluwer Academy.

Vibhute, Y. and Baseer, M. (2003). Synthesis and activity of a new series of chalcones as antibacterial agent. Ind. J. Chem. 42, 202–205.

Vishnu, J., Abhishek, S., Shalini, S. and Subhash, C. (2000). Oxygenated chalcones and bischalcones as potential antimalarial agents. Bioorg. Med. Chem. Lett., 10, 2159–2161.

Vogel, A., Tatchell, A., Furnis, B.S.and Hannaford, A. and Smith, P. (1996). Vogel’s Textbook of Practical Organic Chemistry. 5th Edn., Prentice Hall, New York 5.

Watson, R. and Preedy, V. (2008). Tocotrienols: Vitamin E beyond tocopherols. New York: CRC Press.

Whitehead, J. and Dixon, R. (1983). "Chalcone synthase from cell suspension cultures of Phaseolus vulgaris L". BiochimBiophys- Acta 747, 298–303.

Winckler, J. (1974). Vital staining of lysosomes and other cell organelles of the rat with neutral red. Progress in Histochemistry and Cytochemistry 6, 1–91.

Xu, W., Liu, J., Liu, H., Qi, G., Sun, X., Sun, W. and Chen, B. (2009). Inhibition of proliferation and induction of apoptosis by γ-tocotrienol in human colon carcinoma HT-29 cells. Nutrition 25, 555–566.

Yang, Y. and et. al. (2010). Two new chalcones from leaves of Morusalba L. Fitoterapia 81, 614–6.

Yap, W., Chang, P., Han, H., Lee, D., Ling, M., Wong, Y. and Yap, Y. (2008). γ-tocotrienol suppresses prostate cancer cell proliferation and invasion through multiple-signalling pathways. British Journal of Cancer 99, 1832–1841.

Yarishkin, O. V., Ryu, H. W., Park, J. Y., Yang, M. S., Hong, S. G. and Park, K. H. (2008). "Sulfonatechalcone as new class voltagedependent K+ channel blocker". Bioorganic and Medicinal Chemistry Letters 18, 137–140.

Yerra, K., S., F. and Tzeng, Y. (2004). Synthesis of 2 oxygenated chalcones. Bioorg. Med. Chem., 12, 2679–2686.

Yu, O. and Jez, J. (2008). Nature apos;s assembly line: biosynthesis of simple phenylpropanoids and polyketides. Plant J 54, 750–62.

Yun, M. and et. al. (2009). Selective growth suppression of five annual plant species by chalcone and naringenin correlates with the total amount of 4-coumarate: coenzyme A ligase. Weed BiolManage. 9, 27–37.

Zhang, E. and et. al. (2013). An update on antitumor activity of naturally occurring chalcones. Evidence-Based. ComplAltern Med.

Zhang, Z., TanYa-Jun, Wang, C. S. and Wu, H. (2014). "One-Pot Synthesis of 3,5-Diphenyl-1H-pyrazoles from Chalcones and Hydrazine under Mechanochemical Ball Milling". Heterocycles 89, 103–12.

Zhong, P. and et. al. (2015). Blockage of ROS and NF-êB-mediated inflammation by a new chalcone L6H9 protects cardiomyocytes from hyperglycemia-induced injuries. BiochimBiophyActa 1852, 1230–41.

Downloads

Published

2020-01-31

How to Cite

Review on Chemical-Biological Fields of Chalcone Compounds. (2020). Forefront in Engineering & Technology, 2(1), 9-14. https://doi.org/10.5281/zenodo.10441313