journal article
Open Access
Jan 13, 2020
Phytochemical Constituents, Antioxidant, Cytotoxic, and Antimicrobial Activities of the Ethanolic Extract of Mexican Brown Propolis
Abstract
Propolis is a complex mixture of natural sticky and resinous components produced by honeybees from living plant exudates. Globally, research has been dedicated to studying the biological properties and chemical composition of propolis from various geographical and climatic regions. However, the chemical data and biological properties of Mexican brown propolis are scant. The antioxidant activity of the ethanolic extract of propolis (EEP) sample collected in México and the isolated compounds is described. Cytotoxic activity was evaluated in a central nervous system and cervical cancer cell lines. Cytotoxicity of EEP was evaluated in a C6 cell line and cervical cancer (HeLa, SiHa, and CasKi) measured by the 3-(3,5-dimethylthiazol-2-yl)2,5-diphenyltetrazolium (MTT) assay. The antibacterial activity was tested using the minimum inhibitory concentration (MIC) assay. Twelve known compounds were isolated and identified by nuclear magnetic resonance spectroscopy (NMR). Additionally, forty volatile compounds were identified by means of headspace-solid phase microextraction with gas chromatography and mass spectrometry time of flight analysis (HS-SPME/GC-MS-TOF). The main volatile compounds detected include nonanal (18.82%), α-pinene (12.45%), neryl alcohol (10.13%), and α-pinene (8.04%). EEP showed an anti-proliferative effect on glioma cells better than temozolomide, also decreased proliferation and viability in cervical cancer cells, but its effectiveness was lower compared to cisplatin.
Topics
No keywords indexed for this article. Browse by subject →
References
44
[1]
Bankova "Standard methods for Apis mellifera propolis research" J. Apic. Res. (2016) 10.1080/00218839.2016.1222661
[2]
Salatino "Propolis research and the chemistry of plant products" Nat. Prod. Res. (2011)
[3]
Kuropatnicki "Historical aspects of propolis research in modern times" Evid. Based Cmnplement. Altern. Med. eCAM (2013)
[4]
Toreti "Recent progress of propolis for its biological and chemical compositions and its botanical origin" Evid. Based Cmnplement. Altern. Med. eCAM (2013)
[5]
Christov "Chemical composition of propolis from canada, its antiradical activity and plant origin" Nat. Prod. Res. (2006) 10.1080/14786410500056918
[6]
Karapetsas, A., Voulgaridou, G.-P., Konialis, M., Tsochantaridis, I., Kynigopoulos, S., Lambropoulou, M., Stavropoulou, M.-I., Stathopoulou, K., Aligiannis, N., and Bozidis, P. (2019). Propolis extracts inhibit UV-induced photodamage in human experimental in vitro skin models. Antioxidants, 8.
10.3390/antiox8050125
[7]
Nna, V.U., Abu Bakar, A.B., Ahmad, A., Eleazu, C.O., and Mohamed, M. (2019). Oxidative stress, NF-κb-mediated inflammation and apoptosis in the testes of streptozotocin–induced diabetic rats: Combined protective effects of malaysian propolis and metformin. Antioxidants, 8.
10.3390/antiox8100465
[8]
Papotti "Chemical and functional characterization of italian propolis obtained by different harvesting methods" J. Agric. Food. Chem. (2012) 10.1021/jf205179d
[9]
Valencia "Antibacterial activity of sonoran propolis and some of its constituents against clinically significant vibrio species" Foodborne Pathog. Dis. (2013) 10.1089/fpd.2012.1318
[10]
Li "Study on the constituents of mexican propolis and their cytotoxic activity against panc-1 human pancreatic cancer cells" J. Nat. Prod. (2010) 10.1021/np900772m
[11]
Li "Cytotoxicity of constituents from mexican propolis against a panel of six different cancer cell lines" Nat. Prod. Commun. (2010)
[12]
Lotti "Chemical constituents of red mexican propolis" J. Agric. Food Chem. (2010) 10.1021/jf100070w
[13]
Cheng "High-throughput relative DPPH radical scavenging capacity assay" J. Agric. Food Chem. (2006) 10.1021/jf0611668
[14]
Zhao "Evaluation of antioxidant activities and total phenolic contents of typical malting barley varieties" Food Chem. (2007) 10.1016/j.foodchem.2007.08.018
[15]
Singleton "Colorimetry of total phenolics with phosphomolybdic-phosphotungstic acid reagents" Am. J. Enol. Vit. (1965) 10.5344/ajev.1965.16.3.144
[16]
Marquele "Assessment of the antioxidant activities of brazilian extracts of propolis alone and in topical pharmaceutical formulations" J. Pharm. Biomed. Anal. (2005) 10.1016/j.jpba.2005.04.004
[17]
"Analysis of volatile components from Melipona beecheii geopropolis from Southeast Mexico by headspace solid-phase microextraction" Nat. Prod. Res. (2016) 10.1080/14786419.2015.1043631
[18]
Adams, R.P. (2007). Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry, Allured Publishing Corporation.
[19]
Linstrom, P.J. (2005). NIST Chemistry Webbook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology.
[20]
Clinical and Laboratory Standards Institute (2018). Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, Clinical and Laboratory Standards Institute. [10th ed.]. M07-A11.
[21]
Escarpa "Approach to the content of total extractable phenolic compounds from different food samples by comparison of chromatographic and spectrophotometric methods" Anal. Chim. Acta (2001) 10.1016/s0003-2670(00)01188-0
[22]
Valencia "Seasonal effect on chemical composition and biological activities of sonoran propolis" Food Chem. (2012) 10.1016/j.foodchem.2011.08.086
[23]
Larrauri "A procedure to measure the antiradical efficiency of polyphenols" J. Sci. Food Chem. (1998) 10.1002/(sici)1097-0010(199802)76:2<270::aid-jsfa945>3.0.co;2-9
[24]
Lima "Main flavonoids, dpph activity, and metal content allow determination of the geographical origin of propolis from the province of San Juan (Argentina)" J. Agric. Food Chem. (2009) 10.1021/jf803866t
[25]
Tominaga "DPPH radical-scavenging effect of several phenylpropanoid compounds and their glycoside derivatives" Yakugaku Zasshi J. Pharm. Soc. Jpn. (2005) 10.1248/yakushi.125.371
[26]
Pengfei "Antioxidant properties of isolated isorhamnetin from the sea buckthorn marc" Plant Foods Hum. Nutr. (2009) 10.1007/s11130-009-0116-1
[27]
Lu "Extraction, purification and antiradical activities of alpinetin and cardamomin from alpinia katsumadai hayata" Asian J. Chem. (2013) 10.14233/ajchem.2013.15046
[28]
Prior "Standardized methods for the determination of antioxidant capacity and phenolics in foods and dietary supplements" J. Agric. Food Chem. (2005) 10.1021/jf0502698
[29]
"Antioxidant and prooxidant properties of flavonoids" Fitoterapia (2011) 10.1016/j.fitote.2011.01.018
[30]
Benguedouar "Ethanolic extract of Algerian propolis and galangin decreased murine melanoma T" Anticancer Agents Med. Chem. (2016) 10.2174/1871520616666160211124459
[31]
Lazarek "Constituents of Propolis: Chrysin, Caffeic Acid, p-Coumaric Acid, and Ferulic Acid Induce PRODH/POX-Dependent Apoptosis in Human Tongue Squamous Cell Carcinoma Cell (CAL-27)" Front. Pharmacol. (2018) 10.3389/fphar.2018.00336
[32]
Velazquez "Antibacterial and free-radical scavenging activities of Sonoran propolis" J. Appl. Microbiol. (2007) 10.1111/j.1365-2672.2007.03409.x
[33]
Bertelli "1H-NMR simultaneous identification of health-relevant compounds in propolis extracts" Phytochem. Anal. (2012) 10.1002/pca.1352
[34]
Wawer "13c cp/mas nmr studies of flavonoids" Magn. Reson. Chem. (2001) 10.1002/mrc.871
[35]
Dominguez "Mexican medicinal plants. Part 38. Flavonoids from Dalea scandens var. Paucifolia and Dalea thyrsiflora" Phytochemistry (1980) 10.1016/0031-9422(80)83108-6
[36]
Rossi "Neolignans, styrylpyrones and flavonoids from an aniba species" Phytochemistry (1997) 10.1016/s0031-9422(97)00075-7
[37]
Hosny "Hydroxylations and methylations of quercetin, fisetin, and catechin by Streptomyces griseus" J. Nat. Prod. (2001) 10.1021/np000457m
[38]
Cao "Preparative isolation of isorhamnetin from Stigma maydis using high-speed countercurrent chromatography" J. Liq. Chromatogr. Relat. Technol. (2009) 10.1080/10826070802603369
[39]
Nagy "Constituents of propolis of Czechoslovak origin. V" Chem. Pap. (1988)
[40]
Estevinho "Phenolic characterization of northeast portuguese propolis: Usual and unusual compounds" Anal. Bioanal. Chem. (2010) 10.1007/s00216-009-3232-8
[41]
Gardana "Analysis of the polyphenolic fraction of propolis from different sources by liquid chromatography–tandem mass spectrometry" J. Pharm. Biomed. Anal. (2007) 10.1016/j.jpba.2007.06.022
[42]
Falcao "Phenolic profiling of portuguese propolis by LC-MS spectrometry: Uncommon propolis rich in flavonoid glycosides" Phytochem. Anal. (2013) 10.1002/pca.2412
[43]
Pellati "Headspace solid-phase microextraction-gas chromatography-mass spectrometry characterization of propolis volatile compounds" J. Pharm. Biomed. Anal. (2013) 10.1016/j.jpba.2013.05.045
[44]
Pino "Volatile constituents of propolis from honey bees and stingless bees from Yucatan" J. Essent. Oil Res. (2006) 10.1080/10412905.2006.9699384
Cited By
120
Anticancer Activity of Propolis and Its Compounds
Nutrients
Ewa Forma, Magdalena Brys · 2021
Metrics
120
Citations
44
References
Details
- Published
- Jan 13, 2020
- Vol/Issue
- 9(1)
- Pages
- 70
- License
- View
Authors
Funding
Consejo Nacional de Ciencia y Tecnología
Award: CB-252006
Cite This Article
J. Fausto Rivero-Cruz, Jessica Granados-Pineda, José Pedraza-Chaverri, et al. (2020). Phytochemical Constituents, Antioxidant, Cytotoxic, and Antimicrobial Activities of the Ethanolic Extract of Mexican Brown Propolis. Antioxidants, 9(1), 70. https://doi.org/10.3390/antiox9010070
Related
You May Also Like
Reactive Oxygen Species and Antioxidant Defense in Plants under Abiotic Stress: Revisiting the Crucial Role of a Universal Defense Regulator
Mirza Hasanuzzaman, M.H.M. Bhuyan · 2020
2,424 citations
A Comprehensive Review on Lipid Oxidation in Meat and Meat Products
Rubén Domínguez, Mirian Pateiro · 2019
1,481 citations
Abiotic Stress and Reactive Oxygen Species: Generation, Signaling, and Defense Mechanisms
Swati Sachdev, Shamim Akhtar Ansari · 2021
1,291 citations
Regulation of Ascorbate-Glutathione Pathway in Mitigating Oxidative Damage in Plants under Abiotic Stress
Mirza Hasanuzzaman, M. H. M. Borhannuddin Bhuyan · 2019
1,074 citations
Nrf2 and Oxidative Stress: A General Overview of Mechanisms and Implications in Human Disease
Vy Ngo, Martin L. Duennwald · 2022
802 citations