CHEMICAL CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF HYDROETHANOLIC CRUDE EXTRACT OF EUGENIA FLORIDA DC (MYRTACEAE) LEAVES

  • Renan G. Bastos aDepartment of Foods and Drugs, Faculty of Pharmaceutical Sciences, Laboratory of Medicinal Plants and Herbal Medicines, Federal University of Alfenas, UNIFAL-MG, Gabriel Monteiro da Silva Street, 700, 37130-000, Alfenas, Minas Gerais, Brazil
  • Carla P. Rosa
  • Josidel C. Oliver
  • Naiara C. Silva
  • Amanda L. T. Dias
  • ClÁudia Q. Da Rocha
  • Wagner Vilegas
  • Geraldo A. Da Silva
  • Marcelo A. Da Silva

Abstract

Objective: The present study aimed to characterize and quantify the total phenolics, flavonoids and tannins in a hydroethanolic crude extract (70% (v/v) (EB)) of the leaves of E. florida DC, as well as to evaluate the antimicrobial activity of the extract against different species of micro-organisms.

Methods: EB was characterized using a mass spectrometer equipped with a direct insertion device for in-stream injection (FIA). Quantitative analyses of major compounds were carried out by spectrophotometry. In addition, we evaluated the sensitivity profiles of different strains of yeast and bacteria against different concentrations of EB.

Results: The classes found were in agreement with those described in the literature: flavonoids, tannins, phenolic acids and saponins. EB showed levels of phenolic compounds, flavonoids and tannins equal to 25.82 mg gallic acid equivalents per gram of extract (EAG/g), 8.42 mg quercetin equivalents per gram of extract (EQ/g) and 7.30 mg tannic acid equivalents per gram of extract (AT/g), respectively. In the analysis of antimicrobial activity, EB was more active against yeasts but was not effective against the bacteria used in the test.

Conclusion: We can conclude that E. florida DC has antimicrobial potential, due to the presence of bioactive secondary metabolites.

Keywords: Phenolics, Micro-organisms, Mass spectrometer, Yeasts, Bacteria, Potential

 

Keywords: Phenolics, Micro-organisms, Mass spectrometer, Yeasts, Bacteria, Potential

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References

1. Madduluri S, Sitaram B, Balasekharan C. In vitro evaluation of anti-inflammatory activity of methanolic and ethanolic leaf extracts of five indigenous plants in South India. Int J PharmTech Res 2014;6:569–74.
2. Firmo WCA, Menezes VJM, Passos CEC, Dias CN, Alves LPL, Dias ICL, et al. Historical context, popular use and scientific conception on medicinal plants. Res Notebooks 2011;18:90–5.
3. Chinni S, Dubala A, Kosaraju J, Khatwal RB, Kumar MNS, Kannan E. Effect of crude extract of Eugenia jambolana Lam. on human cytochrome P450 enzymes. Phytother Res 2014;28:1731–4.
4. Fouladvand M, Barazesh A, Tahmasebi R. Evaluation of in vitro antileishmanial activity of curcumin and its derivatives. Eur Rev Med Pharmacol Sci 2013;17:3306–8.
5. Romagnolo MB, Souza MC. The genus Eugenia L. (Myrtaceae) on the upper paraná river floodplain, mato grosso do sul and paraná states, Brazil. Acta Botanica Brasilica 2006;20:529–48.
6. Donato AM, Morretes BL. Foliar anatomy of Eugenia florida DC. (Myrtaceae). Braz J Pharmacognosy 2009;19:759–70.
7. Stefanello MEA, Pascoal ACRF, Salvador MJ. Essential oils from neotropical Myrtaceae: chemical diversity and biological properties. Chem Biodivers 2011;8:73–94.
8. Hussein SA, Hashem AN, Seliem MA, Lindequist U, Nawwar MA. Polyoxygenated flavonoids from Eugenia edulis. Phytochem 2003;64:883–9.
9. Rattmann YD, Souza LM, Malquevicz-Paiva SM, Dartora N, Sassaki GL, Gorin PA, et al. Analysis of flavonoids from Eugenia uniflora leaves and its protective effect against murine sepsis. J Evidence-Based Complementary Altern Med 2012;1–12. Doi.org/10.1155/2012/623940. [Article in Press]
10. Haminiuk CW, Plata-Oviedo MS, Mattos G, Carpes ST, Branco IG. Extraction and quantification of phenolic acids and flavonols from Eugenia pyriformis using different solvents. J Food Sci Technol 2014;51:2862–6.
11. Yang LL, Lee CY, Yen KY. Induction of apoptosis by hydrolyzable tannins from Eugenia jambos L. on human leukemia cells. Cancer Lett 2000;157:65–75.
12. Omar R, Li L, Yuan T, Seeram NP. -Glucosidase inhibitory hydrolyzable tannins from Eugenia jambolana seeds. J Nat Prod 2012;75:1505–9.
13. Jasmine R, Selvakumar BN, Daisy P. Saponins from Eugenia jambolana with antibacterial activity against beta-lactamase producing methicillin resistant Staphylococcus aureus. J Med Plants Res 2007;1:1–6.
14. Saha S, Subrahmanyam EVS, Chandrashekar K, Shubhash CM, Shashidhara CS. Evaluation of antinociceptive and anti-inflammatory activities of extract and fractions of Eugenia jambolana root bark and isolation of phytoconstituents. Braz J Pharmacognosy 2013;23:651–61.
15. Moraes MM, Camara CAG, Santos ML, Fagg CW. Essential oil composition of Eugenia langsdorffii O. Berg.: relationships between some terpenoids and toxicity against Tetranychus urticae. J Braz Chem Soc 2012;23:1647–56.
16. Singleton VL, Orthofer R, Lamuela-Raventos RM. Analysis of total phenols and other oxidation substrates and antioxidants by means of Folin-Ciocalteau reagent. Methods Enzymol 1999;299:152–78.
17. Kalia K, Sharma K, Singh HP, Singh B. Effects of extraction methods on phenolic contents and antioxidant activity in aerial parts of Potentilla astrosanguinea Lodd. and quantification of its phenolic constituents by RP-HPLC. J Agric Food Chem 2008;56:10129–34.
18. Ferreira FP, Morais SR, Bara MT, Conceição EC, Paula JR, Carvalho TC, et al. Eugenia calycina Cambess extracts and their fractions: their antimicrobial activity and the identification of major polar compounds using electrospray ionization FT-ICR mass spectrometry. J Pharm Biomed Anal 2014;99:89–96.
19. CLSI (Clinical and Laboratory Standards Institute): Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, approved standard; document M7-A6, Wayne, PA, USA; 2003.
20. CLSI (Clinical and Laboratory Standards Institute): Reference method for broth dilution antifungal susceptibility testing of yeasts, approved standard; document M27-S4, Wayne, PA, USA; 2012.
21. Okoh-Esene RU, Thomas SJH, Asuquo S. Proximate and phytochemical analysis of leaf, stem and root of Eugenia uniflora (Surinam or Pitanga cherry). J Nat Prod Plant Resour 2014;1:1–4.
22. Araújo AS, Rocha LL, Tomazela DM, Sawaya AC, Almeida RR, Catharino RR, et al. Electrospray ionization mass spectrometry fingerprinting of beer. Analyst 2005;130:884–9.
23. Bastos DHM, Saldanha LA, Catharino RR, Sawaya ACHF, Cunha IBS, Carvalho PO, et al. Phenolic antioxidants identified by ESI-MS from yerba maté (Ilex paraguariensis) and green tea (Camelia sinensis) extracts. Molecules 2007;12:423–32.
24. La Torre GL, Saitta M, Vilasi F, Pellicanò T, Dugo G. Direct determination of phenolic compounds in Sicilian wines by liquid chromatography with PDA and MS detection. Food Chem 2006;94:640–50.
25. Qiu X, Zhang J, Huang Z, Zhu D, Xu W. Profiling of phenolic constituents in Polygonum multiflorum Thunb. by a combination of ultra-high-pressure liquid chromatography with linear ion trap-Orbitrap mass spectrometry. J Chromatogr A 2013;1292:121–31.
26. Zhu Z, Zhang H, Zhao L, Dong X, Li X, Chai Y, et al. Rapid separation and identification of phenolic and diterpenoid constituents from radix Salvia miltiorrhizae by high-performance liquid chromatography diode-array detection, electrospray ionization time-of-flight mass spectrometry and electrospray ionization quadrupole ion trap mass spectrometry. Rapid Commun Mass Spectrom 2007;21:1855–65.
27. Mullen W, Yokota T, Lean MEJ, Crozier A. Analysis of ellagitannins and conjugates of ellagic acid and quercetin in raspberry fruits by LC-MSn. Phytochemistry 2003;64:617–24.
28. Kato E, Nakagomi R, Gunawan-Puteri MD, Kawabata J. Identification of hydroxychavicol and its dimers, the lipase inhibitors contained in the Indonesian spice, Eugenia polyantha. Food Chem 2013;136:1239–42.
29. Barros L, Dueñas M, Carvalho AM, Ferreira ICFR, Santos-Buelga C. Characterization of phenolic compounds in flowers of wild medicinal plants from Northeastern portugal. Food Chem Toxicol 2012;50:1576–82.
30. Azuma K, Nakayama M, Koshioka M, Ippoushi K, Yamaguchi Y, Kohata K, et al. Phenolic antioxidants from the leaves of Corchorus olitorius L. J Agric Food Chem 1999;47:3963–6.
31. Mishra M, Shukla YN, Kumar S. Euphane triterpenoid and lipid constituents from Butea monosperma. Phytochemistry 2000;54:835–8.
32. Charrouf Z, Hilali M, Jauregui O, Soufiaoui M, Guillaume D. Separation and characterization of phenolic compounds in argan fruit pulp using liquid chromatography-negative electrospray ionization tandem mass spectroscopy. Food Chem 2007;100:1398–401.
33. Mämmelä P. Phenolics in selected European hardwood species by liquid chromatography electrospray ionization mass spectrometry. Analyst 2001;126:1535–8.
34. Engels C, Gräter D, Esquivel P, Jiménez VM, Gänzle MG, Schieber A. Characterization of phenolic compounds in jocote (Spondias purpurea L.) peels by ultra high-performance liquid chromatography/electrospray ionization mass spectrometry. Food Res Int 2012;46:557–62.
35. Bagri P, Ali M, Sultana S, Aeri V. New flavonoids from Punica granatum flowers. Chem Nat Compd 2010;46:201–4.
36. Hori K, Satake T, Saiki Y, Murakami T, Chen C. Chemical and chemotaxonomical studies of filices. LXXVII. Isolation and structure of novel catechin and proanthocyanidins from Dennstaedtia distenta Moore. Chem Pharm Bull 1998;36:4301–6.
37. Cao G, Li Q, Cai H, Tu S, Cai B. Investigation of the chemical changes from crude and processed Paeoniae Radix alba-atractylodis macrocephalae rhizoma herbal pair extracts by using Q exactive high-performance benchtop quadrupole-orbitrap LC-MS/MS. J Evidence-Based Complementary Altern Med 2014:1-14. Doi.org/10.1155/2014/170959. [Article in Press].
38. Poupard P, Sanoner P, Baron A, Renard CM, Guyot S. Characterization of procyanidin B2 oxidation products in an apple juice model solution and confirmation of their presence in apple juice by high-performance liquid chromatography coupled to electrospray ion trap mass spectrometry. J Mass Spectrom 2011;46:1186–97.
39. Santos PML, Schripsema J, Kuster RM. Glycosyl flavonoids from Croton campestris St. Hill. (Euphorbiaceae). Braz J Pharmacognosy 2005;15:321–5.
40. Vieira TR, Barbosa LCA, Maltha CRA, Paula VF, Nascimento EA. Chemical constituents from Melaleuca alternifolia (Myrtaceae). Quím Nova 2004;27:536–9.
41. Sun LR, Qing C, Zhang YL, Jia SY, Li ZR, Pei SJ, et al. Cimicifoetisides A and B, two cytotoxic cycloartane triterpenoid glycosides from the rhizomes of Cimicifuga foetida, inhibit proliferation of cancer cells. Beilstein J Org Chem 2007;3:1–6.
42. Jayasinghe ULB, Wannigama GP, Macleod JK. Glucuronides of Diploclisia glaucescens. J Chem Soc Pak 1998;20:131–7.
43. Jaiswal R, Kuhnert N. Hierarchical scheme for liquid chromatography/multi-stage spectrometric identification of 3,4,5-triacyl chlorogenic acids in green Robusta coffee beans. Rapid Commun Mass Spectrom 2010;24:2283–94.
44. Yoshikawa M, Dai Y, Shimada H, Morikawa T, Matsumura N, Yoshizumi S, et al. Studies on Kochiae fructus. II. On the saponin constituents from the fruit of Chinese Kochia scoparia (Chenopodiaceae): chemical structures of kochianosides I, II, III, and IV. Chem Pharm Bull 1997;45:1052–5.
45. Jayaprakasam B, Nair MG. Cyclooxygenase-2 enzyme inhibitory withanolides from Withania somnifera leaves. Tetrahedron 2003;59:841–9.
46. Hammerstone JF, Lazarus SA, Mitchell AE, Rucker R, Schmitz HH. Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography/ mass spectrometry. J Agric Food Chem 1999;47:490–6.
47. Zhang X, Xiao HB, Xue XY, Sun YG, Liang XM. Simultaneous characterization of isoflavonoids and astragalosides in two Astragalus species by high-performance liquid chromatography coupled with atmospheric pressure chemical ionization tandem mass spectrometry. J Sep Sci 2007;30:2059–69.
48. Liu Z, Li D, Owen NL, Grant DM, Cates RG, Jia Z. Oleanane triterpene saponins from the Chinese medicinal herb Clinopodium chinensis. J Nat Prod 1995;58:1600–4.
49. Zhao J, Yang X, Hattori M. Three new triterpene saponins from the seeds of Aesculus chinensis. Chem Pharm Bull 2001;49:626–8.
50. Madl T, Sterk H, Mittelbach M, Rechberger GN. Tandem mass spectrometric analysis of a complex triterpene saponin mixture of Chenopodium quinoa. J Am Soc Mass Spectrom 2006;17:795–806.
51. Alves TMA, Nagem TJ, Ribeiro A, Mendes NM, Goméz JD, Zani CL, et al. Molluscicidal saponins from Guaiacum officinale (Zygophyllaceae). Int J Pharmacogn 1996;34:81–6.
52. Mimaki Y, Ori K, Kubo S, Sashida Y, Nikaido T, Song L. Scillasaponins A, B, and C, new triterpenoid oligosaccharides from the plants of the subfamily Scilloideae. Chem Lett 2002;21:1863–6.
53. Neri-Numa IA, Carvalho-Silva LB, Morales JP, Malta LG, Muramoto MT, Ferreira JEM, et al. Evaluation of the antioxidant, antiproliferative and antimutagenic potential of araçá-boi fruit (Eugenia stipitata Mc Vaugh–Myrtaceae) of the Brazilian Amazon Forest. Food Res Int 2013;50:70–6.
54. Fang X, Wang J, Hao J, Li X, Guo N. Simultaneous extraction, identification and quantification of phenolic compounds in Eclipta prostrata using microwave-assisted extraction combined with HPLC-DAD-ESI-MS/MS. Food Chem 2015;188:527–36.
55. Kumar S, Pandey AK. Chemistry and biological activities of flavonoids: an overview. Sci World J 2013;1–16. Doi:10.1155/2013/162750. [Article in Press]
56. Wu P, Ma G, Li N, Deng Q, Yin Y, Huang R. Investigation of in vitro and in vivo antioxidant activities of flavonoids rich extract from the berries of Rhodomyrtus tomentosa (Ait.) Hassk. Food Chem 2015;173:194–202.
57. Monteiro JM, Albuquerque UP, Araújo EL, Amorim ELC. Tannins: from chemistry to ecology. Quím Nova 2005;28:892–6.
58. Pereira VP, Knor FJ, Vellosa JCR, Beltrame FL. Determination of phenolic compounds and antioxidant activity of green, black and white teas of Cammelia sinensis (L.) Kuntze, Theaceae. Rev Bras Plantas Med 2014;16:490–8.
59. John KMM, Ayyanar M, Jeeva S, Suresh M, Enkhtaivan G, Kim DH. Metabolic variations, antioxidant potential, and antiviral activity of different extracts of Eugenia singampattiana (an endangered medicinal plant used by Kani tribals, Tamil Nadu, India) leaf. BioMed Res Int 2014:1–11. Doi.org/ 10.1155/2014/726145. [Article in Press]
60. Galeno DML, Carvalho RP, Boleti AP, Lima AS, Almeida PDO, Pacheco CC, et al. Extract from Eugenia punicifolia is an antioxidant and inhibits enzymes related to metabolic syndrome. Appl Biochem Biotechnol 2014;172:311–24.
61. Gobbo-Neto L, Lopes NP. Medicinal plants: factors of influence on the content of secondary metabolites. Quím Nova 2007;30:374–81.
62. Holetz FB, Pessini GL, Sanches NR, Cortez DA, Nakamura CV, Filho BP. Screening of some plants used in the Brazilian folk medicine for the treatment of infectious diseases. Mem Inst Oswaldo Cruz 2002;97:1027–31.
63. Pandey AK, Kumar S. Perspective on plant products as antimicrobials agents: a review. Pharmacologia 2013;4:469–80.
64. Mayer FL, Wilson D, Hube B. Candida albicans pathogenicity mechanisms. Virulence 2013;4:119–28.
65. Kumar TDK, Murali HS, Batra HV. Simultaneous detection of pathogenic B. cereus, S. aureus and L. monocytogenes by multiplex PCR. Indian J Microbiol 2009;49:283–9.
66. Auricchio MT, Bugno A, Barros SBM, Bacchi EM. Antimicrobial and antioxidant activities and toxicity of Eugenia uniflora. Lat Am J Pharm 2007;26:76–81.
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How to Cite
Bastos, R. G., C. P. Rosa, J. C. Oliver, N. C. Silva, A. L. T. Dias, C. Q. D. Rocha, W. Vilegas, G. A. D. Silva, and M. A. D. Silva. “CHEMICAL CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF HYDROETHANOLIC CRUDE EXTRACT OF EUGENIA FLORIDA DC (MYRTACEAE) LEAVES”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 8, no. 6, Apr. 2016, pp. 110-5, https://innovareacademics.in/journals/index.php/ijpps/article/view/10884.
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