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Phytoconstituents Screened of Grapefruit Peels with Antimicrobial Properties of Naringin and Naringenin Extracted and Isolated from its

Bassam A. Hassan1, Fadil Mohsen Hamed 2, Maitham M. Abdulridha3, Farqad M.Baqer4

1, 2, 4

Lecturer at pPharmaceutical Chemistry Department College of Pharmacy, Thi Qar University, Iraq.

3 Lecturer at Technical Institute of Alshatra, Iraq.

Co-author Email:[email protected] : [email protected]

Abstract

Grapefruit belongs to the Rutaceae family of bioactive citrus fruits. The absence of saponins, coumarins, terpenoids, sterols, proteins and anthraquinones was shown by phytochemical scr eening of dried grapefruit peels at the beginning of this research. Alkaloids, flavonoids, sugar s, tannins , glycosides, and polyphenols are present. Naringenin (flavanone) and Naringin (gl ycoside flavanone) were subsequently extracted and isolated from dried grapefruit (citrus frui t) peels.Spectra of FT_iR , thin layer chromotography TLC, point ofmelting

and chemical examination testing its

calculated .Over timee, certain pathogenic bacterial strains isolated from patients such as E.c olii,Acinetobacter, Klebsiellla, Streptococcuus, Staphylococcus, Aeromonas have been studi ed against the antibacterial activity of Naringenin and Naringenin. Naringenin (flavanone) su bsequently demonstrated higher biological activity than the drugs Naringin and Cefuroxime.

Key,words:. Antimicrobial properties ,Naringin,Naringeningrapefruit,, and Phytochemical..Screening.

1.introduction:

Naringenin, a type of flavonoid, is colorless [1] and flavanone is tasteless [2]. It is Identify in a Multiplicityof citrus fruits, orange blossom, tomatoes, and Vegetablesherbs [3] and is the predominant flavanone in grapefruit.

These botanical ingredients have been linked to many biological properties, including anti- inflammatory, antioxidant, antibacterial, antiviral, anti-tumor, anti-lipid, and cardioprotective effect. Most of the knowledge reported was derived in vitro and in vivo studies,fromexperiments ,While There's some psychiatrictrials have also been conducted, the primary focus isf on the vital activity as well as the cardiac protective function of naringin [4].

In addition, similar biological activity between Naringenin (flavanones) and Naringin (flavanone glycosides) were tested in these experiments. Coli Streptococcus, Acinetobacter Klebsiella, Staphylococcus, Aeromonas, some of which are against the pathogenic bacterial strains that have been detected in patients, and have reported highly significant therapeutic properties of Naringin compared to Naringin and cefuroxime, as tabulated in Table No 4.

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Figure No 1 :( I) structure of Naringinand (II) structure of ChemicalNaringenin

2.procedures and Material 2.1.Equipment:

The grapefruit, from the regional supermarket of Nasiriyaah, was picked. They got removed and then brushed washed with distilled water using a washing machine.Then the grapefruit p eel Dried and anchored, it was, properly by using mortar and then to fine pestle by using a seasonal grinder machine For further detailsusing powder.All the chemicals extracted fromthe faculty laboratory are collected. Theresearchdon e at the laboratory of organic chemistry .

2.2. Phytochemical Qualitative Screening

Table No 1. screening of phytochemical (where, – absent and + present) Sr

.No

Structure of Molecules

Chemical testing Testing

Result Outcome

1 Carbohydrates Molish test +ve

2 Flavonoids Shinoda test +ve

3 Alkaloids Wagner reagent + ve

4 Coumarins diluted of NaOH by Filter paper soaked Negative (-ve)

5 Glycosides Fehling’s test +ve

6 Resins Ethanol 95% +boiling + 4% HCl +ve

7 Tannins or Poly phenols

10% of lead acetate +ve

8 Saponin Shaken of the extraction -ve

9 Anthraquinons Borntrager's test -ve

10 Terpenoids Salkowski reaction -ve

11 Sterols Liebermann burchard -ve

12 Protein Ninhydrin test -ve

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2.3 .1 Naringin flavonoid glycoside extraction : Extraction by cold method

50 gm of grapefruit peel material250 ml of petroleum ether,soaked macerated in, two days, te st result. Then purified to extract nonpolar materials, such as resin aromatic oil, fatty acid and waxes etc. via a Buuchner tube defatted process.Then it cooled down and dried.

Extraction by hot method,

The contents were boiling through soxlet for 3 hours with 300 mL in ninety percent alcohol ( 40-

60°C) after fullcold isolation to isolate the polar substances such as glycoside, flavonoids, etc . The filtrate became condensed through the rotary evaporator to a small amount. Acidifying with 20 ml of 6 percent acetic acid (pH 3-4).[12-13] .

2.3.2 Naringenin isolation from Naringin:

Naringinn (2 gram) and methyl alcohol (50 milliliter) and 50% hydrochloric acid (2 millilite

r) were combined, agitated and boiled for 60

min.The resultingg outcomeehomogeneous mixture was concentrated standardizedone to qua rter,and frozen and moved with 15 m of chloroform two times and isolated to the a separator funnel, shake.In order to give the substance Naringenin, the chloroform layer decanted. The following procedure was used to purify naringenin: dissolve with a minimum of acetone, the crude commodityand apply the resulting solution of water(200 milliliter) and ethanoic acid (3 mL) to strongly stirring mix. Precipitated Naringenin was rinsed and chilled in anim mersion blender, to get 1.4 gm with water. The physical characteristics shown in table No3 [1 4].

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.

Figure 2 : Graphical representation of Naringenin and Naringin yield . 3. Outcomes and Discussion :

3.1 Naringenin and Naringin Phytochemistry :

Since Naringenin and Naringin extracted by extraction and separation, from grapefruit peel, a bove that the process was identified chemically verifying the isolated Naringenin and Naringi n by breaking down little quantities of a crystals, with one ml of 95 %ethyl alcohol

dissolved with in testt tube by chemicals such as Molish exam (for generic carbs), Fehling ex am for glycosides With the Molish examination and Fehling's glycoside sample, Naringin sh owed a positiveresult and also showed a +ve Shinoda examitest and an alkalinee flavonone t est. Although Naringenin showed -ve result with Molish and Fehling tests,

glycosidee testing and also +ve Shinoda and alkaline exams were shown. The findings show that naringenin (flavonones) and naringin (glycoside flavonones) were isolated from grapefru its.grapefruit peels were isolated[15] .

TableNo2.Naringenin and Naringin phytochemical screening analysis (where,- absent and + present)

Sr.

No

Name of the Sample

Molish examination

Fehling’s examination

Shinoda examination

Alkaline examination 1 Naringin Positive

ring in Purple

Positive red precipitate

Positive Crimson

Positive Colorless

2 Naringenin negative negative Positive Crimson

Positive Colorless

Graprfruit peel 50 gm Naringin 3.3 gm Naringenin 1.4 gm

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Sr.

No

Parameter Observation Naringin

Observation Naringenin

1 Color Yellowish

brown

colorless

2 Odor The aromatic

str

The aromatic str

3 Point 166 °C 251°C

of Melting

4 Percent Yield 5.80% 2.40%

5 Rf 0.65 0.78

Table No 3:- Physical Characters of Naringin andNaringenin

3.2 Results of Chromatographic Analysis (TLC): Naringin extracted from grapefruit peel e xamined with eluted silica gel, butyl

alcohol: acetic acid : water (4:1:5) Rf = 00.65. Naringenin, eluted with methyl99alcohol chlo roform (9.0: 1.0) Rf = 0.78, was chromatographed over Silica gel. Close to the normal comm ercial Rf value of Naringenin (0.57) and Naringenin (0.68) from publication [16,17,18,19].

3.3 Point of melting:

SMP3I apparatus melting point. A melting Naringin 2540C point, Whereas,, Naringenin 226 0C melting point, which appeared near the literature's melting of Naringin and Naringenin 25 70C, 2210C.

3.4 Spectral analysis by FTIR:

Ft-Irllspectra were registered asCsI disks that used a Shimadzu Ft-IR spectrophotometer, in the range (4000-200) cm-1.

The Ft ir naringin spectrum displays a characteristic band of absorption stretching. 35025cm-1(O-H strr) ,3065cm-1(C-H strr).(aromatic arene , 2924cm1(CH str (alphatic carbon)), 1651 (C = O str), 1604(C=C str. aromatic) [19,20,21.22] as shown in figure No3.

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Figure No 3 Spectra of .FT-IR of Naringenin.

Past data of phytoconstituents, TLC and melting point and FTIR spectra have shown impressi ve results to suggest the extraction and isolation of naringenin (flavonones) and naringin (fla vonones glycoside) from grapefruit peels.

4.Minimum Preparing of solution for inhibit concentration:

It wass achieved by dissolving 0.4 gm in 95 % ethyl alcohol

to get a 40 mg / ml MIC combination of Naringenin and Naringin, which was the minimal in hibitor, the amount checked as seen in the table (No3).

Castration was performed by 0.45 mm and 0.22 mm filtration goods via a Millipore.

5.Biological Action :

In Naringenin and its Naringin's vitro antibacterial activity towards

certain pathogens bacterial isolates from patients. are using agar cups process. The outcomes are summarized in table No3

(Staphylococcus, Aeromonas, Streptococcus,E.coli and klebsiella, Acinetobacter)[23]. Table No 3: Effects of the Naringin and Naringenin effects

CEFUROXIME and in vitro growth of bacteria towards certain patient- isolated pathogenic bacterial strains.

Microbial Types

Diameter inhibition region (mm) Antimicrobial Agent

Naringenin Naringin CEFUROXIME

Streptococcus 30 mm 12 mm 9 mm

Acinetobacter 31 mm 8mm 12 mm

E.coli 29mm 9 mm 2 mm

Klebsiella 21mm 4 mm 7 mm

Staphylococcus 28 mm 10 mm 18 mm

Aeromonas 27 mm 16 mm 11 mm

O

O

O OH O H

OH

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Figure 4: diagrammatic display of the growth of bacteria in vitro between Naringenin, Naring in, and CEFUROXIME towards certain pathogenic bacterial strains isolated from patients.

6.Conclusion :

As discussed earlier, the loss of saponins,coumarins, sterols, terpenoids, anthraquinoness and proteins has been shown by phytochemical screening of drying grapefruit peels. Though flav onoids, alkaloids, carbohydrates, glycosides , tannins and polyphenols are present.Naringenin (flavanone) and Naringin (flavanone glycoside)were consequently isolated and extracted via drying grapefruit pees (citrus fruits) then identified by Ftir spectra, TLC, point of melting,ch emical exam such as Shinoda and alkaline exam as defined in the report.

Naringenin, naringin, and cefuroxime have been screened for certain pathogens.Checked agai nst such Isolated pathogenic bacterial strains from patients such as this oneaas Streptococcus, Acinetobacter, E.colii, Klebsiellaa, Staphylococcuss, Aeromonasss,Naringenin flavanones w ere lastly isolated from grapefruit peels and characterized. The bioactivity study showed that naringenin (flavanones) had a substantial higher bioactivity than naringin and cefuroxime dr ugs, as tabulated in figure 4.

7.Refrences :

[1] inhibitory effect on the human cytochrome P450 isoform [[CYP1A2] resulting in carcinogens of otherwise harmless substances.Fuhr U, Klittich K, Staib AH (April 1993). "Inhibitory effect of grapefruit juice and its bitter principal, naringenin, on CYP1A2 dependent metabolism of caffeine in man". Br J Clin Pharmacol. 35 (4): 431–

6. doi:10.1111/j.1365-2125.1993.tb04162.x.

[2] PMC 1381556. PMID 8485024.Ueng YF, Chang YL, Oda Y, Park SS, Liao JF, Lin MF, Chen CF (1999). "In vitro and in vivo effects of naringin on cytochrome P450- dependent monooxygenase in mouse liver". Life Sci. 65 (24): 2591–

602. doi:10.1016/s0024-3205(99)00528-7. PMID 10619367.

[3] ] Uday Abdul-Reda Hussein, Bassam Abdul Hussein Hasan, Hind Abedallah Salih, Ali Taher Abbas and Sahar Mezher Mtuasher (2017). Antimicrobial Activity Of Ethanolic

0 5 10 15 20 25 30 35 40

Naringenin Naringin CEFUROXIME

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And Aqueous Extracts Of Pomegranate Peel Against Extended Spectrum Beta- Lactamase Producing Bacteria. Journal Of Thi-Qar University., 12(4).

[4] Bahare Salehi 1 , Patrick Valere Tsouh Fokou 2 , Mehdi Sharifi-Rad 3,*, Paolo Zucca 4,*

, Raffaele Pezzani 5,6,* , Natália Martins 7,8,* and Javad Sharifi-Rad 9,10,*(2019)The Therapeutic Potential of Naringenin: A Review of Clinical Trials

Pharmaceuticals 2019, 12, 11; doi:10.3390/ph12010011

www.mdpi.com/journal/pharmaceuticals

[5]Chede PS () Phytochemical analysis of Citrus sinensis peel. Int J Pharm Biol Sci 2013:

4(1): 339-343.

[6] Maitham M Abdulridha, Haider S Abdulhussein, Firas Fadhil Alyaseen and Bassam A Hassan (2019) Phytochemical and antibacterial activity of the pegnum harmalaseeds and its alkaloids. Plant Archives 19(1), 1439-1444.

[7]FADIL M. HAMED1 , SEMMAH. SHALAAL2 , AFRAH T. HLAIL3 AND BASSAM A. HASSAN4 (2019) Phytochemical and Antimicrobial Study of Acetone Extracts of Menthe and Olive Leaves . The Lepidoptera Research Foundation. June ,Volume 50 (2):

51-56

[8] Semma H. Shalaal1 , Afrah T. Halail2 , Fadil M. Hamed 3 and Bassam A. Hassan4 (2019) MACERATION TECHNIQUES EXTRACTION OF THYMUS VULGARIS AND LAUREL (LAURUS NOBILIS) LEAVES WITH ANTIBACTERIAL STUDY . Plant Archives Vol. 19 No. 2, 2019 pp. 4041-4044

[9] Lawal D, Bala JA, Aliyu SY, Huguma MA () Phytochemical screening and in vitro anti- bacterial studies of the ethanolic extract of Citrus sinensis (Linn.) Peel against some clinical bacterial isolates. 2013:Int J Innov Appl Stud 2(2): 138-145.

[10] Suja D, et al. Phytochemical Screening, Antioxidant, Antibacterial Activities of Citrus Limon and Citrus Sinensis Peel Extracts. Int J Pharmacogn Chinese Med 2017, 1(2):

000108.

[12] Hesperidin and hesperitin preparation and purification from Citrus sinensis peels, N.

Lahmer1 N. Belboukhari1*, A. Cheriti2 and K. Sekkoum1, 2015:Der Pharma Chemica, ,7(2):1-4.

[13] Bassam A. Hassan, Fadil Mohsen Hamed, & Firas F. Alyaseen. (2018). Phytochemical screened, characterization and antibacterial activity of hesperetin and hesperidin extracted and isolated from dried oranges peels. International Journal of Research in Pharmaceutical Sciences, 9(4), 1362-1367. Retrieved from https://pharmascope.org/ijrps/article/view/477

[14] Bassam A Hassan, Hameedi N Nasera and Maitham M Abdulridha (2019) Synthesis and antimicrobial evaluation of fused heterocyclic compound [1,2,4] triazolo [4,3-b][1,2,4,5]

tetra zine. Int. J. Research in Pharmaceut. Sci. 10(2), 1254-1258.

https://doi.org/10.26452/ijrps.v10i2.417.

[15] Bassam A.Hasan, Maitham M.Abdulridha (2014) PREPARATION AND CHARACTERISATION OF SOMETRANSATION METAL COMPLEXES OF NEW [BUTANAL (5-ETHYL-1, 3, 4-OXADIAZOL-2-YL) HYDRAZONE]

[16] Bassam A.Hasan, Maitham M.Abdulridha (2014) PREPARATION AND CHARACTERISATION OF SOMETRANSATION METAL COMPLEXES OF NEW

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[BUTANAL (5-ETHYL-1, 3, 4-OXADIAZOL-2-YL) HYDRAZONE] The Swedish Journal of Scientific Research (sjsr), Volume 1. Issue 5. October 2014

[17] Najim Abbas Jabir Al Awwadi, Bassam Abdulhussein Hasan Alsafee1 and Maitham Mohamed Abdulridha (2016) Synthesis And Characterization Of Cu(II) And Fe(II) Metal Complexes of Oxazepine Derivative Via Schiff Base [Fe(HPOHBOT)Cl2 ] And [Cu(HPOHBOT)Cl2 ]. Afr. J. Pharm. Pharmacol. 10, 728-736.

[18] Firas F Alyaseen, Bassam A Hassan and Haider S Abdulhussein (2018. Extraction, isolation and chemical identification of piperine alkaloid from black pepper seeds and its antibacterial activity. Plant Archives 18(2), 2171-2176.

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