Gas chromatography mass spectrum and Fourier transform - infrared spectroscopy analysis of methanolic extract of Cressa cretica L.

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1 Available online at WSN 49(2) (2016) EISSN Gas chromatography mass spectrum and Fourier transform - infrared spectroscopy analysis of methanolic extract of Cressa cretica L. leaves Aseel Muhammed Omran, Nidaa Adnan Abu-seraj, Ibtihal Muiz Al Husaini Department of Biology, Babylon University, Hilla, Iraq address: biomaster2007@yahoo.com ABSTRACT Aims of this study were to investigation the presence of phytochemical compounds in the methanolic extract of Cressa cretica L. leaves by using GC-MS method and report the functional groups by using FT-IR spectroscopy. The identification of phytochemical compounds based on the peak area, retention time, molecular weight, molecular formula, MS fragment ions. Thirty four phytochemical compounds were identification in the methanolic extract of Cressa cretica leaves. The GC-MS analysis provide the existence of 5-Methyl-6-phenyltetrahydro-1,3-oxazine-2-thione, Lactose, 3-Deoxy-L-ribose-2,5-dibenzoate, Sarreroside, Pterin-6-carboxylic acid, Octadecadiynoic acid, methyl ester, d-mannose, Dodecanoic acid, 3-hydroxy-, Geranyl isovalerate, Tetradecanoic acid, 6-epishyobunol, Paromomycin, Cis-9-Hexadecenoic acid, and others. The FT-IR analysis revealed the presence of Alkenes, aliphatic amines, nitro compounds, alkanes. These are chemical compounds are may be useful for various herbal formulation as antifungal, antibacterial, anti- inflammatory, antioxidant and others. Keywords: FT-IR; GC-MS analysis; Leaves; Methanol; Cressa cretica

2 1. INTRODUCTION Herbal medicines had usually used for treatment of diseases and for helth mentinance [1], plant based drugs have been used since immemorial time, which interesting with herbal products lead to grouth of medicinal plant industries [2]. Cressa cretica L. (convolvulaceae) is a small, dwarf shrub [3], roots are horizontal, geminate with lateral branches leading upward to produce above- ground parts. The leaf blade is 1-2 mm long, lanculate, ovate or elliptic to scale like. Flowers are solitary, white or pink axillary, 5-8 mm long [4]. Seeds are 3-4 mm long, glabrous, smooth and shining to reticulate, with dark, brown color [5]. Cressa cretica showed variation in productivity in response to environmental factors. Net productivity and aboveground biomass were higher during the brief winter in comparison to summer [6]. C. cretica used in all parts as a paste and decoction to treated fungus infection, asthma, blood purifier and eczema [7]. Aqueous and alcoholic extracts of leaves of this plant have a very good activity against some microbial pathogens such as gram positive, gram negative bacteria and some fungi species, such as Candida albicans, Aspergillus niger, and Penicillium chrysogenum [8]. The plant can be used as anti-tubercular, expectorant [9]. Ethanolic extract of C. cretica significantly reduced blood glucose, serum cholesterol in rats [4]. This plant also used to synthesis silver nanoparticles from silver nitrate using C. cretica leaf extract [10]. In the last few years gas chromatography mass spectrometry has become firmly established as a key technology plat form for phytochemical profiling in plant [11-13]. Gas chromatography provides a very adequate technique for the separation of complex samples because this technique give a combination of speed, sensitivity and a high resolving power [14]. Fourier transform infrared spectrometry is a physico-chemical analytical technique and one of the most widely used methods to identify the structure of unknown composition or its functional group, and the intensity of the absorption spectra associated with molecular composition or content of the chemical group [15]. The present study involves an assessment using GC-MS and FT-IR spectroscopic techniques to investigate and determine the bioactive compounds in the leaves of C. cretica. 2. MATERIALS AND METHODS Collection and preparation of plant material The leaves were purchased from the gardens of Babylone University, Hilla city, after had cleaned and removal foreign materials, the leaves were washed twice with running tap water and once with distilled water and dried under shade for ten days at room temperature. Dried leaves stored in airtight container to avoid the effect of humidity and then stored at room temperature until further use. Preparation of sample about 20 gm of the plant sample powdered were soaked in 100 ml methanol for 16 h in a rotatory shaker. What man No.1 filter paper was used to separate the extract of plant. The supernatant were used for further phytochemical analysis [16]. It was again filtered through sodium sulphate in order to remove the traces of moisture

3 Gas chromatography mass spectrum analysis The GC-MS analysis of the plant extract was made in a (QP 2010 Plus SHIMADZU) instrument under computer control at 70 ev [17-19]. About 1 μl of the methanol extract was injected into the GC-MS using a micro syringe, then the scanning was done for 45 min. As the compounds were separated, and removed from the column and entered a detector which was capable of creating an electronic signal whenever a compound was detected. The greater concentration in the sample, bigger was the signal obtained which then processed by the computer. The time from when the injection was made (Initial time) to when elution occurred is referred to as the Retention time (RT). While the instrument was run, the computer generated a graph from the signal called chromatogram. Each of the peaks in the chromatogram represented the signal created when a compound eluted from the Gas chromatography column into the detector. The x-axis showed the RT and the y-axis measured the intensity of the signal to quantify the component in the sample injected. As individual compounds removed from the Gas chromatographic column, they entered the electron ionization (mass spectroscopy) detector, where they were bombarded with a stream of electrons causing them to break apart into fragments. The fragments obtained were actually charged ions with a certain mass. The M/Z (Mass/Charge) ratio obtained was calibrated from the graph obtained, which was called the Mass spectrum graph which is the fingerprint of a molecule. Before analyzing the extract using gas chromatography and mass spectroscopy, the temperature of the oven and the flow rate of the gas used and electron gun were programmed initially. The temperature of the oven was maintained at 100 C. Helium gas was used as a carrier as well as an eluent. The flow rate of helium was set to 1ml per minute. The electron gun of mass detector liberated electrons having energy of about 70eV. The column employed here for the separation siloxane). The identity of the components in the extracts was assigned by the comparison of their retention indices and mass spectra fragmentation patterns with those stored on the computer library and also with published literatures [19,20]. Fourier transform infrared spectrophotometer (FTIR) The powdered sample of the plant specimen was treated for FTIR spectroscopy (Shimadzu, IR Affinity 1, Japan). The sample was run at infrared region between 400 and 4000 nm [21,22]. 3. RESULTS AND DISCUSSION Gas Chromatography and Mass spectroscopy analysis of compounds was carried out in methanolic extract of C. cretica leaves, shown in Table 1.and the components corresponding to the peaks were determined as follows: 5-Methyl-6-phenyltetrahydro-1,3-oxazine-2-thione; Eicosanoic acid, phenylmethyl ester; Lactose ; 3-Deoxy-L-ribose-2,5-dibenzoate; Adenosine, 4'-methylaminoformyl-4'-deshydroxymethyl-N-[3-is; Benzenemethanol, 4-hydroxy-α-[1- (methylamino) ethyl]; Benzenemethanol, 2-(2-aminopropoxy)-3-methyl-; Sarreroside; Pterin- 6-carboxylic acid; 12,15-Octadecadiynoic acid, methyl ester; d-mannose; Dodecanoic acid, 3-hydroxy-; Cyclopenta[1,3] cyclopropa[1,2]cyclohepten-3(3ah)-one, 1,2; Desulphosinigrin; -383-

4 Geranyl isovalerate; Cyclopentanemethylamine, 2-isopropylidene-N,N,5-trimethyl-; Tetradecanoic acid; Ppropiolic acid, 3-(1-hydroxy-2-isopropyl-5-methylcyclohexyl); Acetamide, N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2butynyl]; 6-epi-shyobunol; 2,7- Diphenyl-1,6-dioxopyridazino[4,5:2',3']pyrrolo[4',5'-d]pyrid; 3,7,11,15-Tetramethyl-2- hexadecan-1-ol; Paromomycin; Cis-9-Hexadecenoic acid; γ-linolenic acid, methyl ester; Estra-1,3,5(10)-trien-17β-ol; Ethyl iso-allocholate; 7,10-Octadecadienoic acid, methyl ester; Cholestan-3-ol,2-methylene-,(3β,5α)-; Octadecanoic acid; Strychane, 1-acetyl-20α-hydroxy- 16-methylene-; 8,8'-Trimethoxy -3 -piperidyl-2,2'-binaphthalene-1,1',4,4'-tetra; Spirost-8-en- 11-one,3-hydroxy-,(3β,5α,14β,20β,22β,25R)-; Campesterol (Figer 1-34). Fourier- transform infrared analysis of methanolic extract of cressa cretica leaves proved the presence of Alkenes, aliphatic amines, nitro compounds, amines, alkanes, (Table 2; Figer 35). Among the identified phytocompounds have the property of antioxidant and antimicrobial activities [23,24]. Plant based antimicrobials have enormous therapeutic potential as they can serve the purpose with lesser side effects. Continued further exploration of plant derived antimicrobials is needed today. [25] and [5] investigate the activity of alcoholic extract of cressa cretica as anti fungul. Chaudhary reported that the ethanolic extract of C. cretica was significantly reduced blood glucose and this extract have a high anti diabetic potential. Figure 1. 5Methyl-6phenyltetrahydro1,3oxazine Figure 2. Eicosanoic acid, phenylmethyl -2-thione in the leaf extract of C. cretica L. ester in the leaf extract of C. cretica L

5 Figure 3. Lactose in the leaf extract Figure 4. 3-Deoxy-L-ribose-2,5-dibenzoate in of C. cretica L. the leaf extract of C. cretica L. Figure 5. Adenosine, 4'-methylaminoformy l-4'-deshydroxymethyl-n-[3-is in the leaf extract of C. cretica L. Figure 6. Benzenemethanol,4-hydroxy-α- -[1-(methylamino)ethyl]-,(R* in the leaf extract of Cressa cretica L -385-

6 Figure 7. Benzenemethanol, 2-(2-aminopropoxy) Figure 8. Sarreroside in the leaf 3-methyl- in the leaf extract of Cressa cretica L. extract of Cressa cretica L. Figure 9. Pterin-6-carboxylic acid in Figure ,15-Octadecadiynoic acid, methyl the leaf extract of C. cretica L. ester in the leaf extract of C. cretica L

7 Figure 11. d-mannose in the leaf extract of C. cretica L. Figure 12. Dodecanoic acid, 3-hydroxy in the leaf extract of C.a cretic Figure 13. Cyclopenta[1,3]cyclopropa[1,2 Figure 14. Desulphosinigrin in the cyclohepten-3(3ah)-one,1,2 in the leaf leaf extract of C. cretica L. extract of C. cretica L

8 Figure 15. Geranyl isovalerat in the leaf of C. cretica L. Figure 16. Cyclopentanemethylamine. 2-isopropylidene- N,N,5-trimethyl-, in the leaf of C.cretica L Figure 17. Tetradecanoic acid in the leaf extract of C. cretica L. Figure 18. Ppropiolic acid,3-(1-hydroxy-2- isopropyl 5-methylcyclohexyl)- in the leaf extract of C. cretica L

9 Figure 19. Acetamide, N-methyl-N-[4- Figure epi-shyobunol in the (3-hydroxypyrrolidinyl)-2-butynyl]- in leaf extract of C. cretica L. the leaf extract of C. critica L. Figure 21. 2,7-Diphenyl-1,6-dioxopyridazino Figure 22. 3,7,11,15Tetramethyl-2hexadecan- [4,5:2',3']pyrrolo[4',5'-d]pyrid in the leaf 1-ol in the leaf extract of C. cretica L. extract of C. cretica L

10 Figure 23. Paromomycin in the leaf Figure 24. Cis-9-Hexadecenoic acid extract of C. cretica L. in the leaf extract of C. cretica L. Figure 25. γ-linolenic acid, methyl ester in Figure 26. Estra-1,3,5(10)-trien-17β-ol the leaf extract of C. cretica L. in the leaf extract of C. cretica L

11 Figure 27. Ethyl iso-allocholate in the leaf Figure 28. 7,10-Octadecadienoic acid, methyl extract of C. cretica L. ester in the leaf extract of C. cretica L. Figure 29. Cholestan-3-ol,2-methylene-,(3β,5α)- Figure 30. Octadecanoic acid in the in the leaf extract of C.cretica L. leaf extract of C. cretica L

12 Figure 31. Strychane, 1-acetyl-20α-hydroxy-16 -methylene- in the leaf extract of C. cretica L. Figure 32. 3',8,8'-Trimethoxy-3-piperidyl-2 2'-binaphthalene-1,1',4,4'-tetra, in the leaf extract of C. cretica L. Figure 33. Spirost-8-en-11-one,3-hydroxy-, Figure 34. Campesterol in the leaf (3β,5α,14β,20β,22β,25R)- in the leaf extract extract of C. cretica L. of C. cretica L

13 4. 3-Deoxy-L-ribose- 2,5-dibenzoate ,77,92,105,122,13 6,165, Lactose ,73,85,91,97,126,145,16 3,191 Preservative [26] 2. Eicosanoic acid, phenylmethyl ester ,71,91,108,126,1 47,167,207, Methyl-6- phenyltetrahydro-1,3- oxazine-2-thione ,77,91,97, 117,132,147, 174,207 Serial No. Phytochemical compound RT (min) Molecular Weight Exact Mass MS Fragment- ions Pharmacolog-ical actions World Scientific News 49(2) (2016) Table 1. Major phytochemical compounds identified in methanolic extract of Cressa ctretica Linn Leaves. Chemical structure -393-

14 9. Pterin-6-carboxylic acid ,69,93,105,122,149,1 63,177,207 Anti-psychotic, moodstabilizer and antiparasite [21] 8. Sarreroside ,74,113,191,229,271,35 4,401, Benzenemethanol, 2-(2- aminopropoxy)-3-methyl ,65,77,91,105,121,135,1 52,178,195 Anti-nociceptive effect. [21] 6. Benzenemethanol,4-hydroxy- α-[1-(methylamino)ethyl]-,(r* ,65,77,95,121,147, Adenosine, 4'- methylaminoformyl-4'- deshydroxymethyl-n- [3-is ,76,85,97,120,148,16 3,206,240,282 World Scientific News 49(2) (2016)

15 15 Geranyl isovalerate ,69,85,93,103,12 1,129,136,154,168, 183,198,219 antifungal activity [28] 14 Desulphosinigrin ,73,85,103,127,145,163,2 13,262 anticancer activity [27] 13 Cyclopenta[1,3]cyc lopropa[1,2]cycloh epten-3(3ah)-one,1, ,69,78,91,105,11 9,133,147,162,190 Anti - pain effect. [21] 12 Dodecanoic acid, 3-hydroxy ,69,83,96,112,12 3,138,151,180, d-mannose ,73,103,149 Anti-allergic and anti-bacterial [22] ,15- Octadecadiynoic acid, methyl ester ,67,74,79,91,119,133,147,161,178,2 05,220 World Scientific News 49(2) (2016)

16 20 6-epi-shyobunol ,67,81,93,109,121,136,161,207, Acetamide, N-methyl- N-[4-(3- hydroxypyrrolidinyl)-2- butynyl] ,68,124,137,167, Ppropiolic acid, 3-(1- hydroxy-2-isopropyl-5- methylcyclohexyl) ,69,81,95,109,121,13 5,150,163,178,191, Tetradecanoic acid ,60,73,83,97,115,129, 143,157,171,185,199,21 1,228 Antioxidant, cancer preventive,nematicide,hy pocholesterolemic, lubricant [27 ] 16 Cyclopentanemethylamine, 2-isopropylidene-N,N,5- trimethyl-, ,79,107,136,164 World Scientific News 49(2) (2016)

17 25 γ-linolenic acid, methyl ester ,67,79,93,107,12 1,135,150,163,175, 194,207,235,260 Antihistaminic, Anticoronary, Insectifuge,Antieczemic, [29] 24 Cis-9-Hexadecenoic acid ,69,83,97,111,123, 137,192,236,254 Flavoring agent, Anti- oxidant. [24] 23 Paromomycin ,67,80,94,109,124,145, 227,252,277,303 Anti-bacterial Agents. [22] 22 3,7,11,15- Tetramethyl-2- hexadecan-1-ol ,71,81,95,109,123, 137,151,179,278 Antimicrobial antiinflammatory [29] 21 2,7-Diphenyl-1,6- dioxopyridazino[4,5:2',3']pyrrolo[4', 5'-d]pyrid ,65,77,93,105,119,149,165,187,21 1,224,238,267,281,327,355 Anti- angiogenic effect and antitumor efficacy [22] World Scientific News 49(2) (2016)

18 30 Octadecanoic acid ,73,83,97,115,129,143,157, 171,185,199,227,241,255,284 Cancer preventive Insectifuge [32] 29 Cholestan-3-ol,2- methylene-,(3β,5α) ,81,95,105,121,133,16 1,175,203, ,10-Octadecadienoic acid, methyl ester ,67,81,95,109,121,1 50,164,205,220,234,26 3, Ethyl iso-allocholate ,69,81,95,253,367,400,418 Antimicrobial Diuretic Antiinflammatory Antiasthma [30;31] 26 Estra-1,3,5(10)-trien- 17β-ol ,73,85,97,107,129, 157,185,213,241,256 Anti- arrhythmic activities [22] World Scientific News 49(2) (2016)

19 34 Campesterol ,81,145,161,213,255, 289,315,382, Spirost-8-en-11-one,3- hydroxy-,(3β,5α,14β,20β,22β,25r) ,69,95,135,187,207,229, 281,299,314,356,395,428 Estrogenic, progesterogenic and antiinflammatory effects [21] 32 3',8,8'-Trimethoxy-3-piperidyl-2,2'- binaphthalene-1,1',4,4'-tetra ,71,112,149,167,223,279,313,328 Anticancer, antiarthritic and antiinflammatory [22] 31 Strychane, 1-acetyl-20α-hydroxy-16- methylene ,70,88,130,166,239,281,338 World Scientific News 49(2) (2016)

20 Medium C N Stretch aliphatic amines Medium C N Stretch aliphatic amines Medium C N Stretch aliphatic amines Medium C N Stretch aliphatic amines Strong =C H Bending Alkenes Strong =C H Bending Alkenes Strong =C H Bending Alkenes Peak (Wave Number cm-ˡ) Intensity Corr. Intensity Base (H) Base (L) Area Corr. Area Type of Intensity Bond Type of Vibration Functional group assignment Group frequency World Scientific News 49(2) (2016) Table 2. FT-IR peak values of solid analysis of methanolic extract of Cressa cretica l. No

21 Medium C-H Stretch alkanes Medium C-H Stretch alkanes Medium N H Bending amines Medium N O Symmetric stretch nitro compounds World Scientific News 49(2) (2016) CONCLUSION Cressa cretica Linn. is a native plant of Iraq. Thus the GC-MS analysis of methanolic extract of leaves of this plant showed a highly complex profile containing approximately thirty four components. It contain phytochemicals which may be useful for various herbal formulation as anti-inflamatory, anti-bacterial, anti-fungal and others. References [1] Sahito, S.R.;Memon, M.A., Kazi, T.G. and Gazi, G.H. Evaluation of mineral Contents in medicinal plant Azadirachta indica (neem). J. Chem. Soc. Pak. 25(2): , [2] Barnes, J., Anderson, L.A. and Philipson, J.D. Herbal Medicines. A guide for Healthcare Professionals, thirded. Pharmaceutical Press, London, [3] Rani, S., Chaudhary, S., Singh, P., Mishra, G., Jha, K.K., and Khosa, R.L. Cressa cretica Linn: An Important Medecinal Plant- A Review on Its Traditional Uses, Phytochemical and Pharmacological Properties. J. Nat. Prod. Plant Resour., 1(1): , [4] Chaudhary, S., Khosa, R.L., Jha, K.K. and Verma, N. Evaluation of Activity of Cressa cretica Linn in Alloxan Induced Diabetes in Rats. Pharmacology online 3: ,

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Gas chromatography mass spectrum and fouriertransform infrared spectroscopy analysis of methanolic extract of Rosmarinus oficinalis leaves

Gas chromatography mass spectrum and fouriertransform infrared spectroscopy analysis of methanolic extract of Rosmarinus oficinalis leaves Vol. 7(6), pp. 90-106, June 2015 DOI: 10.5897/JPP2015.0348 Article Number: C17730553452 ISSN 2141-2502 Copyright 2015 Author(s) retain the copyright of this article http://www.academicjournals.org/jpp