Chemical composition of the essential oils from the aerial parts of Malva neglecta Wallr. from Khorramabad, Lorestan Province, Iran using solvent free microwave extraction (SFME) method
الموضوعات :
Majid Mohammadhosseini
1
(Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood, Iran)
الکلمات المفتاحية: Essential oil, Hinokione, Malva neglecta Wallr, Non-terpene hydrocarbon, Solvent free microwave extraction (SFME),
ملخص المقالة :
This study deals with the investigation of the efficacy of solvent free microwave extraction (SFME) method to extract the essential oils from the aerial parts of Malva neglecta Wallr.. The essential oils were then injected onto an HP-5MS column of a commercially available GC/MS (Hewlett-Packard 5973), which resulted in a chromatogram consisting of 24 compounds accounting for 99.9% of the oil composition. In terms of general categories, non-terpene hydrocarbons and sesquiterpene hydrocarbons were found to be the major fractions of the chemical profiles. Moreover, hinokione was recognized as the most abundant constituent component of the essential oil comprising 40.7% of the total oil structure. Regarding our findings in this study, the SFME can be introduced as a rapid, cost-effective, and environmentally friendly extraction method for the separation of the essential oils.
Afolayan, A.J., Aboyade, O.M., Adedapo, A.A., Sofidiya, M.O., 2010. Anti-inflammatory and analgesic activity of the methanol extract of Malva parviflora Linn (Malvaceae) in rats. Afr .J. Biotechnol. 9, 1225-1229.
Akhlaghi, H., Asl, M.R.S., Mohammadhosseini, M., 2009a. Composition of the essential oil of Hymnocrater platystegius in Iran. Chem. Nat. Comp. 45, 448-449.
Akhlaghi, H., Nekoei, M., Mohammadhosseini, M., Motavalizadehkakhky, A., 2012. Chemical composition of the volatile oils from the flowers, stems and leaves of Prangos latiloba Korov. using the head space solid phase microextraction method prior to analysis by gas chromatography-mass spectrometry. J. Essent. Oil-Bear. Plants 15, 328-335.
Akhlaghi, H., Shafaghat, A., Mohammadhosseini, M., 2009b. Chemical composition of the essential oil from leaves of Biebersteinia multifida DC. growing wild in Iran. J. Essent. Oil-Bear. Plants 12, 365-368.
Akhlaghi, H., Shafaghat, A., Salimi, F., Mohammadhosseini, M., 2011. GC/MS analysis of the essential oil from wild Stachys pubescens Ten. leaves from Northwest Iran. Anal. Chem. Lett. 1, 325-327.
Alves, P.M., Guedes Queiroz, L.M., Pereira, J.V., Vieira Pereira, M.d.S., 2009. In vitro antimicrobial, antiadherent and antifungal activity of Brazilian medicinal plants on oral biofilm microorganisms and strains of the genus Candida. Rev. Soc. Bras. Med. Trop. 42, 222-224.
Andrade Pinto, J.M., Souza, E.A., Oliveira, D.F., 2010. Use of plant extracts in the control of common bean anthracnose. Crop Prot. 29, 838-842.
Benso, B., Rosalen, P.L., Alencar, S.M., Murata, R.M., 2015. Malva sylvestris inhibits inflammatory response in oral human cells. An in vitro infection model. Plos One 10, e0140331.
Bernardo, W.L.d.C., Boriollo, M.F.G., Gonçalves, R.B., Höfling, J.F., 2005. Staphylococcus aureus ampicillin-resistant from the odontological clinic environment. Rev. Inst. Med. Trop. Sao Paulo 47, 19-24.
Bouriche, H., Meziti, H., Senator, A., 2010. In vivo anti-inflammatory and antioxidant effects of Malva parviflora leaf extracts, in: Safwat, M.S.A., Tantawy, A., Moaty, E.A. (Eds.), XIII International Conference on Medicinal and Aromatic Plants, pp. 23-30.
Bouriche, H., Meziti, H., Senator, A., Arnhold, J., 2011. Anti-inflammatory, free radical-scavenging, and metal-chelating activities of Malva parviflora. Pharm. Biol. 49, 942-946.
Chemat, F., Cravotto, G., 2013. Microwave-Assisted Extraction for Bioactive Compounds, Theory and Practice. Springer, New York.
Cogo, L.L., Bastos Monteiro, C.L., Miguel, M.D., Miguel, O.G., Cunico, M.M., Ribeiro, M.L., de Camargo, E.R., Botao Kussen, G.M., Nogueira, K.d.S., Dalla Costa, L.M., 2010. Anti-Helicobacter pylori activity of plant extracts traditionally used for the treatment of gastrointestinal disorders. Braz. J. Microbiol. 41, 304-309.
Conforti, F., Ioele, G., Statti, G.A., Marrelli, M., Ragno, G., Menichini, F., 2008. Antiproliferative activity against human tumor cell lines and toxicity test on Mediterranean dietary plants. Food Chem. Toxicol. 46, 3325-3332.
Dalar, A., Turker, M., Konczak, I., 2012. Antioxidant capacity and phenolic constituents of Malva neglecta Wallr. and Plantago lanceolata L. from Eastern Anatolia region of Turkey. J. Herb. Med. 2, 42-51.
Daniela, A., Pichichero, E., Canuti, L., Cicconi, R., Karou, D., D'Arcangelo, G., Canini, A., 2007. Identification of phenolic compounds from medicinal and melliferous plants and their cytotoxic activity in cancer cells. Caryologia 60, 90-95.
de Souza, G.C., Haas, A.P.S., von Poser, G.L., Schapoval, E.E.S., Elisabetsky, E., 2004. Ethnopharmacological studies of antimicrobial remedies in the south of Brazil. J. Ethnopharmacol. 90, 135-143.
DellaGreca, M., Cutillo, F., D'Abrosca, B., Fiorentino, A., Pacifico, S., Zarrelli, A., 2009. Antioxidant and radical scavenging properties of of Malva sylvestris. Nat. Prod. Commun. 4, 893-896.
Duke, J.A., Atchley, A.A., 1986. CRC Handbook of Proximate Analysis Tables of Higher Plants. CRC Press.
Esteves, P.F., Sato, A., Esquibel, M.A., de Campos-Buzzi, F., Meira, A.V., Cechinel-Filho, V., 2009. Antinociceptive activity of Malva sylvestris L. Lat. Am. J. Pharm. 28, 454-456.
Facciola, S., 1990. Cornucopia: A Source Book of Edible Plants. Kampong Publications, 1870 Sunrise Drive, Vista, CA 92084, USA.
Franzotti, E.M., Santos, C.V.F., Rodrigues, H., Mourao, R.H.V., Andrade, M.R., Antoniolli, A.R., 2000. Anti-inflammatory, analgesic activity and acute toxicity of Sida cordifolia L. (Malva-branca). J. Ethnopharmacol. 72, 273-278.
Ghanati, F., Khatami, F., 2011. Polyphenols and their antioxidant activity in callus-cultured Malva neglecta cells under UV-B and UV-C irradiation. Planta Med. 77, 1286-1286.
Grierson, D.S., Afolayan, A.J., 1999. Antibacterial activity of some indigenous plants used for the treatment of wounds in the Eastern Cape, South Africa. J. Ethnopharmacol. 66, 103-106.
Guder, A., Korkmaz, H., 2012. Evaluation of in-vitro antioxidant properties of hydroalcoholic solution extracts Urtica dioica L., Malva neglecta Wallr. and their mixture. Iran. J. Pharm. Res. 11, 913-923.
Hashemi-Moghaddam, H., Mohammadhosseini, M., Basiri, M., 2015. Optimization of microwave assisted hydrodistillation on chemical compositions of the essential oils from the aerial parts of Thymus pubescens and comparison with conventional hydrodistllation. J. Essent. Oil-Bear. Plants 18, 884-893.
Hashemi-Moghaddam, H., Mohammadhosseini, M., Salar, M., 2014. Chemical composition of the essential oils from the hulls of Pistacia vera L. by using magnetic nanoparticle-assisted microwave (MW) distillation: Comparison with routine MW and conventional hydrodistillation. Anal. Methods 6, 2572-2579.
Huang, C.Y., Zeng, L.F., He, T., Wang, C.J., Hong, J.R., Zhang, X.Q., Hou, Y.H., Peng, S.S., 1998. In vivo and in vitro studies on the antitumor activities of MCP (Malva crispa L. powder). Biomed. Environ. Sci. 11, 297-306.
Keles, O., Ak, S., Bakirel, T., Alpinar, K., 2001. Screening of some Turkish plants for antibacterial activity. Turk. J. Vet. Anim. Sci. 25, 559-565.
Khan, H., Jan, S.A., Javed, M., Shaheen, R., Khan, Z., Ahmad, A., Safi, S.Z., Imran, M., 2016. Nutritional composition, antioxidant and antimicrobial activities of selected wild edible plants. J. Food Biochem. 40, 61-70.
Kumarasamy, Y., Cox, P.J., Jaspars, M., Nahar, L., Sarker, S.D., 2002. Screening seeds of Scottish plants for antibacterial activity. J. Ethnopharmacol. 83, 73-77.
Lucchesi, M.E., Chemat, F., Smadja, J., 2004a. An original solvent free microwave extraction of essential oils from spices. Flav. Fragr. J. 19, 134-138.
Lucchesi, M.E., Chemat, F., Smadja, J., 2004b. Solvent-free microwave extraction of essential oil from aromatic herbs: comparison with conventional hydro-distillation. J. Chromatogr. A 1043, 323-327.
Ma, C.-h., Yang, L., Zu, Y.-g., Liu, T.-t., 2012. Optimization of conditions of solvent-free microwave extraction and study on antioxidant capacity of essential oil from Schisandra chinensis (Turcz.) Baill. Food Chem. 134, 2532-2539.
Mavi, A., Terzi, Z., Ozgen, U., Yildirim, A., Coskun, M., 2004. Antioxidant properties of some medicinal plants: Prangos ferulacea (Apiaceae), Sedum sempervivoides (Crassulaceae), Malva neglecta (Malvaceae), Cruciata taurica (Rubiaceae), Rosa pimpinellifolia (Rosaceae), Galium verum subsp verum (Rubiaceae), Urtica dioica (Urticaceae). Biol. Pharm. Bull. 27, 702-705.
Mohammadhosseini, M., 2012a. Chemical profile and antibacterial activity in hydrodistilled oil from aerial parts of Prangos ferulacea (L.) Lindl. and prediction of gas chromatographic retention indices by using genetic algorithm multiple linear regressions. Asian J. Chem. 24, 3814-3820.
Mohammadhosseini, M., 2012b. Hydrodistilled volatile oils of the flowers of Salvia leriifolia Bench. and Salvia multicaulis Vahl. as two growing wild plants in Iran. Asian J. Chem. 24, 1432-1434.
Mohammadhosseini, M., 2013. Hydrodistilled volatile oil from stems of Eryngium creticum Lam. in the marginal brackish regions of Semnan province by using gas chromatography combined with mass spectrometry. Asian J. Chem. 25, 390-392.
Mohammadhosseini, M., 2015. Chemical composition of the essential oils and volatile fractions from flowers, stems and roots of Salvia multicaulis Vahl. by using MAHD, SFME and HS-SPME methods. Journal of Essential Oil Bearing Plants 18, 1360-1371.
Mohammadhosseini, M., 2016. A Comprehensive Review on New Methods for Processing, Separation and Identification of the Essential Oils. Islamic Azad University of Shahrood Press, Shahrood, Iran.
Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., Mohammadi Nafchi, A., Mashayekhi, H.A., Aryanpour, A., 2016a. Chemical composition of the essential oils from the aerial parts of Artemisia sieberi by using conventional hydrodistillation and microwave assisted hydrodistillation: A comparative study. J. Essent. Oil-Bear. Plants 19, 32-45.
Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., Shahnama, M., Fahimi, B., Azami, S., 2016b. Gas chromatographic-mass spectrometric analysis of volatiles obtained by HS-SPME-GC-MS technique from aerial parts of Ziziphora Capitata L., and evaluation for biological activity. Oriental J. Chem. 32(3), 1439-1451.
Mohammadhosseini, M., Beiranvand, M., 2013. Chemical composition of the essential oil from the aerial parts of Satureja hortensis as a potent medical plant using traditional hydrodistillation. J. Chem. Health Risks 3, 49-60.
Mohammadhosseini, M., Mahdavi, B., Akhlaghi, H., 2013. Characterization and chemical composition of the volatile oils from aerial parts of Eryngium bungei Bioss. (Apiaceae) by using traditional hydrodistillation, microwave assisted hydrodistillation and head space solid phase microextraction methods prior to GC and GC/MS analyses: A comparative approach. J. Essent. Oil-Bear. Plants 16, 613-623.
Mohammadhosseini, M., Mahdavi, B., Shahnama, M., 2015. Chemical composition of essential oils from aerial parts of Ferula gummosa (Apiaceae) in Jajarm Region, Iran using traditional hydrodistillation and solvent-free microwave extraction methods: A comparative approach. J. Essent. Oil-Bear. Plants 18, 1321-1328.
Mohammadhosseini, M., Nekoei, M., 2014. Chemical compositions of the essential oils and volatile compounds from the aerial parts of Ferula ovina using hydrodistillation, MAHD, SFME and HS-SPME methods. J. Essent. Oil-Bear. Plants 17, 747-757.
Mohammadhosseini, M., Nekoei, M., Mashayekhi, H.A., Aboli, J., 2012. Chemical composition of the essential oil from flowers, leaves and stems of Haplophyllum perforatum by using head space solid phase microextraction. J. Essent. Oil-Bear. Plants 15, 506-515.
Mohammadhosseini, M., Pazoki, A., Akhlaghi, H., 2008. Chemical composition of the essential oils from flowers, stems, and roots of Salvia multicaulis growing wild in Iran. Chem. Nat. Comp. 44, 127-128.
Mohammadhosseini, M., Pazoki, A., Zamani, H.A., Akhlaghi, H., 2011a. Chemical composition of the essential oil from aerial parts of Ajuga chamaecistus Ging. subsp Scopria in brackish regions of Iran. J. Essent. Oil-Bear. Plants 14, 101-105.
Mohammadhosseini, M., Pazoki, A., Zamani, H.A., Akhlaghi, H., Nekoei, M., 2010. Chemical composition of the essential oil from aerial parts of Senicio gallicus Chaix growing wild in Iran. J. Essent. Oil-Bear. Plants 13, 704-709.
Mohammadhosseini, M., Zamani, H.A., Akhlaghi, H., Nekoei, M., 2011b. Hydrodistilled volatile oil constituents of the aerial parts of Prangos serpentinica (Rech.f., Aell. Esfand.) Hernnstadt and Heyn from Iran and quantitative structure-retention relationship simulation. J. Essent. Oil-Bear. Plants 14, 559-573.
Motavalizadehkakhky, A.R., Shafaghat, A., Zamani, H.A., Akhlaghi, H., Mohammadhosseini, M., Mehrzad, J., Ebrahimi, Z., 2013. Compositions and the in vitro antimicrobial activities of the essential oils and extracts of two Achillea species from Iran. J. Med. Plants Res. 7, 1280-1292.
Mozaffarian, V., 1996. A Dictionary of Iranian Plant Names. Farhang Moaser Press, Iran.
Nekoei, M., Mohammadhosseini, M., 2014. Application of HS-SPME, SDME and cold-press coupled to GC/MS to analysis the essential oils of Citrus sinensis CV. Thomson Navel and QSRR study for prediction of retention indices by stepwise and genetic algorithm-multiple linear regression approaches. Anal. Chem. Lett. 4, 93-103.
Nekoei, M., Mohammadhosseini, M., 2016. Chemical compositions of the essential oils from the aerial parts of Achillea wilhelmsii using traditional hydrodistillation, microwave assisted hydrodistillation and solvent-free microwave extraction methods: Comparison with the volatile compounds obtained by headspace solid-phase microextraction. J. Essent. Oil-Bear. Plants 19, 59-75.
Nekoei, M., Mohammadhosseini, M., Akhlaghi, H., 2012. Chemical composition of the volatile oils from the aerial parts of Artemisia annua L. (Asteraceae) by using head space solid phase microextraction and hydrodistillation methods prior to gas chromatographic-mass spectrometric determination: A comparative investigation. J. Essent. Oil-Bear. Plants 15, 926-933.
Oshchepkova, Y.I., Rogozhin, E.A., Sultanova, E.M., Oripova, M.Z., Veshkurova, O.N., Egorov, T.A., Salikhov, S.I., 2012. Cationic peptides and proteins from seeds of plants of the family Malvaceae. Chem. Nat. Comp. 48, 288-290.
Peterson, R.T., McKinney, M., 1968. A Field Guide to Wildflowers of Northeast and North Central North America. Houghton Mifflin Co., Boston, USA.
Rahimi, M., Karimi, E., Nekoei, M., Mohammadhosseini, M., 2016. Hydro-distilled volatile oil constituents from the aerial parts of Satureja mutica and QSRR simulation by multiple linear regression. J. Essent. Oil-Bear. Plants 19, 307-320.
Razavi, S.M., Zarrini, G., Molavi, G., Ghasemi, G., 2011. Bioactivity of Malva sylvestris L., a medicinal plant from Iran. Iran J. Basic Med. Sci. 14, 574-579.
Romitelli, I., Martins, M.B.G., 2013. Comparison of leaf morphology and anatomy among Malva sylvestris ("gerânio-aromático"), Pelargonium graveolens ("falsa-malva") and Pelargonium odoratissimum ("gerânio-de-cheiro"). Rev. Bras. Plantas Med. 15, 91-97.
Seyyednejad, S.M., Koochak, H., Darabpour, E., Motamedi, H., 2010. A survey on Hibiscus rosa-sinensis, Alcea rosea L. and Malva neglecta Wallr as antibacterial agents. Asian Pac. J. Trop. Med. 3, 351-355.
Shahnama, M., Azami, S., Mohammadhosseini, M., 2015. Characterization of the essential oil and evaluation of antibacterial activity of methanolic extract of Stachys lavandulifolia Vahl. Int. J. Curr. Microbiol. App. Sci 4, 275-283.
Shale, T.L., Stirk, W.A., van Staden, J., 2004. Effect of storage on antibacterial and COX-1 anti-inflammatory activity of three plants used as traditional medicines in Lesotho. South Afr. J. Bot. 70, 602-610.
Shale, T.L., Stirk, W.A., van Staden, J., 2005. Variation in antibacterial and anti-inflammatory activity of different growth forms of Malva parviflora and evidence for synergism of the anti-inflammatory compounds. J. Ethnopharmacol. 96, 325-330.
Sleiman, N.H., Daher, C.F., 2009. Malva sylvestris water extract: A potential anti-inflammatory and anti-ulcerogenic remedy. Planta Med. 75, PH10.
Stef, D.S., Gergen, I., Trasca, T.I., Harmanescu, M., Lavinia, S., Ramona, B., Heghedus, M.G., 2009. Total antioxidant and radical scavenging capacities for different medicinal herbs. Rom. Biotech. Lett. 14, 4704-4709.
Tesevic, V., Vajs, V., Lekic, S., Dordevic, I., Novakovic, M., Vujisic, L., Todosijevic, M., 2012. Lipid composition and antioxidant activities of the seed oil from three Malvaceae species. Arch. Biol. Sci. 64, 221-227.
Tomoda, M., Gonda, R., Shimizu, N., Yamada, H., 1989. Plant mucilages .42. An anti-complementary mucilage from the leaves of Malva-sylvestris var Mauritiana. Chem. Pharm. Bull. 37, 3029-3032.
Turker, M., Dalar, A., 2013. In vitro antioxidant and enzyme inhibitory properties and phenolic composition of M. neglecta Wallr. (Malvaceae) fruit: A traditional medicinal fruit from Eastern Anatolia. Ind. Crops Prod. 51, 376-380.
Usami, A., Kashima, Y., Marumoto, S., Miyazawa, M., 2013. Characterization of aroma-active compounds in dry flower of Malva sylvestris L. by GC-MS-O analysis and OAV calculations. J. Oleo Sci. 62, 563-570.
Vitullo, M., Ripabelli, G., Fanelli, I., Tamburro, M., Delfine, S., Sammarco, M.L., 2011. Microbiological and toxicological quality of dried herbs. Lett. Appl. Microbiol. 52, 573-580.
Walter, C., Shinwari, Z.K., Afzal, I., Malik, R.N., 2011. Antibacterial activity in herbal products used in Pakistan. Pakistan J. Bot. 43, 155-162.
Wang, X., Bunkers, G.J., 2000. Potent heterologous antifungal proteins from cheeseweed (Malva parviflora). Biochem. Biophys. Res. Commun. 279, 669-673.
Wang, X., Bunkers, G.J., Walters, M.R., Thoma, R.S., 2001. Purification and characterization of three antifungal proteins from cheeseweed (Malva parviflora). Biochem. Biophys. Res. Commun. 282, 1224-1228.
Zargari, A., 1989. Medicinal Plants. University of Tehran Press, Tehran (In Persian).
