Screening of the profiles of the essential oils from the aerial parts of Nepeta racemosa using classical and microwave-based methods: Comparison with the volatiles using headspace solid-phase micro-extraction
محورهای موضوعی : مجله گیاهان دارویی
1 - گروه شیمی، دانشگاه آزاد واحد شهرکرد، شهرکرد، ایران
کلید واژه: Hydrodistillation, Nepeta racemose, Solvent-free microwave extraction, Microwave assisted hydrodistillation, Headspace solid-phase micro extraction,
چکیده مقاله :
Background & Aim:Nepeta racemosa is an herbal and medicinal plant and this report aims to identify chemical compositions of the essential oils and volatiles of its aerial parts through classical and advanced methods. Experimental: Chemical profiles of the essential oils and volatile compounds from the aerial parts of Nepeta racemosa obtained through hydrodistillation (HD), solvent-free microwave extraction (SFME), microwave assisted hydrodistillation (MAHD) and headspace solid-phase microextraction (HS-SPME) methods were subsequently investigated by means of GC and GC-MS instruments. Results: Totally, 25, 26, 24, and 24 components were identified in the chemical profiles, representing 98.1%, 96.6%, 97.7% and 96.4% of the total compositions when using the HD, HS-SPME, SFME and MAHD methods, respectively. In all samples, oxygenated monoterpenes were the major fractions of the chemical profiles with the exception of chemical composition of the essential oil of N. racemosa obtained by using the MAHD approach in which monoterpene hydrocarbons were dominant constituting compounds. In final, 4aα,7α,7aα-nepetalactone was the most abundant compound in the chemical profiles of HD, HS-SPME and SFME approaches while 4aα,7α,7aβ-nepetalactone oxygenated monoterpene was the most frequent compound in the MAHD profile. Recommended applications/industries: Using the advanced separation methods for isolation of the essential oils are economic, time saving and eminently suited compared with the classical and traditional separation methods. Moreover, the significance of this study relates to the fact that the essential oils, which are rich in monoterpene hydrocarbons and oxygenated monoterpenes could be regarded as powerful food preservatives and novel antioxidants.
زمینه و هدف: گیاه پونه سای البرزی یک گیاه داروئی بوده و این گزارش به شناسائی ساختارهای شیمیائی روغن های اسانسی و اجزاء فرار حاصل از اندام های هوائی این گیاه با استفاده از روش های سنتی و پیشرفته اختصاص دارد. روش تحقیق: پروفایل های شیمیائی روغن های اسانسی و اجزاء فرار حاصل از اندام های هوائی گیاه پونه سای البرزی با استفاده از روش تقطیر با آب، استخراج مایکروویو بدون حلال، تقطیر با آب به کمک مایکروویو و میکرواستخراج فاز جامد فضای فوقانی، در ادامه با دستگاه های کروماتوگراف گازی و کروماتوگراف گازی- طیف سنج جرمی مورد بررسی قرار گرفتند. نتایج و بحث: مجموعاً، 25، 26، 24 و 24 جزء در پروفایلهای شیمیائی شناسائی شدند که به ترتیب 98/1،96/6، 97/7 و 96/4 درصد کل ساختار را در بر می گیرند. در تمامی نمونه ها (به استثناء پروفایل حاصل از روش تقطیر با آب به کمک مایکروویو) بیشترین فراوانی متعلق به مونوترپن های اکسیژن دار بود در حالیکه در ساختار روغن استحصال شده به روش تقطیر با آب به کمک مایکروویو مونوترپن های هیدروکربنه بیشترین درصد را در اختیار داشتند. ترکیب ۴-آ-آلفا، ۷-آلفا، ۷-آ-آلفا، نپتولاکتون فراوان ترین ترکیب در روش های تقطیر با آب، استخراج مایکروویو بدون حلال و میکرواستخراج فاز جامد فضای فوقانی و ترکیب ۴-آ-آلفا، ۷-آلفا، ۷-آ-بتا نپتولاکتون، به عنوان مونوترپن اکسیژن دار وافر در روش تقطیر با آب به کمک مایکروویو، شناسائی شد. توصیه های صنعتی و عملی: استفاده از روش های جداسازی پیشرفته برای استحصال روغن های اسانسی سودمند، مقرون بصرفه زمانی بوده و در مقایسه با روش های سنتی و کلاسیک بمراتب مناسبتر هستند. بعلاوه، اهمیت این مطالعه، ریشه در این حقیقت دارد که روغن های اسانسی سرشار از مونوترپن های اکسیژن دار و مونوترپن های هیدروکربنه می توانند محافظت کننده های قوی فرآورده های غذائی و آنتی اکسیدان هائی بی نظیر باشند.
Abad, M.J., Guerra, J.A., Bermejo, P., Irurzun, A., and Carrasco, L. 2000. Search for antiviral activity in higher plant extracts. Phytotherapy Research. 14: 604-607.
Adams, R.P. 2007. Identification of Essential Oil Components by Gas Chromatography/Mass Spectrometry. Allured Publishing Co., Carol Stream, IL., USA
Adiguzel, A., Ozer, H., Sokmen, M., Gulluce, M., Sokmen, A., Kilic, H., Sahin, F., and Baris, O. 2009. Antimicrobial and antioxidant activity of the essential oil and methanol extract of Nepeta cataria. Polish Journal of Microbiology. 58: 69-76.
Akhlaghi, H., Nekoei, M., Mohammadhosseini, M., and 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. Journal of Essential Oil Bearing Plants. 15: 328-335.
Akhlaghi, H., Shafaghat, A., and Mohammadhosseini, M. 2009. Chemical composition of the essential oil from leaves of Biebersteinia multifida DC. growing wild in Iran. Journal of Essential Oil Bearing Plants. 12: 365-368.
Ali, A., Tabanca, N., Demirci, B., Blythe, E.K., Baser, K.H.C., and Khan, I.A. 2016. Chemical composition and biological activity of essential oils from four Nepeta species and hybrids against Aedes aegypti (L.) (Diptera: Culicidae). Records of Natural Products. 10: 137-147.
Ali, T., Javan, M., Sonboli, A., and Semnanian, S. 2012a. Antinociceptive and anti-inflammatory activities of the essential oil of Nepeta crispa Willd. in experimental rat models. Natural Product Research. 26: 1529-1534.
Ali, T., Javan, M., Sonboli, A., and Semnanian, S. 2012b. Evaluation of the antinociceptive and anti-inflammatory effects of essential oil of Nepeta pogonosperma Jamzad et Assadi in rats. Daru-Journal of Pharmaceutical Sciences. 20.
Aloqail, M., Al-Sheddi, E., Siddiqui, M.A., Musarrat, J., Al-Khedhaity, A., and Farshori, N. 2014. Anticancer activity of sub-fractions of chloroform extracts of Nepeta deflersianaon on human breast and lung cancer cells: An in vitro cytotoxicity assessment. Planta Medica. 80: 1546-1546.
Arthur, C.L., and Pawliszyn, J. 1990. Solid-phase microextraction with thermal desorption using fused-silica optical fibers. Analytical Chemistry. 62: 2145-2148.
Asgarpanah, J., Sarabian, S., and Ziarati, P. 2014. Essential oil of Nepeta genus (Lamiaceae) from Iran: A review. Journal of Essential Oil Research. 26: 1-12.
Baser, K.H.C., Kirimer, N., Kurkcuoglu, M., and Demirci, B. 2000. Essential oils of Nepeta species growing in Turkey. Chemistry of Natural Compounds. 36: 356-359.
Bessada, S.M., Barreira, J.C., and Oliveira, M.B.P. 2015. Asteraceae species with most prominent bioactivity and their potential applications: A review. Industrial Crops and Products. 76: 604-615.
Bhat, J.U., Parray, S.A., Aslam, M., Ansari, S., Nizami, Q., Khanam, R., Siddiqui, A., and Ahmad, M.A. 2012. Anti-seizure activity of flower extracts of Nepeta bractaeta in swiss albino mice. EXCLI Journal. 11: 531-537.
Calmasur, O., Aslan, I., and Sahin, F. 2006. Insecticidal and acaricidal effect of three Lamiaceae plant essential oils against Tetranychus urticae Koch and Bemisia tabaci Genn. Industrial Crops and Products. 23: 140-146.
Dabiri, M., and Sefidkon, F. 2003. Chemical composition of the essential oil of Nepeta racemosa Lam. from Iran. Flavour and Fragrance Journal. 18: 157-158.
Dua, V.K., Verma, G., Agarwal, D.D., Kaiser, M., and Brun, R. 2011. Antiprotozoal activities of traditional medicinal plants from the Garhwal region of North West Himalaya, India. Journal of Ethnopharmacology. 136: 123-128.
Formisano, C., Rigano, D., and Senatore, F. 2011. Chemical constituents and biological activities of Nepeta species. Chemistry & Biodiversity. 8: 1783-1818.
Galati, E.M., Miceli, N., Galluzzo, M., Taviano, M.F., and Tzakou, O. 2004. Neuropharmacological effects of epinepetalactone from Nepeta sibthorpii behavioral and anticonvulsant activity. Pharmaceutical Biology. 42: 391-395.
Hashemi-Moghaddam, H., Mohammadhosseini, M., and 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. Journal of Essential Oil Bearing Plants. 18: 884-893.
Hashemi-Moghaddam, H., Mohammadhosseini, M., and 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. Analytical Methods. 6: 2572-2579.
Hussain, J., Khan, F.-u., Gilani, S.A., Abbas, G., Ahmed, S., Khan, A.-u., Ullah, W., and Choudhary, M.I. 2010. Antiglycation, antiplatelets aggregation, cytotoxic and phytotoxic activities of Nepeta suavis. Latin American Journal of Pharmacy. 29: 573-578.
Hussain, J., Rehman, N.U., Al-Harrasi, A., Khan, A.L., Rizvi, T.S., Mohammad, F.V., Mehjabeen, and Ali, L. 2015. In vivo evaluation of analgesic, anti-inflammatory, and neuropharmacological activities of the chemical constituent from Nepeta clarkei. Archives of Pharmacal Research. 38: 1188-1194.
Iscan, G., Kose, Y.B., Demirci, B., and Baser, K.H.C. 2011. Anticandidal activity of the essential oil of Nepeta transcaucasica Grossh. Chemistry & Biodiversity. 8: 2144-2148.
Jamzad, Z., Grayer, R.J., Kite, G.C., Simmonds, M.S., Ingrouille, M., and Jalili, A. 2003. Leaf surface flavonoids in Iranian species of Nepeta (Lamiaceae) and some related genera. Biochemical Systematics and Ecology. 31: 587-600.
Kobaisy, M., Tellez, M.R., Dayan, F.E., Mamonov, L.K., Mukanova, G.S., Sitpaeva, G.T., and Gemejieva, N.G. 2005. Composition and phytotoxic activity of Nepeta pannonica L. essential oil. Journal of Essential Oil Research. 17: 704-707.
Mohammadhosseini, M. 2015a. 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. 2015b. Chemical composition of the volatile fractions from flowers, leaves and stems of Salvia mirzayanii by HS-SPME-GC-MS. Journal of Essential Oil Bearing Plants. 18: 464-476.
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., and 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. Journal of Essential Oil Bearing Plants. 19: 32-45.
Mohammadhosseini, M., Akbarzadeh, A., Hashemi-Moghaddam, H., Shahnama, M., Fahimi, B., and 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 Journal of Chemistry. 32: 1439-1451.
Mohammadhosseini, M., Akbarzadeh, A., Shafaghat, A., Hashemi-Moghaddam, H., Mohammadi Nafchi, A., and Ashouri, H. 2016c. Chemical composition of the essential oils from flowers and leaves of Marsdenia erecta using microwave assisted hydrodistillation technique. Journal of Essential Oil Bearing Plants: In press.
Mohammadhosseini, M., and Beiranvand, M. 2013. Chemical composition of the essential oil from the aerial parts of Satureja hortensis as a potent medical plant using traditional hydrodistillation. Journal of Chemical Health Risks. 3: 49-60.
Mohammadhosseini, M., Mahdavi, B., and 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. Journal of Essential Oil Bearing Plants. 16: 613-623.
Mohammadhosseini, M., Mahdavi, B., and 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. Journal of Essential Oil Bearing Plants. 18: 1321-1328.
Mohammadhosseini, M., and 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. Journal of Essential Oil Bearing Plants. 17: 747-757.
Mohammadhosseini, M., Pazoki, A., and Akhlaghi, H. 2008. Chemical composition of the essential oils from flowers, stems, and roots of Salvia multicaulis growing wild in Iran. Chemistry of Natural Compounds. 44: 127-128.
Mohammadhosseini, M., Pazoki, A., Zamani, H.A., Akhlaghi, H., and Nekoei, M. 2010. Chemical composition of the essential oil from aerial parts of Senicio gallicus Chaix growing wild in Iran. Journal of Essential Oil Bearing Plants. 13: 704-709.
Mohammadhosseini, M., Zamani, H.A., Akhlaghi, H., and Nekoei, M. 2011. 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. Journal of Essential Oil Bearing Plants. 14: 559-573.
Mozaffarian, V. 1996. A Dictionary of Iranian Plant Names. Farhang Moaser Press, Iran
Nekoei, M., and 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. Analytical Chemistry Letters. 4: 93-103.
Nekoei, M., and Mohammadhosseini, M. 2016a. Chemical composition of essential oils of Salvia leriifolia by three different extraction methods prior to gas chromatographic-mass spectrometric determination: Comparison of HD with SFME and HS-SPME. Journal of Essential Oil Bearing Plants. 19: In press.
Nekoei, M., and Mohammadhosseini, M. 2016b. 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. Journal of Essential Oil Bearing Plants. 19: 59-75.
Pawliszyn, J. 1999. Applications of Solid Phase Microextraction. (Ed.) RSC, Cambridge, UK,
Pawliszyn, J. 2003. Sample preparation: Quo Vadis? Analytical Chemistry. 75: 2543-2558.
Rustaiyan, A., Khosravi, M., Larijany, K., and Masoudi, S. 2000. Compostion of the essential oil of Nepeta racemosa Lam. from Iran. Journal of Essential Oil Research. 12: 151-152.
Safaei-Ghomi, J., Bamoniri, A., Haghani, M., and Batooli, H. 2006. Essential oil composition of Nepeta gloeocephala Rech. f. from Iran. Journal of Essential Oil Research. 18: 635-637.
Safaei-Ghomi, J., Djafari-Bidgoli, Z., and Batooli, H. 2009. Volatile constituents analysis of Nepeta cataria from Central Iran. Chemistry of Natural Compounds. 45: 913-915.
Setkova, L., Risticevic, S., and Pawliszyn, J. 2007. Rapid headspace solid-phase microextraction-gas chromatographic-time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction - I. Method development and optimization. Journal of Chromatography A. 1147: 213-223.
Shafaghat, A., Salimi, F., and Akhlaghi, H. 2008. Chemical composition of the essential oil isolated from flower, leaf, stem and root of Nepeta sintenisii Bornm. from Iran. Journal of Essential Oil Bearing Plants. 11: 391-396.
Sharma, S.K., and Goyal, N. 2011. Biological studies of the plants from genus Pluchea. Annals of Biological Research. 2: 25-34.
Sonboli, A., Gholipour, A., Yousefzadi, M., and Mojarrad, M. 2009. Antibacterial activity and composition of the essential oil of Nepeta menthoides from Iran. Natural Product Communications. 4: 283-286.
Sonboli, A., Salehi, P., and Allahyari, L. 2005. Essential oil composition of Nepeta involucrata from Iran. Chemistry of Natural Compounds. 41: 683-685.
Sonboli, A., Salehi, P., and Yousefzadi, M. 2004. Antimicrobial activity and chemical composition of the essential oil of Nepeta crispa Willd. from Iran. Zeitschrift Fur Naturforschung C-A Journal of Biosciences. 59: 653-656.
Vuckovic, D., Zhang, X., Cudjoe, E., and Pawliszyn, J. 2010. Solid-phase microextraction in bioanalysis: New devices and directions. Journal of Chromatography A. 1217: 4041-4060.
Wu, Q.-X., Shi, Y.-P., and Jia, Z.-J. 2006. Eudesmane sesquiterpenoids from the Asteraceae family. Natural Product Reports. 23: 699-734.
Zargari, A. 1989. Medicinal Plants. University of Tehran Press, Tehran (In Persian).
