بررسی تنوع فیتوشیمیایی اسانس گیاه دارویی Perilla frutescens L. var. crispa در مناطق مختلف کشت

محورهای موضوعی : گیاهان دارویی

نجمه عباسی ¹ (گروه علوم باغبانی و زراعی، واحد علوم و تحقیقات، دانشگاه آزاد اسلامی، تهران، ایران)
محمد حسین میرجلیلی ² (گروه کشاورزی، پژوهشکده گیاهان و مواد اولیه دارویی، دانشگاه شهیدبهشتی تهران، ایران)
راهله ابراهیمی ³ (گروه علوم باغبانی و زراعی، واحد علوم و تحقیقات، دانشگاه آزاد اسلامی، تهران، ایران)
حسنعلی نقدی بادی ⁴ (گروه زراعت و اصلاح نباتات، دانشکده کشاورزی، دانشگاه شاهد، تهران، ایران)
امیر صحرارو ⁵ (گروه علوم باغبانی دانشگاه گیلان)

تاریخ دریافت : 1400/11/18 تاریخ پذیرش : 1401/01/18 تاریخ انتشار : 1402/01/01

کلید واژه: اقلیم, مونوترپن, تغییرات محیطی, کاریوفیلن, Perilla frutescens, سزکوئی‏ترپن,

چکیده مقاله :

گیاه Perilla frutescens var. crispa دارویی و معطر از تیره نعناعیان است که امروزه مصارف متعددی از جمله رفع یبوست، درمان آسم، ضدپیری، مراقبت از پوست و طعم دهنده دارد. با توجه به تاثیر شرایط اقلیمی محل رویش بر مقدار مواد موثره گیاهان دارویی، در این مطالعه، تغییر در محتوی و ترکیبات شیمیایی اسانس گیاه کشت‌شده در مزارع تحقیقاتی چهار منطقه از کشور (رشت، نور، خرم‌آباد و نیشابور) در سال 1399 ارزیابی شد. اندام هوایی گیاه در مرحله رویشی جمع آوری و اسانس آن به روش تقطیر با آب بدست آمد. اندازه گیری کمّی و کیفی ترکیبات شیمیایی اسانس با استفاده از گازکروماتوگرافی و گازکروماتوگرافی متصل به طیف سنج جرمی انجام شد. در بین مناطق مورد مطالعه نیشابور و رشت به‌ترتیب از بیشترین و کمترین ارتفاع از سطح دریا و از نظر طبقه بندی اقلیمی نیز، دو منطقه رشت و نور دارای تشابه بیشتری بودند. محتوای اسانس به‌ترتیب 1/45، 1/33، 1/26 و 1/16 درصد وزنی به وزنی برای گیاهان کشت‌شده در رشت، نور، نیشابور و خرم آباد بدست آمد. همچنین درمجموع 28، 27، 25 و 27 ترکیب به ترتیب در اسانس گیاهان کشت شده در مناطق نور، رشت، خرم آباد و نیشابور شناسایی شدند. (ای)-کاریوفیلن (4/7-42/58 درصد)، آلفا-کادینول (2/5-8/16 درصد)، (ای)-نرولیدول (8/5-3/9 درصد)، آلفا- دهیدرو-الشولتزیا کتون (1/5-2/7 درصد)، سیس- دی هیدرو- آلفا- ترپینیل استات (0/5-1/7 درصد) و اِگوما کتون (2/5-0/5 درصد) ترکیبات غالب در اسانس گیاه کشت‌شده در مناطق مختلف بودند. سزکوئی ترپن‌های هیدروکربنه (61/2-44/9 درصد) بخش غالب نمونه‌های اسانس را به خود اختصاص دادند. آنالیز کلاستر بر اساس ترکیبات شیمیایی اسانس، مناطق موردمطالعه را در دو زیرخوشه گروه بندی کرد، به‌طوری‌که مناطق نور و رشت در یک زیرگروه و مناطق خرم‌آباد و نیشابور در گروه دیگر قرار گرفتند. نتایج نشان داد، مناطق با اقلیم معتدل برای بهبود کمّیت اسانس و مناطق خشک و نیمه‌خشک در افزایش کیفیت اسانس گیاه مناسب هستند.

چکیده انگلیسی:

Perilla frutescens var. crispa, a medicinal and aromatic plant belonging to the Lamiaceae family is widely used for the treatment of constipation, asthma, and skin disorders, and also as spice. As climatic, environmental, and edaphological conditions of the plant habitats affect active substances of medicinal plants, quantitative and qualitative changes in the essential oil content and composition of the plants cultivated in the Research Farms of four regions of Iran (Rasht, Noor, Khorramabad, and Neishabour) were evaluated in the present study in 2020. Aerial organs of the plants were collected at the vegetative stage and their essential oils were isolated by hydro-distillation. The essential oils were quantitatively and qualitatively analyzed by gas chromatography (GC) and GC-mass spectrometry (GC-MS). Among the studied areas, the highest and lowest altitudes were Neishabour and Rasht, respectively. The climatic classification of Rasht and Noor was also more similar. The essential oil contents (%w/w) of the plant samples in Rasht, Noor, Neishabour, and Khorramabad were 1.45, 1.33, 1.26, and 1.16, respectively. In total, 28, 27, 25, and 27 compounds were identified in Noor, Rasht, Khorramabad, and Neishabour regions, respectively. (E)-Caryophyllene (42.4-58.7%), α-cadinol (8.2-16.5%), (E)-nerolidol (3.8-9.5%), α-dehydro-elsholtzia ketone (2.1-7.5%), cis-dihydro-α-terpinyl acetate (1.0-7.5%), and egoma ketone (0.2-5.5%) were the major essential oil compounds at different regions. Sesquiterpene hydrocarbons (44.9-61.2%) were the major class of the compounds of essential oils. Cluster analysis based on the essential oil compositions classified the studied areas into two distinct groups. Noor and Rasht were clustered in one group and Khorramabad and Neishabour were clustered in the other group. Results showed that temperate regions are suitable to increase the essential oil contents of the plants, while arid and semi-arid regions can improve the quality of essential oils.

منابع و مأخذ:

Abu-Darwish, M.S., Abu Dieyeh, Z.H., Mufeed, B., Al- Tawaha, A.R.M. and Al-dalain, S.Y.A. 2009. Trace element contents and essential oil yields from wild Thyme plant (Thymus serpyllum L.) grown at different natural variable environments, Jordan. Journal of Food, Agriculture and Environment, 7(3-4): 920-924.

Ahmed, H.M. 2018. Ethnomedicinal, phytochemical and pharmacological investigations of Perilla frutescens (L.) Britt. Molecules. 24, 102.

Ahmed, H.M. and Tavaszi-Sarosi, S. 2019. Identification and quantification of essential oil content and composition, total polyphenols and antioxidant capacity of Perilla frutescens (L.) Britt. Food Chemistry, 275: 730–738.

Anjula Pandey, A. and Bhatt, C. 2008. Diversity distribution and collection of genetic resources of cultivated and weedy type in Perilla frutescens (L.) Britton var. frutescens and their uses in Indian Himalaya. Genetic Resources and Crop Evolution, 55: 883–892.

Arianfar, M., Akbarinodehi, D., Hemati, K. and Rostampoor, M. 2018. Effects of altitude and aspect on efficiency of producing essence and phytochemical properties of Artemisia aucheri Boiss. and Artemisia sieberi Besser in South Khorasan rangelands. Rangeland, 12(3): 281-294. (In Persian)

Asif, M. 2012. Chemical and nutritional characterization of Perilla frutescens seed oil. The Libyan Journal of Pharmacy and Clinical Pharmacology, 1:623012

Azarnivand, H., Ghavam Araban, M., Sefidkon, F. and Tavili, A. 2010. The effect of ecological characteristics on quality and quantity of the essential oils of Achillea millefolium L. subsp. Millefolium. Iranian Journal of Medicinal and Aromatic Plants, 25(4): 556-571. (In Persian)

Baharmast, Z., Kheiry, A., Sanikhani, M. and Soleimani, A. 2021. Study and comparison of morphological and phytochemical traits of Mentha pulegium L. in different habitats of Guilan province. Eco-phytochemical Journal of Medicinal Plants, 8(2): 60-75. (In Persian)

Baser, K.H.C., Demirci, B. and Dönmez, A.A. 2003. John Wiley & Sons, Ltd. Composition of the essential oil of Perilla frutescens (L.) Britton from Turkey. Flavour and Fragrance Journal,18: 122–123.

Chang, X.L., Zhao, Z.L., Li, X.L., Xu, H., Sun, Y. and Wang, W.H. 2014. Extraction and advanced adsorbents for the separation of perillaldehyde from Perilla frutescens (L.) Britton var. crispa F. viridis leaves. Food Science and Technology Research, 20: 189–199.

Chauhan, N.K., Singh, S., Haider, S.Z., Lohani, H. and Kushwaha, B.L. 2013. Compositional variability in volatiles from different plant organs of Perilla frutescens L. cultivated in Uttarakhand (India). Journal of Pharmacy Research, 6: 361-363.

Chen, Z., Wu, K., Zhu, W., Wang, Y., Su, C., Yi, F., 2022. Chemical compositions and bioactivities of essential oil from P erilla leaf (Perillae folium) obtained by ultrasonic-assisted hydro-distillation with natural deep eutectic solvents. Food Chemistry, 375, art. no. 131834.

Consonni, R., Cagliani, L.R., Docimo, T., Romane, A. and Paola Ferrazzi, P. 2013. Perilla frutescens (L.) Britton: honeybee forage and preliminary results on the metabolic profiling by NMR spectroscopy, Natural Product Research, 27(19):1743-1748.

Dimita, R., Min Allah, S., Luvisi, A., Greco, D., De Bellis, L., Accogli, R., Mininni, C., Negro, C. 2022. Volatile compounds and total phenolic content of Perilla frutescens at microgreens and mature stages. Horticulturae, 8 (1), art. no. 71.

Duan, S., Li, Z., Fan, Z., Qin, M., Yu, X., Li, L. 2022. Effects of dietary addition of Perilla frutescens seeds on the content of polyunsaturated fatty acids in egg yolk of Gallus domesticus. Pakistan Journal of Zoology, 54 (1), pp. 161-166.

Evergetis, E., Michaelakis, A., Papachristos, D.P., Badieritakis, E., Kapsaski-Kanelli, V.N. and Haroutounian, S.A. 2016. Seasonal variation and bioactivity of the essential oils of two Juniperus species against Aedes (Stegomyia) albopictus (Skuse, 1894). Journal of Parasitology Research, 115: 2175-2183.

Ghanbari, M., Souri, M., Omidbaigi, R. and Hadavand Mirzaei, H. (2014). Evaluation of some ecological factors, morphological traits and essential oil productivity of Achillea millefolium L. Iranian Journal of Medicinal and Aromatic Plants, 30(5): 692-701. (In Persian)

Ghane, M., Pirdashti, H., Ghajar Sepanlou, M. and Babaeizad, V. 2018. Evaluation of morphological, yield and medicinal properties of Perilla (Perilla Frutscens) under soil fertility treatments in Mashhad Ardehal and Sensen regions of Kashan. Journal of Plant Production, 25(2): 99-117. (In Persian)

Gobbo-Neto, L., Guaratini, T., Pessoa, C., de Moraes, M., Costa-Lotufo, L., Vieira, R.F., Colepicolo, P. and Lopes, N.P. 2010. Differential metabolic and biological profiles of Lychnophora ericoides from different localities in Brazilian Campos rupestres. Journal of the Brazilian Chemical Society, 21(4): 750-759.

Gorgini Shabankare, H., Asgharipour, M.R. and Fakheri, B. 2015. Morpho-chemical Diversity among Iranian Teucrium polium L. (Lamiaceae) populations in Fars province. Journal of Agricultural Science and Technology, 17 (3) :705-716.

Habibi, H., Mazaheri, D., Majnoun Hosseini, N., Chaeichi, M., Fakhr Tabatabaei, M. and Bigdeli, M. 2007. Effect of altitude on essential oil and components in wild Thyme (Thymus kotschyanus Boiss) Taleghan region. Pajouhesh-Va-Sazandegi (In Agronomy and Horticulture), 19(4): 2-10. (In Persian)

Heydari, A., Hadian, J., Esmaeili, H., Kanani, M.R., Mirjalili, M.H. and Sarkhosh A. 2019. Introduction of Thymus daenensis into cultivation: Analysis of agro-morphological, phytochemical and genetic diversity of cultivated clones. IndustrialCropsand Products, 131, 14-24.

Inan, M., Kirpik, M., Alpaslan, D., Kaya, A. and Kirici, S. 2011. Effect of harvest time on essential oil composition of T. spicata L. growing in flora of Adıyaman. Advances in Environmental Biology, 5(2): 356-358.

Jamshidi, A.M., Aminzadeh, M., Azarnivand, H. and Abedi, M. 2006. Effect of evaluation for quality and quantity of essential oil Thymus kotschyanus (Damavand - Tar). Journal of Medicinal Plants, (5)18: 17-22. (In Persian)

Jin-hua, Zh., Er-hua, R., Ping-yi, G., Xin, W., Yin-yuan, W. and Xiang-yang, Y. 2012. The interacting effect of urea and quizalofop-ethyl herbicide on improving growth and controlling weeds in Perilla frutescens L. Journal of Medicinal Plants Research, 6: 1055-1064.

Kang, H.-B., Kim, S.-H., Uhm, S.-H., Kim, D.-K., Lee, N.-S., Jeong, Y.-G., Sung, N.-Y., Kim, D.-S., Han, I.-J. and Yoo, Y.-C. 2022. Perilla frutescens leaf extract attenuates vascular dementia-associated memory deficits, neuronal damages, and microglial activation. Molecular Biology, 44, 257–272.

Kang, N.S. and Lee, J.H. 2011. Characterization of phenolic phytochemicals and quality changes related to the harvest times from the leaves of Korean purple Perilla (Perilla frutescens). Food Chemistry, 124: 556-562.

Kiazolu, J.B., Intisar, A., Zhang, L., Wang, Y., Zhang, R. and Wu, Z. 2016. Phytochemical screening and chemical variability in volatile oils of aerial parts of Morinda morindoides. Natural Product Research, 30: 2249- 2252.

Lee, J., Kim, D-S., Cho, J., Hong, S.J., Pan, J.H., Kim, J.K. and Shin, E-Ch. 2019. Perilla frutescens Britton: A comprehensive study on flavor/taste and chemical properties during the roasting process. Molecules. 24, 1374.

Lee, J.H., Park, K.H., Lee, M.H., Kim, H.T., Seo, W.D., Kim, J.Y., Baek, I., Jang, D.S. and Ha, T.J. 2013. Identification, characterization, and quantification of phenolic compounds in the antioxidant activity-containing fraction from the seeds of Korean Perilla (Perilla frutescens) cultivars. Food Chemistry, 136: 843–852.

Li, B. and Kim, M. 2021. Cultivation of Perilla frutescens (Lamiaceae) in prehistoric Korea. Journal of archaeological science: Reports Volume 40, Part B, 103224.

Lin, K.-H., Jhou, Y.-J., Wu, C.-W., Chang, Y.-S. 2020. Growth, physiological, and antioxidant characteristics in green and red Perilla frutescens varieties as affected by temperature-and water-stressed conditions. Scientia Horticulturae, 274, 109682.

Lotfi, K., Oraei, M., Hazrati, S., Faramarzi, A. and Ajali, J. 2021. Investigation of morphophysiological diversity of different populations of Stachys lavandulifolia based on multivariate statistical methods. Journal of Crop Breeding, 13(39): 195-207.

Lu, X., Hao, L., Wang, F., Huang, Ch. and Wu, SH. 2013. Molecular cloning and overexpression of the tyrosine aminotransferase (TAT) gene leads to increased Rosmarinic acid yield in Perilla frutescens L. Plant Cell, Tissue and Organ Culture, 115: 69-83.

Meng, L., Lozano, Y.F., Gaydou, E.M. and Li, B. 2009. Antioxidant activities of polyphenols extracted from Perilla frutescens varieties. Molecules. 14:133-140.

Mohammadi Soleimani, S. 2010. The effect of some environmental factors on the composition of essential oil of Teucrium chamaedrys. Master Thesis in Range Management. Tarbiat Modares University Noor. (In Persian)

Mohammadian, A., Karamian, R., Mirza, M. and Sepahvand, A. 2014. Effects of altitude and soil characteristics on essential of Thymus fallax Fisch.et C.A. Mey. in different habitats of Lorestan province. Iranian Journal of Medicinal and Aromatic Plants, 30(4): 519-528. (In Persian)

Najjarfirozjaee, M., Hemmati, K., Khorasaninejhad, S., Daraei Garmakhany, A. and Bagherifard, A. 2014. Effect of altitude on morphological and biochemical characteristics of Nettle (Urtica dioica L.) Plant in mazandaran and golestan provinces. Journal of Plant Environmental Physiology, 9(3): 1-11. (In Persian)

Negi, V.S., Rawat, L.S., Phondani, P.C. and Chandra, A. 2011. Perilla frutescens in Transition: a medicinal and oil yielding plant need instant conservation, a case study from Central Himalaya, India. Environment & We an International Journal of Science & Technology, 6: 193-200.

Nina, C., Tatiana, S., Camelia, S., Veaceslav, G., Radu, N. and Valentin, G. 2014. Biological and phytochemical research on Perilla frutescens Var. purpuracens (Hayata). In republic of Moldova. Buletinul Academiei de Ştiinţe a Moldovei, Ştiinţele vieţii, 2: 323.

Nitta, M., Lee, J.K. and Ohnishi, O. 2003. Asian Perilla crops and their weedy forms: their cultivation, utilization and genetic relationships. Economic Botany, 57: 245-253.

Omidbaigi, R. 2007. Approaches to the production and processing of medicinal plants, Volume I, Behnashr Publication, 283 pages. (In Persian)

Rafati, A., Valizadeh, N., Sefidkon, F., Imani, Y. and Noormand Moayyed F. 2021. Variability in the quantity and quality of the essential oil of Nepeta crassifolia in natural habitats and agronomical conditions of East Azerbaijan Province. Iranian Journal of Medicinal and Aromatic Plants, 10.22092/IJMAPR.2021.354805.3002. (In Persian)

Rasti, A. 2002. Study of the effect of habitat on Aras plant species in Amarloo Rudbar region and identification and comparative study of its essential oil compounds at different altitudes and slope directions. Master Thesis, Urmia University. (In Persian).

Razazi, N., Ashraf Jafari, A., Khodarahmpour, Z. and Sadat, Sh. 2021. Phytochemical comparison of essential oils in five species of Stachys L. in Khorramabad agronomic conditions. Eco-phytochemical Journal of Medicinal Plants, 9(3): 1-15. (In Persian)

Rezaei, M., Jaymand, K. and Moalemi, M. 2002. Study on chemical constituents of Valeriana sisymbriifolia vahl of essential oils from three different locallities. Iranian Journal of Medicinal and Aromatic Plants, 18: 123-135. (In Persian)

Rouphael, Y., Raimondi, G., Paduano, A., Sacchi, R., Barbieri, G. and De Pascale, S. 2015. Influence of organic and conventional farming on seed yield, fatty acid composition and tocopherols of Perilla. Amer. Journal of the Chemical Society, 9(4): 303-308.

Ruberto, G., Barrata, M.T., Sari, M. and Kaˆabeche, M. 2002. Chemical composition and antioxidant activity of essential oils from Algerian Origanum glandulosum Desf. Flavour and Fragrance Journal, 17: 251-254.

Saeb, K. and Gholamrezaee, S. 2012. Variation of essential oil composition of Melissa officinalis L. leaves during different stages of plant growth. Asian Pacific Journal of Tropical Biomedicine, 2(z2): s547-s549.

Safaei, L., Sharifi Ashoorabadi, E., Afiuni, D. 2017. Study of effective environmental factors on Thyme quality and quantity in field and habitat conditions. Plant Ecophysiology (Arsanjan Branch), 9(29): 195-203.

Sato, S., Ikeda, H., Furukawa, H., Murata, Y. and Tomoda, M. 2004. Effect of nutrient solution concentration on inorganic and glycyrrhizin content Glycyrrhiza glabra. Yakugaku Zasshi. 124(10): 705-709.

Sharma, S., Arunachalam, K., and Arunachalam, A. 2022. Morphology and physiology of Perilla frutescens (Linn.) Britt in relation to micro-climate and edaphic characteristics Tropical Ecology, 1-12. doi.org/10.1007/s42965-021-00195-w

Shen, Q., Qin, X., Wang, X., Tian, Sh., Xiang, Y. and Zhao, J. 2014. Effects of plant density on the economic yield and agronomic characters of Perilla frutescens L., Journal of Agricultural Science and Technology, 15(9): 1516-1520.

Siriamornpun, S., Li, D., Yang. L., Suttajit, S. and Suttajit, M., 2006. Variation of lipid and fatty acid composition in Thai Perilla seeds grown at different locations. Songklanakarin Journal of Science and Technology, 28(1): 17-21.

Sonboli, A., Kanani, M., Yousefzadi, M. and Mojarad, M. 2009. Chemical composition and antibacterial activity of the essential oil of Salvia hydrangea from two localities of Iran. Journal of Medicinal Plants, 8(30): 20-28. (In Persian)

Tajali, A.A., Amin, Gh.R. and Gandomkar Ghalhari, A. 2009. Study and identification compounds of essential oil of Camphorosma monspeliaca in different phonological Stages in Arak, Hamedan and Shahr-E-Kord Rangelands. Rangeland, 3(2): 302-316. (In Persian)

Tian, J., Zeng, X.B., Zhang, S., Wang, Y.Z., Zhang, P., Lu, A.J. and Peng, X. 2014. Regional variation in components and antioxidant and antifungal activities of Perilla frutescens essential oils in China. Industrial Crops and Products, 59: 69–79.

Wei, M.-C., Wang, C.-S., Wei, D.-H. and Yang, Y.-C. 2021. Insights into the supercritical CO₂ extraction of Perilla oil and its theoretical solubility. Processes, 9: 239.

Yavari, A. 2022. Study on essential oil variability of Salvia sharifii Rech. f. & esfand. in different natural habitats of Hormozgan Province. Eco-phytochemical Journal of Medicinal Plants, 9(4): 33-47. (In Persian)