بررسی تنوع فیتوشیمیایی عصاره اتانولی پوست درخت Fraxinus excelsior L. در رویشگاه‌های مختلف جنگل‌های هیرکانی در استان مازندران
محورهای موضوعی :
فیتوشیمی
معصومه سلیمانی رحیم ابادی
1
,
سید محمد حسینی نصر
2
,
حمید جلیلوند
3
,
سید محمد حجتی
4
,
پوریا بی پروا
5
1 - دانشجوی دکتری، گروه جنگل شناسی و اکولوژی دانشگاه کشاورزی و منابع طبیعی ساری، مازندران، ایران
2 - دانشیار، گروه جنگل شناسی و اکولوژی دانشگاه کشاورزی و منابع طبیعی ساری، مازندران، ایران
3 - استاد، گروه جنگل شناسی و اکولوژی دانشگاه کشاورزی و منابع طبیعی ساری، مازندران، ایران
4 - دانشیار، گروه جنگل شناسی و اکولوژی دانشگاه کشاورزی و منابع طبیعی ساری، مازندران، ایران،
5 - دانشیار، گروه جنگل شناسی و اکولوژی دانشگاه کشاورزی و منابع طبیعی ساری، مازندران، ایران
تاریخ دریافت : 1399/09/17
تاریخ پذیرش : 1400/03/08
تاریخ انتشار : 1400/06/01
کلید واژه:
مازندران,
پوست,
کارواکرول,
اسکوپولتین,
زبان‌گنجشک,
چکیده مقاله :
زبان گنجشک (Fraxinus excelsior L.)، گونه ای جنگلی با فعالیت های همه جانبه بیولوژیکی و دارویی است که از عصاره اندام های مختلف آن به‌عنوان الگویی برای ساخت ترکیبات جدید در درمان بیماری های مختلف انسان استفاده می شود. در این تحقیق به‌منظور بررسی چگونگی تاثیرپذیری خصوصیات بیوشیمیایی این گونه جنگلی از شرایط محیطی، چهار رویشگاه پرچینک، امره، الندان و قارن سرا با حدود ارتفاعی 200 تا 1400 متری، در حوزه آبخیز تجن و سیاهرود در استان مازندران انتخاب شدند. در هر رویشگاه نمونه های پوست از سه درخت (تکرار) در فصل تابستان برداشت شد. استخراج عصاره‌‌ها به روش خیساندن با اتانول صورت گرفت. مهم ترین ترکیبات شیمیایی عصاره‌‌ها با استفاده از کروماتوگراف گازی متصل به طیف‌سنج جرمی مورد شناسایی قرار گرفت و مشخصه های فیزیکو شیمیایی خاک نیز اندازه گیری شد. مقادیر مهم ترین ترکیبات شناسایی شده شامل بنزن - اتانول (33/30- 35/51 درصد)، دی- آلوز (20/6- 72/31 درصد)، اسکوپولتین (65/14- 83/26 درصد)، تیروزول - استات (37/5- 06/9 درصد)، کارواکرول (0-93/4 درصد)، هومو وانیل - الکل (84/3- 53/6 درصد) در چهار رویشگاه مورد نظر با افزایش ارتفاع افزایش یافت که با عناصر غذایی پرمصرف خاک رابطه منفی مشاهده شد. در این میان تنها پلی فنول تیروزول-استات رفتاری متفاوت از سایر ترکیبات داشته به نوعی که با عامل ارتفاع از سطح دریا رابطه منفی و با مقادیر کربن و فسفر قابل جذب خاک همبستگی مثبت نشان داد. نتایج حاکی از تاثیرپذیری ترکیبات شیمیایی پوست درخت از شرایط رویشگاهی است. با توجه افزایش میزان مواد موثره پوست در ارتفاعات بالاتر که طبعا باعث افزایش مقاومت گیاه در برابر پاتوژنها می شود، به نظر می‌رسد کاشت این گونه در ارتفاعات به منظور تامین اهداف چندگانه در جنگل کاری ها بازدهی بیشتری دارد.
چکیده انگلیسی:
Fraxinus excelsior L. is a forest species with versatile biological and medicinal activities that its extracts are used as a model for making new compounds in the treatment of various human diseases. In this study, in order to investigate how the biochemical characteristics of this forest species are affected by environmental conditions, four habitats of Perchink, Amreh, Alandan and Qarnsara with an altitude of 200 to 1400 meters, were selected in Tajan and Siahroud watersheds located in Mazandaran province. In each habitat, skin samples were taken from 3 trees (repeated) in summer. Ethanol extracts were obtained by maceration and were analyzed by GC/MS and the physical and chemical properties of the soil samples were measured. The most important compounds of extracts were included: benzeneethanol (30.33-51.35%), d-allose (6.20-31.72%), scopoletin (14.65-26.83%), tyrosol acetate (5.37-9.06%), carvacrol (0-4.93%), homovanillyl alcohol (3.84- 6.53%) which increased with increasing altitude. Also, there was negative relationship between the identified compounds and soil nutrients. Among them, only polyphenol tyrosol acetate behaved differently from the other compounds in a way that showed a negative relationship with the altitude factor and a positive correlation with the amount of carbon and absorbable phosphorus in the soil. Also, the chemical composition of d-allose was not observed in Perchink habitat. These results were showed that the chemical properties of this tree skin are affected by habitat conditions, which caused increases the species' resistance to pathogens. As a result, considering that the amount of active ingredients in this species was higher at higher altitudes and the presence of these compounds increases the resistance to pathogens, it seems planting this species is more productive at higher altitudes to achieve multiple goals in afforestation.
منابع و مأخذ:
Ali Ahyaei, M., and Behbahanizadeh, A.A. 1993. Description of soil chemical decomposition methods. Research Organization. Agricultural education and promotion. Soil and Water Research Institute. 467P (In Persian).
Acebey, A., Kromer, T., Maass, B.L. and Kessler, M. 2010. Ecological distribution of potentially useful species of Araceae and Bromeliaceae as non- timber forest products in Bolivia. Jornal of Biodiversity Conservation, 19: 2553-2564.
Alizadeh Banouti, R., Rostami shahraji, T. and Mohebi bijarpas, M. 2017. An investigation on the Fraxinus excelsior plantation under different situations of physiography (Case Study: Dooleychal, Masouleh, Guilan province). 70(3): 422-430.
Attanzio, A., D'Anneo A., Pappalardo, F., Paolo Bonina, F., Antonia Livera, M., Allegra, M. and Tesoriere, L. 2019. Phenolic composition of hydrophilic extract of Manna from Sicilian Feaxinus angustifolia and its reducing, antioxidant and anti-inflammatory activity in vitro. Jornal of Antioxidants, 8:1-13.
Akter, K., Park, W.S., Kim, H., Khalil, A.A. Kh., and Ahn, M. 2020. Comparative studies of Fraxinus species from Korea using microscopic characterization, phytochemical analysis, and anti-lipase enzyme activity. Journal of Plants, 9: 1-18.
Belcher, B., Ruiz Peirez, M. and Achdiawan, R. 2005. Global patterns and trends in the use and management of commercial NTFPs: implications for livelihoods and conservation. Jornal of World Development, 33: 1435-1452.
Bertome J., Arrillage I.M., and Segura, J. 2007. Essential oil variation whitin and among natural population of Lavandula latifolia and its relation to their ecological areas. Jornal of Biochemical systematics and Ecology, 35: 479-488.
Baser, K.H.C. 2008. Biological and pharmacological activities of carvacrol and carvacrol bearing essential oils. Journal of current pharmaceutical design, 14: 3106-3120.
Berini, J., Brockman, S.A., Hegeman, A.D., Reich, P.B., Muthukrishnan, R., Montgomery, R.A. and Forester, J.D. 2018. Combinations of abiotic factors differentially alter production of plant secondary metabolites in five woody plant species in the boreal-temperate transition zone. Journal of Frontiers in Plant Science, 9:1-17.
Bernini, R., Carastro, I., Santoni F. and Clemente, M. 2019. Synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. Journal of Antioxidants, 8:1-9.
Cleary, M., Andersson, P., Broberg, A., Elfstrand. M., Daniel, G. and Stenlid, J. 2014.Genotypes of Fraxinus excelsior with different susceptibility to the ash dieback pathogen Hymenoscyphus pseudoalbidus and their response to the phytotoxin viridiol–A metabolomic and microscopic study. Jornal of Phytochemistry, 102: 115-125.
Celedon, J.M. and Bohlmann, J. 2017. An extended model of heartwood secondary metabolism informed by functional genomics. Jornal of Tree Physiology, 38: 311-319.
Dobrowolska, D., Dein. S., Osterbaan, A., Wagner, S., Clarrk, J. and Skovsgaardg, P. 2011. A review of European ash: implications for silviculture. Jornal of Forestry, 84: 133-148.
Douglas, G.C., McNamara, J., O'Connell, K., Dunne, L. and Grant, J. 2017. Vegetative propagation of dieback-tolerant Fraxinus excelsior on a commercial scale in:" dieback of European ash (Fraxinus ): consequences and guidelines for sustainable management" the report on European cooperation in science & technology (COST) action FP1 103 FRAXBACK pp. 288-299 Edited by: Vasaitis R. and Enderle R. Publisher: Swedish University of Agricultural Sciences.
Eyles, A., Jones, W., Riedl, K., Cipollini, D., Schwartz, S., Chan, K., Herms, D.A. and Bonello, P. 2007. Comparative phloem chemistry of Manchurian (Fraxinus mandshurica) and two North American ash species (Fraxinus americana and Fraxinus pennsylvanica). Jornal of Chemistry and Ecology, 33: 1430–1448.
Gnonlonfin, G.J.B., Sanni, A. and Brimer, L. 2012. Review scopoletin – a coumarin phytoalexin with medicinal properties, Journal of plant Science, 47-54.
Hassan, S. and Mathesius, U. 2012. The role of flavonoids in root–rhizosphere signalling: opportunities and challenges for improving plant–microbe interactions. Journal of experimental botany, 63: 3429-3444.
Hashimoto, F., Nishiumi, S., Miyake, O., Takeichi H., Chitose, M., Ohtsubo, H., Ishimori, Sh., Ninchojo, T., Hashimura, Y., Kaito, H., Morisada, N., Morioka, I., Fukuoka, H., Yoshida, M. and Iijima, K. 2013. Metabolomics analysis of umbilical cordblood clarifies changes in saccharidesassociated with delivery method. Journal of EarlyHuman Development, 89: 315-320.
Jafari Haghighi, M. 2003. Soil decomposition methods. Nedaye Zoha Publications. 236 P. (in Persian)
Jung, H.A., Islam, M.D., Kwon, Y.S., Jin, S.E., Son, Y.K., Park, J.J., Sohn, H.S. and Choi, J.S. 2011. Extraction and identification of three major aldose reductase inhibitors from Artemisia montana. Jornal of Food Chem Toxicol, 49: 376-384
Kostova, I. and Iossifova, T. 2007. Chemical components of Fraxinus Journal of Fitoterapia, 78: 85-106.
Karuppusamy, S. 2009. A review on trends in production of secondary metabolites from higher plants by in vitro tissue, organ and cell cultures. Journal of Medicinal Plants Research, 3(13): 1222-1239.
Kaveh, M., Tavassoli, A., Azadi, R and Memariani, F. 2014. Morphology and micromorphology of the genus Fraxinus in Iran. Journal of Botany, 20: 188-200.
Kachur, K. and Suntres, Z. 2019. The antibacterial properties of phenolic isomers, carvacrol and thymol. Journal of Food Science and Nutrition, 51: 1-13.
Kalampaliki, A.D., Giannouli, V., Skaltsounis, A.L. and Kostakis, I. 2019. A three-step, gram-scale synthesis of hydroxytyrosol, hydroxytyrosol acetate, and 3, 4 dihydroxyphenylglycol, Journal of molecules, 24: 1-13.
Karimi, A., Krahmer, A., Herwig, N., Schulz, H., Hadian, J. and Meiners, T. 2020. Original Research, 11: 1-15.
Liu, R., Sun, Q., Sun, A. and Cui, J. 2005. Isolation and purification of coumarin compounds from cortex Fraxinus by high-speed counter-current chromatography. Journal of Chromatogram, 29: 195–199
Li, Q.J., Wang, M.L., Yang, X.S., Ma, L. and Hao, X.J. 2013. Two new coumarin glycosides from Chimonanthus nitens. Journal of Asian natural products research, 15: 270-275.
Liu Y., Li, Y., Luo W., and Liu, Sh. 2020. Soil potassium is correlated with root secondary metabolites and root-associated core bacteria in licorice of different ages. Journal of Plant soil, 456: 61-79.
Middleton, P., Stewart, F., Al-Qahtani, S., Egan, P., O'Rourke, C., Abdulrahman, A., Byres, M., Middleton, M., Kumarasamy, Y., Shoeb, M., Nahar, L., Delazar, A. and Sarker, S.D. 2005. Antioxidant, antibactrial activities and general toxicity of Alnus glutinosa, Fraxinus excelsior and Papaver rhoeas. Journal of Pharmaceutical Research, 2: 81-86.
Mateos, R., Pereira-Caro, G., Saha, S., Cert, R., Redondo-Horcajo, M., Bravo, L. and Kroon, P.A. 2011. Acetylation of hydroxytyrosol enhances its transport across differentiated Caco-2 cell monolayers. Journal of Food chemistry, 125: 865- 872.
Mehri-Rad, N., Payamenoor, V., and Nazari, J. 2016. Effect of base age and light on callus production of Betula litwinowii and induced botulin in vitro. Journal of genetic research and breeding of range and forest plants of Iran, 23:93-102. (In Persian).
Munoz, F., Marçais, B., Dufour, J., and Dowkiw, A. 2016. Rising out of the ashes: additive genetic variation for crown and collar resistance to Hymenoscyphus fraxineus in Fraxinus
excelsior. Journal of Phytopathology, 106:1535-1543.
Noguchi, C., Kamitori, K., Hossain, A., Hiroshi, H., Ayako, K., Youyi, D., Li S., Tokuda, M. and Fuminori, Y. 2016. DAllose inhibits cancer cell growth byreducing gLUT1 expression. The TohokuJournal of Experimental Medicine, 238: 131-141.
Naghdi Badi, H., Abdollahi, M., Mehrafarin, A., Ghorbanpour, M., Toylat, M., Gaderi, A. and Ghiaci, Y. 2017. An overview on two valuable natural and bioactive compounds, thymol and carvacrol, in medicinal plants. Journal of Medicinal Plants, 16(63): 1-32
Nemesio-Gorriz, M., Menezes, R.M., Paetz, Ch., Hammerbacher, A., Steenackers, M., Schamp, K., Hofte, M., Svatos, A., Gershenzon, J. and Douglas, G.C. 2020. Metabolomics in Fraxinus excelsior; identification and validation of biochemical markers for tolerance to ash dieback. Journal of Experimental Botany, 6-30.
Oussalah, M., Caillet, S., Saucier, L. and Lacroix, M. 2007. Inhibitory effects of selected plant essential oils on the growth of four pathogenic bacteria: E-coli O157: H7, Salmonella typhimurium, Staphylococcus aureus and Listeria monocytogenes. Journal of Food Control, 18 (5):414-420.
Ormeno, E. and Fernandez, C. 2012. Effect of soil nutrient on production and diversity of volatile terpenoids from plants. Journal of Current Bioactive Compounds, 8: 71-79
Santoyo, S., Cavero, S., Jaime, L., Ibanez, E., Senorans, F.J. and Reglero, G. 2006. Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare: Determination of optimal extraction parameters. Journal of Food Protection, 69 (2): 369-375.
Plumb, W.J., Coker, T.L., Stocks, J.J., Woodcock, P., Quine, C.P., Nemesio‐Gorriz, M., Douglas, G.C., Kelly, L.J. and Buggs, R.J. 2019. The viability of a breeding programme for as in the British Isles in the face of ash dieback. Journal of Plants People Planet, Issue 1.
Qazi, S., Lombardo, D. and Abou-Zaid, M. 2018. A metabolomic and HPLC-MS/MS analysis of the foliar phenolics, flavonoids and coumarins of the Fraxinus species resistant and susceptible to emerald ash borer. Journal of Molecules, 23, 2734.
Richard, A.G., Mafuru, C.S., Paul, M., Kayombo, C.J., Kashindye, A.M., Chirenje, L.I. and Musamba, E.B. 2011. Human activities influencing deforestation on meru catchment forest Reserve. Tanzania. Journal of Human Ecoligy, 33(1):17-20.
Shaza Anwar, A.L. and Frdoos Mohammad, A.F. 2014. Antibacterial activity of various plants extracts against antibiotic-resistant Aeromonas hydrophila. Journal of jondishapur microbial, 7(7): 1-7.
Sui, L., Nomura, R., Dong, Y., Fominori, Y., Ken, I. and Massaki, T. 2007.Cryoprotective effects of d-allose onmammalian cells. Journal of Cryobiology, 55: 87–92.
Sambles, C.M, Salmon, D.L., Florance, H., Howard, T.P., Smirnoff, N., Nielsen, L.R., cKinney, L.V., Kjaer, E.D., Buggs, R.J.A. and Studholme, D.J. 2017. Ash leaf metabolomes veal differences between trees tolerant and susceptible to ash dieback disease. Journal of cientific data, 4:170-190.
Sarfraz, I., Rasul, A., Jabeen, F., Younis, T., Zahoor, M.K., Arshad, M., and Ali, M. 2017. Fraxinus: A plant with versatile pharmacological and biological activities. Journal of Evidence-Based Complementary and Alternative Medicine, 34: 1-12.
Sancho-Knapik, D., Sanz, M.A., Peguero-Pina, J.J, Niinemets, U. and Gil-Pelegrin, E. 2017. Changes of secondary metabolites in Pinus sylvestris needle under increasing soil water deficit. Journal of Annals of Forest Science, 74: 24-29.
Sollars, E.S.A., Harper, A.L., Kelly, L.J., Sambles, C.M., Ramirez-Gonzalez, R.H., Swarbreck, D., Kaithakottil, G., Cooper, E.D., Uauy, C. and Havlickova, L. 2017. Genome sequence and genetic diversity of European ash trees. Journal of Nature, 541- 212.
Sultana, Sh., Ali, M., Jameel, M. and Sharma, P. 2018. Chemical constituents from the leaves of Fraxinus excelsior , Senna sulfurea (Collad.) H.S. Irwin et Barneby and Prosopis cineraria (L.) Druce. Journal of Trend phytochemical research, 2(4): 243-252.
Shintani, T. 2019. Food industrial production ofmonosaccharides using microbial, enzymatic,and chemical methods. Journal of Fermentation, 5:
Sobuj, N., Virjamo, V., Yaodan, Zh., Nybakken, L. and Julkunen-Titto, R. 2019. Impacts of elevated temperature and CO2 concentration on growth and phenolics in the sexually dimorphic Populus tremula (L.). Joiurnal of Environmental and Experimental Botany, 146: 34-44.
Serreli, G. 2018. Deiana, M. Biological relevance of extra virgin olive oil polyphenols metabolites. Journal of Antioxidants, 7: 170-175.
Tanaka, S. 2011. Sakamoto H. effects of d-alloseon the endocytic activity of dendritic cellsand the subsequent stimulation of T cells. Journal of Cell Immunol, 271: 141–146.
Talamond, P., Verdeil, J.L. and Conejero, G. 2015. Secondary metabolite localization by autofluorescence in living plant cells. Journal of Molecules, 20: 5024- 5037.
Thomas, P.A. 2016. Biological flora of the British Isles: Fraxinus excelsior. Journal of Ecology, 104: 1158-1209.
Touhami, I., Ghazghazi, H., Sellimi, H., Khaldi, A. and Mahmoudi, H. 2017. Antioxidant activities and phenolic contents of bark and leave extracts from Tunisian native tree: Fraxinus angustifolia Subsp. Angustifolia, Journal of New sciences, 45(5): 2496- 2501.
Uddin Khan, N.M.M. and Hossain, Md.S. 2015. Scopoletin and β-sitosterol glucoside from roots of Ipomoea digitata. Journal of Pharmacognosy and Phytochemistry, 4(2): 5-7.
Vamanu, E. and Ilie, A.M. 2015. Antioxidanet and inhibition of xanthine oxidase potentials of fluidized bed extracts from leaves of the ash tree. Journal of Natural products, 11: 81-89.
Verma, N. and Shukla, S. 2015. Impact of various factors responsible for fluctuation in plant secondary metabolites. Journal of Applied Research on Medicinal and Aromatic Plants, 1-7.
Villari, C., Herms, D.A., Whitehill, J.G., Cipollini, D. and Bonello, P. 2016. Progress and gaps in understanding mechanisms of ash tree resistance to emerald ash borer, a model for wood‐boring insects that kill angiosperms. Journal of New Phytologist, 209: 63-79.
Vanekova, Z., Vanek, M., Skvarenina, J., and Nagy M. 2020. The influence of local habitat and microclimate on the levels of secondary metabolites in Slovak bilberry (Vaccinium myrtillus) fruits. Journal of Plants, 9: 1-11.
Whitehill, J.G., Popova-Butler, A., Green-Church, K.B., Koch, J.L, Herms, D.A. and Bonello, P. 2011. Interspecific proteomic comparisons reveal ash phloem genes potentially involved in constitutive resistance to the emerald ash borer, Journal of Chemical ecology, 38: 499-511.
Yang, L., Wen. K.S., Ruan, X., Zhao, Y.X., Wei, F. and Wang, Q. 2018. Response of plant secondary metabolites to environmental factors. Journal of Molecules, 23: 762.
Yuan, Y., Tang, X., Jia, Zh. , Li, Ch., Ma, Jieyi. and Zhang, J. 2020. The effects of ecological factors on the main medicinal components of Dendrobium officinale under different cultivation modes. Journal of Forests, 11: 1-16.
Zhang, D., Qi, Q., Tong, S., Wang, X., An, Y., Zhang, M. and Lu, X. 2019. Soil degradation effects on plant diversity and nutrient in tussock meadow wetlands. Journal of Soil Scientific Plant Nutrient, 1–10.
Lee, B.Z., Kim, K.M., Chae, S., Jeong, S., Lee, S., Hong, K. and Lee, I.S. 2020. New coumarins isolated from the stem bark of Fraxinus rhynchophylla inhibit human neutrophil elastase and LPS-induced inflammation in RAW 264.7 cells, Journal of Phytochemistry Letters, 35: 78-83.
_||_
Ali Ahyaei, M., and Behbahanizadeh, A.A. 1993. Description of soil chemical decomposition methods. Research Organization. Agricultural education and promotion. Soil and Water Research Institute. 467P (In Persian).
Acebey, A., Kromer, T., Maass, B.L. and Kessler, M. 2010. Ecological distribution of potentially useful species of Araceae and Bromeliaceae as non- timber forest products in Bolivia. Jornal of Biodiversity Conservation, 19: 2553-2564.
Alizadeh Banouti, R., Rostami shahraji, T. and Mohebi bijarpas, M. 2017. An investigation on the Fraxinus excelsior plantation under different situations of physiography (Case Study: Dooleychal, Masouleh, Guilan province). 70(3): 422-430.
Attanzio, A., D'Anneo A., Pappalardo, F., Paolo Bonina, F., Antonia Livera, M., Allegra, M. and Tesoriere, L. 2019. Phenolic composition of hydrophilic extract of Manna from Sicilian Feaxinus angustifolia and its reducing, antioxidant and anti-inflammatory activity in vitro. Jornal of Antioxidants, 8:1-13.
Akter, K., Park, W.S., Kim, H., Khalil, A.A. Kh., and Ahn, M. 2020. Comparative studies of Fraxinus species from Korea using microscopic characterization, phytochemical analysis, and anti-lipase enzyme activity. Journal of Plants, 9: 1-18.
Belcher, B., Ruiz Peirez, M. and Achdiawan, R. 2005. Global patterns and trends in the use and management of commercial NTFPs: implications for livelihoods and conservation. Jornal of World Development, 33: 1435-1452.
Bertome J., Arrillage I.M., and Segura, J. 2007. Essential oil variation whitin and among natural population of Lavandula latifolia and its relation to their ecological areas. Jornal of Biochemical systematics and Ecology, 35: 479-488.
Baser, K.H.C. 2008. Biological and pharmacological activities of carvacrol and carvacrol bearing essential oils. Journal of current pharmaceutical design, 14: 3106-3120.
Berini, J., Brockman, S.A., Hegeman, A.D., Reich, P.B., Muthukrishnan, R., Montgomery, R.A. and Forester, J.D. 2018. Combinations of abiotic factors differentially alter production of plant secondary metabolites in five woody plant species in the boreal-temperate transition zone. Journal of Frontiers in Plant Science, 9:1-17.
Bernini, R., Carastro, I., Santoni F. and Clemente, M. 2019. Synthesis of lipophilic esters of tyrosol, homovanillyl alcohol and hydroxytyrosol. Journal of Antioxidants, 8:1-9.
Cleary, M., Andersson, P., Broberg, A., Elfstrand. M., Daniel, G. and Stenlid, J. 2014.Genotypes of Fraxinus excelsior with different susceptibility to the ash dieback pathogen Hymenoscyphus pseudoalbidus and their response to the phytotoxin viridiol–A metabolomic and microscopic study. Jornal of Phytochemistry, 102: 115-125.
Celedon, J.M. and Bohlmann, J. 2017. An extended model of heartwood secondary metabolism informed by functional genomics. Jornal of Tree Physiology, 38: 311-319.
Dobrowolska, D., Dein. S., Osterbaan, A., Wagner, S., Clarrk, J. and Skovsgaardg, P. 2011. A review of European ash: implications for silviculture. Jornal of Forestry, 84: 133-148.
Douglas, G.C., McNamara, J., O'Connell, K., Dunne, L. and Grant, J. 2017. Vegetative propagation of dieback-tolerant Fraxinus excelsior on a commercial scale in:" dieback of European ash (Fraxinus ): consequences and guidelines for sustainable management" the report on European cooperation in science & technology (COST) action FP1 103 FRAXBACK pp. 288-299 Edited by: Vasaitis R. and Enderle R. Publisher: Swedish University of Agricultural Sciences.
Eyles, A., Jones, W., Riedl, K., Cipollini, D., Schwartz, S., Chan, K., Herms, D.A. and Bonello, P. 2007. Comparative phloem chemistry of Manchurian (Fraxinus mandshurica) and two North American ash species (Fraxinus americana and Fraxinus pennsylvanica). Jornal of Chemistry and Ecology, 33: 1430–1448.
Gnonlonfin, G.J.B., Sanni, A. and Brimer, L. 2012. Review scopoletin – a coumarin phytoalexin with medicinal properties, Journal of plant Science, 47-54.
Hassan, S. and Mathesius, U. 2012. The role of flavonoids in root–rhizosphere signalling: opportunities and challenges for improving plant–microbe interactions. Journal of experimental botany, 63: 3429-3444.
Hashimoto, F., Nishiumi, S., Miyake, O., Takeichi H., Chitose, M., Ohtsubo, H., Ishimori, Sh., Ninchojo, T., Hashimura, Y., Kaito, H., Morisada, N., Morioka, I., Fukuoka, H., Yoshida, M. and Iijima, K. 2013. Metabolomics analysis of umbilical cordblood clarifies changes in saccharidesassociated with delivery method. Journal of EarlyHuman Development, 89: 315-320.
Jafari Haghighi, M. 2003. Soil decomposition methods. Nedaye Zoha Publications. 236 P. (in Persian)
Jung, H.A., Islam, M.D., Kwon, Y.S., Jin, S.E., Son, Y.K., Park, J.J., Sohn, H.S. and Choi, J.S. 2011. Extraction and identification of three major aldose reductase inhibitors from Artemisia montana. Jornal of Food Chem Toxicol, 49: 376-384
Kostova, I. and Iossifova, T. 2007. Chemical components of Fraxinus Journal of Fitoterapia, 78: 85-106.
Karuppusamy, S. 2009. A review on trends in production of secondary metabolites from higher plants by in vitro tissue, organ and cell cultures. Journal of Medicinal Plants Research, 3(13): 1222-1239.
Kaveh, M., Tavassoli, A., Azadi, R and Memariani, F. 2014. Morphology and micromorphology of the genus Fraxinus in Iran. Journal of Botany, 20: 188-200.
Kachur, K. and Suntres, Z. 2019. The antibacterial properties of phenolic isomers, carvacrol and thymol. Journal of Food Science and Nutrition, 51: 1-13.
Kalampaliki, A.D., Giannouli, V., Skaltsounis, A.L. and Kostakis, I. 2019. A three-step, gram-scale synthesis of hydroxytyrosol, hydroxytyrosol acetate, and 3, 4 dihydroxyphenylglycol, Journal of molecules, 24: 1-13.
Karimi, A., Krahmer, A., Herwig, N., Schulz, H., Hadian, J. and Meiners, T. 2020. Original Research, 11: 1-15.
Liu, R., Sun, Q., Sun, A. and Cui, J. 2005. Isolation and purification of coumarin compounds from cortex Fraxinus by high-speed counter-current chromatography. Journal of Chromatogram, 29: 195–199
Li, Q.J., Wang, M.L., Yang, X.S., Ma, L. and Hao, X.J. 2013. Two new coumarin glycosides from Chimonanthus nitens. Journal of Asian natural products research, 15: 270-275.
Liu Y., Li, Y., Luo W., and Liu, Sh. 2020. Soil potassium is correlated with root secondary metabolites and root-associated core bacteria in licorice of different ages. Journal of Plant soil, 456: 61-79.
Middleton, P., Stewart, F., Al-Qahtani, S., Egan, P., O'Rourke, C., Abdulrahman, A., Byres, M., Middleton, M., Kumarasamy, Y., Shoeb, M., Nahar, L., Delazar, A. and Sarker, S.D. 2005. Antioxidant, antibactrial activities and general toxicity of Alnus glutinosa, Fraxinus excelsior and Papaver rhoeas. Journal of Pharmaceutical Research, 2: 81-86.
Mateos, R., Pereira-Caro, G., Saha, S., Cert, R., Redondo-Horcajo, M., Bravo, L. and Kroon, P.A. 2011. Acetylation of hydroxytyrosol enhances its transport across differentiated Caco-2 cell monolayers. Journal of Food chemistry, 125: 865- 872.
Mehri-Rad, N., Payamenoor, V., and Nazari, J. 2016. Effect of base age and light on callus production of Betula litwinowii and induced botulin in vitro. Journal of genetic research and breeding of range and forest plants of Iran, 23:93-102. (In Persian).
Munoz, F., Marçais, B., Dufour, J., and Dowkiw, A. 2016. Rising out of the ashes: additive genetic variation for crown and collar resistance to Hymenoscyphus fraxineus in Fraxinus
excelsior. Journal of Phytopathology, 106:1535-1543.
Noguchi, C., Kamitori, K., Hossain, A., Hiroshi, H., Ayako, K., Youyi, D., Li S., Tokuda, M. and Fuminori, Y. 2016. DAllose inhibits cancer cell growth byreducing gLUT1 expression. The TohokuJournal of Experimental Medicine, 238: 131-141.
Naghdi Badi, H., Abdollahi, M., Mehrafarin, A., Ghorbanpour, M., Toylat, M., Gaderi, A. and Ghiaci, Y. 2017. An overview on two valuable natural and bioactive compounds, thymol and carvacrol, in medicinal plants. Journal of Medicinal Plants, 16(63): 1-32
Nemesio-Gorriz, M., Menezes, R.M., Paetz, Ch., Hammerbacher, A., Steenackers, M., Schamp, K., Hofte, M., Svatos, A., Gershenzon, J. and Douglas, G.C. 2020. Metabolomics in Fraxinus excelsior; identification and validation of biochemical markers for tolerance to ash dieback. Journal of Experimental Botany, 6-30.
Oussalah, M., Caillet, S., Saucier, L. and Lacroix, M. 2007. Inhibitory effects of selected plant essential oils on the growth of four pathogenic bacteria: E-coli O157: H7, Salmonella typhimurium, Staphylococcus aureus and Listeria monocytogenes. Journal of Food Control, 18 (5):414-420.
Ormeno, E. and Fernandez, C. 2012. Effect of soil nutrient on production and diversity of volatile terpenoids from plants. Journal of Current Bioactive Compounds, 8: 71-79
Santoyo, S., Cavero, S., Jaime, L., Ibanez, E., Senorans, F.J. and Reglero, G. 2006. Supercritical carbon dioxide extraction of compounds with antimicrobial activity from Origanum vulgare: Determination of optimal extraction parameters. Journal of Food Protection, 69 (2): 369-375.
Plumb, W.J., Coker, T.L., Stocks, J.J., Woodcock, P., Quine, C.P., Nemesio‐Gorriz, M., Douglas, G.C., Kelly, L.J. and Buggs, R.J. 2019. The viability of a breeding programme for as in the British Isles in the face of ash dieback. Journal of Plants People Planet, Issue 1.
Qazi, S., Lombardo, D. and Abou-Zaid, M. 2018. A metabolomic and HPLC-MS/MS analysis of the foliar phenolics, flavonoids and coumarins of the Fraxinus species resistant and susceptible to emerald ash borer. Journal of Molecules, 23, 2734.
Richard, A.G., Mafuru, C.S., Paul, M., Kayombo, C.J., Kashindye, A.M., Chirenje, L.I. and Musamba, E.B. 2011. Human activities influencing deforestation on meru catchment forest Reserve. Tanzania. Journal of Human Ecoligy, 33(1):17-20.
Shaza Anwar, A.L. and Frdoos Mohammad, A.F. 2014. Antibacterial activity of various plants extracts against antibiotic-resistant Aeromonas hydrophila. Journal of jondishapur microbial, 7(7): 1-7.
Sui, L., Nomura, R., Dong, Y., Fominori, Y., Ken, I. and Massaki, T. 2007.Cryoprotective effects of d-allose onmammalian cells. Journal of Cryobiology, 55: 87–92.
Sambles, C.M, Salmon, D.L., Florance, H., Howard, T.P., Smirnoff, N., Nielsen, L.R., cKinney, L.V., Kjaer, E.D., Buggs, R.J.A. and Studholme, D.J. 2017. Ash leaf metabolomes veal differences between trees tolerant and susceptible to ash dieback disease. Journal of cientific data, 4:170-190.
Sarfraz, I., Rasul, A., Jabeen, F., Younis, T., Zahoor, M.K., Arshad, M., and Ali, M. 2017. Fraxinus: A plant with versatile pharmacological and biological activities. Journal of Evidence-Based Complementary and Alternative Medicine, 34: 1-12.
Sancho-Knapik, D., Sanz, M.A., Peguero-Pina, J.J, Niinemets, U. and Gil-Pelegrin, E. 2017. Changes of secondary metabolites in Pinus sylvestris needle under increasing soil water deficit. Journal of Annals of Forest Science, 74: 24-29.
Sollars, E.S.A., Harper, A.L., Kelly, L.J., Sambles, C.M., Ramirez-Gonzalez, R.H., Swarbreck, D., Kaithakottil, G., Cooper, E.D., Uauy, C. and Havlickova, L. 2017. Genome sequence and genetic diversity of European ash trees. Journal of Nature, 541- 212.
Sultana, Sh., Ali, M., Jameel, M. and Sharma, P. 2018. Chemical constituents from the leaves of Fraxinus excelsior , Senna sulfurea (Collad.) H.S. Irwin et Barneby and Prosopis cineraria (L.) Druce. Journal of Trend phytochemical research, 2(4): 243-252.
Shintani, T. 2019. Food industrial production ofmonosaccharides using microbial, enzymatic,and chemical methods. Journal of Fermentation, 5:
Sobuj, N., Virjamo, V., Yaodan, Zh., Nybakken, L. and Julkunen-Titto, R. 2019. Impacts of elevated temperature and CO2 concentration on growth and phenolics in the sexually dimorphic Populus tremula (L.). Joiurnal of Environmental and Experimental Botany, 146: 34-44.
Serreli, G. 2018. Deiana, M. Biological relevance of extra virgin olive oil polyphenols metabolites. Journal of Antioxidants, 7: 170-175.
Tanaka, S. 2011. Sakamoto H. effects of d-alloseon the endocytic activity of dendritic cellsand the subsequent stimulation of T cells. Journal of Cell Immunol, 271: 141–146.
Talamond, P., Verdeil, J.L. and Conejero, G. 2015. Secondary metabolite localization by autofluorescence in living plant cells. Journal of Molecules, 20: 5024- 5037.
Thomas, P.A. 2016. Biological flora of the British Isles: Fraxinus excelsior. Journal of Ecology, 104: 1158-1209.
Touhami, I., Ghazghazi, H., Sellimi, H., Khaldi, A. and Mahmoudi, H. 2017. Antioxidant activities and phenolic contents of bark and leave extracts from Tunisian native tree: Fraxinus angustifolia Subsp. Angustifolia, Journal of New sciences, 45(5): 2496- 2501.
Uddin Khan, N.M.M. and Hossain, Md.S. 2015. Scopoletin and β-sitosterol glucoside from roots of Ipomoea digitata. Journal of Pharmacognosy and Phytochemistry, 4(2): 5-7.
Vamanu, E. and Ilie, A.M. 2015. Antioxidanet and inhibition of xanthine oxidase potentials of fluidized bed extracts from leaves of the ash tree. Journal of Natural products, 11: 81-89.
Verma, N. and Shukla, S. 2015. Impact of various factors responsible for fluctuation in plant secondary metabolites. Journal of Applied Research on Medicinal and Aromatic Plants, 1-7.
Villari, C., Herms, D.A., Whitehill, J.G., Cipollini, D. and Bonello, P. 2016. Progress and gaps in understanding mechanisms of ash tree resistance to emerald ash borer, a model for wood‐boring insects that kill angiosperms. Journal of New Phytologist, 209: 63-79.
Vanekova, Z., Vanek, M., Skvarenina, J., and Nagy M. 2020. The influence of local habitat and microclimate on the levels of secondary metabolites in Slovak bilberry (Vaccinium myrtillus) fruits. Journal of Plants, 9: 1-11.
Whitehill, J.G., Popova-Butler, A., Green-Church, K.B., Koch, J.L, Herms, D.A. and Bonello, P. 2011. Interspecific proteomic comparisons reveal ash phloem genes potentially involved in constitutive resistance to the emerald ash borer, Journal of Chemical ecology, 38: 499-511.
Yang, L., Wen. K.S., Ruan, X., Zhao, Y.X., Wei, F. and Wang, Q. 2018. Response of plant secondary metabolites to environmental factors. Journal of Molecules, 23: 762.
Yuan, Y., Tang, X., Jia, Zh. , Li, Ch., Ma, Jieyi. and Zhang, J. 2020. The effects of ecological factors on the main medicinal components of Dendrobium officinale under different cultivation modes. Journal of Forests, 11: 1-16.
Zhang, D., Qi, Q., Tong, S., Wang, X., An, Y., Zhang, M. and Lu, X. 2019. Soil degradation effects on plant diversity and nutrient in tussock meadow wetlands. Journal of Soil Scientific Plant Nutrient, 1–10.
Lee, B.Z., Kim, K.M., Chae, S., Jeong, S., Lee, S., Hong, K. and Lee, I.S. 2020. New coumarins isolated from the stem bark of Fraxinus rhynchophylla inhibit human neutrophil elastase and LPS-induced inflammation in RAW 264.7 cells, Journal of Phytochemistry Letters, 35: 78-83.
