Investigating the effect of jasmonic acid on the quantitative and qualitative changes of secondary metabolites of different organs from Scrophularia striata
Subject Areas : Medicinal Plants
Elham Ahmadi
1
(
Department of Agronomy and Plant Breeding, Faculty of Agriculture, Ilam University, Ilam, Iran
)
Arash Fazeli
2
(
Department of Agronomy and Plant Breeding, Faculty of Agriculture, Ilam University, Ilam, Iran
)
Zeinab Rostami
3
(
Department of Agronomy and Plant Breeding, Faculty of Agriculture, Ilam University, Ilam, Iran
)
Keywords: Ilam, Jasmonic acid, Secondary metabolites, GC Mass, Scrophularia striata Boiss,
Abstract :
Scrophularia striata Boiss is a member of the Lamiaceae family, a valuable plant and native to Iran, which despite its rich medicinal potential, there is limited information about the type and amount of secondary compounds. Therefore, the use of modern gas chromatography methods (such as GC-Mass technology) can provide comprehensive and sufficient information about the amount and type of secondary compounds. In the present study, the effect of jasmonic acid at three levels (0 (control), 100 and 300) ppm on changes in secondary metabolites in different tissues (roots and aerial tissue) of this plant was investigated. Aerial parts and roots of the plant were extracted after drying by Soxhlet method. Chemical analysis of the obtained extracts was performed using gas chromatography apparatus connected to a mass spectrometer. The results of chemical analysis showed that different concentrations of methyl jasmonate induce the biosynthesis of a number of secondary compounds, especially phenylpropanoid compounds. Such as tetradecamethyl (%8/69), dodecamethyl- (%7/31), 2,3-Dihydro-benzofuran (%5/35), 2-Methoxy-4-vinylphenol (%9/32), 2- Furancarboxaldehyde (%4/03), Ethyl .alpha.-d-glucopyranoside (%19/87), 4-vinylphenol (%12/64), Methyl beta-D-glucopyranoside (%26/28), 2-Propenoic acid , 3- (4-methoxyphenyl) - (Cinnamic acid) (%21/02) and 2-Propenoic acid, 3-phenyl-, (E) - (Cinnamic acid) (%14/57) highest in the aerial and roots of the plants were treated and controlled. The general results show that the presence of some useful and effective compounds, especially antibacterial substances, requires further studies to identify useful pharmacological and medicinal compounds in this plant.
Abd El‐Raouf, O.M., El‐Sayed, E.S.M. and Manie, M.F. 2015. Cinnamic acid and cinnamaldehyde ameliorate cisplatin‐induced splenotoxicity in rats. Journal of Biochemical And Molecular Toxicology 29(9): 426-431.
Badami, S., Gupta, M.K. and Suresh, B. 2003. Antioxidant activity of the ethanolic extract of Striga orobanchioides. Journal of Ethnopharmacology 85(2-3): 227-230.
Bahrami, A. and Valadi, A. 2010. Effects of Scrophularia striata ethanolic leaves extracts on Staphylococcus aureus. International Journal of Pharmacology 6(4): 431-434.
Balbi, V. and Devoto, A. 2008. Jasmonate signalling network in Arabidopsis thaliana: crucial regulatory nodes and new physiological scenarios. New Phytologist 177(2): 301-318.
Bazi-Zlan, R., Fazeli, A., Zarei, B. and Erfani Moghadam, J. 2022. The effect of salicylic acid on the activity of catalase and peroxidase enzymes and the content of phenol and flavonoid of (Scrophularia striata L.) under water deficit stress 14(3): 57-68.
Bruni, R. and Sacchetti, G. 2009. Factors affecting polyphenol biosynthesis in wild and field grown St. John’s Wort (Hypericum perforatum L. Hypericaceae/Guttiferae). Molecules 14(2): 682-725.
Carvalho, A.A., Andrade, L.N., de Sousa, É.B.V. and de Sousa, D.P. 2015. Antitumor phenylpropanoids found in essential oils. BioMed research international, 2015: 1-21.
Chidambara Murthy, K.N., Jayaprakasha, G.K. and Singh, R.P. 2002. Studies on antioxidant activity of pomegranate (Punica granatum) peel extract using in vivo models. Journal of Agricultural and Food Chemistry 50(17): 4791-4795.
Ellard-Ivey, M. and Douglas, C.J. 1996. Role of jasmonates in the elicitor-and wound-inducible expression of defense genes in parsley and transgenic tobacco. Plant physiology 112(1): 183-192.
Epple, P., Apel, K. and Bohlmann, H. 1997. Overexpression of an endogenous thionin enhances resistance of Arabidopsis against Fusarium oxysporum. The Plant Cell 9(4): 509-520.
Garrido, G., González, D., Lemus, Y., Garcıa, D., Lodeiro, L., Quintero, G., Delporte, C., Núñez Sellés, A.J. and Delgado, R. 2004. In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG®). Pharmacological Research 50(2): 143-149.
Ghahreman, M. 1996. A dictionary of Iranian plants. Farhang Moasser, Tehran (in Persian).
Giri, C.C. and Zaheer, M. 2016. Chemical elicitors versus secondary metabolite production in vitro using plant cell, tissue and organ cultures: recent trends and a sky eye view appraisal. Plant Cell, Tissue and Organ Culture (PCTOC) 126(1): 1-18.
Halder, M., Sarkar, S. and Jha, S. 2019. Elicitation: A biotechnological tool for enhanced production of secondary metabolites in hairy root cultures. Engineering in Life Sciences 19(12): 880-895.
Howlett, B.J. .2006. Secondary metabolite toxins and nutrition of plant pathogenic fungi. Current opinion in plant biology 9(4): 371-375.
Jung, S. 2004. Effect of chlorophyll reduction in Arabidopsis thaliana by methyl jasmonate or norflurazon on antioxidant systems. Plant Physiology and Biochemistry 42(3): 225-231.
Kim, D. H., Han, S. I., Go, B., Oh, U.H., Kim, C. S., Jung, Y. H., Lee, J. and Kim, J. H. 2019. 2-methoxy-4-vinylphenol attenuates migration of human pancreatic cancer cells via blockade of fak and akt signaling. Anticancer research 39(12): 6685-6691.
Korkina, L.G., Mikhal’Chik, E., Suprun, M., Pastore, S. and Dal Toso, R. 2007. Molecular mechanisms underlying wound healing and anti-inflammatory properties of naturally occurring biotechnologically produced phenylpropanoid glycosides. Cell Mol Biol 53(5): 84-91.
Kozlowski, G., Buchala, A. and Métraux, J. P. 1999. Methyl jasmonate protects Norway spruce [Picea abies (L.) Karst.] seedlings against Pythium ultimum Trow. Physiological and Molecular Plant Pathology 55(1): 53-58.
Liu, C., Liu, Y. and Yan, X.y. 2008. Effects of plumbagin on the human breast cancer cell mda-mb-231 in vitro. West China Journal of Pharmaceutical Sciences 23(1): 42.
Mahboubi, M., Kazempour, N. and Nazar, A.R.B. 2013. Total phenolic, total flavonoids, antioxidant and antimicrobial activities of Scrophularia striata Boiss. extracts. Jundishapur Journal of Natural Pharmaceutical Products 8(1): 15 (in Persian).
Malheiro, J.F., Maillard, J.-Y., Borges, F. and Simões, M. 2019. Evaluation of cinnamaldehyde and cinnamic acid derivatives in microbial growth control. International Biodeterioration and Biodegradation 141: 71-78.
Mendoza, D., Cuaspud, O., Arias, J.P., Ruiz, O. and Arias, M. .2018. Effect of salicylic acid and methyl jasmonate in the production of phenolic compounds in plant cell suspension cultures of Thevetia peruviana. Biotechnology reports 19: e00273.
Meurer-Grimes, B., McBeth, D.L., Hallihan, B. and Delph, S. 1996. Antimicrobial activity in medicinal plants of the Scrophulariaceae and Acanthaceae. International journal of pharmacognosy 34(4): 243-248.
Monsef-Esfahani, H.R., Hajiaghaee, R., Shahverdi, A.R., Khorramizadeh, M.R. and Amini, M. 2010. Flavonoids, cinnamic acid and phenyl propanoid from aerial parts of Scrophularia striata. Pharmaceutical biology 48(3): 333-336 (in Persian).
Naik, P.M. and Al-Khayri, J.M. 2016. Abiotic and biotic elicitors–role in secondary metabolites production through in vitro culture of medicinal plants. Abiotic and Biotic Stress in Plants, Recent Advances Future Perspectives. IntechOpen: 247-277.
Natarajan, D., Britto, S.J., Srinivasan, K., Nagamurugan, N., Mohanasundari, C. and Perumal, G. 2005. Anti-bacterial activity of Euphorbia fusiformis—A rare medicinal herb. Journal of Ethnopharmacology 102(1): 123-126.
Park, S.U., Chae, Y.A. and Facchini, P. 2003. Genetic transformation of the figwort, Scrophularia buergeriana Miq., an Oriental medicinal plant. Plant cell reports 21(12): 1194-1198.
Pasdaran, A. and Hamedi, A. 2017. The genus Scrophularia: a source of iridoids and terpenoids with a diverse biological activity. Pharmaceutical biology 55(1): 2211-2233.
Qian, J., Hunkler, D. and Rimpler, H. 1992. Iridoid-related aglycone and its glycosides from Scrophularia ningpoensis. Phytochemistry 31(3): 905-911.
Rezaie-Tavirani, M., Mortazavi, S.A., Barzegar, M., Moghadamnia, S.H. and Rezaee, M.B. 2010. Study of anti cancer property of Scrophularia striata extract on the human astrocytoma cell line (1321). Iranian journal of pharmaceutical research: IJPR 9(4): 403 (in Persian).
Rostami, Z., Fazeli, A. & Hojati, Z. 2022. The isolation and expression analysis of cinnamate 4-hydroxylase and chalcone synthase genes of Scrophularia striata under different abiotic elicitors. Scitific reports 12, 8128. 1-14.
Rubab, M., Chelliah, R., Saravanakumar, K., Barathikannan, K., Wei, S., Kim, J.R., Yoo, D., Wang, M.H. and Oh, D.H. 2020. Bioactive potential of 2-methoxy-4-vinylphenol and benzofuran from Brassica oleracea L. var. capitate f, rubra (Red Cabbage) onoxidative and microbiological stability of Beef Meat. Foods 9(5): 568.
Shouhani, B., Hemati, A.A. and Taheri, M.M. 2010. Effects of Scrophularia striata extract on wound healing in rabbit. Journal Of Ilam University Of Medical Sciences 17(4): 9-16 (in Persian).
Uchegbu, R.I., Bako, S.S., Ngozi-Olehi, L.C. and Achinihu, I.O. 2015. GC/MS analysis and identification of phytochemicals present in the fruits of Mormodica balsamina Linn. IOSR J Appl Chem 8: 39-42.
van Fürden, B., Humburg, A. and Fuss, E. 2005. Influence of methyl jasmonate on podophyllotoxin and 6-methoxypodophyllotoxin accumulation in Linum album cell suspension cultures. Plant cell reports 24(5): 312-317.
Wang, R., Yang, W., Fan, Y., Dehaen, W., Li, Y., Li, H., Wang, W., Zheng, Q. and Huai, Q. 2019. Design and synthesis of the novel oleanolic acid-cinnamic acid ester derivatives and glycyrrhetinic acid-cinnamic acid ester derivatives with cytotoxic properties. Bioorganic chemistry 88: 102951.
Wasternack, C. and Parthier, B. 1997. Jasmonate-signalled plant gene expression. Trends in plant science 2(8): 302-307.
Wu, S., Xu, T. and Huang, D. 2015. Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis. journal of food and drug analysis 23(2): 253-259.
Zhang, Y., Mian, M. and Bouton, J. 2006. Recent molecular and genomic studies on stress tolerance of forage and turf grasses. Crop Science 46(2): 497-511.
Fathi, I., Majdi, M., Maroufi, A., & Dastan, D. (2020). Expression pattern analysis of some genes involved in the biosynthetic pathway of terpenoids and phenylpropanoids in tissues, developmental stages and under methyl jasmonate treatment in yarrow (Achillea millefolium subsp. millefolium). Cellular and Molecular Research (Iranian Journal of Biology), 33(1), 87-102.
Dianat M, Saharkhiz MJ, Tavassolian I (2016) Salicylic acid mitigatesdrought stress in Lippia citriodora L.: effects on biochemical traitsand essential oil yield. BiocatalAgric Biotechnol 8:286–293.
Shakirovam, F.M., Sakhbutdiova, A.R., Bezrukova, M.V., Fatkhutdinova, R.A.,Fatkhtdinova, D.R., (2003). Change in the hormonal status of Wheat seedling induced by salicylic acid and salinity. Plant Science, 164, 317-322.
Bahmani F, Kazemeini H, Hoseinzadeh-Chahkandak F, Farkhondeh T, Sedaghat M. (2019). Sedation with medicinal plants: A review of medicinal plants with sedative properties in Ira - nian ethnoblotanical documents. Plant Biotechnol Persa. 1 (1): 13-24.
Kerdar, T. Rabienejad, N. Alikhani, Y. Moradkhani, SH. Dastan, D. (2019). Clinical, in vitro and phytochemical, studies of Scrophularia striata mouthwash on chronic periodontitis disease. Journal of Ethnopharmacology. 239, 111872.
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Abd El‐Raouf, O.M., El‐Sayed, E.S.M. and Manie, M.F. 2015. Cinnamic acid and cinnamaldehyde ameliorate cisplatin‐induced splenotoxicity in rats. Journal of Biochemical And Molecular Toxicology 29(9): 426-431.
Badami, S., Gupta, M.K. and Suresh, B. 2003. Antioxidant activity of the ethanolic extract of Striga orobanchioides. Journal of Ethnopharmacology 85(2-3): 227-230.
Bahrami, A. and Valadi, A. 2010. Effects of Scrophularia striata ethanolic leaves extracts on Staphylococcus aureus. International Journal of Pharmacology 6(4): 431-434.
Balbi, V. and Devoto, A. 2008. Jasmonate signalling network in Arabidopsis thaliana: crucial regulatory nodes and new physiological scenarios. New Phytologist 177(2): 301-318.
Bazi-Zlan, R., Fazeli, A., Zarei, B. and Erfani Moghadam, J. 2022. The effect of salicylic acid on the activity of catalase and peroxidase enzymes and the content of phenol and flavonoid of (Scrophularia striata L.) under water deficit stress 14(3): 57-68.
Bruni, R. and Sacchetti, G. 2009. Factors affecting polyphenol biosynthesis in wild and field grown St. John’s Wort (Hypericum perforatum L. Hypericaceae/Guttiferae). Molecules 14(2): 682-725.
Carvalho, A.A., Andrade, L.N., de Sousa, É.B.V. and de Sousa, D.P. 2015. Antitumor phenylpropanoids found in essential oils. BioMed research international, 2015: 1-21.
Chidambara Murthy, K.N., Jayaprakasha, G.K. and Singh, R.P. 2002. Studies on antioxidant activity of pomegranate (Punica granatum) peel extract using in vivo models. Journal of Agricultural and Food Chemistry 50(17): 4791-4795.
Ellard-Ivey, M. and Douglas, C.J. 1996. Role of jasmonates in the elicitor-and wound-inducible expression of defense genes in parsley and transgenic tobacco. Plant physiology 112(1): 183-192.
Epple, P., Apel, K. and Bohlmann, H. 1997. Overexpression of an endogenous thionin enhances resistance of Arabidopsis against Fusarium oxysporum. The Plant Cell 9(4): 509-520.
Garrido, G., González, D., Lemus, Y., Garcıa, D., Lodeiro, L., Quintero, G., Delporte, C., Núñez Sellés, A.J. and Delgado, R. 2004. In vivo and in vitro anti-inflammatory activity of Mangifera indica L. extract (VIMANG®). Pharmacological Research 50(2): 143-149.
Ghahreman, M. 1996. A dictionary of Iranian plants. Farhang Moasser, Tehran (in Persian).
Giri, C.C. and Zaheer, M. 2016. Chemical elicitors versus secondary metabolite production in vitro using plant cell, tissue and organ cultures: recent trends and a sky eye view appraisal. Plant Cell, Tissue and Organ Culture (PCTOC) 126(1): 1-18.
Halder, M., Sarkar, S. and Jha, S. 2019. Elicitation: A biotechnological tool for enhanced production of secondary metabolites in hairy root cultures. Engineering in Life Sciences 19(12): 880-895.
Howlett, B.J. .2006. Secondary metabolite toxins and nutrition of plant pathogenic fungi. Current opinion in plant biology 9(4): 371-375.
Jung, S. 2004. Effect of chlorophyll reduction in Arabidopsis thaliana by methyl jasmonate or norflurazon on antioxidant systems. Plant Physiology and Biochemistry 42(3): 225-231.
Kim, D. H., Han, S. I., Go, B., Oh, U.H., Kim, C. S., Jung, Y. H., Lee, J. and Kim, J. H. 2019. 2-methoxy-4-vinylphenol attenuates migration of human pancreatic cancer cells via blockade of fak and akt signaling. Anticancer research 39(12): 6685-6691.
Korkina, L.G., Mikhal’Chik, E., Suprun, M., Pastore, S. and Dal Toso, R. 2007. Molecular mechanisms underlying wound healing and anti-inflammatory properties of naturally occurring biotechnologically produced phenylpropanoid glycosides. Cell Mol Biol 53(5): 84-91.
Kozlowski, G., Buchala, A. and Métraux, J. P. 1999. Methyl jasmonate protects Norway spruce [Picea abies (L.) Karst.] seedlings against Pythium ultimum Trow. Physiological and Molecular Plant Pathology 55(1): 53-58.
Liu, C., Liu, Y. and Yan, X.y. 2008. Effects of plumbagin on the human breast cancer cell mda-mb-231 in vitro. West China Journal of Pharmaceutical Sciences 23(1): 42.
Mahboubi, M., Kazempour, N. and Nazar, A.R.B. 2013. Total phenolic, total flavonoids, antioxidant and antimicrobial activities of Scrophularia striata Boiss. extracts. Jundishapur Journal of Natural Pharmaceutical Products 8(1): 15 (in Persian).
Malheiro, J.F., Maillard, J.-Y., Borges, F. and Simões, M. 2019. Evaluation of cinnamaldehyde and cinnamic acid derivatives in microbial growth control. International Biodeterioration and Biodegradation 141: 71-78.
Mendoza, D., Cuaspud, O., Arias, J.P., Ruiz, O. and Arias, M. .2018. Effect of salicylic acid and methyl jasmonate in the production of phenolic compounds in plant cell suspension cultures of Thevetia peruviana. Biotechnology reports 19: e00273.
Meurer-Grimes, B., McBeth, D.L., Hallihan, B. and Delph, S. 1996. Antimicrobial activity in medicinal plants of the Scrophulariaceae and Acanthaceae. International journal of pharmacognosy 34(4): 243-248.
Monsef-Esfahani, H.R., Hajiaghaee, R., Shahverdi, A.R., Khorramizadeh, M.R. and Amini, M. 2010. Flavonoids, cinnamic acid and phenyl propanoid from aerial parts of Scrophularia striata. Pharmaceutical biology 48(3): 333-336 (in Persian).
Naik, P.M. and Al-Khayri, J.M. 2016. Abiotic and biotic elicitors–role in secondary metabolites production through in vitro culture of medicinal plants. Abiotic and Biotic Stress in Plants, Recent Advances Future Perspectives. IntechOpen: 247-277.
Natarajan, D., Britto, S.J., Srinivasan, K., Nagamurugan, N., Mohanasundari, C. and Perumal, G. 2005. Anti-bacterial activity of Euphorbia fusiformis—A rare medicinal herb. Journal of Ethnopharmacology 102(1): 123-126.
Park, S.U., Chae, Y.A. and Facchini, P. 2003. Genetic transformation of the figwort, Scrophularia buergeriana Miq., an Oriental medicinal plant. Plant cell reports 21(12): 1194-1198.
Pasdaran, A. and Hamedi, A. 2017. The genus Scrophularia: a source of iridoids and terpenoids with a diverse biological activity. Pharmaceutical biology 55(1): 2211-2233.
Qian, J., Hunkler, D. and Rimpler, H. 1992. Iridoid-related aglycone and its glycosides from Scrophularia ningpoensis. Phytochemistry 31(3): 905-911.
Rezaie-Tavirani, M., Mortazavi, S.A., Barzegar, M., Moghadamnia, S.H. and Rezaee, M.B. 2010. Study of anti cancer property of Scrophularia striata extract on the human astrocytoma cell line (1321). Iranian journal of pharmaceutical research: IJPR 9(4): 403 (in Persian).
Rostami, Z., Fazeli, A. & Hojati, Z. 2022. The isolation and expression analysis of cinnamate 4-hydroxylase and chalcone synthase genes of Scrophularia striata under different abiotic elicitors. Scitific reports 12, 8128. 1-14.
Rubab, M., Chelliah, R., Saravanakumar, K., Barathikannan, K., Wei, S., Kim, J.R., Yoo, D., Wang, M.H. and Oh, D.H. 2020. Bioactive potential of 2-methoxy-4-vinylphenol and benzofuran from Brassica oleracea L. var. capitate f, rubra (Red Cabbage) onoxidative and microbiological stability of Beef Meat. Foods 9(5): 568.
Shouhani, B., Hemati, A.A. and Taheri, M.M. 2010. Effects of Scrophularia striata extract on wound healing in rabbit. Journal Of Ilam University Of Medical Sciences 17(4): 9-16 (in Persian).
Uchegbu, R.I., Bako, S.S., Ngozi-Olehi, L.C. and Achinihu, I.O. 2015. GC/MS analysis and identification of phytochemicals present in the fruits of Mormodica balsamina Linn. IOSR J Appl Chem 8: 39-42.
van Fürden, B., Humburg, A. and Fuss, E. 2005. Influence of methyl jasmonate on podophyllotoxin and 6-methoxypodophyllotoxin accumulation in Linum album cell suspension cultures. Plant cell reports 24(5): 312-317.
Wang, R., Yang, W., Fan, Y., Dehaen, W., Li, Y., Li, H., Wang, W., Zheng, Q. and Huai, Q. 2019. Design and synthesis of the novel oleanolic acid-cinnamic acid ester derivatives and glycyrrhetinic acid-cinnamic acid ester derivatives with cytotoxic properties. Bioorganic chemistry 88: 102951.
Wasternack, C. and Parthier, B. 1997. Jasmonate-signalled plant gene expression. Trends in plant science 2(8): 302-307.
Wu, S., Xu, T. and Huang, D. 2015. Chemical compositions of the volatile extracts from seeds of Dendranthema nankingense and Borago officinalis. journal of food and drug analysis 23(2): 253-259.
Zhang, Y., Mian, M. and Bouton, J. 2006. Recent molecular and genomic studies on stress tolerance of forage and turf grasses. Crop Science 46(2): 497-511.
Fathi, I., Majdi, M., Maroufi, A., & Dastan, D. (2020). Expression pattern analysis of some genes involved in the biosynthetic pathway of terpenoids and phenylpropanoids in tissues, developmental stages and under methyl jasmonate treatment in yarrow (Achillea millefolium subsp. millefolium). Cellular and Molecular Research (Iranian Journal of Biology), 33(1), 87-102.
Dianat M, Saharkhiz MJ, Tavassolian I (2016) Salicylic acid mitigatesdrought stress in Lippia citriodora L.: effects on biochemical traitsand essential oil yield. BiocatalAgric Biotechnol 8:286–293.
Shakirovam, F.M., Sakhbutdiova, A.R., Bezrukova, M.V., Fatkhutdinova, R.A.,Fatkhtdinova, D.R., (2003). Change in the hormonal status of Wheat seedling induced by salicylic acid and salinity. Plant Science, 164, 317-322.
Bahmani F, Kazemeini H, Hoseinzadeh-Chahkandak F, Farkhondeh T, Sedaghat M. (2019). Sedation with medicinal plants: A review of medicinal plants with sedative properties in Ira - nian ethnoblotanical documents. Plant Biotechnol Persa. 1 (1): 13-24.
Kerdar, T. Rabienejad, N. Alikhani, Y. Moradkhani, SH. Dastan, D. (2019). Clinical, in vitro and phytochemical, studies of Scrophularia striata mouthwash on chronic periodontitis disease. Journal of Ethnopharmacology. 239, 111872.
