Investigation of the participation of hydroxamic acid derivatives in the protection of Malus domestica Borkh. from pathogens
DOI:
https://doi.org/10.59463/dbge1y37Keywords:
: hydroxamic acid, protection, Malus, flavonols, anthocyanins, pathogensAbstract
The aim of the article is show the response to biotic stress (in particular, fungal attack) using hydroxamic acid derivatives in the example of fruit plants. Two new compounds were synthesized at the Institute of Organic Chemistry of the NAS of Ukraine: compound No. 2 (C14H20N2O4S) and No. 3 (C14H20N2O4), compound No. 1 C12H16N2O4S was used as a control. Synthesized compounds No. 2 and No. 3 were tested in vivo on prototypes, representatives of the genus Malus Mill. are damaged by pathogenic fungi. An accumulation in the content of secondary metabolites after treatment with the compound C12H16N2O4S and a decrease after treatment with the compounds C14H20N2O4S and C14H20N2O4 was noted in the sites of hydroxamic acid application. Since substances of the flavonoid series are phytoalexins, the lesion of the plant by cytosporosis and powdery mildew leads to an increase in the content of flavonoids. Compounds No. 2 and No. 3 inhibit the development of pathogenic fungi, so there is no need for additional synthesis of flavonoids, compound № 1 does not have pronounced fungicidal properties. Considering the primary the primary results, we can judge further prospects for the study and use of synthesized hydroxamic acids (C14H20N2O4S) and (C14H20N2O4).
References
Abe, Y., Sulfones, I.V. (1960), The anti-bacterial activity in vitro and urine excretion of experimental animal. Osaka Shiritsu Daigaku Igaku Zashi, 9: 4029.
Alkiewiczt, J.Z., Eckesteini, H., Halweg, P., Krakouka, Urbanski T. (1957), Fungistatic activity of some hydroxamic acid. Nature, 180: 1204.
Andreeva, V.Yu., Kalinkina, G.I. (2000), Razrabotka metodiki kolichestvennogo opredeleniya flavonoidov v manzhetke obyknovennoj Alhcemilla vulgaris L.S.L. Himiya rastitelnogo syrya, 1: 85–88.
Arct, J.E., Czerwinska, Z., Eckestein, A., Ejmocki, R., Kowalik Sobetka, W., Zukowski, E. (1964), Synthesis and fungicidal activity of aryloxyalkane hydroxamic acids and analogs. Przeniysl Chem, 43: 332.
Bailey, J.A., Burden, R.S., Mynett, A., Brown, C. (1977), Metabolism of phaseollin by Septoria nodorum and other non-pathogens of Phaseolus vulgaris. Phytochemistry, 16: 1541–1544.
Bailey, J A., Mansfield, J.W. (1982), Phytoalexins. Blackie and Son, Glasgow, UK, pp. 334.
Bemheim, M.L.C. (1964). The enzymatic hydrolysis of certain hydroxamic acids. Archives of Biochemistry and Biophysics, 107: 313.
Bratfaleanu, O., Steinhauer, B. (1994), Degradation of avenalumins by fungi in vitro and in vivo. Mededelingen – Facultiet Landbouwkundige en Toegepaste Biologische Wetenschappen, 59: 877–884.
Brooks, C.J.W., Watson, D.G. (1985), Phytoalexins. Natural Product Reports, pp. 427–459.
Chen, X., Ding, A. B., Zhong, X. (2019), Functions and mechanisms of plant histone deacetylases. Science China Life Sciences, 62. https://doi.org/10.1007/s11427-019-1587-x
Coutts, R.T. (1967), Hydroxamic acids. I. Acyclic hydroxamic acids. Canadian Journal of [1] Pharmaceutical Sciences, 2: 1.
Eckstein, I.Z., Domanoka, H. (1965), Properties systemiques des derives des acides hydroxamiques. Medel Landbonwhogesch Opzoekingssta Staat Gent, 30: 2007.
Eckstein, Z., Urbanski, T. (1956), Fungicide activities of some aryloacetohydroxamic acids. Bulletin of the Academy of Polish Sciences, 4: 627.
Eckstein, Z., Czerwinskafejgin, Z. E. (1959), The properties and fungicidal activity of aryloxy-acetohydroxamic acids. Przemsysl Chem, 38: 213.
Goncharovska, I.V., Levon, V.F. (2021), Content of anthocyanins in the bark of fruit and berry plants due to adaptation to low temperatures. Khimiya Rastitel'nogo Syr'ya, 1: 233–239. https://doi.org/10.14258/jcprm.2021017747
Goncharovska, I. V., Levon, V. F., Kyznetsov, V. V., Antonyuk, G. O. (2022), Identification of vitamin C in flowers and leaves Malus spp. Khimiya Rastitel'nogo Syr'ya, 3: 243–248. https://doi.org/10.14258/jcprm.20220310874
Grombacher, A.W., Russell, W. A., Guthrie, W.D. (1989), Resistance to first-generation European corn borer (Lepidoptera: Pyralidae) and Dimboa concentration in midwhorl leaves of the BS9 maize synthetic. Journal of the Kansas Entomological Society, 62: 103–107.
Guthrie, W.D., Tseng, C.T., Russell, W.A., Coats, J.R., Robbins, J.J., Tollefson, J.J. (1986), Dimboa content at seven stages of plant development in a maize synthetic cultivar. Journal of the Kansas Entomological Society, 59: 356–360.
Hammerschmidt, R., Dann, E. K. (1999), The role of phytoalexins in plant protection. Novartis Foundation Symposium, 223: 175–190.
Harborne, J.B. (1999), The comparative biochemistry of phytoalexin induction in plants. Biochemical Systematics and Ecology, 27: 335–367.
Hofman, J., Hofmanovâ, O. (1969), 1,4-Benzoxazin derivatives in plants. Sephadex fractionation and identification of a new glucoside. European Journal of Biochemistry, 8, 109–112.
Huang, C. Y., Chi, L. L., Huang, W. J., Chen, Y. W., Chen, W. J., Kuo, Y. C., Yuan, C. M., Chen, C. N. (2012), Growth stimulating effect on queen bee larvae of histone deacetylase inhibitors. Journal of Agricultural and Food Chemistry, 60: 613–949.
Kriventsov, V. I. (1982), Methodical recommendations on the analysis of fruits on biochemical structure. Yalta, 21.
Kwak, S.Y., Yang, J.K., Choi, H.R., Park, K.C., Kim, Y.B., Lee, Y.S. (2013), Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant. Bioorganic & Medicinal Chemistry Letters, 23: 1136–42.
Martini, S., D’Addario, C., Colacevich, A., Focardi, S., Borghini, F., Santucci, A., Figura, N., Rossi, C. (2009), Antimicrobial activity against Helicobacter pylori strains and antioxidant properties of blackberry leaves (Rubus ulmifolius) and isolated compounds. International Journal of Antimicrobial Agents, 34(1): 50-59. https://doi.org/10.1016/j.ijantimicag.2009.01.010
Morrissey, J.P., Osbourn, A.E. (1999), Fungal resistance to plant antibiotics as a mechanism of pathogenesis. Microbiology and Molecular Biology Reviews, 63: 708–724.
Mostafa, I.Y., Zayed, S., Farghaly, M. (1966), Fungicidal properties of thioacetohydroxamic acids and related compounds. Archives of Microbiology, 55: 324.
Papadopoulos, G. N., Kokotos, C. G. (2016), Photoorganocatalytic one-pot synthesis of hydroxamic acids from aldehydes. Chemistry – A European Journal, 22: 6964–6967.
Patanun, O., Ueda, M., Itouga, M., Kato, Y., Utsumi, Y., Matsui, A., Tanaka, M., Utsumi, C., Sakakibara, H., Yoshida, M., Narangajavana, J., Seki, M. (2017), The histone deacetylase inhibitor suberoylanilide hydroxamic acid alleviates salinity stress in cassava. Frontiers in Plant Science, 7: 2039. https://doi.org/10.3389/fpls.2016.02039
Rodrigues, G.C., Feijo, D.F., Bozza, M.T., Pan, P., Vullo, D., Parkkila, S., Supuran, C.T., Capasso, C., Aguiar, A.P., & Vermelho, A.B. (2014), Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas' disease. Journal of Medicinal Chemistry, 57: 298–308.
Schwalb, A., Schwalb, S.J., Burns, K. (1999), Holocene environments from stable isotope stratigraphy of ostracods and authigenic carbonate in Chilean Altiplano Lakes. Palaeogeography, Palaeoclimatology, Palaeoecology, 148: 153–168.
Smith, C.J. (1996), Accumulation of phytoalexins: defense mechanism and stimulus response system. New Phytologist, 132: 1–45.
Szot, I., Goncharovska, I., Klymenko, S., Bulakh, P. (2022), Importance of old and local apple cultivars. Agrobiodiversity for Improving Nutrition, Health and Life Quality, 6(2): 156–170. https://doi.org/10.15414/ainhlq.2022.0017
VanEtten, H.D., Funnell-Baerg, D., Wasmann, C., McCluskey, K. (1994a). Location of pathogenicity genes on dispensable chromosomes in Nectria haematococca MP VI. Antonie van Leeuwenhoek, 65: 263–267.
VanEtten, H.D., Mansfield, J.W., Bailey, J.A., Farmer, E.E. (1994b), Two classes of plant antibiotics: phytoalexins versus ‘phytoanticipins’. The Plant Cell, 6: 1191–1192.
Virtanen, A.I., Hietala, P.K. (1960), Precursors of benzoxazolinone in rye plants. I. Precursor II, the aglucone. Acta Chemica Scandinavica, 14: 499–502.
Yang, K., Nong, K., Gu, Q., Dong, J., Wang, J. (2018), Discovery of N-hydroxy-3-alkoxybenzamides as direct acid sphingomyelinase inhibitors using a ligand-based pharmacophore model. European Journal of Medicinal Chemistry, 151: 389–400.
