Cite this article as:

Mironova N. V., Korobko V. V., Pchelintseva N. V., Krylatova J. G., Zhestovskaya E. S. The Phytotesting of (thio)semicarbazones 2,4-diarylbicyclo[3.3.1]non-2-en-9-ones. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2019, vol. 19, iss. 3, pp. 304-311. DOI: https://doi.org/10.18500/1816-9775-2019-19-3-305-311

This is an open access article distributed under the terms of Creative Commons Attribution 4.0 International License (CC-BY 4.0).
Heading: 
Biology
UDC: 
581.144+547.71/.72/.78
Language: 
Russian

The Phytotesting of (thio)semicarbazones 2,4-diarylbicyclo[3.3.1]non-2-en-9-ones

Authors: 
Mironova Natalya V., Saratov State University , 83, Astrakhanskaya str., Saratov, 410012, Russia , mironovanatasha97@mail.ru
Korobko Valeria V., Saratov State University , 83, Astrakhanskaya str., Saratov, 410012, Russia , v.v.korobko@mail.ru
Pchelintseva Nina V., SSU. Institute of Chemistry. Department of Organic and Bioorganic Chemistry, 410012, Saratov, Astrakhanskaya str., 83, building. 1, Institute of Chemistry, SSU, pchelinzevanvV555@mail.ru
Krylatova Jana G., Saratov State University , 83, Astrakhanskaya str., Saratov, 410012, Russia , yana.krylatova@yandex.ru
Zhestovskaya Elizaveta S., Research Associate, «Signal», Moscow, zhestovskayae@gmail.com
Abstract

Biological testing of (thio) semicarbazones 2,4-diarylbicyclo [3.3.1] non2-en-9-ones, differing in the nature of aryl substituents and nucleophile, was carried out.The object of the study was seedlings of spring soft wheat Triticum aestivum L. of the Saratovskaya 36 variety. To assess the physiological activity of the tested compounds, we used a valuable analysis of the morphometric parameters of growth of the root system and shoots of the test and control plants and the quantitative content of chlorophyll a, chlorophyll b, and carotenoids in the first leaf. The study of the physiological activity of (thio)semicarbazones 2,4-diarylbicyclo [3.3.1] non-2-en-9-ones showed that the test compounds in some concentrations affect the growth of the aerial parts of plants, having a positive effect on the indicator of the root-availability. The tests revealed the relationship between shoot growth and the concentration of the tested solutions. It has been established that (thio)semicarbazones 2,4-diarylbicyclo[3.3.1]non-2-en-9-ones at a concentration of 10-6 M contribute to an increase in chlorophyll b content and a decrease in the ratio of chlorophylls a and b.

Key words: 
carbocyclic compounds, biotesting, Triticum aestivum L
DOI: 
https://doi.org/10.18500/1816-9775-2019-19-3-305-311
References
  1. Romanovskiy I. V., Boltromeyuk V. V., Gidranovich L. G., Rineyskaya O. N. Bioorganicheskaya khimiya: uchebnik [Bioorganic chemistry: a textbook]. Minsk, Novoe znanie Publ.; Moscow, INFRA-M Publ., 2015. 504 p. (in Rus- sian).
  2. Bystrov N. S., Chernov B. K., Dobrynin V. N., Kolo- sov M. N. The structure of hyperforin. Tetrahedron Let- ters, 1975, vol. 16, no. 32, pp. 2791–2794.
  3. Spessard S. J., Stoltz B. M. Progress toward the synthesis of garsubellin A and related phloroglucins: the direct diastereoselective synthesis of the bicyclo3.3.1.nonane core. Organic Letters, 2002, vol. 4, no. 11, pp. 1943–1946.DOI: https://doi.org/10.1021/0l5020043
  4. Kraus G. A., Hon Y. S., Sy J. Synthesis of bicycle 3.2.1.oc- tanes by ring contraction. The Journal of Organic Chem- istry, 1986, vol. 51, pp. 2625–2627.
  5. Brondz I., Greibrokk T., Groth P. A., Aasen A. J. The relative stereochemistry of hyperforin–an antibiotic from Hypericum perforatum L. Tetrahedron Letters, 1982, vol. 23, no. 12, pp. 1299–1300.
  6. Kolevatova Ya. G., Men’shova M. A., Pchelintseva N. V. 2,4-Diarilbiciklo[3.3.1]non-2-en-9-ony: sintez, stroenie, svojstva [2,4-Diarylbicyclo [3.3.1] non-2-en-9-ones: synthesis, structure, properties]. In: Karbonil’nye soedi- neniya v sinteze geterotsiklov: sb. nauch. tr. [Carbonyl compounds in the synthesis of heterocycles. Coll. of Sci. Papers]. Saratov, Nauchnaya kniga Publ., 2008, pp. 128–130 (in Russian).
  7. Sadym A. V., Lagunin A. A., Filimonov D. A., Poroy- kov V.  V. Internet system for predicting the spectrum  of biological activity of chemical compounds. Chemi- cal Pharmaceutical Journal, 2002, vol. 36, no. 10, pp. 21–26 (in Russian).DOI: https://doi.org/10.30906/0023-1134-2002-36-10-21-26
  8. Poroikov V. V., Filimonov D. A., Borodina Yu. V., Lagu- nin A. A., Kos A. Robustness of biological activity spectra predicting by computer program PASS for non-congeneric sets of chemical. Journal of Chemical Information and Computer Sciences, 2000, vol. 40, no. 6, pp. 1349–1355.
  9. Korobko V. V., Pchelintseva N. V., Samsonova E. A., Batalin S. D., Lunejva М. A. Effect of N, O, S-contaning Heterocyclic Compounds on Growth of Root System of Triticum aestivum L. Izv. Saratov Univ. (N. S.), Ser. Chem- istry. Biology. Ecology, 2018, vol. 18, iss. 1, pp. 45–51 (in Russian).DOI: https://doi.org/10.18500/1816-9775-2018-18-1-45-51
  10. Gubina T. I., Ukhova A. A., Isaeva S. V., Tumskiy R. S., Anis'kov A. A., Klochkova I. N. The Determination of Biological Effects of New Heterocyclic Compounds on Plants and the Evaluation of Environmental Safety of Their Application. Izv. Saratov Univ. (N. S.), Ser. Chemis- try. Biology. Ecology, 2017, vol. 17, iss. 3, pp. 267–273 (in Russian).DOI: https://doi.org/10.18500/1816-9775-2017-17-3-267-273
  11. Kolevatova Ya. G. 2,4-Diarilbiciklo[3.3.1]non-2-en-9- ony: sintez, stroenie i nekotorye khimicheskie prevrash- cheniya [2,4-Diarylbicyclo[3.3.1]non-2-en-9-ones: syn- thesis, structure and some chemical transformations. Dis. Cand. Sci. (Chem.)]. Saratov, 2009. 139 p. (in Russian).
  12. Zhestovskaya E. S., Krylatova Ya. G. Sintez 2,4-dini- trofenilgidrazonov i tiosemikarbazonov 2,4-diarilbicik- lo[3.3.1]non-2-en-9-onov[Synthesis of 2,4-dinitrophe- nylhydrazones and thiosemicarbazones 2,4-diarylbicyclo [3.3.1] non-2-en-9-ones]. Voprosy biologii, ekologii, himii i metodiki obucheniya: sb. nauch. st. [Questions of Biology, Ecology, Chemistry and Teaching Methods : Coll. of Sci. Articles], 2012, iss. 14, pp. 38–39 (in Russian).
  13. Golub N. A. Parametry pervichnoy kornevoy sistemy ozimoy pshenitsy i vozmozhnosti ikh ispol’zovaniya v otsenke sortov [Parameters of the primary root system of winter wheat and the possibility of their use in the evaluation of varieties]. In: Fiziologiya produktivnosti i ustoichivosti zernovykh kul'tur: sb. nauch. tr. [Physiology of productivity and stability of grain crops: coll. of proc.]. Krasnodar, KNIICH Publ., 1988, pp. 42–47(in Russian).
  14. Gavrilenko V. F., Zhigalova T. V. Bol’shoy praktikum po fotosintezu [Great Photosynthesis Workshop]. Moscow, “Akademiya” Publ., 2003. 256 p. (in Russian).
  15. Tkachev V. I ., Gulyaev B. I. Response of plants of different winter wheat varieties to a brief soil drought. Physiology and Biochemistry of Cultivated Plants, 2010, vol. 42, no. 6, pp. 522–529 (in Russian).
  16. Korobko V. V., Stepanov S. A. Vliyanie temperatury na razvitie kornevoy sistemy prorostkov tvyordoy pshenitsy [The effect of temperature on the development of the root system of durum wheat seedlings]. Voprosy biologii, ekologii, himii i metodiki obucheniya: sb. nauch. st. [Questions of Biology, Ecology, Chemistry and Teaching Methods: Coll. of Sci. Articles]. Saratov, Izd-vo Sarat. un-ta, 2017, iss. 19, pp. 3–6 (in Russian).
  17. Ivanov L. A., Ivanova L. A., Ronzhina D. A., Yudina P. K. Changes in the chlorophyll and carotenoid contents in the leaves of steppe plants along a latitudinal gradient in South Ural. Russian Journal of Plant Physiology, 2013, vol. 60, no. 6, pp. 812–820 (in Russian).DOI: https://doi.org/10.7868/S0015330313050072
  18. Maslova T. G., Popova I. A. Adaptive properties of the plant pigment systems. Photosynthetica, 1993, vol. 29, pp. 195–203.
  19. Mokronosov A. T., Gavrilenko V. F., Zhigalova T. V. Fotosintez: Fiziologo-ekologicheskie i biohimicheskie aspekty [Photosynthesis: Physiological, Environmental and Biochemical Aspects]. Moscow, “Academiya” Publ., 2006. 448 p. (in Rissian).
  20. Smolikova G. N., Laman N. A., Boriskevich O. V. The role of chlorophylls and carotenoids in seed resistance to abiotic stressors. Russian Journal of Plant, 2011, vol. 58, no. 6, pp. 817–825 (in Rissian).
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