Растительные экдистероиды: химическая структура и биологическая активность



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Ахметкаримова Ж-Растительные экдистероиды химическая структура и биологическая активность

Список литературы



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  12. Galbraith M., Horn D. An insect-moulting hormone from a plant // Chemical Communications (London). ‒ 1966. № 24. ‒ C. 905-906. DOI:10.1039/C19660000905.

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  14. Dinan L., Whiting P., Girault J.-P., Lafont R., Dhadialla S. T., Cress E. D., Mugat B., Antoniewski C., Lepesant J.-A. Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor // Biochemical Journal. ‒ 1997. ‒ Vol. 327, № 3. ‒ C. 643-650. DOI: 10.1042/bj3270643.

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  22. Temirgaziyev B. S., Kučáková K., Baizhigit Y. A., Jurášek M., Džubák P., Hajdúch M., Dolenský B., Drašar P. B., Tuleuov B. I., Adekenov S. M. Bioavailability and structural study of 20-hydroxyecdysone complexes with cyclodextrins // Steroids. ‒ 2019. ‒ Vol. 147. ‒ C. 37-41. DOI:10.1016/j.steroids.2018.11.007.

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  24. Jia A., Li Y., Zhou J., Gao J. Three phytoecdysteroids from Sagina japonica and potential biotransforming pathways of japonicone // Chemistry of natural compounds. ‒ 2010. ‒ Vol. 46, № 5. ‒ C. 738-741. DOI:10.1007/s10600-010-9729-8.

  25. Mamadalieva N.Z., Youssef F.S., Ashour M.L., Akramov D.K., Sasmakov S.A., Ramazonov N.S., Azimova S.S. A comparative study on chemical composition and antimicrobial activity of essential oils from three Phlomis species from Uzbekistan // Natural product research. ‒ 2021. ‒ Vol. 35, № 4. ‒ C. 696-701. DOI:10.1080/14786419.2019.1591400.

  26. Ramazanov N.S., Bobayev I.D., Yusupova U.Y., Aliyeva N.K., Egamova F.R., Yuldasheva N.K., Syrov V.N. Phytoecdysteroids-containing extract from Stachys hissarica plant and its wound-healing activity // Natural product research. ‒ 2017. ‒ Vol. 31, № 5. ‒ C. 593-597. DOI:10.1080/14786419.2016.1205058.

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  28. Krasnov E., Saratikov A., Yakunina G. Inokosterone and ecdysterone from Rhaponticum carthamoides // Khimiya prirodnykh soedinenii. ‒ 1976. Vol. 12, №4. ‒ С.494-495.

  29. Yakubova M., Sakharova N. Dinamika soderzhaniya ekdisterona v podzemnikh organakh Rhaponticum carthamoides // Rastitelnye resursy. ‒ 1980. ‒ T. 16. ‒ C. 98-100.

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  31. Chobot V., Buchta V., Jahodářová H., Pour M., Opletal L., Jahodář L., Harant P. Antifungal activity of a thiophene polyine from Leuzea carthamoides // Fitoterapia. ‒ 2003. ‒ T. 74, № 3. ‒ C. 288-290. DOI:10.1016/S0367-326X(03)00027-3

  32. Geszprych A., Weglarz Z. Composition of essential oil from underground and aboveground organs of Rhaponticum carthamoides [Willd.] Iljin // Herba Polonica. ‒ 2002. ‒ T. 4, № 48. – C. 188-192.

  33. Kokoska L., Janovska D. Chemistry and pharmacology of Rhaponticum carthamoides: a review // Phytochemistry. ‒ 2009. ‒ T. 70, № 7. ‒ C. 842-855. DOI:10.1016/j.phytochem.2009.04.008.

  34. Havlik J., Budesinsky M., Kloucek P., Kokoska L., Valterova I., Vasickova S., Zeleny V. Norsesquiterpene hydrocarbon, chemical composition and antimicrobial activity of Rhaponticum carthamoides root essential oil // Phytochemistry. ‒ 2009. ‒ T. 70, № 3. ‒ C. 414-418. DOI:10.1016/j.phytochem.2008.12.018.

  35. Brekhman I., Dardymov I. New substances of plant origin which increase nonspecific resistance // Annual review of pharmacology. ‒ 1969. ‒ T. 9, № 1. ‒ C. 419-430. DOI:10.1146/annurev.pa.09.040169.002223.

  36. Syrov V., Kurmukov A. Anabolic activity of phytoecdysone-ecdysterone isolated from Rhaponticum carthamoides (Willd.) Iljin // Farmakologiia i Toksikologiia. ‒ 1976. ‒ T. 39, № 6. ‒ C. 690-693. PMID: 1030669.

  37. Slama K., Koudela K., Tenora J., Maťhová A. Insect hormones in vertebrates: anabolic effects of 20-hydroxyecdysone in Japanese quail // Experientia. ‒ 1996. ‒ T. 52, № 7. ‒ C. 702-706. DOI:10.1007/BF01925578.

  38. Gadzhieva R., Portugalov S., Paniushkin V., Kondrat'eva I. A comparative study of the anabolic action of ecdysten, leveton and Prime Plus, preparations of plant origin // Eksperimental'naia i klinicheskaia farmakologiia. ‒ 1995. ‒ T. 58, № 5. ‒ C. 46-48. PMID: 8704590.

  39. Syrov V., Nabiev A., Sultanov M. The effect of phytoecdisteroids on the bile secretion function of the liver in normal rats and in animals with experimental Hepatitis // Farmakologiia i Toksikologiia. ‒ 1986. ‒ T. 49, № 3. ‒ C. 100-103. PMID: 3720929.

  40. Plotnikov M., Aliev O., Vasil'ev A., MIu M., Dmitruk S., Krasnov E. Effect of Rhaponticum carthamoides extract on hemorheological properties of blood in rats with arterial hypertension // Eksperimental'naia i klinicheskaia farmakologiia. ‒ 2001. ‒ T. 64, № 6. ‒ C. 45-47. PMID: 11871238.

  41. Molokovskij D., Davydov V., Khegay M. Comparative estimation of antidiabetic activity of different adaptogenic vegetative preparations and extractions from plant material of some official medicinal plants // Rastit. resur. ‒ 2002. ‒ T. 38, № 4. ‒ C. 15-28.

  42. Koleckar V., Brojerova E., Rehakova Z., Kubikova K., Cervenka F., Kuca K., Jun D., Hronek M., Opletalova V., Opletal L. In vitro antiplatelet activity of flavonoids from Leuzea carthamoides // Drug and chemical toxicology. ‒ 2008. ‒ T. 31, № 1. ‒ C. 27-35. DOI:10.1080/01480540701688444.

  43. Maĭmeskulova L., Maslov L. Anti-arrhythmic effect of phytoadaptogens // Eksperimental'naia i klinicheskaia farmakologiia. ‒ 2000. ‒ T. 63, № 4. ‒ C. 29-31. PMID: 11022302.

  44. Vershinina S. On the effect of Leuzea carthamoides extract and sarcolysin on the course of lympholeukosis in NK-Ly mice // Vopr Onkol. ‒ 1967. ‒ T. 13, № 5. ‒ C. 99-101. PMID: 5599271.

  45. Kormosh N., Laktionov K., Antoshechkina M. Effect of a combination of extract from several plants on Cell‐mediated and humoral immunity of patients with advanced ovarian cancer // Phytotherapy research. ‒ 2006. ‒ T. 20, № 5. ‒ C. 424-425. DOI10.1002/ptr.1889.

  46. Kokoska L., Janovska D., Rada V., Nepovim A., Vanek T. In Vitro. Antibacterial activity of four leuzea. species // Pharmaceutical biology. ‒ 2005. ‒ T. 43, № 1. ‒ C. 8-11. DOI:10.1080/13880200590903237.

  47. Osipova S., ZhI I., Syrov V., Badalova N., Khushbaktova Z. Ecdysten in the treatment of giardiasis // Meditsinskaia parazitologiia i parazitarnye bolezni. ‒ 2002. № 1. ‒ C. 29-33. PMID: 12224262.

  48. Petkov V., Roussinov K., Todorov S., Lazarova M., Yonkov D., Draganova S. Pharmacological investigations on Rhaponticum carthamoides // Planta medica. ‒ 1984. ‒ T. 50, № 03. ‒ C. 205-209. DOI: 10.1055/s-2007-969679.

  49. Kosar K., Opletal L., Vokac K., Harmatha J., Sovova M. Embryotoxicity of 20-hydroxyecdysone and poly-podine B from Leuzea carthamoides DC // Pharmazie. ‒ 1997. ‒ T. 52, № 5. ‒ C. 406-407.

  50. Chobot V., Vytlačilová J., Kubicová L., Opletal L., Jahodář L., Laakso I., Vuorela P. Phototoxic activity of a thiophene polyacetylene from Leuzea carthamoides // Fitoterapia. ‒ 2006. ‒ T. 77, № 3. ‒ C. 194-198. DOI:10.1016/j.fitote.2006.01.001.

REFERENCES


1. Сevostyanov A.E., et al., Prospects for the use of phytoecdysteroids in ophthalmology. Russian medical and biological bulletin named after academician I.P. Pavlov, 2006. 1: p. 8.


2. Girault, J.-P., et al., Ecdysone catabolism in the white mouse. 1988. 16(5): p. 716-720.
3. Akhrem, A. and Kovganko, N. Ecdysteroids: chemistry and biological activity. 1989. р. 247.
4. Shirshova, T.I., et al., Antimicrobial activity of native ecdysteroids of the plant Serratula coronata L. and some of their acyl derivatives. 2006. 40(5): p. 34-36.
5. Karlson, P. and Pulido, F.Manual de bioquímica. 1976: Marin.
6. Becker, E. and Plagge, E. Über das die Pupariumbildung auslösende Hormon der Fliegen. 1939. 59: p. 326-341.
7. Butenandt, A. and Karlson, P. Über die Isolierung eines metamorphose-hormons der insekten in kristallisierter form. 1954. 9(6): p. 389-391. DOI:10.1515/znb-1954-0601.
8. Karlson, P.J.P.i.b. and medicine, New concepts on the mode of action of hormones. 1963. 6(2): p. 203-214. DOI:10.1353/pbm.1963.0026.
9. Hoppe, W. and Huber, R. On the chemistry of ecdysone. II. Determination of the skeleton of sterin and its orientation by diffuse x-ray diffraction in ecdysone crystals. 1965. 98(7): p. 2353-2360. DOI: 10.1002/cber.19650980739.
10. Rice, E.L. Pest control with nature's chemicals. Allelochemics and pheromones in gardening and agriculture. 1983. р:224.
11. Nakanishi, K., et al., Insect hormones. The structure of ponasterone A, insect-moulting hormone from the leaves of Podocarpus nakaii Hay. 1966. (24): p. 915-917. DOI:10.1039/c19660000915.
12. Galbraith, M. and Horn, D.An insect-moulting hormone from a plant. 1966. (24): p. 905-906.
13. IMAI, S., et al., Isolation of cyasterone and ecdysterone from plant materials. 1969. 17(2): p. 340-342. DOI:10.1248/cpb.17.340.
14. Dinan, L., et al., Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor. 1997. 327(3): p. 643-650. DOI: 10.1042/bj3270643.
15. Yatsyuk, Y.K. and Lyashenko, S. Flavonoids of Serratula inermis. 1969. 5(1): p. 46-47. DOI:10.1007/BF00564927.
16. http://ecdybase.org/.
17. Yusupova, U.Y., et al., Phytoecdysteroids from the aerial part of Silene popovii. 2020. 56: p. 562-563. DOI:10.1007/s10600-020-03092-1.
18. Zibareva, L., et al., The phytoecdysteroid profiles of 7 species of Silene (Caryophyllaceae). 2009. 72(4): p. 234-248.
19. Dinan, L., et al., Phytoecdysteroids: diversity, biosynthesis and distribution, in Ecdysone: structures and functions. 2009, Springer. p. 3-45. DOI:10.1007/978-1-4020-9112-4_1.
20. Savchenko, R.G., et al., Sonochemically assisted 2, 3-dideoxygenation and skeletal rearrangement of ecdysteroid derivatives. 2019. 52: p. 505-511. DOI:10.1016/j.ultsonch.2018.12.029.
21. Tuleuov, B., et al., Structure and stereochemistry of phytoecdysone from Silene cretaceae fisch. 2014. 84(4): p. 704-707.
22. Temirgaziyev, B.S., et al., Bioavailability and structural study of 20-hydroxyecdysone complexes with cyclodextrins. 2019. 147: p. 37-41. DOI:10.1016/j.steroids.2018.11.007.
23. Zhou, X.-J., et al., Steroids and triterpenoids from Cucumis sativus roots. 2012. 48(3): p. 419-422. DOI:10.1007/s10600-012-0264-7.
24. Jia, A., et al., Three phytoecdysteroids from Sagina japonica and potential biotransforming pathways of japonicone. 2010. 46(5): p. 738-741. DOI:10.1007/s10600-010-9729-8.
25. Mamadalieva, N.Z., et al., A comparative study on chemical composition and antimicrobial activity of essential oils from three Phlomis species from Uzbekistan. 2021. 35(4): p. 696-701. DOI:10.1080/14786419.2019.1591400.
26. Ramazanov, N.S., et al., Phytoecdysteroids-containing extract from Stachys hissarica plant and its wound-healing activity. 2017. 31(5): p. 593-597. DOI:10.1080/14786419.2016.1205058.
27. Lamer-Zarawska, E., et al., Immunomodulatory activity of polysaccharide-rich fraction from Rhaponticum carthamoides leaves. 1996. 67(4): p. 371-372.
28. Krasnov, E., et al., Inokosterone and ecdysterone from Rhaponticum carthamoides. 1976.
29. Yakubova, M. and N.J.R.R. Sakharova, Dinamika soderzhaniya ekdisterona v podzemnikh organakh Rhaponticum carthamoides. 1980. 16: p. 98-100.
30. Hajdu, Z., et al., A Stilbene from the Roots of Leuzea c arthamoides. 1998. 61(10): p. 1298-1299. DOI:10.1021/np980128i.
31. Chobot, V., et al., Antifungal activity of a thiophene polyine from Leuzea carthamoides. 2003. 74(3): p. 288-290. DOI:10.1016/S0367-326X(03)00027-3.
32. Geszprych, A. and Weglarz, Z. Composition of essential oil from underground and aboveground organs of Rhaponticum carthamoides [Willd.] Iljin. 2002. 4(48).
33. Kokoska, L. and Janovska, D. Chemistry and pharmacology of Rhaponticum carthamoides: a review. 2009. 70(7): p. 842-855. DOI:10.1016/j.phytochem.2009.04.008.
34. Havlik, J., et al., Norsesquiterpene hydrocarbon, chemical composition and antimicrobial activity of Rhaponticum carthamoides root essential oil. 2009. 70(3): p. 414-418. DOI:10.1016/j.phytochem.2008.12.018.
35. Brekhman, I. and Dardymov, I. New substances of plant origin which increase nonspecific resistance. 1969. 9(1): p. 419-430. DOI:10.1146/annurev.pa.09.040169.002223.
36. Syrov, V. and Kurmukov, A. Anabolic activity of phytoecdysone-ecdysterone isolated from Rhaponticum carthamoides (Willd.) Iljin. 1976. 39(6): p. 690-693. PMID: 1030669.
37. Slama, K., et al., Insect hormones in vertebrates: anabolic effects of 20-hydroxyecdysone in Japanese quail. 1996. 52(7): p. 702-706. DOI:10.1007/BF01925578.
38. Gadzhieva, R., et al., A comparative study of the anabolic action of ecdysten, leveton and Prime Plus, preparations of plant origin. 1995. 58(5): p. 46-48. PMID: 8704590.
39. Syrov, V., et al., The effect of phytoecdisteroids on the bile secretion function of the liver in normal rats and in animals with experimental hepatitis. 1986. 49(3): p. 100-103. PMID: 3720929.
40. Plotnikov, M., et al., Effect of Rhaponticum carthamoides extract on hemorheological properties of blood in rats with arterial hypertension. 2001. 64(6): p. 45-47. PMID: 11871238.
41. Molokovskij, D., et al., Comparative estimation of antidiabetic activity of different adaptogenic vegetative preparations and extractions from plant material of some official medicinal plants. 2002. 38(4): p. 15-28.
42. Koleckar, V., et al., In vitro antiplatelet activity of flavonoids from Leuzea carthamoides. 2008. 31(1): p. 27-35. DOI:10.1080/01480540701688444.
43. Maĭmeskulova, L. and Maslov, L. Anti-arrhythmic effect of phytoadaptogens. 2000. 63(4): p. 29-31. PMID: 11022302.
44. Vershinina, S. On the effect of Leuzea carthamoides extract and sarcolysin on the course of lympholeukosis in NK-Ly mice. 1967. 13(5): p. 99-101. PMID: 5599271.
45. Kormosh, N., et al., Effect of a combination of extract from several plants on Cell‐mediated and humoral immunity of patients with advanced ovarian cancer. 2006. 20(5): p. 424-425. DOI:10.1002/ptr.1889.
46. Kokoska, L., et al., In Vitro. Antibacterial Activity of Four Leuzea. Species. 2005. 43(1): p. 8-11. DOI:10.1080/13880200590903237.
47. Osipova, S., et al., Ecdysten in the treatment of giardiasis. 2002(1): p. 29-33. PMID: 12224262.
48. Petkov, V., et al., Pharmacological investigations on Rhaponticum carthamoides. 1984. 50(03): p. 205-209. DOI: 10.1055/s-2007-969679.
49. Kosar, K., et al., Embryotoxicity of 20-hydroxyecdysone and poly-podine B from Leuzea carthamoides DC. 1997. 52(5): p. 406-407.
50. Chobot, V., et al., Phototoxic activity of a thiophene polyacetylene from Leuzea carthamoides. 2006. 77(3): p. 194-198. DOI:10.1016/j.fitote.2006.01.001.



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