DROUGHT INFLUENCE ON THE CONTENT AND COMPOSITION OF ALKALOIDS FROM SEEDS OF THE CHAMAECYTISUS RUTHENICUS (FISCH. EX WOLOSZCZ.) KLASKOVA, GROWING AT THE MOUNTAIN-FORESTS ZONE OF SOUTHERN URALS

  • Инна (Inna) Петровна (Petrovna) Цыпышева (Tsypysheva) Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences http://orcid.org/0000-0002-5025-8742 Email: tsipisheva@anrb.ru
  • Евгений (Evgeniy) Григорьевич (Grigor'yevich) Галкин (Galkin) Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences Email: spectr@anrb.ru
  • Полина (Polina) Радиковна (Radikovna) Петрова (Petrova) Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences Email: tsipisheva@anrb.ru
  • Алена (Alena) Витальевна (Vital'yevna) Ковальская (Koval’skaya) Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences Email: tsipisheva@anrb.ru
  • Николай (Nikolay) Иванович (Ivanovich) Федоров (Fedorov) Ufa Institute of Biology of the Ufa Research Centre of Russian Academy of Sciences Email: fedorov@anrb.ru
Keywords: Chamaecytisus ruthenicus, quinolizidine alkaloids, sparteine, methylcytisine, d-lupanine, salsolidine, ammodemdrine, GC/MS

Abstract

Quinolizidine alkaloid content of the Chamaecytisus ruthenicus (Fabaceae) seeds, collected in the period of drought in 2010 and in 2011 (last was normal in the number of precipitation), was determined by the chromato-mass-spectrometry method. Total sums of alkaloids from the seeds of Chamaecytisus ruthenicus were isolated in two stages. The first stage included preliminary "degreasing" of crushed seeds with hexane. Then resulting hexane extract was washed with aqueous solution of 3% hydrochloric acid, and acidic layer was treated by anhydrous Na2CO3 until pH 9. Alkaloids (in the form of bases) were extracted with chloroform. In parallel, the seeds are previously washed with hexane were thoroughly extracted with an acetone-water mixture (1 : 9), and then resulting water-acetone extract has been treated in accordance with the traditional method. Alkaloids obtained from hexane extract and fatless seeds were combined, concentrated and analyzed by chromato-mass spectrometry method. Individual alkaloids were identified by their full mass spectra using d-lupanine as a standard. On the base on obtained results, it was found that in drought conditions of 2010 the content of alkaloids in seeds of the Russian Broom (Ch. Ruthenicus) is significantly lower than in 2011, typical for its weather conditions (0.81% vs. 3.2%). However, the composition of alkaloids in the seeds of the Ch. ruthenicus, collected during the drought period, was more various: sparteine, methylcytisine, 17-oxosparteine, sophocarpine, d-lupanine, isoquinoline alkaloid salsolidine and pyridine alkaloid ammodendrine were found in these seeds. Only four quinolizidine alkaloids – sparteine, d-lupanine, 17-oxosparteine and sophocarpine were isolated from the seeds of Ch. ruthenicus 2011.

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Author Biographies

Инна (Inna) Петровна (Petrovna) Цыпышева (Tsypysheva), Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences

кандидат химических наук, старший научный сотрудник лаборатории биоорганической химии и катализа

Евгений (Evgeniy) Григорьевич (Grigor'yevich) Галкин (Galkin), Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences

кандидат химических наук, старший научный сотрудник лаборатории ФХМА

Полина (Polina) Радиковна (Radikovna) Петрова (Petrova), Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences

младший научный сотрудник лаборатории биоорганической химии и катализа

Алена (Alena) Витальевна (Vital'yevna) Ковальская (Koval’skaya), Ufa Institute of Chemistry of the Ufa Research Centre of Russian Academy of Sciences

кандидат химических наук, научный сотрудник лаборатории биоорганической химии и катализа

Николай (Nikolay) Иванович (Ivanovich) Федоров (Fedorov), Ufa Institute of Biology of the Ufa Research Centre of Russian Academy of Sciences

доктор биологических наук, заведующий лабораторией экологии растительных ресурсов

References

Соколов В. С. Алкалоидоносные растения СССР. Москва, Ленинград, Изд-во АН СССР, 1952. 380 с.

Орехов А. П. Химия алкалоидов. 2-е изд. Москва, Изд-во АН СССР, 1955. 865 с.

Алкалоиды / под ред. С. Ю. Юнусова. 3-е изд. Ташкент, Фан, 1981. 418 с.

Aniszewski T. Alkaloids Chemistry, Biology, Ecology, and Applications. 2nd Edition. Elsevier Science, 2015. 496 p.

Кузнецова М. А. Лекарственное растительное сырье и препараты. Москва, Высшая школа, 1987. 191 с.

Правила сбора и сушки растительного сырья / под ред А. И. Шретера. Москва, Медицина, 1985. 328 с.

Selmar D., Kleinwächter M. Stress Enhances the Synthesis of Secondary Plant Products: The Impact of Stress-Related Over-Reduction on the Accumulation of Natural Products // Plant and Cell Physiology. 2013. V. 54. P. 817–826. doi.org/10.1093/pcp/pct054.

Borges C. V., Minatel I. O., Gomez-Gomez H. A., Lima G. P. P. Medicinal Plants: Influence of Environmental Factors on the Content of Secondary Metabolites. // Medicinal Plants and Environmental Challenges. Springer, Cham, 2017. P. 259-277. doi.org/10.1007/978-3-319-68717-9_15.

Wink M., Meißner C., Witte L. Patterns of quinolizidine alkaloids in 56 species of the genus Lupinus // Phytochemistry. 1995. V. 38. P. 139–153. doi.org/10.1016/0031-9422(95)91890-D.

Saito K., Murakoshi I. Chemistry, biochemistry and chemotaxonomy of lupine alkaloids in the Leguminosae // Studies in Natural Products Chemistry. 1995. V. 15. P. 519-549. doi.org/10.1016/S1572-5995(06)80142-0.

Joseph P. M. Quinoline, quinazoline and acridone alkaloids // Natural Product Reports. 2007. V. 24. P. 191-222. dx.doi.org/10.1039/B509525P.

Lee M. J., Pate J. S., Harris D. J., Atkins C. A. Synthesis, transport and accumulation of quinolizidine alkaloids in Lupinus albus L. and L. angustifolius L. // Journal of Experimental Botany. 2007. V. 58. P. 935–946, doi.org/10.1093/jxb/erl254.

Bunsupa S., Yamazaki M., Saito K. Lysine-derived alkaloids: overview and update on biosynthesis and medicinal applications with emphasis on quinolizidine alkaloids // Mini-Reviews in Medicinal Chemistry. 2017. V. 17. P. 1002-1012. doi:10.2174/1389557516666160506151213

Perez E. G., Mendez-Galvez C., Cassels B. K. Cytisine: a natural product lead for the development of drugs acting at nicotinic acetylcholine receptors // Natural Product Reports. 2012. V. 29. P. 555-567, dx.doi.org/10.1039/C2NP00100D.

Rouden J., Lasne M.-C., Blanchet J., Baudoux J. (−)-Cytisine and derivatives: synthesis, reactivity, and applications // Chemical Reviews. 2014. V. 114. P. 712-778. DOI: 10.1021/cr400307e.

Tsypysheva I. P., Koval’skaya A. V., Lobov A. N., Makara N. S., Petrova P. R., Farafontova E. I., Zainullina L. F., Vakhitova Yu. V., Zarudii F. S. Synthesis and Nootropic Activity of new 3-Amino-12-N-Methylcytisine Derivatives // Сhemistry of Natural Compounds. 2015. V. 51. P. 910-915. doi.org/10.1007/s10600-015-1446-x

Makara N. S., Sapozhnikova T. A., Khisamutdinova R. Yu., Tsypysheva I. P., Borisevich S. S., Kovalskaya A. V., Petrova P. R., Khursan C. L., Zarudii F. S. Nootropic activity of a novel (-)-cytisine derivative (3aR,4S,8S,12R, 12aS,12bR)-10-methyl-2-phenyloctahydro-1H-4,12a-etheno-8,12-methanopyrrolo[3’,4’:3,4]pyrido[1,2-a][1,5]diazocine-1,3,5(4H)-trione // Bulletin of Experimental Biology and Medicine. 2018. V. 164. P. 434-438, doi.org/10.1007/s10517-018-4006-0.

Цыпышева И. П., Галкин Е. Г., Ерастов А. С., Каримова О. А., Байкова И. П., Рахимов Р. Г., Ковальская А. В., Халилова И. У., Абрамова Л. М., Юнусов М. С. Растительные источники хинолизидиновых алкалоидов на территории Республики Башкортостан I. Алкалоиды Thermopsis schischkinii и Thermopsis lanceolata ssp. Sibirica (Fabaceae) в условиях интродукции // Химия растительного сырья. 2012. № 4. С. 101–106.

Цыпышева И. П., Галкин Е. Г., Ерастов А. С., Каримова О. А., Байкова И. П., Ковальская А. В., Халилова И. У., Абрамова Л. М. Юнусов М. С. Растительные источники хинолизидиновых алкалоидов на территории Республики Башкортостан. II. Алкалоиды Thermopsis schischkinii // Химия растительного сырья. 2013. № 4. C. 55-60. dx.doi.org/10.14258/jcprm.1304055.

Tsypysheva I. P., Petrova P. R., Baykova I. P., Galkin E. G., Fedorov N. I., Galin F. Z., Yunusov M. S. Seasonal dynamics of alkaloids of Genista tinctoria L. growing at the Southern Ural region // Natural products: an Indian Journal. 2015. V. 10. P. 215-218.

Цыпышева И. П., Галкин Е. Г., Петрова П. Р., Байкова И. П., Галин Ф. З., Федоров Н. И. Сезонная динамика алкалоидов Chamaecytisus ruthenicus, произрастающего на Южном Урале // Химия растительного сырья. 2015. № 3. C. 65–69, dx.doi.org/10.14258/jcprm.201503765.

Цыпышева И. П., Галкин Е. Г., Петрова П. Р., Ковальская А. В., Байкова И. П., Галин Ф. З., Федоров Н. И. Экологические и внутривидовые особенности состава и содержания алкалоидов в надземной части Chamaecytisus ruthenicus (Fisch. ex Woloszcz.) Klaskova, произрастающего На Южном Урале // Химия растительного сырья. 2017. № 1. С. 93-97, dx.doi.org/10.14258/jcprm.2017011268.

Губанов И. А., Киселёва К. В., Новиков В. С., Тихомиров В. Н. Иллюстрированный определитель растений Средней России. Т. 2. Покрытосеменные (двудольные: раздельнолепестные). 2-е изд. Москва, товарищество научных изданий КМК, 2003. 665 с.

Жигунова С. Н., Федоров Н. И., Михайленко О. И. Распространение и сырьевая продуктивность Chamaecytisus ruthenicus (Fabaceae) в растительных сообществах республики Башкортостан // Растительные ресурсы. 2013. Т. 49. С. 353-359.

https://rp5.ru/Архив_погоды_в_Катав-Ивановске

Минина С. А., Каухова И. Е. Химия и технология фитопрепаратов. Москва, ГОЭТАР-Медиа, 2009. 560 с.

National Institute of Standards and Thecnology (http://www.nist.gov)

Amirjani M. R. Effects of drought stress on the alkaloid contents and growth parameters of Catharanthus roseus // ARPN Journal of Agricultural and Biological Science. 2013. V. 8, № 11. P. 745-750

Kleinwächter M., Selmar D. New insights explain that drought stress enhances the quality of spice and medicinal plants: potential applications // Agronomy for Sustainable Development. 2015. V. 35. P. 121-131. doi.org/10.1007/s13593-014-0260-3.

Frick K. M., Kamphuis L G., Siddique K. H. M., Singh K. B., Foley R. C. Quinolizidine Alkaloid Biosynthesis in Lupins and Prospects for Grain Quality Improvement // Frontiers in Plant Science. 2017. V. 8. P. 87. doi:10.3389/fpls.2017.00087

Christiansen J. L., Jørnsgard B., Buskov S., Olsen C. E. Effect of drought stress on content and composition of seed alkaloids in narrow-leafed lupin, Lupinus angustifolius L. // European Journal of Agronomy. 1997. V. 7. P. 307–314. doi:10.1016/S1161- 0301(97)00017-8.

Jansen G., Jurgens H.-U., Ordon F. Effects of Temperature on the Alkaloid Content of Seeds of Lupinus angustifolius Cultivars // Journal of Agronomy and Crop Science. 2009. V. 195. P. 172–177. doi.org/10.1111/j.1439-037X.2008.00356.x.

Wink M. Evolution of secondary metabolites in Legumes (Fabaceae) // South African Journal of Botany. 2013. V. 89. P. 164–175. doi.org/10.1016/j.sajb.2013.06.006.

Ракитник русский Chamaecytisus ruthenicus
Published
2018-12-11
How to Cite
1. Цыпышева (Tsypysheva)И. (Inna) П. (Petrovna), Галкин (Galkin)Е. (Evgeniy) Г. (Grigor’yevich), Петрова (Petrova)П. (Polina) Р. (Radikovna), Ковальская (Koval’skaya)А. (Alena) В. (Vital’yevna), Федоров (Fedorov)Н. (Nikolay) И. (Ivanovich) DROUGHT INFLUENCE ON THE CONTENT AND COMPOSITION OF ALKALOIDS FROM SEEDS OF THE CHAMAECYTISUS RUTHENICUS (FISCH. EX WOLOSZCZ.) KLASKOVA, GROWING AT THE MOUNTAIN-FORESTS ZONE OF SOUTHERN URALS // chemistry of plant raw material, 2018. № 4. P. 169-176. URL: http://journal.asu.ru/cw/article/view/4016.
Section
Low-molecular weight compounds