TRITERPENE GLYCOSIDE FROM THE PLANT CORTUSA MATTHIOLI L.

UDC 547.918:547.022

  • Igor' Vasil'yevich Beshley Institute of Biology, Komi Scientific Center, Ural Branch of RAS Email: beshley@ib.komisc.ru
  • Tat'yana Ivanovna Shirshova Institute of Biology, Komi Scientific Center, Ural Branch of RAS Email: shirshova@ib.komisc.ru
  • Vladimir Vital'yevich Volodin Institute of Biology, Komi Scientific Center, Ural Branch of RAS Email: volodin@ib.komisc.ru
  • Kirill Gennad'yevich Ufimtsev Institute of Biology, Komi Scientific Center, Ural Branch of RAS Email: ufimtsev@ib.komisc.ru
  • Natal'ya Georgiyevna Kolotyrkina Institute of Organic Chemistry named after N.D. Zelinsky RAS Email: nkolotyr@gmail.com
  • Igor' Nikolayevich Alekseev Institute of Chemistry, Komi Scientific Center, Ural Branch of RAS Email: alex_igor@list.ru
  • Sergey Aleksandrovich Patov Institute of Chemistry, Komi Scientific Center, Ural Branch of RAS Email: ser-patov@yandex.ru
Keywords: Cortusa matthioli L., triterpene glycosides, cyclamiretin A, IR, NMR spectroscopy, high resolution mass spectrometry

Abstract

Some representatives of the Primulaceae family consider to a promising sources of saponins. It is established that some species of this family contain significant concentrations of triterpene glycosides having interesting biological. According to the literature, in plants Cortusa turkestanica Losinsk. both steroid and triterpene glycosides were found, the content of which is 7.3%, and the hemolytic index reaches 25.000. The only representative of the genus Cortusa in the flora of the Komi Republic is Cortusa matthioli L. It is a boreal Eurasian species that grows almost everywhere in the forest zone of the Republic. From the aboveground part of the plant C. mattioli, collected in the vicinity of Syktyvkar in the flowering phase, by we for the first time were isolated triterpene glycoside pentacyclic series with gross formula C52H84O22. Using spectral methods (IR, NMR spectroscopy and high resolution mass spectrometry), the compound was identified as β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl-(1→4)-[β-D-glucopyranosyl-(1→2)]-α-L-arabinopyranosyl-(1→3)-13β, 28-epoxyolean-30-al-3β, 16α-diol. Previously this compound, for which cytotoxic activity against human colon cancer cells, uterine sarcoma and human melanoma was detected, was found in plants of Ardisia crispa, Myrsine pellucida, Androsace saxifragifolia, as well as some species of the genus Cyclamen.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

Author Biographies

Igor' Vasil'yevich Beshley, Institute of Biology, Komi Scientific Center, Ural Branch of RAS

научный сотрудник лаборатории биохимии и биотехнологии, кандидат биологических наук

Tat'yana Ivanovna Shirshova, Institute of Biology, Komi Scientific Center, Ural Branch of RAS

ведущий научный сотрудник лаборатории биохимии и биотехнологии, кандидат химических наук

Vladimir Vital'yevich Volodin, Institute of Biology, Komi Scientific Center, Ural Branch of RAS

заведующий лабораторией биохимии и биотехнологии, доктор биологических наук

Kirill Gennad'yevich Ufimtsev, Institute of Biology, Komi Scientific Center, Ural Branch of RAS

научный сотрудник лаборатории биохимии и биотехнологии, кандидат биологических наук

Natal'ya Georgiyevna Kolotyrkina, Institute of Organic Chemistry named after N.D. Zelinsky RAS

старший научный сотрудник отдела структурных исследований, кандидат химических наук

Igor' Nikolayevich Alekseev, Institute of Chemistry, Komi Scientific Center, Ural Branch of RAS

научный сотрудник лаборатории физико-химических методов исследования

Sergey Aleksandrovich Patov, Institute of Chemistry, Komi Scientific Center, Ural Branch of RAS

научный сотрудник лаборатории физико-химических методов исследования,  кандидат химических наук

References

Kintya P.K., Lazur'yevskiy G.V., Balashova N.N., Balashova I.T., Suruzhiu A.I., Lyakh V.A. Stroyeniye i biolog-icheskaya aktivnost' steroidnykh glikozidov ryada spirostana i furostana. [The structure and biological activity of ster-oid glycosides of a number of spirostan and furostan]. Kishinev, 1987, 142 p. (in Russ.).

Vasil'yeva I.S., Paseshnichenko V.A. Prikladnaya biokhimiya i mikrobiologiya, 1999, vol. 35, no. 5, pp. 521–535. (in Russ.).

Rastitel'nyye resursy SSSR: Tsvetkovyye rasteniya, ikh khimicheskiy sostav, ispol'zovaniye; Semeystva Paeoniaceae – Thymelaeaceae. [Plant resources of the USSR: Flowering plants, their chemical composition, use; Families Paeoniaceae – Thymelaeaceae]. Leningrad, 1986, vol. 2, 336 p. (in Russ.).

Asilbekova D.T., Nuriddinov KH.R. Khimiya rastitel'nogo syr'ya, 2011, no. 4, pp. 219–222. (in Russ.).

Flora severo-vostoka yevropeyskoy chasti SSSR. Semeystva Umbelliferae – Compositae. [Flora of the north-east of the European part of the USSR. Families Umbelliferae – Compositae]. Leningrad, 1977, vol. 4, 312 p. (in Russ.).

Beshley I.V., Ufimtsev K.G., Volodin V.V., Shirshova T.I. Rastitel'nyye resursy, 2018, vol. 54, no. 4, pp. 532–541, DOI: 10.1134/S0033994618040040. (in Russ.).

Tsedilin A.M., Fakhrutdinov A.N., Eremin D.V., Zalesskiy S.S., Kolotyrkina N.G., Ananikov V.P. Med. Comm., 2015, vol. 25, no. 11, pp. 454–456, DOI: 10.1016/j.mencom.2015.11.019.

Waltho J.P., Williams D.H., Mahato S.B., Pal B.C., Barna J.C.J. J. Chem. Soc. Perkin Trans., 1986, vol. 8, no. 1, pp. 1527–1531, DOI: 10.1039/P1986000152.

Ding Z., He Y., Ding J. Acta Bot. Yunnanica, 1993, vol. 15, no. 2, pp. 201–204.

Zhang X., Peng S., Wang M., Ding L. Acta. Pharm. Sinica, 1999, vol. 34, no. 11, pp. 838–840.

Liang B., Zhang L., Tian J., Xu L., Yang S. Carbohydrate Research, 2006, vol. 341, no. 14, pp. 2444–2448, DOI: 10.1016/j.carres.2006.06.020.

Altunkeyik H., Gülcemal D., Masullo M., Alankus-Caliskan O., Piacente S., Karayildirim T. Phytochemistry, 2012, vol. 73, pp. 127–133, DOI: 10.1016/j.phytochem.2011.09.003.

Podolak I., Koczurkiewicz P., Galanty A., Michalik M. Biochemical Systematics and Ecology, 2013, vol. 47, pp. 116–120, DOI: 10.1016/j.carres.2013.04.005.

Lavaud C., Massiot G., Barrera G.B., Moretti Ch., Le Men-Oliver L. Phytochemistry, 1994, vol. 37, no. 6, pp. 1671–1677, DOI: 10.1016/S0031-9422(00)89590-4.

Reznicek G., Jorenitsch J., Robien W., Kubelka W. Phytochemistry, 1989, vol. 28, no. 3, pp. 825–828, DOI: 10.1016/0031-9422(89)80123-2.

Jansakul C., Baumann H., Kenne L., Samuelsson G. Planta Med., 1987, vol. 53, pp. 405–409.

Park J.H., Kwak J.H., Khoo J.H., Park S.-H., Kim D.U., Ha D.M., Choi S.U., Kang S.C., Zee O.P. Arch Pharm Res., 2010, vol. 33, no. 8, pp. 1175–1180, DOI: 10.1007/s12272-010-0807-z.

Zhang D.M., Wang Y., Tang M.K., Chan Y.W., Lam H.M., Ye W.C., Fung K.P. Biochem. Biophys. Res. Commun., 2007, vol. 362, pp. 759–765.

Published
2019-12-27
How to Cite
1. Beshley I. V., Shirshova T. I., Volodin V. V., Ufimtsev K. G., Kolotyrkina N. G., Alekseev I. N., Patov S. A. TRITERPENE GLYCOSIDE FROM THE PLANT CORTUSA MATTHIOLI L. // chemistry of plant raw material, 2019. № 4. P. 243-248. URL: http://journal.asu.ru/cw/article/view/5133.
Section
Low-molecular weight compounds