New steroidal glycoside of allium cyrilіlii racemes

Authors

  • N. V. Tolkachova Nikitsky Botanical Garden - National Science Center, Ukraine
  • O. S. Shashkov Institute of Organic Chemistry named after. MD Zelinsky RAS, Russian Federation
  • V. Ya. Chyrva Taurian National University named after. VI Vernadsky, Ukraine

DOI:

https://doi.org/10.24959/ophcj.13.739

Keywords:

Allium cyrillii Ten. racemes, steroidal glycosides, combination of two-dimensional TOCSY and COSY spectra

Abstract

Steroidal glycosides are the vast class of natural compounds from the group of saponins that attract attention of researchers due to the wide spectrum of their biological activity and ecological safety. Plants from Allium genus growing in the Crimea are promising as to search of species with saponins. As a result of research of steroidal glycosides of Allium cyrillii Ten. racemes a new spirostanol glycoside has been isolated. The 1H- and 13C-NMR spectral data testify that this compound is a derivative of spirostan series. After acidic hydrolysis with the help of TLC only glucose has been identified by comparing to the samples of monosaccharides known beforehand. The chemical shifts of all protons of the carbohydrate residue have been determined by means of combination of two-dimensional TOCSY and COSY spectra. The 13C-chemical shifts of signals of their corresponding atoms are simply taken by means of the HSQC spectrum. The hydroxy groups position at C-2 and C-6 atoms of aglycone have been determined by the analysis of chemical shifts of C-atom signal comparing to the literary data for unsubstituted for aglycon parts and taking into account considerable positive α-effects of hydroxylation and little, usually negative, β-effects. Analysis of NMR 13C spectra of the compound isolated and 24 hydroxy derivative has shown that the signal of C-24 undergoes paramagnetic displacement in +10.8 ppm. The strong field change of signals of C-23 and C-25 also takes place. Correlation between the signal of the anomeric proton of glucose and C-24 aglycone in the HMBC spectrum confirms the site of addition of the glucose residue to aglycone. Thus, the glycoside isolated from Allium cyrillii racemes is (24S,25S)-5α-spirostan-2α,3β,6β,24-tetraol-24-O-β-D-glucopyranoside and it is a new compound.

Downloads

Download data is not yet available.

References

  1. Кинтя П.К., Лазурьевский Г.В., Балашова Н.Н. и др. Строение и биологическая активность стероидных гликозидов ряда спиростана и фуростана. – Кишинев: Штиинца, 1987. – 142 с.
  2. Васильева И.С., Пасешниченко В.А. // Прикладная биохим. и микробиол. – 1995. – Т. 31. – С. 238-242.
  3. Берсукер И.Б., Димогло А.С., Чобан И.Н. и др. // Хим.-фарм. журн. – 1983. – №12. – С. 1467-1471.
  4. Yang C.-R., Zhang Y., Jacob M.R. et al. // Antimicrobial Agents and Chemotherapy. – 2006. – Vol. 50, №5. – P. 1710-1714.
  5. Mskhiladze L., Legault J., Lavoie S. et al. // Molecules. – 2008. – Vol. 13. – P. 2925-2934.
  6. Oleszek W., Marston A. // Phytochemical Society of Europe. – 2000. – Vol. 45. – Р. 241-254.
  7. Кинтя П.К., Бурцева С.А., Ковальчук Л.П. и др. // Хим.-фарм. журн. – 1982. – №1. – С. 95-97.
  8. Sauvaire Y., Baissac Y., Leconte O. // Adv. in Exp. Med. and Biol. N.Y. – London: Plenum Press. – 1996. – Vol. 405. – P. 37-46.
  9. Васильева И.С., Удалова Ж.В., Зиновьева С.В., Пасешниченко В.А. // Прикладная биохим. и микробиол. – 2009. – Т. 45, №5. – С. 517-526.
  10. Толкачева Н.В., Шашков А.С., Чирва В.Я. // Химия природ. соедин. – 2012. – №2. – С. 243-246.
  11. Толкачева Н.В., Зайцев Г.П., Качала В.В. и др. // Ученые записки ТНУ, Серия «Биология, химия». – 2011. – Т. 24 (63), №2. – С. 390-395.
  12. Mimaki Y., Kuroda M., Fukasawa T., Sashida Y. // Chem. Pharm. Bull. – 1999. – Vol. 47. – Р. 738-743.
  13. Воллернер Ю.С., Кравец С.Д., Шашков А.С. и др. // Химия природ. соедин. – 1989. – №4. – С. 505-510.
  14. Morita T., Ushiroguchi T., Hayashi N. et al. // Chem. Pharm. Bull. – 1988. – Vol. 36. – P. 3480-3486.
  15. Воллернер Ю.С., Абдуллаев Н.Д., Горовиц М.Б., Абубакиров Н.К. // Химия природ. соедин. – 1983. – №6. – С. 736-740.
  16. Кравец С.Д., Воллернер Ю.С., Шашков А.С. и др. // Химия природ. соедин. – 1987. – №6. – С. 843-849.
  17. Воллернер Ю.С., Абдуллаев Н.Д., Горовиц М.Б., Абубакиров Н.К. // Химия природ. соедин. – 1984. – №1. – С. 69-73.
  18. Kawashima K., Mimaki Y., Sashida Y. // Phytochemistry. – 1991. – Vol. 30, №9. – Р. 3063-3067.
  19. Jiang Y., Wang N.-L., Yao X.-S., Kitanaka S. // Studies in Plant Sci. – 1999. – Vol. 6. – Р. 201-211.
  20. Kiyosawa S., Huton M. // Chem. Pharm. Bull. – 1968. – Vol. 16. – P. 1162-1164.
  21. Sannie M., Lapin H. // Bull. Soc. Chem. France. – 1957. –Vol. 10. – P. 1237-1241.

Downloads

Published

2013-09-10

How to Cite

(1)
Tolkachova, N. V.; Shashkov, O. S.; Chyrva, V. Y. New Steroidal Glycoside of Allium cyrilіlii Racemes. J. Org. Pharm. Chem. 2013, 11, 78-82.

Issue

Vol. 11 No. 3(43) (2013)

Section

Original Researches

License

Copyright (c) 2013 National University of Pharmacy

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Authors publishing their works in the Journal of Organic and Pharmaceutical Chemistry agree with the following terms:

1. Authors retain copyright and grant the journal the right of the first publication of the work under Creative Commons Attribution License allowing everyone to distribute and re-use the published material if proper citation of the original publication is given.

2. Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal’s published version of the work (e.g., post it to an institutional repository or publish it in a book) providing proper citation of the original publication.

3. Authors are permitted and encouraged to post their work online (e.g. in institutional repositories or on authors’ personal websites) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (see The Effect of Open Access).