The determination of the phytochemical composition of the Altabor substance

Authors

  • S. Yu. Sheiko V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine, Ukraine
  • A. S. Shalamay PJSC SIC “Borshchahivskiy CPP”, Ukraine

DOI:

https://doi.org/10.24959/ophcj.21.202081

Keywords:

gallotannins; ellagitannins; Altabor; chemical composition; structure; HPLC (high-performance liquid chromatography)

Abstract

The development of medicines based on alder cone extracts led to the introduction of Altan and Altabor
medicines into medical practice. The technology of extraction cake from cones has made it possible to obtain extracts with different therapeutic properties.
Aim. To develop an effective method for studying the qualitative composition of the Altabor substance and
determine the quantitative content of its components.
Results and discussion. The Altabor substance is a complex mixture of ellagitannins containing more than 70 components. The main components of the extract (or their isomers) were determined by mass spectrometry and by comparing the retention times with the literature data. Gallic, ellagic, valoneic acids dilactone were conclusively determined by adding reference standards of these acids to the extract. The substance contains the following compounds: 2,3-hexahydroxydiphenoyl-(α/β)-glucose tr1 = 0.55 min, tr2 = 0.89 min (α and β isomers), 4,6-O-[(S)-valeonyl]-D-glucose (isomer) tr = 0.64 min, gallic acid tr = 1.198 min, pedunculagin tr1 = 3.63 min, tr2 = 4.62 min
(α and β isomers), proecoxin A (isomer) tr = 4.78 min, valoneic acid dilactone tr = 6.19 min, ellagic acid pentoside (isomer) tr = 7.07 min, ellagic acid tr = 7.335 min.
Experimental part. The composition analysis was performed using an Agilent 1200 chromatograph with a UV detector, a G6140 mass detector, an Alltech 3300 light scattering detector (ELSD), as well as the Agilent ChemStation Rev.B.04.03 software. The molecular weights of the compounds in the extract were determined using the method of mass spectrometry of ESI-electrospray ionization. The determination of the components was performed using an ultraviolet detector at a wavelength of 280 nm. The column was Rapid Resolution HT Cartige, 4.6 × 30 mm, 1.8 μm, Zorbax SB-C18.
Conclusions. A new effective method of analysis of the Altabor substance has been developed; it allows
determining the qualitative and quantitative content of its structural components. The method gives the possibility to control the process of obtaining the Altabor substance, study the dependence of its composition on the conditions of its obtaining, batch number, place, time of the natural raw material collection, and study the composition of other pharmaceutical substances, the plant raw material containing tannins. The advantage of the method is
the short time (up to 10 min) of analysis using high-performance liquid chromatography at high resolution.
Key words: gallotannins; ellagitannins; Altabor; chemical composition; structure; HPLC (high-performance liquid chromatography)

Downloads

Download data is not yet available.

References

  1. Екофлора України; Дідух, Я. П., Ред.; Фітосоціоцентр: Київ, 2004; Т. 2, 442 – 447.
  2. Задорожный, А. М.; Кошкин, А. Г.; Соколов, С. Я.; Шретер, А. И. Справочник по лекарственным растениям; Лесная промышленность: Москва, 1981.
  3. Рибалко, С. Л. Вивчення антивірусної активности препарату Альтабор на експериментальній моделі інфекції, спричиненої вірусом гепатиту С, в культурі клітин. Вісник фармакології та фармації 2010, 3, 29 – 36.
  4. Попова, О. І. Клінічна ефективність альтабору в комплексному лікуванні герпетичної інфекції порожнини рота. Український медичний альманах 2013, 16 (1), 154 – 56.
  5. Яковлєва, Л. В.; Євдокімова, О. С. Альтан – новий препарат для лікування виразкової хвороби шлунково-кишкового тракту. Вісник фармації 1993, 1-2, 96 – 103.
  6. Сербин, А. Г.; Яковлева, Л. В.; Хворост, О. П.; Гладух, Е. В.; Комиссаренко, Н. Ф.; Бондарь, В. С.; Болотов, В. В.; Шаламай, А. С. Альтан – новое отечественное эффективное средство ранозаживляющего, противовоспалительного, антимикробного действия. Провизор 1998, 18, 40 – 41.
  7. Бойчук, О. П. Застосування фітопрепарату “Альтан” в комплексному лікуванні хворих на гострі кишкові інфекції на тлі супутньої патології органів травлення. Галицький лікарський вісник 2004, 11 (2), 20 – 21.
  8. Незгода, І. І.; Рикало, Н. А. (Вінницький національний медичний університет ім. М. І. Пирогова). Спосіб лікування гострих кишкових інфекцій. Патент України 3317, 15.11.2004.
  9. Рикало, Н. А. Ефективність фітопрепарату «Альтан» при експериментальному клебсієльозі. Експериментальна і клінічна медицина 2005, 2, 41 – 44.
  10. Лапковський, Е. Й. Застосування альтану і дицетелу для корекції біохімічних та імунологічних показників при хронічному некаменевому холециститі. Клінічна та експериментальна патологія 2004, 4, 117 – 120.
  11. Зупанец, И. А.; Герасименко, Е. В.; Шаламай, А. С.; Саенко, Т. В. Опыт применения препарата Альтабор в профилактике гриппа и острых респираторных вирусных инфекций. Здоров’я України 2013, 20, 43 – 45.
  12. Ivanov, S. A.; Nomura, K.; Malfanov, I. L.; Ptitsyn, L. R. Glutinoin, a novel antioxidative ellagitannin from Alnus glutinosa cones with glutinoic acid dilactone moiety. Natural Product Research 2012, 26 (19), 1806 – 1816. https://doi.org/10.1080/14786419.2011.613387.
  13. Кrutskikh, Т. V.; Shalamay, А. S. Validation of the method of quantitative determination of the amount elagotannins in tablets Altabor. Management, economy and quality assurance in pharmacy 2015, 3, 25 – 29.
  14. Gryszczyńska, A.; Dreger, M.; Piasecka, A.; Kachlicki, P.; Witaszak, N.; Sawikowska, A.; Ożarowski, M.; Opala, B.; Łowicki, Z.; Pietrowiak, A.; Miklaś, M.; Mikołajczak Przemysław, Ł.; Wielgus, K. Qualitative and quantitative analyses of bioactive compounds from ex vitro Chamaenerion angustifolium (L.) (Epilobium augustifolium) herb in different harvest times. Industrial Crops and Products 2018, 123, 208 – 220. https://doi.org/10.1016/j.indcrop.2018.06.010.
  15. Liang, X.; Jiang, Y.; Guo, Z.; Fang, S. Separation, UPLC-QTOF-MS/MS analysis, and antioxidant activity of hydrolyzable tannins from water caltrop (Trapa quadrispinosa) pericarps. LWT 2020, 133, 110010. https://doi.org/10.1016/j.lwt.2020.110010.
  16. Grace, M. H.; Warlick, C. W.; Neff, S. A.; Lila, M. A. Efficient preparative isolation and identification of walnut bioactive components using high-speed counter-current chromatography and LC-ESI-IT-TOF-MS. Food Chem. 2014, 158, 229 – 238. https://doi.org/10.1016/j.foodchem.2014.02.117.
  17. Regueiro, J.; Sánchez-González, C.; Vallverdú-Queralt, A.; Simal-Gándara, J.; Lamuela-Raventós, R.; Izquierdo-Pulido, M. Comprehensive identification of walnut polyphenols by liquid chromatography coupled to linear ion trap–Orbitrap mass spectrometry. Food Chem. 2014, 152, 340 – 348. https://doi.org/10.1016/j.foodchem.2013.11.158.
  18. Jia, X.; Luo, H.; Xu, M.; Zhai, M.; Guo, Z.; Qiao, Y.; Wang, L. Dynamic Changes in Phenolics and Antioxidant Capacity during Pecan (Carya illinoinensis) Kernel Ripening and Its Phenolics Profiles. Molecules 2018, 23 (2), 435. https://doi.org/10.3390/molecules23020435.

Downloads

Published

2021-03-15

How to Cite

(1)
Sheiko, S. Y.; Shalamay, A. S. The Determination of the Phytochemical Composition of the Altabor Substance. J. Org. Pharm. Chem. 2021, 19, 16-24.

Issue

Vol. 19 No. 1(73) (2021)

Section

Original Researches

License

Copyright (c) 2021 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).