COMPARATIVE STUDY OF THE SPECTRAL CHARACTERISTICS OF α-ARBUTIN AND β-ARBUTIN


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Abstract

The aim of this work is comparative study of the features of the spectral characteristics of α-arbutin and β-arbutin, isolated from the leaves of the bearberry [Arctostaphylos uva-ursi (L.) Spreng.] Arbutin is the main biologically active compound of the leaves of the bearberry [Arctostaphylos uva-ursi (L.) Spreng., the family Ericaceae], common cowberry (Vaccinium vitis-idaea L.), as well as in several other plants, causing the diuretic and anti-inflammatory properties of pharmaceuticals on the basis of the above raw materials. Arbutin is widely used in pharmaceutical analysis of the leaves of Arctostaphylos uva-ursi and Vaccinium vitis-idaea, as well as drugs based on this raw material as a standard substance. From the Arctostaphylos uva-ursi leaves there were isolated and characterized α-arbutin (1-O-α-D-glucopyranoside of hydroquinone and arbutin (1-O-β-D-glucopyranoside of hydroquinone) using the 1H-NMR-, 13C-NMR-, UV-spectroscopy and mass spectrometry. In the comparative plan the features of the spectral characteristics of α-arbutin and β-arbutin, and also their pentaacetates received as a result of acetylation by acetic anhydride in the presence of pyridine were studied. It was determined that for the identification of α-arbutin and β-arbutin the data of 1H-NMR-spectroscopy are of fundamental importance. The principal difference in the 1H-NMR spectra of α-arbutin and β-arbutin are the values of the coupling constant and the value of the chemical shift of the anomeric proton of glucose (C-11). In addition, in the 1H-NMR spectrum of α-arbutin there has the singlet signal of the proton of the phenolic OH-group at 9.02 ppm, whereas in the 1H-NMR spectrum of β-arbutin this signal is absent. Consequently, one of the most important characteristics in terms of assessing the authenticity and purity of arbutin as a standard sample are the results of 1H-NMR spectroscopy.

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About the authors

V. A Kurkin

Samara State Medical University

Email: Kurkinvladimir@yandex.ru
Dr.Sc. (Pharm.), Professor, Head of Department of Pharmacognosy with Botany and Basis of Phytotherapy

T. K Ryazanova

Samara State Medical University

Ph.D. (Pharm.), Associate Professor, Department of Economics of Pharmacy

A. V Kurkina

Samara State Medical University

Dr.Sc. (Pharm.), Associate Professor, Department of Pharmacognosy with Botany and Basis of Phytotherapy

S. V Pervushkin

Samara State Medical University

Dr.Sc. (Pharm.), Professor, Head of Department of Pharmaceutical Technology

I. K Petrukhina

Samara State Medical University

Dr.Sc. (Pharm.), Professor, Head of Department of Economics of Pharmacy

A. I Agapov

Samara State Medical University

Dr.Sc. (Biol.), Professor, Head of Department of Pharmaceutical Technology

References

  1. Государственная фармакопея СССР: Вып. 2. Общие методы анализа. Лекарственное растительное сырье, МЗ СССР. 11-е изд., доп. М.: Медицина. 1990.
  2. Государственная фармакопея Российской Федерации. XIV издание. Т. 4. М. 2018 / http://femb.ru/femb/pharmacopea.php.
  3. Куркин В.А. Фармакогнозия. Изд. 3-е, перераб. и доп. Самара: ООО «Офорт»; ФГБОУ ВО СамГМу Минздрава России. 2016. 1279 с.
  4. Растительные ресурсы СССР. Цветковые растения, их химический состав, использование. Семейства Paeonia-ceae - Thymelaeaceae, Л.: Наука. 1985. 336 с.
  5. Растительные ресурсы России: Дикорастущие цветковые растения, их компонентный состав и биологическая активность. Т. 2. Семейства Actinidiaceae - Malvaceae, Euphorbiaceae - Haloragaceae / Под ред. А.Л. Буданцева. СПб; М.: Товарищество научных изданий КМК. 2009. С. 24-26.
  6. Федосеева Л.М., Малолеткина Т.С. Выделение некоторых фенольных соединений и идентификация арбутина из листьев бадана // Химия растительного сырья. 1999. № 2. С. 109-111.
  7. Волобой Н.Л., Бутакова Л.Ю., Смирнов И.В. Изучение антимикробного действия арбутина и гидрохинона в отношении некоторых представителей грамотрицательной флоры // Химия растительного сырья. 2013. № 1. С. 179-182.
  8. Волобой Н.Л., Смирнов И.В., Бондарев А.А. Особенности мочегонной активности арбутина и гидрохинона // Сибирский медицинский журнал. 2012. Т. 27. № 3. С. 131-134.
  9. Gousiadou С., Li H-Q., Gotfredsen C.H., Jensen S.R. Iridoids in Hydrangeaceae // Biochemical Systematics and Ecology. 2016. № 64. P. 122-130.
  10. Chauharn R., Rubyk K., Dwivedi J. Secondary metabolites found in Bergenia species: a compendious review // International Journal of Pharmacy and Pharmaceutical Sciences. 2013. V. 5. № 1. Р. 9-16.
  11. Sohretoglu D., Sakar M.K., Sabuncuoglu S.A., Ozgunes H., Sterner O. Polyphenolic constituents and antioxidant potential of Geranium stepporum Davis // Rec. Nat. Prod. 2011. V. 5. № 1. P. 22-28.
  12. Могиленко Т.Г., Денисенко О.Н., Галяутдинов И.В. Методика получения арбутина из надземной части серпухи пятилистной (Serrulata quinquefolia Bild. ex Will), интродуцированной на Северном Кавказе // Журнал научных статей «Здоровье и образование в ХХ веке». 2016. Т. 18. № 8. С. 116-119.
  13. Куркин В.А., Рязанова Т.К., Платонов И.А., Павлова Л.В. Количественное определение арбутина в листьях толокнянки обыкновенной // Химия растительного сырья. 2015. № 1. С. 95-100.
  14. Куркин В.А., Рязанова Т.К., Платонов И.А., Павлова Л.В. Определение арбутина в листьях брусники обыкновенной // Химико-фармацевтический журнал. 2017. Т. 51. № 4. С. 34-37.
  15. Моисеев Д.В. Кинетики реакции деструкции арбутина в листьях брусники обыкновенной при хранении в естественных и стрессовых условиях // Краткий научно-практический вестник «Человек и его здоровье». 2013. № 2. С. 106-111.
  16. Ärok R., Végh K., Alberti À., Kéry À. Phytochemical comparison and analysis of Bergenia crassifolia L. (Fritsch.) and Bergenia cordifolia Sternb // Eur. Chem. Bull. 2012. V. 1. № 1-2. P. 31-34.
  17. Rychlinsk I., Nowak S. Quantitative Determination of Arbutin and Hydroquinone in Different Plant Materials by HPLC // Not. Bot. Hort. Agrobot. Cluj. 2012. V. 40. № 2. P. 109-113.
  18. Panusa A., Petrucci R., Marrosu G., Multari G., Gallo F.R. UHPLC-PDA-ESI-TOF/MS metabolic profiling of Arctostaphylos pungens and Arctostaphylos uva-ursi. A comparative study of phenolic compounds from leaf methanolic extracts // Phytochemistry. 2015. V. 115. № 1. P. 79-88.
  19. Cepanec I., Litvic M. Simple and efficient synthesis of arbutin // ARKIVOC. 2008 (ii). P. 19-24.
  20. Kwiecien I., Szopa A., Madej K. Ekiert H. Arbutin production via biotransformation of hydroquinone in vitro cultures of Aronia melanocarpa (Michx.) Elliott // Acta Bionorica Polonica. 2013. V. 60. № 4. P. 865-870.
  21. Bulduk I., §ahin M.D., §anli S. Arbutin analysis in leaves, fruit and branches of Pyrus anatolica, method optimization // Eurasian Journal of Analytical Chemistry. 2016. V. 1. № 5. P. 233-244.
  22. Choi Y.H., Sertic S., Kim H.K., Wilson E.G., Michopoulos F., Lefeber A. W.M., Erkelens C., Kricun S.D.P., Verpoorte R. Classification of Ilex Species Based on Metabolomic Fingerprinting Using Nuclear Magnetic Resonance and Multivariate Data Analysis // Journal of Agricultural and Food Chemistry. 2005. № 53. P. 1237-1245.
  23. Pop C., Vlase L., Tamas M. Natural resources containing arbutin. Determination of arbutin in the leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania // Not. Bot. Hort. Agrobot. Cluj. 2009. V. 37. № 1. P. 129-132.
  24. Huang S.-L., Zhu Yu-L., Pan Yu.-J., Wu S.-H. Synthesis of arbutin by two-step reaction from glucose // J. Zhejiang Univ. Sci. 2004. V. 5. № 12. P. 1509-1511.
  25. Suau R., Cuevas A., Alpuesta V., Reid M.S. Arbutin and sucrose in the leaves of the resurrection plant Myrothamnus flabellifolia // Phytochemistry. 1991. V. 30. № 8. P. 2555-2556.
  26. Das N.M., Mohan R., Parthipan B.P. Isolation, purification and characterization of arbutin from Cleidion nitidum (Muell. - Arg.) Thw. ex Kurz. (Euphorbiaceae) // International Journal of Science and Research. 2016. V. 5. № 1. P. 1549-1554.
  27. Sugimoto K., Nishimura T., Nomura K., Sugimoto K., Kuriki T. Syntheses of arbutin-a-glycosides and a comparison of their inhibitory effects with those of a-arbutin and arbutin on human tyrosinase // Chem. Pharm. Bull. 2003. V. 51. № 7. P. 798-801.
  28. Erenler R., Sen O., Aksit H., Demirtas I., Yaglioglu A.S., Elmastasa M., Telcic I. Isolation and identification of chemical constituents from Origanum majorana and investigation of antiproliferative and antioxidant activities // J. Sci Food Agric., wileyonlinelibrary.com. doi: 10.1002/jsfa.7155. 2015.

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