CC BY
22комплексного лшування гострих кишкових шфек-цш вiрусноi етюлогп у дней. Соцiальна фармацiя в охоронi здоров'я. 2017. Т. 3, № 2. С. 70-79. [Electronic resource]. URL:
http://nbuv.gov.ua/UJRN/sphhc 2017_3_2_11. (last accessed 19.09.2018). (in Ukrainian).
5. Немченко А. С., Косяченко К. Л., Немче-нко О. А. Цшоутворення на лжарсьш засоби: моно-графiя (2-ге вид., доп. та перероб.). Х. : Вид-во ФОП Вировець А. П. Видавнича група «Апостроф». 2012. 304 с. (in Ukrainian).
6. Косяченко К. Л., Немченко А. С., Коваленко О. В. Науково-методичш пвдходи до оцшки ефективносп системи цш на лiкарськi засоби. Вю-ник фармацii. 2010. № 3. С. 51-54. (in Ukrainian).
7. Кухтенко О. С., Назаршна В. М., Гладух £.
B. Фармакоекономiчна оцiнка доступностi лтарсь-ких засобiв для лiкування захворювань дихальних шляхiв. Фармацевтичний часопис. 2017. № 3.
C.105-Ш. (in Ukrainian).
UDC 577.115.3:581.192:581.47:615.322:582.971.1
FATTY ACIDS IN THE COMPONENTS OF VIBURNUM OPULUS FRUIT
Leontiiev B.,
Student
National University of Pharmacy, Kharkov, Ukraine
Khvorost O.,
Doctor of Pharmacy (Dr. habil.), professor of the Department of Chemistry of Natural Compounds,
National University of Pharmacy, Kharkov, Ukraine
Fedchenkova Yu.
Doctor of Pharmacy (Dr. habil.), professor of the Department of Chemistry and Pharmacy
Nizhyn Mykola Gogol State University, Nezhin, Ukraine
Abstract
Aim. To study the composition of fatty acids of the components of Viburnum opulus fruit collected in Ukraine. The object of the study was fatty acids obtained in the kernel and the pericarp of domestic Viburnum opulus fruit. The study of fatty acids was performed by GC/MC.
Eight fatty acids in the kernel and 14 fatty acids in the pericarp have been identified, among of them 8 acids are common. Oleinic and linoleic acids (each - approximately 50 % from the total amount of fatty acids and about 30 % from the amount of fatty acids, respectively) were found in significant amounts in the kernel and in the pericarp. These compounds are of interest in pharmacy and medicine as components with the anti-inflammatory, energetic and plastic activity.
Conclusions. The qualitative composition of fatty acids in the kernel and the pericarp of domestic Viburnum opulus fruits has been studied. The results obtained indicate the prospects of creating new drugs based on the biologically active complex Omega-9 containing in the kernel and the pericarp of Viburnum opulus fruit.
Keywords: Viburnum opulus; GC; fruits; fatty acids
Recently the popularity of unsaturated fatty acids has grown steadily in medicine [1, p. 75, 2, p. 6849, 3 p. 1445]. Depending on the location of double bonds in the fatty acid molecule there are three families of these compounds. Calculations start from the methyl group at the end of the fatty acid chain. These are polyunsaturated fatty acids named Omega-3, Omega-6 and Omega-9. First of all, Omega-3 polyunsaturated fatty acids are promising to use, primarily hexadecatrienoic and eicosapentaenoic acid in the prevention of premature aging and the treatment of chronic obstructive pulmonary disease [1, p. 75]. Compounds of this class of biologically active substances (BAS) are effective in promoting growth, treating coronary heart disease, arrhythmias, cardiomyopathy, and dyslipidemia. Representatives of Omega-6 polyunsaturated acids - y-linolenic and arachidonic acids - play the same role as Omega-3 in the normal growth, but they have a better effect for the skin and the kidney function. However, the representatives of Omega-6 fatty acids under the action of some enzymes give rise to inflammatory substances - eicosanoids: prostaglandins, thromboxanes, prostacyclins and leukotrienes. Omega-3 forms eico-sanoids much slower, and their role in formation of inflammation is less. When it has been known that Omega-6 eicosanoid thromboxane affects platelet
sticking, and leukotrienes play an important role in the immune-inflammatory response of the body in arthritis, lupus erythematosus, asthma and infectious diseases, this competitive effect of Omega-3 and Omega-6 acquires particular importance. The most effective way of reducing the synthesis of Omega-6 eicosanoids is to consume more Omega-3 polyunsaturated fatty acids for the optimal ratio of Omega-3: Omega-6 - 1 : 2. In the human body the Omega-9 complex, which main component is monounsaturated oleic acid, has anti-inflammatory, energy and plastic properties. Humans do not need Omega-9 so much due to its synthesis in the body. However, the most important factors are the ratio of Omega-3 and Omega-6, as well as the intensity of the synthesis of Omega-9 [1, p. 75]. Therefore, obtaining a representative of the Omega-9 family - oleic acid from external sources is relevant. Recently, the popularity of studying lipid-containing the raw material has increased [4, p. 113, 5, p. 101, 6, , p. 128, 7, p. 711, 8, p. 260].
Viburnum opulus is a common bush of the domestic flora, one of the representatives of the genus Viburnum and family Caprifoliaceae. It is found in wild and cultivated state. The bark of Viburnum is the pharma-copoeial type of the raw material and has the hemostatic activity [9, p. 360]. The fruits of Viburnum opulus are
juicy drupe kernels, most often of a red or orange color. The exocarp (peel) is leathery dense translucent colored. The mesocarp (pulp) consists of large juicy cells. The endocarp with seed (kernel) is flat, round or heart-shaped, yellowish or pinkish. The studies on seeds of Viburnum opulus are known [10-15]. Most likely, the object of research in these works were kernels of the drupe (the endocarp with the seed enclosed in it), but not the seeds themselves. Thus, the effects of frost on the lipid composition of Viburnum opulus seeds [10, p. 636], changes in indicators (moisture content, fatty oil content, peroxide and acid numbers, protein content) in the crushed seeds of this plant during storage [11, p. 423], changes in the qualitative composition of lipids and substances of lipophilic nature in the process of fruit ripening were studied [12, p. 245]. The study of the fatty acid composition of seed lipids showed the fatty acid predominance in the ratio of 18 : 2 [13, p. 560]. However, there is no information found about the study of the fatty acid composition of the domestic raw material in the available literature. Therefore, the study of the qualitative composition of fatty acids in the components of Viburnum opulus fruits: the pericarp (exo-and mezocarp) and kernels (endocarp with seed), is of undoubted interest.
The aim of this work was to study the composition of fatty acids of the components of Viburnum opulus fruit collected in Ukraine.
Materials and methods
The fruits of Viburnum opulus were collected in September 2017 in the Chuguev district of the Kharkiv region on the edge of a pine forest. The raw material was ried in a SATURN ST-FP0114 dryer to an air-dry state at a temperature of 50-60 °C. The kernel was separated from the rest of the fruit. The raw material was crushed to a particle size of 2-3 mm.
Lipophilic fractions were obtained by exhaustive extraction with hexane. Methyl esters of fatty acids were formed during the hydrolysis. The method of gas chromatography and a "Selmichrom-1" with a flame-ionization detector were used. The gas chromatographic column made of a stainless steel was 2.5 m in diameter and 4 mm in the internal diameter, the stationary phase was inerton treated with 10 % diethylene gly-col succinate (DEGS).
The working conditions were as follows: the temperature of the column thermostat - 180 °C, the temperature of a desiccator - 230 °C, the temperature of a
detector - 220 °C, the flow rate of the gas carrier (nitrogen) - 30 cm3/min, the sample volume - 2 mm3 of the solution of acid methyl ester in hexane.
Identification of methyl esters of fatty acids were per-formed by the retention time of compounds compared to the retention time of a standard mixture (reference standards for saturated and unsaturated fatty acid methyl esters by Sigma). The composition of methyl esters was calculated by the method of internal normalization. Methyl esters of fatty acids were obtained by the modified Peisker method [16, p. 272], which provided full methylation of fatty acids. For methylation 30-50 mkl of the lipophilic fraction were measured in glass ampoules, 2.5 ml of a reaction mixture was added (a mixture of chloroform with methanol and sulfuric acid in the ratio of 100 : 100 : 1). The ampoules were sealed and placed in a thermostat at a temperature of 105 °C for 3 hours. After completion of methylation the ampoules were opened, their contents were transferred to a test tube, 0.2 g of a zinc sulphate powder, 2 ml of purified water and 2 ml of hexane were added for extraction of methyl esters. After careful shaking and settling the hexane extract was filtered and used for the chro-matographic analysis.
Results and discussion
The results of the study of the fatty acid composition of the kernel and the pericarp of Viburnum opulus are given in Table. Eleven fatty acids (8 were identified) were found in the kernel. In the pericarp there were 15 fatty acids (14 were identified). Eight fatty acids were common to the both objects: 2 saturated and 6 unsaturated. It is noteworthy that the content of the amount of unsaturated fatty acids in the kernel was 97.37 % of the total amount, while the content of unsaturated fatty acids in the pericarp was in 1.5 times lower and was 66.77 % of the total amount. Monoun-saturated oleic acid was dominant, its content in the kernel was 52.12 % of the total amount, and in the pericarp it was almost twice lower - 29.72 % of the total amount. In the pericarp, the content of polyunsaturated linoleic acid (26.80 % of the total amount) and saturated palmitic acid (23.12 % of the total amount) were comparable with the content of oleic acid. Thus, in the domestic raw material the ratio of fatty acids of 18 : 1 prevails, but not 18 : 2.
Table
The quantitative content of fatty acids in the components of Viburnum opulus fruit (% of the amount)
Index according to IUPAC Acid name Component of the fruit
according to IUPAC trivial kernel pericarp
Saturated FA
C 12 : 0 Dodecanoic Lauric - 1.12
C 14 : 0 Tetradecanoic Myristic - 2.02
C 16 : 0 Hexadecanoic Palmitic 1.72 23.12
C 18 : 0 Octadecanoic Stearic 0.57 3.45
C 20 : 0 Eicosanoic Arachidic - 1.67
C 22 : 0 Docosanoic Behenic - 0.85
C 24 : 0 Tetracosanoic Lignoceric - 0.90
The amount of saturated FA 2.29 33.13
Unsaturated FA
Index according to IUP AC Acid name Component of the fruit
according to IUPAC trivial kernel pericarp
Saturated FA
С 14 : 1 (9Z) -tetradecenoic Myristoleic 0.04 0.38
С 16 : 1 (9Z)-hexadec-9-enoic Palmitoleic 0.22 1.14
С 18 : 1 cis-9-octadecene Oleic 52.12 29.72
С 18 : 2 9,12-octadecadienoic Linoleic 44.07 26.80
С 18 : 3 9,12,15-octadecatriene Linolenic 0.54 7.64
С 20 : 1 11-Eicosenoic Gondoic 0.37 0.12
С 22 : 1 c/5-13-docosenoic Erucic - 0.97
The amount of unsaturated FA 97.37 66.77
Unidentified compound 0.07 0.10
Unidentified compound 0.25 -
Unidentified compound 0.03 -
The total amount of FA 100.01 100.00
CONCLUSIONS
The qualitative composition of fatty acids in the kernel and the pericarp of domestic Viburnum opulus fruits has been studied. The results obtained indicate the prospects of creating new drugs based on the biologically active complex Omega-9 containing in the kernel and the pericarp of Viburnum opulus fruit.
REFERENCES:
1. Пристром, М. С. Омега-3 полиненасыщенные жирные кислоты: механизмы действия, доказательства пользы и новые перспективы применения в клинической практике / М. С. Пристром, И. И. Се-мененков, Ю. А. Олихвер // Междунар. обзоры : клин. практика и здоровье. - 2017. - № 2. - C. 7582.
2. Genes for de novo biosynthesis of omega-3 polyunsaturated fatty acids are widespread in animals / N. Kabeya, M. M. Fonseca, E. K. Ferrier et al. // Science Advances. - 2018. - Vol. 4, Issue 5. - P. 6849.
3. Parisi, L. R. Very Long Chain Fatty Acids Are Functionally Involved in Necroptosis / L. R. Parisi, N. Li, G. E. Atilla-Gokcumen // Cell Chemical Biol. -2017. - Vol. 24, Issue 12. - P. 1445-1454.
4. Бубенчикова, В. Н. Жирнокислотный и минеральный состав травы горлюхи ястребинковой / В. Н. Бубенчикова, И. В. Степнова // Химия растит. сырья. - 2018. - № 1. - С. 113-119.
5. Жирнокислотный состав масла плодов рас-торопши пятнистой, культивируемой в самарской области / В. A. Куркин, O. В. Сазонова, Д. В. Роси-хин, Т. К. Рязанова // Химия растит. сырья. - 2017.
- Т. 3. - С. 101.
6. Химический состав масла семян арбуза, выделенного методом сверхкритической флюидной экстракции / А. В. Великородов, В. Б. Ковалев, А. Г. Тырков, С. Б. Носачев // Междунар. журн. прикладных и фундаментальных исследований. - 2014.
- № 12 (ч. 1) - С. 125-128.
7. Discontinuous fatty acid elongation yields hy-droxylated seed oil with improved function / X. Li, A. M. Teitgen, A. Shirani et al. // Nature Plants. - 2018. -Vol. 4. - P. 711-720.
8. Seed-Specific Expression of AtLECl Increased Oil Content and Altered Fatty Acid Composition in Seeds of Peanut (Arachis hypogaea L.) / Tang, P. Xu, W. Ma et al. // Front Plant Sci. - 2018. - Vol. 9. - P. 260.
9. Державна фармакопея Украши / Державне шдприемство «Украшський науковий фармакопей-ний центр якосп лжарських за-собiв». - 2-е вид. -Доп. 1. - Х. : Державне шдприемство «Украшський науковий фармакопейний центр якосп лжарських засобiв», 2016. - 360 с.
10. Influence of Reduced Temperature on Lipid Composition of Viburnum opulus Seeds / A. R. Kari-mova, S. G. Yunusova, M. S. Yunusov, G. Galkin // Chemistry of Natural Compounds. - 2005. - Vol. 41 (6). - P. 636-642.
11. Change on storage of biological activity Viburnum opulus seed components / S. G. Yunusova, A. R. Karimova, E. M. Tsyrlina, N. Denisenko // Chemistry of Natural Compounds. - 2004. -Vol. 40 (5). - P. 423-426.
12. Lipids and lipophilic components of Viburnum opulus fruits during maturation / A. R. Karimova, S. G. Yunusova, E. G. Galkin et al. // Rus. Chemical Bulletin. - 2004. - Vol. 53 (1). - P. 245-250.
13. Lipids, Lipophilic Components, and Biologically Active Fractions of Viburnum opulus L. Seeds. / A. R. Karimova, S. G. Yunusova, E. G. Galkin et al. // Chem. of Natural Compounds. - 2000. - Vol. 36 (6). -P. 560-564.
14. Yunusova, S. G. Lipids of Viburnum opulus seeds / S. G. Yunusova, E. G. Zinurova, M. S. Yunusov // Rus. Chemical Bulletin. - 1998. - Vol. 47 (6). - P. 1209-1213.
15. Determination of fatty acid compositions by the direct transesterification of seed lipids / S. G. Yunusova, F. K. Sitnikova, A. R. Karimova et al. // Chem. of Natural Compounds. - 1998. - Vol. 34 (2). -P. 137-140.
16. Прохорова, М. И. Методы биохимических исследований. - Л. : Химия, 1982. - 272 с.
