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5
2023. Vol. 25. № 5 Issue Doi: 10.26787/nydha-2686-6838-2023-25-5 E-ISSN 2686-6838
—-Э^СФО»^-—
RESEARCH ARTICLE 3. Medical sciences
УДК 615.074
Corresponding Author: Fetisova Angelika Nikolaevna - doctor ofpharmaceutical Sciences, professor of the Department of Chemistry, Institute of Pharmacy named after A.P. Nelyubin I.M. Sechenov First Moscow State Medical University (Sechenov University), Moscow, Russia Federation
E-mail: fetisova_a_n@staff.sechenov. ru.
© Lopatin V.V., Fetisova A.N. - 2023 | *** | Accepted: 28.05.2023
http://dx.doi.org//10.26787/nydha-2686-6838-2023-25-5-18-23
СРАВНИТЕЛЬНЫЙ АНАЛИЗ КАЧЕСТВЕННОГО И КОЛИЧЕСТВЕННОГО СОДЕРЖАНИЯ ЖИРНЫХ КИСЛОТ В ОБРАЗЦАХ ЛЕКАРСТВЕННОГО ПРЕПАРАТА «РЫБИЙ ЖИР ОЧИЩЕННЫЙ ДЛЯ ВНУТРЕННЕГО ПРИМЕНЕНИЯ» РОССИЙСКОГО ПРОИЗВОДСТВА
Лопатин В.В., Фетисова А.Н.
ФГАОУ ВО «Первый Московский государственный медицинский университет имени И.М. Сеченова» (Сеченовский Университет), г. Москва, Российская Федерация
Аннотация. Рыбий жир - один из важных продуктов, получаемых из морских гидробионтов. Его широко используют как в промышленных, так и в медицинских целях. Химический состав рыбьего жира, как и других субстанций липофильной природы, традиционно разделяют на омыляемые и неомыляемые фракции, содержащие, моно-, ди- и триацилглицерины высших жирных кислот, фосфолипиды, стериловые эфиры, стеролы и свободные жирные кислоты. В исследованиях как пресноводного, так и океанического рыбьего жира было установлено, что жир из морской рыбы содержит 35 ненасыщенных жирных кислот с количеством двойных связей от 1 до 6. Целью настоящего исследования является проведение сравнительного анализа качественного и количественного содержания жирных кислот в образцах препарата «Рыбий жир очищенный для внутреннего применения»российского производства ООО «Тульская фармацевтическая фабрика». Объектами исследования были: образцы рыбьего жира 2 серии, А и Б, российского производства ООО «Тульская фармацевтическая фабрика». Рыбий жир — это жирное масло, полученное из печени рыб, одобренное государственной фармакопеей и применяемое в качестве лекарственного средства при гипо- и авитаминозе A и D. Для качественного и количественного анализа использовали газовый хроматограф TRACE GC Thermo Fisher Scientific. Проанализированные образцы рыбьего жира не соответствуют требованиям государственной фармакопеи XIV.
Ключевые слова: жирные кислоты, качественный анализ, количественный анализ, Государственная фармакопея XIV издания.
COMPARATIVE ANALYSIS OF QUALITATIVE AND QUANTITATIVE COMPOSITION OF FATTY ACIDS IN SAMPLES OF THE MEDICINE "FISH FAT PURIFIED FOR INTERNAL USE" OF THE RUSSIAN PRODUCTION
Lopatin V.V., Fetisova A.N.
I.M. Sechenov First Moscow State Medical University, Moscow, Russian Federation
Abstract. Fish oil is one of the important products obtained from marine aquatic organisms. It is widely used for both industrial and medical purposes. The chemical composition of fish oil, as well as other substances of a lipophilic nature, is traditionally divided into saponifiable and unsaponifiable fractions containing mono-, di- and triacylglycerols of higher fatty acids, phospholipids, steryl esters, sterols and free fatty acids. In studies of both freshwater and ocean fish oils, marine fish oils have been found to contain 35 unsaturated fatty acids with between 1 and 6 double bonds. The aim of this study is to conduct a comparative analysis of the qualitative and quantitative content offatty acids in samples of the preparation "fish oil for internal use" of the Russian production of Tula Pharmaceutical Factory LLC. The objects of study were: samples offish oil of 2 series, A and B, Russian-made LLC Tula Pharmaceutical Factory.
Fish oil is a fatty oil obtained from the liver of fish, approved in the state Pharmacopieia and used as a medicine venous means. For qualitative and quantitative analysis, a TRACE GC Thermo Fisher Scientific gas chromatograph was used. The analyzed samples offish oil do not meet the requirements of the state pharmacopoeia XIV.
Keywords: fatty acids, qualitative analysis, quantitative analysis, State Pharmacopieia XIV edition.
Introduction. Fish oil is one of the important products derived from marine animals and it's need increases from time to time for various purposes: for example, in the industrial field and in the field of human consumption [1]. Like other oils and fats, the composition of fish oil can be divided into fractions, such as triacylglycerol, diacylglycerol, monoacylglycerol, phospholipids, sterile esters, sterols and free fatty acids. The amount of total lipids can vary between different tissues and organs, as well as between different species. The type of fatty acid present as a free acid or a neutral lipid differs significantly from species to species and aqueous media [2]. In a study of both freshwater and ocean fish oil, it was found that fish oil preparations from marine fish contained 35 unsaturated fatty acids with 1-6 double bonds. In contrast, freshwater fish oil preparations contained 14 unsaturated fatty acids having 1-5 double bonds. Sea fish oil preparations contained a significant amount of unsaturated fatty acids > 20 C, such as C20: 5 and C22: 6, while all freshwater fish fatty acids had a chain length of less than 20 carbon atoms. Fatty acids, except 20: 1 and 22: 1, are the main compounds of fish oil from marine animals of temperate and northern latitudes, having saturated (14: 0 and 16: 0), monounsaturated (16: 1 and 18: 1) and polyunsaturated (predominantly ©-3) fatty acids. The polyunsaturated fatty acids of triacylglycerol and lecithin were preferably located in the P-position 11. Various scientists studied the composition of fish oil in the liver and found that 9199% of the fatty acids in the P-position are unsaturated and 36-86% of the fatty acids in the aposition are saturated [3], [4], [5].
The aim of this study - to conduct a qualitative and quantitative analysis of samples of the drug "purified fish oil for internal use" using modern analytical methods.
Materials and methods. The samples of fish oil of 2 series, A and B, Russian-made LLC Tula Pharmaceutical Factory. Fish oil is a fatty oil obtained from the liver of fish: Atlantic cod - Gadus morrhua Linne, Baltic cod - Gadus morrhua callarial Linne, haddock - Melanogrammus aeglefinus L., northern
blue whiting - Micromesistius poutaussou (Risso) of the cod liver family - Gididae or blunt-nosed -Coryphaenoides rupestris G. macrorus family -Macrouride containing retinol, colecalciferol and omega-3 fatty acids (eicosopentaenoic acid - at least 13%, docosahexaenoic acid - at least 9%, the amount of polyunsaturated fatty acids - at least 28%), and used as a medicine venous means [6].
Sample preparation was carried out according to the following method: the test sample of fish oil, an exact sample of about 0.5 g, was mixed with 1 ml of methyl alcohol and 150 pl of acetyl chloride. Adding was carried out in stages. The resulting mixture was placed in a shaker for 1 hour with constant heating of 75 ° C. Then, 400 pl of hexane was added and again placed in a shaker without heating. Then they removed it from the shaker, waited for separation, and a layer of hexane was taken into the sampler vial. Then a sample was taken for analysis and a survey was performed on a GC / MS.
GC conditions: Thermo Scientific TRACE TR-5MS column. The volume of the injected sample is 0.1 pl. The flow rate is 0.4 ml / min. The total analysis time is 28 minutes. The maximum temperature of the thermostat is 350oC. All the values are presented as means ± standard error of the means (SE). Comparisons between different groups were carried out using one way analysis of variance. Difference was considered significant when p <0.05.
Results and Discussion. Qualitative analysis showed that the following fatty acids were contained in the samples: myristic, pentadecanoic, palmitoleic, palmitic, stearidonic, linoleic, oleic, 13-octadecenoic, stearic, eicosapentaenoic, 9-eicosenoic,
docosagenicenoic and erucic acid. Quantitative analysis showed that in the samples of series A the content of saturated fatty acids is 20.7%, unsaturated - 54.7%, polyunsaturated - 24.6% (table 1), in series B samples, the amount of saturated fatty acids is 22.4%, unsaturated - 51.9%, polyunsaturated - 25.7% (table 2). Statistical analysis of fatty acid composition of fish fat samples of both series was also provided (table 3).
Table 1
Results of analysis of fatty acid composition of samples of fish fat series A
Apex RT Area %Area Height %Height Acid
11,82 7,96E+08 4,16 4,66E+08 4,83 Myristic acid (С14:0)
13,19 62832156 0,33 27899295 0,29 Pentadecanoic acid (05:0)
14,67 1,38E+09 7,19 4,72E+08 4,89 Palmitoleic acid (06:1)
15,07 2,51E+09 13,10 8,30E+08 8,59 Palmitic acid (06:0)
19,48 4,32E+08 2,25 1,36E+08 1,41 Stearidonic acid (08:4 ra-3)
19,66 3,42E+08 1,78 1,30E+08 1,34 Linoleic acid (08:2 ra-6)
19,78 3,91E+09 20,43 1,32E+09 13,63 Oleic acid (C18:1)
19,88 9,75E+08 5,09 3,95E+08 4,09 13-octadecenoic acid (C18:5)
20,20 5,87E+08 3,07 2,64E+08 2,73 Stearic acid (08:0)
21,89 1,30E+09 6,80 8,92E+08 9,24 Eicosapentaenoic acid ^20:5, ra-3)
22,18 2,83E+09 14,76 1,66E+09 17,14 9- eicosenoic acid ^20:1)
23,29 1,67E+09 8,73 1,29E+09 13,39 Docosagenicenoic acid (C22:6, ra-3)
23,54 2,36E+09 12,32 1,78E+09 18,43 Erucic acid (C22:1)
Таблица 1
Результаты анализа жирно-кислотного состава образцов рыбьего серии А
Apex RT Area %Area Height %Height Acid
11,82 7,96E+08 4,16 4,66E+08 4,83 Митистиновая (С14:0)
13,19 62832156 0,33 27899295 0,29 Пентадекановая (С15:0)
14,67 1,38E+09 7,19 4,72E+08 4,89 Пальмитолеиновая (С16:1)
15,07 2,51E+09 13,10 8,30E+08 8,59 Пальмитиновая (С16:0)
19,48 4,32E+08 2,25 1,36E+08 1,41 Стеаридоновая (С18:4 га-3)
19,66 3,42E+08 1,78 1,30E+08 1,34 Линолевая (С18:2 га-6)
19,78 3,91E+09 20,43 1,32E+09 13,63 Олеиновая (C 18:1)
19,88 9,75E+08 5,09 3,95E+08 4,09 13-октадеценовая (C18:5)
20,20 5,87E+08 3,07 2,64E+08 2,73 Стеариновая (С18:0)
21,89 1,30E+09 6,80 8,92E+08 9,24 Эйкозопентаеновая (С20:5, га-3)
22,18 2,83E+09 14,76 1,66E+09 17,14 9- эйкозеновая (С20:1)
23,29 1,67E+09 8,73 1,29E+09 13,39 Эйкозогексаеновая (C22:6, га-3)
23,54 2,36E+09 12,32 1,78E+09 18,43 Эруковая (C22:1)
Table 2
Results of analysis of fatty acid composition of samples of fish fat series В
Apex RT Area %Area Height %Height Acid
11,81 7,6E+08 4,90 4,4E+08 5,61 Myristic acid (04:0)
13,19 64164477 0,41 27894951 0,36 Pentadecanoic acid (05:0)
14,67 1,1E+09 7,07 3,76E+08 4,80 Palmitoleic acid (06:1)
15,07 2,22E+09 14,32 7,4E+08 9,44 Palmitic acid (06:0)
19,47 3,65E+08 2,35 1,12E+08 1,43 Stearidonic acid (08:4 ra-3)
19,66 2,81E+08 1,81 1,05E+08 1,34 Linoleic acid (08:2 ra-6)
19,77 2,87E+09 18,49 9,95E+08 12,69 Oleic acid (C18:1)
19,87 7,25E+08 4,67 2,99E+08 3,81 13-octadecenoic acid (C18:5)
20,19 4,43E+08 2,86 1,97E+08 2,52 Stearic acid (08:0)
21,88 1,14E+09 7,38 7,81E+08 9,97 Eicosapentaenoic acid ^20:5, ra-3)
22,18 2,07E+09 13,34 1,18E+09 15,05 9- eicosenoic acid ^20:1)
23,29 1,46E+09 9,38 1,09E+09 13,90 Docosagenicenoic acid (C22:6, ra-3)
23,54 2,02E+09 13,01 1,49E+09 19,08 Erucic acid (C22:1)
Таблица 2
Результаты анализа жирно-кислотного состава образцов рыбьего серии B
Apex RT Area %Area Height %Height Acid
11,81 7,6E+08 4,90 4,4E+08 5,61 Митистиновая (С14:0)
13,19 64164477 0,41 27894951 0,36 Пентадекановая (С15:0)
14,67 1,1E+09 7,07 3,76E+08 4,80 Пальмитолеиновая (С16:1)
15,07 2,22E+09 14,32 7,4E+08 9,44 Пальмитиновая (С16:0)
19,47 3,65E+08 2,35 1,12E+08 1,43 Стеаридоновая (С18:4 га-3)
19,66 2,81E+08 1,81 1,05E+08 1,34 Линолевая (С18:2 га-6)
19,77 2,87E+09 18,49 9,95E+08 12,69 Олеиновая (C 18:1)
19,87 7,25E+08 4,67 2,99E+08 3,81 13-октадеценовая (C18:5)
20,19 4,43E+08 2,86 1,97E+08 2,52 Стеариновая (С18:0)
21,88 1,14E+09 7,38 7,81E+08 9,97 Эйкозопентаеновая (С20:5, га-3)
22,18 2,07E+09 13,34 1,18E+09 15,05 9- эйкозеновая (С20:1)
23,29 1,46E+09 9,38 1,09E+09 13,90 Эйкозогексаеновая (C22:6, га-3)
23,54 2,02E+09 13,01 1,49E+09 19,08 Эруковая (C22:1)
Table 3
Statistical analysis of fatty acid composition of fish fat samples both series
Series А Series В
п/п Fatty acid Relative peak area, % (average value) Statistical Characteristics (n=5, P=0,95) Relative peak area, % (average value) Statistical Characteristics (n=5, P=0,95)
1. Myristic acid (C14:0) 4,16 s=0,0011, x ± A x =4,16±5*10-4 s, %=0,1% 4,9 s=0,0255, x ± A x =4,9±0,009 s, %=0,2%
2. Pentadecanoic acid (C15:0) 0,33 s=0,0003, x ± A X =0,33±0,022 s, %=0,6% 0,41 s=0,0004, x ± A x =0,41±0,002 s, %=0,4%
3. Palmitoleic acid (C16:1) 7,19 s=0,0030, x ± A x =7,19±0,002 s, %=0,1% 7,07 s=0,0257, x ± A x =7.07+0,007 s, %=0,1%
4. Palmitic acid (C16:0) 13,1 s=0,0105, x ± A x =13,10±8*10-4 s, %=0,1% 14,33 s=0,1033, x ± A x =14,33±0,014 s, %=0,1%
5. Stearidonic acid (C18:4 ra-3) 2,25 s=0,0058, x ± A x =2,25±0,005 s, %=0,2% 2,36 s=0,0057, x ± A x =2,36±0,0046 s, %=0,2%
6. Linoleic acid (C18:2 ra-6) 1,78 s=0,0025, x ± A x =1,78±0,003 s, %=0,2% 1,81 s=0,0043, x ± A x =1,81±0,005 s, %=0,3%
7. Oleic acid (C18:1) 20,43 s=0,0233, x ± A x =20,43±0,002 s, %=0,1% 18,49 s=0,1975, x ± A x =18,49±0,020 s, %=0,1%
8. 13-octadecenoic acid (C18:5) 5,09 s=0,1310, x ± A x =5,09±0,16 s, %=3,2% 4,67 s=0,0475, x ± A x =4,67±0,0195 s, %=0,4%
9. Stearic acid (C18:0) 3,07 s=0,0025, x ± A x =3,07±0,002 s, %=0,5% 2,86 s=0,0058, x ± A x =2,86±0,004 s, %=0,1%
10. Eicosapentaenoic acid (C20:5, ra-3) 6,8 s=0,011, x ± A x =6,80±0,003 s, %=0,4% 7,38 s=0,0421, x ± A x =7,38±0,011 s, %=0,2%
11. 9- eicosenoic acid (C20:1) 14,76 s=0,0233, x ± A x =14,76±0,003 s, %=0,2% 13,34 s=0,1033, x ± A x=13,34±0,015 s, %=0,1%
12. Docosagenicenoic acid (C22:6, га-3) 8,73 s=0,0058, x ± Д x =8,73±0,001 s, %=0,1% 9,38 s=0,0475, x ± Д x =9,38±0,001 s, %=0,1%
13. Erucic acid (C22:1) 12,32 s=0,0108, x ± Д x =12,32±0,002 s, %=0,1% 13,01 s=0,1808, x ± Д x =13,01±0,03 s, %=0,2%
Таблица 3
Статистический анализ жирно-кислотного состава обоих образцов рыбьего жира
Серия А Серия В
п/п Жирная кислота Относительная площадь пика, % (среднее значение) Статистические характеристики (n=5, P=0,95) Относительная площадь пика, % (среднее значение) Статистические характеристики (n=5, P=0,95)
1. Миристиновая кислота 4,16 s=0,0011, x ± Д x=4,16±5*10-4, s, %=0,1% 4,9 s=0,0255, x ± Д x=4,9±0,009 s, %=0,2%
2. Пентадекановая кислота 0,33 s=0,0003, x ± Д x=0,33±0,022, s, %=0,6% 0,41 s=0,0004, x ± Д x=0,41±0,002, s, %=0,4%
3. Пальмитолеинова я кислота 7,19 s=0,0030, x ± Д x=7,19±0,002, s, %=0,1% 7,07 s=0,0257, x ± Д x=7.07+0,007, s, %=0,1%
4. Пальмитиновая кислота 13,1 s=0,0105, x ± Д x=13,10±8*10-4, s,%=0,1% 14,33 s=0,1033, x ± Д x=14,33±0,014, s, %=0,1%
5. Стеаридоновая кислота 2,25 s=0,0058, x ± Д x=2,25±0,005, s, %=0,2% 2,36 s=0,0057, x ± Д x=2,36±0,0046, s, %=0,2%
6. Линолевая кислота 1,78 s=0,0025, x ± Д x=1,78±0,003, s, %=0,2% 1,81 s=0,0043, x ± Д x=1,81±0,005, s, %=0,3%
7. Олеиновая кислота 20,43 s=0,0233, x ± Д x=20,43±0,002, s, %=0,1% 18,49 s=0,1975, x ± Д x=18,49±0,020, s, %=0,1%
8. 13 -Октадеценовая кислота 5,09 s=0,1310, x ± Д x=5,09±0,16 s, %=3,2% 4,67 s=0,0475, x ± Д x=4,67±0,0195, s, %=0,4%
9. Стеариновая кислота 3,07 s=0,0025, x ± Д x=3,07±0,002, s, %=0,5% 2,86 s=0,0058, x ± Д x=2,86±0,004, s, %=0,1%
10. Эйкозапентае-новая кислота 6,8 s=0,011, x ± Д x=6,80±0,003, s, %=0,4% 7,38 s=0,0421, x ± Д x=7,38±0,011, s, %=0,2%
11. 9-Эйкозеновая кислота 14,76 s=0,0233, x ± Д x=14,76±0,003, s, %=0,2% 13,34 s=0,1033, x ± Д x=13,34±0,015, s, %=0,1%
12. Докозагексае-новая кислота 8,73 s=0,0058, x ± Д x=8,73±0,001, s, %=0,1% 9,38 s=0,0475, x ± Д x=9,38±0,001, s, %=0,1%
13. Эруковая кислота 12,32 s=0,0108, x ± Д x=12,32±0,002, s, %=0,1% 13,01 s=0,1808, x ± Д x=13,01±0,03, s, %=0,2%
Conclusion: The analyzed samples of fish oil do not meet the requirements of regulatory documentation: the content of eicosapentaenoic acid is 6.8% and 7.38%, which does not meet the requirements of the Global Fund of 14th edition (at least 13%), the content of docosahexaenoic acid corresponds only to samples of series B (9, 38%, 8.73% in series A samples, the required content is not less than 9%).
The content of polyunsaturated fatty acids also does not meet the requirements of regulatory documentation (24.64% and 25.7%, the norm is not less than 28%). The study may be the starting point for further analysis of Russian-made fish oil in order to identify more optimal and accurate methods for qualitative and quantitative analysis.
REFERENCES
БИБЛИОГРАФИЧЕСКИМ СПИСОК
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[2]. Ilievska, B. Topical Formulation Comprising Fatty Acid Extract from Cod Liver Oil: Development, Evaluation and Stability Studies / B. Ilievska, T. Loftsson // Marine Drugs. - 2016 - Vol. 14. - P. 1-11.
[3]. M. Haq, M. Modifications of Atlantic salmon by-product oil for obtaining different w- 3 polyunsaturated fatty acids concentrates: An approach to comparative analysis / M. Haq, Seul-Ki Park, Min-Jung Kim // JFDA. - 2018. - Vol. 26, No 4. - P. 545- 556.
[4]. Ochi, E. Eicosahexanoic Acid (EPA) and Docosahexanoic Acid (DHA) in Muscle Damage and Function / E. Ochi, Y. Tsuchiya // Nutrients. - 2018. -Vol. 10, No 5.- P. 552-564
[5]. Roy, L. Development and Validation of a Single HPLC Method for Analysis of Purines in Fish Oil Supplements / L. Roy, C. C. Harrell, A. S. Ryan // Food and Nutrition Sciences. - 2013. - Vol. 4, No 12. - P. 1255-1259.
[6]. Государственная фармакопея Российской Федерации Том 4. - XIV издания. Москва, 2018. - URL http://femb.ru/femb/pharmacopea.php (дата обращения 20.03.2023)
Author Contributions. Lopatin V.V. - literature review, text writing, statistical data processing, Fetisova A.N. - the concept and design of the study.
Conflict of Interest Statement. The authors declare no conflict of interest. Lopatin V.V. - SPIN ID: 2919-1812 ORCID ID: 0000-0002-6543-0904 Fetisova A.N. - SPIN ID: 4147-5538, ORCID ID: 0000-0001-8077-0520
For citation: Lopatin V.V., Fetisova A.N. COMPARATIVE ANALYSIS OF QUALITATIVE AND QUANTITATIVE COMPOSITION OF FATTY ACIDS IN SAMPLES OF THE MEDICINE "FISH FAT PURIFIED FOR INTERNAL USE" OF THE RUSSIAN PRODUCTION. // Medical & pharmaceutical journal "Pulse". - 2023;25(5): 18-23. http://dx.doi.org/Z10.26787/nydha-2686-6838-2023-25-5-25-34.
Вклад авторов. Лопатин В.В. - обзор литературы, написание текста, статистическая обработка данных, Фетисова А.Н. - концепция и дизайн исследования.
Заявление о конфликте интересов. Авторы заявляют об отсутствии конфликта интересов.
Лопатин В.В. - SPIN ID: 2919-1812 ORCID ID: 0000-0002-6543-0904 Фетисова А.Н. - SPIN ID: 4147-5538, ORCID ID: 0000-0001-8077-0520
Для цитирования: Лопатин В.В., Фетисова А.Н. СРАВНИТЕЛЬНЫЙ АНАЛИЗ КАЧЕСТВЕННОГО И КОЛИЧЕСТВЕННОГО СОДЕРЖАНИЯ ЖИРНЫХ КИСЛОТ В ОБРАЗЦАХ ЛЕКАРСТВЕННОГО ПРЕПАРАТА «РЫБИЙ ЖИР ОЧИЩЕННЫЙ ДЛЯ ВНУТРЕННЕГО ПРИМЕНЕНИЯ» РОССИЙСКОГО ПРОИЗВОДСТВА // Медико-фармацевтический журнал "Пульс". 2023;25(5): 18-23. http://dx.doi.org//10.26787/nydha-2686-6838-2023-25-5-18-23.
