Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment

Introduction. Polyprenols are known as a class of natural long-chain isoprenoid alcohols, which are natural bioregulators that directly participate in the synthesis of cell membrane glycoproteins. Their hepatoprotective activity is proven, as well other types of their pharmacological effects are kno...

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Published in:Conservation Biology
Main Authors: N. S. Popov, A. A. Antipina, S. V. Savintsev, V. Y. Balabanyan, Н. С. Попов, А. А. Антипина, С. В. Савинцев, В. Ю. Балабаньян
Format: Article in Journal/Newspaper
Language:Russian
Published: LLC «CPHA» 2024
Subjects:
валидация
high-performance liquid chromatography
mass spectrometry
HPLC-MS/MS
validation
высокоэффективная жидкостная хроматография
масс-спектрометрия
ВЭЖХ-МС/МС
Sibirica
Online Access:https://www.pharmjournal.ru/jour/article/view/1807
https://doi.org/10.33380/2305-2066-2024-13-2-1638
id ftjrirls:oai:oai.pharmjournal.elpub.ru:article/1807
record_format openpolar
institution Open Polar
collection Drug development & registration
op_collection_id ftjrirls
language Russian
topic валидация
high-performance liquid chromatography
mass spectrometry
HPLC-MS/MS
validation
высокоэффективная жидкостная хроматография
масс-спектрометрия
ВЭЖХ-МС/МС
spellingShingle валидация
high-performance liquid chromatography
mass spectrometry
HPLC-MS/MS
validation
высокоэффективная жидкостная хроматография
масс-спектрометрия
ВЭЖХ-МС/МС
N. S. Popov
A. A. Antipina
S. V. Savintsev
V. Y. Balabanyan
Н. С. Попов
А. А. Антипина
С. В. Савинцев
В. Ю. Балабаньян
Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
topic_facet валидация
high-performance liquid chromatography
mass spectrometry
HPLC-MS/MS
validation
высокоэффективная жидкостная хроматография
масс-спектрометрия
ВЭЖХ-МС/МС
description Introduction. Polyprenols are known as a class of natural long-chain isoprenoid alcohols, which are natural bioregulators that directly participate in the synthesis of cell membrane glycoproteins. Their hepatoprotective activity is proven, as well other types of their pharmacological effects are known, which is the reason of significant interest in these substances as a promising medicinal product. It is non-trivial task to determine the sum of polyprenols in extracts as include design and implementation of accurate reproducible analytical methods, which will subsequently be used in standardization.Aim. Development and validation of the chromatographic-mass spectrometric technique for polyprenols identification and their quantitative assessment.Materials and methods. Chromatographic separation of polyprenols was performed by using an HPLC Agilent 1260 Infinity II (Agilent Technologies, США); with the mixture of methanol, n-hexane, propanol-2, and aqueous ammonium acetate solution as eluent in gradient mode. An AB Sciex QTrap® 3200MD (AB Sciex Pte. Ltd., Singapore) triple quadrupole mass spectrometer was used as a detector, with the registration of polyprenols adducts.Results and discussion. The conditions for chromatographic separation and detection of polyprenols were identified. The developed technique was validated for the following characteristics: specificity, limit of detection, limit of quantification, linearity, accuracy, precision, range of application, and stability.Conclusion. It was determined the content of polyprenols in the substance recieved from Ginkgo biloba L. and Picea abies L. The developed technique can be used in the future to assess the content of polyprenols in drug products or pharmaceutical substances. Введение. Полипренолы представляют собой класс длинноцепочечных изопреноидных спиртов природного происхождения. Полипренолы являются природными биорегуляторами, принимающими непосредственное участие в синтезе гликопротеинов клеточных мембран, обладают выраженной гепатопротекторной ...
format Article in Journal/Newspaper
author N. S. Popov
A. A. Antipina
S. V. Savintsev
V. Y. Balabanyan
Н. С. Попов
А. А. Антипина
С. В. Савинцев
В. Ю. Балабаньян
author_facet N. S. Popov
A. A. Antipina
S. V. Savintsev
V. Y. Balabanyan
Н. С. Попов
А. А. Антипина
С. В. Савинцев
В. Ю. Балабаньян
author_sort N. S. Popov
title Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
title_short Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
title_full Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
title_fullStr Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
title_full_unstemmed Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
title_sort development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment
publisher LLC «CPHA»
publishDate 2024
url https://www.pharmjournal.ru/jour/article/view/1807
https://doi.org/10.33380/2305-2066-2024-13-2-1638
genre Sibirica
genre_facet Sibirica
op_source Drug development & registration; Том 13, № 2 (2024); 133-141
Разработка и регистрация лекарственных средств; Том 13, № 2 (2024); 133-141
2658-5049
2305-2066
op_relation https://www.pharmjournal.ru/jour/article/view/1807/1270
https://www.pharmjournal.ru/jour/article/downloadSuppFile/1807/2248
Vanaga I., Gubernator J., Nakurte I., Kletnieks U., Muceniece R., Jansone B. Identification of Abies sibirica L. polyprenols and characterisation of polyprenol-containing liposomes. Molecules. 2020;25(8):1801. DOI:10.3390/molecules25081801.
Antipina A. A., Balabaniyan V. Yu., Approaches to producing, purifying, and standardizing polyprenols. Farmaciya (Pharmacy). 2021;70(6):15–19. DOI:10.29296/25419218-2021-06-03. (In Russ.)
Khodanovich M. Y., Pishchelko A. O., Glazacheva V. Y., Pan E. S., Krutenkova E. P., Trusov V. B., Yarnykh V. L. Plant polyprenols reduce demyelination and recover impaired oligodendrogenesis and neurogenesis in the cuprizone murine model of multiple sclerosis. Phytotherapy Research. 2019;33(5):1363–1373. DOI:10.1002/ptr.6327.
Liu L., Wang Y., Zhang J., Wang S. Advances in the chemical constituents and chemical analysis of Ginkgo biloba leaf, extract, and phytopharmaceuticals. Journal of Pharmaceutical and Biomedical Analysis. 2021;193:113704. DOI:10.1016/j.jpba.2020.113704.
Vyshlov E. V., Tsoy E. I., Sultanov V. S. Trusov V. B., Ryabov V. V. Hypolipidemic and hepatoprotective effects of a polyprenol-containing drug in patients with acute coronary syndrome. Bulletin of Experimental Biology and Medicine. 2018;165:319–321. DOI:10.1007/s10517-018-4159-x.
Yang L., Wang C.-Z., Ye J.-Z., Li H.-T. Hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves on CCl 4 -induced hepatotoxicity in rats. Fitoterapia. 2011;82(6):834–840. DOI:10.1016/j.fitote.2011.04.009.
Tsoi E. I., Vyshlov E. V., Ryabov V. V. Positive effect of polyprenol-containing drug on anxiety, depression and cognitive disorders in patients with acute coronary syndrome. European Heart Journal. Acute Cardiovascular Care. 2021;10(1):107. DOI:10.1093/ehjacc/zuab020.107.
Boateng I. D. Polyprenols in Ginkgo biloba; a review of their chemistry (synthesis of polyprenols and their derivatives), extraction, purification, and bioactivities. Food Chemistry. 2023;136006. DOI:10.1016/j.foodchem.2023.136006.
Boateng I. D., Soetanto D. A., Li F., Yang X.-M., Li Y.-Y. Separation and purification of polyprenols from Ginkgo biloba L. leaves by bulk ionic liquid membrane and optimizing parameters. Industrial Crops and Products. 2021;70:113828. DOI:10.1016/j.indcrop.2021.113828.
Mamatkulova N. M., Mukarramov N. I., Sasmakov S. A., Khidirova N. K. Polyprenols from Ficus carica Leaves and their Biological Activity. Chemistry of Natural Compounds. 2022;58(4):726–727. DOI:10.1007/s10600-022-03777-9.
Tao R., Wang C.-Z., Ye J.-Z., Zhou H., Chen H.-X., Zhang C.-W. Antibacterial, cytotoxic and genotoxic activity of nitrogenated and haloid derivatives of C 50 –C 60 and C 70 –C 120 polyprenol homologs. Lipids in Health and Disease. 2016;15(1):175. DOI:10.1186/s12944-016-0345-x.
Zhang C.-W., Li M.-F., Tao R., Peng M.-J., Wang Z.-H., Qi Z.-W., Xue X.-Y., Wang C.-Z. Physiochemical property and antibacterial activity of formulation containing polyprenol extracted from Ginkgo biloba leaves. Industrial Crops and Products. 2020;147:112213. DOI:10.1016/j.indcrop.2020.112213.
Yuan H., Zhang C., Zhou P., Yang X., Tao R., Ye J., Wang C. Preparation of polyprenol/poly (β-amino ester)/galactose targeted micelle carrier for enhancing cancer therapy. Arabian Journal of Chemistry. 2023;16(5);104679. DOI:10.1016/j.arabjc.2023.104679.
Zhang C.-W., Wang C.-Z., Tao R., Ye J.-Z. Separation of polyprenols from Ginkgo biloba leaves by a nano silica-based adsorbent containing silver ions. Journal of Chromatography A. 2019;1590:58–64. DOI:10.1016/j.chroma.2019.01.047.
Řezanka T., Votruba J. Chromatography of long chain alcohols (polyprenols) from animal and plant sources. Journal of Chromatography A. 2001;936(1–2):95–110. DOI:10.1016/S0021-9673(01)01152-9.
Yu J., Wang Y., Qian H., Zhao Y., Liu B., Fu C. Polyprenols from the needles of Taxus chinensis var. mairei. Fitoterapia. 2012;83(5);831–837. DOI:10.1016/j.fitote.2012.01.007.
Gharwalová L., Palyzová A., Marešová H., Kolouchová I., Kyselová L., Řezanka T. Identification of homologous polyprenols from thermophilic bacteria. Microorganisms. 2021;9(6):1168. DOI:10.3390/microorganisms9061168.
D’Alexandri F. L., Gozzo F. C., Eberlin M. N., Katzin A. M. Electrospray ionization mass spectrometry analysis of polyisoprenoid alcohols via Li + cationization. Analytical biochemistry. 2006;355(2):189–200. DOI:10.1016/j.ab.2006.06.014.
Kania M., Skorupinska‐Tudek K., Swiezewska E., Danikiewicz W. Atmospheric pressure photoionization mass spectrometry as a valuable method for the identification of polyisoprenoid alcohols. Rapid Communications in Mass Spectrometry. 2012;26(15):1705–1710. DOI:10.1002/rcm.6280.
https://www.pharmjournal.ru/jour/article/view/1807
doi:10.33380/2305-2066-2024-13-2-1638
op_rights Authors who publish with this journal agree to the following terms:Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.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), with an acknowledgement of its initial publication in this journal.Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) 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).
Авторы, публикующие в данном журнале, соглашаются со следующим:Авторы сохраняют за собой авторские права на работу и предоставляют журналу право первой публикации работы на условиях лицензии Creative Commons Attribution License, которая позволяет другим распространять данную работу с обязательным сохранением ссылок на авторов оригинальной работы и оригинальную публикацию в этом журнале.Авторы сохраняют право заключать отдельные контрактные договорённости, касающиеся не-эксклюзивного распространения версии работы в опубликованном здесь виде (например, размещение ее в институтском хранилище, публикацию в книге), со ссылкой на ее оригинальную публикацию в этом журнале.Авторы имеют право размещать их работу в сети Интернет (например в институтском хранилище или персональном сайте) до и во время процесса рассмотрения ее данным журналом, так как это может привести к продуктивному обсуждению и большему количеству ссылок на данную работу (См. The Effect of Open Access).
op_doi https://doi.org/10.33380/2305-2066-2024-13-2-163810.3390/molecules2508180110.29296/25419218-2021-06-0310.1002/ptr.632710.1016/j.jpba.2020.11370410.1007/s10517-018-4159-x10.1016/j.fitote.2011.04.00910.1093/ehjacc/zuab020.10710.1016/j.foodchem.2023.13600610
container_title Conservation Biology
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spelling ftjrirls:oai:oai.pharmjournal.elpub.ru:article/1807 2024-06-23T07:56:45+00:00 Development and validation of the chromatography-mass spectrometry technique for polyprenols quantitative assessment Разработка и валидация методики количественного определения полипренолов с применением высокоэффективной жидкостной хроматографии и масс-спектрометрии N. S. Popov A. A. Antipina S. V. Savintsev V. Y. Balabanyan Н. С. Попов А. А. Антипина С. В. Савинцев В. Ю. Балабаньян 2024-04-22 application/pdf https://www.pharmjournal.ru/jour/article/view/1807 https://doi.org/10.33380/2305-2066-2024-13-2-1638 rus rus LLC «CPHA» https://www.pharmjournal.ru/jour/article/view/1807/1270 https://www.pharmjournal.ru/jour/article/downloadSuppFile/1807/2248 Vanaga I., Gubernator J., Nakurte I., Kletnieks U., Muceniece R., Jansone B. Identification of Abies sibirica L. polyprenols and characterisation of polyprenol-containing liposomes. Molecules. 2020;25(8):1801. DOI:10.3390/molecules25081801. Antipina A. A., Balabaniyan V. Yu., Approaches to producing, purifying, and standardizing polyprenols. Farmaciya (Pharmacy). 2021;70(6):15–19. DOI:10.29296/25419218-2021-06-03. (In Russ.) Khodanovich M. Y., Pishchelko A. O., Glazacheva V. Y., Pan E. S., Krutenkova E. P., Trusov V. B., Yarnykh V. L. Plant polyprenols reduce demyelination and recover impaired oligodendrogenesis and neurogenesis in the cuprizone murine model of multiple sclerosis. Phytotherapy Research. 2019;33(5):1363–1373. DOI:10.1002/ptr.6327. Liu L., Wang Y., Zhang J., Wang S. Advances in the chemical constituents and chemical analysis of Ginkgo biloba leaf, extract, and phytopharmaceuticals. Journal of Pharmaceutical and Biomedical Analysis. 2021;193:113704. DOI:10.1016/j.jpba.2020.113704. Vyshlov E. V., Tsoy E. I., Sultanov V. S. Trusov V. B., Ryabov V. V. Hypolipidemic and hepatoprotective effects of a polyprenol-containing drug in patients with acute coronary syndrome. Bulletin of Experimental Biology and Medicine. 2018;165:319–321. DOI:10.1007/s10517-018-4159-x. Yang L., Wang C.-Z., Ye J.-Z., Li H.-T. Hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves on CCl 4 -induced hepatotoxicity in rats. Fitoterapia. 2011;82(6):834–840. DOI:10.1016/j.fitote.2011.04.009. Tsoi E. I., Vyshlov E. V., Ryabov V. V. Positive effect of polyprenol-containing drug on anxiety, depression and cognitive disorders in patients with acute coronary syndrome. European Heart Journal. Acute Cardiovascular Care. 2021;10(1):107. DOI:10.1093/ehjacc/zuab020.107. Boateng I. D. Polyprenols in Ginkgo biloba; a review of their chemistry (synthesis of polyprenols and their derivatives), extraction, purification, and bioactivities. Food Chemistry. 2023;136006. DOI:10.1016/j.foodchem.2023.136006. Boateng I. D., Soetanto D. A., Li F., Yang X.-M., Li Y.-Y. Separation and purification of polyprenols from Ginkgo biloba L. leaves by bulk ionic liquid membrane and optimizing parameters. Industrial Crops and Products. 2021;70:113828. DOI:10.1016/j.indcrop.2021.113828. Mamatkulova N. M., Mukarramov N. I., Sasmakov S. A., Khidirova N. K. Polyprenols from Ficus carica Leaves and their Biological Activity. Chemistry of Natural Compounds. 2022;58(4):726–727. DOI:10.1007/s10600-022-03777-9. Tao R., Wang C.-Z., Ye J.-Z., Zhou H., Chen H.-X., Zhang C.-W. Antibacterial, cytotoxic and genotoxic activity of nitrogenated and haloid derivatives of C 50 –C 60 and C 70 –C 120 polyprenol homologs. Lipids in Health and Disease. 2016;15(1):175. DOI:10.1186/s12944-016-0345-x. Zhang C.-W., Li M.-F., Tao R., Peng M.-J., Wang Z.-H., Qi Z.-W., Xue X.-Y., Wang C.-Z. Physiochemical property and antibacterial activity of formulation containing polyprenol extracted from Ginkgo biloba leaves. Industrial Crops and Products. 2020;147:112213. DOI:10.1016/j.indcrop.2020.112213. Yuan H., Zhang C., Zhou P., Yang X., Tao R., Ye J., Wang C. Preparation of polyprenol/poly (β-amino ester)/galactose targeted micelle carrier for enhancing cancer therapy. Arabian Journal of Chemistry. 2023;16(5);104679. DOI:10.1016/j.arabjc.2023.104679. Zhang C.-W., Wang C.-Z., Tao R., Ye J.-Z. Separation of polyprenols from Ginkgo biloba leaves by a nano silica-based adsorbent containing silver ions. Journal of Chromatography A. 2019;1590:58–64. DOI:10.1016/j.chroma.2019.01.047. Řezanka T., Votruba J. Chromatography of long chain alcohols (polyprenols) from animal and plant sources. Journal of Chromatography A. 2001;936(1–2):95–110. DOI:10.1016/S0021-9673(01)01152-9. Yu J., Wang Y., Qian H., Zhao Y., Liu B., Fu C. Polyprenols from the needles of Taxus chinensis var. mairei. Fitoterapia. 2012;83(5);831–837. DOI:10.1016/j.fitote.2012.01.007. Gharwalová L., Palyzová A., Marešová H., Kolouchová I., Kyselová L., Řezanka T. Identification of homologous polyprenols from thermophilic bacteria. Microorganisms. 2021;9(6):1168. DOI:10.3390/microorganisms9061168. D’Alexandri F. L., Gozzo F. C., Eberlin M. N., Katzin A. M. Electrospray ionization mass spectrometry analysis of polyisoprenoid alcohols via Li + cationization. Analytical biochemistry. 2006;355(2):189–200. DOI:10.1016/j.ab.2006.06.014. Kania M., Skorupinska‐Tudek K., Swiezewska E., Danikiewicz W. Atmospheric pressure photoionization mass spectrometry as a valuable method for the identification of polyisoprenoid alcohols. Rapid Communications in Mass Spectrometry. 2012;26(15):1705–1710. DOI:10.1002/rcm.6280. https://www.pharmjournal.ru/jour/article/view/1807 doi:10.33380/2305-2066-2024-13-2-1638 Authors who publish with this journal agree to the following terms:Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.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), with an acknowledgement of its initial publication in this journal.Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) 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). Авторы, публикующие в данном журнале, соглашаются со следующим:Авторы сохраняют за собой авторские права на работу и предоставляют журналу право первой публикации работы на условиях лицензии Creative Commons Attribution License, которая позволяет другим распространять данную работу с обязательным сохранением ссылок на авторов оригинальной работы и оригинальную публикацию в этом журнале.Авторы сохраняют право заключать отдельные контрактные договорённости, касающиеся не-эксклюзивного распространения версии работы в опубликованном здесь виде (например, размещение ее в институтском хранилище, публикацию в книге), со ссылкой на ее оригинальную публикацию в этом журнале.Авторы имеют право размещать их работу в сети Интернет (например в институтском хранилище или персональном сайте) до и во время процесса рассмотрения ее данным журналом, так как это может привести к продуктивному обсуждению и большему количеству ссылок на данную работу (См. The Effect of Open Access). Drug development & registration; Том 13, № 2 (2024); 133-141 Разработка и регистрация лекарственных средств; Том 13, № 2 (2024); 133-141 2658-5049 2305-2066 валидация high-performance liquid chromatography mass spectrometry HPLC-MS/MS validation высокоэффективная жидкостная хроматография масс-спектрометрия ВЭЖХ-МС/МС info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 2024 ftjrirls https://doi.org/10.33380/2305-2066-2024-13-2-163810.3390/molecules2508180110.29296/25419218-2021-06-0310.1002/ptr.632710.1016/j.jpba.2020.11370410.1007/s10517-018-4159-x10.1016/j.fitote.2011.04.00910.1093/ehjacc/zuab020.10710.1016/j.foodchem.2023.13600610 2024-06-10T14:05:40Z Introduction. Polyprenols are known as a class of natural long-chain isoprenoid alcohols, which are natural bioregulators that directly participate in the synthesis of cell membrane glycoproteins. Their hepatoprotective activity is proven, as well other types of their pharmacological effects are known, which is the reason of significant interest in these substances as a promising medicinal product. It is non-trivial task to determine the sum of polyprenols in extracts as include design and implementation of accurate reproducible analytical methods, which will subsequently be used in standardization.Aim. Development and validation of the chromatographic-mass spectrometric technique for polyprenols identification and their quantitative assessment.Materials and methods. Chromatographic separation of polyprenols was performed by using an HPLC Agilent 1260 Infinity II (Agilent Technologies, США); with the mixture of methanol, n-hexane, propanol-2, and aqueous ammonium acetate solution as eluent in gradient mode. An AB Sciex QTrap® 3200MD (AB Sciex Pte. Ltd., Singapore) triple quadrupole mass spectrometer was used as a detector, with the registration of polyprenols adducts.Results and discussion. The conditions for chromatographic separation and detection of polyprenols were identified. The developed technique was validated for the following characteristics: specificity, limit of detection, limit of quantification, linearity, accuracy, precision, range of application, and stability.Conclusion. It was determined the content of polyprenols in the substance recieved from Ginkgo biloba L. and Picea abies L. The developed technique can be used in the future to assess the content of polyprenols in drug products or pharmaceutical substances. Введение. Полипренолы представляют собой класс длинноцепочечных изопреноидных спиртов природного происхождения. Полипренолы являются природными биорегуляторами, принимающими непосредственное участие в синтезе гликопротеинов клеточных мембран, обладают выраженной гепатопротекторной ... Article in Journal/Newspaper Sibirica Drug development & registration Conservation Biology 27 3 552 559

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