foodsystFood systemsПищевые системы2618-97712618-7272Федеральный научный центр пищевых систем им. В.М. Горбатова РАН10.21323/2618-9771-2024-7-4-535-542foodsyst-624Research ArticleСтатьиMethods of extraction, separation and identification of cyclic peptides from flaxseed (Linum usitatissimum L.): A reviewМетоды экстракции, разделения и идентификации циклических пептидов из льна масличного (Linum usitatissimum L.): Обзорhttps://orcid.org/0000-0003-2166-006XСоболевР. В.SobolevR. V.

Соболев Роман Владимирович — кандидат технических наук, инженер-исследователь, лаборатория пищевых биотехнологий и специализированных продуктов

109240, Москва, Устьинский проезд, 2/14

Tel. +7–495–698–53–89

Roman V.  Sobolev, Candidate of Technical Sciences, Research Engineer, Laboratory of Food Biotechnologies and Specialized Products

2/14, Ustinsky proyezd, 109240, Moscow

Tel: +7–495–698–53–89

sobolevrv@bk.ruhttps://orcid.org/0000-0003-2819-6001СоколовИ. Е.SokolovI. E.

Соколов Илья Евгеньевич — научный сотрудник, лаборатория пищевой токсикологии и оценки безопасности нанотехнологий

109240, Москва, Устьинский проезд, 2/14

Tel. +7–495–698–53–89

Ilya E. Sokolov, Researcher, Laboratory of Food Toxicology and Safety Assessment of Nanotechnology

2/14, Ustinsky proyezd, 109240, Moscow

Tel: +7–495–698–53–89

sokolov.iliya1993@gmail.comhttps://orcid.org/0000-0001-9755-6002ПетровН. А.PetrovN. A.

Петров Никита Александрович — кандидат биологических наук, научный сотрудник, лаборатория пищевых биотехнологий и специализированных продуктов

109240, Москва, Устьинский проезд, 2/14

Tel. +7–495–698–53–89

Nikita A. Petrov, Candidate of Biological Sciences, Researcher, Laboratory of Food Biotechnologies and Specialized Products

2/14, Ustinsky proyezd, 109240, Moscow

Tel: +7–495–698–53–89

petrov@ion.ruhttps://orcid.org/0000-0002-5911-610XСаркисянВ. А.SarkisyanV. А.

Саркисян Варужан Амбарцумович  — кандидат биологических наук, старший научный сотрудник, лаборатория пищевых биотехнологий и специализированных продуктов

109240, Москва, Устьинский проезд, 2/14

Tel. +7–495–698–53–89

Varuzhan A. Sarkisyan, Candidate of Biological Sciences, Senior Researcher, Laboratory of Food Biotechnologies and Specialized Products

2/14, Ustinsky proyezd, 109240, Moscow

Tel: +7–495–698–53–89

sarkisyan@ion.ruhttps://orcid.org/0000-0001-9821-192XКочетковаА. А.KochetkovaA. A.

Кочеткова Алла Алексеевна  — доктор технических наук, профессор, член-корреспондент РАН, заведующий лабораторией пищевых биотехнологий и специализированных продуктов

109240, Москва, Устьинский проезд, 2/14

Tel. +7–495–698–53–89

Alla A. Kochetkova, Doctor of Technical Sciences, Professor, Corresponding Member of the Russian Academy of Sciences, Head of the Laboratory of Food Biotechnologies and Specialized Products

2/14, Ustinsky proyezd, 109240, Moscow

Tel: +7–495–698–53–89

kochetkova@ion.ruФедеральный исследовательский центр питания, биотехнологии и безопасности пищиРоссияFederal Research Centre of Nutrition, Biotechnology and Food SafetyRussian Federation20240102202574535542Copyright © Sobolev R.V., Sokolov I.E., Petrov N.A., Sarkisyan V.А., Kochetkova A.A., 20252025Соболев Р.В., Соколов И.Е., Петров Н.А., Саркисян В.А., Кочеткова А.А.Sobolev R.V., Sokolov I.E., Petrov N.A., Sarkisyan V.А., Kochetkova A.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.fsjour.com/jour/article/view/624

Oilseed flax (Linum usitatissimum L.) is a valuable crop characterized by a high content of fats, dietary fiber, protein and various biologically active substances, in particular cyclopeptides. Cyclic peptides are a group of cyclic hydrophobic peptides consisting of eight to ten amino acids with a molecular weight in the range of 950–2300 Da. Flax oil and seeds contain from 0.1 to 0.3% cyclopeptides, which can exhibit antioxidant, anti-inflammatory, immunosuppressive, antihypertensive and antitumor activity. The aim of this review was to systematize and summarize the available literature data on methods of extraction, separation and identification of cyclopeptides from flaxseed oil. It was found that the main methods for obtaining cyclopeptides are solid-liquid, liquid-liquid or solid-phase extraction. Commonly used solvents include methanol, hexane, ethyl acetate, dichloromethane, acetonitrile and deionized water. Preparative flash chromatography on silica gel or polymer adsorbents is used to purify and concentrate cyclopeptides, and high-performance liquid chromatography (HPLC) is used to obtain individual standards. The most commonly used stationary phases are non-polar modified sorbents — octadecyl (C18) and phenylhexyl functional groups. Identification is carried out using instrumental methods of analysis: IR spectroscopy, NMR, HPLC with a diode array detector (HPLC-PDA/DAD), high-resolution tandem mass spectrometry with electrospray ionization (ESI-HR-MS/MS). For the qualitative and quantitative determination of cyclopeptides, the HPLC with a diode array detector at a wavelength of 214 nm is sufficient. In turn, mass spectral methods, including tandem mass spectrometry, make it possible to confirm the qualitative composition and establish the amino acid sequence of cyclic peptides.

Лен масличный (Linum usitatissimum L.) является ценнейшей культурой, характеризующейся высоким содержанием жиров, пищевых волокон, белка, а также различных биологически активных веществ, в частности циклических пептидов. Циклические пептиды — группа циклических гидрофобных пептидов, состоящих из восьми-десяти аминокислот с молекулярной массой в диапазоне 950–2300 Да. Масло и семена льна содержат в своем составе от 0,1 до 0,3% циклических пептидов, способных проявлять антиоксидантную, противовоспалительную, иммуносупрессивную, антигипертензивную и противоопухолевую активности. Цель настоящего обзора заключалась в систематизации и обобщении имеющихся литературных данных о методах экстракции, разделения и идентификации циклических пептидов из масла семян льна масличного. Установлено, что основными методами получения циклических пептидов являются экстракции типа «твердое вещество — жидкость», «жидкость — жидкость» или «твердофазная» экстракция. В качестве растворителей обычно применяют метанол, гексан, этилацетат, дихлорметан, ацетонитрил и деионизованную воду. Для очистки и концентрирования циклических пептидов используют препаративную флеш-хроматографию на силикагеле или полимерных адсорбентах, для получения индивидуальных стандартов — высокоэффективную жидкостную хроматографию (ВЭЖХ). В качестве неподвижной фазы наиболее часто используют неполярные модифицированные сорбенты — октадецильные (С18) и фенилгексильные функциональные группы. Идентификацию проводят с использованием инструментальных методов анализа: ИКспектроскопии, ЯМР, ВЭЖХ с детектором типа диодная матрица (HPLC-PDA/DAD), тандемной масс-спектрометрией высокого разрешения с ионизацией электрораспылением (ESI-HR-MS/MS). Для качественного и количественного определения циклических пептидов достаточным является осуществление метода ВЭЖХ с детектором типа диодная матрица на длине волны 214 нм. В свою очередь, масс-спектральные методы, в том числе тандемная масс-спектрометрия, позволяют подтвердить качественный состав и установить аминокислотную последовательность циклических пептидов.

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The authors declare that there are no conflicts of interest present.