vuzbiochemiИзвестия вузов. Прикладная химия и биотехнологияProceedings of Universities. Applied Chemistry and Biotechnology2227-29252500-1558ИРНИТУ10.21285/2227-2925-2021-11-2-310-317vuzbiochemi-595Research ArticleФИЗИКО-ХИМИЧЕСКАЯ БИОЛОГИЯPHYSICOCHEMICAL BIOLOGYСинтез и биологическая активность N6-маннопиранозиладениновSynthesis and biological activity of N6-mannopyranosyladeninesЧерепановИ. С.CherepanovI. S.

Черепанов Игорь Сергеевич – кандидат химических наук, доцент.

426034, Ижевск, ул. Университетская, 1.

Igor S. Cherepanov - cand. Sci. (chemistry), Associate Professor, Udmurt State University.

1, Universitetskaya St., Izhevsk, 426034.

cherchem@mail.ruКамашеваА. А.KamashevaA. A.

Камашева Анна Александровна – студентка.

426034, Ижевск, ул. Университетская, 1.

Anna A. Kamasheva - Student, Udmurt State University.

1, Universitetskaya St., Izhevsk, 426034.

cherchem@mail.ruКашаповаЭ. И.KashapovaE. I.

Кашапова Эльнара Ильдаровна – студентка.

426034, Ижевск, ул. Университетская, 1.

El'nara I. Kashapova - Student, Udmurt State University.

1, Universitetskaya St., Izhevsk, 426034.

cherchem@mail.ruУдмуртский государственный университетРоссияUdmurt State UniversityRussian Federation202102072021112310317Copyright © Черепанов И.С., Камашева А.А., Кашапова Э.И., 20212021Черепанов И.С., Камашева А.А., Кашапова Э.И.Cherepanov I.S., Kamasheva A.A., Kashapova E.I.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vuzbiochemi.elpub.ru/jour/article/view/595

Выполнен синтез потенциально биоактивных продуктов конденсации аденина с D-маннозой и 6-дезокси+-маннозой (L-рамнозой) в водных и этанольных растворах. На основании данных ИК-Фурье спектроскопии и элементного анализа установлено, что моно-N6-гликозилированные аденины с удовлетворительными выходами выделяются из водных систем, тогда как в этанольных растворах образуются смеси N6, N9-продуктов, а также комплексы последних с ионами меди. Детальный анализ колебательных спектров N6-гликозиладенинов подтверждает строение углеводных фрагментов в виде пиранозных циклов, при этом часть продукта образуется в виде дезоксиаминокетоз. N-рамнозиладенин образуется с более чем вдвое большим выходом по причине более высокой устойчивости рамнозы в отношении побочных реакций. Спектры отражения модельных растворов гликозиладенинов, регистрируемые через 4 суток после приготовления, не обнаруживают полос, характерных для свободного аденина в области 1250-1110 см-1, что свидетельствует о достаточной устойчивости синтезированных продуктов к гидролитическому расщеплению в условиях эксперимента. Биотестирование выделенных продуктов на семенах пшеницы (Triticum aestivum L.) показывает увеличение содержания хлорофиллов в проростках для обоих маннозиладенинов в сравнении с контролем. Уменьшение концентрации синтезированных продуктов в растворах проращивания с 0,1 до 0,001% приводит к усилению накопления фотосинтетических пигментов, при этом для рамнозиладенина данный эффект выражен сильнее. Последнее может быть связано со структурными особенностями углеводных фрагментов, в частности, различия в степени гидроксилирования гликозидных фрагментов. Механизмы трансформации и активного действия N6-замещенных аденинов планируется изучить в дальнейшем.

In this work, potentially bioactive condensation products of adenine with D-mannose and 6-deoxy-L-mannose (L-rhamnose) were synthesized in water and ethanol solutions. According to FTIR spectroscopy and elemental analysis, mono-N6-glycosylated adenines were isolated from water systems in satisfactory yields, while ethanol solutions contained mixtures of N6 and N9-products, as well as complexes of the latter with copper ions. A detailed analysis of the vibrational spectra of N6-glycosyladenines confirmed the structure of carbohydrate fragments in the form of pyranose rings, while some part of the product was obtained in the form of deoxyaminoketosis. N-rhamnosyladenine was formed with a more than double yield because of a higher stability of rhamnose with regard to side reactions. The reflection spectra of model solutions of glycosyladenines, recorded 4 days after preparation, showed no bands characteristic of free adenine in the range of 1250-1110 cm-1, which indicates a sufficient resistance of the synthesized products towards hydrolytic cleavage under experimental conditions. The conducted biotesting of the isolated products on wheat seeds (Triticum aestivum L.) showed an increase in the content of chlorophylls in seedlings for both mannosilade-nines compared to the control. A decrease in the concentration of synthesized products in germination solutions from 0.1 to 0.001% led to an increase in the accumulation of photosynthetic pigments, while this effect was more pronounced for rhamnosyladenine. The latter can be connected with the structural features of car-bohydrate fragments, in particular, the differences in the hydroxylation degree of glucoside fragments. Future research will investigate the mechanisms of transformation and action of N6-substituted adenines.

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