ovoshchiОвощи РоссииVegetable crops of Russia2072-91462618-7132Федеральный научный центр овощеводства10.18619/2072-9146-2024-4-54-60ovoshchi-2450Research ArticleСАДОВОДСТВО, ОВОЩЕВОДСТВО, ВИНОГРАДАРСТВО И ЛЕКАРСТВЕННЫЕ КУЛЬТУРЫHORTICULTURE, VEGETABLE PRODUCTION, VITICULTURE AND MEDICINAL CROPSКачественный состав фенольных соединений листьев растений Rhodiola rosea L., интродуцированных в условиях Московской областиQualitative composition of phenolic compounds in leaves of Rhodiola rosea L. plants introduced in the conditions of the Moscow regionhttps://orcid.org/0000-0003-4642-651XКрольТ. А.KrolT. A.

Татьяна Анатольевна Кроль – кандидат с.-х. наук, ведущий научный сотрудник

117216, г. Москва, ул. Грина, д. 7

Tatiana A. Krol – Cand. Sci. (Agriculture)

7, Grin street, Moscow, 117216

tatianakroll1@gmail.comhttps://orcid.org/0000-0002-8383-9965ОсиповВ. И.OssipovV. I.

Владимир Ионович Осипов – доктор биол. наук, главный научный сотрудник

117216, г. Москва, ул. Грина, д. 7

Vladimir I. Ossipov – Dr. Sc. (Biology)

7, Grin street, Moscow, 117216

ossipov@utu.fihttps://orcid.org/0000-0002-1228-0594БалеевД. Н.BaleevD. N.

Дмитрий Николаевич Балеев – кандидат с.-х. наук, зав. лаб.

117216, г. Москва, ул. Грина, д. 7

Dmitriy N. Baleev – Cand. Sci. (Agriculture)

7, Grin street, Moscow, 117216

dbaleev@gmail.comФедеральное государственное бюджетное научное учреждение «Всероссийский Институт Лекарственных и Ароматических Растений» (ФГБНУ ВИЛАР)РоссияAll-Russian scientific research Institute of medicinal and aromatic plantsRussian Federation202409072024045460Copyright © Кроль Т.А., Осипов В.И., Балеев Д.Н., 20242024Кроль Т.А., Осипов В.И., Балеев Д.Н.Krol T.A., Ossipov V.I., Baleev D.N.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.vegetables.su/jour/article/view/2450Актуальность

Актуальность. Rhodiola rosea L., многолетнее травянистое растение семейства Crassulaceae, корни и корневища которого характеризуются присутствием разнообразных биологически активных соединений. Данный вид включен в Государственную фармакопею Российской Федерации. Лекарственные препараты, полученные из корней R. rosea, широко применяют в качестве адаптогенов, общетонизирующих и антистрессовых средств. В отличие от корней, биологически активные соединения листьев R. rosea исследованы в меньшей степени. На территории ботанического сада лекарственных растений ФГБНУ ВИЛАР произрастает интродуцированная популяция R. rosea. Изучается возможность культивирования данного вида в условиях Московской области.

Материал и методика

Материал и методика. Целью нашей работы было изучение состава фенольных соединений листьев R. rosea из биоколлекции ФГБНУ ВИЛАР с использованием ультра-эффективной жидкостной хроматографии. Экстракцию проводили 80% ацетоном. Для качественного анализа фенольных соединений использовали ультра-эффективную жидкостную хроматографическую систему в комбинации с фотодиодным и масс-спектрометрическим детекторами. Идентификацию проводили по данным УФ- и масс-спектрометрии.

Результаты

Результаты. В результате проведенного УЭЖХ-ДД-МС анализа в листьях R. rosea были обнаружены пики 20 фенольных соединений, из них 19 соединений были предварительно идентифицированы. В экстракте листьев содержалось восемь фенольных соединений из группы галлоил-глюкоз (три изомера моногаллоил-глюкозы, тригаллоил-глюкоза, два изомера тетрагаллоил-глюкозы, два изомера пентагаллоил-глюкозы), два соединения, относящиеся к галлотаннинам (два изомера гексагаллоил-глюкозы), пять флавоноидов (четыре производных гербацетина и одно госсипетина), фенольные кислоты (кофеоил-яблочная и феруловая кислоты), а также арбутин и эскулетин. Показано, что биологически активные вещества R. rosea, дают перспективу использования листьев в качестве сырья, для разработки препаратов растительного происхождения противовоспалительного, противовирусного и противоопухолевого действия.

Relevance

Relevance. Rhodiola rosea L. is a perennial herbaceous plant from the Crassulaceae family. The roots and rhizomes of R. rosea contain a range of biologically active compounds. This species is included in the State Pharmacopoeia of the Russian Federation. Medicinal preparations derived from them are widely used as adaptogens, general tonic and anti-stress agents. While the roots have been extensively studied, less attention has been given to the biologically active compounds found in the leaves of R. rosea. An introduced population of R. rosea grows on the territory of the botanical garden of medicinal plants of the All-Russian scientific research Institute of medicinal and aromatic plants (VILAR). The possibility of cultivating this species in the conditions of the Moscow region is being studied.

Material and Methodology

Material and Methodology. The objective of this study was to investigate the composition of phenolic compounds in R. rosea leaves from VILAR biocollection using ultra-efficient liquid chromatography combined with mass spectrometry. Extraction was carried out with 80% acetone. An ultra-high performance liquid chromatographic system with a photodiode array detector and mass spectrometer was used for the analysis of phenolic compounds. Identification was carried out using UV- and mass spectrometry data.

Results

Results. As a result of UPLC-DD-MS analysis, peaks of 20 phenolic compounds were detected in R. rosea leaves, of which 19 compounds were tentatively identified. The leaf extract contained eight phenolic compounds from the group of galloyl-glucoses (three isomers of monogalloyl-glucose, trigalloyl-glucose, two isomers of tetragalloyl-glucose, two isomers of pentagalloyl-glucose), two gallotannins (isomers of hexagalloyl-glucose), five flavonoids (four herbacetin derivatives and one gossypetin), phenolic acids (caffeoyl-malic and ferulic acids), arbutin and esculetin. It has been shown that the biologically active substances of R. rosea provide prospects for the use of leaves as raw materials for the development of herbal preparations with anti-inflammatory, antiviral and antitumor effects.

Лекарственные растенияRhodiola rosea L.ультра-эффективная жидкостная хроматографияфенольные соединениягаллоил-глюкозыгаллотанниныфенольные кислотыфлавоноидыmedicinal plantsRhodiola rosea L.ultra-performance liquid chromatographyphenolic compoundsgalloylglucosesgallotanninsphenolic acidsflavonoidsReferencesAlperth F., Turek I., Weiss S., Vogt D., Bucar F. Qualitative and quantitative analysis of different Rhodiola rosea rhizome extracts by UHPLCDAD-ESI-MSn. Scientia Pharmaceutica. 2019;87(2):8. https://doi.org/10.3390/scipharm87020008Alperth F., Turek I., Weiss S., Vogt D., Bucar F. Qualitative and quantitative analysis of different Rhodiola rosea rhizome extracts by UHPLCDAD-ESI-MSn. Scientia Pharmaceutica. 2019;87(2):8. https://doi.org/10.3390/scipharm87020008Dorogina O.V., Kuban I.N., Achimova A.A., Williams N., Lashchinskiy N.N., Zhmud E.V. Morphometric characteristics and genetic issr marker variability in Rhodiola rosea L. (Crassulaceae) in different ecological and geographic conditions in the Altai Republic. International Journal of Molecular Sciences. 2023;24(20):15224. https://doi.org/10.3390/ijms242015224Dorogina O.V., Kuban I.N., Achimova A.A., Williams N., Lashchinskiy N.N., Zhmud E.V. Morphometric characteristics and genetic issr marker variability in Rhodiola rosea L. (Crassulaceae) in different ecological and geographic conditions in the Altai Republic. International Journal of Molecular Sciences. 2023;24(20):15224. https://doi.org/10.3390/ijms242015224Bernatoniene J., Jakstas V., Kopustinskiene D. M. Phenolic compounds of Rhodiola rosea L. as the potential alternative therapy in the treatment of chronic diseases. International journal of molecular sciences. 2023;24(15):12293. https://doi.org/10.3390/ijms241512293Bernatoniene J., Jakstas V., Kopustinskiene D. M. Phenolic compounds of Rhodiola rosea L. as the potential alternative therapy in the treatment of chronic diseases. International journal of molecular sciences. 2023;24(15):12293. https://doi.org/10.3390/ijms241512293Petsalo A., Jalonen J., Tolonen A. Identification of flavonoids of Rhodiola rosea by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A. 2006;1112(1-2):224-231. https://doi.org/10.1016/j.chroma.2005.11.056Petsalo A., Jalonen J., Tolonen A. Identification of flavonoids of Rhodiola rosea by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A. 2006;1112(1-2):224-231. https://doi.org/10.1016/j.chroma.2005.11.056Адамов Г.В., Анели Д.Н., Антоненко М.С. и др. Атлас лекарственных растений России. Изд. 2-е перераб. и дополненное. М.: Наука, 2021. С. 446-449. https://elibrary.ru/dqvikrAtlas of medicinal plants of Russia. Moscow, Nauka Publ., 2021. 446–449 p. https://elibrary.ru/dqvikrZakharenko A.M. Razgonova M.P., Pikula K.S., Golokhvast K.S. Simultaneous determination of 78 compounds of Rhodiola rosea extract by supercritical CO2-extraction and HPLC-ESI-MS/MS spectrometry. Biochemistry Research International. 2021;2021. https://doi.org/10.1155/2021/9957490Zakharenko A.M. Razgonova M.P., Pikula K.S., Golokhvast K.S. Simultaneous determination of 78 compounds of Rhodiola rosea extract by supercritical CO2-extraction and HPLC-ESI-MS/MS spectrometry. Biochemistry Research International. 2021;2021. https://doi.org/10.1155/2021/9957490Государственная Фармакопея Российской Федерации XIV изд. - М., 2018 [Электронный ресурс]. URL: https://pharmacopoeia.ru/gosudarstvennaya-farmakopeya-14-izdaniya (дата обращения: 20.02.2024).State Pharmacopoeia of the Russian Federation. М., 2018. [Electronic resource] URL: https://pharmacopoeia.ru/gosudarstvennaya-farmakopeya-14-izdaniya (Accessed 20.02.2024).Zomborszki P.Z., Kúsz N., Csupor D., Peschel W. Rhodiosin and herbacetin in Rhodiola rosea preparations: additional markers for quality control. Pharmaceutical biology. 2019;57(1):295-305. https://doi.org/10.1080/13880209.2019.1577460Zomborszki P.Z., Kúsz N., Csupor D., Peschel W. Rhodiosin and herbacetin in Rhodiola rosea preparations: additional markers for quality control. Pharmaceutical biology. 2019;57(1):295-305. https://doi.org/10.1080/13880209.2019.1577460Li Y., Pham V., Bui M. Song L., Wu C., Walia A., Uchio E., Smith-Liu F., Zi X. Rhodiola rosea L.: an herb with anti-Stress, anti-Aging, and immunostimulating properties for cancer chemoprevention. Current pharmacology reports. 2017;(3):384-395. https://doi.org/10.1007/s40495-017-0106-1Li Y., Pham V., Bui M. Song L., Wu C., Walia A., Uchio E., Smith-Liu F., Zi X. Rhodiola rosea L.: an herb with anti-Stress, anti-Aging, and immunostimulating properties for cancer chemoprevention. Current pharmacology reports. 2017;(3):384-395. https://doi.org/10.1007/s40495-017-0106-1Pu W. L., Zhang M. Y., Bai R. Y., Sun L. K., Li W. H., Yu Y. L., Zhang Y., Song L., Wang Z. X., Peng Y. F., Shi H., Zhou K., Li T. X. Anti-inflammatory effects of Rhodiola rosea L.: A review. Biomedicine & Pharmacotherapy. 2020;(121):109552. https://doi.org/10.1016/j.biopha.2019.109552Pu W. L., Zhang M. Y., Bai R. Y., Sun L. K., Li W. H., Yu Y. L., Zhang Y., Song L., Wang Z. X., Peng Y. F., Shi H., Zhou K., Li T. X. Anti-inflammatory effects of Rhodiola rosea L.: A review. Biomedicine & Pharmacotherapy. 2020;(121):109552. https://doi.org/10.1016/j.biopha.2019.109552Sist P., Tramer F., Lorenzon P., Urbani R., Vrhovsek U., Bernareggi A., Sciancalepore M. Rhodiola rosea, a protective antioxidant for intense physical exercise: An in vitro study. Journal of Functional Foods. 2018;(48):27-36. https://doi.org/10.1016/j.jff.2018.06.022Sist P., Tramer F., Lorenzon P., Urbani R., Vrhovsek U., Bernareggi A., Sciancalepore M. Rhodiola rosea, a protective antioxidant for intense physical exercise: An in vitro study. Journal of Functional Foods. 2018;(48):27-36. https://doi.org/10.1016/j.jff.2018.06.022Nikolaichuk H., Typek R., Gnat S., Studziński M., Choma I. M. Effectdirected analysis as a method for quality and authenticity estimation of Rhodiola rosea L. preparations. Journal of Chromatography A. 2021;(1649):462217. https://doi.org/10.1016/j.chroma.2021.462217Nikolaichuk H., Typek R., Gnat S., Studziński M., Choma I. M. Effectdirected analysis as a method for quality and authenticity estimation of Rhodiola rosea L. preparations. Journal of Chromatography A. 2021;(1649):462217. https://doi.org/10.1016/j.chroma.2021.462217Tang Y., Friesen J. B., Nikolić D. S., Lankin D. C., McAlpine J. B., Chen S.-N., Pauli G. F. Tandem of countercurrent separation and qHNMR enables gravimetric analyses: absolute quantitation of the Rhodiola rosea metabolome. Analytical Chemistry. 2021;93(34):11701–11709. https://doi.org/10.1021/acs.analchem.1c01554.Tang Y., Friesen J. B., Nikolić D. S., Lankin D. C., McAlpine J. B., Chen S.-N., Pauli G. F. Tandem of countercurrent separation and qHNMR enables gravimetric analyses: absolute quantitation of the Rhodiola rosea metabolome. Analytical Chemistry. 2021;93(34):11701–11709. https://doi.org/10.1021/acs.analchem.1c01554.Chiang H.M., Chen H.C., Wu C.S., Wu P.Y., Wen K.C. Rhodiola plants: chemistry and biological activity. Journal of Food and Drug Analysis. 2015;23(3):359-369. https://doi.org/10.1016/j.jfda.2015.04.007Chiang H.M., Chen H.C., Wu C.S., Wu P.Y., Wen K.C. Rhodiola plants: chemistry and biological activity. Journal of Food and Drug Analysis. 2015;23(3):359-369. https://doi.org/10.1016/j.jfda.2015.04.007Polumackanycz M., Konieczynski P., Orhan I.E., Abaci N., Viapiana A. Chemical composition, antioxidant and anti-enzymatic activity of golden root (Rhodiola rosea L.) commercial samples. Antioxidants. 2022;11(5):919. https://doi.org/10.3390/antiox11050919Polumackanycz M., Konieczynski P., Orhan I.E., Abaci N., Viapiana A. Chemical composition, antioxidant and anti-enzymatic activity of golden root (Rhodiola rosea L.) commercial samples. Antioxidants. 2022;11(5):919. https://doi.org/10.3390/antiox11050919Marchev A.S., Aneva I.Y., Koycheva I.K., Georgiev M.I. Phytochemical variations of Rhodiola rosea L. wild-grown in Bulgaria. Phytochemistry Letters. 2017;(20):386-390. https://doi.org/10.1016/j.phytol.2016.12.030.Marchev A.S., Aneva I.Y., Koycheva I.K., Georgiev M.I. Phytochemical variations of Rhodiola rosea L. wild-grown in Bulgaria. Phytochemistry Letters. 2017;(20):386-390. https://doi.org/10.1016/j.phytol.2016.12.030.Olennikov D.N., Chirikova N.K. New metabolites of Rhodiola rosea L. glycosides of herbacetin and gossypetin. Chemistry of Natural Compounds. 2022;58(6):1014-1020.Olennikov D.N., Chirikova N.K. New metabolites of Rhodiola rosea L. glycosides of herbacetin and gossypetin. Chemistry of Natural Compounds. 2022;58(6):1014-1020.Olennikov D.N., Chirikova N.K., Vasilieva A.G., Fedorov I.A. LC-MS profile, gastrointestinal and gut microbiota stability and antioxidant activity of Rhodiola rosea herb metabolites: A comparative study with subterranean organs. Antioxidants. 2020;9(6):526. https://doi.org/10.3390/antiox9060526Olennikov D.N., Chirikova N.K., Vasilieva A.G., Fedorov I.A. LC-MS profile, gastrointestinal and gut microbiota stability and antioxidant activity of Rhodiola rosea herb metabolites: A comparative study with subterranean organs. Antioxidants. 2020;9(6):526. https://doi.org/10.3390/antiox9060526Dong T., Liu H., Sha Y., Sun L. A comparative study of phytochemical metabolites and antioxidant properties of Rhodiola. Arabian Journal of Chemistry. 2023;16(1):104420. https://doi.org/10.1016/j.arabjc.2022.104420Dong T., Liu H., Sha Y., Sun L. A comparative study of phytochemical metabolites and antioxidant properties of Rhodiola. Arabian Journal of Chemistry. 2023;16(1):104420. https://doi.org/10.1016/j.arabjc.2022.104420Савченко О.М., Бабаева Е.Ю. Изучение фенологии и семенной продуктивности растений родиолы розовой в Центральном районе Нечерноземной зоны РФ. Юг России: экология, развитие. 2021;16(1):26-35. https://doi.org/10.18470/1992-1098-2021-1-98-109 https://elibrary.ru/bnphsySavchenko O.M., Babaeva E.Yu. Study of the phenology and seed productivity of golden root (Sedum roseum (L.) Scop.) in the central region of the non-chernozem zone of the Russian Federation. South of Russia: ecology, development. 2021;16(1):26-35. https://doi.org/10.18470/1992-1098-2021-1-98-109 https://elibrary.ru/bnphsyСавченко О. М., Цыбулько Н.С. Экзогенная регуляция биопродуктивности родиолы розовой (Sedum roseum (L.) Scop.). Агрохимический вестник. 2021;(3):52-56. https://doi.org/10.24412/1029-2551-2021-3-011 https://elibrary.ru/ovuopnSavchenko O.M., Tsybulko N.S. Exogenous regulation of biological productivity of the golden root (Sedum roseum (L.) Scop.). Agrochemical Herald. 2021;(3):52-56. https://doi.org/10.24412/1029- 2551-2021-3-011 https://elibrary.ru/ovuopnBrinckmann J.A., Cunningham A.B., Harter D.E.V. Running out of time to smell the roseroots: Reviewing threats and trade in wild Rhodiola rosea L. Journal of Ethnopharmacology. 2021;(269):113710. https://doi.org/10.1016/j.jep.2020.113710Brinckmann J.A., Cunningham A.B., Harter D.E.V. Running out of time to smell the roseroots: Reviewing threats and trade in wild Rhodiola rosea L. Journal of Ethnopharmacology. 2021;(269):113710. https://doi.org/10.1016/j.jep.2020.113710Савченко О.М. Эффективность микроудобрений для повышения семенной продуктивности и качества семян родиолы розовой в зависимости от условий сезона вегетации. Аграрная Россия. 2020;(2):7- 10. https://doi.org/10.30906/1999-5636-2020-2-7-10Savchenko O.M. Efficiency of microfertilizers to increase seed productivity and quality of Rhodiola rosea L. seeds depending on the growing season conditions. Agrarian Russia. 2020;(2):7-10. https://doi.org/10.30906/1999-5636-2020-2-7-10Савченко О.М., Цыбулько Н.С., Саматадзе Т.Е. Сравнительное изучение представителей различных популяций вида Sedum roseum (L.) Scop. при возделывании в культуре. Юг России: экология, развитие. 2023;18(2(67)):21-32. https://doi.org/10.18470/1992-1098-2023-2- 21-32 https://elibrary.ru/dzcjyoSavchenko O.M., Tsybulko N.S., Samatadze T.E. Comparative study of representatives of different populations of Sedum roseum (L.) Scop growing in conditions of field crop rotation. South of Russia: ecology, development. 2023;18(2(67)):21-32. https://doi.org/10.18470/1992-1098-2023-2-21-32 https://elibrary.ru/dzcjyoEngstrom M.T., Palijarvi M., Salminen J. P. Rapid fingerprint analysis of plant extracts for ellagitannins, gallic acid, and quinic acid derivatives and quercetin-, kaempferol-and myricetin-based flavonol glycosides by UPLC-QqQ-MS/MS. Journal of agricultural and food chemistry. 2015;63(16):4068-4079. https://doi.org/10.1021/acs.jafc.5b00595Engstrom M.T., Palijarvi M., Salminen J. P. Rapid fingerprint analysis of plant extracts for ellagitannins, gallic acid, and quinic acid derivatives and quercetin-, kaempferol-and myricetin-based flavonol glycosides by UPLC-QqQ-MS/MS. Journal of agricultural and food chemistry. 2015;63(16):4068-4079. https://doi.org/10.1021/acs.jafc.5b00595Wishart D.S., Feunang Y.D., Marcu A., Guo A. C., Liang K., VázquezFresno R., Scalbert A. HMDB 4.0: the human metabolome database for 2018. Nucleic acids research. 2018;46(D1):D608-D617. https://doi.org/10.1093/nar/gkx1089Wishart D.S., Feunang Y.D., Marcu A., Guo A. C., Liang K., VázquezFresno R., Scalbert A. HMDB 4.0: the human metabolome database for 2018. Nucleic acids research. 2018;46(D1):D608-D617. https://doi.org/10.1093/nar/gkx1089Van Diermen D., Pierreclos M., Hostettmann K. Antioxidant phenolic compounds from Sedum dasyphyllum L. Planta Medica. 2009;75(09):PJ49. https://doi.org/10.1055/s-0029-1234854Van Diermen D., Pierreclos M., Hostettmann K. Antioxidant phenolic compounds from Sedum dasyphyllum L. Planta Medica. 2009;75(09):PJ49. https://doi.org/10.1055/s-0029-1234854Bhardwaj A.K. Singh B., Kaur K., Roshan P., Sharma A., Dolker D., Naryal A., Saxena S., Pati P.K., Chaurasia O.P. In vitro propagation, clonal fidelity and phytochemical analysis of Rhodiola imbricata Edgew: a rare trans-Himalayan medicinal plant. Plant Cell, Tissue and Organ Culture (PCTOC). 2018;135:499-513. https://doi.org/10.1007/s11240-018-1482-xBhardwaj A.K. Singh B., Kaur K., Roshan P., Sharma A., Dolker D., Naryal A., Saxena S., Pati P.K., Chaurasia O.P. In vitro propagation, clonal fidelity and phytochemical analysis of Rhodiola imbricata Edgew: a rare trans-Himalayan medicinal plant. Plant Cell, Tissue and Organ Culture (PCTOC). 2018;135:499-513. https://doi.org/10.1007/s11240-018-1482-xXu T., Lv C., Lu J. The fingerprint and flavonoids contents by HPLC and the UPLC-DAD-Q-TOF-MS analysis of Sedum aizoon L. 多酚. 2019;1(1):23-32.Xu T., Lv C., Lu J. The fingerprint and flavonoids contents by HPLC and the UPLC-DAD-Q-TOF-MS analysis of Sedum aizoon L. 多酚. 2019;1(1):23-32.Moilanen J., Sinkkonen J., Salminen J. P. Characterization of bioactive plant ellagitannins by chromatographic, spectroscopic and mass spectrometric methods. Chemoecology. 2013;(23):165-179. https://doi.org/10.1007/s00049-013-0132-3Moilanen J., Sinkkonen J., Salminen J. P. Characterization of bioactive plant ellagitannins by chromatographic, spectroscopic and mass spectrometric methods. Chemoecology. 2013;(23):165-179. https://doi.org/10.1007/s00049-013-0132-3Okuda T., Ito H. Tannins of constant structure in medicinal and food plants—hydrolyzable tannins and polyphenols related to tannins. Molecules. 2011;16(3):2191-2217. https://doi.org/10.3390/molecules16032191Okuda T., Ito H. Tannins of constant structure in medicinal and food plants—hydrolyzable tannins and polyphenols related to tannins. Molecules. 2011;16(3):2191-2217. https://doi.org/10.3390/molecules16032191He H.F. Recognition of gallotannins and the physiological activities: from chemical view. Frontiers in Nutrition. 2022;(9):888892. https://doi.org/10.3389/fnut.2022.888892He H.F. Recognition of gallotannins and the physiological activities: from chemical view. Frontiers in Nutrition. 2022;(9):888892. https://doi.org/10.3389/fnut.2022.888892Vu T.T., Kim J.C., Choi Y.H., Choi G.J., Jang K.S., Choi T.H., Yoon T.M., Lee S.W. Effect of gallotannins derived from Sedum takesimense on tomato bacterial wilt. Plant disease. 2013;97(12):1593-1598. https://doi.org/10.1094/PDIS-04-13-0350-REVu T.T., Kim J.C., Choi Y.H., Choi G.J., Jang K.S., Choi T.H., Yoon T.M., Lee S.W. Effect of gallotannins derived from Sedum takesimense on tomato bacterial wilt. Plant disease. 2013;97(12):1593-1598. https://doi.org/10.1094/PDIS-04-13-0350-REMa C., Zhao X., Wang P., Jia P., Zhao X.F., Xiao C.N., Zheng X.H. Metabolite characterization of Penta-O-galloyl-β-D-glucose in rat biofluids by HPLC-QTOF-MS. Chinese Herbal Medicines. 2018;10(1):73-79. https://doi.org/10.1016/j.chmed.2018.01.002Ma C., Zhao X., Wang P., Jia P., Zhao X.F., Xiao C.N., Zheng X.H. Metabolite characterization of Penta-O-galloyl-β-D-glucose in rat biofluids by HPLC-QTOF-MS. Chinese Herbal Medicines. 2018;10(1):73-79. https://doi.org/10.1016/j.chmed.2018.01.002Torres-León C., Ventura-Sobrevilla J., Serna-Cock L., AscacioValdés J.A., Contreras-Esquivel J., Aguilar C.N. Pentagalloylglucose (PGG): A valuable phenolic compound with functional properties. Journal of Functional Foods. 2017;(37):176-189. https://doi.org/10.1016/j.jff.2017.07.045Torres-León C., Ventura-Sobrevilla J., Serna-Cock L., AscacioValdés J.A., Contreras-Esquivel J., Aguilar C.N. Pentagalloylglucose (PGG): A valuable phenolic compound with functional properties. Journal of Functional Foods. 2017;(37):176-189. https://doi.org/10.1016/j.jff.2017.07.045Wen C., Dechsupa N., Yu Z., Zhang X., Liang S., Lei X., Xu T., Gao X., Hu Q., Innuan P., Kantapan J., Lü M. Pentagalloyl Glucose: A Review of Anticancer Properties, Molecular Targets, Mechanisms of Action, Pharmacokinetics, and Safety Profile. Molecules. 2023;28(12):4856. https://doi.org/10.3390/molecules28124856Wen C., Dechsupa N., Yu Z., Zhang X., Liang S., Lei X., Xu T., Gao X., Hu Q., Innuan P., Kantapan J., Lü M. Pentagalloyl Glucose: A Review of Anticancer Properties, Molecular Targets, Mechanisms of Action, Pharmacokinetics, and Safety Profile. Molecules. 2023;28(12):4856. https://doi.org/10.3390/molecules28124856Chen R.H., Yang L.J., Hamdoun S., Chung S.K., Lam C.W.-K., Zhang K.X., Guo, X., Xia, C., Law B.Y.K., Wong V.K.W. 1,2,3,4,6- Pentagalloyl Glucose, a RBD-ACE2 Binding Inhibitor to Prevent SARS-CoV-2 Infection. Frontiers in Pharmacology. 2021;12:634176. https://doi.org/10.3389/fphar.2021.634176Chen R.H., Yang L.J., Hamdoun S., Chung S.K., Lam C.W.-K., Zhang K.X., Guo, X., Xia, C., Law B.Y.K., Wong V.K.W. 1,2,3,4,6- Pentagalloyl Glucose, a RBD-ACE2 Binding Inhibitor to Prevent SARS-CoV-2 Infection. Frontiers in Pharmacology. 2021;12:634176. https://doi.org/10.3389/fphar.2021.634176Hwang J. K., Kong T. W., Baek N. I., Pyun, Y. R. α-Glycosidase inhibitory activity of hexagalloylglucose from the galls of Quercus infectoria. Planta Medica. 2000;66(03):273-274. https://doi.org/10.1055/с-2000-8569Hwang J. K., Kong T. W., Baek N. I., Pyun, Y. R. α-Glycosidase inhibitory activity of hexagalloylglucose from the galls of Quercus infectoria. Planta Medica. 2000;66(03):273-274. https://doi.org/10.1055/с-2000-8569Sylla T., Pouységu L., Da Costa G., Deffieux D., Monti J. P., Quideau S. Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer’s Amyloid β-Peptide Aggregation. Angewandte Chemie International Edition. 2015;54(28):8217-8221. https://doi.org/10.1002/anie.201411606Sylla T., Pouységu L., Da Costa G., Deffieux D., Monti J. P., Quideau S. Gallotannins and Tannic Acid: First Chemical Syntheses and In Vitro Inhibitory Activity on Alzheimer’s Amyloid β-Peptide Aggregation. Angewandte Chemie International Edition. 2015;54(28):8217-8221. https://doi.org/10.1002/anie.201411606Mizuno T., Uchiyama N., Tanaka S., Nakane T., Devkota H. P., Fujikawa K., Kawahara N., Iwashina T. Flavonoids from Sedum japonicum subsp. oryzifolium (Crassulaceae). Molecules. 2022;27(21):7632. https://doi.org/10.3390/molecules27217632Mizuno T., Uchiyama N., Tanaka S., Nakane T., Devkota H. P., Fujikawa K., Kawahara N., Iwashina T. Flavonoids from Sedum japonicum subsp. oryzifolium (Crassulaceae). Molecules. 2022;27(21):7632. https://doi.org/10.3390/molecules27217632Iwashina T., Nakane T., Devkota H. P. Flavonoids from the leaves and stems of Rhodiola ishidae (Crassulaceae). Biochemical Systematics and Ecology. 2023;(107):104622. https://doi.org/10.1016/j.bse.2023.104622Iwashina T., Nakane T., Devkota H. P. Flavonoids from the leaves and stems of Rhodiola ishidae (Crassulaceae). Biochemical Systematics and Ecology. 2023;(107):104622. https://doi.org/10.1016/j.bse.2023.104622Olennikov D. N., Chirikova N. K. New flavonol glycosides from Rhodiola quadrifida. Chemistry of Natural Compounds. 2020;(56):1048-1054. https://doi.org/10.1007/s10600-020-03224-7Olennikov D. N., Chirikova N. K. New flavonol glycosides from Rhodiola quadrifida. Chemistry of Natural Compounds. 2020;(56):1048-1054. https://doi.org/10.1007/s10600-020-03224-7Wei X., Zhao Z., Zhong R., Tan X. A comprehensive review of herbacetin: From chemistry to pharmacological activities. Journal of ethnopharmacology. 2021;(279):114356. https://doi.org/10.1016/j.jep.2021.114356Wei X., Zhao Z., Zhong R., Tan X. A comprehensive review of herbacetin: From chemistry to pharmacological activities. Journal of ethnopharmacology. 2021;(279):114356. https://doi.org/10.1016/j.jep.2021.114356Dong X., Guo Y., Xiong C., Sun L. Evaluation of two major Rhodiola species and the systemic changing characteristics of metabolites of Rhodiola crenulata in different altitudes by chemical methods combined with UPLC-QqQ-MS-based metabolomics. Molecules. 2020;25(18):4062. https://doi.org/10.3390/molecules25184062Dong X., Guo Y., Xiong C., Sun L. Evaluation of two major Rhodiola species and the systemic changing characteristics of metabolites of Rhodiola crenulata in different altitudes by chemical methods combined with UPLC-QqQ-MS-based metabolomics. Molecules. 2020;25(18):4062. https://doi.org/10.3390/molecules25184062Yue H., Wang L., Jiang S., Banma C., Jia W., Tao Y., Zhao X. Hypoglycemic effects of Rhodiola crenulata (HK. f. et. Thoms) H. Ohba in vitro and in vivo and its ingredient identification by UPLCtriple-TOF/MS. Food & Function. 2022;139(3):1659-1667. https://doi.org/10.1039/D1FO03436GYue H., Wang L., Jiang S., Banma C., Jia W., Tao Y., Zhao X. Hypoglycemic effects of Rhodiola crenulata (HK. f. et. Thoms) H. Ohba in vitro and in vivo and its ingredient identification by UPLCtriple-TOF/MS. Food & Function. 2022;139(3):1659-1667. https://doi.org/10.1039/D1FO03436G

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