Characteristics of the complex of polyphenol compounds of Yakutian endemic  Dracocephalum jacutense  Peschkova using tandem mass spectrometry

Zh. M. Okhlopkova; Охлопкова Ж. М.; M. P. Razgonova; Разгонова М. П.; P. S. Egorova; Егорова П. С.; K. S. Golokhvast; Голохваст К. С.

doi:10.31857/S0015330322600723

Characteristics of the complex of polyphenol compounds of Yakutian endemic Dracocephalum jacutense Peschkova using tandem mass spectrometry

Авторлар: Okhlopkova Z.¹, Razgonova M.²^,3, Egorova P.⁴, Golokhvast K.⁵^,3^,6
Мекемелер:
1. North-Eastern Federal University
2. Far Eastern Federal University, Advanced Engineering School, Institute of Biotechnology, Bioengineering, and Food Systems
3. Federal Research Center Vavilov All-Russia Institute of Plant Genetic Resources (VIR)
4. Institute for Biological Problems of Permafrost, Siberian Branch, Russian Academy of Sciences
5. Far Eastern Federal University, REC Nanotechnology, Polytechnic Institute
6. Siberian Federal Scientific Center for Agrobiotechnologies, Russian Academy of Sciences
Шығарылым: Том 70, № 3 (2023)
Беттер: 327-336
Бөлім: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://journals.rcsi.science/0015-3303/article/view/130220
DOI: https://doi.org/10.31857/S0015330322600723
EDN: https://elibrary.ru/IBPENP
ID: 130220

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат
Рұқсат жабық

Рұқсат берілді
Рұқсат жабық

Тек жазылушылар үшін

Аннотация
Авторлар туралы
Әдебиет тізімі
Қосымша файлдар
Статистика

Аннотация

Dracocephalum jacutense Peschkova is a rare and endangered species of the genus Dracocephalum L. of Lamiaceae family. The species was first described in 1997 and listed in the Red Data Book of Yakutia (2017). Until now, due to the rare occurrence of D. jacutense, almost none of its phytochemical studies have been carried out and there is no information on the content of biologically active compounds (secondary metabolites) of the plant. In this work, using the method of tandem mass spectrometry, a complex of polyphenolic compounds was studied in the inflorescences of the Dracocephalum jacutense, collected in the areas of its first discovery - the Kobyaysky district of the Republic of Sakha (Yakutia). As a result of the analysis, 48 polyphenolic compounds were found in the alcohol extracts of Dracocephalum jacutense inflorescences, among which 17 flavones, 7 flavonols, 3 flavan-3-ols, 12 phenolic acids, 1 lignan, 2 coumarins, 6 anthocyanidins were identified. It should be noted that more than half (30 compounds) of all the identified polyphenols for representatives of the genus Dracocephalum L. were discovered for the first time. The results obtained state the unique composition of polyphenolic compounds in the inflorescences of D. jacutense Peschkova. In order to preserve this sparse local endemic of Eastern Siberia, work has begun on the development of an effective method for its micropropagation in vitro.

Негізгі сөздер

Dracocephalum jacutense, HPLC-MS/MS, tandem mass spectrometry, polyphenolic compounds, CID spectrum

Әдебиет тізімі

Пешкова Г.А. Dracocephalum L. // Флора Сибири. Т. 11. Новосибирск: Наука, 1997. С. 170.
Денисова Г.Р., Николин Е.Г. Онтогенез и возрастной анализ ценопопуляций узколокального эндемика Якутии Dracocephalum jacutense (Lamiaceae) // Ботанический журнал. 2012. Т. 97. № 3. С. 365.
Красная книга Республики Саха (Якутия). Т. 1: Редкие и находящиеся под угрозой исчезновения виды растений и грибов / Отв. ред. Н.С. Данилова. Москва: Изд-во “Реарт”. 2017. 412 с.
Olennikov D.N., Chirikova N.K., Okhlopkova Z.M., Zulfugarov I.S. Chemical composition and antioxidant activity of tánara ótó (Dracocephalum palmatum Stephan), a medicinal plant used by the North-Yakutian nomads // Molecules. 2013. V. 18. P. 14105. https://doi.org/10.3390/molecules181114105
Olennikov D.N., Chirikova N.K., Kim E., Kim S.W., Zulfugarov I.S. New glycosides of eriodictyol from Dracocephalum palmatum // Chem. Nat. Compd. 2018. V. 54. P. 860. https://doi.org/10.1007/s10600-018-2499-4
Razgonova M.P., Okhlopkova Z.M., Golokhvast K.S. Research of Dracocephalum palmatum S. and Dracocephalum ruyschiana L. originating from Yakutia and identification of metabolites by tandem mass spectrometry // BIO Web of Conferences. 2022. V. 43. P. 01010. https://doi.org/10.1051/bioconf/20224301010
Okhlopkova Zh.M., Razgonova M.P., Pikula K.S., Zakharenko A.M., Piekoszewski W., Manakov Y.A., Ercisli S., Golokhvast K.S. Dracocephalum palmatum S. and Dracocephalum ruyschiana L. originating from Yakutia: a high-resolution mass spectrometric approach for the comprehensive characterization of phenolic compounds // Applied Sci. 2022. V. 12. P. 1766. https://doi.org/10.3390/app12031766
Lee S.-E., Okhlopkova Z., Lim C., Cho S. Dracocephalum palmatum Stephan extract induces apoptosis in human prostate cancer cells via the caspase-8-mediated extrinsic pathway // Chinese J. Nat. Med. 2020. V. 18. P. 793. https://doi.org/10.1016/S1875-5364(20)60019-X
Cai Z., Wang C., Zou L., Liu X., Chen J., Tan M., Mei Y., Wei L. Comparison of multiple bioactive constituents in the flower and the caulis of Lonicera japonica based on UFLC-QTRAP-MS/MS combined with multivariate statistical analysis // Molecules. 2019. V. 24. P. 1936. https://doi.org/10.3390/molecules24101936
Aita S.E., Capriotti A.L., Cavaliere C., Cerrato A., Giannelli Moneta B., Montone C.M., Piovesana S., Lagana A. Andean blueberry of the genus disterigma: a high-resolution mass spectrometric approach for the comprehensive characterization of phenolic compounds // Separations. 2021. V. 8. P. 58. https://doi.org/10.3390/separations8050058
Abu-Reidah I.M., Ali-Shtayeh M.S., Jamous R.M., Arraes-Roman D., Segura-Carretero A. HPLC–DAD–ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits // Food Chem. 2015. V. 166. P. 179. https://doi.org/10.1016/j.foodchem.2014.06.011
Mena P., Cirlini M., Tassotti M., Herrlinger K.A., Dall’Asta C., Del Rio D. Phytochemical profiling of flavonoids, phenolic acids, terpenoids, and volatile fraction of a rosemary (Rosmarinus officinalis L.) extract // Molecules. 2016. V. 21. P. 1576. https://doi.org/10.3390/molecules21111576
Xu L.L., Xu J.J., Zhong K.R., Shang Z.P., Wang F., Wang R.F., Liu B. Analysis of non-volatile chemical constituents of Menthae Haplocalycis herba by ultra-high performance liquid chromatography – high resolution mass spectrometry // Molecules. 2017. V. 22. P. 1756. https://doi.org/10.3390/molecules22101756
Belmehdi O., Bouyahya A., Jeko J., Cziaky Z., Zengin G., Sotkó G., El Baaboua A., Senhaji N.S., Abrini J. Synergistic interaction between propolis extract, essential oils, and antibiotics against Staphylococcus epidermidis and methicillin resistant Staphylococcus aureus // Int. J. Second Metab. 2021. V. 8. P. 195. https://doi.org/10.21448/ijsm.947033
Zhang J., Xu X.-J., Xu W., Huang J., Zhu D., Qui X.-H. Rapid characterization and identification of flavonoids in Radix Astragali by ultra-high-pressure liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry // J. Chromatogr. Sci. 2015. V. 53. P. 945. https://doi.org/10.1093/chromsci/bmu155
Fanthoni A., Saepudin E., Cahyana A.H., Rahayu D.U.C., Haib J. Identification of nonvolatile compounds in clove (Syzygium aromaticum) from manado // International symposium on Current Progress in Mathematics and Sciences. 2017. V. 1862. P. 030079-1. https://doi.org/10.1063/1.4991183
Razgonova M.P., Bazhenova B.B., Zabalueva Y.Y., Burkhanova A.G., Zakharenko A.M., Kupriyanov A.N., Sabitov A.S., Ercisli S., Golokhvast K.S. Rosa davurica Pall., Rosa rugosa Thumb., and Rosa acicularis Lindl. originating from far eastern Russia: Screening of 146 chemical constituents in tree species of the genus rosa // Applied Sci. 2022. V. 12. P. 9401. https://doi.org/10.3390/app12199401
Pandey R., Kumar B. HPLC–QTOF–MS/MS-based rapid screening of phenolics and triterpenic acids in leaf extracts of Ocimum species and their interspecies variation // J. Liq. Chromatogr. & Related Tech. 2016. V. 39. P. 225. https://doi.org/10.1080/10826076.2016.1148048
Hamed A.R., El-Hawary S.S., Ibrahim R.M., Abdelmohsen U.R., El-Halawany A.M. Identification of chemopreventive components from halophytes belonging to Aizoaceae and Cactaceae through LC/MS – bioassay guided approach // J. Chrom. Sci. 2021. V. 59. P. 618. https://doi.org/10.1093/chromsci/bmaa112
He Y.-K., Yao Y.-Y., Chang Y.-N. Characterization of anthocyanins in Perilla frutescens var. acuta extract by advanced UPLC-ESI-IT-TOF-MSn method and their anticancer bioactivity // Molecules. 2015. V. 20. P. 9155. https://doi.org/10.3390/molecules20059155
Pan M., Lei Q., Zang N., Zhang H.A. Strategy based on GC-MS/MS, UPLC-MS/MS and virtual molecular docking for analysis and prediction of bioactive compounds in eucalyptus globulus leaves // Int. J. Molec. Sci. 2019. V. 20. P. 3875. https://doi.org/10.3390/ijms20163875
El-Sayed M.A., Abbas F.A., Refaat S., El-Shafae A.M., Fikry E. UPLC-ESI-MS/MS profile of the ethyl acetate fraction of aerial parts of bougainvillea 'Scarlett O’Hara’ cultivated in Egypt // Egyptian J. Chem. 2021. V. 64. P. 22. https://doi.org/10.21608/ejchem.2020.45694.2933
Spinola V., Pinto J., Castilho P.C. Identification and quantification of phenolic compounds of selected fruits from Madeira Island by HPLC-DAD-ESI-MSn and screening for their antioxidant activity // Food Chem. 2015. V. 173. P. 14. https://doi.org/10.1016/j.foodchem.2014.09.163
Razgonova M.P., Tekutyeva L.A., Podvolotskaya A.B., Stepochkina V.D., Zakharenko A.M., Golokhvast K.S. Zostera marina L. supercritical CO2-extraction and mass spectrometric characterization of chemical constituents recovered from seagrass // Separations. 2022. V. 9. P. 182. https://doi.org/10.3390/separations9070182
Cavaliere C., Foglia P., Pastorini E., Samperi R., Laganà A. Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high performance liquid chromatography with tandem mass spectrometry. Rapid Commun. Mass. Spectrom. 2005. V. 19. P. 3143. https://doi.org/10.1002/rcm.2185
Chandrasekara A., Shahidi F. Determination of antioxidant activity in free and hydrolyzed fractions of millet grains and characterization of their phenolic profiles by HPLC-DAD-ESI-MSn // J. Functional Foods. 2011. V. 3. P. 144. https://doi.org/10.1016/j.jff.2011.03.007
Yin N.-W., Wang S.-X., Jia L.-D., Zhu M.-C., Yang J., Zhou B.-J., Yin J.-M., Lu K., Wang R., Li J.-N., Qu C.-M. Identification and characterization of major constituents in different-colored rapeseed petals by UPLC−HESI--MS/MS // Agricult. Food Chem. 2019. V. 67. P. 11053. https://doi.org/10.1021/acs.jafc.9b05046
Sobeh M., Mahmoud M.F., Abdelfattah M.A.O., Cheng H., El-Shazly A.M., Wink M. A proanthocyanidin-rich extract from Cassia abbreviata exhibits antioxidant and hepatoprotective activities in vivo // J. Ethnopharmacol. 2018. V. 213. P. 38. https://doi.org/10.1016/j.jep.2017.11.007
Qin D., Wang Q., Li H., Jiang X., Fang K., Wang Q., Li B., Pan C., Wu H. Identification of key metabolites based on non-targeted metabolomics and chemometrics analyses provides insights into bitterness in Kucha [Camellia kucha (Chang et Wang) Chang] // Food Res. Int. 2020. V. 138. P. 109789. https://doi.org/10.1016/j.foodres.2020.109789
Qin D., Wang Q., Li H., Jiang X., Fang K., Wang Q., Li B., Pan C., Wu H. Chemical constituents of radix Actinidia chinensis planch by UPLC–QTOF–MS // Biomedical Chromatography. Wiley. 2021. e5103. https://doi.org/10.1002/bmc.5103
Yin Y., Zhang K., Wei L., Chen D., Chen Q., Jiao M., Li X., Huang J., Gong Z., Kang N., Li F. The molecular mechanism of antioxidation of huolisu oral liquid based on serum analysis and network analysis // Frontiers in Pharma. 2021. V. 12. P. 710976. https://doi.org/10.3389/fphar.2021.710976
Serrano C.A., Villena G.K., Rodriguez E.F. Phytochemical profile and rosmarinic acid purification from two Peruvian Lepechinia Willd. species (Salviinae, Mentheae, Lamiaceae) // Sci. Reports. 2021. V. 11. P. 7260. https://doi.org/10.1038/s41598-021-86692-3
Eklund P.C., Backman M. J., Kronberg L.A., Smeds A.I., Sjoholm R.E. Identification of lignans by liquid chromatography-electrospray ionization ion-trap mass spectrometry // J. Mass Spectr. 2008. V. 43. P. 97. https://doi.org/10.1002/jms.1276.
Ruiz A., Hermosín-Gutiérrez I., Vergara C., von Baer D., Zapata M., Hitschfeld A., Obando L., Mardones C. Anthocyanin profiles in south Patagonian wild berries by HPLC-DAD-ESI-MS/MS // Food Res. Int. 2013. V. 51. P. 706. https://doi.org/10.1016/j.foodres.2013.01.043