Phenological Fluctuations of Secondary Metabolites in Dracocephalum charkeviczii

V. P. Grigorchuk; Григорчук В. П.; O. V. Nakonechnaya; Наконечная О. В.; O. V. Grishchenko; Грищенко О. В.; A. B. Bezdelev; Безделев А. Б.

doi:10.31857/S0015330323600870

Phenological Fluctuations of Secondary Metabolites in Dracocephalum charkeviczii

Авторлар: Grigorchuk V.P.¹, Nakonechnaya O.V.¹, Grishchenko O.V.¹, Bezdelev A.B.²
Мекемелер:
1. Federal Scientific Center of the East Asia Terrestrial Biodiversity, Far Eastern Branch, Russian Academy of Sciences
2. Zhirmunsky National Scientific Center of Marine Biology, Primorsky Aquarium Scientific and Educational Centre, Far Eastern Branch, Russian Academy of Sciences
Шығарылым: Том 70, № 7 (2023)
Беттер: 736-742
Бөлім: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://journals.rcsi.science/0015-3303/article/view/233771
DOI: https://doi.org/10.31857/S0015330323600870
EDN: https://elibrary.ru/BFNHUD
ID: 233771

Дәйексөз келтіру

Толық мәтін

Ашық рұқсат
Рұқсат жабық

Рұқсат берілді
Рұқсат жабық

Тек жазылушылар үшін

Аннотация
Авторлар туралы
Әдебиет тізімі
Қосымша файлдар
Статистика

Аннотация

Plants from the genus Dracocephalum are a source of biologically active compounds, including rosmarinic acid and different flavonoids. Their concentration varies during the vegetation period. In order to examine changes in their content in Dracocephalum charkeviczii Prob., an endemic species of Sikhote Alin and South Kuriles, wild and cultivated plants were collected in three phenological stages: vegetation, flowering/start of fructification, and preparation for withering. By means of HPLC with UV and mass selective detection, 15 polyphenol compounds were detected in methanol extracts from the leaves. Several new compounds—coumaric acid glycoside, quercetin glycoside and rutinoside, and acacetin coumaroylglycoside—were identified in D. charkeviczii. Synthesis of most flavonoids was found to be the highest in the beginning of the vegetation period, and gradually decreased by its end. The concentration of caffeic acid derivatives (chlorogenic acid, rosmarinic acid glycoside, and dehydrorhabdosiin) increased, but the total concentration of compounds decreased by the end of vegetation.

Негізгі сөздер

Dracocephalum charkeviczii, secondary metabolites, polyphenols, phenology

Әдебиет тізімі

Horn T., Völker J., Rühle M., Häser A., Jürges G., Nick P. Genetic authentication by RFLP versus ARMS? The case of Moldavian dragonhead (Dracocephalum moldavica L.) // Eur. Food Res. Technol. 2014. V. 238. P. 93.
Kakasy A., Füzfai Z., Kursinszki L., Molnár-Perl I., Lemerkovics É. Analysis of nonvolatile constituens in Dracocephalum species by HPLC and GC-MS // Chromatographia. 2006. V. 63. P. S17. https://doi.org/10.1365/s10337-006-0741-x
Bulgakov V.P., Inyushkina Y.V., Fedoreyev S. Rosmarinic acid and its derivatives: biotechnology and applications // Crit. Rev. Biotechnol. 2012. V. 32. P. 203. https://doi.org/10.3109/07388551.2011.59680 4
Petersen M., Simmonds M.S.J. Rosmarinic acid // Phytochemistry. 2003. V. 62. P. 121. https://doi.org/10.1016/S0031-9422(02)00513-7
Zeng Q., Jin H.Z., Quin J.J., Fu J.J., Hu X.J., Liu J.H., Yan L., Chen M., Zhang W.D. Chemical constituents of plants from the genus Dracocephalum // Chem Biodivers. 2010. V. 7. P. 1911. https://doi.org/ 0188https://doi.org/10.1002/cbdv.20090
Weremczuk-Jeżyna I., Kuźma Ł., Kiss A.K., Grzegorczyk-Karolak I. Effect of cytokinins on shoots proliferation and rosmarinic and salvianolic acid B production in shoot culture of Dracocephalum forrestii W.W. Smith // Acta Physiol. Plant. 2018. V. 40. P. 1. https://doi.org/10.1007/s11738-018-2763-z
Li G.S., Jiang W.I., Tian J.W., Qu G.W., Zhu H.B., Fu F.H. In vitro band in vivo antifibrotic effects of rosmarinic acid on experimental liver fibrosis // Phytomedicine. 2010. V. 17. P. 282.https://doi.org/10.1016/j.phymed.2009.05.002
Inyunshina Y.V., Bulgakov V.P., Veselova M.V., Bryukhanov V.M., Zverev Y.F., Lampatov V.V., Azarova O.V., Tchemoded G.K., Fedoreyev S.A., Zhuravlev Y.N. High rabdosin and rosmarinic acid production in Eritrichium sericeum callus cultures and the effect of the calli on Masugi-nephritis in rats // Biosci. Biotechnol. Biochem. 2007. V. 71. P. 1286. https://doi.org/10.1271/bbb60684
Jaiong R.W., Lou K.M., Hon P.M., Mak T.C., Woo K.S., Fung K.P. Chemistry and biological activities of caffeic acid derivatives from Salvia miltiorrhiza // Curr. Med. Chem. 2005. V. 12. P. 237.https://doi.org/10.2174/0929867053363397
Hosni K., Msaada K., Ben Taârit M., Marzouk B. Phenological variations of secondary metabolites from Hypericum triquetrifolium Turra. // Biochem. Syst. Ecol. 2011. V. 39. P. 43. https://doi.org/10.1016/j.bse.2011.01.001
Jordán M.J., Martínez R.M., Goodner K.L., Baldwin E.A., Sotomayor J.A. Seasonal variation of Thymus hyemalis Lange and Spanish Thymus vulgaris L. essential oils composition // Ind. Crop Prod. 2006. V. 24. P. 253–263. https://doi.org/10.1016/j.indcrop.2006.06.011
Ebrahimi N.S., Hadian J., Mirjalili M.H., Sonboli A., Yousefzadi M. Essential oil composition and antibacterial activity of Thymus caramanicus at different phenological stages // Food Chem. 2008. V. 110. P. 927. https://doi.org/10.1016/j.foodchem.2008.02.083
Abbasi N., Fattahi M., Ghosta Y., Sefidkon F. Volatile compounds and antifungal activity of Dracocephalum moldavica L. at different phenological stages // J. Essent. Oil Res. 2022. V. 34. P. 87. https://doi.org/10.1080/10412905.2021.1975577
Kotyuk L.A., Ivashchenko I.V., Korablova O.A., Rakhmetov D.B. Impact of climate variability on the duration of phenological quality of Dracocephalum moldavica L. in agroclimatic zones of Polissya and Forest-Steppe in Ukraine // Ukr. J. Ecol. 2021. V. 11. P. 39. https://doi.org/10.15421/2021_240
Fattahi M., Bonfill M., Fattahi B., Torras-Claveria L., Sefidkon F., Cusido R.M., Palazon J. Secondary metabolites profiling of Dracocephalum kotschyi Boiss at three phenological stages using uni-and multivariate methods // J. Appl. Res. Med. Aromat. Plants. 2016. V. 3. P. 177. https://doi.org/10.1016/j.jarmap.2016.04.002
Mohtashami S., Babalar M., Mirjalili M.H. Phenological variation in medicinal traits of Dracocephalum moldavica L. (Lamiaceae) under different growing conditions // J. Herbs Spices Med. Plants. 2013. V. 19. P. 377. https://doi.org/10.1080/10496475.2013.811146
Nakonechnaya O.V., Gafitskaya I.V., Grigorchuk V.P., Gorpenchenko T.Y., Bezdelev A.B., Zhuravlev Y.N. Polyphenol composition of Dracocephalum charkeviczii Prob. plants in in situ and in vitro conditions // Russ. J. Plant. Physiol. 2022. V. 69. P. 27. https://doi.org/10.1134/S1021443722010149
Безделев А.Б., Безделева Т.А. Жизненные формы семенных растений российского Дальнего Востока. Владивосток: Дальнаука, 2006. 296 с.
Kozhevnikov A.E., Kozhevnikova Z.V., Kwak M., Lee B.Y. Illustrated flora of the Primorsky Territory [Russian Far East]. National Institute of Biological Resources, Incheon, 2019. 1126 c.
Пробатова Н.С., Баркалов В.Ю., Нечаев В.А. Хромосомные числа сосудистых растений в Приморском крае: дальнейшее изучение // Ученые записки ЗабГУ. Серия: Естественные науки. 2016. Т. 11. № 1. С. 27.
Weremczuk-Jeżyna I., Skała E., Kuźma Ł., Kiss A.K., Grzegorczyk-Karolak I. The effect of purine-type cytokinin on the proliferation and production of phenolic compounds in transformed shoots of Dracocephalum forrestii // J. Biotechnol. 2019. V. 306. P. 125. https://doi.org/10.1016/j.jbiotec.2019.09.014
Vassallo A., Cioffi G., De Simone F., Braca A., Sanogo R., Vanella A., Russo A., De Tommasi N. New flavonoid glycosides from Chrozophora senegalensis and their antioxidant activity // Nat. Prod. Commun. 2006. V. 1. P. 1089. https://doi.org/10.1177/1934578X0600101204
Holser R.A. Lipid encapsulated phenolic compounds by fluidization // J. Encapsulation Adsorpt. Sci. 2013. V. 3. P. 13. https://doi.org/10.4236/jeas.2013.31002
Bystrom L.M., Lewis B.A., Brown D.L., Rodriguez E., Obendorf R.L. Characterisation of phenolics by LC–UV/Vis, LC–MS/MS and sugars by GC in Melicoccus bijugatus Jacq. “Montgomery” fruits // Food Chem. 2008. V. 111. P. 1017. https://doi.org/10.1016/j.foodchem.2008.04.058
Allen F., Greiner R., Wishart D. Competitive fragmentation modeling of ESI-MS/MS spectra for putative metabolite identification // Metabolomics. 2015. V. 11. P. 98. https://doi.org/10.1007/s11306-014-0676-4
Yosr Z., Hnia Ch., Rim T., Mohamed B. Changes in essential oil composition and phenolic fraction in Rosmarinus officinalis L. var. typicus Batt. organs during growth and incidence on the antioxidant activity // Ind. Crops Prod. 2013. V. 43. P. 412. https://doi.org/10.1016/j.indcrop.2012.07.044
Aziz E.E., Ezz El-Din A.A., Omer E.A. Quantitative and qualitative changes in essential oil of Dracocephalum moldavica at different growth stages // Int. J. Acad. Res. 2010. V. 2. P. 198.
Del Bano M.J., Lorente J., Castillo J., Benavente-García O., Del Rio J.A., Ortuño A., Quirin K.-W., Gerard D. Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis antioxidant activity // J. Agric. Food Chem. 2003. V. 51. P. 4247. https://doi.org/10.1021/jf0300745
Winkel-Shirley B. Biosynthesis of flavonoids and effects of stress // Curr. Opin. Plant Biol. 2002. V. 5. P. 218. https://doi.org/10.1016/S1369-5266(02)00256-X
Fattahi M., Nazeri V., Torras-Claveria L., Sefidkon F., Cusido R.M., Zamani Z., Palazon J. Identification and quantification of leaf surface flavonoids in wild-growing populations of Dracocephalum kotschyi by LC–DAD–ESI–MS // Food Chem. 2013. V. 141. P. 139. https://doi.org/10.1016/j.foodchem.2013.03.019