![]() | |||
Research paper Botanica Pacifica. A journal of plant science and conservation 2024. Preprint Article first published online: 04 AUG 2024 | DOI: 10.17581/bp.2024.13209 Ribes fragrans Pall.: Supercritical CO2-extraction and complete plant metabolome Mayya P. Razgonova 1,2 ![]() ![]() ![]() ![]() ![]() ![]() 1 N.I. Vavilov All-Russian Institute of Plant Genetic Resources, Saint-Petersburg, Russia 2 Advanced Engineering School "Institute of Biotechnology, Bioengineering and Food Systems", Far Eastern Federal University, Vladivostok, Russia 3 FSBSI Magadan Research Institute of Agriculture, Magadan, Russia 4 Siberian Federal Scientific Centre of Agrobiotechnology, Krasnoobsk, Russia Supercritical fluid technology was used to obtain bioactive substances from leaves of Ribes fragrans Pallas. Supercritical fluid technology showed the strongest extractive effect, which helped to extract the maximum amount of bioactive substances. Several experimental conditions were investigated in the pressure range 50–300 bar, with the used volume of co-solvent ethanol in the amount of 2.5 % in the liquid phase at a temperature in the range of 31–70°C. The most effective extraction conditions were: pressure 200 Bar and temperature 55°C. The CO2-extract of leaves of R. fragrans contain various polyphenolic compounds and compounds of other chemical groups with valuable biological activity. For the first time, the metabolome of supercritical extracts of R. fragrans leaves was studied in this research. Using the method of supercritical extraction of plant matrices with the method of tandem mass spectrometry, it was possible to tentatively identify 79 bioactive compounds, of which 53 compounds are of polyphenol group. 20 chemical compounds from polyphenol group and 12 chemical compounds from other chemical groups were identified for the first time in genus Ribes. Разгонова М.П., Сабитов А.С., Сенотрусова Т.А., Ли Н.Г., Витомскова Е.А., Голохваст К.С. Ribes fragrans Pall.: Сверхкритическая CO2-экстракция и полный метаболом растения. Для получения биоактивных веществ из листьев Ribes fragrans Pall. использовали сверхкритическую флюидную технологию. Сверхкритическая флюидная технология показала самый сильный экстрактивный эффект, который позволил извлечь максимальное количество биоактивных веществ. Было исследовано несколько экспериментальных условий в диапазоне давлений 50-300 бар, с используемым объемом сорастворителя этанола в количестве 2,5 % в жидкой фазе при температуре в диапазоне 31–70°C. Наиболее эффективными условиями экстракции оказались: давление 200 бар и температура 55°C. СО2-экстракт листьев R. fragrans содержит различные полифенольные соединения и соединения других химических групп, обладающие ценной биологической активностью. В данном исследовании впервые изучен метаболом сверхкритических экстрактов листьев R. fragrans. Используя метод сверхкритической экстракции растительных матриц с применением метода тандемной масс-спектрометрии, удалось предварительно идентифицировать 79 биологически активных соединений, из которых 53 соединения относятся к группе полифенолов. 20 химических соединений из группы полифенолов и 12 химических соединений из других химических групп были впервые идентифицированы в роде Ribes. Keywords: Ribes fragrans, supercritical fluid technology, tandem mass spectrometry, polyphenols, metabolome, технология сверхкритического флюида, тандемная масс-спектрометрия, полифенолы, метаболом References Aabideen, Z.U., M.W. Mumtaz, M.T. Akhtar, H. Mukhtar, S.A Raza, T. Touqeer & N. Saari 2020. Anti-obesity attributes; UHPLC-QTOF-MS/MS-based metabolite profiling and molecular docking insights of Taraxacum officinale. Molecules 25:4935. CrossRef Abu-Reidah, I.M., M.S. Ali-Shtayeh, R.M. Jamous, D. Arraes-Roman & A. Segura-Carretero 2015. HPLC-DAD-ESI-MS/MS screening of bioactive components from Rhus coriaria L. (Sumac) fruits. Food Chemistry 166:179-191. CrossRef Abeywickrama, G., S.C. Debnath, P. Ambigaipalan & F. Shahidi 2016. Phenolics of selected cranberry genotypes (Vaccinium macrocarpon Ait.) and their antioxidant efficacy. Journal of Agriculture Food Chemistry 64(49):9342-9351. CrossRef Aghakhani, F., N. Kharazin & Z.L. Gooini 2018. Flavonoid constituents of Phlomis (Lamiaceae) species using liquid chromatography mass spectrometry. Phytochemical Analysis 29(2):180-195. CrossRef Aita, S.E., A.L. Capriotti, C. Cavaliere, A. Cerrato, B. Giannelli Moneta, C.M. Montone, S. Piovesana & A. Lagana 2021. Andean Blueberry of the genus Disterigma: A highresolution mass spectrometric approach for the comprehensive characterization of phenolic compounds. Separations 8:58. CrossRef Beh, C.C., R. Mammucari & N.R. Foster 2012. Lipids-based drug carrier systems by dense gas technology: A review. Chemical Engineering Journal 188:1-14. CrossRef Belmehdi, O., A. Bouyahya, J. Jeko, Z. Cziaky, G. Zengin, G. Sotko, A. El Baaboua, N.S. Senhaji & J. Abrini 2021. Synergistic interaction between propolis extract, essential oils, and antibiotics against Staphylococcus epidermidis and methicillin resistant Staphylococcus aureus. International Journal of Secondary Metabolite 8(3):195-213. CrossRef Berger A. 1924. Taxonomic review of currants and gooseberries. In: New York State Agricultural Experiment Station. Technical bulletin, pp. 1-109, Geneva, N.Y., New York State Agricultural Experiment Station. Boczkarnikova, N.M. 1973. Black currant in the Far East. Dal'nevostochnoe knizhnoe izdatel'stvo, Vladivostok, 183 pp. (in Russian with English summary). [Бочкарникова Н.М. 1973. Черная смородина на Дальнем Востоке. Владивосток: Дальневосточное книжное издательство. 183 с.]. Bonzanini, F., R. Bruni, G. Palla, N. Serlataite & A. Caligiani 2009. Identification and distribution of lignans in Punica granatum L. fruit endocarp, pulp, seeds, wood knots and commercial juices by GC-MS. Food Chemistry 117:745-749. CrossRef Burgos-Edwards, A., F. Jimenez-Aspee, C. Theoduloz & G. Schmeda-Hirschmann 2018. Colonic fermentation of polyphenols from Chilean currants (Ribes spp.) and its effect on antioxidant capacity and metabolic syndromeassociated enzymes. Food Chemistry 30:144-155. CrossRef Cai, Z., C. Wang, L. Zou, X. Liu, J. Chen, M. Tan, Y. Mei & L. Wei 2019. Comparison of multiple bioactive constituents in the flower and the caulis of Lonicera japonica based on UFLC-QTRAP-MS/MS combined with multivariate tatistical analysis. Molecules 24:1936. CrossRef Cavaliere, C., P. Foglia, E. Pastorini, R. Samperi & A. Laganà 2005. Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high-performance liquid chromatography with tandem mass spectrometry. Rapid Communications in Mass Spectrometry 19(21):3143-3158. CrossRef Chen, Y., X. Cai, G. Li, X. He, X. Yu, Q. Xiao & Z. Xiang 2021. Chemical constituents of radix Actinidia chinensis planch by UPLC-QTOF-MS. Biomedical Chromatography 35(7):e5103. CrossRef Cirlini, M., P. Mena, M. Tassotti, K.A. Herrlinger, K.M. Nieman, C. Dall'Asta & D. Del Rio 2016. Phenolic and volatile composition of a dry spearmint (Mentha spicata L.) extract. Molecules 21(8):1007. CrossRef da Silva, L.P., E. Pereira, T.C.S.P. Pires, M.J. Alves, O.R. Pereira, L. Barros & I.C.F.R. Ferreira 2019. Rubus ulmifolius Schott fruits: A detailed study of its nutritional, chemical and bioactive properties. Food Research International 119:34-43. CrossRef Deuber, H., C. Guignard, L. Hoffmann & D. Evers 2012. Polyphenol and glycoalkaloid contents in potato cultivars grown in Luxembourg. Food Chemistry 135:2814-2824. CrossRef Dinelli, G., A. Segura-Carretero, R. Di Silvestro, I. Marotti, D. Arráez-Román, S. Benedettelli, L. Ghiselli & A. Fernandez-Gutierrez 2011. Profiles of phenolic compounds in modern and old common wheat varieties determined by liquid chromatography coupled with time-of-flight mass spectrometry. Journal of Chromatography A 1218(42):7670-7681. CrossRef Dudov, S.V. & A.P. Seregin (eds) 2024. Atlas of the flora of Russia: Electronic resource. Available at: https://plant.depo.msu.ru/ (in Russian). [Дудов С.В., Серегин А.П. (ред.). Атлас флоры России: Электронный ресурс. - М.: МГУ, 2024. Режим доступа: https://plant.depo.msu.ru/ (дата обращения 04.08.2024)]. D'Urso, G., G. Sarais, C. Lai, C. Pizza & P. Montoro 2017. LCMS based metabolomics study of different parts of myrtle berry from Sardinia (Italy). Journal of Berry Research 7:217-229. CrossRef Ekeberg, D., P.-O. Flate, M. Eikenes, M. Fongen & C.F. Naess-Andresen 2006. Qualitative and quantitative determination of extractives in heartwood of Scots pine (Pinus sylvestris L.) by gas chromatography. Journal of Chromatography A 1109:267-272. CrossRef Eklund, P.C., M.J. Backman, L.A. Kronberg, A.I. Smeds & R.E. Sjoholm 2008. Identification of lignans by liquid chromatography-electrospray ionization ion-trap mass spectrometry. Journal of Mass Spectrometry 43:97-107. CrossRef El-Sayed, M.A., F.A. Abbas, S. Refaat, A.M. El-Shafae & E. Fikry 2021. UPLC-ESI-MS/MS profile of the ethyl acetate fraction of aerial parts of Bougainvillea 'Scarlett O'Hara' cultivated in Egypt. Egyptian Journal of Chemistry 64:22. CrossRef Fanthoni, A., E. Saepudin, A.H. Cahyana, D.U.C. Rahayu & J. Haib 2016. Identification of nonvolatile compounds in clove (Syzygium aromaticum) from Manado. International Symposium on Current Progress in Mathematics and Sciences 2016 (ISCPMS 2016) 1862:030079-1-030079-10. Foster, N., R. Mammucari, F. Dehghani, A. Barrett, K. Bezanehtak, E. Coen, G. Combes, L. Meure, A. Ng, H.L. Regtop & A. Tandya 2003. Processing pharmaceutical compounds using dense gas technology. Industrial & Engineering Chemistry Research 42:6476-6493. CrossRef Garg, M., M. Chawla, V. Chunduri, R. Kumar, S. Sharma, N.K. Sharma, N. Kaur, A. Kumar, J.K. Mundey & M.K. Saini 2016. Transfer of grain colors to elite wheat cultivars and their characterization. Journal of Cereal Science 71:138-144. CrossRef Geng, P., J. Sun, M. Zhang, X. Li, J.M Harnly & P. Chen 2016. Comprehensive characterization of C-glycosyl flavones in wheat (Triticum aestivum L.) germ using UPLCPDA-ESI/HRMSn and mass defect filtering. Journal of Mass Spectrometry 51(10):914-930. CrossRef Gordon, A., B. Schadow, K.E Quijano & F. Marx 2011. Chemical characterization and antioxidant capacity of berries from Clidemia rubra (Aubl.) Mart. (Melastomataceae). Food Research International 44:2120-2127. CrossRef Gulsoy-Tolpan, G., F. Goger, A. Yildiz-Pekoz, S. Gibbons, G. Sariyar & A. Mat 2018. Chemical constituents of the different parts of Colchicum micranthum and C. chalcedonicum and their cytotoxic activities. Natural Product Communications 3(5):535-538. CrossRef Guo, K., C. Tong, Q. Fu, J. Xu, S. Shi & Y. Xiao 2019. Identification of minor lignans, alkaloids, and phenylpropanoid glycosides in Magnolia officinalis by HPLC-DADQTOF-MS/MS. Journal of Pharmaceutal And Biomedical Analysis 170:153-160. CrossRef Hamed, A.R., S.S. El-Hawary, R.M. Ibrahim, U.R. Abdelmohsen & A.M. El-Halawany 2021. Identification of chemopreventive components from halophytes belonging to Aizoaceae and Cactaceae through LC/MS-bioassay guided approach. Journal of Chromatography Science 59(7):618-626. CrossRef Hanganu, D., L. Vlase & N. Olah 2010. LS/MS analysis of isoflavones from Fabaceae species extracts. Farmacia 58(2):177-183. Hassan, W., S. Abdelaziz & H. Yousef 2019. Chemical composition and biological activities of the aqueous fraction of Parkinsonea aculeata L. growing in Saudi Arabia. Arabian Journal of Chemistry 12(3):377-387. CrossRef Hossain, M.B., N.P. Brunton & D.K. Rai 2016. Effect of drying methods on the steroidal alkaloid content of potato peels, shoots and berries. Molecules 21:403. CrossRef Huang, Y., P. Yao, K.W. Leung, H. Wang, X.P. Kong, L. Wang, T.T.X. Dong, Y. Chen & K.W.K. Tsim 2018. The Yin-Yang property of Chinese medicinal herbs relates to chemical composition but not anti-oxidative activity: An illustration using spleen-meridian herbs. Frontiers in Pharmacology 9:1304. CrossRef Huang, X., Y. Liu, F. Song, Z. Liu & S. Liu 2009. Studies on principal components and antioxidant activity of different Radix Astragali samples using high-performance liquid chromatography/electrospray ionization multiple-stage tandem mass spectrometry. Talanta 78:1090-1101. CrossRef Ieri, F., M. Innocenti, L. Possieri & S. Gallori 2015. Phenolic composition of "bud extracts" of Ribes nigrum L., Rosa canina L. and Tilia tomentosa M. Journal of Pharmaceutical and Biomedical Analysis 115:1-9. CrossRef Jaiswal, R., L. Jayasinghe & N. Kuhnert 2012. Identification and characterization of proanthocyanidins of 16 members of the Rhododendron genus (Ericaceae) by tandem LC-MS. Journal of Mass Spectrometry 47:502-515. CrossRef Jaiswal, R., H. Muller, A. Muller, M.G.E. Karar & N. Kuhnert 2014. Identification and characterization of chlorogenic acids, chlorogenic acid glycosides and flavonoids from Lonicera henryi L. (Caprifoliaceae) leaves by LC-MSn. Phytochemistry 108:252-263. CrossRef Jeong, H.J., Y.B. Ryu & S.J. Park 2009. Neuraminidase inhibitory activities of flavonols isolated from Rhodiola rosea roots and their in vitro anti-influenza viral activities. Bioorganic & Medicinal Chemistry 17(19):6816-6823. CrossRef Kan, S., G. Chen, C. Han, Z. Chen, X. Song, M. Ren & H. Jiang 2011. Chemical constituents from the roots of Xanthium sibiricum L. Natural Product Research 25(13):1243-1249. CrossRef Karajanagi, S.S., R. Yoganathan, R. Mammucari, H. Park, J. Cox, S.M. Zeitels, R. Langer & N.R. Foster 2011. Application of a dense gas technique for sterilizing soft biomaterials. Biotechnology and Bioengineering 108:1716-1725. CrossRef Kharkevich, S.S. 1988. Grossulariaceae DC. In: Vascular plants of the soviet Far East, vol. 3 (S.S. Kharkevich, ed.), pp. 115-131, Nauka, Leningrad (in Russian with English summary). [Харкевич С.С. 1988. Крыжовниковые - Grossulariaceae DC. // Сосудистые растения советского Дальнего Востока / отв. ред. С.С. Харкевич. Ленинград: Наука. Т. 3. С. 115-131]. Kim, S., S. Oh, H.B. Noh, S. Ji, S.H. Lee, J.M. Koo, C.W. Choi & H.P. Jhun 2018. In vitro antioxidant and anti-Propionibacterium acnes activities of cold water, hot water, and methanol extracts, and their respective ethyl acetate fractions, from Sanguisorba officinalis L. Roots. Molecules 23:3001. CrossRef Li, W.-H., S.-T. Chang, S.-C. Chang & H.-T. Chang 2008. Isolation of antibacterial diterpenoids from Cryptomeria japonica bark. Natural Product Research 22(12):1085-1093. CrossRef Li X. & T. Tian 2018. Phytochemical characterization of Mentha spicata L. under differential dried-conditions and associated nephrotoxicity screening of main compound with organ-on-a-chip. Frontiers in Pharmacology 9:1067. CrossRef Llorent-Martinez, E.J., V. Spinola, S. Gouveia & P.C. Castilho 2015. HPLC-ESI-MSn characterization of phenolic compounds, terpenoid saponins, and other minor compounds in Bituminaria bituminosa. Industry Crops and Products 69:80-90. CrossRef Liu, P., A. Lindstedt, N. Markkinen, J. Sinkkonen, J. Suomela & B. Yang 2014. Characterization of metabolite profiles of leaves of bilberry (Vaccinium myrtillus L.) and lingonberry (Vaccinium vitis-idaea L.). Journal of Agricultural and Food Chemistry 62:12015-12026. CrossRef Maatta, K.R., A. Kamal-Eldin & A.R. Torronen 2003. High-performance liquid chromatography (HPLC) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (MS) detection: Ribes species. Journal of Agricultural and Food Chemistry 51:6736-6744. CrossRef Malyschev, L.I. 1994. The family Grossulariaceae. In: Flora of Siberia, vol. 7 (L.I. Malyshev & G.A. Peshkova, eds), pp. 208-217, Nauka, Novosibirsk (in Russian). [Малышев Л.И. 1994. Семейство Grossulariaceae - Крыжовниковые // Флора Сибири / ред. Л.И. Малышев и Г.А. Пешкова. Новосибирск: Наука. Т. 7. С. 208-217]. Martinez-Vazquez, M., R. Estrada-Reyes, A. Martinez-Laurrabaquio, C. Lopez-Rubalcava & G. Heinze 2012. Neuropharmacological study of Dracocephalum moldavica L. (Lamiaceae) in mice: Sedative effect and chemical analysis of an aqueous extract. Journal of Ethnopharmacology 141:908-917. CrossRef Mateos-Martin, M.L., E. Fuguet, A. Jimenez-Ardon, L. Herrero-Uribe, G. Tamayo-Castillo & J. Lluis Torres 2021. Identification of polyphenols from antiviral Chamaecrista nictitans extract using high-resolution LC-ESI-MS/MS. Analytic Bioanalytic Chemistry 406:5501-5506. CrossRef Matos, R.L., S.A.B. Vieira de Melo, E.C.M. Cabral Albuqueque & N.R. Foster 2019. Dense CO2 technology: Overview of recent applications for drug processing/formulation/delivery. Chemical Engineering and Processing - Process Intensification 140:64-77. CrossRef Mekam, P.N., S. Martini, J. Nguefack, D. Tagliazucchi & E. Stefani 2019. Phenolic compounds profile of water and ethanol extracts of Euphorbia hirta L. leaves showing antioxidant and antifungal properties. South African Journal of Botany 127:319-332. CrossRef Mena, P., L. Calani, C. Dall'Asta, G. Galaverna, C. Garcia-Viguera, R. Bruni, A. Crozier & D. Del Rio 2012. Rapid and comprehensive evaluation of (poly)phenolic compounds in pomegranate (Punica granatum L.) juice by UHPLC-MSn. Molecules 17:14821-14840. CrossRef Mena, P., M. Cirlini, M. Tassotti, K.A. Herrlinger, C. Dall'Asta & D. Del Rio 2016. Phytochemical profiling of flavonoids, phenolic acids, terpenoids, and volatile fraction of a rosemary (Rosmarinus officinalis L.) extract. Molecules 21:1576. CrossRef Navarro, M., E. Arnaez, I. Moreira, S. Quesada, G. Azofeifa, K. Wilhelm, F. Vargas & P. Chen 2019. Polyphenolic characterization, antioxidant, and cytotoxic activities of Mangifera indica cultivars from Costa Rica. Foods 8:384. CrossRef Pascale, R., M.A. Acquavia, T.R.I. Cataldi, A. Onzo, D. Coviello, S.A. Bufo, L. Scrano, R. Ciriello, A. Guerrieri & G. Bianco 2020. Profiling of quercetin glycosides and acyl glycosides in sun-dried peperoni di Senise peppers (Capsicum annuum L.) by a combination of LC-ESI(-)-MS/MS and polarity prediction in reversed-phase separations. Analytical and Bioanalytical Chemistry 412:3005-3015. CrossRef Paudel, L., F.J. Wyzgoski, J.C. Scheerens, A.M. Chanon, R.N. Reese, D. Smiljanic, C. Wesdemiotis, J.J. Blakeslee, K.M. Riedl & P.L. Rinaldi 2013. Nonanthocyanin secondary metabolites of black raspberry (Rubus occidentalis L.) fruits: identification by HPLC-DAD, NMR, HPLC-ESIMS, and ESI-MS/MS analyses. Journal of Agricultural and Food Chemistry 61(49):12032-12043. CrossRef Petsalo, A., J. Jalonen & A. Tolonen 2006. Identification of flavonoids of Rhodiola rosea by liquid chromatographytandem mass spectrometry. Journal of Chromatography A 1112(1-2):224-231. CrossRef Pharmacopoeia of the Eurasian Economic Union, approved by decision of the board of Eurasian Economic Commission No. 100 dated August 11, 2020. Available at: https://eec.eaeunion.org/upload/medialibrary/37c/PHARMACOPOEIA-of-the-Eurasian-Economic-Union.pdf Pradhan, P.C. & S. Saha 2016. Anthocyanin profiling of Berberis lycium Royle berry and its bioactivity evaluation for its nutraceutical potential. Journal of Food Science and Technology 53(2):1205-1213. CrossRef Qin, D., Q. Wang, H. Li, X. Jiang, K. Fang, Q. Wang, B. Li, C. Pan & H. Wu 2020. 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 Research International 138(B):109789. CrossRef Rafsanjany, N., J. Senker, S. Brandt, U. Dobrindt & A. Hensel 2015. In vivo consumption of cranberry exerts ex vivo antiadhesive activity against FimH-dominated uropathogenic Escherichia coli: A combined in vivo, ex vivo, and in vitro study of an extract from Vaccinium macrocarpon. Journal of Agricultural and Food Chemistry 63:8804-8818. CrossRef Razgonova, M.P., B.B. Bazhenova, Y.Y. Zabalueva, A.G. Burkhanova, A.M. Zakharenko & K.S. Golokhvast 2022. Rosa davurica Pall., Rosa rugosa Thumb., and Rosa acicularis Lindl. originating from Far Eastern Russia: Screening of 146 chemical constituents in three species of the genus Rosa. Applied Science 12:9401. CrossRef Razgonova, M.P., Z.M. Okhlopkova, Z.G. Rozhina, P.S. Egorova, S. Ercisli & K.S. Golokhvast 2022. Comparison of wild and introduced Dracocephalum jacutense P.: Significant differences of multicomponent compositions. Horticulturae 8:8228. CrossRef Razgonova, M.P., L.A. Tekutyeva, A.B. Podvolotskaya, V.D. Stepochkina, A.M. Zakharenko & K.S. Golokhvast 2022. Zostera marina L. supercritical CO2-extraction and mass spectrometric characterization of chemical constituents recovered from seagrass. Separations 9:182. CrossRef Razgonova, M.P., A.M. Zakharenko & K.S. Golokhvast 2022. Investigation of supercritical CO2-extracts of wild Ledum palustre L. (Rhododendron tomentosum Harmaja) and identification of its metabolites by tandem mass spectrometry. Khimiya Rastitel'nogo Syr'ya 1:179-191(in Russian with English summary). [Разгонова М.П., Захаренко А.М., Голохваст К.С. 2022. Исследование сверхкритических CO2-экстрактов багульника болотного Ledum palustre L. (Rhododendron tomentosum Harmaja) и идентификация его метаболитов методом тандемной масс-спектрометрии. // Химия растительного сырья. № 1. С.179-191]. CrossRef Razgonova, M.P., A.P. Boiko, Y.N. Zinchenko, N.G. Tikhonova, A.S. Sabitov, A.M. Zakharenko & K.S. Golokhvast 2023. Actinidia deliciosa: a high-resolution mass spectrometric approach for the comprehensive characterization of bioactive compounds. Turkish Journal of Agriculture and Forestry 47:155-169 CrossRef Razgonova, M.P., E.I. Cherevach, L.A. Tekutyeva, S.A. Fedoreev, N.P. Mishchenko, D.V. Tarbeeva, E.N. Demidova, N.S. Kirilenko & K.S. Golokhvast 2023. Maackia amurensis Rupr. et Maxim.: Supercritical CO2-extraction and mass spectrometric characterization of chemical constituents. Molecules 28:2026 CrossRef Ruiz, A., I. Hermosín-Gutiérrez, C. Vergara, D. von Baer, M. Zapata, A. Hitschfeld, L. Obando & C. Mardones 2013. Anthocyanin profiles in south Patagonian wild berries by HPLC-DAD-ESI-MS/MS. Food Research International 51(2):706-713. CrossRef Ruiz, A., I. Hermosin-Gutierrez, C. Mardones, C. Vergara, E. Herlitz, M. Vega, C. Dorau, P.; Winterhalter & D. von Baer 2010. Polyphenols and antioxidant activity of calafate (Berberis microphylla) fruits and other native berries from Southern Chile. Journal of Agricultural and Food Chemistry 51:706-713. CrossRef Said, R.B., A.I. Hamed, U.A. Mahalel, A.S. Al-Ayed, M. Kowalczyk, J. Moldoch, W. Oleszek & A. Stochmal 2017. Tentative characterization of polyphenolic compounds in the male flowers of Phoenix dactylifera by liquid chromatography coupled with mass spectrometry and DFT. International Journal of Molecular Science 18:512. CrossRef Salih, E., R. Julkunen-Tiitto, A.-M. Lampi, M. Kanninen, O. Luukkanen, M. Sipi, M. Lehtonen, H. Vuorela & P. Fyhrquist 2018. Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols. Journal of Ethnopharmacology 227:82-96. CrossRef Santo, I.E., A.S. Pedro, R. Fialho & E. Cabral-Albuquerque 2013. Characteristics of lipid micro- and nanoparticles based on supercritical formation for potential pharmaceutical application. Nanoscale Research Letters 8:386. CrossRef Seeram, N.P., R. Lee, H.S. Scheuller & D. Heber 2006. Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy. Food Chemistry 97:1-11. CrossRef Shakya, R. & D.A. Navarre 2008. LC-MS Analysis of solanidane glycoalkaloid diversity among tubers of four wild potato species and three cultivars (Solanum tuberosum). Journal of Agricultural and Food Chemistry 56:6949-6958. CrossRef Song, Y.-L., G.-S. Zhou, S.-X. Zhou, Y. Jiang & P.-F. Tu 2013. Polygalins D-G, four new flavonol glycosides from the aerial parts of Polygala sibirica L. (Polygalaceae). Natural Product Research 27(13):1220-1227. CrossRef Songserm, P., P. Klanrit, J. Phetcharaburanin, P. Thanonkeo, J. Apiraksakorn, K. Phomphrai & P. Klanrot 2022. Antioxidant and anticancer potential of bioactive compounds 2 from Rhinacanthus nasutus cell suspension culture. Plants 11:1994. CrossRef Spinola, V., J. Pinto & P.C. Castilho 2015. Identification and quantification of phenolic compounds of selected fruits from Madeira Island by HPLC-DAD-ESI-MSn and screening for their antioxidant activity. Food Chemistry 173:14-30. CrossRef Stallmann, J., R. Schweiger, C.A. Pons & C. Müller 2020. Wheat growth, applied water use efficiency and flag leaf metabolome under continuous and pulsed deficit irrigation. Scientific Reports 10(1):1-13. CrossRef Suarez Montenegro, Z.J., G. Alvarez-Rivera, J.A. Mendiola, E. Ibanez & A. Cifuentes 2021. Extraction and mass spectrometric characterization of terpenes recovered from olive leaves using a new adsorbent-assisted supercritical CO2 process. Foods 10:1301. CrossRef Sun, J., X. Liu, T. Yang, J. Slovin & P. Chen 2014. Profiling polyphenols of two diploid strawberry (Fragaria vesca) inbred lines using UHPLC-HRMSn. Food Chemistry 146:289-298. CrossRef Tandya, A., R. Mammucari, F. Dehghani & N.R. Foster 2007. Dense gas processing of polymeric controlled release formulations. International Journal Pharmaceutics 328:1-11. CrossRef Taskin, D., M. Ozdemir & B. Yalcin 2021. LC‑ESI‑tandem MS and in silico ADMET analysis of polyphenols from Rhus coriaria L. and Micromeria fruticosa (L.) Druce ssp. brachycalyx P.H. Davis. Future Journal Pharmaceutical Sciences 7:168. CrossRef Teles, Y.C.E., C.C. Rebello Horta, M. de Fatima Agra, W. Siheri, M. Boyd, J. O. Igoli, A.I. Gray, M. de Fatima Vanderlei de Souza 2015. New sulphated flavonoids from Wissadula periplocifolia (L.) C. Presl (Malvaceae). Molecules 20:20161-20172. CrossRef Trifan, A., G. Zengin, K.I. Sinan, E. Sieniawska, R. Sawicki, M. Maciejewska-Turska, K. Skalikca-Wozniak & S.V. Luca 2022. Unveiling the phytochemical profile and biological potential of five Artemisia species. Antioxidants 11:1017. CrossRef Urbanova, T., D. Tarkowska, O. Novak, P. Hedden & M. Strnad 2013. Analysis of gibberellins as free acids by ultra-performance liquid chromatography-tandem mass spectrometry. Talanta 112:85-94. CrossRef van Breemen, R.B., F.L. Canjura & S.J. Schwartz 1991. Identification of chlorophyll derivatives by mass spectrometry. Journal of Agricultural and Food Chemistry 39:1452-1456. CrossRef Van Hoyweghen, L., K. De Bosscher, G. Haegeman, D. Deforce & A. Heyerick 2014. In vitro inhibition of the transcription factor NF-kB and cyclooxygenase by bamboo extracts. Phytotherapy Research 28:224-230. CrossRef Vijayan, K.P.R. & A.V. Raghu 2019. Tentative characterization of phenolic compounds in three species of the genus Embelia by liquid chromatography coupled with mass spectrometry analysis. Spectroscopy Letters 52(10):653-670. CrossRef Voroshilova, M. 2021. Image of Ribes fragrans Pall. In: Plantarium. Plants and lichens of Russia and neighboring countries: open online galleries and plant identification guide. URL: https://www.plantarium.ru/lang/en/page/image/id/709909.html (accessed on 4 Aug 2024). Voskoboinikova, I.V., N.A. Tjukavkina, S.V. Geodakyan, Y.A. Kolesnik, V.K. Kolhir, V.A. Zjuzin & S.J. Sokolov 1993. Experimental pharmacokinetics of biologically active plant phenolic compounds III. Pharmacokinetics of dihydroquercetin. Phytotherapy Research 7:208-210. CrossRef Wang, F., S. Zhao, F. Li, B. Zhang, Y. Qu, T. Sun, T. Luo & D. Li 2014. Investigation of antioxidant 'interactions between Radix Astragali and Cimicifuga foetida and identification of synergistic antioxidant compounds. PlosONE 9:e87221. CrossRef Wang, Y., N. Vorsa, P. Harrington & P. Chen 2018. Nontargeted metabolomic study on variation of phenolics in different cranberry cultivars using UPLC-IM − HRMS. Journal of Agricultural and Food Chemistry 66:12206-12216. CrossRef Wojakowska, A., A. Piasecka, P.M. Garcia-Lopez, F. Zamora-Natera, P. Krajewski, L. Marczak, P. Kachlicki & M. Stobiecki 2013. Structural analysis and profiling of phenolic secondary metabolites of Mexican lupine species using LC-MS techniques. Phytochemistry 92:71-86. CrossRef Xu, X., B. Yang, D. Wang, Y. Zhu, X. Miao & W. Yang 2020. The chemical composition of Brazilian green propolis and its protective effects on mouse aortic endothelial cells against inflammatory injury. Molecules 25:4612. CrossRef Xu, L. L., J.J. Xu, K.R. Zhong, Z.P. Shang, F. Wang, R.F. Wang & B. Liu 2017. Analysis of non-volatile chemical constituents of Menthae Haplocalycis herba by ultra-high performance liquid chromatography - high resolution mass spectrometry. Molecules 22:1756. CrossRef Yang, S.T., X. Wu, W. Rui, J. Guo & Y.F. Feng 2015. UPLC/Q-TOF-MS Analysis for identification of hydrophilic phenolics and lipophilic diterpenoids from Radix Salviae Miltiorrhizae. Acta Chromatographica 27(4):711-728. CrossRef Yin, N.-W., S.-X. Wang, L.-D. Jia, M.-C. Zhu, J. Yang, B.-J. Zhou, J.-M. Yin, K. Lu, R. Wang, J.-N. Li & C.-M. Qu 2019. Identification and characterization of major constituents in different-colored rapeseed petals by UPLC−HESI-MS/MS. Journal of Agricultural and Food Chemistry 67:11053-11065. CrossRef Yin, Y., K. Zhang, L. Wei, D. Chen, Q. Chen, M. Jiao, X. Li, J. Huang, Z. Gong, N. Kang & F. Li 2021. The molecular mechanism of antioxidation of Huolisu oral liquid based on serum analysis and network analysis. Frontiers in Pharmacology 12:710976. CrossRef Zapesochnaya, G.G., V.A. Kurkin & A.N. Shchavlinskii 1985. Flavonoids of the above-ground part of Rhodiola rosea. II. Structure of novel glycosides of herbacetin and gossypetin. Chemistry of Natural Compounds 4:496-507. CrossRef Zengin, G., M.F. Mahomoodally, K.I. Sinan, G. Ak, O.K. Etienne, J.B. Sharmeen, L. Brunetti, S. Leone, S.C. Di Simone, L. Recinella, A. Chiavaroli & L. Menghini 2021. Chemical composition and biological properties of two Jatropha species: Different parts and different extraction methods. Antioxidants 10:792. CrossRef Zhang, D., T. Miyase, M. Kuroyanagi, K. Umehara & H. Noguchi 1998. Oligosaccharide polyesters from roots of Polygala glomerata. Phytochemistry 47(1):45-52. CrossRef Zhang, J., X.-J. Xu, W. Xu, J. Huang, D. Zhu & X.-H. Qiu 2014. Rapid characterization and identification of flavonoids in Radix Astragali by ultra-high-pressure liquid chromatography coupled with linear ion trap-orbitrap mass spectrometry. Journal of Chromatographic Science 53:945-952. CrossRef Zhao, Y., H. Lu, Q. Wang, H. Liu, H. Shen, W. Xu, J. Ge & D. He 2021. Rapid qualitative profiling and quantitative analysis of phenolics in Ribes meyeri leaves and their antioxidant and antidiabetic activities by HPLC-QTOFMS/MS and UHPLC-MS/MS. Journal of Separation Science 44:1404-1420. CrossRef
|