Volume 14 Issue 11
Nov.  2024
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Li Jia, Liming Wang, Xiaoxiao Zhang, Qingrui Zhang, Peng Lei, Yanxu Chang, Lifeng Han, Xin Chai, Wenzhi Yang, Yuefei Wang, Miaomiao Jiang. Investigation of oligomeric proanthocyanidins extracted from Rhodiolae Crenulatae Radix et Rhizomes using deep eutectic solvents and identified via data-dependent acquisition mass-spectroscopy[J]. Journal of Pharmaceutical Analysis, 2024, 14(11): 101002. doi: 10.1016/j.jpha.2024.101002
Citation: Li Jia, Liming Wang, Xiaoxiao Zhang, Qingrui Zhang, Peng Lei, Yanxu Chang, Lifeng Han, Xin Chai, Wenzhi Yang, Yuefei Wang, Miaomiao Jiang. Investigation of oligomeric proanthocyanidins extracted from Rhodiolae Crenulatae Radix et Rhizomes using deep eutectic solvents and identified via data-dependent acquisition mass-spectroscopy[J]. Journal of Pharmaceutical Analysis, 2024, 14(11): 101002. doi: 10.1016/j.jpha.2024.101002

Investigation of oligomeric proanthocyanidins extracted from Rhodiolae Crenulatae Radix et Rhizomes using deep eutectic solvents and identified via data-dependent acquisition mass-spectroscopy

doi: 10.1016/j.jpha.2024.101002
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This work was supported by the Science and Technology Program of Tianjin in China (Grant No.: 23ZYJDSS00030) and the Science and Technology Project of Haihe Laboratory of Modern Chinese Medicine, China (Grant Nos.: 22HHZYSS00007 and 22HHZYJC00003).

  • Received Date: Jul. 23, 2023
  • Accepted Date: May 09, 2024
  • Rev Recd Date: May 05, 2024
  • Publish Date: May 11, 2024
  • In this study, 34 deep eutectic solvents (DESs) were successfully prepared for the extraction of proanthocyanidin from Rhodiolae Crenulatae Radix et Rhizomes. The extraction process was optimized using single factor exploration and Box-Behnken design-response surface analysis. The extraction rate was significantly improved when the molar ratio of choline chloride to 1,3-propanediol was 1:3.5 and the water content was 30% (V/V) in DESs. AB-8 macroporous resin and ethyl acetate were used for separation and refining, and the oligomer-rich proanthocyanidin components were eventually obtained. The ultraviolet (UV) and infrared (IR) spectra showed that the proanthocyanidins were mainly composed of catechin and epicatechin. To further clarify the chemical composition of proanthocyanidin, an ion scan list containing 156 proanthocyanidins precursors was obtained by constructing a proanthocyanidins structural library and mass defect filtering (MDF) algorithm, combined with the full mass spectrometry (MS)/dd-MS2 scan mode that turns on the “if idle pick others” function. By using ultra-high performance liquid chromatography and high-resolution MS (UHPLC/HRMS), the analysis used both targeted and non-targeted methods to detect proanthocyanidins. Finally, 50 oligomeric proanthocyanidin (OPC) compounds were identified, including 7 monomers, 22 dimers, 20 trimers, and 1 tetramer, most of which were procyanidins of proanthocyanidins (84%), and a small amount of prodelphinidin (14%) and other types of proanthocyanidins (2%), which enabled the systematic characterization of proanthocyanidin components from Rhodiolae Crenulatae Radix et Rhizomes. Meanwhile, the comparison with the grape seeds OPCs standard (United States Pharmacopeia) revealed that the proanthocyanidins in Rhodiolae Crenulatae Radix et Rhizomes were more abundant, suggesting that the proanthocyanidins in Rhodiolae Crenulatae Radix et Rhizomes has promising applications.
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  • [1]
    D. Ma, L. Wang, Y. Jin, et al., Chemical characteristics of Rhodiola crenulata and its mechanism in acute mountain sickness using UHPLC-Q-TOF-MS/MS combined with network pharmacology analysis, J. Ethnopharmacol. 294 (2022), 115345.
    [2]
    X. Bai, X. Deng, G. Wu, et al., Rhodiola and salidroside in the treatment of metabolic disorders, Mini Rev. Med. Chem. 19 (2019) 1611-1626.
    [3]
    W. Pu, M. Zhang, R. Bai, et al., Anti-inflammatory effects of Rhodiola rosea L.: A review, Biomed. Pharmacother. 121 (2020), 109552.
    [4]
    H.I. Chen, H.C. Ou, C.Y. Chen, et al., Neuroprotective effect of Rhodiola crenulata in D-galactose-induced aging model, Am. J. Chin. Med. 48 (2020) 373-390.
    [5]
    D.N. Olennikov, N.K. Chirikova, A.G. Vasilieva, et al., LC-MS profile, gastrointestinal and gut microbiota stability and antioxidant activity of Rhodiola rosea herb metabolites: A comparative study with subterranean organs, Antioxidants 9 (2020), 526.
    [6]
    S. Toro-Uribe, M. Herrero, E.A. Decker, et al., Preparative separation of procyanidins from cocoa polyphenolic extract: Comparative study of different fractionation techniques, Molecules 25 (2020), 2842.
    [7]
    J.F. Hammerstone, S.A. Lazarus, A.E. Mitchell, et al., Identification of procyanidins in cocoa (Theobroma cacao) and chocolate using high-performance liquid chromatography/mass spectrometry, J. Agric. Food Chem. 47 (1999) 490-496.
    [8]
    N. Hellenbrand, J. Sendker, M. Lechtenberg, et al., Isolation and quantification of oligomeric and polymeric procyanidins in leaves and flowers of Hawthorn (Crataegus spp.), Fitoterapia 104 (2015) 14-22.
    [9]
    T. Song, P. Wang, C. Li, et al., Salidroside simultaneously reduces de novo lipogenesis and cholesterol biosynthesis to attenuate atherosclerosis in mice, Biomed. Pharmacother. 134 (2021), 111137.
    [10]
    H. Chen, J. Zhu, Y. Le, et al., Salidroside inhibits doxorubicin-induced cardiomyopathy by modulating a ferroptosis-dependent pathway, Phytomedicine 99 (2022), 153964.
    [11]
    L. Rong, Z. Li, X. Leng, et al., Salidroside induces apoptosis and protective autophagy in human gastric cancer AGS cells through the PI3K/Akt/mTOR pathway, Biomed. Pharmacother. 122 (2020), 109726.
    [12]
    S. Zhao, L. Zhang, C. Yang, et al., Procyanidins and Alzheimer’s disease, Mol. Neurobiol. 56 (2019) 5556-5567.
    [13]
    E.A. Rue, M.D. Rush, R.B. van Breemen, Procyanidins: A comprehensive review encompassing structure elucidation via mass spectrometry, Phytochem. Rev. 17 (2018) 1-16.
    [14]
    Z. Chen, J. Tan, J. Qin, et al., Effects of lotus seedpod oligomeric procyanidins on the inhibition of AGEs formation and sensory quality of tough biscuits, Front. Nutr. 9 (2022), 1031550.
    [15]
    Y. Sui, J. Shi, S. Cai, et al., Metabolites of procyanidins from Litchi chinensis pericarp with xanthine oxidase inhibitory effect and antioxidant activity, Front. Nutr. 8 (2021), 676346.
    [16]
    D. Ferreira, D. Slade, Oligomeric proanthocyanidins: Naturally occurring O-heterocycles, Nat. Prod. Rep. 19 (2002) 517-541.
    [17]
    A. Tuominen, M. Karonen, Variability between organs of proanthocyanidins in Geranium sylvaticum analyzed by off-line 2-dimensional HPLC-MS, Phytochemistry 150 (2018) 106-117.
    [18]
    J.A. Kennedy, G.P. Jones, Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol, J. Agric. Food Chem. 49 (2001) 1740-1746.
    [19]
    T. Mohana, A.V. Navin, S. Jamuna, et al., Inhibition of differentiation of monocyte to macrophages in atherosclerosis by oligomeric proanthocyanidins – In-vivo and in-vitro study, Food Chem. Toxicol. 82 (2015) 96-105.
    [20]
    N. Hellenbrand, M. Lechtenberg, F. Petereit, et al., Isolation and quantification of oligomeric and polymeric procyanidins in the aerial parts of St. John’s wort (Hypericum perforatum), Planta Med. 81 (2015) 1175-1181.
    [21]
    K. Schotz, M. Noldner, Mass spectroscopic characterisation of oligomeric proanthocyanidins derived from an extract of Pelargonium sidoides roots (EPs 7630) and pharmacological screening in CNS models, Phytomedicine 14 (2007) 32-39.
    [22]
    W. Tao, H. Pan, H. Jiang, et al., Extraction and identification of proanthocyanidins from the leaves of persimmon and loquat, Food Chem. 372 (2022), 130780.
    [23]
    J. Cao, L. Chen, M. Li, et al., Efficient extraction of proanthocyanidin from Ginkgo biloba leaves employing rationally designed deep eutectic solvent-water mixture and evaluation of the antioxidant activity, J. Pharm. Biomed. Anal. 158 (2018) 317-326.
    [24]
    A.R. Jesus, L. Meneses, A.R.C. Duarte, et al., Natural deep eutectic systems, an emerging class of cryoprotectant agents, Cryobiology 101 (2021) 95-104.
    [25]
    A.P. Abbott, K.J. Edler, A.J. Page, Deep eutectic solvents-The vital link between ionic liquids and ionic solutions, J. Chem. Phys. 155 (2021), 150401.
    [26]
    J.M. Hartley, S. Scott, Z. Dilruba, et al., Iodine speciation in deep eutectic solvents, Phys. Chem. Chem. Phys. 24 (2022) 24105-24115.
    [27]
    M. Zhang, X. Zhang, Y. Liu, et al., Insights into the relationships between physicochemical properties, solvent performance, and applications of deep eutectic solvents, Environ. Sci. Pollut. Res. Int. 28 (2021) 35537-35563.
    [28]
    J.K.U. Ling, K. Hadinoto, Deep eutectic solvent as green solvent in extraction of biological macromolecules: A review, Int. J. Mol. Sci. 23 (2022), 3381.
    [29]
    L.E. Meyer, M.B. Andersen, S. Kara, A deep eutectic solvent thermomorphic Multiphasic system for biocatalytic applications, Angew. Chem. Int. Ed. Engl. 61 (2022), e202203823.
    [30]
    F. Wang, J. Zhang, P. Yin, et al., Rapid identification of polyphenols in Kudiezi injection with a practical technique of mass defect filter based on high-performance liquid chromatography coupled with linear ion trap/orbitrap mass spectrometry, Anal. Methods 6 (2014) 3515-3523.
    [31]
    L.-Z. Lin, J. Sun, P. Chen, et al., UHPLC-PDA-ESI/HRMSn profiling method to identify and quantify oligomeric proanthocyanidins in plant products, J. Agric. Food Chem. 62 (2014) 9387-9400.
    [32]
    Y. Dai, E. Rozema, R. Verpoorte, et al., Application of natural deep eutectic solvents to the extraction of anthocyanins from Catharanthus roseus with high extractability and stability replacing conventional organic solvents, J. Chromatogr. A 1434 (2016) 50-56.
    [33]
    Y. Dai, G.J. Witkamp, R. Verpoorte, et al., Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L, Anal. Chem. 85 (2013) 6272-6278.
    [34]
    Z. Yang, Natural deep eutectic solvents and their applications in biotechnology, Adv. Biochem. Eng. 168 (2019) 31-59.
    [35]
    M. Ruesgas-Ramon, M.C. Figueroa-Espinoza, E. Durand, Application of deep eutectic solvents (DES) for phenolic compounds extraction: Overview, challenges, and opportunities, J. Agric. Food Chem. 65 (2017) 3591-3601.
    [36]
    M.H. Zainal-Abidin, M. Hayyan, A. Hayyan, et al., New horizons in the extraction of bioactive compounds using deep eutectic solvents: A review, Anal. Chim. Acta 979 (2017) 1-23.
    [37]
    N. Guo, P. Kou, Y. Jiang, et al., Natural deep eutectic solvents couple with integrative extraction technique as an effective approach for mulberry anthocyanin extraction, Food Chem. 296 (2019) 78-85.
    [38]
    N. Symma, A. Hensel, Advanced analysis of oligomeric proanthocyanidins: Latest approaches in liquid chromatography and mass spectrometry based analysis, Phytochem. Rev. 21 (2022) 809-833.
    [39]
    L. Jia, H. Wang, X. Xu, et al., An off-line three-dimensional liquid chromatography/Q-Orbitrap mass spectrometry approach enabling the discovery of 1561 potentially unknown ginsenosides from the flower buds of Panax ginseng, Panax quinquefolius and Panax notoginseng, J. Chromatogr. A 1675 (2022), 463177.
    [40]
    S. Rozas, C. Benito, R. Alcalde, et al., Insights on the water effect on deep eutectic solvents properties and structuring: The archetypical case of choline chloride + ethylene glycol, J. Mol. Liq. 344 (2021), 117717.
    [41]
    A. Shishov, S. Gagarionova, A. Bulatov, Deep eutectic mixture membrane-based microextraction: HPLC-FLD determination of phenols in smoked food samples, Food Chem. 314 (2020), 126097.
    [42]
    A.P. Neilson, S.F. O’Keefe, B.W. Bolling, High-molecular-weight proanthocyanidins in foods: Overcoming analytical challenges in pursuit of novel dietary bioactive components, Annu. Rev. Food Sci. Technol. 7 (2016) 43-64.
    [43]
    A. Rauf, M. Imran, T. Abu-Izneid, et al., Proanthocyanidins: A comprehensive review, Biomed. Pharmacother. 116 (2019), 108999.
    [44]
    Y. Takahata, M. Ohnishi-Kameyama, S. Furuta, et al., Highly polymerized procyanidins in brown soybean seed coat with a high radical-scavenging activity, J. Agric. Food Chem. 49 (2001) 5843-5847.
    [45]
    M. Bensa, V. Glavnik, I. Vovk, Flavan-3-ols and proanthocyanidins in Japanese, Bohemian and giant knotweed, Plants 10 (2021), 402.
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