An extraction- assay system: Evaluation on flavonols in plant resistance to Pb and Cd by supercritical extraction- gas chromatography

Abstract

SFE-GC system is established for flavonols assessment.

Optimal parameters of SFE-GC are evaluated and determined.

Quercetin and kaempferol are detected in plant under heavy metal stress.

Gene expression analysis shows consistent regularity with content of flavonols.

ROS level is applied for elaborating the plant resistance status.

In this research, supercritical carbon dioxide extraction (SFE) showed better extraction effect when compared with Solid- liquid extraction (SLE), Soxhlet extraction (SE) and Ultrasonic extraction (UE), not only in the rate but also the time. The comparison among these three extraction modifiers, including acetone, ethanol and methanol demonstrated that ethanol was preferred to SFE due to its high extraction effect and low toxicology. In addition, parameter of SFE, influence of temperature and pressure were investigated, and the best extraction effect was achieved at the optima conditions, temperature of 40°C and the pressure of 35 Mpa. Thus, SFE is a highly effective method for flavonols extraction, requiring minimum energy and producing non-toxic byproduct. SFE-GC system is applied for the evaluation on flavonols that plays a key role in plant resistance to heavy metal, with its content and synthetase gene expression significantly increasing in plant when threatened by heavy metal. Besides, results indicated that flavonols can improve plant resistance to oxidative stress by quenching the redundant ROS in matrix.

Graphical abstract

Keywords

Flavonols / Heavy metal / Supercritical carbon dioxide extraction (SFE) / GC / Plant resistance

References

[1] Benaventegarcía O, Castillo J (2008). Update on uses and properties of citrus flavonoids: New findings in anticancer, cardiovascular, and anti-inflammatory activity. Journal of Agricultural and Food Chemistry, 56(15): 6185–6205

[2] Bogdanov M G, Svinyarov I, Keremedchieva R, Sidjimov A (2012). Ionic liquid-supported solid‒liquid extraction of bioactive alkaloids. I. New HPLC method for quantitative determination of glaucine in Glaucium flavum Cr. (Papaveraceae). Separation and Purification Technology, 97: 221–227

[3] Dauner M, Sauer U (2000). GC-MS Analysis of amino acids rapidly provides rich information for isotopomer balancing. Biotechnology Progress, 16(4): 642–649

[4] Diet A, Link B, Seifert G J, Schellenberg B, Wagner U, Pauly M, Reiter W D, Ringli C (2006). The Arabidopsis root hair cell wall formation mutant LRX1 is suppressed by mutations in the RHM1 gene encoding a UDP-l-rhamnose synthase. Plant Cell, 18(7): 1630– 1641

[5] El-Aty A M A, Choi J H, Ko M W, Khay S, Goudah A, Shin H C, Kim J S, Chang B J, Lee C H, Shim J H (2009). Approaches for application of sub and supercritical fluid extraction for quantification of orbifloxacin from plasma and milk: Application to disposition kinetics. Analytica Chimica Acta, 631(1): 108–115

[6] Emteborg H, Björklund E, Ödman F, Karlsson L, Mathiasson L, Frech W, Baxter D C (2016). Determination of methylmercury in sediments using supercritical fluid extraction and gas chromatography coupled with microwave-induced plasma atomic emission spectrometry. Analyst (London), 121(1): 19–29

[7] Espinosa-Pardo F A, Nakajima V M, Macedo G A, Macedo J A, Martínez J (2016). Extraction of phenolic compounds from dry and fermented orange pomace using supercritical CO₂ and cosolvents. Food and Bioproducts Processing, 101: 1–10

[8] Ferrentino G, Calliari N, Bertucco A, Spilimbergo S (2014). Validation of a mathematical model for predicting high pressure carbon dioxide inactivation kinetics of Escherichia coli spiked on fresh cut carrot. Journal of Supercritical Fluids, 85: 17–23

[9] Hossein K, Karamatollah R (2009). Effect of various parameters on the selective extraction of main components from hyssop using supercritical fluid extraction (SFE). Food Science and Technology Research, 15(6): 645–652

[10] Houben R J, Janssen H G M, Leclercq P A, Rijks J A, Cramers C A (2015). Supercritical fluid extraction‐capillary gas chromatography: On‐line coupling with a programmed temperature vaporizer. Journal of Separation Science, 13: 669–673

[11] Hu Y, Li C, Kulkarni B A, Strobel G, Lobkovsky E, Torczynski R M Jr P J (2001). Exploring chemical diversity of epoxyquinoid natural products: Synthesis and biological activity of (-)-jesterone and related molecules. Organic Letters, 3(11), 1649–1652

[12] Jaakola L, Hohtola A (2010). Effect of latitude on flavonoid biosynthesis in plants. Plant, Cell & Environment, 33: 1239

[13] Jaramillo K, Dawid C, Hofmann T, Fujimoto Y, Osorio C (2011). Identification of antioxidative flavonols and anthocyanins in Sicana odorifera fruit peel. Journal of Agricultural and Food Chemistry, 59(3): 975–983

[14] Jungbluth G, Ternes W (2000). HPLC separation of flavonols, flavones and oxidized flavonols with UV-, DAD-, electrochemical and ESI-ion trap MS detection. Fresenius’ Journal of Analytical Chemistry, 367(7): 661–666

[15] Kamali H, Ghaziaskar H S, Khakshour A, Kaboudvand M (2013). Supercritical CO₂ extraction of phthalic anhydride, benzoic acid and maleic acid from petrochemical wastes. Journal of Supercritical Fluids, 74: 46–51

[16] Katherine L S, Edgar C C, Jerry W K, Luke R H, Julie C D (2008). Extraction conditions affecting supercritical fluid extraction (SFE) of lycopene from watermelon. Bioresource Technology, 99(16): 7835–7841

[17] Kazazi H, Rezaei K, Ghotb-Sharif S J, Emam-Djomeh Z, Yamini Y (2007). Supercriticial fluid extraction of flavors and fragrances from Hyssopus officinalis L. cultivated in Iran. Food Chemistry, 105(2): 805–811

[18] Kuhn B M, Geisler M, Bigler L, Ringli C (2011). Flavonols accumulate asymmetrically and affect auxin transport in Arabidopsis. Plant Physiology, 156(2): 585–595

[19] Kumar P, Pal A, Saxena M K, Ramakumar K L (2008). Supercritical fluid extraction of uranium and thorium from solid matrices. Desalination, 232(1-3): 71–79

[20] Kutchko B G, Goodman A L, Rosenbaum E, Natesakhawat S, Wagner K (2013). Characterization of coal before and after supercritical CO₂ exposure via feature relocation using field-emission scanning electron microscopy. Fuel, 107: 777–786

[21] Lummaetee K, Ku H M, Wongrat W, Elkamel A (2017). Optimization of supercritical fluid extraction of isoflavone from soybean meal. Canadian Journal of Chemical Engineering, 95(6): 1141–1149

[22] Maran J P, Manikandan S, Priya B, Gurumoorthi P (2015). Box-Behnken design based multi-response analysis and optimization of supercritical carbon dioxide extraction of bioactive flavonoid compounds from tea (Camellia sinensis L.) leaves. Journal of Food Science and Technology, 52(1): 92–104

[23] Mason J T, Chemat F, Vinatoru M (2016). The extraction of natural products using ultrasound or microwaves. Current Organic Chemistry, 15: 237–247

[24] Modey W K, Mulholland D A, Raynor M W( 2015). Analytical supercritical fluid extraction of natural products. Phytochemical Analysis, 7(1): 1–15

[25] Pan H, Zhang X, Ren B, Yang H, Ren Z, Wang W (2017). Toxic assessment of cadmium based on online swimming behavior and the continuous AChE activity in the gill of Zebrafish (Danio rerio). Water, Air, and Soil Pollution, 228(9): 355

[26] Rajagopalan R, Vaucheret H, Trejo J, Bartel D P (2006). A diverse and evolutionarily fluid set of microRNAs in Arabidopsis thaliana. Genes & Development, 20(24): 3407–3425

[27] Ren Z (2015). Characterizing response behavior of medaka (Oryzias latipes) under chemical stress based on self-organizing map and filtering by integration. Ecological Informatics, 29: 107–118

[28] Shen J, Shao X (2005). A comparison of accelerated solvent extraction, Soxhlet extraction, and ultrasonic-assisted extraction for analysis of terpenoids and sterols in tobacco. Analytical and Bioanalytical Chemistry, 383(6): 1003–1008

[29] Skerget M, Kotnik P, Hadolin M, Hras A R, Simonic M, Knez Z (2005). Phenols, proanthocyanidins, flavones and flavonols in some plant materials and their antioxidant activities. Food Chemistry, 89(2): 191–198

[30] Spence A J, Jimenez-Flores R, Qian M, Goddik L( 2009). The influence of temperature and pressure factors in supercritical fluid extraction for optimizing nonpolar lipid extraction from buttermilk powder. Journal of Dairy Science, 2009, 92(2): 458–468

[31] Sung S, Amasino R M (2004). Vernalization in Arabidopsis thaliana is mediated by the PHD finger protein VIN3. Nature, 427(6970): 159–164

[32] Suzuki N, Koussevitzky S, Mittler R, Miller G (2012). ROS and redox signalling in the response of plants to abiotic stress. Plant, Cell & Environment, 35(2): 259–270

[33] Taher H, Al-Zuhair S, Al-Marzouqi A H, Haik Y, Farid M (2014). Mass transfer modeling of Scenedesmus sp. lipids extracted by supercritical CO₂. Biomass and Bioenergy, 70: 530–541

[34] Veggi P C, Cavalcanti R N, Meireles M A A (2011). Modifier effects on supercritical fluid extraction (SFE) of some Brazilian plants: Antioxidant activity and economical evaluation. Procedia Food Science, 1: 1717–1724

[35] Wang W, Dong C, Dong W, Yang C, Ju T, Huang L, Ren Z (2016). The design and implementation of risk assessment model for hazard installations based on AHP–FCE method: A case study of Nansi Lake Basin. Ecological Informatics, 36: 162–171

[36] Xing N, Ji L, Song J, Ma J, Li S, Ren Z, Xu F, Zhu J( 2017). Cadmium stress assessment based on the electrocardiogram characteristics of zebra fish (Danio rerio): QRS complex could play an important role. Aquatic Toxicology (Amsterdam, Netherlands), 191: 236–244

[37] Yang C, Ming Z, Dong W, Cui G, Ren Z, Wang W( 2017). Highly efficient photocatalytic degradation of methylene blue by PoPD/TiO₂ nanocomposite. PLoS One, 12(3): e0174104

[38] Yin L, Yang H, Si G, Ren Q, Fu R, Zhang B, Zhang X, Wang X, Qi P, Xia C( 2015). Persistence parameter: A reliable measurement for behavioral responses of Medaka (Oryzias latipes) to Environmental Stress. Environmental Modeling and Assessment, 21: 1–9

[39] Ren Z, Zhang X, Wang X, Qi P, Zhang B, Zeng Y (2015). AChE inhibition: One dominant factor for swimming behavior changes of Daphnia magna under DDVP exposure. Chemosphere, 120, 252

[40] Zhang Q, Li Y, Phanlavong P, Wang Z, Jiao T, Qiu H, Peng Q (2017a). Highly efficient and rapid fluoride scavenger using an acid/base tolerant zirconium phosphate nanoflake: Behavior and mechanism. Journal of Cleaner Production, 161: 317–326

[41] Zhang Q, Li Y, Yang Q, Chen H, Chen X, Jiao T, Peng Q (2017b). Distinguished Cr(VI) capture with rapid and superior capability using polydopamine microsphere: Behavior and mechanism. Journal of Hazardous Materials, 342: 732–740

[42] Zhang X, Li X, Yang H, Cui Z (2018a). Biochemical mechanism of phytoremediation process of lead and cadmium pollution with Mucor circinelloides and Trichoderma asperellum. Ecotoxicology and Environmental Safety, 157: 21–28

[43] Zhang X, Ren B, Li S, Qu X, Yang H, Xu S, Ren Z, Kong Q, Wang C (2017c). Is sodium percarbonate a good choice in situ remediation of deltamethrin pollution? Frontiers of Environmental Science & Engineering, 11(3): 3

[44] Zhang X, Yang H, Cui Z (2016). A new indicator to evaluate the pollution of iron and manganese. RSC Advances, 6(33): 27963–27968

[45] Zhang X, Yang H, Cui Z (2017d). Alleviating effect and mechanism of flavonols in Arabidopsis resistance under Pb–HBCD stress. ACS Sustainable Chemistry & Engineering, 5(11): 11034–11041

[46] Zhang X, Yang H, Cui Z( 2018b). Evaluation and analysis of soil migration and distribution characteristics of heavy metals in iron tailings. Journal of Cleaner Production, 172: 475–480

RIGHTS & PERMISSIONS

Higher Education Press and Springer-Verlag GmbH Germany, part of Springer Nature