The effect of 2-hydroxypropyl β-cyclodextrin on the stability of polyphenolic compounds from Moringa oleifera Lam leaf extracts in a natural low-transition temperature mixture

Open access

Abstract

Polyphenol extracts from Moringa oleifera leaves (MoL) were obtained with a glycerol-based low-transition temperature mixture (LTTM) and a combination of LTTM with 2-hydroxypropyl β-cyclodextrin (HP-β-CD). The extracts were maintained at 4, 22 and 50 °C for 18 days and the antiradical activity (AAR) was recorded to detect modifications in the antioxidant activity of the extracts. AAR displayed a constant decline at every temperature tested, following pseudo first-order kinetics and the decay constants suggested that the presence of HP-β-CD had a protective action, slowing down AAR decline. The analysis of the polyphenolic profiles using liquid chromatography-diode array-mass spectrometry revealed that after storage for 18 days at 50 °C, the major quercetin glycosides occurring in MoL were extensively degraded. Based on the detection of protocatechuic acid in the stored extracts, putative pathways of flavonol glycoside degradation were proposed. It was concluded that the decomposition of these components was mainly responsible for the AAR decline observed.

If the inline PDF is not rendering correctly, you can download the PDF file here.

  • Alvarez-Parrilla E Laura A Torres-Rivas F Rodrigo-Garcia J González-Aguilar GA (2005) Complexation of apple antioxidants: chlorogenic acid quercetin and rutin by β-cyclodextrin (β-CD). J. Inclus. Phenom. Macrocycl. Chem. 53: 121-129.

  • Bi W Tian M Row KH (2013) Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. J. Chrom. A 1285: 22-30.

  • Çelik SE Özyürek M Güçlü K Apak R (2015) Antioxidant capacity of quercetin and its glycosides in the presence of β-cyclodextrins: influence of glycosylation on inclusion complexation. J. Inclus. Phenom. Macrocycl. Chem. 83: 309-319.

  • Çelik SE Özyürek M Tufan AN Güçlü K Apak R (2011) Spectroscopic study and antioxidant properties of the inclusion complexes of rosmarinic acid with natural and derivative cyclodextrins. Spectrochim. Acta Part A: Mol. Biomol. Spectr. 78: 1615-1624.

  • Farooq F Rai M Tiwari A Khan AA Farooq S (2012) Medicinal properties of Moringa oleifera: An overview of promising healer. J. Med. Plants Res. 6: 4368-4374.

  • Huang D Ou B Prior RL (2005) The chemistry behind antioxidant capacity assays. J. Agric. Food Chem. 53:1841-1856.

  • Jeong KM Ko J Zhao J Jin Y Yoo DE Han SY Lee J (2017) Multi-functioning deep eutectic solvents as extraction and storage media for bioactive natural products that are readily applicable to cosmetic products. J. Clean. Prod. 151: 87-95

  • Jullian C Miranda S Zapata-Torres G Mendizábal F Olea-Azar C (2007) Studies of inclusion complexes of natural and modified cyclodextrin with (+) catechin by NMR and molecular modeling. Bioorg. Med. Chem. 15: 3217-3224.

  • Kalogeropoulos N Yannakopoulou K Gioxari A Chiou A Makris DP (2010) Polyphenol characterization and encapsulation in β-cyclodextrin of a flavonoid-rich Hypericum perforatum (St John's wort) extract. LWT-Food Sci. Technol. 43: 882-889.

  • Karageorgou I Grigorakis S Lalas S Makris DP (2017) Enhanced extraction of antioxidant polyphenols from Moringa oleifera Lam. leaves using a biomolecule-based low-transition temperature mixture. Eur. Food Res. Technol. 243: 1839-1848.

  • Karageorgou I Grigorakis S Lalas S Mourtzinos I Makris DP (2018). Incorporation of 2-hydroxypropyl β-cyclodextrin in a biomolecule-based low-transition temperature mixture (LTTM) boosts efficiency of polyphenol extraction from Moringa oleifera Lam leaves. J. Applied Res. Med. Arom. Plants 9: 62-69.

  • Lalas S Athanasiadis V Karageorgou I Batra G Nanos GD Makris DP (2017) Nutritional characterization of leaves and herbal tea of Moringa oleifera cultivated in Greece. J. Herbs Spices Med. Plants: 24: 320-333.

  • Liu J Qiu L Gao J Jin Y (2006) Preparation characterization and in vivo evaluation of formulation of baicalein with hydroxypropyl-β-cyclodextrin. Inter. J. Pharm. 312: 137-143.

  • Lucas-Abellán C Fortea M Gabaldón J Núñez-Delicado E (2008) Complexation of resveratrol by native and modified cyclodextrins: determination of complexation constant by enzymatic solubility and fluorimetric assays. Food Chem. 111: 262-267.

  • Makris DP Rossiter JT (2000) Heat-induced metal-catalyzed oxidative degradation of quercetin and rutin (quercetin 3-O-rhamnosylglucoside) in aqueous model systems. J. Agric. Food Chem. 48: 3830-3838.

  • Makris DP Rossiter JT (2001) Comparison of quercetin and a non-orthohydroxy flavonol as antioxidants by competing in vitro oxidation reactions. J. Agric. Food Chem. 49: 3370-3377.

  • Makris DP Rossiter JT (2002) Hydroxyl free radical-mediated oxidative degradation of quercetin and morin: a preliminary investigation. J. Food Compos. Anal. 15: 103-113.

  • Medronho B Valente AJ Costa P Romano A (2014) Inclusion complexes of rosmarinic acid and cyclodextrins: stoichiometry association constants and antioxidant potential. Colloid Polymer Sci. 292: 885-894.

  • Mourtzinos I Makris DP Yannakopoulou K Kalogeropoulos N Michali I Karathanos VT (2008) Thermal stability of anthocyanin extract of Hibiscus sabdariffa L. in the presence of β-cyclodextrin. J. Agric. Food Chem. 56: 10303-10310.

  • Nguyen TA Liu B Zhao J Thomas DS Hook JM (2013) An investigation into the supramolecular structure solubility stability and antioxidant activity of rutin/cyclodextrin inclusion complex. Food Chem. 136: 186-192.

  • Osman A Makris DP Kefalas P (2008) Investigation on biocatalytic properties of a peroxidase-active homogenate from onion solid wastes: An insight into quercetin oxidation mechanism. Process Biochem. 43: 861-867.

  • Paleologou I Vasiliou A Grigorakis S Makris DP (2016) Optimisation of a green ultrasound-assisted extraction process for potato peel (Solanum tuberosum) polyphenols using bio-solvents and response surface methodology. Biomass Conver. Bioref. 6: 289-299.

  • Shao P Zhang J Fang Z Sun P (2014) Complexing of chlorogenic acid with β-cyclodextrins: Inclusion effects antioxidative properties and potential application in grape juice. Food Hydrocol. 41: 132-139.

  • Wang Y Gao Y Ding H Liu S Han X Gui J Liu D (2017) Subcritical ethanol extraction of flavonoids from Moringa oleifera leaf and evaluation of antioxidant activity. Food Chem. 218: 152-158.

  • Zenkevich IG Eshchenko AY Makarova SV Vitenberg AG Dobryakov YG Utsal VA (2007) Identification of the products of oxidation of quercetin by air oxygenat ambient temperature. Molecules 12: 654-672.

Search
Journal information
Impact Factor


CiteScore 2018: 0.68

SCImago Journal Rank (SJR) 2018: 0.173
Source Normalized Impact per Paper (SNIP) 2018: 0.288


Cited By
Metrics
All Time Past Year Past 30 Days
Abstract Views 0 0 0
Full Text Views 1107 871 14
PDF Downloads 206 125 29