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1 This is a repository copy of Scalable anthocyanin extraction and purification methods for industrial applications. White Rose Research Online URL for this paper: Version: Accepted Version Conference or Workshop Item: Blackburn, RS orcid.org/ , Farooque, S, Beaumont, N et al. (3 more authors) (2017) Scalable anthocyanin extraction and purification methods for industrial applications. In: 9th International Workshop on Anthocyanins, Feb 2017, Auckland, New Zealand. These are the author's presentation slides of a conference presentation made at the 9th International Workshop on Anthocyanins. Reuse Unless indicated otherwise, fulltext items are protected by copyright with all rights reserved. The copyright exception in section 29 of the Copyright, Designs and Patents Act 1988 allows the making of a single copy solely for the purpose of non-commercial research or private study within the limits of fair dealing. The publisher or other rights-holder may allow further reproduction and re-use of this version - refer to the White Rose Research Online record for this item. Where records identify the publisher as the copyright holder, users can verify any specific terms of use on the publisher s website. Takedown If you consider content in White Rose Research Online to be in breach of UK law, please notify us by ing eprints@whiterose.ac.uk including the URL of the record and the reason for the withdrawal request. eprints@whiterose.ac.uk
2 Keracol Functional, natural, sustainable Scalable anthocyanin extraction and purification methods for industrial applications Richard S. Blackburn, a,b Sannia Farooque, c Nicholas Beaumont, c Meryem Benohoud, b Alenka Tidder, b Christopher M. Rayner b,c a Sustainable Materials Research Group, University of Leeds, UK b Keracol Limited, University of Leeds, UK c School of Chemistry, University of
3 Column n Evaporator Produc t Hot water Compr. air Ethanol (pum ped) Extraction-Purification Skins Skins 3-way Waste 3-way Spray dryer Industrial-scale process Extract from berry waste Fruits are used in juice production Only waste skins are used to produce the extract Sustainably sourced Acidic aqueous extraction of dried skins Concentration using Solid Phase Extraction (SPE) resin removes free sugars and small organic acids Ethanol elution of polyphenols retained by resin
4 BLACKCURRANT (Ribes nigrum) 140 mau WV waste Cy3glc (7.0%) Cy3rut (34.0%) Dp3glc (15.7%) Dp3rut (43.3%) %B: 0.0 % Flow: ml/min ARONIA (Aroniamelanocarpa) 70 #26 [modified by ch PMR 112A/0 Hy mau WV waste Cy3gal (68%) Cy3arab (30%) -20 %B: 0.0 % Flow: ml/min
5 GRAPE (Vitisvinifera) waste Cy3glc (5.8%) Dp3glc (7.3%) Mv3glc (65.3%) Pn3glc (6.0%) Pt3glc (15.6%)
6 Case Study 1: Natural hair dyes ANC extract from blackcurrant waste skins (UK grown) Patented (WO ) semipermanent hair colorants and coloration process Range of shades, fast to 12+ washes Case Study 3: Marking eggshell Inks using ANC extracted from waste (WO ) Increase in the information placed on an egg Reduced environmental and toxicological impact Enhance security, safety, and traceability Case Study 2: Food colorants ANC extracted from sustainable sources Lake pigment formed with metal Pigments in range of colours Both water soluble and water insoluble pigments possible Current research on ANC applications Cosmetic colorants and make-up Food colorants for lipophilic media Coloration of high-value textiles Collaboration with University of Porto
7 K/S Dyeing silk and wool with blackcurrant anthocyanins Range of colours obtainable by modifying ph and mordant metal Good wash fastness (30 C) Poor to medium light fastness SILK ph 2.2 ph 3 ph 4 Aluminium sulphate No metal WOOL ph 2.2 ph 3 ph 4 Aluminium sulphate No metal 3.0 Al sulfate ph 5 ph ph 2.2 ph 3 ph 4 ph 7 ph l (nm) ph 5 ph 7 ph 9 ph 11 ph 9 ph 11 ph 9 ph 11
8 Investigation of the full composition of blackcurrant skin extract post-spe
9 Blackcurrant post-spe extract 1 H NMR 1 H NMR spectrum (from MeOH) of the blackcurrant extract indicated presence of four major anthocyanins Relative ratio of ANCs based on integration values in good agreement with HPLC results characteristic peaks for anthocyanins
10 Anthocyanin-rich extract 40 mau %B: 0.0 % Flow: ml/min
11 Identification of other components FLAVANOLS: HYDROXYCINNAMIC ACIDS:
12 Liquid-liquid partitioning Aim was to purify anthocyanin extract by separating from other polyphenols Method for anthocyanin enrichment had to be scalable and economically viable Liquid-liquid partitioning was considered a good starting point as it can be scaled up relatively easily
13 Liquid-liquid partitioning In acidic conditions, charged AH + anthocyanins have higher solubility in water HO O R 1 OH R 2 However, uncharged flavonoids are expected to be relatively less water soluble OH OGly flavylium cation (AH + ) Sugar moieties should enhance water solubility of neutral polyphenols
14 YIELD (WT. %) Selected solvents: hexane, ethyl acetate, ipropyl acetate and chloroform, partitioning with acidified water (ph 1.8; HCl) ETHYL ACETATE CHLOROFORM IPROPYL ACETATE Hexane Polar solvent Water VERY POLAR COMPONENTS NEUTRAL POLYPHENOLS
15 Liquid-liquid partitioning ethyl acetate ipropyl acetate chloroform
16 Anthocyanins 1 H NMR spectra CHCl 3 Significant ANC EtOAc Some ANC iproac No ANC
17 Sequential liquid-liquid partitioning Extract first partitioned with isopropyl acetate removes quercetin and myricetin algycons and hydroxycinnamic acids Extract then partitioned with ethyl acetate removes quercetin and myricetin glucosides ipropyl acetate ethyl acetate
18 ph-controlled liquid partitioning At ph 6.3: quercetin rutinoside (7.52 ppm) and myricetin rutinoside (7.30 ppm) migrate into EtOAc layer At ph 12.1: quercetin and myricetin rutinosides do not migrate into EtOAc Aqueous layer at ph 6.3 Anthocyanins quercetin-3-rut myricetin-3-rut Aqueous layer at ph 12.1
19 Anthocyanins EtOAc at ph 12 EtOAc at ph 6 EtOAc at ph 1.8
20 Post-SPE extract EtOAc ph 6 ( 1 H NMR in MeOH) Aqueous layer ph 6 ( 1 H NMR in 0.5% TFA + MeOH)
21 Sequential liquid-liquid partitioning with ph changes BC extract comprises 48% ANC and 26% other polyphenols Myricetin and quercetin rutinosides removed with EtOAc at ph 6.3 iproac at ph 1.8 removes hydroxycinnamic acids and myricetin + quercetin aglycons Four ANC remain in aqueous layer (immediately acidified and freeze dried) Trace ANC EtOAc at ph 1.8 selectively removes myricetin + quercetin glucosides
22 ph-controlled liquid partitioning At ph 6.3 myricetin-3-rut + quercetin-3-rut migrate into EtOAc At ph 6.3 neutral ANC anhydrobase (A) should form But Cy-3-rut, Cy-3-glc, Dp-3-rut and Dp-3-glc (A form?) do not migrate into EtOAc Potential of disruption of co-pigmentation? Breaking down interaction between ANC and myricetin/quercetin rutinosides? R 1 R 1 HO O OH R 2 -H + HO O +H + O R 2 OGly OGly OH OH flavylium cation (AH + ) a nhydrobase (A)
23 Conclusions Blackcurrant extract post-spe can be purified using sequential liquid-liquid and ph change extraction Provides an isolate with only four anthocyanins present (clean 1 H NMR evidence) in a process that is industrially scalable Separation enable by relative water solubility of different components in BC extract mixture Further investigation required to determine reasons for EtOAc separation of myricetin-3-rut + quercetin-3-rut from neutral anhydrobase forms of ANC glycosides at ph 6.3
24 Keracol Functional, natural, sustainable
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