Introduction in Functional Components for Membrane Separations

Chapter 2

Introduction in Functional Components for Membrane Separations ˘ s1 and Charis M. Galanakis3,4 Sonia A. Socaci1,2, Anca C. Farca¸ 1

Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania, 2Institute of Life Sciences, University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, Cluj-Napoca, Romania, 3 Department of Research & Innovation, Galanakis Laboratories, Chania, Greece, 4 Food Waste Recovery Group, ISEKI Food Association, Vienna, Austria

Chapter Outline 2.1 Introduction 2.2 Challenges in Functional Food Development 2.3 Recovery of Bioactive Compounds From Conventional and Nonconventional Sources 2.3.1 Proteins and Active Peptides 2.3.2 Polyphenols 2.3.3 Polysaccharides

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2.3.4 Lipids 2.3.5 Bioactive Compounds of Animal Origin 2.4 Separation and Recovery of Macro- and Micromolecules Using Membrane Technologies 2.5 Conclusions References Further Reading

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52 68 68 77

2.1 INTRODUCTION Functional ingredients and foods are constantly gaining importance in the everyday choices of consumers, due to the increasing interest of consumers in promoting and improving their health through diet. This new trend, based on the principle that it is more effective to prevent a disease than to cure it, has motivated the scientific world in increasing efforts toward research focused on identifying, isolating, and purifying bioactive compounds with health-promoting properties that can be used as functional ingredients to fortify foods and beverages (McClement, 2012). Another point of interest is finding new sources of bioactive compounds, optimizing the extraction and Separation of Functional Molecules in Food by Membrane Technology. DOI: https://doi.org/10.1016/B978-0-12-815056-6.00002-4 © 2019 Elsevier Inc. All rights reserved.

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purification methods, as well as maintaining the bioactivity of these compounds throughout the product shelf life. There is no consistent definition of the term “functional food” throughout the world’s countries, the term being constantly revised by regulatory bodies. In Europe, for example, the EU government does not have a formal legislative definition for “functional foods” (Martirosyan and Singh, 2015). A commonly accepted definition by several organizations is that “functional foods” are “foods or ingredients of foods that provide an additional physiological benefit, beyond their basic nutrition” (Day et al., 2009). Recently, the Functional Food Center, USA, defined the term as “natural or processed foods that contains known or unknown biologically-active compounds; the foods, in defined, effective, and nontoxic amounts, provide a clinically proven and documented health benefit for the prevention, management, or treatment of chronic disease” and it is currently trying to standardized this definition (Martirosyan and Singh, 2015). According to the above definitions, the simplest examples of functional foods are fruits and vegetables due to their content in phytochemicals such as polyphenols, carotenoids, dietary fiber, vitamins, fatty acids, minerals, proteins, etc. These bioactive compounds have known beneficial health effects proven by various in vitro or in vivo studies (e.g., antioxidant activity protecting the cells from reactive oxygen species damage and thus lowering the risk of developing different diseases associated with oxidative stress, antimicrobial properties, antiinflammatory, antitumor activity, antihypertensive, antidiabetic) (Ganesan and Xu, 2017; Hasler, 2002; Williamson, 2009). Examples of functional foods may also include foods in which a component was added (e.g., enriched in omega-3 fatty acids) or removed/reduced (e.g., low-fat products, gluten-free) or a food in which one or several components have been modified, replaced, or enhanced to improve its health properties (e.g., yogurt with probiotic bacteria) (Stein and Rodriguez-Cerezo, 2008).

2.2 CHALLENGES IN FUNCTIONAL FOOD DEVELOPMENT Functional foods exist at the interface between food and drugs, and therefore offer great potential for health improvement and prevention of diseases when ingested as part of a balanced diet (Hilliam, 2000; Otles and Cagindi, 2012). The functional properties of the bioactive compounds are proven by extensive scientific research, but to be used in human nutrition, their safety, efficacy, and bioavailability must also be ensured by a regulatory framework to provide clear information to consumer and not misleading claims. In this sense, the benefits versus the risk of long-term intake need a thorough assessment and further investigation. Several aspects have to be considered and characterized: 1. the safety of the intake of these bioactive compounds (with or without nutrient value) related to the long-term consumption of functional foods

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2. the interactions between the bioactive compounds used to fortified the food product and other ingredients 3. the impact of the technological processing of food on the functionality of bioactive compounds The requirements of functional food safety indicated by FAO/WHO impose on manufacturers the obligation to conduct placebo-controlled clinical studies and to evaluate their results in four phases: safety, efficiency, effectiveness, and surveillance (Otles and Cagindi, 2012). Even though the functional food market is growing every year, there is still the need for developing new functional food. The process of developing new functional food is an expensive one, involving technological, legal, and commercial challenges (McClements et al., 2009). Regarding the technological challenges, one has to take into consideration the compatibility between the bioactive compound and food matrix (e.g., solubility, stability) and the processing flow, the development of adequate delivery systems for bioactive compounds. Moreover, the substantial investment of a company in the research required for the functional food to meet the efficacy and safety criteria is not always returned within the company. In other words, after the health claim is adequately documented, other competing companies may use the claim and make profit. Incentives, such as a period of exclusivity or tax incentives, would encourage food companies to pursue functional food development by ensuring a profitable return on successful products (IFT, 2018; Khan et al., 2013). Another opportunity is to find renewable and lowcost sources of high-value compounds. The generation of food waste is inevitable, especially during the preconsumption stage (Ravindran and Jaiswal, 2016). The implementation of strict legislation for human health and environmental safety and the emergence of novel techniques for the recovery of commercially important biomolecules has caused enormous interest in food supply chain waste valorization. Technologies for the recovery of high added value compounds are pivotal to the utilization of food waste for commercial applications. In this conjuncture, the exploitation of food byproducts for the recovery and reuse of valuable bioactive compounds is one of the most sustainable approaches.

2.3 RECOVERY OF BIOACTIVE COMPOUNDS FROM CONVENTIONAL AND NONCONVENTIONAL SOURCES Fruit and vegetable byproducts such as peel, bark, seeds, leaves, etc., often contain more bioactive compounds and with higher antioxidant activities than those found in the edible portion (Can-Cauich et al., 2017). Thereby, more and more research is focused on exploiting these unconventional sources for the recovery of valuable molecules. Use of these byproducts as sources of bioactive compounds usually requires preliminary processing

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steps before the extraction, like reducing the water content or drying in order to minimize the microbiological and biochemical reactions, to increase the concentration in bioactive compounds, to ease the handling, and to extend the storage period. There is no universal method for the extraction of bioactive compounds, but several criteria must be fulfilled for an extraction process to be considered efficient and economically sustainable: selectivity toward the analyte, high extraction yields, possibility of solvent recovery or using “green solvents,” use of low-cost reagents, low energy consumption, reduced extraction time, maintaining the functionality of the recovered molecules, and possibility to be scaled up (Azabou et al., 2016; Tunchaiyaphum et al., 2013; Socaci et al., 2017b). Thereby, the classical solid liquid and liquid liquid extraction methods are being optimized, to overcome the limitations related to the high amount of used solvents, toxicity of the solvents, waste management, etc. Among the currently most employed modern extraction techniques we can mention are microwave-assisted extraction, ultrasound-assisted extraction, pressurized liquid extraction (e.g., pressurized hot water extraction), enzymeassisted extraction, supercritical CO2-based extraction, membrane filtration processes, and other emerging techniques (Angiolillo et al., 2015; Banerjee et al., 2017; Goula et al., 2017; Heng et al., 2017, pp. 25 27; Loginov et al., 2013; Socaci et al., 2017a). Choosing the appropriate extraction method is crucial in the recovery of the bioactive molecules, because it significantly influences the yield and the composition of the extract. Several examples of extraction methods used for the recovery of bioactive compounds from different matrices are presented in Table 2.1.

2.3.1 Proteins and Active Peptides Proteins and peptides include a group of macromolecules that consists of amino acids of polymeric chains of amino acids. They are known to possess a variety of nutritional, functional, and biological properties. Nutritionally, the proteins are a source of energy and amino acids, which are essential for growth and maintenance. Functionally, the proteins contribute to the physicochemical and sensory properties of various protein-rich foods. For example, when incorporated in food products, protein may exert emulsifying properties, film forming properties, flavor binding capacity, viscosity increase by binding the water, and gelation properties (Aydemir et al., 2014; Sharma et al., 2010; Socaci et al., 2017a; Yu et al., 2016). Proteins are used in the food industry as fat replacement in meat and milk products, flavor enhancers in confectionery, and food and beverage stabilizers (Patsioura et al., 2011). Furthermore, many dietary proteins possess specific biological properties that make these components potential ingredients of functional or healthpromoting foods. The majority of the functional properties of proteins are attributed to physiologically active peptides encrypted in protein molecules

TABLE 2.1 Examples of Bioactive Compounds From Plant and Animal-Derived Products or Waste and the Employed Extraction Techniques Compound Class

Waste Origin

Byproduct Source

Extraction Techniques

References

Proteins and bioactive peptides

Cereals

Brewer’s spent grain

Ultrasonic-assisted extraction

Tang et al. (2010)

Sequential extraction of proteins and arabinoxylans

Vieira et al. (2014)

Enzymatic assisted extraction

Niemi et al. (2013)

Ultrafiltration

Tang et al. (2009)

Defatted rice bran

Alkali extraction and isoelectric precipitation

Han et al. (2015)

Rice byproducts

Enzymatic hydrolysis and membrane filtration technique

Ferry et al. (2017)

Soybean

Subcritical water hydrolysis

Pinkowska and Oliveros (2014)

Rapeseed meal

Ultrasound-assisted aqueous extraction

Yu et al. (2016)

Subcritical water hydrolysis

Pinkowska et al. (2013)

Sunflower meal

Alkaline solubilization and acid precipitation

Salgado et al. (2012)

Hazelnut meal

Solvent extraction (water, acetone)

Aydemir et al. (2014)

Flaxseed hull

Coagulation and ultrafiltration

Loginov et al. (2013)

Oil crops

(Continued )

TABLE 2.1 (Continued) Compound Class

Waste Origin

Byproduct Source

Extraction Techniques

References

Canola meal

Alkaline solubilization and acid precipitation (isoelectric precipitation)

Manamperi et al. (2011) Karaca et al. (2011)

Fruits and vegetable

Animal byproducts

Electroactivated solutions (noninvasive extraction method)

Gerzhova et al. (2015)

Salt precipitation

Karaca et al. (2011)

Palm kernel cake

Enzymatic hydrolysis

Ng et al. (2013)

Defatted cherry seeds

Enzymatic hydrolysis and membrane ultrafiltration

Garcia et al. (2015)

Apricot kernel cake

Alkaline solubilization and acid precipitation

Sharma et al. (2010)

Spirulina

Enzymatic hydrolysis and membrane filtration

Ma et al. (2007)

Fish and chicken

Isoelectric solubilization/precipitation

Shi et al. (2017)

Chicken feathers

Enzymatic hydrolysis and membrane ultrafiltration

Fontoura et al. (2014)

Whey

Ion exchange chromatography/cationexchange selective adsorption process

El-Sayed and Chase (2010a,b)

Membrane filtration techniques

Ndiaye et al. (2010)

Egg yolk

Ultrafiltration, gel filtration and reversedphase HPLC

Pokora et al. (2014)

Shellfish

Enzymatic hydrolysis and micro-, ultra-, and nanofiltration, ion exchange chromatography

Beaulieu et al. (2013)

Polysaccharides

Cereals

Fruits and vegetables

Brewer’s spent grain

Enzymatic hydrolysis

Niemi et al. (2012a,b)

Sequential extraction of proteins and arabinoxylans

Vieira et al. (2014)

Acid hydrolysis

Mussatto and Roberto (2005)

Defatted flaxseed Rice bran Sesame husk

Enzymatic hydrolysis

Nandi and Ghosh (2015)

Citrus peel and apple pomace

Subcritical water extraction

Wang et al. (2014)

Orange peel

Ultrahigh pressure/microwave

Guo et al. (2012)

Microwave extraction

Maran et al. (2013)

Microwave

Seixas et al. (2014)

Passion fruit Pomelo

Quoc et al. (2015)

Pumpkin kernel cake and oilpumpkin biomass

Sequential extraction

Koˇsta´lova´ et al. (2013)

Berry, bilberry, and black currant press cake from juice production

Aqueous extraction, sequential buffer extraction and ultrafiltration

Mu¨ller-Maatsch et al. (2016) Hilz et al. (2005)

Mandarin peel

Crossflow microfiltration

Cho et al. (2003)

Olive mill wastewaters

Ultrafiltration

Galanakis et al. (2010) (Continued )

TABLE 2.1 (Continued) Compound Class

Waste Origin

Byproduct Source

Extraction Techniques

References

Lipids, fatty acids

Cereals

Brewer’s spent grain

Soxhlet extraction

Niemi et al. (2012b)

Rice bran

Solid liquid extraction supercritical fluid to the extraction

Oliveira et al. (2012) Perretti et al. (2003)

Fruit and vegetables

Animal byproducts

Grape seeds

Pressurized carbon dioxide extraction with compressed carbon dioxide as solvent and ethanol as cosolvent

Dalmolin et al. (2010)

Supercritical fluid extraction

Prado et al. (2012)

Microalgae

Cell disruption method

Oviyaasri et al. (2017)

Byproducts from the palm oil extraction

Separation techniques through membranes

Tan et al. (2007)

Fish and chicken

Isoelectric solubilization/precipitation

Shi et al. (2017)

Fish

Supercritical fluid extraction

Sarker et al. (2012) Ferdosh et al. (2015)

Polyphenols

Cereals

Brewer’s spent grain

Alkaline hydrolysis

Mussatto et al. (2007)

Rice bran biomass (byproduct)

Subcritical water extraction

Pourali et al. (2010)

Roasted wheat germ (byproduct)

Supercritical fluids CO2

Gelmez et al. (2009)

Oil crops

Fruits and vegetables

Rapeseed

Ultrasound-assisted aqueous extraction

Yu et al. (2016)

Byproducts from the palm oil extraction

Separation techniques through membranes

Tan et al. (2007)

Olive byproducts

Continuous countercurrent liquid liquid extraction

Allouche et al. (2004)

Chemical (acid) hydrolysis

Bouallagui et al. (2011)

Sunflower meal

Mild-acidic protein extraction with adsorptive removal of phenolic compounds

Weisz et al. (2013)

Flaxseed hull

Coagulation and ultrafiltration

Loginov et al. (2013)

Tomato pomace and skin

Enzymatic assisted extraction/solvent extraction

Azabou et al. (2016)

Potato peels and tubers

Pressurized liquid extractor

Luthria (2012)

Solvent extraction (stirring)

Ieri et al. (2011)

Ultrasound extraction

Singhai et al. (2011)

Purple sweet potatoes

Ultrasound-assisted extraction, centrifugation and ultrafiltration

Zhu et al. (2016)

Orange peels

Nanofiltration

Conidi et al. (2012)

Bergamot juice

Ultrafiltration, nanofiltration

Conidi et al. (2011)

Artichoke wastewater

Membrane filtration (ultrafiltration, nanofiltration) and polymeric resins

Conidi et al. (2015) (Continued )

TABLE 2.1 (Continued) Compound Class

Waste Origin

Byproduct Source

Extraction Techniques

References

Onion skin (byproduct)

Subcritical water

Ko et al. (2011)

Forest fruit pomaces

Supercritical fluid extraction

Laroze et al. (2010)

Peanut skins byproduct

Microwave

Ballard et al. (2010)

Apple pomace

Ultrasound extraction

Pingret et al. (2012)

Apple and peach pomaces

Subcritical water

Adil et al. (2007)

Grape seeds

Supercritical fluid extraction

Agostini et al. (2012) Yilmaz et al. (2010)

Carotenoids

Essential oils

Fruits and vegetables

Fruit and vegetables

Concentration and ultrafiltration

Nawaz et al. (2006)

Enzymatic assisted extraction

Azabou et al. (2016)

Supercritical fluids CO2

Yi et al. (2009)

Citrus peel

Ultrasound extraction

Sun et al. (2011)

Sea buckthorn seeds

Supercritical carbon dioxide fluid extraction

Kagliwal et al. (2011)

Citrus peel

Solvent extraction, distillation, hydrodistillation

Thongnuanchan and Benjakul (2014)

Tomato pomace and skin

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(Roupas et al., 2007). Depending on the source, the molecular weight (MW) of proteins ranges from decades to hundreds of kDa. Proteins may also have different charges because amino acids are amphoteric and the charge of their molecule depends on its isoelectric point. For example, oat contains mainly globulin (20 35 kDa and pI 5 5.5), albumin (14 17 kDa, 4.0 , pI , 7.0), and prolamin (17 34 kDa, 5.0 , pI , 9.0) (Klose and Arendt, 2012). These characteristics are used for their selective fractionation during membrane processing. Peptides can show enhanced bioactivities and different functional properties to those reported for the parent protein. Structurally, peptides are short-chain peptide segments of protein molecules, including 2 20 amino acid residues. Their biological activities (e.g., antioxidant, opioid or mineralbinding, immunomodulatory, antimicrobial, hypocholesterolemic, antihypertensive, antithrombotic, antidiabetic) are tailored by their molecular weights and amino acid sequences (Atef and Ojagh, 2017; Kadam et al., 2015; Lemes et al., 2016). Thus, the antimicrobial peptides usually have a molecular weight below 10 kD, and contain up to 50 amino acids, about half being hydrophobic (Atef and Ojagh, 2017). Besides, antioxidant activity has been proved to increase when small peptides are obtained (Moure et al., 2006). Based on these properties, peptides and amino acids recovered by means of subcritical water hydrolysis can be of interest for nutraceutical products, the food industry (e.g., food additives), pet food, or managing patients unable to digest proteins (Marcet et al., 2016). Most bioactive peptides are derived from expensive protein matrices, which in most cases make their application unfeasible. Hence the proteinrich waste generated by agroindustries has become an attractive alternative for protein recovery and reuse (Lemes et al., 2016). But, in order for a byproduct to be considered as a source of protein, it has to fulfill two essential criteria: a high protein content and a high-quality protein (well-balanced essential amino acid composition and bioavailability) (WHO, 2007). The advances made in the isolation and purification technologies led to an increased acceptance of recovered soy proteins from byproducts as functional ingredients in foods. This growing acceptance is also attributed to the nutritional and potential health benefits of the recovered proteins, such as the prevention of hypercholesterolemia, atherosclerosis, and cancer (Yadav and Joyner, 2014). The main byproducts with a relatively high content of protein are the defatted meals resulting from oil production, including olive, palm, sunflower, rapeseed, but also soybean meal, rice bran, cereal spent grain, and microalgae, these biomasses being also available in large quantities and at a low cost. Rice byproducts have been suggested as a cheap, renewable, and abundant source of antioxidant compounds and bioactive peptides. In a recent study, a protein byproduct from the rice starch industry was hydrolyzed with

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five commercial proteolytic enzymes, avoiding the use of solvents or chemicals. The liquid supernatants of the scaled-up digestions were subfractionated by crossflow membrane filtration to isolate peptide samples having different molecular weight ranges. Isolated peptide fractions were demonstrated to possess antioxidant, antihypertensive, antityrosinase and/or antiinflammatory activities, while all were shown to be neither cytotoxic nor irritant (Ferry et al., 2017). A highly attractive waste for the production of bioactive peptides is the one resulting from olive oil manufacturing, considering that from 100 kg of fresh olives around 2 kg of flour with approximately 22% protein is generated in the process (Rodriguez et al., 2008). In another study peptide extracts were obtained by the digestion of the cherry seed protein isolate with alcalase and thermolysin. The results showed that fractions obtained by ultrafiltration possess relative high antioxidant and antihypertensive properties (Garcia et al., 2015). Application of ultrafiltration on recovery of protein from brewer’s spent grain waste water was studied by Tang et al. (2009). More than 92% of the protein was retained by membranes with both molecular weight cutoff (MWCO) of 5 and 30 kDa, the protein contents in the final product being 20.09% and 15.98%, respectively, compared with that of 4.86% concentrated by rotary evaporation (Tang et al., 2009).

2.3.2 Polyphenols Polyphenols are plant secondary metabolites, containing more than one phenol unit or building block per molecule. They are mostly found in fruits, vegetables, cereals, tea, coffee, cacao, etc., but also in the derived foods and in the byproducts resulting after the processing of the raw materials. Beside the fact that polyphenols influence the sensorial attributes of plants and foods (e.g., aroma, taste, astringency, and color), they are also among the most active natural antioxidants (Landete, 2012). There are over 8000 polyphenolic compounds identified in nature (Ganesan and Xu, 2017; Landete, 2012). Polyphenols present in plants are usually conjugated to sugars and organic acids and can be divided in two big groups: flavonoid and nonflavonoid phenolics (Landete, 2012). But, depending on the number of phenolic groups and structural elements, they can be further classified in four classes: G

Flavonoids—including flavones, flavonols, flavanones, flavanols, anthocyanidins, and isoflavonoids, constitute the most important class, with over 5000 compounds being currently described (Lima et al., 2014). They are found in fruits and vegetables, green tea, red wine, etc. Flavonoids include phenolic alcohols (i.e., flavan-3-ols), flavonols, flavones, anthocyanins, and secoiridoids. Phenolic alcohols such as tyrosol

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G

G

G

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and aldehydes such as isovanillic acid are present in grapes and olives, having a low MW (MW 5 110 228) similar to nonflavonoids. Flavonols, like procyanidin B2, quercetin, and kaempferol, are larger molecules (MW 5 286 579), while flavones (e.g., apigenin) have similar characteristics to flavonols. Anthocyanidins (e.g., malvidin, cyanidin-3-glucoside, rutin) are mainly comprised of malvidin 3-glucoside and respective pyruvic acid derivatives as well as pigments of anthocyanins linked either to a catechin unit or to a procyanidin dimer or to a 4-vinylphenol group. The MW of anthocyanidins and their structural characteristics varies importantly depending on their degree of polymerization, for example, starting from simple dimeric acetaldehyde malvidin 3-glucoside structures and reaching heavier fractions (Galanakis, 2015a). Stilbens—belong to a relatively small group of nonflavonoid class of phenolic compounds. The main representative compound is trans-resveratrol. Major dietary sources include grapes, wine, soy, peanuts (Ozcan et al., 2014). Lignans—also a nonflavonoid group of phenolic compounds, these are found in seeds, cereals, legumes, and algae. Phenolic acids—including hydroxybenzoic acids (e.g., gallic acid), hydroxycinnamic acids (e.g., ferulic acid, chlorogenic acid), and their derivatives are the most common nonflavonoid naturally occurring phenolics. They are widespread in the plant kingdom, with appreciable amounts being found in fruits, tea, coffee, vegetables, etc. Other nonflavonoid phenolics include o-diphenols like hydroxytyrosol, gallic, and protocatechuic acids. All these compounds possess low MW (148 194) due to the appearance of only one aromatic ring. Indeed, o-diphenols (i.e., gallic and caffeic acid) are generally smaller and have more polar molecules than the rest hydroxycinnamic acid derivatives (Galanakis et al., 2013).

The polyphenols can also be divided in extractable and nonextractable compounds. Extractable polyphenols are low- and mediummolecular mass phenolics, they can be extracted from the plant matrix using different solvents (water, methanol, aqueous acetone, etc.), and are potentially bioavailable in the small intestine. On the other hand, the nonextractable polyphenols are macromolecular compounds (polymeric polyphenols) or single phenols bound to dietary fiber or protein, which remain insoluble in the usual aqueous-organic solvent and an additional treatment should be applied for their release from the matrix (e.g., acidic hydrolysis, thiolysis). Nonextractable polyphenols are bioavailable only in the large intestine and, as the soluble ones, have remarkable antioxidant activity (Kristl et al., 2011; Landete, 2012; Matthews et al., 1997; Perez-Jimenez and Calixto Saura, 2015). The great scientific interest in polyphenols is mainly due to their functionality as free radical scavengers, but other biological activities (e.g.,

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antiinflammatory, vasodilating, etc.) may be also assigned to these compounds. Depending on the quantity ingested and on their bioavailability in the human body, polyphenols could have desired health effects but also adverse ones (Landete, 2012). Thus, an adequate daily intake of polyphenols, or food containing polyphenols, may improve the protection of the human body against several chronic diseases such as cancers, cardiovascular diseases, cerebrovascular diseases, diabetes, aging and neurodegenerative diseases, and diabetes mellitus (Ganesan and Xu, 2017; Vladimir-Kneˇzevi´c et al., 2012; Landete, 2012; Lima et al., 2014; Ozcan et al., 2014). There is no accurate data available in the literature regarding polyphenol dietary intake. Different attempts were made in establishing a total daily polyphenol intake, but this estimation is difficult not only due to the large extent of dietary habits and preferences, but also due to the structural diversity of polyphenols, their uneven distribution in plant tissues, and their fractioning during processing of raw materials. Scalbert and Williamson (2000), estimated that the daily intake of polyphenols could reach up to 1 g/day. This value is higher than for the rest of the ingested phytochemicals (B10 times higher than the intake of vitamin C and 100 times higher than the intakes of vitamin E and carotenoids) (Scalbert et al., 2005). Another aspect that should be considered is that in most studies, when evaluating the polyphenol dietary intake, the contribution of the nonextractable fraction was ignored. A recent study conducted by Perez-Jimenez and Calixto Saura (2015), focused on determined macromolecular polyphenol (including hydrolyzable and nonextractable proanthocyanidins) content from different fruits and vegetables consumed in four European countries (France, Germany, Spain, the Netherlands) in order to estimate the macromolecular polyphenol intake from food and vegetables. The results showed that the daily intake of this type of polyphenols, in all four European countries taken into study, was about 200 mg. Therefore, it is fair to say that the macromolecular polyphenols are a major part of the total polyphenol content and total antioxidant capacity of fruits and vegetables. Depending on the class of polyphenolic compounds, the extraction process can be achieved by different techniques but all involve the dissolution of compounds at the cellular level in the plant matrix followed by their diffusion in the extraction solvent. Nowadays there is an emphasis on developing or optimizing “eco-friendly” extraction processes in order to minimize the negative impact on the environment and also to obtain functional compounds that do not pose safety issues when used in foods. Membrane processing is one method that reduces the use of toxic organic solvents and concentrates the final product. The main advantages of membrane filtration, compared to the classical extraction procedures, are high purity (clarification, purification, and concentration), reduced energy consumption, higher separation efficiency, milder extraction conditions, and possibility to scale up (Nawaz et al., 2006). Furthermore, membrane filtration is suitable for the recovery of

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bioactive molecules, including polyphenols, from agrifood byproducts (Loginov et al., 2013; Nawaz et al., 2006). A membrane processing method that can be used with success in the separation of polyphenols is ultrafiltration because it can reject compounds with molecular weight higher than 1000 (Nawaz et al., 2006). Many studies were performed in recent years and promising results were obtained for the recovery of polyphenols from different plant materials (e.g., sweet potatoes, bergamot juice) or food waste (e.g., grape seeds, flaxseed hull, artichoke wastewater, citrus byproducts) (Conidi et al., 2011, 2012, 2015; Loginov et al., 2013; Zhu et al., 2016).

2.3.3 Polysaccharides Polysaccharides, which are classified as carbohydrates, are long-chain molecules made up of simple sugar molecules connected by glycosidic linkages. In nature, there is a wide diversity of polysaccharide molecular structures, with different functional properties. The polysaccharides are commonly categorized as starche polysaccharides (SPs) and nonstarch polysaccharides (NSPs); the latter can be further divided in soluble and insoluble fiber (Goh et al., 2014). Demonstration of the beneficial implications of fiber-rich foods on human health has led to their integration in the category of functional ingredients. Soluble dietary fibers reduce the intestinal absorption of blood cholesterol whereas insoluble dietary fibers are associated to water absorption and intestinal regulation apart from the well-known prebiotic and health benefits (Zhu et al., 2015). Consequently, many studies are still ongoing in order to develop nutraceutical and fiber-rich products (Han et al., 2017). NSPs play a crucial role in the food systems in which they are present because they have the ability to control the mobility of free water or to form a three-dimensional network structure in foods. In addition, NSPs’ fraction is capable to create links with other components that exist in the food matrix thus influencing the structure, physical functionality, sensory attributes, and nutritional value of the foods (Goh et al., 2014; Venzon et al., 2015). It is a known fact that the rate at which a product with high starch content is digested can affect the blood glucose level, thus creating major implications for human health. The introduction of NSPs into starch-rich foods can have a positive influence on the reduction of blood glucose levels (Chiu et al., 2011). According to their composition, the pectic polysaccharides recovered from fruit and vegetable byproducts can be used both as food additives due to their physical properties and also as functional foods for their bioavailability and bioactivity in the human body (Mu¨ller-Maatsch et al., 2016). In terms of chemical structure, pectin consists of D-galacturonic acid polymeric units and there are two dominant types in bioresources: homo- and rhamnogalacturonans. The first polymer consists of a backbone of α-1,4-linked

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Separation of Functional Molecules in Food by Membrane Technology

galacturonic acid residues. Homogalacturonan molecules are surrounded by numerous hydroxyl groups that provide the ability to form hydrogen bonds, whereas these molecules are negatively charged due to the demethylation of carboxylic groups. The rhamnogalacturonan backbone contains fewer carboxylic groups compared to the homogalacturonan structure since it is composed of repeated α-L-rhamnose-(1-4)-α-D-galacturonic acid units (Galanakis, 2015a). Pectin molecules are also classified into two groups, high methoxyl pectin and low methoxyl pectin, depending on the degree of esterification (Quoc et al., 2015). The latest affects importantly their technological applications and especially their gelling properties. β-Glucans (soluble dietary fiber with advanced gelling properties, too) are linear homopolysaccharides composed of continuant (1,4)-linked β-D-glucose segments. The latest are separated by single (1,3) linkages. β-Glucan is water soluble due to the presence of the β-(1,3)-linked β-glycosyl residue, which prevents alignment of glucose segments and increases the corresponding solubility (Lazaridou and Biliaderis, 2007). Currently, apple pomace, citrus peels, and to some extent sugar beet pulp are used as sources for commercial pectin production (Di Donato et al., 2014; Poli et al., 2011). These pectic compounds are not only present in high amounts in citrus peels but have also important functionality due to the presence of associated bioactive compounds. Thus, the press cake, beside cell walls polysaccharides, contains B70% of polyphenols originally present in the raw materials (Hilz et al., 2005). Many studies have highlighted that defatted oil bearing materials (such as sesame husk, rice bran, and flaxseed) give interesting health benefits. Compositional analysis reveals that sesame husk, rice bran, and flaxseed consist of almost 68%, 27%, and 39% dietary fiber respectively and have been reported to have positive health effects (e.g., laxative, cholesterol-lowering agent). An added value of the polysaccharides extracted from sesame husk, rice bran, flax seed, or even oilpumpkin biomass is the high antioxidant activity, which makes them suitable functional ingredients to be considered for the development of new dietary supplements and functional foods (Koˇsta´lova´ et al., 2013; Nandi and Ghosh, 2015; Nosa´lova´, et al., 2011). Moreover, the pectic polysaccharide fractions extracted from pea pods were rich in uronic acid (70% 95%); highly methylated (30%) and acetylated (10%); and rich in arabinose, xylose, and galactose, demonstrating a high purity and strong methylation degree (Mu¨ller-Maatsch et al., 2016). The heterogeneity of the pectin structure depends on the plant origin, the part of the plant where it is located (peels, pulp, seed, etc.), and how it is extracted. Nevertheless, the data obtained in the study conducted by Mu¨llerMaatsch et al. (2016), on 26 vegetable wastes, showed that the structure of the pectin extracted from waste is similar to that from the raw matrices, although the methylation and acetylation degrees are lower due to the processing and/or enzymatic actions.

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47

There are several classical ways to extract pectin from different materials, all of them using traditional heating. The physicochemical process involves hydrolysis and extraction of pectin macromolecules from plant tissue, purification of the liquid extract, and isolation of the extracted pectin from the liquid, steps that are influenced by various factors, mainly temperature, pH, and time. In order to obtain better yields and desired functionality, the isolation, purification, and characterization techniques need to be progressively improved. Compared with the conventional methods, microwave extraction proves to be more efficient in terms of extraction yields and time and solvent consumption (Seixas et al., 2014; Quoc et al., 2015). Also, subcritical water extraction method, used for citrus and apple pectin extraction, has proved to be effective, generating a good yield (22% and 17%, respectively). In addition, the extracted pectin showed a high antioxidative and antitumor activity (Wang et al., 2014). In another study ultrahigh-pressure extraction, as an emerging novel technology, was applied to extract pectin from orange peel. The obtained results demonstrated that ultrahigh-pressure was an efficient, timesaving, and ecofriendly method, the extraction yield and stability being significantly higher than those of traditional heating and microwave extraction (Guo et al., 2012). The ultrafiltration technology can be employed to purify pectin extracted from fruit byproducts and β-glucan recovered from cereal byproducts (Patsioura et al., 2011; Galanakis et al., 2013). Like in the case of proteins, the MW of both pectin and β-glucan moieties also ranges from decades to hundreds of kDa. The large size of these molecules restricts their permeation through small pores, while the surrounding hydroxyl groups form hydrogen bonds with the water and hydrophilic membranes (Galanakis, 2015a). Qiu et al. (2009) used five types of ultrafiltration membranes with different molecular weight cutoffs to separate apple pectin with different molecular weights. The results showed that galacturonic acid contents and esterification degrees increase with an increase in molecular weight as well as the monosaccharide composition (Qiu et al., 2009). The efficiency of membrane filtration processes was highlighted also in the case of pectin isolated from an extract prepared from mature citrus peel: the use of a crossflow microfiltration (MW) step contributed to a 75% saving in the solvent consumption, and although the pectin recovery yield decreased from 10.5% to 9.9 %, the galacturonic acid content increased from 68.0% to 72.2% (Li and Chase, 2010). In addition, by ultrafiltration, the pigments and impurities can be removed due to the absorptive function. The soluble pigments in the sunflower head are strongly associated with the pectin extract and brought undesired color to the final products. In this regard, by purifying the extracted pectin by the ultrafiltration process, approximately 50% of pigments and 75% of salts have been removed (Kang et al., 2015).

48

Separation of Functional Molecules in Food by Membrane Technology

Brewer’s spent grain, the main waste from the beer production process, is another valuable source of carbohydrates, their level being up to 50% of the byproduct weight. The main carbohydrates in brewer’s spent grain are cellulose (B17% dw) and hemicelluloses, mainly arabinoxylan (25 28% dw) (Niemi et al., 2012a; Vieira et al., 2014). The easiest way to exploit brewer’s spent grain as a functional ingredient involves drying and converting it into flour. Thus, by adding brewer’s spent grain flour to various food products (e.g., bakery products, extruded products, and meat products) an improvement in their fiber, protein, mineral content, and water holding capacity can be achieved (Farcas et al, 2017; Nagy et al., 2017; Stojceska et al., 2008). Being a material rich in hemicelluloses, brewer’s spent grain can be subjected to various hydrolysis processes in order to release the monosaccharides (xylose and arabinose), which can be further fermented in order to generate valuable products (e.g., xylitol, a sweetener used in food industry) (Mussatto and Roberto, 2005). Also, arabinoxylans, which are considered a dietary fiber with many potential applications as functional ingredients, can be extracted from brewer’s spent grain under strong alkaline conditions and also by using an innovative fully integrated process that sequentially extracts the proteins and arabinoxylans (Vieira et al., 2014).

2.3.4 Lipids Most fresh fruits and vegetables exhibit a low content of fat; in contrast, dry vegetables and many fruit seeds and kernels contain large amounts of (often discarded) high-value oils that are potentially useful for incorporation in functional foods, cosmetics, and pharmaceutical products (Femenia, 2007). Polyunsaturated fatty acids (PUFAs) and phospholipids as well as the lipid-soluble minor components such as carotenoids, tocopherols, and phytosterols have become the focus of lipid-based nutraceutical products. The main source of PUFA is fish oils whereas the main source of phospholipids, carotenoids, tocopherols, and phytosterols is vegetable oils and other plant materials (Akin et al., 2012) According to the World Health Organization (WHO, 2010), saturated fatty acid consumption, mainly myristic and palmitic acids, is directly related to the risk of cardiovascular diseases. Therefore, diets should provide an adequate supply of polyunsaturated fatty acids and oleic acid. Rice bran, a low-value coproduct obtained from rice processing, could represent a potential source of healthy products due to the unique antioxidant and nutraceutical complex present in its composition (Oliveira et al., 2012). Rice bran contains almost 12% 18.5% oil, with a well-balanced fatty acid profile in terms of unsaturated-to-saturated fatty acids ratio and the ratio of diunsaturated (linoleic acid) to saturated (palmitic acid) and monounsaturated (oleic acid) fatty acids. Rice bran contains a range of fats, of which 47% are monounsaturated, 33% polyunsaturated, and 20% saturated. Also, it

Introduction in Functional Components Chapter | 2

49

comprises around 4.3% highly unsaponifiable components like tocotrienols (a form of vitamin E), gamma oryzanol, and betasitosterol (Marcet et al., 2016). Tocols have proven effectiveness in preventing cardiovascular disease and some forms of cancer, whereas oryzanol, a mixture of triterpene alcohols and phytosterols esterified with ferulic acid, has shown hypocholesterolemic activity being effective in decreasing early atherosclerosis (Pal and Pratap, 2017). By using ethanol as extraction solvent, it was possible to obtain values from 123 to 271 mg of tocols/kg of fresh rice bran and 1527 to 4164 mg of oryzanol/kg of fresh rice bran, indicating that it is feasible to obtain enriched oil when the proper solvent is used (Oliveira et al., 2012). Many marine microalgae strains have oil contents of between 10% and 50% (w/w) and produce a high percentage of total lipids (up to 30% 70% of dry weight). They contain a considerable amount of high-quality oils, partly consisting of omega-3 and omega-6 fatty acids, which can be used as bioactive ingredients in the development of functional foods. Long-chain polyunsaturated fatty acids (LC-PUFAs) such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) are considered essential omega-3 fatty acids in human nutrition, microalgae being considered a valuable vegetal source for the extraction of these compounds. Microalgae, and supplements derived from it, are excellent alternative sources of EPA, DHA, and other fatty acids, since fish often contain toxins due to pollution (Oviyaasri et al., 2017). Research underway in the palm oil industry has revealed a range of bioactives that can be used as functional components for food products that enhance health. Palm pressed fibers contain extractable phytochemicals such as sterols, vitamin E, carotenoids, phospholipids, squalene, and phenolics that are earmarked for applications in functional foods, nutraceuticals, pharmaceuticals, and the cosmetics industry. Although oil is the primary product from the palm, various byproducts are generated during the extraction (Tan et al., 2007).

2.3.5 Bioactive Compounds of Animal Origin Meat and meat products represent an important segment of the human diet because they provide essential nutrients that cannot be easily obtained from vegetables and their derived products. Over the last decade, the amount of byproducts generated from the animal products industry has continued to witness tremendous growth. These byproducts, which are usually perceived as waste, can in fact be further reprocessed for extraction of valuable bioactive compounds (Alao et al., 2017). The major sources of animal waste are represented by the meat, fish, and poultry industries, this material including slaughterhouse derivatives that cannot be sold, such as organs and other visceral mass, feathers, heads,

50

Separation of Functional Molecules in Food by Membrane Technology

bones, fat and meat trimmings, blood and other fluids, wastes from seafood, skins, and wastes from dairy processing such as curd, whey, and milk sludge from the separation process (Bordenave et al., 2002; Durham and Hourigan, 2007). Meat byproducts are rich in lipids, carbohydrates, and proteins and can be subjected to different processes in order to recover nutrients (Shi et al., 2017). In addition, bioactive peptides can be created from meat proteins using different types of hydrolysis and purification procedures. These bioactive compounds are known to have antimicrobial, antioxidative, antithrombotic, antihypertensive, anticarcinogenic, satiety regulating, and immunomodulatory activities and may affect the cardiovascular, immune, nervous, and digestive systems. Peptides may also be effective in the treatment of mental health diseases, cancer, diabetes, and obesity (Helkar et al., 2016; Lafarga and Teagase, 2014; Marcet et al., 2016). Animal blood is a byproduct from meat processing and contains a high level of protein and iron that can be reclaimed and reused. Also, the plasma protein HEC complex was reported to contain a large amount of essential amino acids and electrophoretic separation of plasma protein resulted in complex albumin forming the major fraction (Wan et al., 2002). The recovery of protein from red cells of bovine blood by ultrafiltration indicated that the obtained fraction had a good amino acid profile for use as an ingredient in formulated foods for human consumption (Roupas et al., 2007). Collagen is another component that can have nutraceutical and biomedical applications since microporous collagen films are used for delivery of anticancer drugs and collagen matrices are used as gene delivery agents that promote bone and cartilage formation. Also, gelatin is found to be a potent antioxidant and antihypertensive and to enhance dietary calcium absorption. Today there is an increasing demand for functional molecules, which promotes fish raw materials and utilization of the byproducts as raw materials for food, nutraceutical, pharmaceutical, and biotechnological applications. The fish industry is one of the most problematic food industries, since around a 40% 50% of total weight of the animal is considered to be waste (Kaspar and Reichert, 2013). The popularity of fish oil dietary supplements has been steadily growing due to their high content of omega-3 polyunsaturated fatty acids (ω-3 PUFAs) such as eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) (Rizliya and Mendis, 2014; Shi et al., 2017). The modern diet is insufficient in omega fatty acids, hence the intake of oily fish two to three times a week is recommended. Incorporation of fish oils into normal food ingredients can be considered as an alternative in order to increase the intake of polyunsaturated fatty acids, especially EPA and DHA. Nutritionally, EPA and DHA are the most important components of the omega-3 fatty acids family, as they have significant human health benefits. There is already plenty of scientific evidence proving that these compounds have a positive impact on human health by reducing the risk of

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51

cardiovascular disease, cancer, diabetes, and depression, as well as improving the immune system, and ensuring proper neural development (Oviyaasri et al., 2017). The food products fortified with ω-3 PUFAs provide a way to achieve desired biochemical effects of these nutrients without the ingestion of dietary supplements, medications, or a major change in dietary habits. Also, the isoelectric solubilization/precipitation (ISP) allows efficient recovery of fish protein isolate that could be used in functional foods. Based on proximate composition, high protein recovery yield and high reduction of lipid in the recovered protein indicate that ISP processing effectively recovers nutrients from various representative species (Tahergorabi et al., 2012). Carnivorous fishes’ stomachs have a high pepsin content that can be separated by ultrafiltration, concentration, and spray-drying. Fish skin and bones are also potential sources of collagen and gelatin. Collagen is obtained by acid treatment of the byproducts whereas gelatin is derived from fish skin by enzymatic hydrolysis (Gildberg, 2004). The byproducts generated by the fish industry can also be exploited as sources of bioactives. The fish frame resulting after the filleting of fishes is a complete source of protein because it contains appreciable levels of muscle protein with essential amino acids. Moreover, the fish protein isolate can be used for the isolation of bioactive peptides, which have manifold applications in functional foods and pharmaceutical products due to their antihypertensive or angiotensin-converting enzyme (ACE) inhibition, antiproliferative, anticoagulant, immunomodulatory, and chelating effects (Atef and Ojagh, 2017). Another source of animal-derived food waste is the dairy industry. Whey, the principal byproduct from dairy processing, contains 95% of the original water, most of the lactose, 20% of the milk protein, and traces of fat (Russ and Meyer-Pittroff, 2004). The problem with whey utilization is that a very large volume of whey is produced worldwide each year and it contains only dilute concentrations of these valuable proteins and other biochemicals (Ravindran and Jaiswal, 2016). Recently, methods based on membrane technologies have been developed for the treatment of wastewater and aqueous food systems (Castro-Munoz et al., 2015). An example is the ultrafiltration of milk for cheese manufacture, which increases the recovery of whey proteins in the cheese and reduces whey volumes (Durham and Hourigan, 2007). It was found that column chromatography and membrane separation remain the most commonly used techniques for whey protein fractionation. Better results, particularly in terms of purity levels, were obtained with the coupling approach involving a combination of more than one technique (El-Sayed and Chase, 2011). The whey fractionation process and ultrafiltration of permeate impose greater processing demands, but result in a wide range of products with unique functionalities and high value. Fractionated whey products include whey protein concentrate; whey protein isolate; α and β fractions; bioactive

52

Separation of Functional Molecules in Food by Membrane Technology

proteins such as immunoglobulins, lactoferrin, lactoperoxidase, and glycomacropeptide; bioactive peptides; and minerals. These products have an excellent potential for use in the development of new functional foods and nutraceuticals (Durham and Hourigan, 2007) Also, whey proteins have demonstrated different physiological functions due to their numerous bioactive peptides that exhibit various properties such as antioxidative, antihypertensive, antimicrobial, immunoregulatory, angiotensinconverting enzyme inhibition, and mineral carrying capacity. These bioactive compounds can be produced by enzymatic hydrolysis of the protein coupled with various membrane separation procedures that can be used to fractionate the peptides based on size (Korhonan and Pihlanto, 2003). In order to recover all the bioactive fractions dairy processors and researchers continue to develop separation technologies based on size, density, charge, or hydrophobicity of the different components. In this respect different techniques are often combined in order to develop elaborate processes of sequential fractionation and purification and increase the recovery yield of high-value byproducts (Durham and Hourigan, 2007; El-Sayed and Chase, 2010a,b; Ndiaye et al., 2010). Thereby, the “bulk” whey proteins such as immunoglobulin (150 1000 kDa and 5.5 , pI , 8.3) and ovine serum albumin (66 kDa and pI 5 5.0 6 0.1) are positive in the acidic (pH 5 4.8 6 0.1) whey solutions, whereas for the smaller α-lactalbumin (14 kDa and pI 5 4.5 6 0.3) and β-lactoglobulin (18 kDa and pI 5 5.3 6 0.1), charge is expected to be weakly negative and positive, respectively (Galanakis, 2015a). For instance, immunoglobulin and ovine serum albumin have been quantitatively recaptured with a 300-kDa tubular ceramic membrane and pH 5 4 (Alme´cija et al., 2007). The selective recovery of a particular protein (i.e., α-lactalbumin) can be conducted by combining several effects, including reduced pore size and enhanced electrostatic repulsion between the charged membrane and protein species (Cowan and Ritchie, 2007).

2.4 SEPARATION AND RECOVERY OF MACRO- AND MICROMOLECULES USING MEMBRANE TECHNOLOGIES The most common methodology for the recovery of functional compounds from the aforementioned conventional and nonconventional bioresources is the so-called 5-Stages Universal Recovery Process, which progresses as follows (Galanakis, 2012, 2015a): 1. 2. 3. 4. 5.

macroscopic pretreatment, separation of macro- and micromolecules extraction isolation-purification product formation or encapsulation

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MF, ultrafiltration (UF), nanofiltration (NF), and electrodialysis (ED) are physicochemical and most importantly nondestructive technologies that could be used in the four first steps this methodology. Indeed, a usual practice is to concentrate bigger molecules (macromolecules) in the retentate and release smaller (micromolecules) in the permeate stream, respectively (Galanakis, 2015b). This approach looks simple at a theoretical level as the main fractionation mechanism of membranes is the “sieving” one that separates the molecules according to their MW. Nevertheless, in practice, this is not always the case since membrane pores are asymmetric, while the MWCO reflects the mean size of all membrane pores. To this line, the sieving effect is not always working strictly at the molecular level and indeed attenuates when the hydrophobic nature of the membrane surface and the solubility of the solutes are incorporated (Pinelo et al., 2009; Galanakis, 2015b). Subsequently, MWCO (although being an important factor) does not reflect an absolute barrier for the separation of macro- and micromolecules. Another issue to deal with is that functional molecules of natural sources do not move freely in solutions, but exist trapped within clusters of bioresource matrices. A typical example is phenols that bind noncovalently to proteins (Rawel et al., 2005) and dietary fibers (Bravo et al., 1994) of bioresources. In other words, smaller molecules like antioxidants could be trapped and recaptured in the retentate due to the structural characteristics of the macromolecules existing in the feed, and macromolecules could pass to the permeate due to the local structure of membrane pores in some points. If macroscopic pretreatment and extraction procedures are conducted prior the application of UF (e.g., via vacuum or thermal concentration, acid or enzyme extractions, etc.), the bioresource clusters could break, but also macromolecules may decompose leading to the formation of oligopolymer structures. This process affects the sieving mechanism and separation performance of UF membranes. On the other hand, if macro- and micromolecule complexes (i.e., whey proteins with phenols) have not been separated prior to the UF procedure, smaller molecules are covered in the concentrate stream (Galanakis, 2015a). The simultaneous recapture of macro- and micromolecules in one stream is a yield problem that leads to additional and costly purification stages. However, this fact may be desirable depending on the product that the food technologist is willing to develop (Galanakis, 2015b). In any case, researchers and professionals are nowadays preferring more and more membrane applications in order to separate all kind of functional compounds that exist in foods, for example, proteins, pectin, β-glucan, polyphenols, anthocyanins, tannins, flavonoids, carbohydrates and sugars in fruit juices, solutions, agricultural wastewaters, and beverages (Dı´az-Reinoso et al., 2009; Garcı´a-Martı´n et al., 2010; Galanakis et al., 2010; Kuhn et al., 2010; Cassano et al., 2013; He et al., 2013; Li et al., 2013).

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Separation of Functional Molecules in Food by Membrane Technology

Galanakis (2015a) revised five research studies (Galanakis et al., 2010, 2013, 2014, 2015; Patsioura et al., 2011) dealing with membrane separation mechanisms of macro- and micromolecules under similar processing conditions. These studies were conducted using a broad range of MWCO for the membranes, starting with UF and 100 kDa to the border of NF and 1 kDa. Experiments were conducted using two crossflow UF systems (DSS Labstak M20 and M10), seven membrane materials (GR40PP-100 kDa, GR51PP50 kDa, GR60PP-25 kDa, GR70PP-20 kDa, GR81PP-10 kDa, GR95PP10 kDa, and ETNA01PP-1 kDa) of the same manufacturer (Alfa Laval Nakskov), and different feeds extracted from food wastes and beverages. According to this review, separations were discussed in three categories according to the MW of the solutes (100 50, 25 10, and 2 1 kDa), providing insights about the separation mechanism of functional macro- and micromolecules using membrane technology. Thereby, by applying wide pore membranes of 100 50 kDa, the sieving mechanism dominates the separation of macro- and micromolecules making it rather distinct (Table 2.2). Experimenting with narrower membrane pores of 25 10 kDa (Table 2.3) and 2 1 kDa (Table 2.4), the separation based on molecular cutoff becomes more difficult and progresses in terms of components solubility, membrane hydrophobicity, and polarity resistance. The latest phenomenon leads to concentration polarization and fouling caused by the aggregation of proteins and polysaccharides on the membrane surface, or gel formation. However, separation opportunities for particular applications exist for the whole range (1 100 kDa) of the tested MWCO. The application of membranes such as polysulfone, which has a more asymmetric cutoff profile, can provide a degree of flexibility to the assayed separation. At this case, macromolecules can step in “gaps” and pass through membranes pores, whereas small polar molecules can stick in the polar membrane parts and get adsorbed on them. Polysulfone membranes in the range of 20 25 kDa were shown to be very efficient for the separation of: 1. polymeric from monomeric anthocyanins 2. pectin from phenolic compounds and cations 3. removal of “heavier” phenolic classes (autoxidated or compounds linked to macromolecules) without affecting the overall antioxidant properties of the permeate The utilization of a less hydrophobic and narrower membrane such as polyethersulfone of 10 or 2 kDa was shown to be reversely efficient. In particular, this membrane was able to absorb rapidly polar micromolecules such as hydroxycinnamic acid derivatives and at the same time to release oligosaccharide pectin fragments in the permeate. On the other hand, the more hydrophobic composite fluoropolymer was able to separate efficiently phenolic classes like hydroxycinnamic acids from flavonols (Galanakis, 2015a).

TABLE 2.2 Concentrations of Macro- and MicroMolecules Originating From Different Sources and Corresponding Retention Percentages Obtained Using Ultrafiltration Membranes (100 50 kDa) Substrate

Feed (Target Compounds)

Membrane Barrier MWCOa (kDa)

Material

Compounds Macromolecules

References Micromolecules

Group

C (mg/L)

R (%)

Group

Standard

Solution (β-glucan)

100

PSb

β-glucan

200 2000

92 95

n.d.c

Oat mill waste

Extract (β-glucan)

100

PSb

β-glucan

302 442

53 67

Saccharidesd

2317 5344

4 11

Proteins

190 376

35 40

Total phenols

16 31

3 9

Monov. ionse

1057 1699

2 3

Total sugars

384

,1

Total phenols

280

,1

o-diphenols

57

,1

Hyd.-cin. acidsf

19

,1

Flavonols

18

10

Monov. ionse

122

,1

Antirad. effic.g

1.7g

,1

Total phenols

68

13

Monov. ionse

1304

2

Olive millwastewater

AIRh from olive mill wastewater

Beverage (phenol)

Water soluble extract (pectin)

100

100

PSb

PSb

n.d.c

Pectin

87

79

C (mg/L)

R (%) Patsioura et al. (2011) Patsioura et al. (2011)

Galanakis et al. (2010)

Galanakis et al. (2010)

(Continued )

TABLE 2.2 (Continued) Substrate

Winery sludge

Feed (Target Compounds)

Extract (phenols and anthocyanins)

Membrane Barrier a

MWCO (kDa) 100

Compounds

Material

PS

b

References

Macromolecules

Micromolecules

Group

C (mg/L)

R (%)

Pectin

6443

12

Polanthoc.i

172

59

Group

C (mg/L)

R (%) Galanakis et al. (2013)

Total sugars

3910

61

Red. sugarsj

412

50

Nonred. sugarsk

3498

62

Total phenols

1965

64

o-diphenols

560

52

Hyd.-cin. acidsf

297

57

265

43

Flavonols l

Total anth.

249

61

Monom. anth.m

76

59

Diluted extract (phenols and anthocyanins)

100

PSb

Pectin

1670

6

Total sugars

1065

74

Polanthoc.h

172

77

Red. sugarsj

129

58

Nonred. sugarsk

935

76

Total phenols

476

69

o-diphenols

560

80

Hyd.-cin. acidsf

297

99

265

68

Flavonols l

Anari cheese

Halloumi cheese

Whey (protein and sugars)

Whey (protein and sugars)

100

100

PSb

PSb

Proteins

Proteins

3723

1087

76

69

Total anth.

249

61

Monom. anth.m

76

77

Total sugars

49,703

9

Red. sugarsj

469

86

Nonred. sugarsk

48,581

7

Total phenols

112

78

Total sugars

12,729

2

Red. sugarsj

182

50

Nonred. sugarsk

12,533

2

Total phenols

43

55

Galanakis et al. (2013)

Galanakis et al. (2014)

Galanakis et al. (2014)

(Continued )

TABLE 2.2 (Continued) Substrate

Anari cheese

Halloumi cheese

a

Feed (Target Compounds)

Whey (protein and sugars)

Whey (protein and sugars)

Membrane Barrier a

MWCO (kDa) 50

50

Compounds

Material

PS

b

PSb

Macromolecules

References Micromolecules

Group

C (mg/L)

R (%)

Group

C (mg/L)

R (%)

Proteins

3723

73

Total sugars

49703

8

Red. sugarsj

469

82

Nonred. sugarsk

48,581

7

Total phenols

112

74

Total sugars

12,729

18

Red. sugarsj

182

33

Nonred. sugarsk

12,533

18

Total phenols

43

66

Proteins

1087

68

Galanakis et al. (2014)

Galanakis et al. (2014)

MWCO, molecular weight cutoff. PS, polysulfone. n.d., not determined. d Saccharides include oligo-, di-, and monosaccharides. e Monov. ions, monovalent ions. f Hyd.-cin. acids, hydroxycinnamic acid derivatives. g Antirad. effic., antiradical efficacy expressed in mg DPPH/g. h AIR, alcohol insoluble residue. i Pol-anthoc., polymeric anthocyanins. j Red. sugars, reducing sugars. k Nonred. sugars, nonreducing sugars. l Total anth., total anthocyanins. m Monom. anth., monomeric anthocyanins. Source: Adapted from Galanakis, C.M., Kotanidis, A., Dianellou, M., & Gekas, V. (2015). Phenolic content and antioxidant capacity of Cypriot Wines. Czech J. Food Sci. 33(2), 126 136. b c

TABLE 2.3 Concentrations of Macro- and Micromolecules Originated From Different Sources and Corresponding Retention Percentages Obtained Using Ultrafiltration Membranes (25 10 kDa) Substrate

Olive mill wastewater

Feed (Target Compounds)

Beverage (phenol)

Membrane Barrier MWCOa (kDa) 25

Compounds

Material

Macromolecules Group

PS

b

C (mg/L)

References Micromolecules

R (%)

c

n.d.

Group

C (mg/L)

R (%)

Total sugars

384

18

Total phenols

280

10

o-Diphenols

57

6

Hyd.-cin. acidsd

19

32

18

37

Flavonols Monov. ions

e

122 f

g

AIR from olive mill wastewater

Water soluble extract (pectin)

25

PS

b

Pectin

87

98

f

Galanakis et al. (2010)

26

Antirad. effic.

1.7

8

Total phenols

68

40

Monov. ionse

1304

10

Galanakis et al. (2010)

(Continued )

TABLE 2.3 (Continued) Substrate

Winery sludge

Feed (Target Compounds)

Extract (phenols and anthocyanins)

Membrane Barrier MWCO (kDa) 20

a

Compounds

Material

PS

b

References

Macromolecules

Micromolecules

Group

C (mg/L)

R (%)

Group

C (mg/L)

R (%)

Pectin

6443

64

Total sugars

1065

87

Polanthoc.h

172

92

Red. sugarsi

129

78

Nonred. sugarsj

935

88

Total phenols

476

85

o-diphenols

560

87

Hyd.-cin. acidsd

297

81

265

65

249

89

Monom. anth.

76

86

Flavonols k

Total anth.

l

Diluted extract (phenols and anthocyanins)

20

PS

b

Pectin

1670

52

Total sugars

1065

78

Polanthoc.h

172

94

Red. sugarsi

129

78

Nonred. sugarsj

935

78

Total phenols

476

77

o-diphenols

560

85

Galanakis et al. (2013)

Galanakis et al. (2013)

Hyd.-cin. acidsd

297

99

265

75

249

62

Monom. anth.

76

17

Total sugars

49,703

21

Red. sugarsi

469

74

Nonred. sugarsj

48,581

22

Total phenols

112

78

Total sugars

12729

34

Red. sugarsi

182

54

Nonred. sugarsj

12,533

35

Flavonols k

Total anth.

l

Anari cheese

Anari cheese

Olive mill wastewater

Whey (protein and sugars)

Whey (protein and sugars)

Beverage (phenol)

20

20

10

PS

PS

b

b

PESf

Proteins

Proteins

n.d.c

3723

1087

84

76

Total phenols

43

59

Total sugars

384

32

Total phenols

280

21

o-Diphenols

57

32

Hyd.-cin. acidsd

19

44

18

56

Flavonols e

Monov. ions

f

Antirad. effic.

122

23

f

24

1.7

Galanakis et al. (2014)

Galanakis et al. (2014)

Galanakis et al. (2010)

(Continued )

TABLE 2.3 (Continued) Substrate

g

AIR from olive mill wastewater a

Feed (Target Compounds)

Water soluble extract (pectin)

Membrane Barrier MWCO (kDa) 10

a

Compounds

Material

f

PES

Macromolecules

References Micromolecules

Group

C (mg/L)

R (%)

Group

C (mg/L)

R (%)

Pectin

87

98

Total phenols

68

71

Monov. ionse

1304

49

Galanakis et al. (2010)

MWCO, molecular weight cutoff. PS, polysulfone. n.d., not determined. d Hyd.-cin. acids, hydroxycinnamic acid derivatives. e Monov. ions, monovalent ions. f Antirad. effic., antiradical efficacy expressed in mg DPPH/g. g AIR, alcohol insoluble residue. h Pol-anthoc., polymeric anthocyanins. i Red. sugars, reducing sugars. j Nonred. sugars, nonreducing sugars. k Total anth., total anthocyanins. l Monom. anth., monomeric anthocyanins. Source: Adapted from Galanakis, C.M. (2015a). Chapter 3: Development of a universal recovery strategy. In: Galanakis, C.M. (Ed.), Food Waste Recovery: Processing Technologies and Techniques. Elsevier Inc.: Waltham; Galanakis, C.M. (2015b). Separation of functional macromolecules and micromolecules: from ultrafiltration to the border of nanofiltration. Trends Food Sci. Technol. 42, 44 63. b c

TABLE 2.4 Concentrations of Macro- and Micromolecules Originated From Different Sources and Corresponding Retention Percentages Obtained Using Membranes in the Edge of Ultrafiltration With Nanofiltration (2 1 kDa) Substrate

Olive mill wastewater

Feed (Target Compounds)

Beverage (phenol)

Membrane Barrier a

MWCO (kDa) 2

Compounds

Material

Macromolecules Group

b

PES

References

C (mg/L)

Micromolecules R (%)

c

n.d.

Group

C (mg/L)

R (%)

Total sugars

384

38

Total phenols

280

25

57

48

19

53

Flavonols

18

62

Monov. ionse

122

27

Total phenols

68

81

1304

55

o-Diphenols Hyd.-cin. acids

f

b

PES

Pectin

87

99

d

Galanakis et al. (2010)

AIR from olive mill wastewater

Water soluble extract (pectin)

2

Winery sludge

Extract

2

PESb

n.p.g

n.p.g

Galanakis et al. (2013)

Diluted extract

2

PESb

n.p.g

n.p.g

Galanakis et al. (2013)

e

Monov. ions

Galanakis et al. (2010)

(Continued )

TABLE 2.4 (Continued) Substrate

Anari cheese

Feed (Target Compounds)

Ultrafiltered whey (protein and sugars)

Membrane Barrier MWCOa (kDa) 2

Compounds

Material

b

PES

Macromolecules

References Micromolecules

Group

C (mg/L)

R (%)

Group

C (mg/L)

R (%)

Proteins

652

35

Total sugars

38,402

13

135

11

Nonred. sugars

37,805

13

Total phenols

27

9

Total sugars

8212

5

81

11

Nonred. sugars

7668

5

Total phenols

16

31

Red. sugarsh i

Halloumi cheese

Ultrafiltered whey (protein and sugars)

2

b

Proteins

PES

275

47

Red. sugarsh i

Winery sludge

Extract (phenols and anthocyanins)

1

j

ETNA

Pectin

6443

47

Total sugars

1065

76

Polanthoc.k

172

56

Red. sugarsh

129

66

Nonred. sugarsi

935

77

Total phenols

476

74

560

67

Hyd.-cin. acids

297

77

Flavonols

265

45

Total anth.l

249

57

76

55

o-diphenols d

Monom. anth.

m

Galanakis et al. (2014)

Galanakis et al. (2014)

Galanakis et al. (2013)

Diluted extract (phenols and anthocyanins)

1

ETNAj

Pectin Polanthoc.k

1670 172

39

Total sugars

45

h

1065

64

Red. sugars

129

57

Nonred. sugarsi

935

65

Total phenols

476

56

o-diphenols

560

64

297

80

265

53

249

44

Monom. anth.

76

41

Total sugars

38,402

24

135

62

Nonred. sugars

37,805

23

Total phenols

27

36

Total sugars

8212

23

Red. sugarsh

81

21

Nonred. sugarsi

7668

23

Total phenols

16

23

Hyd.-cin. acids

d

Flavonols l

Total anth.

m

Anari cheese

Ultrafiltered whey (protein and sugars)

1

j

ETNA

Proteins

652

24

Red. sugarsh i

Ultrafiltered whey (protein and sugars)

1

j

ETNA

Proteins

275

42

Galanakis et al. (2013)

Galanakis et al. (2014)

Galanakis et al. (2014)

(Continued )

TABLE 2.4 (Continued) Substrate

Dry red wine

Feed (Target Compounds)

Sixfold diluted (phenolics and anthocyanins)

Membrane Barrier a

MWCO (kDa) 1

Compounds

Material

Macromolecules Group

j

ETNA

References

c

n.d.

C (mg/L)

Micromolecules R (%)

Group

C (mg/L)

Total phenols

1930 4413

69 90

Hyd.-cin. acidsd

121 444

42 53

Flavonols

118 369

9 40

75 559

21 71

Total anth.l n

n

28 63

Antirad. effic.

o

Sweet red wine

Sixfold diluted (phenolics and anthocyanins)

1

ETNA

c

n.d.

466 806

66 85

730

65

87

67

Flavonols

81

25

Total anth.l

19

26

Antirad. effic.n

6n

31

FRAP activityo

98o

60

Total phenols Hyd.-cin. acids

d

Galanakis et al. (2015)

11 57 o

FRAP activity j

R (%)

Galanakis et al. (2015)

Dry white wine

Sixfold diluted (phenolics and anthocyanins)

1

ETNAj

n.d.c

Total phenols

224

23

19

63

30

49

15

28

Antirad. effic.

4

n

29

FRAP activityo

95o

57

Hyd.-cin. acids Flavonols Total anth.l n

a

MWCO, molecular weight cutoff. PES, polyethersulfone. n.d., not determined. d Hyd.-cin. acids, hydroxycinnamic acid derivatives. e Monov. ions, monovalent ions. f AIR, alcohol insoluble residue. g n.p., no permeate. h Red. sugars, reducing sugars. i Nonred. sugars, nonreducing sugars. j ETNA, composite fluoropolymer. k Pol-anthoc., polymeric anthocyanins. l Total anth., total anthocyanins. m Monom. anth., monomeric anthocyanins. n Antirad. effic., antiradical efficacy expressed in mg DPPH/g. o FRAP activity expressed in µg TROLOX/mL. b c

d

Galanakis et al. (2015)

68

Separation of Functional Molecules in Food by Membrane Technology

2.5 CONCLUSIONS Taking into consideration all of the above, the future trend in the development of novel functional foods and nutraceutical products has already begun by accepting the concept of waste recovery and must continue through applying the most suitable extraction and purification technologies. The effective recovery of biologically-active components from different types of raw materials and byproducts is a constant challenge. In the recovery process it is necessary not only to ensure a good extraction yield at low cost and energy consumption, but also to ensure the purification of the bioactives by separating them from the complex matrix while maintaining their functional properties. Thus, success in developing new functional ingredients and innovative products is closely related to the efficiency of the separation/purification step of bioactive compounds. Membrane processing is one of the most promising technologies for the recovery of these valuable compounds from agroindustrial waste streams. Membrane systems, compared to the conventional methods, have several advantages, including versatility (e.g., depending on the membrane characteristics and on the used solvent, different compounds can be separated); mild operating conditions (e.g., minimal thermal damage); scalability at industrial level; environmental friendliness (e.g., low energy consumption); and economic feasibility (e.g., low cost).

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FURTHER READING Ghoreishi, S., Shahrestani, R., 2009. Subcritical water extraction of mannitol from olive leaves. J. Food Eng. 93 (4), 474 481.