WO2017111761A1 - Processus et procédé pour la récupération optimale de caroténoïdes à partir de plantes - Google Patents

Processus et procédé pour la récupération optimale de caroténoïdes à partir de plantes Download PDF

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Publication number
WO2017111761A1
WO2017111761A1 PCT/TR2016/050538 TR2016050538W WO2017111761A1 WO 2017111761 A1 WO2017111761 A1 WO 2017111761A1 TR 2016050538 W TR2016050538 W TR 2016050538W WO 2017111761 A1 WO2017111761 A1 WO 2017111761A1
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Prior art keywords
carotenoid
acid
water
source
chain fatty
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PCT/TR2016/050538
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English (en)
Inventor
Gul Bahar BASIM DOGAN
Arisan INCE
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Biocapsol Kimya A. S.
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Publication of WO2017111761A1 publication Critical patent/WO2017111761A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
    • A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
    • A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/10—Purification; Separation; Use of additives by extraction, i.e. purification or separation of liquid hydrocarbons with the aid of liquids

Definitions

  • the present invention relates to a process for producing carotenoids, particularly lycopene, from plants or plant constituent parts, particularly from fruits and vegetables.
  • Dietary carotenoids are known to have health benefits as supplements in decreasing the risk of diseases, particularly certain cancers and eye diseases.
  • the carotenoids that have been most commonly studied in this regard are ⁇ -carotene, lycopene, and lutein.
  • the health benefits of the carotenoids as dietary supplements are thought to be due to their activity as antioxidants.
  • Carotenoids can be industrially obtained by extraction from fruits and vegetables, which have high concentrations of these substances by using organic solvents or supercritical fluids. Other methods utilized for carotenoid extraction are the fermentation of certain species of microorganisms (fungi or bacteria) or chemical synthesis.
  • Carotenoids which are well credited for important health-promoting functionalities can also be found in the waste products originating from certain processing plants such as tomato peel from tomatoes dice, pure, sauce or paste production. To date, several problems related to the recovery and purification of carotenoids from plant products have been addressed. Generally, the core problem remains to be able to recover such organic molecules from a matrix, which is substantially cellulosic in nature.
  • Lycopene is a carotenoid responsible for the red color of a large number of fruits and vegetables. Consumption of lycopene from tomatoes has been associated with protection against oxidative DNA damage in addition to their anticancer properties (Agarwal & Rao, 2000) and their functionality in the prevention of cardiovascular diseases. Studies so far have indicated that consumption of tomatoes and tomato sauce is directly associated with a reduced risk of developing different types of cancers of the digestive system and prostate cancer. Apart from potential health benefits, lycopene is also used as an alternative to synthetic food colorants. Here, it should be noted that lycopene covers a wide range of colors ranging from light yellow, passing through orange, to an intense color of red.
  • Lycopene is insoluble in water, and can be dissolved only in organic solvents and oils and is susceptible to degradation by UV light, which limits its shelf-life after extraction from the raw plants.
  • the extraction efficiency of carotenoids can be improved by using solvent combinations to facilitate partitioning.
  • solvent combinations to facilitate partitioning.
  • organic solvents or solvent combinations such as hexane, ethanol, acetone, etc.
  • lycopene In its natural form, lycopene is heat resistant and present in a thermodynamically stable state as all-trans isomer crystal within the chloroplasts of plant cells (Harris & Spurr, 1969). Conventional extraction often requires heat to facilitate the migration of solvent to extract pigment compounds. Although increased temperatures correspond to improved solubility and organelle membrane disruption, heat and UV exposure should be limited when possible due to the thermo labile nature of carotenoids once they are in the solvent (Rodriguez- Amaya, 2001).
  • Extraction efficiency of carotenoids including lycopene can be improved by using solvent combinations. Comparison of efficiency among different solvents for carotenoid extraction from various plant materials is presented in the literature, but most of them deal with optimization of the extraction conditions.
  • Baysal et al. T. Baysal, S. Ersus, D.A.J. Starmans, Supercritical C02 extraction of ⁇ -carotene and lycopene from tomato paste waste, J. Agric. Food Chem. 48 (11) (2000) 5507-5511) observed highest yield (54%) of lycopene at 55 °C, 30 MPa and a flow rate of 4 kg/h with 5% ethanol used as a modifier.
  • Karaj et al. investigated the extraction of lycopene and ⁇ -carotene from tomato skin using near critical liquid carbon dioxide in the presence of oleic acid as a modifier. They observed that the oleic acid as co-solvent has a beneficial role in the stability of cis-isomer of lycopene (0.19-0.067 ⁇ g/g sample).
  • the mobile phase is subjected to pressures and temperatures near or above the critical point for the purpose of enhancing the mobile phase solvating power.
  • the process begins with C0 2 in vapor phase, which is then compressed into a liquid before becoming supercritical. It is a relatively rapid method because of the low viscosities and high diffusivities associated with the supercritical fluids.
  • the extraction can be selective to some extent by controlling the densities of the medium.
  • the extract is easily recovered by simply depressurizing in the system, allowing the supercritical fluid to return to the gas phase and evaporate, leaving little or no amount of solvent residue.
  • this process has some disadvantages which make its applicability limited at the industrial scale for lycopene production including: (i) a high operational pressure is required which increases the processing cost in addition to the related safety concerns and environmental hazards;
  • An objective of the present invention is to provide a process for production of carotenoid extract from carotenoid sources.
  • a process producing carotenoid extract from a carotenoid source comprising: Providing a carotenoid source;
  • At least one component selected from medium chain fatty acids, water-soluble primary alcohols and water-soluble secondary alcohols, and isomers thereof;
  • the present invention provides a method for production of carotenoid from a carotenoid source.
  • the present invention provides a caretonoid extract product comprising at least one acetal compound, and at least one component selected from medium chain fatty acids, water-soluble primary alcohols and water-soluble secondary alcohols, and isomers thereof.
  • the present invention provides a use of carotenoid extract product as a food colorant or antioxidant.
  • FIG. 1 is a graph showing lycopene concentration in selected solvents immediately after extraction in accordance with an embodiment of the present invention and after 6 months.
  • the present invention provides processes for production of carotenoids from plants or plant constituent parts via solvent extraction. From here on a plant or plant constituent part containing carotenoid will be referred to as a carotenoid source.
  • a carotenoid source From here on a plant or plant constituent part containing carotenoid will be referred to as a carotenoid source.
  • the present invention provides a process for producing carotenoid extract via the extraction of carotenoid that is contained in a carotenoid source, which from hereon will be referred to as a process of the present invention.
  • the process of the present invention can be applied to any carotenoid source.
  • the carotenoid source can be, for example, tomatoes, watermelons, rosehip and gac fruit as the source of lycopene; orange plants, carrots, pumpkins and sweet potatoes as the source of ⁇ -carotene; tobacco leaves as the source of nicotine; green leafy vegetables such as spinach, kale and yellow carrots as the source of lutein.
  • the carotenoid source corresponds to the industrial waste generated in the tomato processing industry.
  • waste is comprised of tomato peels which are rich in fibers and pulp attached thereto, as well as tomato seeds.
  • the waste material contains high amounts of lycopene (40-50 g/kg) when dried depending on the variety of the tomato.
  • waste product from industrial tomato processing as a carotenoid source for the present invention allows the recovery of a material which is currently either used as animal food or even discarded.
  • extraction of lycopene from the waste of industrial tomato processing is an example of bio refinery; i.e., a process which integrates an established industrial process by-product, in this case from industrial tomato processing, to generate substances with a high added value.
  • the carotenoid source corresponds to the leaves of green leafy vegetables such as spinach, kale and yellow carrots.
  • the carotenoid source before being extracted, is dried until it reaches a suitable degree of humidity in order to avoid degradation of the carotenoid.
  • the tomato waste as the lycopene source is dried between 30 - 60°C for 2-5 hours to reach a 3-5 wt% moisture content.
  • the carotenoid source with the appropriate degree of humidity, is grounded or milled to obtain suitable particle size in order to increase the total surface area of the reaction and to facilitate extraction.
  • the tomato waste as the carotenoid source is grounded or milled to obtain a predetermined particle size.
  • the mean particle size is between 50 to 500 micrometer. In general, reduction of the particle size increases the yield of the carotenoid and the extraction rate.
  • the process of the present invention utilizes an extraction solvent including medium-chain fatty acids (MCFAs) in combination with , water-soluble primary and secondary alcohols including ethanol, propanol, buthanol, and isomers thereof, and acetal compounds as the extraction solvent, from here on referred to as an extraction solvent of the present invention.
  • MCFAs medium-chain fatty acids
  • water-soluble primary and secondary alcohols refers to the primary and secondary alcohols having a minimum of at least 5% by volume of water- solubility at 1 atm25 °C. As the number of Carbon atoms in the chain increase, the less soluble will be the alcohol in water. For ease of solvent recovery and achieving optimum viscosity, solubility of the extraction solvent is required. The viscosity of the extraction product to be obtained is around 1.00 + 0.5 MPa.s within the temperature range of 0-100 °C.
  • the suitable alcohols of the present invention include ethanol, propanol and butanol, and isomers thereof.
  • the alcohol of the present invention is at least one selected from ethanol, propanol and butanol, and isomers thereof.
  • the alcohol of the present invention is at least one selected from propanol and butanol, and isomers thereof.
  • the alcohol of the present invention is 1 -propanol.
  • the extraction solvent of the present invention when used, a greater yield of carotenoid extraction is possible from carotenoid sources as compared to the pure MCFAs and pure solvents.
  • the use of MCFAs in combination with water-soluble primary alcohols, water-soluble secondary alcohols, and acetal compounds as the extraction solvent contributed to the yield of carotenoid extract.
  • the expression "medium-chain fatty acids” refers to the fatty acid composed of a glycerol backbone and three fatty acids in which 2 or 3 of the fatty acid chains attached to glycerol are medium-chain in length.
  • the medium-chain fatty acid is selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linolenic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid and cerotic acid.
  • the medium-chain fatty acid of the present invention is at least one selected from the group consisting of caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, oleic acid, linolenic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid and cerotic acid.
  • the medium chain fatty acid of the present invention is at least one selected from oleic acid and linolenic acid.
  • the medium chain fatty acid of the present invention is oleic acid.
  • Suitable acetal compounds of the present invention include dimethoxymethane, diethoxymethane, dipropoxymethane, dibutoxymethane and 2-ethylhexylal.
  • the acetal compound of the present invention is at least one selected from dimethoxymethane, diethoxymethane, dipropoxymethane, dibutoxymethane and 2- ethylhexylal.
  • the acetal compound of the present invention is dimethoxymethane.
  • One preferred embodiment of the extraction solvent of the present invention comprises one or more component selected from the group consisting of ethanol, propanol, butanol and isomers thereof, and diethoxymethane.
  • the extraction solvent of the present invention comprises at least one medium chain fatty acid and an acetal compound.
  • at least one medium chain fatty acid is oleic acid or linolenic acid
  • at least one acetal compound is selected from dimethoxymethane, diethoxymethane, dipropoxymethane, dibutoxymethane and 2- ethylhexylal. More preferably, at least one medium chain fatty acid is oleic acid and at least one acetal compound is diethoxymethane.
  • the extraction solvent of the present invention comprises at least one alcohol selected from the group consisting of water-soluble primary alcohols, water- soluble secondary alcohols and isomers thereof, and at least one acetal compound.
  • at least one alcohol is selected from ethanol, propanol and butanol, and isomers thereof, and at least one acetal compound is selected from dimethoxymethane, diethoxymethane, dipropoxymethane, dibutoxymethane and 2-ethylhexylal. More preferably, at least one alcohol is 1 -propanol and at least one acetal compound is diethoxymethane.
  • acetal compounds in combination with water-soluble primary alcohols, water- soluble secondary alcohols, and isomers thereof, and in combination with medium chain fatty acids, as well as the use of medium chain fatty acids in combination with water-soluble primary alcohols, water-soluble secondary alcohols, and acetal compounds has additional advantages, apart from producing a carotenoid extract with a higher carotenoid content compared to the use of pure MCFAs and pure solvents, as described below.
  • the component of the extraction solvent of the present invention i.e. medium chain fatty acids, are abundantly present in plants and plant constituent parts making the process of extraction in the invention easily applicable industrially. For example, many of the vegetable oils such as hazelnut oil, sunflower oil and olive oil contain oleic acid.
  • lycopene produced by using the process of the present invention provides an endurance of lycopene in its cis- isomer till 70 °C in confectionary as a food colorant, and till 140 °C for 1 minute for the use of lycopene in dairy products without degradation.
  • a carotenoid source that is adequately treated is introduced into an extractor and the extraction solvent mixture of the present invention is passed through the starting material of the carotenoid source, under ambient pressure and pre-set temperature conditions which permit the solubilisation of the carotenoid in the extraction solvent.
  • the extraction solvent extracts the soluble components from the starting material of the carotenoid source. Then the soluble components are moved to the separators where the desired product is obtained.
  • the pressure and temperature conditions are chosen such that they permit an adequate solubility of the carotenoid.
  • the extraction of lycopene by the use of oleic acid in combination with ethanol is carried out under pressure of 1 atm (ambient) and at a temperature of 25-100 °C.
  • the extraction of lycopene by the use of oleic acid in combination with diethoxymethane is carried out under ambient pressure and at a temperature range of 25-100 °C.
  • the extraction product obtained in the extraction stage is purified and the remaining solvent mixture is removed from the medium. Furthermore, it is possible to recycle and reuse the fatty acids that are used for the extraction process which may further contain the fatty acids from the product itself.
  • lycopene is known to decompose at around 70 °C and above using the process disclosed in the present invention lycopene is protected up to a minimum of 100 °C.
  • the present invention provides a carotenoid extract obtained by the process of the present invention.
  • carotenoid extract refers to the extract containing carotenoid in a concentration higher than that is present in the natural product from which it has been obtained (carotenoid source).
  • the concentration of carotenoid in the extract obtained from the industrial waste of the tomato processing, e.g., tomato skins reaches a concentration of 10000-120000 ppm following the process of the invention.
  • the carotenoid extract product of the present invention comprises at least one acetal compound, and at least one component selected from at least one medium chain fatty acids, water-soluble primary alcohols and water-soluble secondary alcohols, and isomers thereof.
  • the caretonoid extract product of the present invention comprises at least one acetal compound, at least one medium chain fatty acid and at least one alcohol selected from the group consisting of water-soluble primary alcohols and water-soluble secondary alcohols, and isomers thereof.
  • the carotenoid extract obtained by the present invention has usage as a colorant and/or antioxidant properties and can be used to elaborate products that contain these extracts.
  • the present invention provides a composition, from here on referred to as the composition of the present invention that contains this carotenoid extract in combination with an appropriate diluent.
  • the composition of the present invention can contain one or more of the selected additives, for example antioxidants, emulsifying agents or mixtures thereof.
  • the composition of the invention can be a food, cosmetic, pharmaceutical or nutraceutical product.
  • composition of the present invention can be obtained by diluting the concentrate of the invention with a diluent to achieve the appropriate carotenoid extract and, alternatively, by adding one or two more appropriate additives, for example, antioxidants, emulsifiers and mixtures thereof.
  • the composition of the present invention can contain a variable amount of carotenoid, depending on the application for which it is put in use.
  • any substance can be used in which the carotenoid is soluble, for example, fats, oils and mixtures thereof.
  • the diluents are comprised of one or more vegetable oils, for example, olive oil, walnut oil, sunflower oil.
  • any antioxidant can be used, for example ascorbic acid (vitamin C), and/or tocopherols (vitamin E etc.)
  • any emulsifier can be used, for example, lecithin, monoglycerides etc.
  • composition of the present invention can be presented in any presentation phase, liquid or solid, for example, encapsulated in soft gelatin capsules.
  • This invention is of interest to any industry that generates waste products containing carotenoid, for example, in the tomato processing industry where the residual products are an excellent source of lycopene.
  • Lycopene extracts provided by this invention, and the compositions they contain, are mainly destined for the food industry.
  • the second series of experiments were conducted with mixtures of ethanol and oleic acid; diethoxymethane and oleic acid as well as hexane with oleic acid at varying amounts of 10:90 and 80:20 (v/v), solvent to waste ratio varying between 3: 1 and 10: 1 (v/w), and particle size in the range of 0.5 and 1.0 mm.
  • Lycopene concentrations in the extracting solvent were determined spectrophotometrically at room temperature using 1-cm path length quartz cuvettes and a double-beam UV-VIS spectrophotometer (SHIMADZU UV-3600-UV-VIS-NIR Spectrophotometer). Absorption spectra were identical to that of the lycopene standard and displayed the three characteristic peaks of lycopene at around 445, 472 and 503 nm. To minimize the interference from other carotenoids, the concentration of lycopene was calculated at 503 nm using the molar extinction coefficient 17.2xl0 4 M _1 cm "1 . The results of the experiments are presented in FIG.1.
  • FIG. 1 shows lycopene concentration in the selected solvents immediately after the extraction and after 6 months.
  • FIG. 1 shows the total carotenoid yield after extraction step (repeated twice) and the percentage of individual carotenoids identified by UV VIS measurements. It is shown that the combination of oleic acid with ethanol and diethoxymethane synergistically improved the total yield compared with that obtained by any of the individual solvents as well as that obtained by the combination of oleic acid with hexane. Although hexane is the best solvent to extract the lycopene, it results in the most amount of decay as a function of time. Oleic acid itself or in combination with ethanol or diethoxymethane has been shown to prevent a large percent decay in the lycopene content for six months as compared to pure hexane.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Mycology (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Botany (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

La présente invention concerne un procédé de production d'extrait de caroténoïdes à partir d'une source de caroténoïdes, le procédé comprenant : la fourniture d'une source de caroténoïdes; la fourniture d'un solvant d'extraction comprenant au moins un composé acétal et au moins un composant choisi parmi les acides gras à chaîne moyenne, les alcools primaires hydrosolubles et les alcools secondaires hydrosolubles; le mélange de la source de caroténoïdes avec le solvant d'extraction; l'extraction des composants solubles de la source de caroténoïdes pour produire un l'extrait de caroténoïdes.
PCT/TR2016/050538 2015-12-24 2016-12-26 Processus et procédé pour la récupération optimale de caroténoïdes à partir de plantes WO2017111761A1 (fr)

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TR2015050264 2015-12-24

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115734714A (zh) * 2020-03-24 2023-03-03 C·V·萨万基卡尔 富含β-胡萝卜素的油

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WO2001046133A1 (fr) * 1999-12-21 2001-06-28 Fermentron Ltd. Procedes d'extraction de carotenoides et de preparations de matieres alimentaires
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MACHMUDAH ET AL., J. FOOD ENGINEERING, vol. 108, 2012, pages 290 - 296
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115734714A (zh) * 2020-03-24 2023-03-03 C·V·萨万基卡尔 富含β-胡萝卜素的油

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