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WO2023174942A1 - Procédé de réduction de la teneur en composés cyanogéniques dans des graines végétales - Google Patents

Procédé de réduction de la teneur en composés cyanogéniques dans des graines végétales Download PDF

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Publication number
WO2023174942A1
WO2023174942A1 PCT/EP2023/056492 EP2023056492W WO2023174942A1 WO 2023174942 A1 WO2023174942 A1 WO 2023174942A1 EP 2023056492 W EP2023056492 W EP 2023056492W WO 2023174942 A1 WO2023174942 A1 WO 2023174942A1
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Prior art keywords
plant seeds
less
weight
treated plant
treated
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German (de)
English (en)
Inventor
Sebastian JESCHKO
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Kern Tec GmbH
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Kern Tec GmbH
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Priority to EP23711720.5A priority Critical patent/EP4492966A1/fr
Publication of WO2023174942A1 publication Critical patent/WO2023174942A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01H—NEW PLANTS OR NON-TRANSGENIC PROCESSES FOR OBTAINING THEM; PLANT REPRODUCTION BY TISSUE CULTURE TECHNIQUES
    • A01H3/00—Processes for modifying phenotypes, e.g. symbiosis with bacteria
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/30—Physical treatment, e.g. electrical or magnetic means, wave energy or irradiation

Definitions

  • the field of the present invention is that of methods for depleting cyanogenic compounds in plant seeds.
  • cyanogenic compounds such as cyanogenic glycosides (e.g. amygdalin or linustatin). Since toxic hydrogen cyanide is produced from the cyanogenic compounds by various enzymes when the plant seeds are consumed, the plant seeds are toxic to the consumer above a certain dose and are therefore not suitable for use as food or animal feed unless they have been processed accordingly beforehand.
  • a common method for detoxification is to boil the plant seeds in order to deactivate the enzymes that are ultimately responsible for the release of hydrogen cyanide from the cyanogenic compounds.
  • this destroys valuable aromas.
  • Another well-known approach - and often associated with boiling - is to soak the plant seeds in water for a longer period of time (usually around 24 hours) in order to promote the conversion of the cyanogenic compounds and the associated release of the hydrogen cyanide. The water containing hydrogen cyanide is then discarded. However, cooking or washing out destroys or rinses out flavors and proteins.
  • Documents CN 110547391 A, CN 210988069 U and CN 210988068 U concern detoxification processes for flaxseed.
  • Yamashita et al. (“Development of a method to remove cyanogen glycosides from flaxseed meal.” International Journal of food science & Technology 42.1 (2007): 70-75.) concerns the detoxification of pressed flaxseed.
  • deoiled linseed was incubated for 18 hours in 0.IM sodium citrate buffer and then dried in a continuous steam oven at 120°C.
  • this method has numerous disadvantages. These include, among other things, the long incubation period, the high drying temperatures and the use of the acidity regulator sodium citrate (E331). This process is also not well suited for large-scale use; the harsh process conditions also affect the taste of the linseed and lead to a loss of other valuable ingredients (especially proteins).
  • GN 105341629 A also discloses a process for debittering apricot kernels.
  • El-Adawy et al. Biochemical studies of some non-conventional sources of proteins Part 7. Effect of detoxification treatments on the nutritional quality of apricot kernels.” Food/Nahrung 38.1 (1994): 12-20.) the quality of apricot kernels is examined after a debittering process .
  • this process is as gentle as possible (so that, for example, the taste, as well as the entire sensory system, and valuable ingredients of the plant seeds are preserved as much as possible, and the plant seeds remain as intact or as firm as possible) and well suited for large-scale use is .
  • the present invention provides a method for depleting cyanogenic compounds in plant seeds, comprising the following steps: a) providing plant seeds, the plant seeds containing cyanogenic compounds, b) treating the plant seeds with electroporation, in particular Pulsed Electric Fields (PEF), and c ) Depletion of cyanogenic compounds in the plant seeds treated (by electroporation).
  • electroporation in particular Pulsed Electric Fields (PEF)
  • PEF Pulsed Electric Fields
  • the present invention relates to treated plant seeds obtainable by this process.
  • the invention provides treated plant seeds, preferably linseeds or stone fruit seeds.
  • the content of cyanogenic compounds in the treated plant seeds is so low that, in relation to the total mass of the treated plant seeds, less than 1000 mg/kg, preferably less than 800 mg/kg, more preferably less than 600 mg/kg, even more preferably less than 400 mg/kg or even less than 300 mg/kg, in particular less than 200 mg/kg or even less than 150 mg/kg hydrocyanic acid can be released.
  • the content of cyanogenic compounds in the treated plant seeds is preferably so low that, in relation to the total mass of the treated plant seeds, less than 50 mg/kg, preferably less than 25 mg/kg, even more preferably less than 20 mg/kg or even less than 15 mg/kg can be released.
  • At least 10%, preferably at least 20%, more preferably at least 30%, even more preferably at least 40% or even at least 50%, in particular at least 60% or even at least 70% of the cells of these treated plant seeds have pores in the cell membrane.
  • the process according to the invention is particularly gentle and well suited for large-scale use. Treatment with electroporation (particularly PEF) significantly simplifies the subsequent depletion step without being too harsh. With the method according to the invention, edible plant seeds that meet the highest quality standards are produced without hesitation. In other words, the treated plant seeds are suitable for human consumption.
  • the method according to the invention is suitable for plant seeds that are whole or are intact ("whole seeds"), with a higher content of cyanogenic compounds, especially linseeds or stone fruit kernels, which have a higher content of cyanogenic compounds.
  • the content of cyanogenic compounds (in particular cyanogenic glycosides) in the plant seeds (in particular in the linseeds or stone fruit kernels) before depletion or in step a) of the process (in other words in the plant seeds provided) in such a way that more than 200 mg/kg, preferably more than 400 mg/kg, more preferably more than 600 mg/kg, even more preferably more than 800 mg/kg or even more than 1000 mg/kg, in particular more than 1200 mg/kg or even more than 1400 mg/kg (or even more than 2000 mg/kg kg) hydrogen cyanide can be released (preferably based on the dry mass of the plant seeds).
  • Electroporation is conventionally used in used in the food industry to preserve liquid foods; see . e.g. Toepfl, S., V. Heinz, and D. Knorr. "High intensity pulsed electric fields applied for food preservation.” Chemical engineering and processing: Process intensification 46.6 (2007): 537-546. Barba et al. (Barba, Francisco J., et al. "Current applications and new opportunities for the use of pulsed electric fields in food science and industry.” Food research international 77 (2015): 773-798.) contains an overview of the use of Pulsed Electric Fields in Food Technology. In Boussetta et al.
  • electroporation is suitable for the treatment of plant seeds in order to increase the effectiveness of the subsequent depletion of cyanogenic compounds.
  • the plant seeds Before being treated with electroporation, the plant seeds are usually soaked in an aqueous solution (e.g. tap water) (if necessary with mixing). This increases the efficiency of electroporation.
  • aqueous solution e.g. tap water
  • the aqueous solution can then be removed from the plant seeds, for example by filtering.
  • the depletion of the cyanogenic compounds can then be achieved, for example, by drying the plant seeds, because the converted hydrocyanic acid escapes. Particularly in the case of linseed, sufficiently low concentrations of cyanogenic compounds can be achieved.
  • the plant seeds are dried after electroporation or step c) includes Drying the plant seeds. Preferably, drying is carried out to a residual moisture content of less than 20% by weight, preferably less than 15% by weight, even more preferably less than 10% by weight or even less than 7.5% by weight, in particular less than 5% by weight.
  • the depletion step is carried out at least partially under vacuum in a preferred embodiment.
  • under vacuum in this (large-scale technical) context does not mean that an absolute vacuum is achieved, but only that negative pressure is generated to a considerable extent.
  • under vacuum should be understood as: that at times (e.g. at least 15 minutes, preferably at least 30 minutes, even more preferably at least 60 minutes, in particular at least 120 minutes or even at least 360 minutes) a pressure of 600 mbar, preferably 500 mbar, more preferably 400 mbar, even more preferably 350 mbar or even falls below 300 mbar.
  • step c) preferably comprises depleting cyanogenic compounds in a first vacuum stage and a second vacuum stage, the pressure of the first vacuum stage being higher than the pressure of the second vacuum stage.
  • the pressure of the first vacuum stage is preferably between 300 and 500 mbar.
  • the pressure of the second vacuum stage is preferably below 200 mbar, preferably below 150 mbar, in particular below 100 mbar.
  • step c) is at least partially carried out with heating (preferably so that a temperature between 30 ° C and 80 ° C is achieved). If several vacuum stages are used, the temperature during the first vacuum stage (preferably 30 ° C to 40 ° C) is expedient lower than during the second vacuum stage (preferably 40 ° C to 80 ° C). According to a further preferred embodiment, step c) is at least partially at more than 25 ° C, preferably more than 30 ° C, more preferably more than 35 ° C, even more preferably more than 40 ° C, in particular more than 45 ° C or even more than 50°C (at normal pressure or under vacuum).
  • step c) is carried out at least partially with mixing.
  • the plant seeds remain essentially intact (in particular bite-proof). In other words, they remain whole and are not chopped up (ground).
  • the plant seeds treated according to the invention are no longer capable of germinating (due to electroporation).
  • the content of cyanogenic compounds (in particular cyanogenic glycosides) in the plant seeds treated according to the invention is so low that less than 1000 mg/kg, preferably less than 800 mg/kg, more preferably less than 600 mg/kg , even more preferably less than 400 mg/kg or even less than 300 mg/kg, in particular less than 200 mg/kg or even less than 150 mg/kg prussic acid can be released (preferably based on the dry mass of the plant seeds).
  • the treated plant seeds have a residual content of cyanogenic compounds, so that in relation to the total mass of the treated plant seeds, more than 1 mg/kg or even more than 2 mg/kg, preferably more than 5 mg/kg or even more than 10 mg /kg, more preferably more than 20 mg/kg, even more preferably more than 50 mg/kg or even more than 75 mg/kg, in particular more than 100 mg/kg or even more than 125 mg/kg, hydrocyanic acid can be released ( preferably based on the dry mass of the plant seeds).
  • the The residual content of linseed is more than 50 mg/kg or more than 100 mg/kg.
  • the residual content can be more than 5 mg/kg or more than 10 mg/kg.
  • At least 10%, preferably at least 20%, more preferably at least 30%, even more preferably at least 40% or even at least 50%, in particular at least 60% or even at least 70% of the cells of the treated plant seeds pores in of the cell membrane are more suitable for further treatment steps (e.g. enriching with vitamins by temporarily placing them in vitamin solutions or leaching sugar from the seeds or treatment steps for which increased swelling capacity is useful).
  • the porous cells can usually be stained with propidium iodide (in other words, this makes successful electroporation detectable).
  • Propidium iodide is a DNA-intercalating dye that does not penetrate membranes in healthy cells.
  • the number of stained cells can then be determined, for example, using a fluorescence microscope, while the total number can be determined, for example, by counting in a light microscope.
  • the use of propidium iodide to detect electroporation is shown, for example, in Steuer, Anna. Effects of nanosecond pulsed electric fields on cells in the monolayer. Diss. University of Rostock, 2016 (in particular Section 2.5 “Detection of electroporation” on p. 24).
  • the treated plant seeds are usually in dry form. It is preferred that the treated plant seeds have a residual moisture content of less than 20% by weight, preferably less than 15% by weight, even more preferably less than 10% by weight or even less than 7.5% by weight, in particular less than 5% by weight.
  • Fig. 1 shows schematically an embodiment of the method according to the invention.
  • Fig. 2 shows schematically an embodiment of the depletion of cyanogenic compounds (i.e. step c).
  • Example 1 Electroporation and depletion of cyanogenic compounds in cherry stone seeds
  • Cherry stone seeds with an initial cyanide content of 1500 mg/kg are mixed with water in a ratio of 1:4 (w/w) (e.g. 300 g seeds and 1200 g water) and soaked at room temperature for 1 hour.
  • Dry substance raw material before soaking 94.32%, dry substance after soaking: 45%.
  • the swollen seeds are treated in a PEF treatment cell with the following parameters:
  • Treatment cell Batch - 9 cm electrode distance (parallel) Pulse shape: rectangular pulse
  • the treated seeds are then incubated for 2 hours at room temperature and then either dried for 2 hours at 50 ° C hot air in a drum dryer or for 19 hours at 50 ° C hot air in a drying cabinet (rack drying). This depletes cyanogenic compounds. (Alternatively or additionally, the depletion process shown schematically in FIG. 2 can also be used.)
  • FIG. 1 A simplified, schematic representation of the process is shown in Fig. 1.
  • Electroporated linseeds are mixed with water in a vacuum tank at a vacuum of 300-500 mbar and a temperature of 45°C (vacuum level 1). At this temperature-pressure combination, the cyanide can evaporate, but the water cannot. The process is continued until the desired amount of cyanide has been extracted (or the specified cyanide limit concentration, e.g. 150 mg/kg, has been undershot). The vacuum and temperature are then increased to evaporate the water (vacuum level 2). This is then collected in a capacitor. By separating the two phases, it can be ensured that the cyanide does not pass into the evaporated water, but can be separated separately.
  • the reactor is continuously purged with a non-reactive gas such as nitrogen to ensure better removal of HCN gas.
  • a non-reactive gas such as nitrogen
  • the process is ended.
  • the duration of vacuum level 1 is, for example, 2 hours, and that of vacuum level 2 is also 2 hours, for example.
  • the treated linseeds obtained after the depletion process are ideal for further use in the food and feed industry.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Botany (AREA)
  • Developmental Biology & Embryology (AREA)
  • Environmental Sciences (AREA)
  • Cultivation Of Plants (AREA)

Abstract

L'invention concerne un procédé de réduction de la teneur en composés cyanogéniques dans des semences végétales, comprenant les étapes consistant à : a) fournir des semences végétales, les semences végétales contenant des composés cyanogéniques, b) traiter les semences végétales par électroporation, en particulier un traitement par champ électrique pulsé (CEP), et c) réduire la teneur en composés cyanogéniques dans les semences végétales ainsi traitées. L'invention concerne également des semences végétales traitées pouvant être obtenues par ce procédé.
PCT/EP2023/056492 2022-03-14 2023-03-14 Procédé de réduction de la teneur en composés cyanogéniques dans des graines végétales Ceased WO2023174942A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP23711720.5A EP4492966A1 (fr) 2022-03-14 2023-03-14 Procédé de réduction de la teneur en composés cyanogéniques dans des graines végétales

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Application Number Priority Date Filing Date Title
AT501592022 2022-03-14
ATA50159/2022 2022-03-14

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WO2023174942A1 true WO2023174942A1 (fr) 2023-09-21

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Citations (8)

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CN110651947A (zh) * 2019-10-15 2020-01-07 承德顺天食品有限公司 苦杏仁脱苦的方法
CN210988069U (zh) 2019-08-28 2020-07-14 杭州耐雀生物科技有限公司 大型整体式亚麻籽仁脱毒罐
CN210988068U (zh) 2019-08-28 2020-07-14 杭州耐雀生物科技有限公司 低频超声波亚麻籽仁脱毒仪
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CN103416639A (zh) * 2013-08-23 2013-12-04 陕西师范大学 一种超声诱导苦杏仁快速脱苦的方法
CN105341629A (zh) 2015-11-11 2016-02-24 宜垦(天津)农业制品有限公司 一种面条用杏仁脱苦方法
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CN210988069U (zh) 2019-08-28 2020-07-14 杭州耐雀生物科技有限公司 大型整体式亚麻籽仁脱毒罐
CN210988068U (zh) 2019-08-28 2020-07-14 杭州耐雀生物科技有限公司 低频超声波亚麻籽仁脱毒仪
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WO2023275291A1 (fr) * 2021-06-30 2023-01-05 Kern Tec Gmbh Procédé de production d'un matériau de graine de plante ayant une teneur réduite en composés cyanogénétiques

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