WO2020240710A1 - Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes - Google Patents

Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes Download PDF

Info

Publication number
WO2020240710A1
WO2020240710A1 PCT/JP2019/021146 JP2019021146W WO2020240710A1 WO 2020240710 A1 WO2020240710 A1 WO 2020240710A1 JP 2019021146 W JP2019021146 W JP 2019021146W WO 2020240710 A1 WO2020240710 A1 WO 2020240710A1
Authority
WO
WIPO (PCT)
Prior art keywords
flavonoid
autoclave
flavonoids
pressure
raw material
Prior art date
Application number
PCT/JP2019/021146
Other languages
English (en)
Japanese (ja)
Inventor
征宏 有福
雅義 上面
大地 酒井
明嗣 下見
Original Assignee
昭和電工マテリアルズ株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 昭和電工マテリアルズ株式会社 filed Critical 昭和電工マテリアルズ株式会社
Priority to PCT/JP2019/021146 priority Critical patent/WO2020240710A1/fr
Priority to JP2021521633A priority patent/JP7264244B2/ja
Publication of WO2020240710A1 publication Critical patent/WO2020240710A1/fr

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones

Definitions

  • the present invention relates to a method for decomposing flavonoid glycosides and a method for producing flavonoids.
  • Flavonoids are a group of naturally occurring organic compounds, and are contained in flowers, leaves, roots, stems, fruits, seeds, etc. of various plants, including citrus fruits and legumes. Flavonoids have different characteristics and actions depending on the type, but most of them have a strong antioxidant action.
  • polymethoxyflavone which is a flavonoid contained in citrus fruits, is known to have an antioxidant effect, a carcinogenic inhibitory effect, an antibacterial effect, an antiviral effect, an antiallergic effect, a melanin production inhibitory effect, a blood glucose level suppressing effect, and the like. It is expected to be applied to various uses such as pharmaceuticals, health foods, and cosmetics.
  • the conventional flavonoid production method has a problem that the yield of flavonoids is low. Therefore, there is a need for the development of a production method capable of improving the yield of flavonoids.
  • the peel of citrus fruits contains a larger amount of flavonoid glycosides in addition to flavonoids, but if this can be recovered as flavonoids, the yield of flavonoids can be improved.
  • the method of decomposing flavonoid glycosides into flavonoids include a method of reacting flavonoid glycosides with an acid such as hydrochloric acid. However, this method has a problem that the used acid may remain and be mixed in the product, and a side reaction product of the acid and flavonoid may be generated.
  • Examples of the method for removing impurities such as acids and by-products include a method for separating and purifying flavonoids in decomposition products by liquid chromatography, but there are problems that the cost is high and the production efficiency is poor. Therefore, a new method for decomposing flavonoid glycosides without using an acid is required.
  • the present invention has been made in view of the above-mentioned problems of the prior art, and is a flavonoid glycoside capable of efficiently decomposing flavonoid glycosides into flavonoids without using an acid and improving the yield of flavonoids. It is an object of the present invention to provide a decomposition method and a method for producing flavonoids.
  • the present invention comprises a hydrothermal treatment step of decomposing the flavonoid glycosides into flavonoids by hydrothermally treating a raw material liquid containing flavonoid glycosides in an autoclave, and after the hydrothermal treatment step.
  • a method for decomposing flavonoid glycosides which comprises a depressurizing step of depressurizing the pressure in the autoclave at a depressurizing rate of 150 kPa / min or less.
  • flavonoid glycosides can be efficiently decomposed into flavonoids by hydrothermal treatment without using an acid. Further, by using this method, flavonoids can be efficiently produced at low cost.
  • the present inventors have found that in the method of decomposing flavonoid glycosides by hydrothermal treatment, a phenomenon occurs in which the raw material liquid suddenly boils and scatters when the pressure is reduced after the hydrothermal treatment.
  • the scattering of the raw material liquid is one of the causes of the decrease in the yield of flavonoids.
  • the present inventors have found that the yield of flavonoids can be greatly improved by depressurizing at a predetermined depressurizing rate during depressurization.
  • the bumping and scattering of the raw material liquid can be sufficiently suppressed, and the yield of flavonoids can be greatly improved. Can be done.
  • the above hydrothermal treatment may be performed by supplying steam from the outside into the above autoclave.
  • the temperature inside the autoclave can be raised and raised in a short time, and a hydrothermal treatment environment can be easily formed and maintained.
  • the pressure in the autoclave may be 0.2 to 1.6 MPa and the temperature may be 120 to 200 ° C.
  • the flavonoid glycoside may contain a sudachitin glycoside and / or a demethoxysudachitin glycoside. According to the above decomposition method, sudachitin glycosides and demethoxysudachitin glycosides can be decomposed particularly efficiently.
  • the present invention also comprises a method for producing flavonoids, which comprises a decomposition step of decomposing flavonoid glycosides by the decomposition method of the present invention and an extraction step of extracting flavonoids from the decomposition products obtained in the decomposition step. provide. According to such a production method, flavonoids can be produced in high yield, at low cost and efficiently.
  • a method for decomposing flavonoid glycosides which can efficiently decompose flavonoid glycosides into flavonoids without using an acid, and which can improve the yield of flavonoids, and a method for producing flavonoids. Can be done.
  • the numerical range indicated by using “-" indicates a range including the numerical values before and after "-" as the minimum value and the maximum value, respectively.
  • the upper limit value or the lower limit value of the numerical range of one step can be arbitrarily combined with the upper limit value or the lower limit value of the numerical range of another step.
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • “A or B” may include either A or B, or both.
  • the materials exemplified in the present specification may be used alone or in combination of two or more.
  • the method for decomposing flavonoid glycosides includes a hydrothermal treatment step of decomposing the flavonoid glycosides into flavonoids by hydrothermally treating a raw material solution containing the flavonoid glycosides in an autoclave, and the hydrothermal treatment. It has a decompression step of reducing the pressure in the autoclave after the step at a decompression rate of 150 kPa / min or less.
  • Flavonoid glycosides are hydrophilic compounds having a structure in which flavonoids and sugars are bound by glycosidic bonds. Flavonoids, which are the source of flavonoid glycosides, are aromatic compounds having a phenylchroman skeleton as a basic structure. Kind and the like. Among these, the flavonoid may be polymethoxyflavone, which is a flavon.
  • polymethoxyflavones examples include sudachitin, demethoxysudachitin, nobiletin, tangeretin, pentamethoxyflavones, tetramethoxyflavones, and heptamethoxyflavones.
  • the polymethoxyflavone may be sudachitin or demethoxysudachitin.
  • the sugar that is the source of the flavonoid glycoside is not particularly limited, and examples thereof include known sugars that can form a glycoside by binding to the flavonoid described above by a glycosidic bond.
  • the raw material liquid to be subjected to hydrothermal treatment is a raw material containing flavonoid glycosides dissolved or dispersed in water.
  • the raw material may contain components other than flavonoid glycosides. Examples of other components include flavonoids, water-soluble dietary fiber, poorly soluble dietary fiber, sugars and the like.
  • the raw material liquid may contain a solvent other than water. Examples of the solvent other than water include alcohol.
  • the content of flavonoid glycosides in the raw material is preferably 0.1% by mass or more, more preferably 0.25 to 30% by mass, and 0.5 to 0.5 to 30% by mass, based on the total solid content of the raw material. It is more preferably 5% by mass.
  • the content of flavonoid glycosides is preferably 0.25 parts by mass or more, preferably 0.5 to 100 parts by mass, based on 1 part by mass of the flavonoid content. Is more preferable, and 5 to 50 parts by mass is further preferable.
  • the concentration of the raw material in the raw material liquid is preferably 1 to 30% by mass, more preferably 3 to 20% by mass, and further preferably 5 to 10% by mass, based on the total amount of the raw material liquid. ..
  • concentration of the raw material is 1% by mass or more, the yield of decomposition products increases, so that the amount of flavonoids obtained by one decomposition treatment tends to increase.
  • concentration is 30% by mass or less, flavonoid glycosides tend to increase. There is a tendency that the decomposition of the above can be performed more reliably and efficiently.
  • the raw material may be a dry powder obtained from citrus fruits, or may be a dry powder obtained from the peel of citrus fruits.
  • citrus fruits include sudachi, satsuma mandarin, ponkan, and shikuwasa.
  • the citrus fruits may be sudachi containing a large amount of polymethoxyflavones such as sudachitin and demethoxysudachitin, and their glycosides.
  • Hydrothermal treatment can be performed by enclosing the raw material liquid in an autoclave and heating it at a temperature exceeding 100 ° C. while keeping it sealed. By heating the raw material liquid in the autoclave, the inside of the autoclave becomes a heating and pressurizing environment, and hydrothermal treatment (hydrothermal synthesis) is performed. The hydrothermal treatment may be performed while stirring the raw material liquid. Further, the hydrothermal treatment may be performed by supplying steam from the outside into the autoclave. For example, by supplying saturated steam at high temperature and high pressure into the autoclave, the inside of the autoclave becomes a heating and pressurizing environment, and hydrothermal treatment (hydrothermal synthesis) is performed.
  • the autoclave is not particularly limited, and may be either a vertical type or a horizontal type.
  • the raw material liquid may be directly filled in the tank, or the raw material liquid may be placed in a raw material container and placed on a table.
  • water may be put in the autoclave tank separately from the raw material liquid.
  • hydrothermal treatment can be performed by, for example, the following method.
  • FIG. 1 is a schematic cross-sectional view showing an example of an autoclave (horizontal circulation type autoclave) used in the above disassembly method.
  • a cylindrical muffle furnace 3 having both ends open is arranged in a cylindrical pressure vessel (tank) 2 provided with a door (sealed door) 1 that can be sealed at one end.
  • An air passage 4 is formed between the inner wall of the pressure vessel 2 and the outer wall of the muffle furnace 3.
  • one end of the muffle furnace 3 is connected to the circulation fan 8 via the cooler 6, the heater 5, and the air passage 9.
  • the circulation fan 8 is attached to a rotating shaft of a motor 7 arranged outside the end of the pressure vessel 2 on the opposite side of the closed door 1.
  • a movable table 12 is arranged inside the muffle furnace 3, and a raw material container 11 filled with the raw material liquid 10 is placed on the movable table 12.
  • a boiler 13 for supplying steam is connected to the pressure vessel 2 via a pipe provided with a valve 14. Further, a pipe provided with a pressure gauge 15 and a pressure valve 16 is connected to the pressure vessel 2 in order to adjust the internal pressure.
  • the raw material container 11 is not particularly limited as long as it can withstand the temperature and pressure during hydrothermal treatment and the amount of impurities mixed in the raw material liquid 10 is small.
  • a metal such as stainless steel, titanium and an alloy thereof, or a metal such as an alloy thereof, or
  • a tank-shaped container made of a resin such as polytetrafluoroethylene, a bottle-shaped container, a cup-shaped container, a tray-shaped container, or a drum-shaped container can be used.
  • at least the inner surface of the container may be coated with a chemically stable material having heat resistance and pressure resistance such as enamel and polytetrafluoroethylene.
  • the steam supplied from the boiler 13 into the pressure vessel 2 circulates in the autoclave 100 along the arrow in FIG. That is, the water vapor is sent out to the air passage 4 by the circulation fan 8 and heads for the closed door 1, then flows into the muffle furnace 3 and flows around the raw material container 11, and passes through the cooler 6, the heater 5, and the air passage 9. It is sucked by the circulation fan 8 and sent out to the air passage 4 again.
  • the amount of water vapor supplied is adjusted by operating the valve 14 so that the inside of the autoclave 100 has a predetermined temperature and pressure.
  • the temperature inside the autoclave 100 may be adjusted by the heater 5 and the cooler 6. Further, the pressure in the autoclave 100 may be adjusted by opening and closing the pressure valve 16.
  • the reaction conditions of the hydrothermal treatment are not particularly limited, but can be, for example, 0.5 to 20 hours at 110 to 300 ° C.
  • the reaction temperature is preferably 120 to 200 ° C., more preferably 120 to 190 ° C., and even more preferably 140 to 185 ° C.
  • the reaction time is preferably 0.5 to 20 hours, more preferably 1 to 10 hours. When the reaction time is 0.5 hours or more, the reaction tends to proceed more easily, and when the reaction time is 20 hours or less, the progress of the reaction and the cost tend to be easily balanced.
  • the pressure in the autoclave during hydrothermal treatment may be the saturated vapor pressure corresponding to the above reaction temperature or higher, but it is preferably the saturated vapor pressure from the viewpoint of the pressure resistance of the apparatus.
  • the pressure in the autoclave during the hydrothermal treatment can be, for example, 0.2 to 1.6 MPa.
  • flavonoid glycosides can be efficiently decomposed into flavonoids (more specifically, flavonoids and sugars).
  • a depressurizing step of reducing the pressure in the autoclave at a depressurizing rate of 150 kPa / min or less is performed.
  • the depressurization in the autoclave can be performed by opening the pressure valve and discharging the water vapor in the autoclave.
  • the decompression rate at the time of depressurization can be adjusted with a pressure valve. It is preferable to reduce the pressure while checking the pressure in the autoclave with a pressure gauge.
  • the depressurization rate is preferably 100 kPa / min or less, more preferably 50 kPa / min or less, further preferably 30 kPa / min or less, and 20 kPa / min. Minutes or less is particularly preferable, and 10 kPa / min or less is extremely preferable.
  • the lower limit of the depressurization rate is not particularly limited, but may be 1 kPa / min or more or 5 kPa / min or more from the viewpoint of shortening the time required for the decompression step.
  • the depressurizing rate does not have to be constant at all times, and the depressurizing rate may be varied as long as it is within the range of 150 kPa / min or less.
  • the temperature inside the autoclave will also decrease as the pressure is reduced due to the discharge of water vapor from the autoclave.
  • the temperature around the raw material container is lowered, and the raw material liquid boils and gradually volatilizes, and the liquid temperature of the raw material liquid also follows the ambient temperature.
  • the pressure in the autoclave is maintained above the saturated vapor pressure, it is possible to prevent the raw material liquid from becoming overheated, and it is possible to prevent bumping.
  • the pressure may be reduced while cooling the inside of the autoclave with a cooler.
  • the raw material liquid After depressurizing the inside of the autoclave to atmospheric pressure (0.1 MPa) by the above decompression step, the raw material liquid can be cooled to room temperature by natural cooling. Thereby, a decomposition product of flavonoid glycoside (glycoside decomposition product) can be obtained.
  • the method for producing flavonoids according to the present embodiment includes a decomposition step of decomposing flavonoid glycosides and an extraction step of extracting flavonoids from the decomposition products obtained in the decomposition step.
  • the decomposition step is a step of decomposing the flavonoid glycoside by the method for decomposing the flavonoid glycoside according to the present embodiment described above.
  • flavonoids are extracted from the decomposition products obtained in the decomposition process.
  • the decomposition products include sugars, flavonoid glycosides remaining without decomposition, water-soluble and sparingly soluble celluloses, and decomposition products thereof.
  • flavonoids are hydrophobic, whereas sugars, flavonoid glycosides, water-soluble celluloses and their decomposition products are hydrophilic. Therefore, flavonoids are contained in a high concentration in the components insoluble in the aqueous solution after the hydrothermal treatment, and the flavonoids can be concentrated by separating the aqueous solution and the insoluble matter after the hydrothermal treatment.
  • the water-insoluble component is further dissolved in a solvent that dissolves the flavonoid, for example, ethanol, ethyl acetate, hexane, toluene, etc., and a mixed solvent thereof, and the insoluble matter is removed by filtration or the like to further extract the flavonoid.
  • a solvent that dissolves the flavonoid for example, ethanol, ethyl acetate, hexane, toluene, etc.
  • a mixed solvent thereof for example, ethanol, ethyl acetate, hexane, toluene, etc.
  • the insoluble matter is removed by filtration or the like to further extract the flavonoid.
  • a high-concentration flavonoid can be obtained.
  • flavonoids can be efficiently produced in high yield.
  • the flavonoid produced by the production method of the present embodiment may be polymethoxyflavone, sudachitin and / or demethoxysudachitin.
  • the production method of the present embodiment is suitable for producing polymethoxyflavones, particularly sudachitin and demethoxysudachitin, and the yield thereof can be greatly improved.
  • the autoclave 100 shown in FIG. 1 includes one circulation fan 8, but an autoclave including a plurality of circulation fans may be used.
  • circulation fans when circulation fans are installed at a plurality of locations in the muffle furnace 3, the temperature in the muffle furnace 3 is likely to be uniform, and even when a plurality of raw material liquids are accommodated, the temperature of each raw material liquid is likely to be uniform. ..
  • the autoclave 100 shown in FIG. 1 includes a cooler 6 and a heater 5, but one or both of them may not be provided.
  • Example 1 Sudachi peel extract powder (manufactured by Ikeda Yakuso Co., Ltd.), which has a sudachitin content of 1000 mass ppm and a sugar-derived sudachitin content of 9000 mass ppm, is dissolved / dispersed in ultrapure water so as to have a content of 5 mass%.
  • An aqueous dispersion was prepared. 15L stainless steel tank (manufactured by Nitto Metal Industry Co., Ltd., container depth: 27 cm) and 1L polytetrafluoroethylene (PTFE) bottle (manufactured by AS ONE Corporation, trade name: Big Boy wide mouth 1000 ml, container depth 20 cm) ), The predetermined amount shown in Table 1 was added.
  • PTFE polytetrafluoroethylene
  • Samples 1 to 3 shown in Table 1 were housed in a circulating hot air autoclave intracisternal volume 2m 3 (KK Ashida Seisakusho), 1 hour, glycoside decomposing sudachi peel extract aqueous dispersion at 180 ° C. did.
  • saturated steam at 180 ° C is supplied from the boiler into the tank (pressure vessel) of the autoclave, and the amount of steam supplied and the pressure valve so that the pressure in the tank becomes 1 MPa, which is the saturated steam pressure of water at 180 ° C. I went while adjusting.
  • the pressure valve from the tank pressure of 1 MPa (tank temperature 180 ° C) to 0.1 MPa (tank temperature 100 ° C), which is the saturated water vapor pressure at 100 ° C of water, at a decompression rate of 7.5 kPa / min. was adjusted to reduce the pressure and lower the temperature.
  • the time required for decompression was 2 hours.
  • the lid of the tank was opened, the containers (samples 1 to 3) were taken out, and the container was naturally cooled to room temperature (25 ° C.).
  • the solution and solid content in each container are depressurized using a diaphragm pump using a 0.2 ⁇ m hydrophilic PTFE membrane filter (Merck-Millipore, trade name: Omnipore 0.2 ⁇ m JG). It was filtered.
  • the separated solution contains the decomposed sugars derived from glycosides, and the solids contain a high concentration of decomposed sudachitin. Therefore, the obtained solids are put into a 200 cc glass beaker. It was put in and dried in an oven at 120 ° C. for 5 hours to obtain a powdery glycoside decomposition product. Next, the glycoside decomposition product was dispersed in ethanol to prepare a 5% by mass dispersion, and treated at 60 ° C.
  • the dispersion is filtered under reduced pressure using a diaphragm pump using a hydrophilic PTFE membrane filter (Merck-Millipore, trade name: Omnipore 0.2 ⁇ m JG) with a mesh opening of 0.2 ⁇ m, and the sudachitin solution is dissolved.
  • a hydrophilic PTFE membrane filter Merck-Millipore, trade name: Omnipore 0.2 ⁇ m JG
  • Got The sudachitin solution was vacuum dried using a diaphragm pump under heating at 60 ° C. to obtain a powdered sudachitin concentrated powder.
  • Example 2 Glycoside decomposition products and sudachitin concentrated powder were obtained in the same manner as in Example 1 except that the depressurization rate after the decomposition treatment was changed to the conditions shown in Table 2.
  • the yield of sudachitin was determined from the mass of the sudachitin concentrated powder and the sudachitin concentration. The yield indicates the ratio of the mass of sudachitin contained in the obtained concentrated sudachitin powder to the total mass of sudachitin and glycoside-derived sudachitin in the sample before the decomposition treatment. The results are shown in Table 2.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention concerne un procédé de dégradation de glycosides de flavonoïdes comprenant : une étape de traitement hydrothermique pour dégrader des glycosides de flavonoïdes en flavonoïdes par réalisation, dans un autoclave, d'un traitement hydrothermique d'une solution de matière première contenant des glycosides de flavonoïdes; et une étape de décompression pour abaisser la pression à l'intérieur de l'autoclave après l'étape de traitement hydrothermique à une vitesse de décompression n'excédant pas 150 kPa/min.
PCT/JP2019/021146 2019-05-28 2019-05-28 Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes WO2020240710A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/JP2019/021146 WO2020240710A1 (fr) 2019-05-28 2019-05-28 Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes
JP2021521633A JP7264244B2 (ja) 2019-05-28 2019-05-28 フラボノイド配糖体の分解方法及びフラボノイドの製造方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2019/021146 WO2020240710A1 (fr) 2019-05-28 2019-05-28 Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes

Publications (1)

Publication Number Publication Date
WO2020240710A1 true WO2020240710A1 (fr) 2020-12-03

Family

ID=73552856

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/021146 WO2020240710A1 (fr) 2019-05-28 2019-05-28 Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes

Country Status (2)

Country Link
JP (1) JP7264244B2 (fr)
WO (1) WO2020240710A1 (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008155890A1 (fr) * 2007-06-21 2008-12-24 J-Oil Mills, Inc. Procédé de production d'un aglycone de glycoside.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008155890A1 (fr) * 2007-06-21 2008-12-24 J-Oil Mills, Inc. Procédé de production d'un aglycone de glycoside.

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LI-JUAN DU, QING-HAN GAO, XIAO-LONG JI, YU-JIE MA, FANG-YI XU, MIN WANG: "Comparison of Flavonoids, Phenolic Acids, and Antioxidant Activity of Explosion-Puffed and Sun-Dried Jujubes ( Ziziphus jujuba Mill.)", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 61, no. 48, 2013, pages 11840 - 11847, XP055763900 *

Also Published As

Publication number Publication date
JP7264244B2 (ja) 2023-04-25
JPWO2020240710A1 (fr) 2020-12-03

Similar Documents

Publication Publication Date Title
Rivas et al. Functional properties of extracts and residual dietary fibre from pomegranate (Punica granatum L.) peel obtained with different supercritical fluid conditions
Both et al. Mass transfer enhancement for solid–liquid extractions
US7109384B2 (en) Process to extract phenolic compounds from a residual plant material using a hydrothermal treatment
Velisdeh et al. Optimization of sequential microwave-ultrasound-assisted extraction for maximum recovery of quercetin and total flavonoids from red onion (Allium cepa L.) skin wastes
KR100509787B1 (ko) 마늘유의 추출 방법
WO2020240710A1 (fr) Procédé de dégradation de glycosides de flavonoïdes et procédé de production de flavonoïdes
Liza et al. Supercritical fluid extraction of bioactive flavonoid from Strobilanthes crispus (pecah kaca) and its comparison with solvent extraction.
JP7383906B2 (ja) フラボノイド配糖体の分解方法及びフラボノイドの製造方法
WO2020240705A1 (fr) Procédé de dégradation de glycoside de flavonoïde, procédé de production de flavonoïde et procédé de refroidissement d'une solution dans un autoclave
US11884641B2 (en) Method for decomposing flavonoid glycoside and method for producing flavonoid
Săvescu et al. Healthy food-obtained through innovative technologies.
KR102127278B1 (ko) 꽃송이버섯 추출물 제조방법
JP7419673B2 (ja) フラボノイド配糖体の分解方法及びフラボノイドの製造方法
WO2022070418A1 (fr) Procédé de dégradation de flavonoïde glycoside et procédé de production de flavonoïde
JP2020193168A (ja) フラボノイド配糖体の分解方法及びフラボノイドの製造方法
KR20060093145A (ko) 초임계유체 추출공정을 이용한 포도씨기름의 제조 방법
TWI835827B (zh) 類黃酮苷的分解方法和類黃酮的製造方法
JP2021116288A (ja) 配糖体の分解方法及びアグリコンの製造方法
JP2020193171A (ja) フラボノイド配糖体の分解方法及びフラボノイドの製造方法
WO2020022509A1 (fr) Procédé de décomposition de flavonoïde glycoside et procédé de production de flavonoïde
JP6527744B2 (ja) ニンジン抽出物の製造方法
WO2020090813A1 (fr) Procédé de production de flavonoïde
JP2021116286A (ja) エステル化合物の分解方法及びヒドロシキル基を有する化合物の製造方法
Dinesha et al. Effect of supercritical carbon dioxide conditions on extraction of food phytochemical constituents from Moringa oleifera. Lam seed kernels
JP2021116289A (ja) 配糖体の分解方法及びアグリコン濃縮物の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19930845

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021521633

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

32PN Ep: public notification in the ep bulletin as address of the adressee cannot be established

Free format text: NOTING OF LOSS OF RIGHTS PURSUANT TO RULE 112(1) EPC (EPO FORM 1205A DATED 11.03.2022)

122 Ep: pct application non-entry in european phase

Ref document number: 19930845

Country of ref document: EP

Kind code of ref document: A1