WO2011059311A2 - Production of natural ubiquinone and ubiquinol by extraction from palm plant - Google Patents
Production of natural ubiquinone and ubiquinol by extraction from palm plant Download PDFInfo
- Publication number
- WO2011059311A2 WO2011059311A2 PCT/MY2010/000282 MY2010000282W WO2011059311A2 WO 2011059311 A2 WO2011059311 A2 WO 2011059311A2 MY 2010000282 W MY2010000282 W MY 2010000282W WO 2011059311 A2 WO2011059311 A2 WO 2011059311A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- palm
- coenzyme
- extraction solution
- source
- oil
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/008—Refining fats or fatty oils by filtration, e.g. including ultra filtration, dialysis
Definitions
- the present invention relates to extraction of natural ubiquinone and ubiquinol from palm plant, including parts thereof, in particular from palm oil and palm pressed fiber.
- Coenzyme Q10 (sometimes referred to as CoQlO) is a 1.4-benzoquinone where Q refers to the quinone chemical group, and 10 refers to the isoprenyl chemical subunits.
- CoQlO is a kind of fat-soluble quinine, crystallizes at room temperature, has a melting point of 48 degrees Centigrade and has a structure like that of Vitamin K because of the side chain of mother of six core (named for the polymerizational degree of polyisoprene-based) is 10.
- the physiological function of CoQlO is mainly from the redox properties of its quinine-based component and the physical properties of its isoprenoid side chain.
- CoQlO has mainly two functions, one is anti-lipid oxidation, another is its important role during generation of energy in the mitochondria.
- the quinone ring plays a role of transferring electrons and protons in the oxidation of the respiratory chain. This function is necessary not only for all life forms, but also the key to form ATP.
- CoQlO is a component of the electron transport chain and participates in aerobic cellular respiration generating energy in the form of ATP. 95% of the human body's energy is generated this way. Therefore, those organs with the highest energy requirements such as the heart and the liver have the highest CoQlO concentrations.
- CoQlO is a natural antioxidant and metabolic activator of cells, having the functions of protecting and recovering the integrity of bio film structure, and stabilizing membrane potential. It is an enhancer of body non-specific immunity. At present, CoQlO is used for the treatment of clinical heart disease, hepatitis and a number of other diseases. The health benefits of CoQlO have led to increased commercial importance of this compound, which is useful as a food, nutritional product, nutritional supplement, animal drug, drink, feed, cosmetic, pharmaceutical product, therapeutic drug, or prophylactic drug. CoQIO may exist in the oxidized or reduced form. Ubiquinol is the reduced form of the Co Q 10 supplement that has been on the market for many years.
- the substance Co Q 10 is a critical component of human metabolism and a dynamic nutrient that moves between two states, the oxidized ubiquinone, and the reduced ubiquinol. While in the ubiquinol state, its ability to be assimilated into the human body is increased, and it develops the additional feature of being a first class antioxidant.
- Reduced coenzyme Q10 is particularly beneficial for the older age group as the capacity for reduction in organisms is progressively reduced as the age of the organisms increases. Furthermore, certain products such as cosmetics, toothpaste, topical skin cream etc can only effectively achieve their purposes if the coenzyme Q10 is in its reduced form.
- Reduced coenzyme Q10 is the second electronic reducing body of oxidized coenzyme Q10.
- Using a chemical reductant can reduce the oxidized coenzyme Q10 to reduced coenzyme QlO.However, there exists some problems of molecular oxidation when using the reduced coenzyme Q10, that is produced by the chemical reductant, in products such as health food, beverages, cosmetics and drugs. Furthermore, the use of chemical reductants may contaminate said products and cannot guarantee safety of the body.
- CoQlO can also be produced by fermentation using microorganisms.
- currently known methods of producing CoQlO often do not produce naturally occurring CoQlO but instead involve manipulation by genetic engineering or gene transformation.
- European patent EP 1 123 979 Al disclosed production of CoQlO with improved efficiency by transforming E. coli with an expression vector comprising DNA coding for decaprenyl diphosphate synthase from a fungal strain of the genus Saitoella.
- Patent Cooperation Treaty (PCT) WO 02/099095 A2 disclosed a method for engineering a bacterium, particularly of the genus Paracoccus, to produce an isoprenoid compound, particularly zeaxanthin, by overexpressing genes of the mevalonate pathway.
- Rhodobacter sphaeroides The gram-negative bacterium Rhodobacter sphaeroides is a natural producer of CoQl O, and as such has been attempted to be developed for industrial production of CoQlO.
- Yoshida et al. J. Gen. Appl. Microbiol. 44, 19-26, 1998) described the influence of aeration on CoQlO production and the isolation of non-recombinant mutants of R.
- EP 1 227 155 A 1 disclosed the increased production of CoQlO by microorganisms which are capable of producing this compound, inter alia of the genus Rhodobacter.
- the increase in CoQlO production is achieved by introducing into the microorganisms one or more properties selected from the group consisting of reduced or defective
- USPC Class: 424 941 disclosed a method for the production of CoQ.sub. lO in a recombinant oleaginous yeast, yeast host cell with at least one copy of a genetic construct encoding decaprenyl diphosphate synthase; and culturing the transformed yeast cells, whereby the decaprenyl diphosphate synthase is expressed and whereby CoQlO is produced.
- WO 02/26933 Al disclosed methods for increasing the production of CoQlO in
- Rhodobacter sphaeroides by overexpressing a few heterologous genes coding for some of the enzymes wherein over expression of these genes resulted in only very modest improvement in CoQ 10 production.
- Palm oil is known to have nutrients, such as the carotenes and vitamin E.
- CoQlO is known to be present in various palm oil products, including palm oil and palm fibre oil. Measurement with authentic standard shows 10-80 ppm coenzyme Q10 in palm plant and 1000-1500 ppm in palm pressed fiber.
- Table 1 shows the CoQlO in various palm oil products:
- the present invention attempts to solve some of the above-discussed problems by extraction of natural CoQlO from palm plant particularly from palm pressed fiber; the plants need not be genetically engineered, fermentation is not needed to produce the CoQIO as the CoQIO is naturally produced by the palm plants, and furthermore, there is no necessity to use any chemical reductants and/or any added protective agents etc.
- a method of extracting one or both of oxidized coenzyme QIO and reduced coenzymeQIO from palm plant said method involving the following steps:
- citrate and its salts solution preferably at a concentration of 0.2-15% into a suitable extraction solution which can extract oxidized coenzyme QIO and or reduced coenzymeQIO from palm oil, palm pressed fiber and or any other parts or sources of the palm plant, and maintenance of the temperature preferably at about 4-50°C for preferably 12-48 hours;
- step (3) Preferably addition of an alkaline solution into the extraction solution separated out in step (2) to obtain a pH of 3.5-9.3 and maintenance of a temperature of 28-50°C;
- a preferred alkaline solution in step (3) above is NaOH solution.
- the concentration of oxidized coenzyme Q10 obtained in the present invention may be 0.2ug-4mg/ml and that of reduced coenzyme Q10 may be 0.3-3mg/ml.
- the extraction solution containing the oxidized and or reduced coenzyme Q10 may be dried to separate out the coenzyme Q10 from the extraction solution, and the coenzyme Q10 may then be freeze-dried.
- crystals of coenzyme Q10 obtained may all be reduced coenzyme QIO.
- the purity of the crystallization of reduced coenzyme QIO may be above 90.00%-99.00%.
- the extraction solution of step (1) preferably comprises 5-40% hexane.
- sources of the palm plant may include
- the coenzyme QlO/reduced coenzyme QIO produced by palm oil and palm pressed fiber is estimated to be around 20-40% oxidized coenzyme Q10 and 60- 80% reduced coenzyme Q10.
- the palm plant is preferably a naturally occurring plant.
- coenzyme Q10 produced by any one of the methods described above.
- Extraction solution (40% hexane and 25mM citrate solution, or 300ml 25% citrate solution), pH7.4 is put into a 10L tank. The said solution in the tank is sterilized by heating for 10 minutes at 121°C.
- Palm pressed fibre is washed twice with water. The mixture of water and palm fibre is filtered, and the waste water is discarded. The residue (180g wet objects) is collected. The wet objects are then placed in a Mulitibeads shocker-B300 for one hour to break the palm fibre to concussion moss. The broken palm fibre is then collected.
- Extraction solution (40% hexane and 25mM citrate solution), pH7.4 is put into a 10L tank. The said solution in the tank is sterilized by heating for 10 minutes at 121°C.
- Palm pressed fibre is washed twice with water. The waste water is then discarded by filtration. The residue (wet objects) is collected. Dry palm fiber may then be obtained by spray drying of the wet objects.
- the mixture is then centrifuged and the liquid part (the supernatant) is collected. Another 5L of the extraction solution is added to the precipitate obtained from the centrifugation. The mixture is again stirred for 30 minutes at 50 degrees Centigrade, and then centrifuged.
- the supernatants (the liquid part) obtained from both centrifugations above are collected (optionally by filtration).
- a sample analysed by HPLC shows that it contains 20% ubiquinone and 80% ubiquinol .
- 25g of FeC13 may be added to the liquids.
- the liquids are cooled to 4 degrees Centigrade for more than 10 hours to obtain crystallization of reduced CoQIO.
- Ethanol may be used to cool to 10 degrees Centigrade for 10 hours. Crystallization purity is 99% ubiquinol when 25g of FeC13 is added.
- Another option would be to subject the extraction liquids or crystals to chromatography, in which case 98% ubiquinol would be obtained.
- the crystals may be crushed and then packaged.
- Oxidized coenzyme QIO can be separated out by using agents such as Sephadex 4B.
- a large quantity of pharmaceutical grade coenzyme QlO/reduced coenzyme QIO which is natural, stable, non-genetically modified, can be obtained from palm fiber and other parts of the palm plant at a purity of 99.00%.
- the said coenzyme Q10 does not contain material from any other organisms and has no allergens to the human body.
- the coenzyme Q10 produced is safe, reliable, and can be used for medicine practical production.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention relates to a novel method for extracting natural ubiquinone and ubiquinol from palm plant.
Description
PRODUCTION OF NATURAL UBIQUINONE AND UBIQUINOL BY
EXTRACTION FROM PALM PLANT
Field of Invention
The present invention relates to extraction of natural ubiquinone and ubiquinol from palm plant, including parts thereof, in particular from palm oil and palm pressed fiber.
Background
Coenzyme Q10 (sometimes referred to as CoQlO) is a 1.4-benzoquinone where Q refers to the quinone chemical group, and 10 refers to the isoprenyl chemical subunits. CoQlO is a kind of fat-soluble quinine, crystallizes at room temperature, has a melting point of 48 degrees Centigrade and has a structure like that of Vitamin K because of the side chain of mother of six core (named for the polymerizational degree of polyisoprene-based) is 10. The physiological function of CoQlO is mainly from the redox properties of its quinine-based component and the physical properties of its isoprenoid side chain. This oil-soluble vitamin like substance is present in most eukaryotic cells, primarily in the mitochondria. CoQlO has mainly two functions, one is anti-lipid oxidation, another is its important role during generation of energy in the mitochondria. The quinone ring plays a role of transferring electrons and protons in the oxidation of the respiratory chain. This function is necessary not only for all life forms, but also the key to form ATP. CoQlO is a component of the electron transport chain and participates in aerobic cellular respiration generating energy in the form of ATP. 95% of the human body's energy is generated this way. Therefore, those organs with the highest energy requirements such as the heart and the liver have the highest CoQlO concentrations.
CoQlO is a natural antioxidant and metabolic activator of cells, having the functions of protecting and recovering the integrity of bio film structure, and stabilizing membrane potential. It is an enhancer of body non-specific immunity. At present, CoQlO is used for the treatment of clinical heart disease, hepatitis and a number of other diseases. The health benefits of CoQlO have led to increased commercial importance of this compound,
which is useful as a food, nutritional product, nutritional supplement, animal drug, drink, feed, cosmetic, pharmaceutical product, therapeutic drug, or prophylactic drug. CoQIO may exist in the oxidized or reduced form. Ubiquinol is the reduced form of the Co Q 10 supplement that has been on the market for many years. The substance Co Q 10 is a critical component of human metabolism and a dynamic nutrient that moves between two states, the oxidized ubiquinone, and the reduced ubiquinol. While in the ubiquinol state, its ability to be assimilated into the human body is increased, and it develops the additional feature of being a first class antioxidant.
In the healthy body, 97% is reduced coenzyme Q10, another 3% is oxidized coenzyme Q10. The reducibility of coenzyme Q10 has played the two important roles mentioned above. There is therefore a need for commercial mass production of reduced coenzyme Q10, particularly the natural form. After the oxidized coenzyme Q10 enters into the body, it would need the reductase to transform it again into reduced coenzyme Q10, which can then be used for beneficial purposes. Therefore, the reduced form of coenzyme Q10 has a more direct function than its oxidized form, in the metabolism of the body. In recent years, there have been reports pointing out that compared with the oxidized form, the reduced form of coenzyme Q10 has eighty times higher absorption or higher
bioavailability in the body. Thus to attain the same level in the body, a much smaller dose of reduced coenzyme Q10 than its oxidized form can be used.
Reduced coenzyme Q10 is particularly beneficial for the older age group as the capacity for reduction in organisms is progressively reduced as the age of the organisms increases. Furthermore, certain products such as cosmetics, toothpaste, topical skin cream etc can only effectively achieve their purposes if the coenzyme Q10 is in its reduced form.
Currently such products in the market contain the oxidized form of coenzyme Q10 which will be reduced only after entering the skin cells. Thus the coenzyme Q10 can only play its role after entering the skin cells and is therefore not effective.
However, reduced coenzyme Q10 can be easily oxidated by molecular oxygen; this is therefore a problem in the industrial production of reduced coenzyme Q10. It would thus appear that in order to maintain natural reduced coenzyme Q10 in its natural molecular state, the organisms producing the coenzyme Q10 themselves would be needed.
Reduced coenzyme Q10 is the second electronic reducing body of oxidized coenzyme Q10. Using a chemical reductant can reduce the oxidized coenzyme Q10 to reduced coenzyme QlO.However, there exists some problems of molecular oxidation when using the reduced coenzyme Q10, that is produced by the chemical reductant, in products such as health food, beverages, cosmetics and drugs. Furthermore, the use of chemical reductants may contaminate said products and cannot guarantee safety of the body.
Current methods of producing reduced coenzyme Q10 on a large scale involving the use of protective agents (to prevent or minimize molecular oxidation) and/or organic solvents also pose problems in that they incur the risk of contamination and hazards to human and the environment.
CoQlO can also be produced by fermentation using microorganisms. However, currently known methods of producing CoQlO often do not produce naturally occurring CoQlO but instead involve manipulation by genetic engineering or gene transformation.
For example, in European patent EP 1 070 759 Al A, a process for producing CoQlO involving transformation of a host microorganism, especially E. coli, with DNA coding for a protein having decaprenyl diphosphate synthase activity from the genus
Agrobacterium and culturing of the transformed organism, was disclosed.
European patent EP 1 123 979 Al disclosed production of CoQlO with improved efficiency by transforming E. coli with an expression vector comprising DNA coding for decaprenyl diphosphate synthase from a fungal strain of the genus Saitoella.
Patent Cooperation Treaty (PCT) WO 02/099095 A2 disclosed a method for engineering
a bacterium, particularly of the genus Paracoccus, to produce an isoprenoid compound, particularly zeaxanthin, by overexpressing genes of the mevalonate pathway.
The gram-negative bacterium Rhodobacter sphaeroides is a natural producer of CoQl O, and as such has been attempted to be developed for industrial production of CoQlO. Yoshida et al. (J. Gen. Appl. Microbiol. 44, 19-26, 1998) described the influence of aeration on CoQlO production and the isolation of non-recombinant mutants of R.
sphaeroides that had increased CoQl O content, and Sakato et al. (Biotechnol. Appl. Biochem. 16, 19-28, 1992) described methods for increasing CoQlO production in non- recombinant mutants of R. sphaeroides by optimizing the culture (fermentation) conditions. More recently, molecular genetic techniques have been applied to increase production of CoQlO by R. sphaeroides, yeast.
EP 1 227 155 A 1 disclosed the increased production of CoQlO by microorganisms which are capable of producing this compound, inter alia of the genus Rhodobacter. The increase in CoQlO production is achieved by introducing into the microorganisms one or more properties selected from the group consisting of reduced or defective
geranylgeranyl transferase activity, strengthened decaprenyldiphosphate synthetase and strengthened p-hydroxybenzoic acid decaprenyl transferase activity.
USPC Class: 424 941 disclosed a method for the production of CoQ.sub. lO in a recombinant oleaginous yeast, yeast host cell with at least one copy of a genetic construct encoding decaprenyl diphosphate synthase; and culturing the transformed yeast cells, whereby the decaprenyl diphosphate synthase is expressed and whereby CoQlO is produced.
WO 02/26933 Al disclosed methods for increasing the production of CoQlO in
Rhodobacter sphaeroides by overexpressing a few heterologous genes coding for some of the enzymes wherein over expression of these genes resulted in only very modest improvement in CoQ 10 production.
Palm oil is known to have nutrients, such as the carotenes and vitamin E. CoQlO is known to be present in various palm oil products, including palm oil and palm fibre oil. Measurement with authentic standard shows 10-80 ppm coenzyme Q10 in palm plant and 1000-1500 ppm in palm pressed fiber.
. .
Table 1 shows the CoQlO in various palm oil products:
TABLE 1. COQ10 IN PALM OIL PRODUCTS (PPM=parts per million) PALM OIL COQIO(PPM)
Crude palm oil 10-80
B leached p aim oil 10-70
RBD palm oil 10-30
RBD palm olein oil 10-20 Residual fibre oil 5-10
Commercial red palm olein 18-25
Palm plant (palm oil) 1000- 1500
Palm pressed fiber 1000- 1200
Source: Hamid and Choo.(2000)
Jun xiong (2009) The present invention attempts to solve some of the above-discussed problems by extraction of natural CoQlO from palm plant particularly from palm pressed fiber; the
plants need not be genetically engineered, fermentation is not needed to produce the CoQIO as the CoQIO is naturally produced by the palm plants, and furthermore, there is no necessity to use any chemical reductants and/or any added protective agents etc.
Summary of the Invention
According to one aspect of the present invention, there is provided a method of extracting one or both of oxidized coenzyme QIO and reduced coenzymeQIO from palm plant, said method involving the following steps:
(1) Addition of citrate and its salts solution preferably at a concentration of 0.2-15% into a suitable extraction solution which can extract oxidized coenzyme QIO and or reduced coenzymeQIO from palm oil, palm pressed fiber and or any other parts or sources of the palm plant, and maintenance of the temperature preferably at about 4-50°C for preferably 12-48 hours;
(2) Separation of the extraction solution of step (1);
(3) Preferably addition of an alkaline solution into the extraction solution separated out in step (2) to obtain a pH of 3.5-9.3 and maintenance of a temperature of 28-50°C;
(4) Removal of coenzyme QIO and or reduced coenzyme QIO from the solution of step (3).
A preferred alkaline solution in step (3) above is NaOH solution.
The concentration of oxidized coenzyme Q10 obtained in the present invention may be 0.2ug-4mg/ml and that of reduced coenzyme Q10 may be 0.3-3mg/ml.
The extraction solution containing the oxidized and or reduced coenzyme Q10 may be dried to separate out the coenzyme Q10 from the extraction solution, and the coenzyme Q10 may then be freeze-dried.
In the present invention, crystals of coenzyme Q10 obtained may all be reduced
coenzyme QIO.
The purity of the crystallization of reduced coenzyme QIO may be above 90.00%-99.00%. The extraction solution of step (1) preferably comprises 5-40% hexane. In the present invention, sources of the palm plant may include
[I] Palm oil
[2] Crude palm oil
[3] Bleached palm oil
[4] RBD palm oil
[5] RBD palm olein oil
[6] Residual fiber oil
[7] Commercial fiber oil
[8] Palm fiber oil
[9] Crude palm kernel oil
[10] Palm fruit bunch
[I I] Palm woods
[12] Palm Fibre sludge
[13] Palm kernel oil
[14] Palm fatty acid oil
[15] Palm pressed fiber
In the present invention, the coenzyme QlO/reduced coenzyme QIO produced by palm oil and palm pressed fiber is estimated to be around 20-40% oxidized coenzyme Q10 and 60- 80% reduced coenzyme Q10.
In the present invention, the palm plant is preferably a naturally occurring plant.
According to another aspect of the present invention, there is provided coenzyme Q10 produced by any one of the methods described above.
Detailed Description of Some of the Preferred Embodiments of the Invention The following examples illustrate the invention without restricting it in any way.
Experiment 1.
1. Extraction solution (40% hexane and 25mM citrate solution, or 300ml 25% citrate solution), pH7.4 is put into a 10L tank. The said solution in the tank is sterilized by heating for 10 minutes at 121°C.
2. Palm pressed fibre is washed twice with water. The mixture of water and palm fibre is filtered, and the waste water is discarded. The residue (180g wet objects) is collected. The wet objects are then placed in a Mulitibeads shocker-B300 for one hour to break the palm fibre to concussion moss. The broken palm fibre is then collected.
3. 10% broken palm fibre is then added to the extraction solution. The palm fibre and extraction solution are mixed for 48 hours at a mixing revolution of 300 rpm. At the end of the mixing, the liquid part (extraction solution now containing the CoQlO) is collected and the waste palm fibre is discarded. (Optionally, the said liquid part and broken palm fiber may be separated from one another by centrifugation, before the waste palm fiber is discarded and the liquid part is collected.)
4. A sample of the above liquid is analysed for coenzyme Q10. Analysis of the coenzyme QlO/reduced coenzyme Q10 is conducted through high performance liquid
chromatography (HPLC).
Experiment 2.
1. Extraction solution (40% hexane and 25mM citrate solution), pH7.4 is put into a 10L tank. The said solution in the tank is sterilized by heating for 10 minutes at 121°C.
2. Palm pressed fibre is washed twice with water. The waste water is then discarded by filtration. The residue (wet objects) is collected. Dry palm fiber may then be obtained by spray drying of the wet objects.
3. 5L extraction solution is added to the palm fibre. The palm fibre and extraction solution are mixed for about 30 minutes at about 50 degrees Centigrade.
4. The mixture is then centrifuged and the liquid part (the supernatant) is collected. Another 5L of the extraction solution is added to the precipitate obtained from the centrifugation. The mixture is again stirred for 30 minutes at 50 degrees Centigrade, and then centrifuged.
5. The supernatants (the liquid part) obtained from both centrifugations above are collected (optionally by filtration). A sample analysed by HPLC shows that it contains 20% ubiquinone and 80% ubiquinol . 6. There are two possible options. 25g of FeC13 may be added to the liquids. The liquids are cooled to 4 degrees Centigrade for more than 10 hours to obtain crystallization of reduced CoQIO. Ethanol may be used to cool to 10 degrees Centigrade for 10 hours. Crystallization purity is 99% ubiquinol when 25g of FeC13 is added. 7. Another option would be to subject the extraction liquids or crystals to chromatography, in which case 98% ubiquinol would be obtained.
The crystals may be crushed and then packaged.
Apart from FeC13, other zinc agents can be used to separate out reduced coenzyme QIO. Oxidized coenzyme QIO can be separated out by using agents such as Sephadex 4B.
Through the extraction methods of the present invention, a large quantity of pharmaceutical grade coenzyme QlO/reduced coenzyme QIO which is natural, stable, non-genetically modified, can be obtained from palm fiber and other parts of the palm plant at a purity of 99.00%. The said coenzyme Q10 does not contain material from any other organisms and has no allergens to the human body. The coenzyme Q10 produced is safe, reliable, and can be used for medicine practical production.
Claims
1. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzymeQIO, said method involving the following steps:
(1) Addition of citrate and its salts solution into a suitable extraction solution which can extract oxidized coenzyme Q10 and or reduced coenzymeQIO from any parts or sources of a palm plant, addition of the said part or source of the palm plant, and maintenance of the temperature;
(2) Separation of the extraction solution of step (1);
(3) Removal of coenzyme Q10 and or reduced coenzyme Q10 from the solution of step (2).
2. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzyme Q10 according to claim 1 wherein the citrate and its salts solution in step (1) is at a concentration of 0.2- 15%.
3. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzyme Q10 according to claim 1 wherein maintenance of the temperature in step (1) is at about 4-50°C for 12-48 hours.
4. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzyme Q10 according to claim 1 wherein between step (2) and step (3), an alkaline solution is added into the extraction solution separated out in step (2) to obtain a pH of 3.5-9.3 and a temperature of 28-50°C is maintained.
5. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzyme Q10 according to claim 4 wherein the alkaline solution is NaOH solution.
6. A method according to claim 1 wherein the extraction solution containing the oxidized and or reduced coenzyme Q10 is dried to separate out the coenzyme Q10 from the extraction solution.
7. A method according to claim 6 wherein the extracted coenzyme Q10 is then freeze- dried.
8. A method according to claims 2, 3, 4, 5, 6 and 7.
9. A method of extracting one or both of oxidized coenzyme Q10 and reduced coenzyme Ql.O according to claim 1 wherein the concentration of oxidized coenzyme Q10 obtained is 0.2ug-4mg/ml and reduced coenzyme Q10 is 0.3-3mg/ml.
10. A method according to claim 1 wherein crystals of coenzyme Q10 obtained are all reduced coenzyme Q10.
11. A method according to claim 1 wherein the purity of the crystallization of reduced coenzyme Q 10 is above 90.00%-99.00%.
12. A method according to any one of claims 1-11 wherein the extraction solution of step (1) comprises 5-40% hexane.
13. A method according to claim 1 further comprising the following:
(a) The extraction solution comprises 40% hexane and 25mM citrate solution or 25% citrate solution, pH 7.4 and said extraction solution is sterilized prior to addition of the part or source of the palm plant
(b) Prior to mixing of the part or source of the palm plant with the extraction solution, said part or source of the palm plant is washed twice with water and the waste water is discarded
(c) The washed part or source of the palm plant (wet objects) is then placed in a shocker to break the said part or source to concussion moss
(d) The broken part or source of the palm plant is added to and mixed with the extraction solution at 10%
(e) At the end of the mixing, the extraction solution containing the coenzyme Q10 is collected and waste palm plant part or source is discarded.
14. A method according to claim 13 wherein in part (a), the extraction solution is sterilized by heating for 10 minutes at 121°C.
15. A method according to claim 13 wherein in part (b), the mixture of water and oil palm plant or source are filtered to discard the waste water.
16. A method according to claim 13 wherein in part (c), the shocker is a Multibeads shocker-B300 and the wet objects are placed in said shocker for one hour.
17. A method according to claim 13 wherein in part (d), the broken part or source of the oil palm plant is mixed with the extraction solution for 48 hours at a mixing revolution of 300 rpm.
18. A method according to claim 13 wherein in part (e), the extraction solution containing the coenzyme Q10 and waste palm plant part or source are separated from one another by centrifugation before said extraction solution containing the coenzyme Q10 is collected and said waste palm plant part or source is discarded.
19. A method according to claims 14, 15, 16, 17 and 18.
20. A method according to claim 1 further comprising the following:
(a) The extraction solution comprises 40% hexane and 25mM citrate solution, pH
7.4 and said extraction solution is sterilized prior to addition of the part or source of the palm plant.
(b) Prior to mixing of the part or source of the palm plant with the extraction solution, said part or source of the palm plant is washed twice with water and the waste water is discarded.
(c) The washed part or source of the palm plant is dried.
(d) The extraction solution is then added to the part or source of the palm plant and mixed.
(e) The mixture is centrifuged and the liquid part (the supernatant) is collected.
(f) Extraction solution is added to and mixed with the precipitate obtained from the centrifugation obtained in part (e), and the mixture is then centrifuged.
(g) The supematants (the liquid parts) obtained from centrifugations in part (e) and part (f) are collected and oxidized and or reduced coenzyme Q10 are obtained from said supematants.
21. A method according to claim 20 wherein in part (a), the extraction solution is sterilized by heating for 10 minutes at 121°C.
22. A method according to claim 20 wherein in part (b), the waste water is discarded by filtration.
23. A method according to claim 20 wherein in part (c), the washed part or source of the palm plant is dried by spray drying.
24. A method according to claim 20 wherein in part wherein in part (d), the extraction solution is mixed with the part or source of the palm plant for about 30 minutes at about
50 degrees Centigrade.
25. A method according to claim 20 wherein in part (f), the mixture of extraction solution and precipitate is stirred for 30 minutes at 50 degrees Centigrade prior to centrifugation.
26. A method according to claim 20 wherein in part (g), the supematants are filtered before oxidized and or reduced coenzyme Q10 are obtained from said supematants.
27. A method according to claims 21, 22, 23, 24, 25 and 26.
28. A method according to any one of claims 20-27 further comprising addition of FeC13 to the liquids collected in part (g) to obtain reduced coenzyme Q10 (ubiquinol).
29. A method according to any one of claims 20-27 further comprising addition of FeC13 to the liquids collected in part (g) and cooling of said liquids to obtain reduced coenzyme
Q10 (ubiquinol).
30. A method according to claim 29 wherein the liquids are cooled to 4 degrees Centigrade for more than 10 hours to obtain crystallization of the reduced coenzyme Q10 (ubiquinol).
31. A method according to claim 29 wherein ethanol is used to cool the liquids to 10 degrees Centigrade for 10 hours to obtain crystallization of the reduced coenzyme Q10 (ubiquinol).
32. A method according to any one of claims 20-27 further comprising use of zinc agents to separate out reduced coenzyme Q10 (ubiquinol).
33. A method according to any one of claims 20-27 further comprising subjecting the extraction liquids or crystals to chromatography to obtain ubiquinol.
34. A method according to any one of claims 20-27 further comprising use of Sephadex B to separate out oxidized coenzyme Q10 (ubiquinone).
35. A method according to any one of claims 1-34 wherein the parts or sources of the palm plant includes one or more of the following:
[1] Palm oil
[2] Crude palm oil
[3] Bleached palm oil
[4] RBD palm oil
[5] RBD palm olein oil
[6] Residual fiber oil
[7] Commercial fiber oil
[8] Palm fiber oil
[9] Crude palm kernel oil
[10] Palm fruit bunch
[11] Palm woods
[12] Palm Fibre sludge
[13] Palm kernel oil
[ 14] Palm fatty acid oil
[15] Palm pressed fiber
36. A method according to any one of claims 1-34 wherein the part or source of the palm plant is palm pressed fiber.
37. A method according to any one of claims 1-34 wherein the coenzyme QlO/reduced coenzyme Q10 produced by palm oil and palm fiber oil are 20-40% oxidized coenzyme Q10 and 60-80% reduced coenzyme Q10.
38. A method according to any one of claims 1-37 wherein the palm plant is a naturally occurring plant.
39. Coenzyme Q10 produced by any one of the methods of claims 1-38.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MYPI20094863 | 2009-11-16 | ||
| MYPI20094863A MY171902A (en) | 2009-11-16 | 2009-11-16 | Production of natural ubiquinone and ubiquinol by extraction from palm plant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2011059311A2 true WO2011059311A2 (en) | 2011-05-19 |
| WO2011059311A3 WO2011059311A3 (en) | 2011-11-24 |
Family
ID=43992274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/MY2010/000282 WO2011059311A2 (en) | 2009-11-16 | 2010-11-16 | Production of natural ubiquinone and ubiquinol by extraction from palm plant |
Country Status (2)
| Country | Link |
|---|---|
| MY (1) | MY171902A (en) |
| WO (1) | WO2011059311A2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102660378A (en) * | 2012-04-28 | 2012-09-12 | 青岛佰福得科技有限公司 | Method for extracting natural coenzyme Q10 by using palm residue |
| RU2613103C1 (en) * | 2016-02-04 | 2017-03-15 | Закрытое акционерное общество "Институт экспериментальной фармакологии" | Process for production of reduced form of coenzyme q10 |
| WO2022057603A1 (en) * | 2020-09-21 | 2022-03-24 | 宁夏泰胜生物科技有限公司 | Method for extracting coenzyme q10 from fermentation broth of coenzyme q10 |
| US11871391B2 (en) | 2010-12-03 | 2024-01-09 | Interdigital Patent Holdings, Inc. | Methods, apparatus and systems for performing multi-radio access technology carrier aggregation |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3769170A (en) * | 1970-03-31 | 1973-10-30 | Ajinomoto Kk | Method of producing coenzyme q10 by microorganisms |
| JPS5933354B2 (en) * | 1976-09-14 | 1984-08-15 | 鐘淵化学工業株式会社 | Production method of coenzyme Q |
| JP4426832B2 (en) * | 2002-12-03 | 2010-03-03 | 株式会社分子生理化学研究所 | Coenzyme Q-10 and method for analyzing 2-electron reduced form thereof |
-
2009
- 2009-11-16 MY MYPI20094863A patent/MY171902A/en unknown
-
2010
- 2010-11-16 WO PCT/MY2010/000282 patent/WO2011059311A2/en active Application Filing
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11871391B2 (en) | 2010-12-03 | 2024-01-09 | Interdigital Patent Holdings, Inc. | Methods, apparatus and systems for performing multi-radio access technology carrier aggregation |
| CN102660378A (en) * | 2012-04-28 | 2012-09-12 | 青岛佰福得科技有限公司 | Method for extracting natural coenzyme Q10 by using palm residue |
| WO2013159593A1 (en) * | 2012-04-28 | 2013-10-31 | 青岛佰福得科技有限公司 | Method for extracting coenzyme q10 and application of coenzyme q10 |
| RU2613103C1 (en) * | 2016-02-04 | 2017-03-15 | Закрытое акционерное общество "Институт экспериментальной фармакологии" | Process for production of reduced form of coenzyme q10 |
| WO2022057603A1 (en) * | 2020-09-21 | 2022-03-24 | 宁夏泰胜生物科技有限公司 | Method for extracting coenzyme q10 from fermentation broth of coenzyme q10 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2011059311A3 (en) | 2011-11-24 |
| MY171902A (en) | 2019-11-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Colla et al. | Antioxidant properties of Spirulina (Arthospira) platensis cultivated under different temperatures and nitrogen regimes | |
| CN106720466A (en) | It is a kind of while the method for extracting high phospholipid krill oil and astaxanthin ester krill oil high | |
| Costa et al. | 16 microalgae for food production | |
| KR20220117742A (en) | Hangover Treatment Composition Which Comprises Aldehyde Dehydrogenase and Glutathione | |
| WO2011059311A2 (en) | Production of natural ubiquinone and ubiquinol by extraction from palm plant | |
| CN114099556A (en) | Yeast powder rich in nicotinamide mononucleotide, its preparation method and use | |
| KR102736990B1 (en) | Recombinant yeast introduced with a gene encoding retinol dehydrogenase and manufacturing method the same | |
| US20250154550A1 (en) | Hangover reliever containing glutathione and aldehyde dehydrogenase | |
| Wilawan et al. | Advancement of carotenogenesis of astaxanthin from Haematococcus pluvialis: recent insight and way forward | |
| CN106722934A (en) | A kind of anti-ageing health food for containing peptide extract containing earthworm, clam worm | |
| CN111480830A (en) | Enzyme liquid, application and preparation method thereof and anti-aging product | |
| Luo et al. | Enhancing the functionality of plant-based Yogurt: Integration of lycopene through dual-stage fermentation of soymilk | |
| CN104522750A (en) | Alga healthcare food | |
| Itatani et al. | Fermented royal jelly enriched with 10‐hydroxydecanoic acid and its potential for enhancing mucosal immunity | |
| JP2011030487A (en) | Method for producing quinones | |
| Huang et al. | Small‐Molecule Peptides from Lactiplantibacillus plantarum SCS2 Attenuate H2O2‐Induced Oxidative Damage in INS‐1 Cells via Regulating the Keap1‐Nrf2 Signaling Pathway | |
| CN102057991B (en) | Corn oil rich in coenzyme Q10 and production method thereof | |
| WO2016103236A1 (en) | Process of making wine, pomace juice, powder, and beverages from juice and powder from a grape bunch | |
| CN101155923B (en) | Method for producing probiotically derived compounds | |
| CN111499707A (en) | A kind of hypoglycemic and lipid-lowering peptide and its application | |
| Xiaoguang et al. | Improvement of Physiological Characteristic of Selenium‐Enriched Candida utilis with Amino Acids Addition | |
| Sarkisian | Research of the properties of grape processing products in relation to its application in spa and wellness industries | |
| CN103757076A (en) | Method for increasing valence of glutathione in saccharomyces cerevisiae fermentation liquor by utilizing oxygen carrier | |
| KR101672827B1 (en) | Pharmaceutical composition for anti-oxidative or anti-inflammatory comprising leaf extract of alaskan ginseng | |
| Kalita et al. | Algal Astaxanthin: Genetics, Synthesis, and Advanced Biotechnological Strategies for Therapeutic Uses |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NENP | Non-entry into the national phase |
Ref country code: DE |
|
| 122 | Ep: pct application non-entry in european phase |
Ref document number: 10830242 Country of ref document: EP Kind code of ref document: A2 |