WO2014189357A1 - Procédé d'extraction d'un composé phénolique - Google Patents

Procédé d'extraction d'un composé phénolique Download PDF

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Publication number
WO2014189357A1
WO2014189357A1 PCT/MY2014/000075 MY2014000075W WO2014189357A1 WO 2014189357 A1 WO2014189357 A1 WO 2014189357A1 MY 2014000075 W MY2014000075 W MY 2014000075W WO 2014189357 A1 WO2014189357 A1 WO 2014189357A1
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WIPO (PCT)
Prior art keywords
pkc
process according
acid
hydrolysate
hydrolysed
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PCT/MY2014/000075
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English (en)
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WO2014189357A8 (fr
Inventor
Julia BINTI IBRAHIM
Shwu Fun KUA
Norhafizi BIN HASIM
Khairul Izwan BIN NAN
Christopher Kuok Weng OOI
Hirzun MOHD YUSOF
Harikrishna Kulaveerasingam
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Sime Darby Malaysia Berhad
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Publication of WO2014189357A1 publication Critical patent/WO2014189357A1/fr
Publication of WO2014189357A8 publication Critical patent/WO2014189357A8/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/88—Liliopsida (monocotyledons)
    • A61K36/889—Arecaceae, Palmae or Palmaceae (Palm family), e.g. date or coconut palm or palmetto
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine

Definitions

  • the present disclosure relates generally to a process for the treatment of palm kernel cake and for extracting phenolic compounds. More particularly, the disclosure relates to processes for the enzyme catalysed hydrolysis of palm kernel cake and to products obtained thereby.
  • Phenolic compounds are known as secondary metabolites found in plants. Some of these compounds have been found to exhibit a wide range of biological and physiological properties such as anti-oxidant, anti-artherogenic, anti-inflammatory and anti-thrombotic activities. In US 2010/0331399, it is reported that phenolic compounds extracted from fruits are used in the treatment or prophylaxis of cardiovascular diseases, colon cancer and digestive health.
  • tea polyphenols show numerous physiological activities such as anti-oxidant, anti-bacterial, and anti-cancerous, as well as reducing blood cholesterol.
  • Agro-industrial by-products such as rapeseed, rice hulls, apple peels as well as grape seeds and skin are reported as rich sources of phenolic compounds.
  • the by-product from olive oil industry is another potential source for phenolic compounds.
  • US 2008/0014322 discloses that olive polyphenol concentrate is derived from by-product produced in the olive oil extraction process.
  • Oil palm fruit is a rich source of phenolic compounds.
  • US Pat. No. 7,387,802 discloses a process for extraction of phenolic compounds from palm oil mill effluent (POME).
  • US 2010/0197780 Al describes methods for prevention and treatment of cancer using palm phenolic compounds extracted from POME.
  • WO 2010/087693 Al discloses a composition comprising oil palm phenolics compounds for use in prevention of neorodegerative ailments. The phenolic compounds are extracted from vegetation liquor of the palm oil milling process, oil palm fruit, fresh fruit bunch and oil palm frond.
  • US 2010/0183786 Al discloses using palm phenolic compounds extracted from POME as food preservative and US 2010/0209544 Al discloses a cosmeceutical composition comprising palm phenolic compounds extracted from POME.
  • Oil palm leaf ethanol extract can reduce hyperglycaemia and lipid oxidation in STZ-rats and this indicates the potential use of phenolic compounds from oil palm leave as a new functional food ingredient.
  • the fruit of the oil palm Elaeis guineensis, yields two distinct oils: palm oil, derived from the outer parts of the fruit, and palm kernel oil, derived from the seed of the fruit, or kernel.
  • the palm kernel contains a hypothetical oil content of approximately 50-55%.
  • high pressure expellers are used to extract the oil from the kernel, although solvent-based extraction processes can also be used.
  • the extraction process affords the palm kernel oil and, as the waste by-product, the "de-oiled" solid mass, or pulp, referred to as "palm kernel cake” (P C), or sometimes, palm kernel expeller” (P E). While the extraction process affords the majority of the oil present in the kernel a significant proportion of the oil is retained in the PKC (about 10% w/w).
  • the PKC also contains some protein and significant amounts of polysaccharides, including hemicelluloses, celluloses and pectins which make up the cell walls, as well as a high phosphorus to calcium ratio. PKC is therefore utilised as a high energy, high fibre feed supplement for ruminants.
  • a relatively low nutrition value and only average protein content, together with a poor amino acid profile means that PKC, on its own, is ever only a medium quality feed, ranked a little higher than copra cake but lower than fish meal and ground nut cake in its protein value.
  • PKC can be considered as a low value product.
  • Phenolic compounds are potentially useful compounds and there remains a need for identifying further sources thereof and for methods for recovering the phenolic compounds from the same.
  • the present disclosure describes a process for extracting phenolic compounds from the PKC by-product produced in the palm kernel oil extraction process.
  • the process comprises treating PKC with an organic solvent to obtain an organic extract containing one or more phenolic compounds.
  • the process utilizes an enzyme-catalysed hydrolysis of PKC which employs one or more enzymes to breakdown, or degrade, the polysaccharide, and optionally protein, components which comprise plant cell walls, releasing components within, such as phenolic compounds.
  • the released phenolic compounds may then be recovered from the hydrolysis products by extraction into one or more organic solvents.
  • a process for extracting one or more phenolic compounds from palm kernel cake (PKC), comprising:
  • the PKC subjected to hydrolysis is expeller pressed, derived from the mechanical screw press oil extraction method.
  • the PKC is derived from solvent extraction methods.
  • the enzymes are dissolved or suspended in water to provide an enzymatic solution which is mixed with the PKC.
  • one or more enzymes capable of hydrolysing at least a portion of hemicellulose polysaccharides (hemicellulases) present in the PKC are used.
  • one or more enzymes capable of hydrolysing or degrading at least a portion of mannan present in the PKC are used.
  • the process employs at least mannanase.
  • one or more enzymes capable of hydrolysing or degrading other cell wall constituents such as celluloses, pectins and associated proteins are used, that is to say one or more of cellulases, pectinases and proteinases.
  • the hydrolysis process uses a mixture of at least two of mannanase, xylanase, cellulase, pectinase and protease.
  • the hydrolysis process is conducted using mannanase, xylanase, cellulase and pectinase, optionally together with protease.
  • the enzymes comprise or consist of mannanase and pectinase.
  • the first organic solvent used to treat the PKC hydrolysate is ethyl acetate.
  • the second organic solvent used to treat hydrolysed PKC is an alcohol, for example methanol or ethanol.
  • the process further comprises drying or concentrating the PKC hydrolysate prior to the step of treating the PKC hydrolysate with a first organic solvent to obtain an organic extract of PKC hydrolysate.
  • the process further comprises pre-treating the PKC chemically or physically prior to the step of mixing the PKC with the enzymatic solution.
  • the process further comprises de-fatting the PKC prior to the step of mixing the PKC with the enzymatic solution. In one or more embodiments, the process further comprises de-fatting the hydrolysed PKC prior to the step of treating the hydrolysed PKC with the second organic solvent.
  • the process further comprises pre-treating the hydrolysed PKC prior to the step of mixing the hydrolysed PKC with the second organic solvent.
  • the disclosure also provides a process for extracting one or more phenolic compounds from PKC comprising treating said PKC with an organic solvent to obtain an organic extract of PKC containing one or more phenolic compounds.
  • the organic solvent is one selected from the group consisting of methanol and ethanol. In some embodiments, this process may precede a hydrolysis step.
  • the present disclosure also relates to hydrolysed PKC and PKC hydrolysate obtained by the processes described herein.
  • an organic extract of PKC hydrolysate or hydrolysed PKC containing one or more phenolic compounds In another aspect there is provided, an organic extract of hydrolysed PKC containing one or more phenolic compounds.
  • the disclosure relates to purified phenolic compounds obtained by the processes described herein.
  • an organic extract of PKC hydrolysate containing one or more phenolic compounds.
  • invention includes all aspects, embodiments and examples described herein.
  • Palm kernel cake is the material retained after extraction of palm kernel oil from the palm kernel.
  • Two major processes are typically used; a high pressure screw press method (e.g. expeller press) or a solvent-based (e.g. hexane) extraction method.
  • the PKC which is produced by each method differs in the amount of palm kernel oil retained in the cake : 5-12% for expeller pressed PKC versus 0.5-3% for solvent extracted PKC.
  • the PKC subjected to hydrolysis is that obtained after the first pressing of palm kernels through high pressure expeller press (first pressed PKC). In other embodiments of the present disclosure, the PKC subjected to hydrolysis is that obtained after the second pressing of palm kernels through high pressure expeller press (second pressed PKC). In other embodiments the PKC is obtained from solvent-based (e.g. hexane) extraction of palm kernel oil. It will be understood that the PKC used in the processes described herein may be PKC obtained from one or more such processes.
  • Reference to PKC includes the material obtained directly from the oil extraction process.
  • the material may be subjected to one or more further physical and/or chemical treatments prior to being subjected to enzymatic hydrolysis.
  • Such treatments may include one or more of milling, crushing, grinding, chopping or other process of communition, hydrothermal treatment, such as steam or hot liquid water treatment, and acid (e.g. sulphuric acid) or base (e.g. sodium hydroxide) treatment.
  • Pre-treating the PKC chemically or physically helps to alter the hemicellulose structure of the PKC. This causes the PKC to be more accessible to the organic solvents and enzymes. This in turns helps to increase yield of the phenolic compounds.
  • the P C subjected to enzymatic treatment may be in the form of meal, flakes, granules, pellets or any other suitable form.
  • the PKC has a size in the range of about mesh size 1mm to about mesh size 10mm, for example from about l-5mm.
  • Hemicelluloses are a heterogeneous group of polysaccharides, which together with celluloses, pectins, and also proteins, are present in plant cell walls.
  • the group of polysaccharides known as hemicelluloses include polysaccharides having P-(l ⁇ 4)-linked backbones of glucose, mannose or xylose with an equatorial configuration, and include xyloglucans, xylans, mannans (including galactomannans) and glucomannans (including galactoglucomannans).
  • Xylans feature a backbone of p-(l ⁇ 4)-linked xylose residues
  • mannans feature a backbone predominantly of p-(l ⁇ 4)-linked mannose units
  • glucomannans contain a backbone of glucose and mannose
  • xyloglucans contain a backbone of glucose with xylose-containing sidechains
  • the processes described herein subject PKC to enzymatic hydrolytic treatment by contacting or mixing the PKC with one or more suitable enzymes under aqueous conditions, thereby degrading cell wall polysaccharides, releasing oil, smaller saccharide units, phenolic compounds and protein from the PKC.
  • the enzymes may be presented in the form of an aqueous mixture in which the enzymes are dissolved or dispersed in water, herein also referred to as an "enzyme solution" or "enzyme cocktail".
  • the water used in the enzymatic hydrolysis step is suitably purified, for example by reverse osmosis (RO).
  • one or more enzymes capable of hydrolytically cleaving one or more chemical bonds within a hemicellulose polysaccharide contained in the PKC are employed. Such enzymes may be referred to generally as hemicellulases. Hemicellulases are a diverse group of enzymes which can be categorised according to the chemical bonds they cleave: glycoside hydrolases (GH), which hydrolyse glycosidic bonds within the polysaccharide, and carbohydrate esterases (CE), which hydrolyse ester linkages within the polysaccharide.
  • GH glycoside hydrolases
  • CE carbohydrate esterases
  • GHs can be further categorised according to whether the enzyme cleaves a bond within the polysaccharide backbone (endo-glycoside) or cleaves off a mono- or di-saccharide side chain (exo-glycoside).
  • hemicellulases contemplated herein include endo-p-l,4-xylanase, exo-p-l,4-xylosidase, endo-p-l,4-mannanase, exo-p-1,4- mannosidase, a-arabinofuranosidase, endo-a-L-l,5-arabinase, a-glucuronidase, a- galactosidase, ⁇ -glucosidase, endo-galactanasee, acetyl xylan esterase and acetyl mannan esterase and mixtures thereof.
  • one or more other enzymes which hydrolyse other components, such as lignans, celluloses or proteins, within the PKC may also be used.
  • Some non-limiting examples thereof include lignan hydrolysing enzymes (lignases) cellulose hydrolysing enzymes (cellulases, e.g.
  • endo-l,4-p-glucanase carboxymethyl cellulase, endo-l,4-p-D- glucanase, p-l,4-glucanase, p-l,4-endoglucan hydrolase, exocellulosase and ⁇ - glucosidase), pectin hydrolysing enzymes (pectinases, e.g. polygalactouranoase), and protein hydrolysing enzymes to cleave cell wall-linked proteins (proteases).
  • Enzymes for use in the processes described herein are obtainable from microbial (e.g. fungal and bacterial) sources (e.g. Aspergillus and Tricoderma) and are commercially available.
  • Such enzymes may include a mixture of enzymes and have one or more modes of action and specificity and are commonly simply referred to as, for example, "hemicellulase”, “xylanase”, “cellulase”, “mannanase” etc.
  • hemicellulase typically comprises a mixture of hemicellulase enzymes, and, optionally, other enzymes, thus having multiple modes of action and specificity.
  • suitable enzymes and combinations thereof having regard to their mode of action and specificity.
  • the hydrolysis is advantageously achieved using one or more hemicellulose degrading enzymes, e.g. hemicellulases, including mannanases.
  • hemicellulose degrading enzymes e.g. hemicellulases, including mannanases.
  • the enzymes comprise a mixture of two, three or four or more of mannanase, cellulase, pectinase, xylanase and protease.
  • Certain embodiments utilise at least one hemicellulase, such as mannanase, enzyme.
  • an enzyme mixture or cocktail is used which, in addition to mannanase, further comprises one, two, three or more of cellulase, pectinase, xylanase and protease.
  • the enzyme mixture comprises or consists of mannanase and pectinase.
  • the PKC is contacted with the enzyme or enzymes for a time and under conditions sufficient to effect at least partial degradation of the plant cell wall through hydrolysis of polysaccharide cell wall components of the PKC.
  • the skilled person will be able to determine appropriate conditions, including length of incubation period, temperature of incubation, pressure, pH conditions, quantity and combination of enzymes used and relative ratios of components.
  • the PKC and enzymes in aqueous solution may be agitated by stirring the mixture or, rotating, rocking or shaking the incubation vessel.
  • the hydrolysis can be performed under acidic, neutral or mildly basic conditions and may depend on and be adjusted as necessary by the addition of an appropriate acid or base according to the enzyme source used.
  • the hydrolysis is performed at a pH in the range of 3-8 such as pH 3-5, pH 5-7 or pH 7-8.
  • the hydrolysis may be performed at a pH of about 3, or 4, or, 5 or, 6, or 7, or 8.
  • the hydrolysis is performed at a pH of about 5.
  • the hydrolysis proceeds over a period of at least about 12 hours, more advantageously, at least about 24 hours, or from about 36 or 48 hours to about 72 hours, or even up to about 168 hours.
  • longer or shorter incubation periods may be utilised depending on other factors such as the types of enzymes and amount thereof used, quantity of PKC being treated, incubation temperature etc.
  • the incubation may be carried out at any suitable temperature which allows for enzyme activity under the relevant aqueous conditions.
  • hydrolysis may be performed at a temperature in the range of about 20-80°C, such as in the range of about 25-75°C, for example about 40-60°C, or 45-55°C.
  • the incubation is performed at a temperature of about 50°C or about 60°C.
  • the ratio of PKC to aqueous enzymatic solution may depend on the nature of the enzymes and the concentration of enzymes in solution and may advantageously be anywhere from about 1 : 1 to 1 : 10 (w/v).
  • the ratio of PKC to aqueous enzyme solution is such that the hydrolysis mixture is sufficiently concentrated to allow hydrolysis to proceed to the desired extent under the prevailing conditions.
  • the ratio of PKC to aqueous enzymatic solution is from about 1 :1 to about 1 :5, such as about 1 :2, 1 :3 or 1 :4. In further embodiments, the ratio is about 1 :3.
  • An effective amount of one or more enzymes includes an amount of enzyme(s) capable of hydrolysing polysaccharide and/or components of PKC.
  • the total enzyme amount will depend on a number of factors including the nature of the enzyme(s), the amount of PKC to be treated etc, but typically may be independently in the range of about 0.1-10% (w/w) of dry PKC weight for each enzyme type, for example an amount in the range of about 0.5% (w/w) to about 3.0% (w/w), such as in the range of about 0.5% (w/w) to about 1.5% (w/w).
  • each enzyme is independently added in an amount (based on dry PKC weight) of about 0.2, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2, 1.3, 1.4, 1.5, 2.0, 2.5, 3.0 or 5.0%.
  • the PKC is mixed with a cocktail of enzymes, including at least mannanase and pectinase, for example a mixture comprising mannanase, cellulase, xylanase, pectinase and optionally protease, each independently in an amount of 0.5-3.0% (w/w) on a dry PKC basis, in water, added to the PKC in a ratio of about 1 :3 to 1 :5 (PKC:water)
  • the mixture may be incubated for a period of from about 24 to 168 hours at a temperature in the range of about 40-60°C.
  • the cocktail of enzymes used are mannanase and pectinase.
  • PKC hydrolysate refers to the aqueous phase containing dissolved or dispersed products released by the enzymatic hydrolysis process.
  • hydroylsed PKC also referred to herein as "kernel paste” refers to the paste-like P C which remains after PKC has been subjected to enzymatic hydrolysis.
  • the PKC hydrolysate is separated from the hydrolysed PKC by any suitable means, including one or more of decantation, such as centrifugal decantation, centrifugation and filtration.
  • Centrifugal decantation may advantageously be carried out at any appropriate bowl speed, for example at a speed in the range of from about 2000rpm to about 5000rpm, such as about 3000rpm to about 4500rpm, at a suitable feed rate, such as from about 4, 6, 8 or lOL/min.
  • Deactivation may be effected by heating the hydrolysate for a time and a temperature sufficient to deactivate the enzymes, for example, at a temperature of about 90-100°C for about 10-15 minutes.
  • the present disclosure also relates to PKC hydrolysate and hydrolysed PKC obtained through hydrolysis of PKC.
  • One or more phenolic compounds may be extracted from a product of the hydrolysis process or from PKC which has not been subjected to hydrolysis.
  • a process for extracting phenolic compounds from PKC using organic solvent, such as methanol or ethanol is provided.
  • the process comprises the steps of providing a PKC and mixing the PKC with methanol or ethanol as described herein to obtain an organic extract of PKC containing one or more phenolic compounds.
  • the phenolic compounds are extracted from the PKC, PKC hydrolysate or hydrolysed PKC by treating the PKC, PKC hydrolysate or hydrolysed PKC with an organic solvent in which the compounds are soluble.
  • Any suitable organic solvent may be used.
  • the first and second organic solvents may be the same or different. In some embodiments, the first and second organic solvents are the same. In other embodiments, they are different.
  • “treat” and “treating” refers to the contact of said organic solvent with the PKC, PKC hydrolysate or hydrolysed PKC for a time and under conditions to extract one or more phenolic compounds into the organic solvent.
  • the treatment may be carried out at any suitable temperature, such as from about 4°C, to room temperature (about 20-25°C), up to the boiling point of the solvent.
  • the treatment comprises mixing, shaking, stirring or agitating the PKC, PKC hydrolysate or hydrolysed PKC with the organic solvent.
  • the material may be extracted by percolating the organic solvent through the solid material, such as in a soxhlet extraction apparatus.
  • the PKC hydrolysate is treated with a first organic solvent to obtain an organic extract of PKC hydrolysate containing phenolic compounds.
  • Suitable organic solvents that can be used include solvents that are immiscible with water so as to allow for separation of the phenolic compound-containing organic phase from the aqueous phase.
  • suitable solvents include ethyl acetate, ethers, such as diethyl ether, dichloromethane, chloroform and alcohols, such as butanol.
  • the ratio of the PKC hydrolysate to the organic solvent used in this embodiment may be in the range from about 1 : 1 to about 1 :5, such as about 1 :3.
  • the organic phase may be separated from the aqueous phase, and optionally dried to remove water, and concentrated.
  • the hydrolysed PKC is mixed with a second organic solvent to obtain an organic extract of hydrolysed PKC containing phenolic compounds.
  • Suitable second organic solvents that can be used in this step may be water miscible and include, but are not limited to, alcohols, such as propanol, ethanol and methanol, acetone and acetonitrile.
  • the ratio of the hydrolysed PKC to the organic solvent used in this step is in the range from 1 :2 to 1 :20, such as about 1 :5, or about 1 : 10, or about 1 :15.
  • the mixture of hydrolysed PKC and organic solvent may be agitated while treating to extract the phenolic compounds.
  • the mixture may be agitated for any appropriate amount of time and by any suitable method known in the art. Any suitable speed for agitation may be employed. In an embodiment, the mixture is agitated at, for example, 200 rpm, at about 4°C overnight.
  • the organic extract of hydrolysed PKC may further be subjected to centrifugation, filtration or any method known in the art to remove any insoluble particles present in the organic extract of hydrolysed PKC.
  • the hydrolysed PKC may optionally be washed with water before it is mixed or treated with the second organic solvent.
  • the PKC hydrolysate is dried or concentrated prior to the step of treating the PKC hydrolysate with the first organic solvent to obtain an organic extract of PKC hydrolysate.
  • the first organic solvent may be a water-miscible solvent.
  • the PKC hydrolysate can be dried or concentrated by any suitable methods known in the art including, but are not limited to, distillation, spray drying, vacuum evaporation, concentration or freeze-drying. In an embodiment, the PKC hydrolysate is freeze-dried. Suitable first organic solvents that can be used in this embodiment include, but are not limited to, ethanol and methanol.
  • the organic extract of PKC hydrolysate (for example, ethanol extract of dried PKC hydrolysate or methanol extract of dried PKC hydrolysate) obtained hereby may further be subjected to centrifugation, or filtration or any method known in the art to remove any insoluble solids.
  • the process may further involve pre-treating the hydrolysed PKC prior to the step of mixing the hydrolysed PKC with the second organic solvent.
  • the hydrolysed PKC may be pre-treated chemically or physically as described above.
  • the process may further involve de-fatting the PKC prior to the step of subjecting the PKC to enzymatic hydrolysis.
  • the process may also further involve de- fatting the hydrolysed PKC prior to the step of mixing the hydrolysed PKC with the second organic solvent.
  • the PKC and the hydrolysed PKC may contain some oil residues which can affect the efficiency of solvent extraction.
  • De-fatting is performed to remove the oil residues from the PKC and the hydrolysed PKC.
  • De-fatting involves a solvent extraction method which uses non-polar solvent to remove the oil residues.
  • non-polar solvents include, but are not limited to, hexane, ethyl acetate and diethyl ether.
  • the solvents are suitable for use in the food industry.
  • a mixture of PKC and organic solvent may be agitated while treating the PKC to extract the one or more phenolic compounds.
  • the mixture may be agitated for any appropriate amount of time and by any suitable method known in the art. Any suitable speed for agitation may be employed.
  • the mixture is agitated at, for example, 200 rpm, at about 4°C overnight.
  • the organic extract of PKC may further be subjected to centrifugation, filtration or any method known in the art to remove any insoluble particles present in the extract.
  • the extraction steps described hereinabove may be carried out with or without sonication in an ice-cooled water bath, for a suitable time, such as for about 15 minutes.
  • solvent includes 100% organic solvent (either a single solvent or a mixture of solvents) or a mixture of solvent(s) and water.
  • the solvent water ratio may be at least 1 :1 , such as about 2:1 , or about 3:1 , or about 4: 1, 9: 1, 19:1, 99: 1 or greater.
  • PKC may be treated with one or more organic solvents to obtain an organic extract.
  • the treated PKC may then be subjected further to a hydrolysis process and further extraction as described herein so as to increase the recovery of one or more phenolic compounds.
  • the organic extracts of PKC, the PKC hydrolysate and the hydrolysed PKC obtained by the process of the present invention contain one or more phenolic compounds selected from 4-hydroxybenzoic acid, 3,4-dihydroxybenzoic acid, d- glucoronic acid, cinnamic acid, syringic acid, vanillic acid, quinic acid, sinapic acid, shikimic acid, ferulic acid, caffeic acid and glutaric acid.
  • Any one or more phenolic compounds may be further purified from the organic extracts to afford substantially pure compounds, by which is meant compounds of at least about 90% purity, such as at least about 92% purity, or at least about 95% purity, or at least about 98% purity or at least about 99% purity.
  • the phenolic compounds may be purified by any suitable methods known in the art, including chromatography and/or crystallization.
  • the hydrolysate of PKC was freeze-dried.
  • the dried hydrolysate of PKC was extracted with ethanol (with dried hydrolysate to ethanol in a ratio of 0.16g:1.6 mL).
  • the ethanol extract of hydrolysate of PKC was centrifuged to remove insoluble particles.
  • the ethanol extract was then dried under oxygen free nitrogen (OFN) and the dried extract was then re- dissolved in methanol.
  • the extract was analyzed using UPLC-ESI-MS/MS to identify the phenolic compounds present in the extract. The results obtained are as shown in Table 1 and Table 2.
  • the freeze-dried hydrolysate of PKC was extracted with methanol (with dried hydrolysate to methanol in a ratio of 0.08g: lmL).
  • the methanol extract of hydrolysate of PKC was centrifuged to remove insoluble particles.
  • the extract was analyzed using UPLC-ESI- MS/MS to identify the phenolic compounds present in the extract. The results obtained are as shown in Table 1 and Table 2.
  • PKC palm kernel cake

Abstract

La présente invention concerne de manière générale un procédé pour le traitement de tourteaux de palmiste et l'extraction de composés phénoliques. En particulier, l'invention concerne des procédés d'hydrolyse catalysée par des enzymes de tourteaux de palmiste, et les produits ainsi obtenus.
PCT/MY2014/000075 2013-05-21 2014-04-24 Procédé d'extraction d'un composé phénolique WO2014189357A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019039553A1 (fr) * 2017-08-24 2019-02-28 株式会社新菱 Procédé de production d'acide shikimique

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US20100183786A1 (en) 2007-04-12 2010-07-22 Yew Ai Tan Palm phenolics and flavonoids as potent biological and chemical antioxidants for applications in foods and edible oils
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