US20150201660A1 - Extraction Method - Google Patents

Extraction Method Download PDF

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US20150201660A1
US20150201660A1 US14/423,995 US201314423995A US2015201660A1 US 20150201660 A1 US20150201660 A1 US 20150201660A1 US 201314423995 A US201314423995 A US 201314423995A US 2015201660 A1 US2015201660 A1 US 2015201660A1
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extract
ethanol
food
sugar cane
supernatant
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David Kannar
Barry James Kitchen
Lance Sparrow
Gregory Yu Foo Szto
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Product Makers Australia Pty Ltd
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Product Makers Australia Pty Ltd
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Priority claimed from AU2012903726A external-priority patent/AU2012903726A0/en
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    • A23L1/3002—
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/52—Adding ingredients
    • A23L2/60—Sweeteners
    • A23L1/2363—
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • 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
    • 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)
    • A61K36/899—Poaceae or Gramineae (Grass family), e.g. bamboo, corn or sugar cane
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
    • C13B10/00—Production of sugar juices
    • C13B10/02—Expressing juice from sugar cane or similar material, e.g. sorghum saccharatum
    • C13B10/06—Sugar-cane crushers
    • C—CHEMISTRY; METALLURGY
    • C13—SUGAR INDUSTRY
    • C13B—PRODUCTION OF SUCROSE; APPARATUS SPECIALLY ADAPTED THEREFOR
    • C13B10/00—Production of sugar juices
    • C13B10/14—Production of sugar juices using extracting agents other than water, e.g. alcohol or salt solutions
    • 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
    • A23L21/00—Marmalades, jams, jellies or the like; Products from apiculture; Preparation or treatment thereof
    • 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
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • 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
    • A23L7/00—Cereal-derived products; Malt products; Preparation or treatment thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

Definitions

  • the present invention relates to extracts derived from sugar cane and the subsequent processing streams (e.g., raw sugar, molasses, bagasse, mill mud and field trash).
  • the present invention also relates to processes for producing the extracts.
  • the present invention further relates to use of the extracts to reduce the available calorific value and/or glycaemic index of foods and beverages, and to use of the extracts in methods of treating or preventing diseases such as diabetes and metabolic syndrome as well as underlying conditions including but not limited to inflammation.
  • sugar cane After being mechanically harvested, sugar cane is transported to a primary mill and crushed between serrated rollers. The crushed sugar cane is then pressed to extract the raw sugar juice, while the bagasse (leftover fibrous material) is used for fuel. The raw juice is then heated to its boiling point to extract any impurities, then lime and bleaching agents are added and mill mud is removed. The raw juice is further heated under vacuum to concentrate and increase Brix value. The concentrated syrup is seeded to produce bulk sugar crystals and a thick syrup known as molasses. The two are separated by a centrifuge and the molasses waste stream is collected for use as a low-grade animal feedstock.
  • bagasse leftover fibrous material
  • the sugar refining process thus generates a large number of products including raw juice, bagasse, mill mud, clarified juice, molasses, dunder and sugar crystals.
  • Dunder is produced when sugar or molasses is fermented under controlled conditions to produce ethanol.
  • the bulk sugar crystals from the above process are further refined to produce many commercially available sugar products.
  • the further refining may include mixing the bulk sugar crystals with a hot concentrated syrup to soften the outer coating on the crystals.
  • the crystals are then recovered by centrifuge and subsequently dissolved in hot water, a step that is sometimes called affination.
  • This sugar liquor is then further purified by carbonation or phosfloatation, filtration, decolourisation and then seeded with fine sugar crystals.
  • the crystals are separated from the syrup by centrifugation, then dried, graded and packaged. There may be several repetitions of recovering sugar crystals from the sugar liquor.
  • the dark sugar syrup which is left after all of the sugar crystals have been recovered is also called refinery molasses.
  • Molasses and other products of the sugar refining process are complex mixtures of substances. Typically they are difficult to refine further and there are often substances in the compositions that poison standard separating materials. Molasses and the other thick syrups and juices typically comprise polyphenols, polysaccharides, flavonoids, peptides and proteins, minerals, organic acids, and mono and disaccharides. Complex polymers are also formed during processing (e.g., melanoidins).
  • the key consideration with a primary sugar milling operation is to maximise the extract and recovery of sucrose.
  • sugar refineries processing primary mill sugar is to improve sucrose purity.
  • Ethanol has been used in the recovery of sucrose from waste streams such as molasses (U.S. Pat. No. 1,730,473) and removal of impurities (U.S. Pat. No. 4,116,712; U.S. Pat. No. 2,000,202).
  • Ethanol has also been used in the isolation of individual polyphenols from dunder, including tricin, luteolin or apigenin (WO 2004/014159).
  • ethanol was first used in a crude clean up step to crash out impurities and then as part of a solvent mixture to chromatographically isolate fractions comprising specific polyphenols.
  • Molasses, golden syrup and treacle have been used as a health food since the early 20th century and there have been claims that they are good therapies or cures for a wide range of disorders.
  • Recent evidence demonstrates that novel sugar cane phytochemicals contained in, the products of the sugar cane refining process reduce glycaemic index (GI) and therefore reduce the risk of obesity and diabetes.
  • GI glycaemic index
  • the strong taste of these sugar cane derived products containing high molecular weight colourants makes them unpalatable to many people and the high viscosity of treacle and molasses makes them difficult to handle and unstable for incorporation into other foodstuffs.
  • the other products of cane sugar refining such as bagasse and mill mud are known to include potentially useful substances but their hitherto intractable nature and instability has meant that they are usually thrown away as waste.
  • Extracts derived from sugar cane containing isolated polyphenols have been produced previously but are not as effective as complex mixtures of polyphenols and flavonoids derived from sugar cane products. Extracts derived from sugar cane containing mixtures of polyphenols and flavonoids have been produced previously but are dark coloured and bitter tasting, thus reducing the palatability and/or appearance of the finished food or beverage to which they are added. Accordingly, it is desirable to develop an improved extraction method that results in a sugar cane derived extract having an increased concentration of polyphenols, lower colour and decreased bitterness to avoid the palatability problems associated with known extracts. Extracts with these improved properties would find broader use in foods, nutraceuticals and pharmaceuticals compared to current offerings.
  • the present inventors have developed a process for producing a sugar cane derived extract comprising polyphenols and/or flavonoids in more functionally effective amounts and having improved taste, lower colour and polysaccharide content.
  • the extracts of the present invention are believed to provide a synergistic combination of polyphenols and other components that are not contemplated in the prior art. As a consequence, the extract can be added back to foods or beverages in smaller quantities without significantly affecting the palatability and/or colour of the product.
  • the present invention provides a process for producing an extract derived from sugar cane, the process comprising:
  • the extract may be a powder, including a freeze dried powder or dehydrated powder.
  • the extract is a liquid extract, more preferably an aqueous extract.
  • the process may further include:
  • a preliminary extraction mixture e.g., comprising at least about 25% v/v ethanol
  • the preliminary supernatant may then be subjected to the process of the invention described above.
  • isopropanol can be used in place of ethanol.
  • any suitable food grade polar solvents could also be used in place of ethanol.
  • Suitable food grade polar solvents include butanol, acetone, ethyl acetate and/or propyl acetate.
  • the process further comprises removing water from the extract, preferably by evaporation under vacuum, to produce an aqueous extract having about 65° Bx (Brix).
  • the sugar cane derived product is selected from molasses, bagasse, first expressed juice, mill mud, clarified sugar juice, clarified syrup, treacle, golden syrup, field trash, cane strippings and/or dunder.
  • the sugar cane derived product is molasses or dunder, preferably molasses.
  • the sugar cane derived product is mixed with water in order to enable efficient and/or uniform mixing of the sugar cane product with ethanol to form the extraction mixture.
  • the sugar cane derived product comprises a mixture of water with a product selected from molasses, bagasse, first expressed juice, mill mud, clarified sugar juice, clarified syrup, treacle, golden syrup, field trash, cane strippings and/or dunder.
  • the sugar cane derived product comprises solid components, it may be desirable to first blend or homogenise the sugar cane derived product prior to mixing it with ethanol to form the extraction mixture.
  • the sugar cane derived product is bagasse, field trash and/or cane strippings blended or homogenised with water.
  • the skilled person can readily determine a suitable period of time for allowing the precipitate to form in the reaction mixture.
  • the precipitate is allowed to form for about 10 minutes to about 24 hours prior to removing the precipitate.
  • the extraction mixture is maintained at a temperature of about 20° C. to about 30° C.
  • the ethanol is removed from the supernatant by evaporation under vacuum.
  • the process is performed in batch. In an alternative embodiment, the process is performed in continuous flow.
  • the process further comprises subjecting the supernatant to membrane filtration and/or ion exchange, hydrophobic or size exclusion chromatography and collecting one or more flavonoid and/or polyphenol containing fractions to produce the extract derived from sugar cane.
  • the extract derived from sugar cane comprises a mixture of flavonoids and/or polyphenols. More preferably, the extract further includes components that exist with flavonoids and/or polyphenols in sugar cane including minerals, vitamins, carbohydrates, organic acids and/or fiber. More preferably, the extract comprises a mixture of flavonoids and/or polyphenols as glycones and aglycones.
  • the supernatant is subject to size exclusion membrane filtration or size exclusion chromatography.
  • the process further comprises subjecting the supernatant to ion exchange chromatography, hydrophobic interaction chromatography, liquid chromatography-mass spectrometry (LCMS) and/or matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) to produce the extract, preferably hydrophobic interaction chromatography.
  • LCMS liquid chromatography-mass spectrometry
  • MALDI-TOF matrix-assisted laser desorption/ionization-time of flight
  • the extraction mixture comprises about 70% to about 85% ethanol.
  • the extract comprises one or more of tricin, apigenin, luteolin, caffeic acid, hydroxycinnamic acids, sinapic acid, and derivatives thereof.
  • the extract produced by the process of the invention has reduced colour per unit concentration of polyphenols when compared to prior art compositions.
  • the colour of the extract may be analysed by measuring the absorbance of the supernatant at 420 nm.
  • the supernatant has an absorbance at 420 nm of about 800 to about 140 milliabsorbance (mAU) units.
  • the colour of the extract may also be analysed using the ICUMSA protocol.
  • the present invention provides an extract produced by the process of the invention.
  • the extract produced by the process of the invention comprises at least 25 mg/ml flavonoids and/or at least 25 mg/ml polyphenols.
  • the extract produced by the process of the invention comprises one or more of tricin, apigenin, luteolin, caffeic acid, hydroxycinnamic acids, sinapic acid, and derivatives thereof.
  • the extract produced by the process of the invention has ⁇ -glucosidase inhibitory activity and/or ⁇ -amylase inhibitory activity.
  • the extract produced by the process of the invention has anti-inflammatory activity.
  • the extract produced by the process of the invention has calorific value reduction properties and/or activity which slows the flux of carbohydrates, particularly monosaccharides, from the gut into the blood.
  • the extract also has glycemix index reduction properties.
  • the present invention provides an extract derived from sugar cane, wherein the extract comprises at least 25 mg/ml flavanoids, and/or at least 25 mg/ml polyphenols.
  • the extract derived from sugar cane comprises one or more of tricin, apigenin, luteolin, caffeic acid, hydroxycinnamic acids, sinapic acid, and derivatives thereof.
  • the extract derived from sugar cane has anti-inflammatory activity.
  • the present invention provides a composition comprising the extract of the invention.
  • the composition may include one or more additional active ingredients.
  • Active ingredients may include, but are not limited to, fucodian and arcabose. It is believed that such combinations may have a synergistic effect.
  • the present invention provides a food or beverage comprising the extract of the invention or the composition of the invention.
  • the food or beverage is selected from a bakery product, crystallised sugar, confectionary, breakfast cereal, naturally derived fiber, chemically derived fiber, dairy product, soft drink, water, coffee, cocoa, tea, or alcoholic beverage.
  • the food or beverage is a soft drink selected from a fruit juice containing beverage and a carbonated soft drink.
  • the food or beverage is selected from a bakery product, crystallised sugar, confectionary, breakfast cereal, naturally derived fiber, chemically derived fiber, diary product, soft drink, water, coffee, cocoa, tea, or alcoholic beverage.
  • the food is crystallised sugar.
  • the present invention provides a method of treating or preventing disease in a subject, the method comprising administering to the subject the extract of the invention, the composition of the invention, and/or the food or beverage of the invention.
  • the disease that is treated or prevented is diabetes and/or metabolic syndrome.
  • the diabetes is type II diabetes.
  • the diabetes is type I diabetes.
  • the present invention provides the extract of the invention, the composition of the invention, and/or the food or beverage of the invention, for use in the treatment or prevention of disease.
  • the present invention provides use of the extract of the invention, the composition of the invention, and/or the food or beverage of the invention in the manufacture of a medicament for the treatment or prevention of disease.
  • FIG. 1 Analysis of polyphenols, tricin and colour (A 420 nm) in ethanolic supernatant samples.
  • Sample 1 0% ethanol
  • sample 2 50% ethanol
  • sample 3 66% ethanol
  • sample 4 75% ethanol
  • sample 5 80% ethanol
  • sample 6 83% ethanol
  • sample 7 86% ethanol.
  • FIG. 2 Plot of % glucosidase inhibition vs. log 1.4 ⁇ g/ml for fucoidan (control), dunder (sample 6) and molasses (sample 3).
  • FIG. 3 Comparison of % PGE2 inhibition for aspirin (control), ibuprofen (control), dunder (sample 6) and molasses (sample 3).
  • FIG. 4 HPLC spectra of (a) Sample 1; (b) Sample 2; (c) Sample 3; (d) Sample 4; (e) Sample 5; (f) Sample 6; (g) phenolics at various retention times; and (h) flavonoids at various retention times.
  • FIG. 5 Plots of % polyphenol (PP) recovery vs. % ethanol and % colour removal vs. % ethanol of molassess feedstock samples having 25° Brix and 48° Brix.
  • x axis % ethanol;
  • y axis % polyphenol recovery and % colour removal.
  • administering as used herein is to be construed broadly and includes administering an extract or composition comprising the extract as described herein to a subject as well as providing an extract or composition comprising the extract as described herein to a cell.
  • treating include administering a therapeutically effective amount of an extract or composition comprising the extract as described herein sufficient to reduce or delay the onset or progression of a specified disease, or to reduce or eliminate at least one symptom of the disease.
  • the terms “preventing”, “prevent” or “prevention” include administering a therapeutically effective amount of an extract or composition comprising the extract sufficient to stop or hinder the development of at least one symptom of the specified condition.
  • dietary supplement as used herein is to be construed broadly and means a preparation or formulation which is added to or otherwise included in a subject's normal diet, and is present in addition to the normal diet.
  • a dietary supplement may be administered to a subject prior to, in conjunction with, or after consumption of a food or beverage.
  • sugar cane After being mechanically harvested, sugar cane is transported to a mill and crushed between serrated rollers. The crushed sugar cane is then pressed to extract the raw sugar juice, while the bagasse (leftover fibrous material) is typically used for fuel. The raw juice is then heated to its boiling point to extract any impurities, then lime and bleaching agents are added and mill mud is removed. The raw juice is further heated under vacuum to concentrate and increase Brix value. The concentrated syrup is seeded to produce bulk sugar crystals and a thick syrup known as molasses. The two are separated by a centrifuge and typically the molasses waste stream is collected for use as a low-grade animal feedstock.
  • bagasse leftover fibrous material
  • the extract produced according to the process of the invention can be derived from any sugar cane derived product, including those produced during the sugar cane milling process, the sugar cane refining process and other processes using sugar cane products.
  • sugar cane derived product refers to products of the sugar cane milling and refining processes including molasses, bagasse, first expressed juice, mill mud, clarified sugar juice, clarified syrup, treacle, golden syrup, field trash, cane strippings, growing tips, pulp and dunder.
  • sugar cane derived products comprise complex mixtures of substances including flavonoids, flavones, and polyphenols (Duarte-Almeida et al., 2006; Colombo et al., 2006; Payet et al., 2006; US 2012/0115941) as well as phytosterols, oligosaccharides, polysaccharides, mono and disaccharides, organic acids (e.g. cis and trans aconitic acid), peptides and proteins.
  • the type and amount of these components vary between the different sugar cane derived products. For example, molasses includes mono and disaccharides whereas dunder is almost free of sugar components.
  • Extracts that comprise complex mixtures of substances display improved characteristics compared with extracts of isolated components, such as tricin, luteolin or apigenin, or combinations of synthetic compounds.
  • Extracts according to the invention therefore can comprise one or more of tricin, apigenin, luteolin, caffeic acid, hydroxycinnamic acids, sinapic acid, and derivatives thereof. It is believed that natural biological mixtures can have a synergistic effect and may be better than synthetic or individually isolated natural products.
  • the sugar cane derived product is used as a feedstock and mixed with ethanol to form the extraction mixture.
  • Ethanol is used to extract a mixture of flavonoids and/or polyphenols.
  • the prior art uses ethanol to crash out impurities either in the extraction of sucrose or during the isolation of individual polyphenols (WO 2004/014159).
  • the rate of mixing the feedstock with ethanol may need to be controlled as well as the degree of mixing, ie homogeneity.
  • the sugar cane derived product may need to be mixed with a liquid, typically water, and/or heated in order to achieve a desired viscosity.
  • molasses is viscous at room temperature and, as a consequence, mixing of molasses and ethanol may be difficult to achieve consistently, efficiently or uniformly unless the viscosity of the molasses is adjusted.
  • the molasses may be mixed with water at a ratio of molasses to water of from about 75:25 to about 25:75. In one embodiment, the ratio of molasses to water is about 50:50.
  • the sugar cane derived product may be heated to decrease viscosity.
  • the sugar cane derived product may be heated to about 25° C. to about 60° C., more preferably about 25° C. to about 40° C., more preferably about 26° C. to about 30° C.
  • sugar cane derived products comprising solid material such as bagasse, field trash and cane strippings
  • the product is first blended or homogenised with water prior to mixing with ethanol to form the extraction mixture.
  • the amount of water with which the sugar cane derived product is blended or homogenised can be readily determined by the skilled person in order to achieve a sugar cane derived product having a suitable viscosity for mixing with ethanol to form an extraction mixture.
  • the sugar cane derived product will have a viscosity less than or equal to about 100 centipoise, more preferably between about 50 to about 100 centipoise.
  • the high viscosity of molasses is as a result of the high total solids (particularly soluble carbohydrates) and this is typically measured by determination of Brix degrees.
  • the sugar cane derived product will have about 20° to about 50° Brix.
  • Feedstocks with high Brix (>50°) behave differently to lower Brix feedstocks ( ⁇ 30°) with respect to the separation of polyphenols and colour by increasing levels of ethanol. This observation is crucial in both small and large scale separation processes.
  • the extraction mixture has a pH of about pH 4 to about pH 7.5.
  • the extract derived from the process of the invention may be used without further purification.
  • the extract may be subjected to purification, preferably hydrophobic interaction chromatography.
  • the purification step removes impurities, such as pigments that contribute to the colour of the extract.
  • the prior art uses chromatography to isolate fractions of individual polyphenols (WO 2004/014159).
  • the sugar cane derived product is mixed with ethanol to form an extraction mixture.
  • the present inventors have found that producing an extraction mixture comprising at least 50% v/v ethanol results in an increase in precipitate formation in the reaction mixture.
  • the retained supernatant advantageously has reduced colour and bitterness compared to a supernatant prepared from an extraction mixture comprising less than 50% v/v ethanol.
  • the extraction mixture comprises at least 50% v/v ethanol.
  • the extraction mixture comprises at least 51%, 52%, 53%, 54%, 55%, 56%, 57%, 58%, 59%, 60%, 65%, 70%, or 75% v/v ethanol, or at least 80%, 81%, 82%, 83%, 84% or 85 ethanol v/v.
  • the optimal concentration of ethanol in the extraction mixture for removing colour in the supernatant while minimising reduction in polyphenols is about 75% to about 85% v/v. Accordingly, in one embodiment, the extraction mixture comprises about 75% to about 85% v/v ethanol. In another embodiment, the extraction mixture comprises about 83% v/v ethanol.
  • the present inventors also found that while colour removal was substantially achieved with a reaction mixture comprising about 70% v/v ethanol, an extraction mixture comprising about 80% to about 83% v/v ethanol produced an extract that was stable and produced no precipitate over a 6 month period.
  • the extraction mixture comprises about 80% to about 83% v/v ethanol.
  • the precipitate may be removed from the mixture by any suitable method known in the art.
  • the precipitate may be removed by centrifugation and the supernatant obtained.
  • the precipitate may be allowed to settle for a time sufficient to allow the supernatant to be obtained while leaving precipitate behind, such as by sedimentation under gravity for example.
  • Other techniques such as filtration can be used alone or in combination with centrifugation or sedimentation in order to produce the extract derived from sugar cane.
  • the ethanol is removed using techniques known in the art.
  • the ethanol may be removed from the supernatant by evaporation, such as by using a rotary evaporator with a heating bath at approximately 45° C. or higher.
  • the process comprises multiple extractions.
  • a sugar cane derived product is mixed with ethanol to produce a preliminary extraction mixture (e.g., comprising at least about 25% v/v ethanol), a precipitate is allowed to form in the preliminary extraction mixture and the precipitate is removed from the preliminary extraction mixture to obtain a preliminary supernatant.
  • a preliminary extraction mixture e.g., comprising at least about 25% v/v ethanol
  • the preliminary supernatant is mixed with ethanol to produce a further extraction mixture comprising at least about 50% v/v ethanol, a precipitate is allowed to form in the further extraction mixture, the precipitate is removed from the further extraction mixture to obtain a further supernatant and ethanol is removed from the further supernatant to produce an extract derived from sugar cane.
  • Further ethanol can be added to a 50% extract supernatant to an ethanol level between 75-83% ethanol.
  • a further precipitate forms and can be recovered. The supernatant can become the final extract.
  • Separation of components in the supernatant or extract may also be achieved using chromatographic techniques or combinations of techniques such as ion exchange chromatography, hydrophobic interaction chromatography, such as for example on XAD or preferably a food grade resin such as FPX66 resin, which may use fractional elution by stepwise increase in pH or with suitable solvents, liquid chromatography-mass spectrometry (LCMS) and/or matrix-assisted laser desorption/ionization-time of flight (MALDI-TOF) to produce the extract.
  • LCMS liquid chromatography-mass spectrometry
  • MALDI-TOF matrix-assisted laser desorption/ionization-time of flight
  • the supernatants or extracts may be further processed by standard techniques such as but not limited to microfiltration, reverse osmosis, gel permeation, vacuum evaporation and freeze drying, spray drying and tunnel drying.
  • Sugar cane derived extracts according to the invention may be tested for biological activity using known techniques and assays.
  • an extract according to the invention can be tested for enzymatic activity.
  • the extracts may be tested for ⁇ -glucosidase inhibitory activity and/or ⁇ -amylase inhibitory activity.
  • ⁇ -glucosidase inhibitory activity can be measured as the ability of test samples to prevent the hydrolysis of 4-methylumbelliferyl- ⁇ -D-glucopyranosidase by yeast ( Saccharomyces cerevisiae ) ⁇ -glucosidase using known techniques.
  • yeast Saccharomyces cerevisiae
  • acarbose can be included in the assay as a positive control.
  • ⁇ -amylase inhibitory activity may be measured by the ability of samples to slow the rate at which porcine pancreatic amylase hydrolyses labelled starch (E-11954, Molecular Probes).
  • porcine pancreatic amylase hydrolyses labelled starch E-11954, Molecular Probes.
  • acarbose may be included in the assay as a positive control.
  • an extract according to the invention can also be tested for anti-inflammatory activity.
  • the extracts may be tested for prostaglandin E2 (PGE2) activity.
  • PGE2 inhibitory activity can be measured by the ability of test samples to inhibit PGE2 production in 3T3 cells when stimulated with calcium ionophore.
  • aspirin and ibuprofen may be included in the assay as a positive control.
  • the extracts produced according to the process of the invention can be used in a wide variety of economically useful applications.
  • an extract produced by the process of the invention is included in a food or beverage product.
  • Food or beverages according to the invention can be prepared by the skilled person using known techniques. Non-limiting examples of such food or beverage products are baked goods, dairy type foods and drinks, snacks, etc.
  • the amount of the extract to be used in a food or beverage can be variable as the extracts themselves are nutrients.
  • the extract may be used in any food or food product such as but not limited to sugar, for example crystallised sugar, confectioneries, snacks (sweet and savoury), cocoa-containing foods, flavours, dairy products including cheeses, butter, ice cream, yoghurt, and other dairy spreads; fat-based products including margarines, spreads, mayonnaise, shortenings, cooking and frying oils, and dressings; cereal-based and bakery products including breads and pastas whether these goods are cooked, baked or otherwise processed; confectioneries including chocolate, candies, chewing gum, desserts, non-dairy toppings, sorbets, icings and other fillings; and other miscellaneous food products including eggs and egg products, processed foods such as soups and pre-prepared pastas.
  • sugar for example crystallised sugar, confectioneries, snacks (sweet and savoury), cocoa-containing foods, flavours, dairy products including cheeses, butter, ice cream, yoghurt, and other dairy spreads
  • fat-based products including mar
  • the extract may be incorporated into or added to processed foods including but not limited to: breads, pastas, biscuits, sauces, soups, bars, dairy products (for example, milk, yoghurts, cheese, ice cream), cakes, ready-to-eat prepared meals, and breakfast cereals.
  • processed foods including but not limited to: breads, pastas, biscuits, sauces, soups, bars, dairy products (for example, milk, yoghurts, cheese, ice cream), cakes, ready-to-eat prepared meals, and breakfast cereals.
  • the extracts may be used in beverages, whether hot or cold including coffee, tea, cocoa, cereal, chicory and other plant extract based beverages, alcoholic or non-alcoholic beverages and including colas and other carbonated and non-carbonated soft drinks, fruit juices, juice drinks, dairy-based beverages, and meal replacement drinks.
  • the extracts may also be added to food grade ingedients such as soluble fiber (e.g. oligofructosaccharide), insoluble fiber (e.g. cocoa bean fiber, sugar cane fiber, oatbran), naturally derived fibers (e.g., hemicelluloses, lignocelluloses), chemically derived fibers (e.g., inulin), flour, starch, modified starch, gelatine, or other food, to produce a unique composition or ingredient with enhanced levels of polyphenols, flavonoids, and/or other phytochemicals derived from sugarcane.
  • soluble fiber e.g. oligofructosaccharide
  • insoluble fiber e.g. cocoa bean fiber, sugar cane fiber, oatbran
  • naturally derived fibers e.g., hemicelluloses, lignocelluloses
  • chemically derived fibers e.g., inulin
  • flour starch, modified starch, gelatine, or other food
  • the extract according to the invention is particularly useful for increasing the active phytochemical content of coffee products without increasing bitterness.
  • Roasting coffee beans causes the development of the myriad desired flavours of coffee.
  • the roasting also causes the bitter taste of coffee which is related to an increase in the level of the antioxidants, chlorogenic acid lactones and phenylindanes.
  • the extract of the invention can be used to increase the level of active phytochemicals (such as polyphenols) in coffee products.
  • the food or beverage of the present invention can include additional ingredients including an orally ingestible diluent or carrier.
  • an orally ingestible diluent or carrier are known in the food sciences. These include, but are not limited to, manufactured cereals, fruit or vegetable products, beverages or beverage concentrates, ground meat products or vegetable analogues thereof, and any inert diluent, carrier, or excipient known in the pharmaceutical art.
  • the extract produced according to the process of the invention may be added to or included in a nutritional supplement.
  • a “nutritional supplement” is an orally ingestible product consumed to improve overall nutrition, health, well-being, or performance of a subject in an activity and/or an orally ingestible product which provides additional perceived nutritional or biological benefit to a subject.
  • the nutritional supplement may be provided in a concentrated form, thus allowing for the addition of the nutritional supplement to a food or drink product to allow for the consumption of a desired quantity of an extract of the invention in a reasonable serving size.
  • the nutritional supplement is a sports nutrition product.
  • the extract may be added to a sports nutrition product including, by way of non-limiting examples, sports powders, sports drinks, energy drinks, pre-mixes, juices, energy bars, energy gels, isotonic drinks and gelatine, starch based or pectin jellies.
  • the nutritional supplements and sports nutrition products of the current invention can include additional ingredients.
  • more than one of the extracts of the current invention can be included in the same nutritional supplement or sports nutrition formulation.
  • Other additional ingredients include any ingestible product.
  • Preferred additional ingredients include, but are not limited to, other active food supplement ingredients such as micro-nutrients such as vitamins and minerals or macro-nutrients such as polyunsaturated fatty acids or fiber.
  • the food additive may also include acceptable dispersing and suspending agents, and water.
  • Other conventional nutritional supplements can also be included if desired.
  • the nutritional supplement or sports nutrition product can take many forms including, but not limited to, powders, liquids, tablets, capsules, solutions, concentrates, syrups, suspensions, or dispersions.
  • the glycaemic index or GI ranks carbohydrates according to their effect on blood glucose levels. The lower the GI, the slower the rise in blood glucose level will be when the food is consumed. Some research has shown that by eating a diet with a lower GI, people with diabetes, for example, can reduce their average blood glucose levels. This is important in reducing the risk of developing diabetes-related complications.
  • GI rating To determine a food's GI rating, measured portions of the food containing 10-50 grams of carbohydrate are fed to at least 10 healthy people after an overnight fast. Finger-prick blood samples are taken at 15-30 minute intervals over the next two hours. These blood samples are used to construct a blood sugar response curve for the two hour period. The area under the curve (AUC) is calculated to reflect the total rise in blood glucose levels after eating the test food. The GI rating (%) is calculated by dividing the AUC for the test food by the AUC for the reference food (usually glucose or white bread) and multiplying by 100. A GI value of 55 or less is considered ‘low’, 56-69 is considered “medium” and over 70 is “high”.
  • a lower glycemic index suggests slower rates of digestion and absorption of carbohydrates and is believed to equate to a lower insulin demand, better long-term blood glucose control and a reduction in blood lipids. It has been shown that individuals who followed a low GI diet over many years were at a significantly lower risk for developing both type 2 diabetes and associated conditions such as cataracts as well as coronary heart disease. High blood glucose levels or repeated glycemic “spikes” following a meal may promote these diseases by both increasing oxidative damage to the vasculature and via the direct increase in insulin levels. Postprandial hyperglycemia has been considered a risk factor mainly associated with diabetes but it is now that it also presents an increased risk for atherosclerosis and other conditions in the non-diabetic population.
  • Low-GI foods by virtue of their slow digestion and absorption, produce gradual rises in blood sugar and insulin levels and have been shown to improve both glucose and lipid levels in people with diabetes (type 1 and type 2) and have benefits for weight control as they help control appetite and delay hunger. Low GI diets also reduce insulin levels and insulin resistance.
  • the extracts produced according to the process of the present invention may be used in food or beverages, for example, to lower or reduce the GI of the food or beverage.
  • the extracts according to the present invention in the form of a liquid extract can be sprayed onto standard sugar (whether derived from sugar cane or sugar beets) to produce a low GI sugar.
  • the extracts according to the present invention in the form of a liquid extract can also be sprayed onto other carriers such as flour, starch, bagasse or fiber thus increasing the levels of polyphenols and/or flavonoids in these food ingredients.
  • Endogenous and “adsorbed” polyphenols and other sugarcane phytochemicals use the fibers to protect these compounds from early metabolic changes in the gut and increase delivery to specific sites in the colon where these compounds reduce inflammation and other disease processes including cyclooxygenase enzymes involved with intestinal carcinogenesis or polyp formation (Cai et al.).
  • the available calorific value of a food or beverage relates to the amount of energy available from the food or beverage when digested.
  • chocolate is a low-GI food, it contains a high number of calories and therefore has a high available calorific value as determined by conventional methods including bomb calorimetry.
  • the extracts according to the present invention in the form of a liquid extract can be sprayed onto standard sugar (whether derived from sugar cane or sugar beets) to produce a reduced available calorific value sugar (sucrose).
  • standard sugar whether derived from sugar cane or sugar beets
  • sugar beets a reduced available calorific value sugar
  • the extracts according to the present invention in the form of a liquid extract can also be sprayed onto other carriers such as flour, starch or fiber thus increasing the levels of polyphenols and/or flavonoids in these food ingredients.
  • a powder such as a freeze dried powder or dehydrated powder, can be used in place of a liquid extract.
  • dietary calories are derived from carbohydrate. Approximately half are from simple sugars (glucose, fructose, sucrose, lactose, maltose and trehalose) with the remainder coming from complex carbohydrates (hemicelluloses, galactans, mannans and starch). Complex carbohydrates other than starch are referred to as dietary fiber which is either partly or totally digested in the large intestine.
  • the digestion of dietary carbohydrates is a physiologically regulated process in the gastrointestinal tract.
  • Important enzymes in this process include salivary and pancreatic ⁇ -amylase and intestinal ⁇ -glucosidase. Beginning in the mouth, food is chewed and mixed with salivary ⁇ -amylase. Starch released begins to break down immediately. This hydrolysis process slows or stops in the stomach because of the change in pH but resumes again in the duodenum where pancreatic ⁇ -amylase is secreted. The result is to produce maltose and maltotriose from amylase and maltose, maltotriose, glucose and dextrin from amylopectin.
  • the principal enzymes responsible for the breakdown of carbohydrates in the human body are ⁇ -amylase and ⁇ -glucosidase and so inhibition of one or both of these enzymes can result in the GI of foods being reduced.
  • the extracts of the invention which demonstrate inhibition of the activity of ⁇ -glucosidase and ⁇ -amylase in vitro will delay carbohydrate absorption in vivo, thus reducing post-prandial increase in blood glucose.
  • the extracts of the invention are able to lower the GI of a food or beverage.
  • pharmaceutically acceptable carrier is intended to include any and all solvents, dispersion media, coatings, antibacterial and antifungal agents, isotonic and absorption delaying agents, and the like, compatible with pharmaceutical administration.
  • the use of such media and agents for pharmaceutically active substances is well known in the art. Except insofar as any conventional media or agent is incompatible with the active compound, such media can be used in the compositions of the invention. Supplementary active compounds can also be incorporated into the compositions.
  • the current extract is higher in concentration (polyphenols (mg)/extract (ml)) of polyphenols and lower in colour relative to other extracts from sugar, the extracts are “more effective” in delivering a therapeutic amount of biologically active compounds.
  • concentration polyphenols (mg)/extract (ml)
  • extracts are “more effective” in delivering a therapeutic amount of biologically active compounds.
  • the lower colour and organoleptic astringency of some syrups prepared according to the present invention broaden their possible use and application in a range of foods and carriers.
  • the final volume was 200 ml.
  • a 1 ml sample was removed and diluted with 1 ml water, mixed well and then a drop was placed on a Ella refractometer.
  • the Brix reading was 48.
  • the feedstock (200 ml) was placed in a glass beaker on a magnetic stirrer and adjusted so that a clear vortex was formed, ethanol was slowly added into the vortex to ensure rapid mixing of the feedstock with the ethanol. Over a period of about 30 minutes, 950 ml of ethanol was added. The temperature was maintained at 26-28° C. This resulted in the final ethanol level in the mixture being 83% v/v. The mixture was stirred for another 30 minutes. A number of sub-samples were taken during the addition of the ethanol to support the observations as the solution changed in colour and different coloured precipitates formed as the ethanol % increased.
  • the final mixture was turbid and had a coagulated black gelatinous precipitate visibly present in the bottom of the beaker.
  • the supernatant was removed and centrifuged at 4000 rpm (2500 ⁇ g), for 5 minutes. The clear yellow supernatant was decanted leaving the black precipitate plug in the centrifuge tube. About 950 ml of the mixture was centrifuged and the final volume of supernatant recovered was 880 ml.
  • Ethanol was removed using a Buchi rotary evaporator under vacuum. The bath temperature was 45° C. The final concentrate (free of any ethanol odour) volume was 62 ml and the Brix level was 64-65. Ethanol, its azeotroph and water were all removed during this process.
  • the final bioactive extract was a dark/yellow colour, free of any particulate material and with a fresh sweet flavour similar to that of golden syrup or treacle.
  • the supernatant was recovered in the same way as described in Example 1.
  • the volume was 1050 ml.
  • Table 5 lists the samples tested. Each sample (0.5 mL) was weighed and freeze-dried to determine its % dry matter. The samples were then resuspended in either dimethyl sulfoxide (DMSO) or DMSO:water (1:1) to a concentration of 15 mg/mL, after which the samples were serially diluted.
  • DMSO dimethyl sulfoxide
  • the reaction was stopped by the addition of 100 mM sodium glycine buffer (100 ⁇ L, pH 10.6), the plate was shaken for a further 30 seconds, and the fluorescence intensity was measured at ⁇ ex 355 nm and ⁇ en 460 nm. Fucoidan was used as a positive control and sodium acetate buffer (pH 5.5) was used as a negative control.
  • the in vitro production of PEG2 from 3T3 cells was measured using the Cayman Chemical Prostaglandin E2 monoclonal EIA (Enzyme Immuno Assay) kit.
  • the cells were exposed to samples 3 and 6 and stimulated with calcium ionophore.
  • the cell supernatants were then assayed for PEG2 production.
  • the cell cytotoxicity of the samples was tested against 3T3 cells to confirm that the observed PEG2 inhibition was not due to cell cytotoxicity.
  • Aspirin and ibuprofen were used as positive controls.
  • sample 3 and sample 6 The highest PEG2 inhibition observed for sample 3 and sample 6 was 29.90% and 42.33%, respectively, at 0.488 ⁇ g/mL. As shown in FIG. 3 , the PEG2 inhibitory response of sample 6 was similar to that of ibuprofen (42.14% at 0.488 ⁇ g/mL). Inhibition of PEG2 production in the cells, relative to control cells not exposed to the samples, indicates that the samples act as an anti-inflammatory agent in vitro.
  • the resin is then washed with an alkaline pH 12-13 solution which removes the bound polyphenols and flavonoids, and this effluent is adjusted to pH 6.5 to 7.0 with acid or preferably it is passed through an acidic resin column to “exchange” the alkali for H + ions so the effluent pH is less than 7. This process was reproduced in the laboratory on a small scale.
  • Liquid chromatography profiles of polyphenols were monitored initially in the affination liquor (pH 5.0-6.0) and then in the alkaline resin extracts (pH 12-13) and then after adjusting these extracts (pH 6.5-7.0).
  • Polyphenols are extremely sensitive to high pH conditions forming flavones. Such changes can modify the bioactivity of these compounds and even reversing the pH from alkaline to neutral does not necessarily return them to their previous bioactive properties.
  • Liquid chromatography fingerprints from-alkaline pH 12-13 extracts were significantly different to fingerprints from the same extracts but adjusted to pH 6.5-7.0. A number of major peaks in the alkaline extracts seemed to have shifted to lower elution times on the chromatogram, possibly reflecting the structural change to flavones. When the pH of these alkaline extracts was adjusted to neutral pH, the peaks shifted to longer elution times and aligned themselves with peaks obtained from the original liquor feedstock.
  • the present inventors have surprisingly found that colour can be removed efficiently without significant loss of polyphenols. When ethanol concentration was increased beyond 40% a more suitable extract was produced.
  • Sample 1 Townsville Terminal Molasses, which has been clarified by centrifugation.
  • the crude molasses (about 75 Brix) was adjusted to 25 Brix with water and centrifuged (4,000 rpm for 10 mins). The precipitate was discarded.
  • the initial clarified feedstock was still 25 Brix and used to produce a 75% ethanol supernatant, which is Sample 2.
  • 200 ml of this clarified feedstock was used to make the 75% super extract.
  • Total CE/100 g 808 mg.
  • Sample 4 This 75% super was made by initially removing the 50% precipitate, recovering the 50% super and then adding more ethanol to 75%. Precipitate removed, 75% super recovered and ethanol removed. The final volume was 80 ml and it was 32 Brix.
  • Sample 5 Hydrophobic chromatography extract of Sample 4.
  • FPX66 material recovered from 15 ml of Sample 4. The peak removed with 70% ethanol was bulked (aliquots were combined) and the ethanol removed. Final volume was 25 ml.
  • Sample 6 Hydrophobic chromatography extract of Sample 2.
  • FPX66 material recovered from 15 ml of Sample 2. The peak removed with 70% ethanol was bulked (aliquots were combined) and the ethanol removed. Final volume was 40 ml.
  • FIG. 4 shows the HPLC fingerprints of the samples as well as some spectra of unidentified phenolics and flavonoids at various retention times.
  • the present inventors also observed that, when molasses is diluted to 25 Brix and then 48 Brix and extraction is broken into two stages, the colour of the final extract is lower and polyphenol recovery is higher. Therefore, an extraction method to produce a standardised extract is as set out in FIG. 6 .

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JP7356253B2 (ja) * 2019-04-09 2023-10-04 Ｄｍ三井製糖株式会社 骨代謝改善剤
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US11730178B2 (en) 2023-08-22
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PH12015500408B1 (en) 2015-04-20
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EP3569298A1 (en) 2019-11-20
AU2013308395C1 (en) 2018-03-15
US20190183149A1 (en) 2019-06-20
US20220279820A1 (en) 2022-09-08
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