• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    PROCESS FOR THE EXTRACTION OF MATERIALS FROM BIOLOGICAL MATERIAL. The invention concerns a process for extracting materials from biological material, which process is characterized in that the naturally occurring biological material is treated with an extraction solvent consisting of a deep eutectic solvent of natural origin or an ionic liquid of natural origin for produce a biological extract of natural origin dissolved in said solvent or ionic liquid.
    公开号:BR112012031167B1
    申请号:R112012031167-0
    申请日:2011-06-07
    公开日:2021-07-06
    发明作者:Jacob van Spronsen；Geert-Jan Witkamp；Frank Hollman；Young Hae Choi；Robert Verpoorte
    申请人:Universiteit Leiden；
    IPC主号:
    专利说明:

    [001] The present invention concerns a process to extract materials from biological materials.
    [002] Medicines, flavorings, fragrances, agrochemicals, dyes etc., both from synthetic and natural sources are often poorly soluble in water. Therefore, extraction, purification and administration require the use of less polar solvents such as alcohols, acetone, ethyl acetate, chloroform etc. Such solvents present several problems such as: toxicity for the producer/patient/consumer, environmental problems, explosions and the like.
    [003] Ionic liquids can be environmentally benign and safe replacements for traditional volatile organic solvents in various chemical processes. The reason ionic liquids are considered 'green' solvents is their negligible vapor pressure. However, ionic liquids can have a hidden environmental cost because they are synthesized from petrochemical resources. In many synthetic pathways, halogen atoms are involved. Halogen materials in ionic liquids are undesirable due to their low hydrolysis stability, high toxicity, biodegradability and high selling cost. For example, fluorinated anions such as PF6- and BF4- are sensitive to water and can release corrosive and toxic hydrogen fluoride. Furthermore, the alkyl halides used in the syntheses of many ionic liquids are greenhouse gases and ozone-depleting materials.
    [004] The reason ionic liquids are also considered safe solvents is because their lack of volatility greatly reduces any possibility of exposure other than through direct physical contact with the skin or by ingestion. However, most conventional ionic liquids are irritating and have comparable toxicity to common organic solvents. From biological tests it appeared that the toxicity of ionic liquids is primarily determined by the type of cation and that ionic liquids with small alkyl substituents on the cation typically have less toxicity.
    [005] A solution to the aforementioned problems is the development of ionic liquids without halogen, such as ionic liquids with the alkyl sulfate, the alkyl carbonate and the sulfonate anion. It has also been observed that some ionic liquids with ester groups in their alkyl side chains are biodegradable. However, these ionic liquids are still synthesized using petrochemical resources.
    [006] In WO2006/116126 is described a process to extract biopolymers from biomass, using ionic liquids. In general, the ionic liquids described therein are petrochemical in nature. The extracted biopolymers are chitin, chitosan, collagen and keratin. Polyhydroxyalkanoate is extracted from genetically engineered plants.
    [007] As indicated above, there is a need for an improved process to extract organic compounds from natural sources, without the need to use organic solvents or other synthetic materials.
    [008] Additionally, there is a need for a process that can truly be considered “green”, that is, using only natural compounds.
    [009] The invention is based on the surprising fact that some specific naturally occurring materials can suitably be used to extract materials from biological sources. These materials are deep eutectic solvents (or mixtures) of natural origin or ionic liquids of natural origin.
    [0010]Deep eutectic solvents are liquids with a melting point that is much lower than the melting points of the two compounds that make up the eutectic mixture. They are usually formed between a variety of quaternary ammonium salts and carboxylic acids. The deep eutectic phenomenon was first described in 2003 for a mixture of choline chloride and urea in a 1:2 molar ratio, respectively. Other deep eutectic choline chloride solvents are formed with phenol and glycerol. Deep eutectic solvents can dissolve many metal salts such as lithium chloride and copper(II) oxide. Also, organic compounds such as benzoic acid and cellulose have great solubility in deep eutectic solvents. Compared to ordinary solvents, eutectic solvents have a very low volatility and are non-flammable. They share many characteristics with ionic liquids, but they are mixtures of ionic and non-ionic compounds.
    [0011]Instead, choline citrate is a real ionic liquid. This compound was formed by dissolving citric acid in water, followed by addition of choline hydroxide (in the ratio 2:1) dissolved in methanol. The solvent (water and methanol) was evaporated. The choline citrate product was a slightly yellow viscous liquid, not a solid. This is probably the first naturally occurring ionic liquid observed.

    [0012] In addition to ions, sugar-based liquids can be deep eutectic solvents.
    [0013] According to the invention, a process is provided for extracting materials from biological material, which process is characterized in that the naturally occurring biological material is treated with a solvent for extraction consisting of a deep eutectic solvent of natural origin or a ionic liquid of natural origin to produce a biological extract of natural origin dissolved in said solvent or ionic liquid.
    [0014] Surprisingly, it has been observed that deep eutectic solvents of natural origin as defined herein and natural ionic liquids are suitable extraction solvents for biological materials. These extraction solvents are very efficient and selective, and as they are of natural origin, they are extremely efficient and suitable for extracting components from biological materials, resulting in an efficient process providing a good yield. Melting points of deep eutectic mixtures and ionic liquids are preferably below 25°C. The materials are thus preferably liquid at ambient temperatures.
    [0015]Deep eutectic solvents suitable to be used in the present invention, i.e. mixtures of materials of natural origin, are based on mixtures of at least two compounds, substantially without chemical or ionic bonding. The first component of the solvents is preferably selected from at least one naturally occurring organic acid or an inorganic compound, such as a salt.
    The second component is preferably selected from at least one naturally occurring mono or dimeric sugar, sugar alcohol, amino acid, di or tri alkanol or choline derivatives such as choline or phosphatidyl choline.
    [0017] Said sugar or sugar alcohol may be selected from the group of sucrose, glucose, fructose, lactose, maltose, cellobiose, arabinose, ribose, ribulose, galactose, rhamnose, raffinose, xylose, sucrose, mannose, trehalose, mannitol, sorbitol, inositol, ribitol, galactitol, erythritol, xylitol and adonitol, as well as their phosphates.
    [0018] Said organic acid can be selected from malic acid, maleic acid, citric acid, lactic acid, pyruvic acid, fumaric acid, succinic acid, lactic acid, acetic acid, aconitic acid, tartaric acid, malonic acid, acid ascorbic, glucuronic acid, oxalic acid, neuraminic acid and sialic acids.
    [0019] In general, it is preferred that the ionic liquid or deep eutectic solvent be chlorine/chloride free.
    [0020] In certain solvents, additionally additional components may be present, such as water, phenolics, etc. These additional compounds are generally present in smaller amounts, such as below 5% by weight.
    [0021] Suitable examples of inorganic compounds are phosphates, sulfates, sulfites and halides, such as NaH2PO4, Na2HPO4, NaHSO3, Na2SO4, CaCl2, MgCl2, KCl, NaCl and KI.
    [0022] Specific examples of deep eutectic solvents are given in the table below, but also honey, syrup and nectar are examples of deep eutectic solvents that can be used as extraction solvent (which are based on sugar, and small amounts of phenolics and amino acids).
    Deep eutectic mixture of malic acid with choline chloride
    Deep eutectic mixture of maleic acid with choline chloride
    [0023] Suitable ionic liquids are based on naturally occurring anions selected from the group of malic acid, maleic acid, citric acid, lactic acid, tartaric acid, glucosamine, glucuronic acid, neuraminic acid and sialic acids.
    [0024] Said ionic liquid is additionally based on naturally occurring cations selected from the group of choline, betaine, betanin, gamma-aminobutyric acid, betalain, acetylcholine, glucosamine, glutamine, glutamate, asparagine, aspartic acid, alanine, lysine , arginine, proline, threonine, putrescine, cadaverine and choline derivatives.
    [0025] In a more preferred embodiment said ionic liquid is choline citrate.
    [0026] The ratio of the components of deep eutectic solvents and ionic liquids depends on the structure of two or more constituents of the solvent or liquid.
    [0027] For deep eutectic solvents very often the two components are present in an equimolar ratio, although other reasons have also been noted. Generally, however, the molar ratio can be expressed in whole numbers. These ratios generally range from 1:1 to 4:1.
    [0028]Ionic liquids are by definition anions and salt cations and thus the ratio is determined by the valence of the ions.
    [0029] In the following tables 1 and 2 the composition and properties of deep eutectic solvent (des) were given, as well as some solubility data. Table 1: The composition and properties of deep eutectic solvent (des)

    Ala = alanine Ch = cholineFru = fructoseGlc = glucoseGly = glycerolLact - lactoseMa = malic acid1,2Pro = 1,2-propanediolPro = prolineSo = sorbitolSuc = sucroseXo = xylitolXyl = xyloseTable 2: Summary of some solubility data in some Typical Typical at 40 °C (mg/ml) (n=3)

    [0030] The present invention relates to materials for extracting biological products. In most of the general scope, all materials of biological origin can be used. Suitable examples are plants, insects, animals or microorganisms.
    [0031] From these materials a wide variety of products can be isolated using the process of the present invention. More in particular, the extracted or dissolved material is a flavonoid (eg rutin and quercetin), an anthrocyanin, a dye, an alkaloid, a terpenoid, a phenylpropanoid, a glycoside, a phenolic compound such as cinnamic acid, a ginkgolide, cartamine, an anthraquinone, paclitaxel, taxnoid, a lignan, a coumarin, a cinnamic acid derivative, azadirachitin, artimisinin, a hop bitter acid, a cannabinoid, vanillin, a polyketide, a dye, a flavoring, a fragrance, a dye, a biocide or a mixture of any of these compounds. Also proteins (enzymes), toxins, vaccines, DNA, RNA and polysaccharides can be extracted from the appropriate sources.
    [0032]In particular, the invention concerns the extraction of natural materials from natural sources, that is, not genetically modified. In a further preferred embodiment, valuable materials are thus extracted or dissolved, such as non-polymeric compounds, in the manner listed above. Non-polymeric compounds are defined as compounds that do not consist of three or more repeating units of the same fraction (monomer) or the same type of monomers, such as amino acids or sugars.
    [0033] These non-polymeric materials are, for example, suitable intermediates or suitable products in food, pharmaceutical, cosmetic and agrochemical substances. More in particular, it is preferable to extract flavorings and fragrances from the plant, vanillin from vanilla, capsaicin from Capsicum, hop hop bitter acid, marijuana cannabinoids, azadiraquitin from Neem plant material, paclitaxel from Taxus plant material, artimisinin from plant material. Artemisia plant, Catharanthus alkaloids, morphine and codeine from Papaver plant material, atropine and hyoscyamine from Solanacea plant material, galantamine from Amaryllidaceae plants, plant material antioxidants, microorganism antibiotics, plant dyes and micro- organisms, flavonoids from plant materials, anthrocyanins and carotenoids from flowers, an essential oil from a plant.
    [0034] In another modality, specific polymeric compounds are extracted or dissolved, such as RNA, DNA, protein materials such as enzymes, toxins, vaccines, but excluding keratin, elastin and collagen, or polysaccharides, excluding chitin and chitosan. Preferred polysaccharides to be extracted or dissolved are lentinan, heparin, hyaluronan, alginate, agar, starch and inulin. Extracted materials can subsequently be isolated from the ionic liquid or deep eutectic solvent. It is also possible to use the solution as such for additional processes. An example of this is the use of extracted enzymes dissolved in the ionic liquid or eutectic solvent in enzymatic reactions. These reactions are then carried out in said solvent or liquid. An example is the laccase reaction.
    [0035] The invention is now elucidated on the basis of the following examples.
    [0036]First the solubility of natural products, which are not soluble in water, was evaluated in some selected natural deep eutectic solvents. Several flavonoids were chosen as the water-insoluble natural products because they are one of the most abundant water-insoluble plant secondary metabolites. So far more than 500 flavonoids have been known. Most of these flavonoids occur in their glycoside forms (attached to a sugar molecule) in plants. Despite the great abundance of flavonoids in plants, both the glycoside and the aglycon (non-sugar) part are not soluble in water. Thus, as a research model, the solubility of typical flavonoids including quercetin (aglycone), quercetin (quercetin-3-O-rhamnoside) and rutin (quercetin-3-O-rhamnoside), which have very low solubility in water , has been tested in naturally occurring deep eutectic solvents. The structure of these flavonoids is shown below.
    Quercetin, quercitrin and rutin structures (left to right)
    [0037] As shown in the following table, it was observed that the three flavonoids were well dissolved in the natural deep eutectic solvents, with solubilities that are 2 to 4 orders of magnitude higher compared to their solubilities in water.Table 3: Flavonoid solubility in various naturally occurring deep eutectic solvents

    [0038] In order to confirm the solubility of flavonoids and related anthrocyanins, red rose flowers were extracted in the naturally occurring ionic liquids. It was observed that the red colored metabolites are located in the epidermis cells.
    [0039] Extraction with the deep eutectic solvent fructose/glucose/malic acid (1:1 molar ratio) resulted in the removal of color from these flowers in the deep eutectic solvent phase. The structure of the flowers remained intact, without any disruption of the natural structure.
    权利要求:
    Claims (10)
    [0001]
    1. Process for extracting materials from biological material, in which the biological material is based on plants, insects, animals or microorganisms, which process is CHARACTERIZED by the fact that naturally occurring biological material is treated with a solvent to extraction consisting of a deep eutectic solvent of natural origin to produce a biological extract of natural origin dissolved in said solvent, wherein the deep eutectic solvent is based on a combination of (i) at least one naturally occurring organic acid and ( ii) at least one naturally occurring mono- or dimeric sugar, sugar alcohol, amino acid or di or tri alkanol, or in which the deep eutectic solvent is based on fructose, glucose, sucrose and water, or lactose, glucose and Water; and wherein the extracted material is a polymeric or non-polymeric compound.
    [0002]
    2. Process, according to claim 1, CHARACTERIZED by the fact that said biological extract of natural origin is a non-polymeric compound, which can be used as an intermediate or product in food, pharmaceutical, cosmetic or agrochemical applications.
    [0003]
    3. Process according to claim 1, CHARACTERIZED by the fact that said biological extract of natural origin is a polymeric compound selected from the group of RNA, DNA, proteins, toxins, vaccines and polysaccharides, with the proviso that keratin, elastin, collagen, chitin and chitosan are excluded.
    [0004]
    4. Process according to any one of claims 1 to 3, CHARACTERIZED by the fact that the deep eutectic solvent is based on a combination of at least one naturally occurring organic acid and at least one naturally occurring mono- or dimeric sugar , sugar alcohol, amino acid, di or tri alkanol.
    [0005]
    5. Process, according to any one of claims 1 to 4, CHARACTERIZED by the fact that said sugar or sugar alcohol is selected from the group of sucrose, glucose, fructose, lactose, maltose, cellobiose, arabinose, ribose, ribulose, galactose, rhamnose, raffinose, xylose, sucrose, mannose, trehalose, mannitol, sorbitol, inositol, xylitol, ribitol, galactitol, erythritol and adonitol, as well as their phosphates.
    [0006]
    6. Process according to any one of claims 1 to 5, CHARACTERIZED by the fact that said organic acid is selected from malic acid, maleic acid, citric acid, lactic acid, pyruvic acid, fumaric acid, succinic acid, acetic acid , aconitic acid, tartaric acid, ascorbic acid, malonic acid, oxalic acid, glucuronic acid, neuraminic acid and sialic acid.
    [0007]
    7. Process according to any one of claims 1 to 6, CHARACTERIZED by the fact that additional water is present in said solvent for extraction.
    [0008]
    8. Process according to any one of claims 1 to 7, CHARACTERIZED by the fact that said deep eutectic solvent of natural origin has a melting point below 25 °C.
    [0009]
    9. Process according to any one of claims 1 to 8, CHARACTERIZED by the fact that the extracted material is recovered from said solvent.
    [0010]
    10. Process according to any one of claims 1 to 9, CHARACTERIZED by the fact that the extracted material is a flavonoid (for example, rutin and quercetin), an anthocyanin, a dye, an alkaloid, a terpenoid, a phenylpropanoid, a glycoside, a phenolic compound such as cinnamic acid, a ginkgolide, cartamine, an anthraquinone, paclitaxel, a taxoid, a lignan, a coumarin, a cinnamic acid derivative, azadirachitin, artimisinin, a hop bitter acid, a cannabinoid, vanillin, a polyketide, a dye, a flavoring, a fragrance, a pigment, a biocide, or a mixture of any of these compounds.
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    法律状态:
    2018-01-23| B07D| Technical examination (opinion) related to article 229 of industrial property law [chapter 7.4 patent gazette]|
    2018-04-10| B06F| Objections, documents and/or translations needed after an examination request according [chapter 6.6 patent gazette]|
    2019-01-29| B07G| Grant request does not fulfill article 229-c lpi (prior consent of anvisa) [chapter 7.7 patent gazette]|Free format text: NOTIFICACAO DE DEVOLUCAO DO PEDIDO POR NAO SE ENQUADRAR NO ART. 229-C DA LPI. |
    2019-11-26| B06U| Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette]|
    2020-11-17| B07A| Technical examination (opinion): publication of technical examination (opinion) [chapter 7.1 patent gazette]|
    2021-05-11| B09A| Decision: intention to grant [chapter 9.1 patent gazette]|
    2021-07-06| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 07/06/2011, OBSERVADAS AS CONDICOES LEGAIS. PATENTE CONCEDIDA CONFORME ADI 5.529/DF, QUE DETERMINA A ALTERACAO DO PRAZO DE CONCESSAO. |
    优先权:
    申请号 | 申请日 | 专利标题
    NL2004835A|NL2004835C2|2010-06-07|2010-06-07|Process for extracting materials from biological material.|
    NL2004835|2010-06-07|
    PCT/NL2011/050407|WO2011155829A1|2010-06-07|2011-06-07|Process for extracting materials from biological material|
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