EP1339432A1 - Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras - Google Patents

Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras

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Publication number
EP1339432A1
EP1339432A1 EP01994752A EP01994752A EP1339432A1 EP 1339432 A1 EP1339432 A1 EP 1339432A1 EP 01994752 A EP01994752 A EP 01994752A EP 01994752 A EP01994752 A EP 01994752A EP 1339432 A1 EP1339432 A1 EP 1339432A1
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EP
European Patent Office
Prior art keywords
molecular inclusion
fatty acids
water
inclusion compound
linear
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP01994752A
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German (de)
English (en)
Inventor
Stephan Hausmanns
Thomas Kiy
Dirk Fabritius
Ivan Tomka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Celanese Ventures GmbH
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Celanese Ventures GmbH
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Publication date
Application filed by Celanese Ventures GmbH filed Critical Celanese Ventures GmbH
Publication of EP1339432A1 publication Critical patent/EP1339432A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
    • 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
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
    • A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof

Definitions

  • the present invention relates to molecular inclusion compounds from biocatalytically prepared, water-insoluble, linear polysaccharides and from fatty acids or their derivatives, processes for their preparation and their use.
  • Microcapsules are either in finely divided dispersions in which the material to be encapsulated is embedded in a sponge-like matrix (e.g. R94-9400419), or in structures in which the material to be encapsulated is not penetrated by the capsule material, but only surrounded (e.g. Arshady et al. 1990, Polymer Eng. Sci., 30 (15), 905-914 and 915-924).
  • the compound to be encapsulated is part of the multimolecular aggregates. It is also known that starch components such as amylose and amylopectin can also be used to form the above microcapsules.
  • microcapsules primarily serve to protect the encapsulated material against external influences (e.g. heat, UV light, oxidation), but can also make a significant contribution to easier processing (e.g. flowability, stickiness, conversion of liquid products into solid products).
  • Another application of the microcapsules is oral application while influencing sensory properties.
  • native starches can be used to form microcapsules (MK).
  • starches with a high proportion of resistant starches (high RS content) are used, which are only fermentatively degraded in the large intestine and not, as usual, by pancreatic amylase in the stomach and small intestine.
  • complex compounds of the iodine-starch complex type have also been described, in which one or more iodine or fatty acid molecules are embedded in a starch helix (cf. FIG. 1). This complex is referred to below as the molecular inclusion compound.
  • Helical iodine-starch complexes and their use for medical and pharmaceutical application are described, for example, by Gehnt and Eskin in US Pat. No. 5,955,101.
  • WO 94/17676 describes a composition of hydrolyzed starch as a matrix for incorporated lipophilic compounds.
  • a combination of molecular inclusion and dispersion is proposed in DE 44 11 414.
  • a product for the enteral supply of fatty acids is disclosed in which these are present in the product in a proportion of at least 10%.
  • the fatty acid is finely dispersed in a plasticized starch matrix, some of the fatty acids being at least partially enclosed in an amylose helix.
  • amylose helix it is not clear what the corresponding percentage of fatty acid molecules molecularly included in the amylose helix is.
  • Molecular inclusion compounds are therefore known which are based on native and thus branched, water-soluble starch or their degradation products and in which, according to common, professional knowledge, a maximum of 4.6% by weight of fatty acid, based on the starch content, can be incorporated as a molecular inclusion compound (also: loading) (see also Example 4 and Krüger et al., Monthly Bull. Brauwiss. (1984) 37 (12) pp. 505-512). Fanta et al. describe the complexation (loading) of 4.6% by weight myristic acid in amylose-rich starch (Carbohydr. Polym. (1999) 38 (1) pp. 1-6). However, materials and processes that would allow a molecular inclusion of significantly higher amounts of fatty acids (higher loading) would be desirable.
  • Molecular inclusion compounds are particularly well suited for use in pharmaceutical preparations, as functional foods, in cosmetic preparations and as food additives, and as food supplements, since the included compounds are very good, for example, against molecular influences such as e.g.
  • the fields of application of such molecular inclusion compounds also depend very much on the properties of the materials used for the inclusion.
  • the materials used are ⁇ -amylase resistant, so that the molecular inclusion compounds according to the invention are only digested in the large intestine. This can prevent the enzymatic / hydrolytic degradation of the molecular inclusion compound from occurring faster, based on the entire digestion process. It is particularly advantageous if the lipophilic molecules present in the interior of the molecular inclusion compounds are only released in the large intestine, so that they can be directly absorbed by the cells of the intestinal wall, without first being enzymatically involved, for example, by pancreatic enzymes split or modified. As a result, the bioavailability of the compounds can be increased in a particularly favorable manner.
  • a further object of the present invention was to provide molecular inclusion compounds and processes for their production, in which the materials used for the inclusion have new properties which open up new fields of application or special advantages in use for molecular inclusion compounds. It was also an object of the present invention to provide improved molecular inclusion compounds and processes for their preparation which, owing to the materials used, can be used as a constituent of human or veterinary compositions, as a food and feed constituent and for cosmetic applications.
  • a molecular inclusion compound characterized in that it consists of at least (a) a biocatalytically produced, linear, water-insoluble polysaccharide and (b) one (one) or more (more) fatty acid (s) or fatty acid derivative (s) ) consists.
  • An object of the present invention is therefore monomolecular inclusion compounds from biocatalytically produced, water-insoluble, linear polysaccharides and helically complexed lipophilic molecules, e.g. Fatty acids or their esters, the amount of helically complexed lipophilic compound being at least 5% by weight, based on the polyglucan used.
  • the amount of helically complexed lipophilic compound is preferably at least 7% by weight, based on the polysaccharide used, particularly preferably more than 9% by weight, based on the polysaccharide used, very particularly preferably more than 10% by weight, based on the polysaccharide used.
  • linear, water-insoluble polysaccharides are homogenized in a mixture with a lipophilic compound and processed to form a homogeneous matrix. Any unbound excess of the lipophilic compound is then removed by extraction.
  • a plasticizer can also be added. Homogenization can be brought about, for example, by extrusion. It is clear to the person skilled in the art that further, for example taste-improving, appearance-influencing or, in general, processability-influencing substances can be added.
  • Preferred plasticizers according to the invention are odorless, colorless, light, cold and heat resistant, only slightly or not at all hygroscopic, water-resistant, not harmful to health, difficult to ignite and as little volatile as possible, neutral reaction, miscible with polymers and auxiliaries and have good gelling behavior on. In particular, they should be compared to the used components have compatibility, gelling ability and softening effectiveness.
  • plasticizers examples include water, polyalcohols such as ethylene glycol, glycerol, propanediol, erythritol, maitol, sorbitol, polyvalent alkanoic acids such as maleic acid, succinic acid, adipic acid, polyvalent hydroxyalkanoic acids such as lactic acid, 2-hydroxybutyric acid, citric acid, malic acid, dimethyl or other solvents, urea for strength.
  • polyalcohols such as ethylene glycol, glycerol, propanediol, erythritol, maitol, sorbitol
  • polyvalent alkanoic acids such as maleic acid, succinic acid, adipic acid
  • polyvalent hydroxyalkanoic acids such as lactic acid, 2-hydroxybutyric acid, citric acid, malic acid, dimethyl or other solvents, urea for strength.
  • plasticizers are preferably used in a proportion of 2% by weight to 50% by weight, based on the polysaccharide component of the mixture according to the invention.
  • fragrance or aroma substances, binders etc. can be added if, for example, a cosmetic or pharmaceutical use or a use as a food or nutritional component is intended.
  • the degree of loading of native starch in palmitic acid which cannot be washed out with chloroform is 2-3% by weight. Surprisingly, this proportion increases to 7.7% by weight in the molecular inclusion compound according to the invention using biocatalytically prepared, linear and water-insoluble 1,4- ⁇ -D-polyglucan as polysaccharide.
  • the fatty acid is only released from the molecular inclusion compound after degradation by suitable enzymes or chemical hydrolysis under suitable conditions and can then be reisolated.
  • Linear, water-insoluble polysaccharides in the context of the present invention are polysaccharides which are built up from monosaccharides, disaccharides or other monomeric units in such a way that the monosaccharides, disaccharides or other monomeric units are always linked to one another in the same way.
  • Each basic unit or building block defined in this way has exactly two links, one each to a different monomer. From that except for the two basic units that form the beginning and the end of the polysaccharide. These basic units have only one link to another monomer. With three links on a basic unit (covalent bonds) one speaks of a branch.
  • Linear, water-insoluble polysaccharides in the sense of the invention have no branches or at most only to a minor extent, so that the very small branch fractions cannot be detected using conventional analytical methods such as, for example, 13 C or 1 H NMR spectroscopy.
  • DAß German Pharmacopoeia, Scientific Publishing House mbH, Stuttgart, Govi-N erlag GmbH, Frankfurt, 9th edition, 1987
  • Water-insoluble polysaccharides preferred according to the invention can therefore be assigned to class 4 of the DASS, that is to say that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 30 to 100 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 30-100 ml water).
  • Water-insoluble polysaccharides which are more preferred according to the invention can be assigned to class 5 of the DAB, ie that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 100 to 1000 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 100-1000 ml water).
  • even more preferred water-insoluble polysaccharides can be assigned to class 6 of the DAB, ie that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 1000 to 10000 parts by volume of solvent, ie water, per part by weight of substance (1 g substance per 1000-10000 ml water).
  • the most preferred water-insoluble polysaccharides can be assigned to class 7 of the DAB, that is to say that a saturated solution of the polysaccharide at room temperature and normal pressure comprises about 10,000 to 100,000 parts by volume of solvent, ie water, per part by weight of substance (lg substance per 10000-100000 ml water).
  • sparingly soluble to practically insoluble polysaccharides especially very sparingly soluble to practically insoluble polysaccharides, are preferred.
  • It is preferably water-insoluble poly- ⁇ -1,4-D-glucan.
  • linear, water-insoluble polysaccharides which have been produced in a biocatalytic (synonym: biotransformer) or a fermentative process are preferred.
  • Linear polysaccharides produced by biocatalysis in the context of this invention means that the linear polysaccharide is produced by catalytic reaction of basic monomeric units such as oligomeric saccharides, for example mono- and / or disaccharides, using a so-called biocatalyst, usually an enzyme , is used under suitable conditions.
  • Biocatalysis can be carried out with living, growing cells, with cells in the stationary state, with immobilized cells, with isolated or genetically engineered soluble or immobilized enzymes, in a single or multi-phase system.
  • Linear polysaccharides from fermentations are, in the parlance of the present invention, linear polysaccharides which have been modified by fermentative processes using organisms which occur in nature, such as fungi, algae or bacteria, or using organisms which are not found in nature with the aid of genetic engineering methods of general definition natural organisms such as fungi, algae or bacteria can be obtained or can be obtained with the help of fermentative processes.
  • linear polysaccharides according to the present invention can also be other polyglucans or other linear polysaccharides such as pullulans, pectins, mannans or polyfructans.
  • linear polysaccharides for the preparation of the molecular inclusion compounds described in the present invention can also be obtained from the reaction of further non-linear polysaccharides by treating non-linear polysaccharides containing branches with an enzyme in such a way that they are used to cleave the Branching occurs, so that linear polysaccharides are present after their separation.
  • enzymes can be, for example, amylases, iso-amylases, Act gluconohydrolases or pullulanases.
  • the polysaccharides according to the invention should always be strictly linear.
  • the polysaccharide used is 1,4- ⁇ -D-polyglucan.
  • the 1,4- ⁇ -D-polyglucan is preferably produced by means of a biocatalytic (biotransformatory) process with the aid of polysaccharide synthases, starch synthases, glycosyltransferases, -1,4-glucantransferases, glycogen synthases, amylosucrases or phosphorylases.
  • the molecular weights Mw of the linear polysaccharides used according to the invention can vary within a wide range from 10 3 g / mol to 10 7 g / mol.
  • molecular weights Mw of 10 4 g / mol to 10 5 g / mol, in particular 2 ⁇ 10 4 g / mol to 5 ⁇ 10 4 g / mol are preferred.
  • the ⁇ -amylase-resistant polysaccharides according to the invention can be characterized in that the 1,4- ⁇ -D-polyglucans are chemically modified in a manner known per se.
  • 1,4- ⁇ -D-polyglucans may have been chemically modified by etherification or esterification in the 2-, 3- or 6-position.
  • the person skilled in the art is sufficiently familiar with this chemical modification; see. for example the following literature:
  • an RS content is understood to mean the content of ⁇ -amylase-resistant polysaccharides as it is according to the method of Englyst et al. (Classification and measurement of nutritionally important starch fractions, European Journal of Clinical Nutrition, 46 (Suppl. 23) (1992) 33-50).
  • the molecular inclusion compounds described in the present invention have a high degree of resistance to ⁇ -amylase compared to native starch.
  • the ⁇ -amylase-resistant inclusion compounds according to the invention are characterized in that an RS content according to Englyst is at least 30, preferably 50, particularly preferably 75 and very particularly preferably 95% by weight ,
  • biocatalytically produced, linear and water-insoluble polysaccharides which can be used according to the invention have a whole series of features both of native strength and of those described in the prior art Distinguish enzymatic "debris products" of native starch. A summary of such differences is given in Table 1 below.
  • the inventors mentioned above currently assume that the surprisingly high binding capacity of the inclusion compounds according to the invention compared to inclusion compounds from the prior art cannot be attributed to a single one of these substance characteristics, but rather the sum of these Properties, possibly the strict linearity of the molecules according to the invention and the lack of phosphate esters and the high water insolubility in their entirety are responsible for the fact that the inclusion compounds according to the invention have such surprisingly favorable properties. Since the linear 1,4-D-polyglucan can be a more resistant form compared to the native starch (RS> 30%), this has advantages in the oral application of compounds which have their effect only after the passage of the Should ignite stomach and small intestine.
  • lipophilic agents can only be released specifically in the large intestine.
  • lipophilic substances which can be used according to the invention are saturated fatty acids or unsaturated fatty acids, so-called PUFAs.
  • PUFAs (English: Poly-Unsaturated Fatty Acids; German: polyunsaturated fatty acids) are understood in the parlance of the present invention as fatty acids with a chain length of more than 12 carbon atoms with at least two double bonds (see Table 2).
  • the fatty acids can be used both in the form of the free fatty acids, as fatty acid esters, as physiologically acceptable salts of the fatty acids, as triglycerides or in the form of other derivatives.
  • these fatty acids can be protected against premature digestion in the digestive system.
  • polysaccharide component of the mixture according to the invention can also be a mixture of different biocatalytically produced, water-insoluble and linear polysaccharides.
  • Figure 1 shows a schematic representation of the molecular inclusion compound.
  • A Process of binding a fatty acid into the polysaccharide helix;
  • B Fully stored fatty acid.
  • Figure 2 shows X-ray spectra for poly- ⁇ -l, 4-D-glucan with 35% glycerol (1) and additionally 2.5% (2), 5% (3) and 10% (4) palmitic acid.
  • the biotransformation supernatant is denatured at 95 ° C. After cooling to room temperature, centrifugation was carried out again. The clear supernatant was frozen at -70 ° C and thawed at 4 ° C for 3 days. The precipitate thus generated was frozen at -70 ° C and freeze-dried.
  • 39.5 g of the solid are washed with water for 30 min with stirring at room temperature, frozen at -70 ° C. and freeze-dried.
  • the fructose and sucrose content is determined after dissolving the solid in DMSO by a coupled enzymatic assay according to Stitt et al. (Meth. Enzym., 174 (1989) 518-552) and is 2.27 mg fructose per 100 mg solid.
  • the sucrose content is below the detection limit.
  • a mixture of 200g poly- ⁇ -l, 4-D-glucan (material from Example 1), 70g glycerol and 5g, 10g, 20g or 30g palmitic acid (corresponds to 2.5%, 5%, 10% or 15% based on the weight fraction of the polyglucan) are initially charged and homogenized in the extruder at 170 ° C. and 100 rpm. Samples are taken from the product after cooling. The melting peaks of the samples are determined using DSC (Digital Scanning Calorimetry). The degree of complexation Kx is then determined with the aid of a Soxhlet extraction (chloroform, 48h) by dissolving out the uncomplexed palmitic acid.
  • Table 3 shows results of a Soxhlet extraction in which native starch (purified potato starch) was used instead of poly- ⁇ -1,4-D-glucan in the sample preparation according to Example 1.
  • Table 3 Results of DSC and Soxhlet extraction
  • Example 3 The samples described in Example 3 were subjected to an X-ray structure analysis.
  • X-ray spectra for poly- ⁇ -l, 4-D-glucan with 35% glycerol (1) and 5 additionally 2.5% (2), 5% (3) and 10% (4) palmitic acid are shown in FIG. 2. It can be seen that the spectrum for the pure, plasticized poly- ⁇ -1,4-D-glucan (1) from the amorphous halo, the three larger peaks at 13.7, 15.5 and 21.1 ° 2 ⁇ , as well as some smaller peaks. The reflections at 13.7 and 21.1 ° are characteristic of the simple helix of V-amylose, a structure type that is typical of complex starches.

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Abstract

L'invention concerne des composés d'inclusion moléculaires caractérisés en ce qu'ils sont au moins constitués (a) d'un polysaccharide linéaire insoluble dans l'eau, fabriqué de manière biocatalytique, et (b) d'un ou plusieurs acides gras ou dérivés d'acides gras. Ces composés d'inclusion moléculaires sont particulièrement adaptés à une utilisation dans des préparations pharmaceutiques, en tant qu'aliments fonctionnels, dans des préparations cosmétiques, en tant qu'additifs alimentaires, et en tant que compléments alimentaires étant donné que les composés inclus sont par exemple très bien protégés contre les influences moléculaires telles que l'attaque enzymatique.
EP01994752A 2000-11-30 2001-11-29 Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras Withdrawn EP1339432A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10059726 2000-11-30
DE10059726 2000-11-30
PCT/EP2001/013971 WO2002043768A1 (fr) 2000-11-30 2001-11-29 Composes d'inclusion moleculaires constitues de polysaccharides lineaires insolubles dans l'eau fabriques de maniere biocatalytique et d'acides gras ou de derives d'acides gras

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EP1339432A1 true EP1339432A1 (fr) 2003-09-03

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CN101155636B (zh) * 2005-02-07 2011-07-27 江崎格力高株式会社 含有α-1,4-葡聚糖的吸附剂及其制备方法
WO2009023159A1 (fr) * 2007-08-10 2009-02-19 Iowa State University Research Foundation Amidons alimentaires résistants et procédés associés
JP5572323B2 (ja) * 2009-03-04 2014-08-13 備前化成株式会社 包摂反応においてホスト化合物の選択性を高める低分子多糖類、およびそれを用いた苦味成分および臭い成分を包摂する方法
AR086993A1 (es) 2011-06-20 2014-02-05 Gen Biscuit Masa de galletita
CN114522635B (zh) * 2022-01-24 2023-08-25 华南理工大学 一种具有可控释放肉桂醛的抗菌微胶囊及其制备方法

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IL113776A (en) * 1994-05-18 2008-12-29 Bayer Bioscience Gmbh Dna sequences coding for enzymes which catalyze the synthesis of linear alpha 1,4 - glucans in plants, fungi and microorganisms
JP2913010B2 (ja) * 1995-03-09 1999-06-28 農林水産省食品総合研究所長 有機溶媒可溶化リパーゼを用いる糖質−脂肪酸複合体の製造方法
DE19852826A1 (de) * 1998-11-17 2000-05-18 Aventis Res & Tech Gmbh & Co Poly(alpha-1,4-D-Glucan)

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