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WO2024173525A1 - Composition filmogène comprenant du pullulane et un glucane - Google Patents

Composition filmogène comprenant du pullulane et un glucane Download PDF

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Publication number
WO2024173525A1
WO2024173525A1 PCT/US2024/015759 US2024015759W WO2024173525A1 WO 2024173525 A1 WO2024173525 A1 WO 2024173525A1 US 2024015759 W US2024015759 W US 2024015759W WO 2024173525 A1 WO2024173525 A1 WO 2024173525A1
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WO
WIPO (PCT)
Prior art keywords
glucan
composition according
range
film
composition
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.)
Ceased
Application number
PCT/US2024/015759
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English (en)
Inventor
Yefim Brun
Laurie HOWE
Slavko Kralj
Stephanie ROBART
Jin Zhao
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Nutrition and Biosciences USA 1 LLC
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Nutrition and Biosciences USA 1 LLC
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Publication of WO2024173525A1 publication Critical patent/WO2024173525A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/4816—Wall or shell material

Definitions

  • the present invention is directed to aqueous film-forming compositions suitable for capsule films, capsule shells, as wells as methods for producing such capsule film, capsule shell and the use thereof.
  • Capsules are widely used in administration of pharmaceuticals and nutritional to humans and animals. Capsules also have divergent uses, such as serving as reservoirs of plant fertilizer for easy application, of colorants, of food materials or food supplements, and of cosmetic ingredients. Pullulan is a convenient material for the film part of the capsule because pullulan film can be formed on the capsule pins in the process of preparing the capsule with the aid of gelling agents.
  • Pullulan capsules are natural, clean label, potentially organic certifiable and have very low oxygen permeation. Pullulan capsules become a desirable alternative to gelatin capsules and HPMC capsules in today's consumer demands.
  • the common gelling agent carrageenan used with pullulan capsules has a perception of being an unsafe material and consumers demand carrageenan-free products.
  • pullulan capsules with carrageenan as a setting system tend to dissolve differently when pH, salt concentration, protein concentration changes in the digestive tract.
  • Another common gelling agent, gellan gum tend to have more pH dependency than those of capsules made with carrageenan.
  • FIG. 1 Synthesis of B-1,3 glucan using a three-enzyme system, Using sucrose phosphorylase, laminaribiose phosphorylase and laminaridextrin phosphorylase.
  • Figure 3 A comparison of statistical analysis of normalized puncture force for pullulan film and the film made with blend of pullulan and p-1,3 glucan (Exp806 as shown in Table 4).
  • Figure 4 A comparison of statistical analysis of normalized puncture strength for pullulan film and the film made with blend of pullulan and p-1,3 glucan (Exp0122 as shown in Table 1).
  • the present invention relates in a broad aspect to aqueous film-forming compositions suitable for improved or alternative capsule materials.
  • the present invention relates to an aqueous film-forming composition
  • an aqueous film-forming composition comprising a) one or more water-soluble, film forming polysaccharide(s) having a MW above about 15 kDA which polysaccharide(s) comprises units selected from the group consisting of glucose, fructose, and galactose units, which units are bound together by glycosidic bonds; and b) a 0-1,3-glucan having a MW in the range from about 1 to about 15 kDa.
  • the present invention relates to a capsule shell comprising an aqueous film-forming composition
  • a capsule shell comprising an aqueous film-forming composition
  • which composition comprises: a) one or more water-soluble, film forming polysaccharide(s) having a MW above about 15 kDA which polysaccharide(s) comprises units selected from the group consisting of glucose, fructose, and galactose units, which units are bound together by glycosidic bonds; and b) a -1,3-glucan having a MW in the range from about 1 to about 15 kDa.
  • the present invention relates to a capsule comprising a capsule shell prepared from the composition of the invention or a capsule shell according to the invention.
  • the present invention relates to a process for producing capsule film or capsule shells comprising the steps of providing the aqueous composition according to the invention, pre-heating moulding pins to a temperature at highest viscosity point ⁇ 5 °C of the aqueous composition above the gelation temperature, dipping the pre-heated moulding pins into the aqueous composition at a temperature below gelation temperature, forming a film on said moulding pins by withdrawing said pins from said composition, and drying the film on the moulding pins above the gelation temperature.
  • the present invention relates to the use of a composition according to the invention for the manufacture of capsules in a dip moulding process, such as a hot dipping pins process.
  • a natural polymer 0-1,3 glucan
  • polysaccharide(s) having a MW above about 15 kDA
  • polysaccharide(s) comprising units of glucose, fructose, and galactose units, such as pullulan, which may be used for capsules.
  • the same concept will apply for glucan based capsules potentially using a-1,6 glucan or enzymatically made pullulan-like materials (a-1,6 - a-1,4 glucan branched with majority of either a-1,6 or a- 1,4) and 0-1,3 glucan which will impart gelling properties that facilitate hard capsule manufacturing.
  • the commercial high MW 0-1,3 glucan (curdlan, ⁇ 2000 kDa) is not soluble in cold water due to the existence of extensive intra/intermolecular hydrogen bonds.
  • the 0-1,3 glucan suitable for use in the compositions of the present invention is typically around 2 kDa with approximately 15 glucose units.
  • the present inventors have identified three major components in 0-1,3 glucan. It was found that the component 2 preferably should be > 70%, wherein component 3 preferably should be ⁇ 30% to impart the optimal film performance.
  • an aqueous film-forming composition comprising a) one or more water-soluble, film forming polysaccharide(s) having a MW above about 15 kDA which polysaccharide(s) comprises units selected from the group consisting of glucose, fructose, and galactose units, which units are bound together by glycosidic bonds; and b) a 0-1,3-glucan having a MW in the range from about 1 to about 15 kDa.
  • the 0-1,3-glucan is thermo reversible in water.
  • the 0-1,3-glucan has a MW in the range from about 1 to about 14 kDa, such as from about 1 to about 12 kDa, preferably in the range of from about 1 to about 10 kDa, and more preferably in the range of from about 1 to about 5 kDa, and most preferably in the range of from about 2 to about 4 kDa.
  • the 0-1,3-glucan comprises glucose units in the range from about 5 to about 1000 glucose units such as glucose units in the range from about 5 to about 300 glucose units, preferably glucose units in the range from about 7 to about 100 glucose units, more preferably in the range of glucose units in the range from about 9 to about 50 glucose units, and most preferably in the range of from about 12 to about 20 glucose units.
  • the 0-1,3-glucan is unbranched.
  • the 0-1,3-glucan is prepared by an enzymatic reaction using a 0-1,3- glucan phosphorylase or a 0-1,3-glucan synthase.
  • the -1,3-glucan is derived from algae, fungi, plants or bacteria.
  • the p-l,3-glucan is selected from the group consisting of callose, laminarin, and paramylon.
  • the >70% by weight of the total amount of p-l,3-glucan has a degree of polymerization (DP) above 9, more preferably >80% by weight of the total amount of 0-1,3-glucan has DP above 11, and most preferably >90% by weight of the total amount of 0-1,3-glucan has a DP above 12 .
  • DP degree of polymerization
  • the water-soluble film forming polysaccharide is selected from the group consisting of starch, pullulan, and glucan such as a-glucan.
  • the water-soluble film forming polysaccharide is an enzymatically produced polysaccharide.
  • the water-soluble film forming polysaccharide is derived from algae, fungi, plants or bacteria.
  • the water-soluble film forming polysaccharide is pullulan. In some embodiments the pullulan is enzymatically produced.
  • the water-soluble film forming polysaccharide is an a-glucan, preferably a-l,6-glucan with a-1,2 branches; a-l,6-glucan with a-1,3 branches or a-1,4 glucan with a-1,6 branches.
  • the water-soluble film forming polysaccharide has a solution viscosity in the range from about 500 cps to about 5000 cps at temperatures in the range of about 5 °C to about 80 °C with solution concentration within the range of about 10 wt% to about 40 wt% .
  • composition according to invention is essentially free from cations such as mono- or divalent cations.
  • the final film composition comprises less than 5%, preferably less than 3%, most preferably less than 1% of sugar molecules (such as glucose, fructose, sucrose, and glucose-l-phosphate) by weight of dry film basis.
  • sugar molecules such as glucose, fructose, sucrose, and glucose-l-phosphate
  • the concentration of the water-soluble film forming polysaccharide, such as pullulan is at least about 80%, such as at least about 82%, such as at least about 85%, such as at least about 87%, such as at least about 90% by weight of dry film basis. In some embodiments the concentration of the water-soluble film forming polysaccharide, such as pullulan is at least about 80-95%, such as in the range of 82-95%, such as 85-90, such as 87-90% by weight of dry film basis.
  • the concentration of 0-1,3-glucan is at least about 0.1%, such as at least about 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, or 9.0% by weight of dry film basis.
  • the concentration of 0-1,3-glucan is not more than about 9.0, such as not more than about 8.5, 8.0, 7.5, 7.0, 6.5, 6.0, 5.5, 5.0, 4.5, 4.0, 3.5, 3.0, 2.5, 2.0, 1.8, 1.6, 1.4, 1.2, 1.0, 0.8, 0.6, such as in the range of 0.1-10.0%, such as 0.2-8.0%, such as 0.4-6.0%, such as 0.6-4.0%, such as 0.8-4.0%, such as 1.0-4.0% by weight of dry film basis.
  • the composition according to invention is further comprising a plasticizer, wherein the plasticizer is a polyol, such as a sugar alcohol, such as sorbitol, mannitol, erythritol, xylitol, or glycerol (Propane-1, 2, 3-triol), or acetate esters of glycerol selected from the class consisting of the mono-, di-, and tri-acetates of glycerol, TEC (triethyl citrate), dibutyl sebacate, and dibutyl phthalate, or mixtures thereof.
  • a plasticizer is a polyol, such as a sugar alcohol, such as sorbitol, mannitol, erythritol, xylitol, or glycerol (Propane-1, 2, 3-triol), or acetate esters of glycerol selected from the class consisting of the mono-, di-, and tri-acetates of glyce
  • composition according to invention is additionally comprising at least one ingredient selected from the group consisting of surfactants, such as simethicone, sodium lauryl sulfate, lecithin, sorbitan esters; coloring agents, flavoring agents, or mixtures thereof.
  • surfactants such as simethicone, sodium lauryl sulfate, lecithin, sorbitan esters
  • coloring agents such as coloring agents, flavoring agents, or mixtures thereof.
  • 0-1,3-glucans consist of glucose polymers with variable molecular weight (MW).
  • This present invention concerns aqueous compositions comprising a 0-1,3-glucan having a MW in the range from about 1 to about 15 kDa.
  • a 0-1,3-glucan has a degree of polymerization (DP) and it is to be understood that when the 0-1,3-glucan is made enzymatically the distribution of components with different degree of polymerization can be "manipulated", e.g. by enzyme dose, temperature etc.
  • the present inventors have identified three major components in 0-1,3 glucan, which components differ in DP and in MW.
  • the ratio of the largest MW component of 0-1,3-glucan with a degree of polymerization (DP) above 9 to be used in an aqueous film-forming composition according to the present invention is preferably above 70%.
  • Any suitable film forming polysaccharide(s) having a MW above about 15 kDa which polysaccharide(s) comprises units selected from the group consisting of glucose, fructose, and galactose units, which units are bound together by glycosidic bonds may be used for the film of the present invention.
  • the person skilled in the art will know these suitable polymers.
  • Suitable film forming polymer used according to the present invention includes starch, pullulan, and glucan such as o-glucan, such as an o-l,6-glucan with a-1,2 branches; an a- 1,6-glucan with a-1,3 branches or an a-1,4 glucan with a-1,6 branches.
  • o-glucan such as an o-l,6-glucan with a-1,2 branches; an a- 1,6-glucan with a-1,3 branches or an a-1,4 glucan with a-1,6 branches.
  • Suitable film forming polymer used according to the present invention can be naturally derived (without chemical modification via chemical methods that involve additional chemicals that are not naturally derived, i.e., non-microbial or non-enzymatic methods) or enzymatic synthesized.
  • Suitable film forming polymer used according to the present invention may be naturally derived and purified from a suitable species including from algae, fungi, plants or bacteria.
  • plasticizer examples include surfactants such as sucrose fatty acid ester, glycerin fatty acid ester, monoglycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester and the like, ester of citric acid such as triethyl citrate (TEC); polyhydric alcohol such as glycerin, propylene glycol, polyethylene glycol, etc., glucose , Sugar such as fructose and glucose liquid sugar, sugar such as sucrose, sugar alcohol such as sorbitol, maltitol, mannitol, erythritol, xylitol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, Higher alcohols such as hexadecyl alcohol, isostearyl alcohol, 2- octyldodecanol and the like (preferably
  • Enzyme reactions were performed at 37 °C.
  • Table 1 Composition of B-1,3 glucan batches produced, using LEI 2183, CRC 12031 and CRC 12027 in a one pot reaction.
  • the samples (SK-018 and SK-019) were dissolved in distilled water at 50 °C on a heater shaker for 2 hours. Each sample was prepared at two concentration levels, 1.5 and 1.8 mg/mL, respectively. The samples were filtered by 0.45 pm Nylon syringe filters prior to analyses.
  • the samples were analyzed by a chromatograph consisting of Agilent G7111B pump, G7129A autosampler, G7116A column oven, and G7162A refractive index detector (RI).
  • the samples were injected to a column (Tosoh TSKgel G2500PW) maintained at 35 °C.
  • the RI detector was set at 35 °C as well.
  • the eluent was water with 0.05 wt% NaN3.
  • the flow rate was at 0.5 mL/min.
  • the injection volume was 0.1 mL.
  • the chromatograms in Figure 2 were obtained by subtracting the blank (distilled water) chromatogram from sample chromatograms.
  • the SEC elution time of component 2 of the two samples are compared in Table 3.
  • the elution time of component 2 in SK-018 is slightly lower than that in SK-019 suggesting that the MW of the component is slightly higher in SK-018.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
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Abstract

La présente invention concerne des compositions filmogènes aqueuses appropriées pour des films de capsule, des enveloppes de capsule, ainsi que des procédés de production d'un tel film de capsule, d'une telle enveloppe de capsule et leur utilisation.
PCT/US2024/015759 2023-02-14 2024-02-14 Composition filmogène comprenant du pullulane et un glucane Ceased WO2024173525A1 (fr)

Applications Claiming Priority (2)

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US202363484842P 2023-02-14 2023-02-14
US63/484,842 2023-02-14

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WO2024173525A1 true WO2024173525A1 (fr) 2024-08-22

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2663294A2 (fr) * 2011-01-11 2013-11-20 Capsugel Belgium NV Nouvelles gélules dures comprenant du pullulane
WO2016096344A1 (fr) * 2014-12-15 2016-06-23 Unilever Plc Compositions pour fournir une protection d'écran solaire améliorée
WO2019209559A1 (fr) 2018-04-23 2019-10-31 Danisco Us Inc Synthèse de glucane comprenant des liaisons glycosidiques bêta-1,3 avec des enzymes phosphorylase
WO2020023278A1 (fr) 2018-07-23 2020-01-30 Danisco Us Inc Synthèse d'alpha-glucose-1-phosphate à partir de la synthèse de saccharose et de glucane à l'aide de glucane phosphorylases

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2663294A2 (fr) * 2011-01-11 2013-11-20 Capsugel Belgium NV Nouvelles gélules dures comprenant du pullulane
WO2016096344A1 (fr) * 2014-12-15 2016-06-23 Unilever Plc Compositions pour fournir une protection d'écran solaire améliorée
WO2019209559A1 (fr) 2018-04-23 2019-10-31 Danisco Us Inc Synthèse de glucane comprenant des liaisons glycosidiques bêta-1,3 avec des enzymes phosphorylase
WO2020023278A1 (fr) 2018-07-23 2020-01-30 Danisco Us Inc Synthèse d'alpha-glucose-1-phosphate à partir de la synthèse de saccharose et de glucane à l'aide de glucane phosphorylases

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
CHANG JINYU ET AL: "Preparation, properties, and structural characterization of [beta]-glucan/pullulan blend films", INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, ELSEVIER BV, NL, vol. 140, 27 August 2019 (2019-08-27), pages 1269 - 1276, XP085927521, ISSN: 0141-8130, [retrieved on 20190827], DOI: 10.1016/J.IJBIOMAC.2019.08.208 *
M. KITAOKAT. SASAKIH. TAMIGUCHI, ARCH. BIOCHEM. BIOPHYS, 1993
ROBERT PYLKKÄNEN: "[beta]-1,3-Glucan synthesis, novel supramolecular self-assembly, characterization and application", NANOSCALE, vol. 14, no. 41, 27 October 2022 (2022-10-27), United Kingdom, pages 15533 - 15541, XP093165153, ISSN: 2040-3364, Retrieved from the Internet <URL:https://pubs.rsc.org/en/content/articlepdf/2022/nr/d2nr02731c> DOI: 10.1039/D2NR02731C *

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