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WO2016010093A1 - Procédé de production de composite contenant de la curcumine amorphe et/ou un analogue de celle-ci - Google Patents

Procédé de production de composite contenant de la curcumine amorphe et/ou un analogue de celle-ci Download PDF

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Publication number
WO2016010093A1
WO2016010093A1 PCT/JP2015/070318 JP2015070318W WO2016010093A1 WO 2016010093 A1 WO2016010093 A1 WO 2016010093A1 JP 2015070318 W JP2015070318 W JP 2015070318W WO 2016010093 A1 WO2016010093 A1 WO 2016010093A1
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WIPO (PCT)
Prior art keywords
curcumin
analog
hydroxypropylcellulose
hydroxypropylmethylcellulose
complex
Prior art date
Application number
PCT/JP2015/070318
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English (en)
Japanese (ja)
Inventor
厚 今泉
瞳 小澤
壮 佐藤
高橋　司
崇人 松井
悠治 牧野
千惠子 加藤
Original Assignee
株式会社セラバリューズ
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Publication date
Application filed by 株式会社セラバリューズ filed Critical 株式会社セラバリューズ
Priority to JP2016534477A priority Critical patent/JPWO2016010093A1/ja
Publication of WO2016010093A1 publication Critical patent/WO2016010093A1/fr

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    • 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
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/12—Ketones
    • 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
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38—Cellulose; Derivatives thereof

Definitions

  • the present invention relates to a method for producing a complex containing amorphous curcumin and / or an analog thereof.
  • curcumin and its analogs have physiological activities such as tumor formation inhibitory action, antioxidant action, anti-inflammatory action, cholesterol lowering action, antiallergic action, brain disease prevention action, and heart disease prevention and treatment action.
  • Application to foods for example, functional foods
  • pharmaceuticals, cosmetics, and the like has been studied.
  • curcumin and its analogs have a problem that the physiological activity of curcumin and its analogs cannot be sufficiently obtained by oral ingestion because their absorption into the body is extremely low.
  • Patent Document 1 discloses that curcuminoids are made amorphous by melt-processing curcuminoids, thermoplastic polymers, and phosphatides, and the curcuminoids are made amorphous. A method for improving the absorption of curcuminoids into the body by ingesting the preparation is disclosed.
  • Patent Document 2 discloses a water-soluble, branched or cyclic polysaccharide (modified edible starch, pectin, plant).
  • a method for producing a curcumin complex in which rubber, propylene glycol alginate, cyclodextrin, maltodextrin derived from amylopectin and carboxymethylcellulose) are contacted in an aqueous solution having a pH of about 9 or more and acidified to have a pH of about 8 or less. Has been.
  • the melt processing described in Patent Document 1 has a problem in that it is necessary to obtain a solid dispersion through a nozzle after heating and a special technique and apparatus are required and the manufacturing cost is high.
  • the curcumin complex obtained in Patent Document 2 is used as a colorant for foods, and is used for the purpose of improving the absorption of curcumin and / or its analogs by ingestion into the body. It is not a thing. Further, it is not shown that the complex is amorphous.
  • an object of the present invention is to provide an amorphous curcumin having a high content of curcumin and / or an analog thereof, and improving the absorption of curcumin and / or an analog thereof into the body by oral ingestion at low cost. And / or providing a method for producing a complex containing the analog at a high concentration.
  • curcumin and / or its analogs that improve absorption into the body by oral ingestion.
  • curcumin and / or its analogs and hydroxypropylmethylcellulose and / or hydroxypropylcellulose After dissolving both of these in an aqueous solution having a pH of 12 or more, the pH of the solution is adjusted to 7 or less.
  • Amorphous curcumin and / or its analogs and hydroxy having significantly improved absorption in the body by oral ingestion. It discovered that the composite_body
  • the present invention provides the following [1] to [5].
  • [1] It comprises a step of dissolving curcumin and / or an analog thereof and hydroxypropylmethylcellulose and / or hydroxypropylcellulose in an aqueous solution having a pH of 12 or more, and a step of adjusting the pH of the solution to 7 or less.
  • the amorphous curcumin according to [1] or [2] and / or the analog curcumin is at least one selected from the group consisting of bisdemethoxycurcumin, demethoxycurcumin and tetrahydrocurcumin A method for producing a complex of curcumin containing an analog and / or its analog and hydroxypropylmethylcellulose and / or hydroxypropylcellulose.
  • the content ratio (A / B) of the curcumin and / or its analog (A) to the hydroxypropylmethylcellulose and / or hydroxypropylcellulose (B) is 0.1 to 10.
  • the content of curcumin and / or its analog is high, and curcumin and / or its analog and hydroxypropylmethylcellulose containing amorphous curcumin and / or its analog and / or A complex with hydroxypropylcellulose can be produced at a high concentration in a simple and inexpensive manner without the need for special techniques or equipment.
  • a complex of curcumin and / or an analog thereof containing amorphous curcumin and / or an analog thereof prepared by the production method of the present invention is hydroxypropylmethylcellulose and / or hydroxypropylcellulose.
  • complex of curcumin and hydroxypropyl methylcellulose is shown.
  • complex of curcumin and hydroxypropyl cellulose is shown.
  • complex of curcumin and methylcellulose is shown.
  • a method for producing a complex of curcumin and / or its analog containing hydroxycurcumin and / or its analog and hydroxypropylmethylcellulose and / or hydroxypropylcellulose containing the amorphous curcumin of the present invention and / or its analog (1) a step of dissolving curcumin and / or an analog thereof and hydroxypropylmethylcellulose and / or hydroxypropylcellulose in an aqueous solution having a pH of 12 or more; (2) The step of adjusting the pH of the solution to 7 or less.
  • Curcumin is a main component of curcuminoid contained in the turmeric pigment, and is a compound represented by the following structural formula (1).
  • Curcumin used in the present invention may be chemically synthesized curcumin, or may be one that is distributed as a turmeric pigment.
  • a turmeric pigment obtained by powdering dried rhizomes of ginger family turmeric (for example, Curcuma longa LINNE), the turmeric powder with an appropriate solvent (for example, ethanol, fat, propylene glycol, hexane, acetone, etc.) ), And crude curcumin or oleoresin (turmeric oleoresin) obtained by extraction with the use of) and purified curcumin.
  • Curcumin includes both tautomeric keto type and enol type.
  • curcumin analogs include demethoxycurcumin, bisdemethoxycurcumin, tetrahydrocurcumin, dihydroxytetrahydrocurcumin and the like.
  • the turmeric pigments include curcumin, demethoxycurcumin, bisdemethoxycurcumin and tetrahydrocurcumin.
  • Hydroxypropyl methylcellulose is a water-soluble cellulose derivative in which part of the hydroxy group of cellulose is substituted with a methoxy group and a hydroxypropyloxy group.
  • Various substitution degrees of the methoxy group and the hydroxypropyloxy group are known, and any of those usable as food can be used.
  • Hydroxypropyl cellulose is a water-soluble cellulose derivative in which part of the hydroxy group of cellulose is substituted with a hydroxypropyloxy group.
  • Various substitution degrees of hydroxypropyloxy groups are known, and any of those usable as food can be used.
  • the mass ratio (A / B) of curcumin and / or its analog (A) and hydroxypropylmethylcellulose and / or hydroxypropylcellulose (B) is 0 from the point of obtaining a complex having excellent oral absorbability. 0.02 to 10, preferably 0.03 to 10, more preferably 0.05 to 10, and still more preferably 0.1 to 10. Moreover, the containing mass ratio (A / B) in the obtained composite_body
  • aqueous solutions having a pH of 12 or higher include alkaline aqueous solutions such as sodium hydroxide and potassium hydroxide. Of these, an aqueous sodium hydroxide solution is particularly preferred.
  • the pH may be 12 or more, but is preferably pH 12 to 15, more preferably pH 12 to 14.
  • the amount of curcumin and / or its analog added to an aqueous solution having a pH of 12 or higher is preferably such that it reaches a saturated concentration, preferably 0.1 g / 100 mL or more, and more preferably 0.1 to 10 g / 100 mL.
  • curcumin and / or its analog (A) and (B) hydroxypropylmethylcellulose and / or hydroxypropylcellulose may be dissolved in an aqueous solution having a pH of 12 or more.
  • the pH may be adjusted to 12 or more, and (A) and (B) may be added and dissolved in an aqueous solution having a pH of 12 or more.
  • (A) may be added after adjusting the pH to 12 or higher, and (B) may be added after adjusting the aqueous dispersion of (A) to pH 12 or higher.
  • the pH of the solution is adjusted to 7 or less.
  • acids such as hydrochloric acid, a sulfuric acid, nitric acid, an organic acid, for example.
  • the preferred pH is 3-7, more preferably 5-7.
  • sodium hydroxide is used as the alkali having a pH of 12 or more and hydrochloric acid is used as the acid having a pH of 7 or less, the salt produced as a by-product is sodium chloride, so that the resulting complex is highly safe.
  • curcumin and / or its complex containing a complex of amorphous curcumin and / or its analog and hydroxypropylmethylcellulose and / or hydroxypropylcellulose A complex of the analog and hydroxypropyl methylcellulose and / or hydroxypropylcellulose can be collected.
  • drying step examples include evaporation drying, reduced pressure drying, spray drying, freeze drying, hot air drying, cold air drying, air drying, and the like, preferably vacuum drying, spray drying, and air drying.
  • the complex obtained by the method of the present invention has curcumin and / or its analog in an amorphous form, and curcumin and / or its analog has good oral absorbability. It is remarkably superior to the oral absorbability of a mixture of / or an analog thereof and hydroxypropylmethylcellulose and / or hydroxypropylcellulose. Therefore, the composition for oral consumption containing the complex is used as a pharmaceutical product, cosmetic product, dietary supplement, functional food product, food for specified health use for exhibiting the physiological activity of curcumin and / or its analogs by oral administration. Useful.
  • Reference Example 1 Solubility of curcumin in high pH aqueous solution
  • Turmeric extract powder with a curcumin content of 91.2% (w / w) provided by San-Ei Gen FFI was added to 100 mL of an aqueous sodium hydroxide solution adjusted to pH 11, 12, 13 or 14. Gradually added and the curcumin concentration in the aqueous solution at the time when the turmeric extract powder could not be completely dissolved was examined using high performance liquid chromatography (HPLC).
  • the curcumin concentration in each aqueous solution is 0.0055 g / 100 mL when dissolved in an aqueous solution of pH 11, 0.111 g / 100 mL when pH 12, 1.42 g / 100 mL when pH 13, and 14 when pH is 14. It was 13.6 g / 100 mL. From this, it was found that a large amount of curcumin can be dissolved in the aqueous solution by using an aqueous solution having a pH value of 12 or more.
  • aqueous solution To this aqueous solution was added 2.0 to 8.8 g of turmeric extract powder having a curcumin content of 91.2 or 89.5% (w / w) provided by San-Ei Gen FFI.
  • a complex of curcumin containing amorphous curcumin and hydroxypropylmethylcellulose or hydroxypropylcellulose is prepared by adjusting the pH of the aqueous solution to 7 or 6 using a 10 mol / L hydrochloric acid aqueous solution. Prepared.
  • the aqueous solution is spray-dried using a spray dryer ADL311S (manufactured by Yamato Scientific Co., Ltd.) under the conditions of an inlet temperature of 160 ° C., an outlet temperature of 75 ° C., a spray pressure of 0.12 MPa, and a feed rate of 6 to 7 mL / min.
  • a composite of curcumin containing powdered amorphous curcumin and hydroxypropylmethylcellulose or hydroxypropylcellulose (Examples 1 to 4) was prepared.
  • HPMC solution was prepared by dissolving 6 or 12 g of hydroxypropylmethylcellulose (HPMC: Metroles SE-06, manufactured by Shin-Etsu Chemical Co., Ltd.) in 150 or 167 mL of pure water.
  • HPMC hydroxypropylmethylcellulose
  • a sodium hydroxide aqueous solution 50 in which 7.55 or 5.03 g of turmeric extract powder having a curcumin content of 79.5% (w / w) provided by San-Ei Gen F.F.
  • a curcumin solution was prepared by dissolving in 33 mL.
  • the HPMC solution and the curcumin solution are mixed and the pH of the mixed solution is adjusted to 6 using a 10 mol / L aqueous hydrochloric acid solution to prepare a complex of curcumin containing amorphous curcumin and hydroxypropylmethylcellulose. did.
  • 15 or 18 g of dextrin is added here, and the dextrin is dissolved by sufficiently stirring, and then the aqueous solution is spray-dried in the same manner as described above, so that curcumin containing powdered amorphous curcumin and hydroxypropylmethylcellulose
  • the composites (Examples 5 to 6) were prepared.
  • a complex of curcumin containing amorphous curcumin and hydroxypropylmethylcellulose was prepared by adjusting the pH of the aqueous solution to 6 using a 10 mol / L hydrochloric acid aqueous solution. Next, the aqueous solution is centrifuged (2,000 ⁇ g, 10 min) to recover the solid content in the aqueous solution, which is placed on a tray and kept in a dark room for about 3 days at room temperature for drying. The dried product was recovered. The dried product was put in a mortar and appropriately pulverized with a pestle to prepare a complex of curcumin containing powdered amorphous curcumin and hydroxypropylmethylcellulose (Example 7). In addition, the case where the composite_body
  • Test Example 1 Measurement of Curcumin Crystal in Complex
  • the crystallinity of curcumin in the prepared various composites was examined using a powder X-ray diffractometer (RINT-Ultima III, manufactured by Rigaku).
  • Test Example 2 (Absorptivity of various amorphous curcumin-containing composites)
  • Test animal As test animals, 6-week-old SD rats (male, body weight of about 200 g, Japan Charles River) were used.
  • the measurement of plasma curcumin and / or its analog concentration is about 0.5 hour, 1 hour and / or 2 hours after the start of administration, from the jugular vein of the test animal under anesthesia.
  • measurement was performed by the following method. a. Pretreatment 100 ⁇ L of 0.1 M acetate buffer (pH 5.0) and 10 ⁇ L of ⁇ -glucuronidase solution (about 68,000 units / mL) were added to 20 ⁇ L of the collected plasma and held at 37 ° C. for 1 hour.
  • curcumin concentration 0 prepared by adding 10 ⁇ L of 50% ethanol solution containing 20 ng / mL mepronil to 90 ⁇ L of 50% (v / v) methanol solution (curcumin standard solution) containing 5, 125 or 250 ng / mL 9 to 225 ng / mL) under the same conditions as described above.
  • Table 4 shows the curcumin concentration in plasma (ng / mL), the maximum blood concentration (Cmax (ng / mL)), and the area under the blood concentration-time curve (AUC (ng / mL ⁇ 0-2hr)). . It can be seen that the oral absorbability of the complex obtained by the present invention is remarkably improved as compared with the curcumin bulk powder and the physical mixture.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
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  • Bioinformatics & Cheminformatics (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)

Abstract

La présente invention concerne un procédé pour produire aisément un composite qui contient de la curcumine amorphe et/ou un analogue de celle-ci à une concentration élevée à un coût faible, ledit composite ayant une teneur élevée en curcumine et/ou un analogue de celle-ci et une absorption améliorée de curcumine et/ou un analogue de celui-ci dans le corps par ingestion orale. Un procédé de production d'un composite de curcumine et/ou un analogue de celle-ci et d'hydroxypropylméthylcellulose et/ou d'hydroxypropylcellulose, ledit composite contenant la curcumine amorphe et/ou un analogue de celui-ci, qui est caractérisé en ce qu'il comprend : une étape pour dissoudre la curcumine et/ou un analogue de celui-ci et de l'hydroxypropylméthylcellulose et/ou de l'hydroxypropylcellulose dans une solution aqueuse ayant un pH de 12 ou plus ; et une étape pour diminuer le pH de la solution à 7 ou moins.
PCT/JP2015/070318 2014-07-16 2015-07-15 Procédé de production de composite contenant de la curcumine amorphe et/ou un analogue de celle-ci WO2016010093A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019160146A1 (fr) 2018-02-19 2019-08-22 株式会社セラバリューズ Composition d'ingestion orale
CN110381932A (zh) * 2017-03-03 2019-10-25 三荣源有限公司 含姜黄素制剂及其吸收性或溶出性的评价方法
EP4023246A4 (fr) * 2019-08-30 2023-10-04 San-Ei Gen F.F.I., INC. Composition solide contenant une matière amorphe, peu soluble dans l'eau, et son procédé de production
GB2629676A (en) * 2023-05-04 2024-11-06 Merry Life Biomedical Company Ltd A formulation with improved bioavailability

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JPH04502004A (ja) * 1988-11-25 1992-04-09 ヘニング・ベルリン・ゲーエムベーハー・ヘミー・ウント・ファルマベルケ オキシプリノールおよび／またはそのアルカリおよびアルカリ土類塩の調合物
JP2011512346A (ja) * 2008-02-15 2011-04-21 ノボビオン オイ クルクミンの可溶性錯体
JP2014503470A (ja) * 2010-10-14 2014-02-13 アボット ゲーエムベーハー ウント カンパニー カーゲー クルクミノイド固体分散製剤

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US4999205A (en) * 1989-08-17 1991-03-12 Kalamazoo Holdings, Inc. Curcumin complexed on water-dispersible substrates
US9259401B2 (en) * 2011-05-16 2016-02-16 Omniactive Health Technologies Ltd. Water soluble composition comprising curcumin having enhanced bioavailability and process thereof

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JPH04502004A (ja) * 1988-11-25 1992-04-09 ヘニング・ベルリン・ゲーエムベーハー・ヘミー・ウント・ファルマベルケ オキシプリノールおよび／またはそのアルカリおよびアルカリ土類塩の調合物
JP2011512346A (ja) * 2008-02-15 2011-04-21 ノボビオン オイ クルクミンの可溶性錯体
JP2014503470A (ja) * 2010-10-14 2014-02-13 アボット ゲーエムベーハー ウント カンパニー カーゲー クルクミノイド固体分散製剤

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INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 453, 2013, pages 253 - 284 *

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110381932A (zh) * 2017-03-03 2019-10-25 三荣源有限公司 含姜黄素制剂及其吸收性或溶出性的评价方法
WO2019160146A1 (fr) 2018-02-19 2019-08-22 株式会社セラバリューズ Composition d'ingestion orale
CN111726992A (zh) * 2018-02-19 2020-09-29 热值株式会社 口服摄取用组合物
KR20200122297A (ko) 2018-02-19 2020-10-27 테라벨류스 코포레이션 경구 섭취용 조성물
JPWO2019160146A1 (ja) * 2018-02-19 2021-02-25 株式会社セラバリューズ 経口摂取用組成物
EP3756471A4 (fr) * 2018-02-19 2021-11-10 Theravalues Corporation Composition d'ingestion orale
JP7072905B2 (ja) 2018-02-19 2022-05-23 株式会社セラバリューズ 経口摂取用組成物
US11672770B2 (en) 2018-02-19 2023-06-13 Theravalues Corporation Oral ingestion composition
AU2019222350B2 (en) * 2018-02-19 2023-11-16 Theravalues Corporation Oral ingestion composition
CN111726992B (zh) * 2018-02-19 2024-02-23 热值株式会社 口服摄取用组合物
EP4023246A4 (fr) * 2019-08-30 2023-10-04 San-Ei Gen F.F.I., INC. Composition solide contenant une matière amorphe, peu soluble dans l'eau, et son procédé de production
GB2629676A (en) * 2023-05-04 2024-11-06 Merry Life Biomedical Company Ltd A formulation with improved bioavailability

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