WO2019164458A1 - Composition applicable pour améliorer la cicatrisation des plaies comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine - Google Patents

Composition applicable pour améliorer la cicatrisation des plaies comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine Download PDF

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Publication number
WO2019164458A1
WO2019164458A1 PCT/TH2018/000006 TH2018000006W WO2019164458A1 WO 2019164458 A1 WO2019164458 A1 WO 2019164458A1 TH 2018000006 W TH2018000006 W TH 2018000006W WO 2019164458 A1 WO2019164458 A1 WO 2019164458A1
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WO
WIPO (PCT)
Prior art keywords
extract
rice
sesamin
composition
particle
Prior art date
Application number
PCT/TH2018/000006
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English (en)
Inventor
Prachya Kongtawelert
Peraphan Pothacharoen
Original Assignee
Thailand Excellence Center For Tissue Engineering And Stem Cells
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Publication date
Application filed by Thailand Excellence Center For Tissue Engineering And Stem Cells filed Critical Thailand Excellence Center For Tissue Engineering And Stem Cells
Priority to PCT/TH2018/000006 priority Critical patent/WO2019164458A1/fr
Publication of WO2019164458A1 publication Critical patent/WO2019164458A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/726—Glycosaminoglycans, i.e. mucopolysaccharides
    • 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)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • 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

Definitions

  • the present disclosure relates to a composition for wound healing.
  • a composition applicable for enhancing wound healing comprising a mixture having polysaccharide peptides of rice particle, a first extract of rice bran and a second extract of sesamin.
  • Wound healing is a complex but well- orchestrated tissue repair process including: hemostatic/inflammatory response, cell proliferation/ formation of connective tissues, wound contraction and remodeling.
  • Stem cells are characterized by their multipotency and capacity for self-renewal and differentiation to various cell types.
  • Stem cells can be categorized as embryonic stem cells (ESCs), tissue specific progenitor stem cells (TSPSCs), mesenchymal stem cells (MSCs), umbilical cord stem cells (UCSCs), bone marrow stem cells (BMSCs), and induced pluripotent stem cells (iPSCs) (Mahla RS. Stem cells applications in regenerative medicine and disease therapeutics. Int J Cell Biol. 20l6;20l6:6940283). Stem cells have potential uses in many different areas of research, biotechnology and medicine such as study human development, testing of new drugs, screening toxins, testing gene therapy methods, and replace damaged tissues.
  • stem cells have therapeutic potential for wound healing.
  • Preclinical of stem cells in various animal models and clinical trials have been studied in wound healing, such as for tissue regeneration.
  • translation of the laboratory experiment results into clinical applications has been limited by the dependence of stem cell propagation.
  • stem cell for clinical application is based on their subsequent large-scale in vitro expansion by conventional static adherent cultures in the presence of fetal bovine serum (FBS) (Jung S et al. Large- scale production of human mesenchymal stem cells for clinical applications. Biotechnol Appl Biochem. 2012;59(2): 106-20).
  • FBS fetal bovine serum
  • a first embodiment of the invention is a composition applicable for enhancing wound healing comprising a mixture having polysaccharide peptides of rice particle, a first extract of rice bran and a second extract of sesamin.
  • the polysaccharide peptides, the first extract and the second extract are in a ratio of 1 : 1 : 1 by weight.
  • the polysaccharide peptides is acquired by heating the rice particle at a temperature of 120 °C for 20 minutes under a pressure of 15 psi in the presence of an aqueous phase.
  • the rice particles can be pulverized rice powder with a particle size of 160 to 315 microns.
  • the first extract of rice bran is acquired by mechanical polishing of rice grains.
  • the second extract of sesamin can be an ethanolic extract.
  • the second extract of sesamin is an ethanolic extract and wherein the composition further comprises glucosamine sulfate.
  • the second extract of sesamin is acquired by bringing sesame oil into contact with absolute ethanol solvent, removing the sesamin from the solvent and vaporizing the solvent to yield the second extract.
  • FIG. 1 is a graph charting the mediated proliferation rate of mesenchymal stem cells (MSC) for an embodiment of the invention.
  • FIG. 2 is a flowchart of the steps involved in an embodiment of the invention for preparation of polysaccharide peptides of rice particle.
  • FIG. 3 is a flowchart of the steps involved in an embodiment of the invention for preparation of ethanolic extract of rice bran.
  • FIG. 4 is a chromatogram of standard of anthocyanins: cyanidin 3-O-glucoside chloride, C3G; peonidin 3-O-glucoside chloride, P3G; cyanidin 3-O-rutinoside chloride, C3R; and cyanidin chloride.
  • FIG. 5 is a chromatogram of anthocyanin content in purple rice extracts (PREs) from ethanolic extracts.
  • FIG. 6 is a flowchart of the steps involved in an embodiment of the invention for preparation of ethanolic extract of sesamin.
  • FIG. 7 is a mass spectrogram and chemical structure of the ethanolic extract of sesamin purified from S. indicum.
  • the mediated proliferation rate of mesenchymal cell for an embodiment of the invention is illustrated in the graph 1-00 of FIG. 1, comparing percentage of proliferation following stimulating mesenchymal stem cell with the composition applicable for enhancing wound healing, polysaccharide peptides, rice bran, and sesamin, respectively.
  • the composition applicable for enhancing wound healing mediates the highest proliferation rate of mesenchymal stem cells at day 5.
  • FIG. 2 is a flowchart 2-00 of the steps involved in an embodiment of the invention for preparation of polysaccharide peptides of rice particle, which include:
  • FIG. 3 is a flowchart 3-00 of the steps involved in an embodiment of the invention for preparation of ethanolic extract of rice bran, which include:
  • the standard chromatogram of anthocyanins is charted in the graph 4-00 of FIG. 4, which are cyanidin 3-O-glucoside chloride 1, C3G; peonidin 3-O-glucoside chloride 2, P3G; cyanidin 3-O-rutinoside chloride 3, C3R; and cyanidin chloride 4.
  • FIG. 6 is a flowchart 6-00 of the steps involved in an embodiment of the invention for preparation of ethanolic extract of sesamin, which include:
  • Rice bran is the outer layer of the rice grain and obtained as a byproduct of rice milling process.
  • Sesame is an oilseed crops widely grown in Africa and Asia. It contains phytochemical compounds including sesamin, sesamol, sesamolactol and anthrasesamone F.
  • a first embodiment of the invention is a composition applicable for enhancing wound healing comprising a mixture having polysaccharide peptides of rice particle, a first extract of rice bran and a second extract of sesamin.
  • the polysaccharide peptides, the first extract and the second extract are in a ratio of 1:1:1 by weight.
  • the polysaccharide peptides is acquired by heating the rice particle at a temperature of 120 °C for 20 minutes under a pressure of 15 psi in the presence of an aqueous phase.
  • the rice particles can be pulverized rice powder with a particle size of 160 to 315 microns.
  • the first extract of rice bran is acquired by mechanical polishing of rice grains.
  • the second extract of sesamin can be an ethanolic extract.
  • the second extract of sesamin is an ethanolic extract and wherein the composition further comprises glucosamine sulfate.
  • the second extract of sesamin is acquired by bringing sesame oil into contact with absolute ethanol solvent, removing the sesamin from the solvent and vaporizing the solvent to yield the second extract.
  • PBMNCs were obtained from 35-40 mL of peripheral venous blood by a previously described density gradient centrifugation method. The venous blood was centrifuged at 1500 rpm for 5 min to separate plasma from other blood components. Afterward, plasma was removed for the measurement of sRAGE, and the remaining blood component was diluted with an equal volume of Dulbecco’s modified Eagle’s medium (DMEM) sold under the trademark GIBCO. The diluted mixture was then carefully overlaid on the density gradient cell separation medium sold under the trademark HISTOPAQUE (specific gravity 1.077 g/mL; SIGMA- ALDRICH) and centrifuged at 4000 rpm for 30 min.
  • DMEM Dulbecco’s modified Eagle’s medium
  • the PBMNCs were isolated from the mononuclear cell layer, and were then washed twice with warmed RPMI sold under the trademark GIBCO.
  • the isolated PBMNCs were plated in five wells of 24- well culture plates (3.7 c 10 6 ⁇ 7 c 10 5 cells per well) and cultured in RPMI supplemented with 10% (v/v) fetal bovine serum sold under the trademark GIBCO. After they had been cultured for 3 days, the floating cells were discarded and the adherent cells were further cultured in DMEM supplemented with 10% (v/v) fetal bovine serum sold under the trademark GIBCO. The culture medium was changed every 3 days not only to feed the cells but also to discard the floating cells. The plastic-adhered PBMNCs were cultured for 7-10 days until confluence and used for further analysis.
  • Characterization and cell growth rate of the human mesenchymal stem cells by cell proliferation assay was accomplished as follows.
  • Cell proliferation was assessed by Alamar blue assay (Alamar blue sold under the trademark SIGMA-ALDRICH) and carried out as follows. The cells were individually plated in 96 well-culture plate (IxlO 3 cells/well) and incubated in 5% C0 2 incubator at 37°C. After incubation for 24 hr., 100 m ⁇ of 10% (v/v) Alamar Blue (rasazurin) in 10% (v/v) FCS DMEM was replaced. After 4 hr.
  • the cells were exposed to the composition applicable for enhancing wound healing (12.5 mg/ml) or polysaccharide peptides (0.5 mg/ml) or rice bran (12.5 mg/ml) or sesamin for additional 3, 5, 7, 9 and 11 days. Each treatment was carried out in triplicate. After the end of treatment, cell proliferation assay was performed as described above.
  • Sample powder of rice bran was dissolved in in 50 mM Phosphate buffer pH 6.98 with 150 mM NaCl at final concentration 5 mg/ml. The mixture was incubated and mixed by using vigorously shaking machine for 45 minutes at room temperature. The mixture was centrifuged at 3000xg for 5 minutes and filtered with 0.22 pm filter. The aqueous phase of extract was fractionated with gel filtration by the gel sold under the trademark SUPERDEX 200 increase 10/300 GL at flow rate 0.75 ml/min for 1.8 CV. The fractions were evaporated and freeze-dried to yield the rice particle.
  • Rice particles were pulverized to a particle size of 160 to 315 microns.
  • the pulverized rice particles were heated at a temperature of 120 °C for 30 minutes under a pressure of 15 psi in the presence of an aqueous phase.
  • the heated rice particle was centrifuged and filtered with 0.22 pm filter to yield polysaccharide peptides.
  • Preparation of ethanolic extract of rice bran was accomplished as follows. Rice bran were acquired by mechanical polishing of rice grains and then extracted with ethanol. The ethanolic extract of rice bran was collected, evaporated in vacuo at 45-50 °C and freeze-dried to yield the first extract of rice bran.
  • HPLC High performance liquid chromatography analysis demonstrating enhanced wound healing was accomplished as follows. Anthocyanin content in ethanolic extract of purple rice and white rice were analyzed by using the HPLC sold under the trademark ALIGENT 1260 SERIES (Agilent Technologies Ltd.), equipped with a binary pumping system. Modified from Chromadex method, samples (10 m ⁇ ) were injected into the Cl 8 column sold under the trademark ZORBAX ECLIPSE PLUS (4.6 x 100 mm, particle size 3.5 m). The mobile phase consisted of water/formic acid (90:10, V/v) (A) and acetonitrile (B).
  • the gradient program was accomplished at 35 °C: initial time, 4% solution B; 8 min, 15% solution B; 24 min, 80% solution B; 30 min, 4% solution B at a flow rate 1.0 ml/min.
  • Major individual compounds of extracts were analyzed at a wavelength of 530 nm.
  • Four selected pure anthocyanin compound includes cyaniding-3-O-glucoside (C3G), cyaniding-3-O-rutinoside (C3R), peonidin-3- O-glucoside (P3Gj and cyariidin chloride (CC) were sold under the trademark SIGMA.
  • the peak area from the extracts were calculated using calibration curve which constructed by injecting the reference standards concentration range 0-50 pg/ml, these results are represented in FIG. 4.
  • anthocyanin content in purple rice extracts was accomplished as follows. To determine the amount of anthocyanin content in ethanolic extracts of purple rice by HPLC, 100 pg/ml of C3G, P3G, C3R and cyanidin chloride were used as the standard , these results are represented in FIG. 4. In the purple rice extracts (PREs) concentrate, two anthocyanins include C3G and P3G were detected, these results are represented in FIG. 5.
  • Preparation of ethanolic extract of sesamin was accomplished as follows. Seeds of S. indicum Linn were collected from the Lampangzhou of Thailand and voucher specimens (BKF No. 138181) were deposited at the National Park, Wildlife and Plant Conservation Department, Ministry of Natural Resources and Environment, Bangkok, Thailand. Air-dried and finely powdered seed (460 g) from S. indicum was percolated 6 times with 4 liters of hexane for 3 days at room temperature. The liquid extract was evaporated under reduced pressure to prepare a crude hexane extract. The latter was used for purification of sesamin. The. crude extract was fractionated by the silica gel column chromatography (CC) sold under the trademark MERCK (MERCK No.
  • the specific subfraction was further purified by crystallization with EtOH to yield colorless needle crystals, this being identified as sesamin using nuclear magnetic resonance spectroscopy and mass spectrometry (430 mg, 0.11% yield) and confirmed with comparison to the an authentic standard sold under the trademark SIGMA-ALDRICH by co-chromatography using high performance liquid chromatography (the column sold under the trademark HYPERSIL ODS-25, 250 c 4.6 mm by ThermoHypersil Co.) and eluted with linear gradient system comprising CH3CN and H2O (50:50 to 70:50 v/v) at the flow rate of 1.0 ml/min. Eluent was monitored at wavelength of 280 nm.
  • composition applicable for enhancing wound healing which comprises a mixture having (a) polysaccharide peptides of rice particle; (b) a first extract of rice bran and (c) a second extract of sesamin, wherein the polysaccharide peptides, the first extract and the second extract are in a ratio of 1:1 :1 by weight.

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Abstract

L'invention concerne une composition applicable pour améliorer la cicatrisation des plaies comprenant un mélange comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine. Dans un premier mode de réalisation alternatif de l'invention, les peptides polysaccharides, le premier extrait et le second extrait sont dans un rapport de 1:1:1 en poids. Dans un deuxième mode de réalisation alternatif de l'invention, les peptides de polysaccharide sont acquis par chauffage de la particule de riz à une température de 120 °C pendant 20 minutes sous une pression de 15 psi en présence d'une phase aqueuse. Les particules de riz peuvent être une poudre de riz pulvérisée ayant une taille de particule de 160 à 3,15 microns.
PCT/TH2018/000006 2018-02-23 2018-02-23 Composition applicable pour améliorer la cicatrisation des plaies comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine WO2019164458A1 (fr)

Priority Applications (1)

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PCT/TH2018/000006 WO2019164458A1 (fr) 2018-02-23 2018-02-23 Composition applicable pour améliorer la cicatrisation des plaies comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine

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PCT/TH2018/000006 WO2019164458A1 (fr) 2018-02-23 2018-02-23 Composition applicable pour améliorer la cicatrisation des plaies comprenant des peptides polysaccharides de particules de riz, un premier extrait de son de riz et un second extrait de sésamine

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070104858A1 (en) * 2000-02-07 2007-05-10 Granate Seed Limited,a New Zealand corporation Process for extraction of beta-glucan from cereals and products obtained therefrom
WO2010060362A1 (fr) * 2008-11-26 2010-06-03 Rongxiang Xu Pansement pour accélérer la guérison des blessures et procédé d'utilisation et de fabrication correspondant
US20160256480A1 (en) * 2015-03-03 2016-09-08 Wintley PHIPPS Therapeutic composition for wound healing

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070104858A1 (en) * 2000-02-07 2007-05-10 Granate Seed Limited,a New Zealand corporation Process for extraction of beta-glucan from cereals and products obtained therefrom
WO2010060362A1 (fr) * 2008-11-26 2010-06-03 Rongxiang Xu Pansement pour accélérer la guérison des blessures et procédé d'utilisation et de fabrication correspondant
US20160256480A1 (en) * 2015-03-03 2016-09-08 Wintley PHIPPS Therapeutic composition for wound healing

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PHETPORNPAISAN, P. ET AL.: "A local Thai cultivar glutinous blackrice bran: a source of functional compounds in immunomodulation, cell viability and collagen synthesis, and matrix metalloproteinase-2 and -9 inhibition", JOURNAL OF FUNCTIONAL FOODS, vol. 7, 17 January 2014 (2014-01-17) - March 2014 (2014-03-01), pages 650 - 661, XP055631811 *
SHARIF, M. R. ET AL.: "Evaluation of the wound healing activity of sesame oil extract in rats", WORLD JOURNAL OF MEDICAL SCIENCES, vol. 9, no. 2, 2013, pages 74 - 78, XP055631814 *

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