WO2017086536A1 - Composition anti-obésité contenant du phéophorbide a séparé d'un extrait de gelidium amansii comme principe actif, et son procédé de préparation - Google Patents

Composition anti-obésité contenant du phéophorbide a séparé d'un extrait de gelidium amansii comme principe actif, et son procédé de préparation Download PDF

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Publication number
WO2017086536A1
WO2017086536A1 PCT/KR2015/014316 KR2015014316W WO2017086536A1 WO 2017086536 A1 WO2017086536 A1 WO 2017086536A1 KR 2015014316 W KR2015014316 W KR 2015014316W WO 2017086536 A1 WO2017086536 A1 WO 2017086536A1
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Prior art keywords
pheophorbide
obesity
extract
solvent
obesity composition
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PCT/KR2015/014316
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English (en)
Korean (ko)
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김학주
임영훈
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주식회사 서진바이오텍
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Publication of WO2017086536A1 publication Critical patent/WO2017086536A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9706—Algae
    • A61K8/9717—Rhodophycota or Rhodophyta [red algae], e.g. Porphyra
    • 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
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/60—Edible seaweed
    • 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
    • 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
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
    • 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
    • A61K36/02—Algae
    • A61K36/04—Rhodophycota or rhodophyta (red algae), e.g. Porphyra
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin

Definitions

  • the present invention relates to a composition for anti-obesity containing the pheophorbide A (Pheophorbide A) isolated from the extract of the wormwood as an active ingredient and a method for producing the same.
  • the present invention provides a composition for anti-obesity containing Pheophorbide A (Pheophorbide A), which is isolated from the extract of the wormwood.
  • the pheophorbide A is characterized in that it comprises 5 to 15% by weight based on the total weight of the anti-obesity composition.
  • the present invention provides a cosmetic comprising the composition for anti-obesity as described above.
  • the mixture of water and trifluoroacetic acid is characterized in that consisting of 99.9% water (v / v) and 0.1% (v / v) trifluoroacetic acid.
  • the first solvent and the second solvent is characterized in that the step gradient (100: 0, 50:50, 20:80, 0: 100).
  • the mobile phase is characterized in that acetonitrile.
  • Pheophorbide A isolated from the extract of Gelidium amansii according to the present invention is excellent in lipid accumulation inhibitory effect, can be usefully used as an active ingredient of the composition for anti-obesity, anti-obesity food, Application as a cosmetic or a medicine is possible.
  • 1 is a photograph of the ummu saga used as a raw material of the present invention.
  • Figure 2 is a manufacturing process of the extract of the radish of the present invention.
  • Figure 3 is a graph showing the cytotoxicity results of the extract of radish.
  • FIG. 8 is a photograph showing the effect of inhibiting lipid accumulation on Pheophorbide A isolated from the larvae.
  • FIG. 9 is a UV-Spectrum graph for Pheophorbide A isolated from umaga.
  • FIG. 10 is a graph showing the results of HR / Mass analysis of pheophorbide A isolated from umaga.
  • FIG. 11 is a graph showing 1 H NMR spectral data of Pheophorbide A separated from umaga.
  • FIG. 12 is a graph showing 13 C NMR spectral data of Pheophorbide A isolated from umaga.
  • FIG. 15 is a graph showing HSQC-DEPT spectral data of Pheophorbide A isolated from umaga.
  • the anti-obesity active ingredient is a pheophorbide A (Pheophorbide A) I could confirm it.
  • the pheophorbide A is a compound which is separated and obtained by a high performance liquid chromatography (HPLC) using a mixed solution of water and trifluoroacetic acid as a first solvent and acetonitrile as a second solvent as a mobile phase It is characterized by.
  • Pheophorbide A isolated from the wormwood ( Gelidium amansii ) as described above has an anti-obesity effect due to its excellent lipid storage inhibitory effect.
  • the pheophorbide A may include 5 to 15% by weight based on the total weight of the anti-obesity composition. If the pheophorbide A compound is less than 5% by weight based on the total weight of the anti-obesity composition, since the anti-obesity effect cannot be sufficiently obtained, the function as the anti-obesity composition is lowered and exceeds 15%. It is uneconomical because a sufficient anti-obesity effect can be achieved without adding more content.
  • the present invention may provide food, cosmetics, and medicines including the anti-obesity composition.
  • the present invention comprises the steps of extracting the radish with a solvent to prepare a radish extract; And separating the pheophorbide A by high performance liquid chromatography (HPLC) using the mixed solution of water and trifluoroacetic acid as the first solvent and acetonitrile as the second solvent as the mobile phase. It relates to a method for producing an anti-obesity composition, characterized in that.
  • the native radish larvae native to Jeju Island are chilled for 30 to 5 hours using a solvent.
  • the solvent for the cold immersion treatment may be ethyl acetate, distilled water, methanol, etc. Among them, distilled water is preferable in terms of economics and safety.
  • the drying method is not particularly limited, but drying in a shaded place using a fan is preferable in terms of economy and convenience.
  • the pheophorbide A is a high performance liquid chromatograph using the obtained extract of ummu fern as a mobile phase using a mixture of water and trifluoroacetic acid as a first solvent and acetonitrile as a second solvent. It can be separated by chromatography (HPLC).
  • the mixed solution of water and trifluoroacetic acid is preferably 99.9% (v / v) of water and 0.1% (v / v) of trifluoroacetic acid in terms of being able to separate pheophorbide A in high yield. Do.
  • the mobile phase may be separated using acetonitrile, more preferably, the first solvent and the second solvent are separated by a step gradient (100: 0, 50:50, 20:80, 0: 100). It is preferable in that it can be separated into high purity.
  • the present invention is to provide a composition for implementing the anti-obesity effect based on the ummu fern, which is a marine biomaterial replacing the synthetic medicine, the natural origin in a situation where the safety of raw materials is emerging
  • the use of natural materials can be useful as anti-obesity foods, cosmetics and medicines because it can ensure economic and safety and exhibit an excellent anti-obesity effect.
  • the extracted extract was separated for 20 minutes at 10,000 rpm using a continuous centrifuge, injected into the concentrator through a filtration process using a 20 ⁇ m paper filter paper, and concentrated to 1/20 of the total volume at 60 ° C., and frozen. It was dried, and repeated three times to prepare the final radish extract (Fig. 2).
  • the contents of salinity, protein, total sugar, reducing sugar, total phenol and total flavonoid content, etc. were analyzed.
  • the extract was used for analysis after the preparation to the concentration of 10 mg / ml in distilled water.
  • the salt content of the daikon radish extract was measured using an ES Meter machine, and the salt content of the daikon radish extract was calculated in terms of NaCl.
  • Protein content analysis was performed using the Bradford method. 0.5 ml of protein assay dye was added to 0.1 ml of radish fern extract, and the absorbance was measured at 595 nm. The protein concentration was calculated based on BSA.
  • Total sugar analysis was performed using Phenol-sulfuric acid method. 0.2 ml of 5% phenol was added to 0.2 ml of the sample solution, followed by stirring. 1 ml of sulfuric acid solution was slowly added dropwise to the reaction mixture, mixed and reacted at room temperature for 20 minutes, and the absorbance was measured at 490 nm. The calibration curve was calculated using) -glucose and the total equivalent weight was calculated.
  • Flavonoid analysis was performed using Flavonoid-AlCl 3+ method.
  • the yellow color produced by the reaction between flavonoids and AlCl 3+ was added to 0.5 ml of extract, 0.5 ml of 2% AlCl 3+ , reacted at room temperature for 1 hour, and the absorbance was measured at 500 nm. acid was used.
  • Total polyphenol analysis was performed using the Dewanto method. 0.2 ml of distilled water and 0.2 ml of Folin-ciocalteu's phenol reagent were added to 0.1 ml of the sample, followed by reaction at room temperature for 3 minutes, and 2 ml of 20% NaCO 3 for 1 hour at room temperature, and then absorbance at 765 nm. Gallic acid was used.
  • Table 1 shows 13.1 ⁇ 0.2% of total sugar, 11.7 ⁇ 0.2% of reducing sugar, 6.6 ⁇ 0.1% of total protein, 2.6 ⁇ 0.8% of polyphenol, and 15.5 ⁇ 1.6% of flavonoids.
  • Flavonoids are a pigment compound mainly distributed in plants and present in glycosides in combination with various sugars, and are known to have antimicrobial, anticancer, antiviral and anti-inflammatory effects, and show little toxicity. In particular, it is known to lower the content of LDL cholesterol in the blood to prevent various blood lipid-related diseases and to suppress obesity by weight loss.
  • the extracts of daikon radish contain a large amount of flavonoids and polyphenols in addition to sugars and proteins. It was judged that.
  • MTT assay was performed using 3T3L-1, 3T3-F442A and C3HT101 / 2clone8 cells.
  • the cells were placed in a 6-well plate, incubated at 37 ° C. for 24 hours, and then samples were added to each well by concentration, followed by incubation at 37 ° C. for 2 days, and then culture was removed from each well, 100 ⁇ l of MTT solution (a solution of tetrazolium dye MTT (3- (4,5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide)) was added thereto, followed by incubation for 2 hours, followed by MTT The solution was removed. 100 ⁇ l of dimethyl sulfoxide was added to each well, followed by reaction for 15 to 20 minutes, and the absorbance was measured at an optical density of 540 nm.
  • MTT solution a solution of tetrazolium dye MTT (3- (4,5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide
  • Oil-Red O staining using 3T3L-1, 3T3-F442A, and C3HT101 / 2clone8 cells was performed to confirm the intracellular lipid accumulation inhibitory ability of the extract of Bovine fern from 1-1.
  • the number of cells was measured and added to a 6-well plate to be 0.8 ⁇ 10 5 / well, followed by 2 days of culture to allow 100% of the cells to be cultured, and 2 days of further culture was inhibited to inhibit cell differentiation. , The culture was removed.
  • 2 ml of differentiation culture medium containing MDI (1M dexamethasone), 0.5 mM isobutylmethylxanthine (IBMX: isobutylmethylxanthine) and 10 ⁇ g / ml insulin (insulin) were added, followed by incubation for 3 days. . From this time, samples were treated by concentration (50 ⁇ g / ml, 100 ⁇ g / ml).
  • the culture solution was removed, and 2 ml of the differentiated culture solution to which insulin was added and the sample were added and cultured for 2 days. Thereafter, 1 ml of the culture solution was removed at 2 days intervals, and 1 ml of the fresh culture solution and the sample were added thereto, and then cultured for about 10 days.
  • the cell culture was removed and washed by adding 1 ml of PBS. After 200% of 10% formaldehyde was treated and fixed at room temperature for 1 hour, formaldehyde was removed, and 60% Isopropanol was washed with 200 ⁇ l and dried completely. 1 ml each of Oil red O working solution was added and incubated at room temperature for 30 minutes. Then, after removing the supernatant, and washed twice with PBS, Isopropanol 1ml was added to confirm the effect of inhibiting lipid accumulation after re-dissolution.
  • HPLC analysis conditions are as follows.
  • the 56-minute peak aliquot was the highest absorption wavelength at 411nm confirmed that the 56-minute peak aliquot has the potential as an anti-obesity substance, such as HR / Mass, As a result of 1 H-NMR and 13 C NMR analysis, it was confirmed that the molecular formula was C 35 H 36 N 4 O 5 , which was a substance having a molecular weight of 592.27.
  • Pheophorbide A isolated from the extract of Gelidium amansii according to the present invention exhibits anti-obesity effect due to its excellent lipid accumulation inhibitory effect, and thus can be applied as an anti-obesity food, cosmetic or pharmaceutical product. .

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Abstract

La présente invention concerne une composition anti-obésité contenant, comme principe actif, du Phéophorbide A séparé d'un extrait de Gelidium amansii. Le Phéophorbide A séparé d'un extrait de Gelidium amansii, selon la présente invention, a un excellent effet de suppression de stockage de lipide, en présentant ainsi un effet anti-obésité, et peut ainsi être utilisé dans des aliments anti-obésité, des produits cosmétiques ou des produits pharmaceutiques.
PCT/KR2015/014316 2015-11-19 2015-12-28 Composition anti-obésité contenant du phéophorbide a séparé d'un extrait de gelidium amansii comme principe actif, et son procédé de préparation WO2017086536A1 (fr)

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KR20150162788 2015-11-19
KR10-2015-0162788 2015-11-19

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021118298A1 (fr) * 2019-12-11 2021-06-17 주식회사 파이안바이오테크놀로지 Composition pharmaceutique destinée à prévenir ou traiter la fibrose, comprenant un composé phéophorbide en tant que principe actif

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US20030023081A1 (en) * 2001-06-01 2003-01-30 Ceramoptec Industries Inc. Water-soluble porphyrin derivatives for photodynamic therapy, their use and manufacture
KR20140029842A (ko) * 2012-08-30 2014-03-11 차의과학대학교 산학협력단 우뭇가사리 추출물을 포함하는 기능성 식품
KR20140045647A (ko) * 2012-10-09 2014-04-17 한국생명공학연구원 페어포바이드계 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 대사성 질환 또는 이들의 합병증의 예방 또는 치료용 조성물
KR20140047247A (ko) * 2012-10-11 2014-04-22 고려대학교 산학협력단 페오포바이드 ａ와 같은 포피린계 물질을 유효성분으로 함유하는 항산화 제재와, 당뇨병 및 당뇨합병증 예방 또는 치료용 조성물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030023081A1 (en) * 2001-06-01 2003-01-30 Ceramoptec Industries Inc. Water-soluble porphyrin derivatives for photodynamic therapy, their use and manufacture
KR20140029842A (ko) * 2012-08-30 2014-03-11 차의과학대학교 산학협력단 우뭇가사리 추출물을 포함하는 기능성 식품
KR20140045647A (ko) * 2012-10-09 2014-04-17 한국생명공학연구원 페어포바이드계 화합물 또는 이의 약학적으로 허용가능한 염을 유효성분으로 함유하는 대사성 질환 또는 이들의 합병증의 예방 또는 치료용 조성물
KR20140047247A (ko) * 2012-10-11 2014-04-22 고려대학교 산학협력단 페오포바이드 ａ와 같은 포피린계 물질을 유효성분으로 함유하는 항산화 제재와, 당뇨병 및 당뇨합병증 예방 또는 치료용 조성물

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PARK, HYOUNG-SEO: "A Study on Function of Natural Dyeing of Seaweed", JOURNAL OF THE KOREAN ASSOCIATION OF PRACTICAL ARTS EDUCATION CONFERENCE, 2010, pages 122 - 144 *
SEO, M. -J. ET AL.: "Extract from Edible Red Seaweed (Gelidium amansii) Inhibits Lipid Accumulation and ROS Production during Differentiation in 3T3-L1 Cells", PREVENTIVE NUTRITION AND FOOD SCIENCE, vol. 17, no. 2, June 2012 (2012-06-01), pages 129 - 135, XP053028613 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021118298A1 (fr) * 2019-12-11 2021-06-17 주식회사 파이안바이오테크놀로지 Composition pharmaceutique destinée à prévenir ou traiter la fibrose, comprenant un composé phéophorbide en tant que principe actif

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