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WO2005097153A2 - Extraits de fruit de la passion et utilisations de ces extraits - Google Patents

Extraits de fruit de la passion et utilisations de ces extraits Download PDF

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Publication number
WO2005097153A2
WO2005097153A2 PCT/US2005/011244 US2005011244W WO2005097153A2 WO 2005097153 A2 WO2005097153 A2 WO 2005097153A2 US 2005011244 W US2005011244 W US 2005011244W WO 2005097153 A2 WO2005097153 A2 WO 2005097153A2
Authority
WO
WIPO (PCT)
Prior art keywords
extract
passion fruit
mammal
blood pressure
nitric oxide
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/US2005/011244
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English (en)
Other versions
WO2005097153A3 (fr
Inventor
Lai Yeap Foo
Yinrong Lu
Ronald Watson
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.)
Callaghan Innovation Research Ltd
Kemin Foods LC
Southwest Scientific Editing and Consulting LLC
Original Assignee
Industrial Research Ltd
Kemin Foods LC
Southwest Scientific Editing and Consulting LLC
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Industrial Research Ltd, Kemin Foods LC, Southwest Scientific Editing and Consulting LLC filed Critical Industrial Research Ltd
Priority to EP05733041A priority Critical patent/EP1763360A4/fr
Priority to NZ550120A priority patent/NZ550120A/en
Priority to CA002561951A priority patent/CA2561951A1/fr
Priority to JP2007506337A priority patent/JP2007531734A/ja
Publication of WO2005097153A2 publication Critical patent/WO2005097153A2/fr
Publication of WO2005097153A3 publication Critical patent/WO2005097153A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

Definitions

  • the invention relates generally to botanical extracts and, more specifically, to extracts of passion fruit (Passiflora sp.), including particularly extracts of the skin of passion fruit, and the use of the extracts for food, nutraceutical, and medical applications.
  • Hypertension or a blood pressure higher than 140/90 mm Hg, is the most common risk factor for cardiovascular and cerebrovascular morbidity and mortality. In the United States, high blood pressure is responsible for 40,000 deaths annually, while being the most modifiable risk factor for stroke. Hypertension affects about one in four adults, or almost 50 million people in the United States.
  • a Framingham study showed that as people aged from 30 to 65 years, their blood pressure increased an average 20 mm Hg systolic and 10 mm Hg diastolic pressure, with systolic blood pressure continuing to rise up to age 90. While higher blood pressure increases the likelihood of a cardiovascular event, hypertension is not often well controlled and too few patients are adequately treated.
  • Nitric oxide is a potent vasodilator. It inhibits platelet activation, limits leukocyte adhesion to the endothelium, and regulates myocardiocontractility. Synthesis of nitric oxide catalyzed by nitric oxide synthase (NOS) occurs in the vascular endothelium while the production of nitric oxide involving inducible nitric oxide synthase (iNOS) is associated with immune function. However, small amounts of nitric oxide produced by another NOS, epithelial nitric oxide synthase (eNOS), have a cytoprotective effect and vasodilation action on the cardiovascular system.
  • NOS nitric oxide synthase
  • Peroxynitrite is a potentially damaging oxidant, formed from nitric oxide (NO+0 2 ONOO " ). Peroxynitrite can give rise to lipid peroxidation, protein nitration, DNA single- strand breakage, and guanidine nitration. It has been shown that the flavonoids quercetin and kaempferol inhibit NOLA- dependent spontaneous aortic ring contraction in spontaneously hypertensive rat (SHR) cells in vitro. NOLA is a nitric oxide synthase inhibitor. Large dose acetylcholine-induced vascular contraction can also be inhibited by antioxidative flavonoids such as quercetin, kaempferol, rutin, and esculetin. Inhibition of vascular smooth muscle contraction should lead to lower blood pressure. In addition, the effects of flavonoids on immune function are controversial.
  • Catechin enhances proliferation of lymphocytes and antibody production, while it exerts an inhibitory effect at high concentration.
  • flavonoids enhance NK cell activity, while other studies show that flavonoids have no effect. Quercetin seems to inhibit non-specific immunological responses and exerts an anti-inflammatory action.
  • Passion fruit (Passiflora edulis) is a subtropical or tropical plant with a vigorous climbing character, growing to 20 ft. The purple passion fruit is native from southern Brazil through Paraguay to northern Argentina. Its fruit is nearly round or ovoid, 1.5 to 3 inches wide, with a tough, smooth and waxy rind.
  • a passion fruit extract lowers systolic blood pressure in spontaneously hypertensive rats (SHR), and decreases nitric oxide production from iNOS, thus improving endothelial dysfunction in SHR. It is therefore also envisaged that the passion fruit extract will exhibit antioxidant properties. It is therefore an object of the invention to provide an extract of passion fruit which exhibits therapeutic effects against hypertension, and diseases associated with hypertension, and which is hepatoprotective, or at least to provide a useful choice.
  • the invention provides a method of lowering blood pressure in a mammal comprising administering an effective amount of a passion fruit extract to the mammal.
  • the invention provides a method of preventing or treating a disease or disorder in a mammal where it is desirable to lower blood pressure comprising administering an effective amount of a passion fruit extract to the mammal.
  • a method of lowering serum nitric oxide levels in a mammal comprising administering an effective amount of a passion fruit extract to the mammal.
  • the invention further provides a method of treating a disease or disorder related to liver function in a mammal comprising administering an effective amount of a passion fruit extract to the mammal.
  • the invention therefore provides a method of treating hypertension as well as any other disease or disorder associated with elevated blood pressure.
  • the invention further provides-a method of hepatoprotection in a mammal, as well as a method of treating any disease or disorder related to liver function.
  • the invention further provides the use of a passion fruit extract as an antioxidant to inhibit damage from free radicals, to reduce serum lipid peroxidation and to preserve healthy tissue antioxidant vitamin levels.
  • the passion fruit extract of the invention includes one or more of the group selected from quercetin, cyanidin glycoside, catechin, epicatechin, luteolin, phenylpyruvic acid, the novel edulilic acid isolated and described herein, and any glycoside thereof.
  • the passion fruit extract is prepared by a process including the following steps: (i) preferably, cutting the passion fruit into pieces to increase the surface area; (ii) contacting the pieces of passion fruit with water to give an aqueous extract and a solid residue; (iii) separating the aqueous extract from the solid residue; (iv) contacting the aqueous extract with a polymeric matrix to adsorb one or more components of the extract onto the matrix; (v) washing the matrix with water; and/ (vi) eluting the one or more components from the matrix with an organic solvent or mixture of organic solvents.
  • the skin of the passion fruit is removed from the flesh and used in the extraction process.
  • the invention also provides a composition containing the passion fruit extract.
  • the composition may be a food or food product.
  • the composition may also be a dietary supplement, such as a nutraceutical or other nutritional composition.
  • the composition may be a pharmaceutical composition comprising the extract described above, admixed with one or more pharmaceutically acceptable excipients.
  • the invention provides the use of a passion fruit skin extract as a nutraceutical, such-as a dietary supplement, or as an active ingredient in the preparation of medical or functional foods and beverages.
  • Figs. 2 is a diagrammatical representation of data showing the reduction in blood pressure in a group of spontaneously hypertensive rats administered the extract of passion fruit.
  • Fig. 3 is a diagrammatical representation of data showing the reduction in serum nitric oxide levels in a group of rats administered the extract of passion fruit.
  • Figs. 4a and 4b are diagrammatical representations of data showing the in vivo increase in activity of Na-K ATPase and Ca ATPase, respectively, by the extract of passion fruit.
  • Figs. 2 is a diagrammatical representation of data showing the reduction in blood pressure in a group of spontaneously hypertensive rats administered the extract of passion fruit.
  • Fig. 3 is a diagrammatical representation of data showing the reduction in serum nitric oxide levels in a group of rats administered the extract of passion fruit.
  • Figs. 4a and 4b are diagrammatical representations of data showing the in vivo increase in activity of Na-K ATPase and Ca ATPa
  • FIGS. 5a and 5b are diagrammatical representation of data showing the reduction in systolic blood pressure and diastolic blood pressure, respectively, in a group of humans administered the extract of passion fruit.
  • Figs. 6a and 6b are drawings showing H-l methylene proton interactions with H- 1 ' and H-2' of the sugar moiety.
  • Figs. 7a and 7b are HPLC-ELSD chromatograms of the extracts of passion fruit skin and pulp, respectively, obtained under identical conditions
  • passion fruit means generally the fruit including both the skin and the edible pulp.
  • the term "passion fruit skin” is used to mean the remaining part of the fruit after the edible pulp inside has been removed.
  • HPLC analysis indicates that the passion fruit extract of the invention contains a number of flavonoids, including quercetin, quercetin galactoside, quercetin glucoside, luteolin, luteolin glucoside, cyanidin-3-glucosides, catechin and epicatechin. (Fig. 1).
  • the flavonoid and cyanidin components of the extract inhibit superoxide formation and nitric oxide production from iNOS, thus improving endothelial dysfunction and lowering blood pressure.
  • Quercetin has been shown to inhibit iNOS mRNA and the production of nitric oxide. Human essential hypertension is characterized by impaired endothelium- dependent vasodilation, caused by oxidative stress.
  • the extract of the invention has anti- hypertensive effects.
  • the flavonoid components of the extract lower blood pressure, inhibit oxidation of LDL, and inhibit platelet aggregation, thereby exerting a cardiovascular protecting action.
  • the components of the extract include quercetin, a compound know to have antihypertensive activity, but the amount contained in the extract is less than between about 1 and 5% and is not sufficient to substantially account for the antihypertensive activities of the extract.
  • the nitric oxide concentration was 11.07 ⁇ mol/L in rats fed with 50 mg/kg of the extract, 65% lower than that in rats fed no extract (Fig. 3). This will prevent the overproduction of nitric oxide and its subsequent reaction to form peroxynitrite which is detrimental to the cardiovascular system.
  • the applicants have also found, in rat liver studies, that the passion fruit extract is hepatoprotective. Precision-cut rat liver slices were incubated with 20 ⁇ g/ml of passion fruit extract. At 9 and 24 hours incubation, potassium levels in the slices, an index of viability, were not significantly different from control slices. The extract was then incubated with precision-cut rat liver slices in the presence or absence of ImM chloroform, a hepatotoxicant.
  • FIG. 5 shows the change in SBP (systolic blood pressure) and DBP (diastolic blood pressure) in hypertensive patients who received placebo or passion fruit extract (2 mg/lb/day, maximum 400 mg /day) for four weeks.
  • Passion fruit extract or placebo pills were given in a randomized, double-blind, parallel group fashion to these patients. They had an average systolic blood pressure of 176.60 ⁇ 4.90 mm Hg (mean ⁇ SEM).
  • Passion fruit treatment decreased systolic blood pressure significantly (p ⁇ 0.001) to 145.67 ⁇ 4.44 mm Hg (mean ⁇ SEM) as compared to the placebo group.
  • the extract may be administered to a patient by a variety of routes, including oral administration, or injection.
  • the amount of extract to be administered will vary widely depending upon the patient and the nature and extent of the disorder to be treated.
  • the extract is formulated as a composition which may be administered intravenously or by oral ingestion.
  • the composition may be ingested or intravenously administered in any dosage levels and dosage frequencies suitable for lowering blood pressure and/or increasing immune function.
  • the composition of the invention may also be a food product, including, but not limited to, a nutritional supplement.
  • the extract may be formulated into solid or liquid preparations, for example tablets, capsules, powders, solutions, suspensions and dispersions. Liquid forms include carriers such as water and ethanol, with or without other agents such as pharmaceutically acceptable surfactants or suspending agents.
  • Example 1 Preparation of Passion fruit Extract
  • Passion fruits Passi ⁇ ora edulis
  • the shells were chopped into small pieces less than 10 mm in length and placed in a container.
  • Hot water 65-75 °C was added to the container to immerse the chopped shells completely.
  • the mixture was stirred occasionally during the first hour and then left to soak overnight.
  • the mixture was filtered and the filtrate passed through a column of non-ionic polymeric resin to absorb phenolic and other organic compounds. Distilled water was passed through the column to wash out sugars and other polar components.
  • the absorbed compounds were then eluted from the column with methanol and the eluant concentrated under reduced pressure to give a dark concentrate.
  • the concentrate was freeze-dried to give the passion fruit extract as a dark red powder. While methanol was used as the eluting agent, ethanol, isopropyl alcohol, 1- propanol or acetone could also have been used.
  • Example 2 Determination of Components of Passion fruit Extract
  • the components of the extract were determined by HPLC. Experiments were carried out on a Hewlett Packard 1100 instrument equipped with a DAD detector and a LiChrospher 100 RP-18 (urn) column (125 x 4) held at 30 °C.
  • the solvent program started from 3.6% B (2% HO Ac in acetonitrile) in solvent A (2% HO Ac in water) up to 12% B in 20 min, to 20% in 30 min, and to 50% B in 45 min.
  • Flow rate was set at mL/min and compounds were monitored by UN absorption set at 280 nm for phenolic acids, 350 nm for flavonoids and 520 nm for anthocyanins.
  • Example 3 Red Blood Cell Membrane Preparation and ATPase Assay Erythrocyte membranes were prepared as previously described (Farrance, ML., & Nincenzi, FF. (1977) Biochim Biophys Acta 471:49-58). Briefly, blood was taken from healthy humans. Red blood cells were washed with saline and lysed in a hypotonic imidazole buffer (pH 7.4, 20 mM, Sigma) with EGTA (100 mM, Sigma) and PMSF (10 mM, Sigma).
  • Membranes were washed with imidazole buffer (20 mM) containing EGTA and PMSF, imidazole buffer containing EGTA, and only imidazole buffer each one time in sequence. The final wash was in 40 mM histidine-imidazole buffer (pH 7,4), and the membranes were stored in a refrigerator (4-8°C) under nitrogen. Prior to assay, RBC membrane (0.75 mg/mL) was incubated for 30 minutes at 37°C with 0, 0.25, 1, 2.5 mg/mL of passion fruit skin extract and enough saline to achieve a final volume of 1 mL.
  • the typical assay mixture contained RBC membrane (75 ⁇ g/mL), 18 mM histidine-imidazole (pH 7.1, Sigma), 3 mM MgCI 2 , 80 mM ⁇ aCI, 15 mM KC1, 0.2 mM CaCI 2 , 0.1 mM EGTA, 0.1 mM Ouabain (Sigma) and 30 nM CaM (only for CaM-activated Ca 2+ pump, Sigma).
  • Systolic blood pressure was measured by tail cuff method (Softron, Co. Ltd, Tokyo, Japan). After 8 weeks of feeding, all the rats were sacrificed under anesthesia with Nembutal (O.lmg/lOOg body weight, Wako, Co. Ltd., Japan). Thymus, spleen, liver and heart were isolated and weighed. No toxicity was observed.
  • Example 5 Nitric Oxide Measurement Measurement of nitric oxide was carried out as previously described (Rockett,
  • Nitric oxide is easily converted to nitrite. Nitrate was measured for nitric oxide. Dilutions of NaN0 2 (BDH; Wako, Co. Ltd., Japan) and test compounds were made in distilled water in 96-well, flat-bottom plates to a final volume of 50ul. 20 microliters of NH 4 C1 borate buffer was added to all wells requiring analysis for nitric oxide/nitrite.
  • Example 6 Human Study People with hypertension, 14 men aged 57.0 ⁇ 14.48 y (mean ⁇ SD) and 16 women aged 57.56 ⁇ 12.75 y (mean ⁇ SD), were included in the study. Patients had hypertension of stage 1 or 2 according to the guidelines of the Joint National Committee on Detection, Evaluation, and Treatment of High Blood Pressure. In repeated blood pressure measurements, they had systolic blood pressure (SBP) between 144 and 210 mm Hg and diastolic blood pressure (DBP) between 80 and 120 mm Hg.
  • SBP systolic blood pressure
  • DBP diastolic blood pressure
  • the exclusion criteria included those with renal or cardiac disease, taking oral contraceptives, use of tobacco and alcohol, or taking any vitamin supplements other than a single, daily multivitamin tablet.
  • Example 7 Isolation of Edulilic Acid from Passion Fruit Peel Extract
  • Passion fruit peel extract prepared according to Example 1 was dissolved in 50% aqueous ethanol and was treated on a Sephadex LH20 column and eluted with 50% aqueous ethanol.
  • the chromatographic fractions were collected in 20 ml tubes with the aid of a fraction collector. Fractions were monitored by thin layer chromatography using cellulose TLC developed with 6% aqueous acetic acid and visualized under UV. Under this condition, the novel compound (Rf 0.8) co-eluted with the colored anthocyanins fraction (Rf 0.4-0.5). This fraction was collected and concentrated and re- chromatographed on a column of MCI GEL CHP 20P purchased from Mitsubishi
  • the electron shift can go from the C-2 protons through the acetic acid moiety, or from the acetic acid moiety and travel in the opposite direction to afford the same cis/trans result.
  • the NOESY spectrum of edulilic acid in D 2 0 shows that there is some interaction of the sugar anomeric proton with the methylene protons on C-l as numbered in the structure shown earlier (Figs. 6a and 6b). This is only possible if the carboxylic acid moiety is on the double bond side of the cyclopentene ring.
  • Example 8 Detection of Edulilic acid in the Pulp of Passion Fruit
  • An aqueous extract of passion fruit pulp was prepared in a similar manner as described in Example 1 with respect to the skin, and its chemical profile was examined using HPLC.
  • a different HPLC solvent programming using methanol instead of acetonitrile was used successfully to resolve the edulilic acid and prunasin peaks.
  • ELSD Evaporative Light Scattering Detection
  • Figs 7a and 7b show the HPLC chromatograms of the extracts of the skin and pulp respectively obtained under such conditions. While the skin and pulp extracts were clearly distinguishable by their HPLC profile, it was also apparent that both edulilic acid and prunasin were present in both extracts.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Epidemiology (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Botany (AREA)
  • Medical Informatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Fodder In General (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Selon l'invention, on prépare un extrait de fruit de la passion. Cet extrait produit un abaissement de la pression sanguine et des taux sériques d'oxyde nitrique chez les mammifères. Ledit extrait produit en outre un effet hépatoprotecteur ainsi qu'un effet antioxydant et anti-inflammatoire chez les mammifères. Un nouveau composé a été identifié dans cet extrait et appelé acide édulilique.
PCT/US2005/011244 2004-04-02 2005-04-04 Extraits de fruit de la passion et utilisations de ces extraits Ceased WO2005097153A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP05733041A EP1763360A4 (fr) 2004-04-02 2005-04-04 Extraits de fruit de la passion et utilisations de ces extraits
NZ550120A NZ550120A (en) 2004-04-02 2005-04-04 Extracts of passion fruit and uses thereof
CA002561951A CA2561951A1 (fr) 2004-04-02 2005-04-04 Extraits de fruit de la passion et utilisations de ces extraits
JP2007506337A JP2007531734A (ja) 2004-04-02 2005-04-04 パッションフルーツの抽出物及びその使用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NZ532138 2004-04-02
NZ53213804 2004-04-02

Publications (2)

Publication Number Publication Date
WO2005097153A2 true WO2005097153A2 (fr) 2005-10-20
WO2005097153A3 WO2005097153A3 (fr) 2005-12-15

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PCT/US2005/011244 Ceased WO2005097153A2 (fr) 2004-04-02 2005-04-04 Extraits de fruit de la passion et utilisations de ces extraits

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EP (1) EP1763360A4 (fr)
JP (1) JP2007531734A (fr)
CA (1) CA2561951A1 (fr)
NZ (1) NZ550120A (fr)
WO (1) WO2005097153A2 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1854470A1 (fr) 2006-05-04 2007-11-14 Industrial Research Limited, L.L.C. Procédé pour le traitement de troubles inflammatoires à base d'extraits de fruit de la passion
WO2012001687A3 (fr) * 2010-06-28 2012-04-05 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Extrait naturel neuro-protecteur
CN111728198A (zh) * 2020-07-01 2020-10-02 彭明健 一种柔肝健脾的酸甘化组合物和制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0615781D0 (en) * 2006-08-09 2006-09-20 Coressence Ltd Prebiotic composition
SI2415743T1 (sl) 2009-04-03 2015-11-30 Morinaga & Co., Ltd. Piceatanol vsebujoč sestavek in postopek proizvodnje piceatanol vsebujočega sestavka
JP7021773B2 (ja) * 2018-02-15 2022-02-17 国立大学法人 鹿児島大学 パッションフルーツ果皮に含まれる赤色系色素及びその製造方法

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US4255336A (en) * 1977-11-25 1981-03-10 Ciba-Geigy Corporation Process for the preparation of O-substituted derivatives of (+)-cyanidan-3-01
JPS6277328A (ja) * 1985-09-30 1987-04-09 Shiseido Co Ltd 循環改善剤
JPH06293657A (ja) * 1993-04-02 1994-10-21 Nippon Mektron Ltd アンジオテンシン変換酵素阻害作用剤およびアルド−スリダクタ−ゼ阻害作用剤
KR100547497B1 (ko) * 1999-07-02 2006-02-01 메이지 세이까 가부시끼가이샤 식품 조성물, 그의 제조법 및 그것을 함유하는 기능성음식품
JP2001335498A (ja) * 2000-05-26 2001-12-04 Nippon Flour Mills Co Ltd 美白組成物及びそれを含む食品及び化粧品
EP1328282B1 (fr) * 2000-08-31 2006-05-31 Phenolics, LLC Procede de production a haut rendement de compositions enrichies en anthocyanes
JP4992008B2 (ja) * 2003-08-29 2012-08-08 独立行政法人産業技術総合研究所 エンドセリン−１産生抑制剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP1763360A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1854470A1 (fr) 2006-05-04 2007-11-14 Industrial Research Limited, L.L.C. Procédé pour le traitement de troubles inflammatoires à base d'extraits de fruit de la passion
WO2012001687A3 (fr) * 2010-06-28 2012-04-05 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Extrait naturel neuro-protecteur
CN111728198A (zh) * 2020-07-01 2020-10-02 彭明健 一种柔肝健脾的酸甘化组合物和制备方法

Also Published As

Publication number Publication date
JP2007531734A (ja) 2007-11-08
CA2561951A1 (fr) 2005-10-20
WO2005097153A3 (fr) 2005-12-15
EP1763360A2 (fr) 2007-03-21
EP1763360A4 (fr) 2009-08-19
NZ550120A (en) 2010-10-29

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