WO1998026792A1 - Compositions contenant des antioxydants et procede de preparation desdits antioxydants - Google Patents

Compositions contenant des antioxydants et procede de preparation desdits antioxydants Download PDF

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Publication number
WO1998026792A1
WO1998026792A1 PCT/IL1997/000416 IL9700416W WO9826792A1 WO 1998026792 A1 WO1998026792 A1 WO 1998026792A1 IL 9700416 W IL9700416 W IL 9700416W WO 9826792 A1 WO9826792 A1 WO 9826792A1
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WO
WIPO (PCT)
Prior art keywords
juice
red
vegetables
compositions
betaxanthins
Prior art date
Application number
PCT/IL1997/000416
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English (en)
Inventor
Joseph Kanner
Stela Harel
Rina Granit
Original Assignee
State Of Israel - Ministry Of Agriculture
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 State Of Israel - Ministry Of Agriculture filed Critical State Of Israel - Ministry Of Agriculture
Priority to EP97947855A priority Critical patent/EP0948339A1/fr
Priority to AU54086/98A priority patent/AU5408698A/en
Publication of WO1998026792A1 publication Critical patent/WO1998026792A1/fr

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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
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
    • A23L2/385—Concentrates of non-alcoholic beverages
    • A23L2/39—Dry compositions
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives

Definitions

  • the present invention generally relates to compositions containing antioxidants of the betalain family and to a method for their preparation.
  • the present invention relates compositions containing natural antioxidants of the betacyanin family (betanin and betanidin) and betaxanthins from fruits and vegetables, especially red beets and prickly pear.
  • the compositions of the present invention are useful for prevention and treatment of disorders and diseases associated with oxygen derived free radicals, especially vascular diseases. Also these compositions are useful as antioxidants in food and cosmetic products.
  • the present invention further relates to a method for the preparation of these compositions.
  • LDL Low density lipoprotein
  • Betalain a natural occurring pigment, is a term that includes two classes of pigments; the betacyanins, which are red violet and the betaxanithins, which are yellow. Betalains have been detected only in red-violet, orange and yellow pigmented botanical species belonging to related families of the order caryophyllales. Of the numerous natural sources of the betalains, red beet and prickly pear are the only edibles containing these pigments.
  • betanin The major betalain in beets, betanin, accounts for most of the betacyanin content of the beet.
  • betacyanins are derived from two aglycons, betanidin and iso-betanidin. Betanin is a betanidin 5-o- ⁇ glucoside. Betanidin contains an ortho- diphenol group, which is suspected to be a very good electron donor or hydrogen donor, working as an active antioxidant.
  • betanin and betanidin are cationized molecules which may increase their protective effects on cells and organelles against oxidation.
  • Cell and organelle membranes are negatively charged and anionic sites on the cell surface have been shown to exhibit strong affinity for cationic agents.
  • successful prevention of H 2 O 2 induced damage to rat jujenal mucosa and E. coli cells by cationized catalase was described (Kohen R. and Shalhoub R. Free Rad. Biol. Med. 16: 571, 1994).
  • the present invention relates to compositions containing antioxidants, derived from antioxidant containing fruits and vegetable, preferably from red beets and prickly pear, and to a method for the preparation of these compositions.
  • the compositions of the present invention are useful for prevention and treatment of any disorders and diseases that are due to oxidative stress, a partial list of which is presented in Table 1. Summary of the invention
  • the present invention relates to compositions containing betacyanins (betanidins and betanins) and betaxanthins from antioxidant containing fruits and vegetables, preferably red beets, useful for prevention and treatment of disorders and diseases that are due to oxidative stress, especially vascular diseases.
  • betacyanins betanidins and betanins
  • betaxanthins from antioxidant containing fruits and vegetables, preferably red beets
  • compositions may be pharmaceutical compositions containing, as an active ingredient, betacyanins and betaxanthins that are extracted from antioxidant containing fruits and vegetables.
  • the present invention also relates to a method for the preparation of said compositions comprising heating red beet raw material; peeling it, extracting its juice with a juice extractor; mixing the juice and pulp with pectolytic or cellulytic enzymes or both, after which the red beet juice may be freeze dried or spray dried to a powder which can be packed in capsules.
  • Said compositions are also prepared using a Luwa concentrator.
  • betacyanins betacyanins (betanin and betanidin) and betaxanthins from fed beet was evaluated and their bioavailability in humans was determined, it was shown that the betanin of red beet juice is absorbed quickly from the gut to the blood stream. Also it was shown that cationized betanin is strongly attached to microsomes and that the betanins and other betalains in the red beet effectively prevent lipid peroxidation by active myoglobin and, because of their cationic properties, act as membrane site specific antioxidants, increasing their protective effects on cells and organelles against oxidation.
  • the said invention will be further and illustrated by the following experiments. These experiments do not intend to limit the scope of the invention but to demonstrate and clarify it only.
  • the red beets were heated by microwave at 98°c for 5 minutes , cooled to 25°c and then crushed in a blender for 1 minute. The pulp was centrifuged at 10,000g for 15 minutes at
  • betacyanins concentration of betacyanins was estimated using ⁇ value of 65,000 for betanin, 54,000 for betanidin and 60,000 for betaxanthin (figure 1).
  • Red beet juice was run on HPLC at ambient temperature.
  • the HPLC separation was done by a column of Water Novo-pack C-18, 3.9x150mm and a Merk Hitachi pump
  • the chromatograms were monitored at 535nm.
  • the betanin and betanidin fractions were further separated by HPLC using the method described in Schwartz S.J. and von Elbe
  • Betanin the main pigment in red-beet roots, attains a concentration of 600 mg/1 in several varieties (Schwartz S.J. and von Elbe J.H.J. Agric Food Chem., 28:540, 1980). _
  • Betanin and betanidin were found to act as antioxidants in a model system containing linoleate, which its peroxidation is catalyzed by myoglobin or cytochrome C (figure 2).
  • the assay of diene conjugation was carried out according to the method described by Ben Aziz et al. Anal. Biochem. 84:38, 1970.
  • the reaction mixture contained linoleic acid (0.05%), EDTA (0.5mM) in 0.1M phosphate buffer at pH 7. Both assays employed a double beam recording.
  • ⁇ carotene - linoleate oxidation activity was assayed colorimetrically as described in Kanner J. Am. Oil.
  • the technique consists of following the decrease in absorbance at 460nm in the cuvette of a double beam recording spectrophotometer.
  • the test sample contained 1.5 ml of buffered carotene - linoleate mixture at pH 7, 0.1 - 0.4 ml active fraction and distilled water, in a mixture as follows: ⁇ carotene 14 ⁇ M, linoleate 2mM, linoleate acid hydroperoxydes 2 ⁇ M, Tween 20, 0.05% phosphate buffer pH 7 0.1M, EDTA 0.5M (except in the model catalyzed by Fe- ascorbic acid).
  • the blank sample contained all the reagents except ⁇ carotene.
  • LDL Low density lipoproteins
  • Plasma LDL was prepared as described in Frankel et al. Lancet 341:434, 1993.
  • LDL Prior to the oxidation experiments LDL were exhaustively dialyzed with deoxygenated phosphate buffered (lOmM, pH 7.4) saline (lOOmM) for 24 hours. The final concentration of each sample was diluted to an equal protein content (0.25mg/ml LDL) with phosphate buffered saline (lOmM). The oxidative susceptibility of LDL was evaluated.
  • LDL oxidation was determined by oxygen absorption during lipid peroxidation of LDL in a reaction system containing activated metmyoblobin (30 ⁇ M), 30 ⁇ M H 2 O 2 , using oxygen monitor with a Clark electrode. Spectral changes showing the reduction of ferryl myoglobin radical with betanin and betanidin were determined spectrophotometrically at 545nm and 575 nm after interaction of equimolar concentration of metmyoglobin with H 2 O 2 (50 ⁇ M).
  • betanin and betanidin inhibit linoleate peroxidation 3 and 1.3 fold respectively, better than catechin, a well known antioxidant found in large concentrations in many fruits and vegetables, especially in wines and tea.
  • betanin was found to be 15 fold more active than ⁇ tocopherol, the natural membrane antioxidant.
  • Betanin antioxidant activity was also examined in a model system containing activated myoglobin which initiate microsomal lipid peroxidation.
  • I 5 o of betanin was less than 2.5 ⁇ M, and much lower than that of several flavonoids and phenolic acids such as catechin, quercetin, caffeic and gallic acids (table 2).
  • betanin was found to inhibit human LDL oxidation much better than catechin, the most active flavonoid in wines (figure 3).
  • a peak of betanin was identified 3 hours after drinking the juice and 60 ⁇ g/50ml of urine were found (figure 4).
  • the total betanin collected in urine during 10 hours was about lOO ⁇ g, which is about 0.1% of what was ingested.
  • Figure 5 shows that red beet juice is absorbed quickly from the gut, most probably from the stomach and only after 8 - 9 hours from the intestine. Red beet slices are absorbed only partially from the stomach and mostly from the intestine.
  • betanin which is the 5-o- ⁇ -glucose of betanidin, is absorbed from the gut to the blood stream and could be identified in urine at relatively high concentrations.
  • Red beet juice is produced from heated raw material at 98°c for 30 minutes and peeled with a carborodium peeler.
  • the beets are brought to room temperature by immersion in tap water.
  • Juice is extracted from the beets by a "Santos" juice extractor.
  • the juice is mixed for 30 minutes at room temperature with the pulp and pectolytic and cellulytic enzymes Pectinex Ultra JP-L and Celluclast 1.5L respectively at concentrations of 0.1% each.
  • the juice is filtered through a Brawn machine separator and is pasteurized by a plate pasteurizer at 98°c for 10 seconds, to achieve the high temperature needed for hot filing glass bottles of 250 ml. the bottles are cooled by tap water and brought to room temperature.
  • This treatment decreases the pulp from 35% to 7% and enriches the extraction of the juice from 64 % to 92%.
  • Concentrated red beet juice is prepared by using a Luwa concentrator. By this method the juice is concentrated to 60 Brix and 80% dry matter. The concentrated red beet juice contains about 3 mg/gr betacyanins. This concentrate could be used as an additive for foods, cosmetics and nutraceuticals.
  • Red beet juice after enzymatic treatment, is freeze dried or spray dried to a powder.
  • This powder is packed in capsules of 0.5 gr which contain 2mg betacyanin each.
  • Two capsules contain 4 mg of betacyanins which is the equivalent of one glass of red beet juice produced by the above mentioned methods.
  • the dried powder may also be used as an antioxidant in food products
  • Stroke myocardial infraction, organ transplantation (heart, lung, skin, cornea, kidney), organ preservation, reattachment of severed limbs, frostbite, Dupuytren's contracture, hemorrhagic shock, endotoxic shock, crush injury
  • Hemolytic drugs lead, halogenated hydrocarbons, ozone, oxides of nitrogen, asbestos, other mineral dusts, sulfur dioxid, paraquat, aluminum, cigarette smoke, diabetogenic drugs, fava beans (hemolytic agents), anthracyclines (cardiotoxicity), heavy metals (nephrotoxicity), photosensitizing drugs, contact dermatitis
  • Keshan disease severe selenuim deficiency
  • hemolytic disease of prematurity retinopathy of prematurity
  • bronchopulmonary dysplasia intracranial hemorrhage
  • neurological degeneration due to severe vitamin E deficiency in inborn errors affecting intestinal fat absorption
  • acquired immunodeficiency syndrome severe selenuim deficiency syndrome
  • Microsomes were incubated 1 h at 37°C with buffer phosphate pH 7.0, 0.05 M.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Botany (AREA)
  • Mycology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Biotechnology (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Microbiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

La présente invention concerne des compositions contenant des bétacyanines (bétanidines et bétanines) et des bétaxanthines provenant d'un antioxydant issu des fruits et des légumes, de préférence des betteraves rouges, utilisé dans la prévention et le traitement de troubles et de maladies dus à un stress oxydatif, en particulier, les maladies vasculaires. Ces compositions peuvent être des compositions pharmaceutiques contenant, comme ingrédients actifs, des bétacyanines et des bétaxanthines extraites d'un antioxydant issu des fruits et légumes. La présente invention concerne également un procédé de préparation desdites compositions comprenant le chauffage de la matière première betterave rouge, son épluchage, l'extraction de son jus au moyen d'un extracteur de jus, le mélange dudit jus et de la pulpe avec des enzymes pectolytiques ou cellulytiques ou les deux, après quoi le jus rouge de betterave peut être séché par lyophilisation ou par pulvérisation en une poudre qui peut être conditionnée en capsules.
PCT/IL1997/000416 1996-12-19 1997-12-19 Compositions contenant des antioxydants et procede de preparation desdits antioxydants WO1998026792A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP97947855A EP0948339A1 (fr) 1996-12-19 1997-12-19 Compositions contenant des antioxydants et procede de preparation desdits antioxydants
AU54086/98A AU5408698A (en) 1996-12-19 1997-12-19 Compositions containing antioxidants and a method for their preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IL11987296A IL119872A (en) 1996-12-19 1996-12-19 Pharmaceutical compositions containing antioxidant betalains and a method for their preparation
IL119872 1996-12-19

Publications (1)

Publication Number Publication Date
WO1998026792A1 true WO1998026792A1 (fr) 1998-06-25

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EP (1) EP0948339A1 (fr)
AU (1) AU5408698A (fr)
IL (1) IL119872A (fr)
WO (1) WO1998026792A1 (fr)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6228365B1 (en) * 1996-07-24 2001-05-08 Govind Kapadia Inhibitory effect of synthetic and natural colorants on carcinogenesis
EP1703795A2 (fr) * 2003-12-31 2006-09-27 Yosi Shevach Produits a base de betterave sucriere
WO2010014839A1 (fr) * 2008-07-30 2010-02-04 Vdf Futureceuticals, Inc. Compositions de bétalaïne et leurs utilisations
WO2010090508A1 (fr) * 2009-02-06 2010-08-12 Universiti Putra Malaysia Colorant naturel et procédés associés
EP2420243A1 (fr) 2010-08-18 2012-02-22 Inovativo Biomedicinas Tehnologiju Instituts, SIA Composition obtenable du jus de betteraves rouges, pour améliorer l'absorption de fer et l'hématopoièse
WO2013058642A1 (fr) * 2011-10-17 2013-04-25 Lugo Radillo Agustin Utilisation des bétaxantines et de leurs dérivés pour préparer un médicament destiné au traitement du prédiabète et du diabète.
WO2014073946A2 (fr) * 2012-11-09 2014-05-15 Lugo Radillo Agustin Utilisation des bétalaïnes et de leurs dérivés pour la préparation d'un médicament destiné au traitement, à la prévention, à la régulation et au contrôle d'hépathopathies, de pathologies associées à infiltrat inflammatoire, de nécrose et pour la modification des dépôts de lipides
US9101587B2 (en) 2007-01-31 2015-08-11 Vdf Futureceuticals, Inc. Solid betalain compositions and methods
WO2016191736A1 (fr) 2015-05-27 2016-12-01 Vdf Futureceuticals, Inc. Compositions et procédés pour améliorer une performance athlétique
WO2019221114A1 (fr) * 2018-05-14 2019-11-21 国立大学法人北海道大学 Agent de réparation du tissu cutané contenant de la bétanine ou un composé analogue à cette dernière
WO2022184720A1 (fr) 2021-03-02 2022-09-09 Gnt Group B.V. Composition de betterave

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2399467A1 (fr) * 1977-08-01 1979-03-02 Verniers Sa Perfectionnements a la fabrication du colorant de betterave
JPS5811555A (ja) * 1981-07-14 1983-01-22 San Ei Chem Ind Ltd ベタシアニン色素製剤

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2399467A1 (fr) * 1977-08-01 1979-03-02 Verniers Sa Perfectionnements a la fabrication du colorant de betterave
JPS5811555A (ja) * 1981-07-14 1983-01-22 San Ei Chem Ind Ltd ベタシアニン色素製剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PATENT ABSTRACTS OF JAPAN vol. 007, no. 083 (C - 160) 6 April 1983 (1983-04-06) *

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6228365B1 (en) * 1996-07-24 2001-05-08 Govind Kapadia Inhibitory effect of synthetic and natural colorants on carcinogenesis
EP1703795A2 (fr) * 2003-12-31 2006-09-27 Yosi Shevach Produits a base de betterave sucriere
EP1703795A4 (fr) * 2003-12-31 2011-01-19 Yosi Shevach Produits a base de betterave sucriere
US9101587B2 (en) 2007-01-31 2015-08-11 Vdf Futureceuticals, Inc. Solid betalain compositions and methods
US10125161B2 (en) 2007-01-31 2018-11-13 Vdf Futureceuticals, Inc. Solid betalain compositions and methods
US11771713B2 (en) 2008-07-30 2023-10-03 Vdf Futureceuticals, Inc. Betalain compositions and methods therefor
US20110190230A1 (en) * 2008-07-30 2011-08-04 Zbigniew Pietrzkowski Betalain Compositions and Uses Thereof
JP2011529906A (ja) * 2008-07-30 2011-12-15 ブイ・デイ・エフ・フユーチヤーシユーテイカルズ・インコーポレイテツド ベタレイン組成物およびそれらの使用
US11026962B2 (en) 2008-07-30 2021-06-08 Vdf Futureceuticals, Inc. Betalain compositions and methods therefor
US10543224B2 (en) 2008-07-30 2020-01-28 Vdf Futureceuticals, Inc. Betalain compositions and methods therefor
US9060539B2 (en) 2008-07-30 2015-06-23 Vdf Futureceuticals, Inc. Betalain compositions and uses thereof
US9636371B2 (en) 2008-07-30 2017-05-02 Vdf Futureceuticals, Inc. Betalain compositions and methods therefor
WO2010014839A1 (fr) * 2008-07-30 2010-02-04 Vdf Futureceuticals, Inc. Compositions de bétalaïne et leurs utilisations
KR20110115127A (ko) * 2009-02-06 2011-10-20 유니버시티 푸트라 말레이지아 천연색소 및 그의 제조방법
KR101590517B1 (ko) 2009-02-06 2016-02-01 유니버시티 푸트라 말레이지아 천연색소 및 그의 제조방법
JP2012517495A (ja) * 2009-02-06 2012-08-02 ユニバーシティー プトラ マレーシア 天然着色料およびその方法
WO2010090508A1 (fr) * 2009-02-06 2010-08-12 Universiti Putra Malaysia Colorant naturel et procédés associés
EP2420243A1 (fr) 2010-08-18 2012-02-22 Inovativo Biomedicinas Tehnologiju Instituts, SIA Composition obtenable du jus de betteraves rouges, pour améliorer l'absorption de fer et l'hématopoièse
WO2013058642A1 (fr) * 2011-10-17 2013-04-25 Lugo Radillo Agustin Utilisation des bétaxantines et de leurs dérivés pour préparer un médicament destiné au traitement du prédiabète et du diabète.
WO2014073946A3 (fr) * 2012-11-09 2014-08-07 Lugo Radillo Agustin Utilisation des bétalaïnes et de leurs dérivés pour la préparation d'un médicament destiné au traitement, à la prévention, à la régulation et au contrôle d'hépathopathies, de pathologies associées à infiltrat inflammatoire, de nécrose et pour la modification des dépôts de lipides
WO2014073946A2 (fr) * 2012-11-09 2014-05-15 Lugo Radillo Agustin Utilisation des bétalaïnes et de leurs dérivés pour la préparation d'un médicament destiné au traitement, à la prévention, à la régulation et au contrôle d'hépathopathies, de pathologies associées à infiltrat inflammatoire, de nécrose et pour la modification des dépôts de lipides
WO2016191736A1 (fr) 2015-05-27 2016-12-01 Vdf Futureceuticals, Inc. Compositions et procédés pour améliorer une performance athlétique
EP4233877A2 (fr) 2015-05-27 2023-08-30 VDF Futureceuticals, Inc. Compositions et procédés pour améliorer une performance athlétique
WO2019221114A1 (fr) * 2018-05-14 2019-11-21 国立大学法人北海道大学 Agent de réparation du tissu cutané contenant de la bétanine ou un composé analogue à cette dernière
JPWO2019221114A1 (ja) * 2018-05-14 2021-06-10 国立大学法人北海道大学 ベタニンまたはその類似化合物を含む皮膚組織修復剤
WO2022184720A1 (fr) 2021-03-02 2022-09-09 Gnt Group B.V. Composition de betterave

Also Published As

Publication number Publication date
IL119872A0 (en) 1997-03-18
EP0948339A1 (fr) 1999-10-13
IL119872A (en) 2000-01-31
AU5408698A (en) 1998-07-15

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