WO2007080515A1 - Extrait de krill prevenant la thrombose - Google Patents

Extrait de krill prevenant la thrombose Download PDF

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Publication number
WO2007080515A1
WO2007080515A1 PCT/IB2007/000099 IB2007000099W WO2007080515A1 WO 2007080515 A1 WO2007080515 A1 WO 2007080515A1 IB 2007000099 W IB2007000099 W IB 2007000099W WO 2007080515 A1 WO2007080515 A1 WO 2007080515A1
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WO
WIPO (PCT)
Prior art keywords
krill
krill oil
composition
patient
oil extract
Prior art date
Application number
PCT/IB2007/000099
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English (en)
Inventor
Peter Mose Larsen
Stephen John Fey
Original Assignee
Aker Biomarine Asa
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 Aker Biomarine Asa filed Critical Aker Biomarine Asa
Publication of WO2007080515A1 publication Critical patent/WO2007080515A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/12—Production of fats or fatty oils from raw materials by melting out
    • C11B1/14—Production of fats or fatty oils from raw materials by melting out with hot water or aqueous solutions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • 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
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B1/00—Production of fats or fatty oils from raw materials
    • C11B1/02—Pretreatment
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

Definitions

  • This invention relates to novel extracts derived from krill, which can prevent and/or treat thrombosis.
  • This invention also relates to a method for the extraction of lipid fractions from krill in order to obtain the novel extracts of the present invention. More specifically, the invention relates to an improved method of extracting lipid fractions without using high temperatures and/or organic solvents.
  • Krill is the common name for small, shrimp-like crustaceans that swarm in dense shoals, especially in Antarctic waters. It is one of the most important food sources (especially protein) for fish, some kind of birds and especially for baleen. Krill is also a good source of omega-3 fatty acids, which are well known for their beneficial effects on human health.
  • krill and/or marine enzymes for the treatment of a great variety of diseases in human and animals such as infections, inflammations, cancers, HIV/AIDS, pain, polyps, warts, hemorrhoids, plaque, wrinkles, thin hair, allergic itch, anti-adhesion, eye disease, acne, cystic fibrosis and immune disorders including autoimmune diseases and cancer.
  • krill and/or marine oils may be used for the treatment of autoimmune murine lupus and other autoimmune diseases and can also be used for treating cardiovascular diseases.
  • US Patent 6,800,299 discloses a method for extracting lipid fractions from marine and aquatic animal material by acetone extraction.
  • the resulting non-soluble and particulate fraction is preferably subjected to an additional solvent extraction with an alcohol, preferably ethanol, isopropanol or t-butanol or an ester of acetic acid, preferably ethyl acetate to achieve extraction of the remaining soluble lipid fraction from the marine and aquatic animal material.
  • an alcohol preferably ethanol, isopropanol or t-butanol or an ester of acetic acid, preferably ethyl acetate
  • the remaining non-soluble particulate content is also recovered since it is enriched in proteins and contains a useful amount of active enzymes.
  • a krill extract is also provided herein. It is reported that these marine and aquatic animal oils have anti-inflammatory properties. Marine and aquatic animal oils are also reported as helpful in reducing the incidence of cardiovascular disease. As a further example the patent mentions that krill may be used as a source of enzymes for debridement of ulcers and wounds or to facilitate food digestion.
  • WO02102394A2 discloses a process for the preparation of a krill oil extract, which process includes the steps of placing krill and/or marine material in a ketone solvent to achieve extraction of the soluble lipid fraction from the krill; then separating the liquid and solid contents; then recovering a first lipid rich fraction from the liquid contents by evaporation of the solvent present in the liquid contents; then placing the solid contents in an organic solvent to achieve extraction of the remaining soluble lipid fraction from the krill material; then separating the liquid and solid contents; then recovering a second lipid rich fraction by evaporation of the solvent from the liquid contents; and finally recovering the solid contents.
  • Diseases that can be treated and/or prevented by using the krill oil extract are inter alia cardiovascular diseases.
  • the Krill oil has been shown to decrease cholesterol in vivo, inhibit platelet adhesion and plaque formation and reduce vascular endothelial inflammation in a patient.
  • Canadian Patent 1 ,098,900 describes a method for extracting oils and producing proteins from krill comprising emulsification of lipids of krill in an aqueous medium, separation of the emulsion of lipids from the krill mass, alkaline extraction of proteins from the krill mass, separation of the protein extract produced from chitin integuments, and finally separation of protein from the protein extract.
  • krill is a prospective source of food and other practically useful products such as chitin and lipids which find wide application in different branches, such as food industry, textile, and medicine.
  • WO03011873A2 discloses a phospholipid extract from inter alia krill, with therapeutic properties, such as those essential for the maintenance of a healthy cardiovascular system.
  • the phospholipid extract comprises a variety of phospholipids, fatty acid, metals and a novel flavonoid.
  • the method for the preparation of this extract is generally carried out by a method similar to the one described in US Patent 6,800,299 (see above; includes organic solvents), which procedure produces two successive lipid fractions and a dry residue enriched in protein, including active enzymes.
  • WO8401715A1 and WO09533471A1 disclose various aspects of so-called krill enzymes, which are water-soluble. It is mentioned that in krill a mixture of different enzymes exists, such as e.g. proteinases (with acidic and neutral-to-alkaline pH-optima), peptidases (exo- and endopeptidases), lipases, phospholipases, amylases and other carbohydrate degrading enzymes, phosphatases nucleases, nucleotidases and esterases.
  • the proteolytic (trypsin-like) activity existing in a water extract from krill has been studied and described.
  • WO09533471A1 disclose the use of one or more krill enzymes for the manufacture of an intravasal pharmaceutical composition for thrombolysis in a mammal host.
  • krill oil prepared by a novel process, which is from a physical-chemical point of view very gentle to the krill material due to relatively low temperature and no use of organic solvents, comprises other therapeutically valuable components than known from conventional krill oil extracts as well as other known fish oil; such components include inter alia high molecular (MWt > 200 kDa) hydrophobic proteins.
  • a novel krill oil extract for the prevention and/or treatment of thrombosis.
  • the general extraction method of the present invention will now be described.
  • the starting material consisting of freshly harvested and preferably finely divided krill material, is subjected to extraction, for about two hours and preferably overnight.
  • extraction time is not critical to the yield of lipid extraction.
  • particles of less than 0.5 mm in diameter.
  • Extraction is preferably conducted under inert atmosphere and at a temperature in the order of about 5° C or less.
  • the inventors have also envisaged that the present invention may be carried out by applying supercritical CO2 extraction.
  • the beginning of the extraction will be conducted under agitation for about 10 to 40 minutes, preferably 20 minutes.
  • the solubilized lipid fractions are separated from the solid material by standard techniques including, for example, filtration, centrifugation or sedimentation. Filtration is preferably used.
  • a novel krill extract for prevention and/or treatment and/or therapy of thrombosis.
  • the novel oil extract is derived from krill found in any marine environment around the world, for example, the Antarctic ocean (euphasia superba), the Pacific ocean (euphasia pacifica), the Atlantic ocean, the Indian ocean, in particular coastal regions of Mauritius Island and/or Reunion Island of Madagascar, Canadian West Coast, Japanese Coast, St-Lawrence Gulf and Fundy Bay, and this oil extract is a lipid fraction.
  • a method for extracting lipid fractions from krill comprising the steps of:
  • a method for extracting lipid fractions from krill comprising the steps of:
  • a pharmaceutical composition for the treatment of thrombosis in a patient comprising an effective amount of a krill oil extract obtainable by a method according to the present invention.
  • omega-3 fatty acid refers to polyunsaturated fatty acids that have the final double bond in the hydrocarbon chain between the third and fourth carbon atoms from the methyl end of the molecule.
  • Non-limiting examples of omega-3 fatty acids include, but are not limited to 5,8,11 ,14,17-eicosapentaenoic acid (EPA), 4,7,10,13,16,19-docosahexanoic acid (DHA) and 7,10,13,16,19-docosapentanoic acid (DPA).
  • the method of preparation is a continuous flow process and so the times given represent the average time that the material is in each stage of the process and the temperatures are typical (and may vary by ⁇ 3°C).
  • the freshly captured krill are fed into the grinder together with process water and shredded at 2 0 C for 5 minutes.
  • the slurry is then passed into a heat exchanger and warmed gently up to a temperature about 35 0 C (max below 4O 0 C) (1-2 minutes) and then stored in a buffer tank for 5 to 10 minutes. All subsequent processes occur at temperatures below 4O 0 C.
  • a centrifugal decanter is then used to separate the solid material from the liquid (3 minutes).
  • the liquid fraction is then stored in a buffer tank for 5 to 10 minutes.
  • the temperature of the liquid is adjusted to 35 0 C using a countercurrent plate heat exchanger (1 minute).
  • the stock is diluted sequentially (1 :10), shaking for 6 minutes at each dilution.
  • Blood samples were taken from normal subjects. 3.8 mm plastic tubes containing 0.38 ml 0.129M sodium citrate buffer (CPD buffer, pH 5.5) were used to store the blood. The buffered blood was then mixed with the krill or fish oil to achieve a final oil concentration varying from 5x10 "2 to 5x10 "18 Vol%. The blood cells were treated with krill or fish oil for 60 minutes before aggregation tests were performed. Blood aggregation time
  • the thrombocyte aggregation tests were performed with a PFA 100 aggregometer (Dade Bering), which is a microprocessor controlled apparatus with single test vials.
  • the unit comprises a small reservoir, a capillary and a membrane, which is covered with 2 mg genuine, type 1 collagen and 50 mg adenosin-5 ' -diphosphate (ADP).
  • ADP adenosin-5 ' -diphosphate
  • the blood is pipetted directly into the reservoir and aspirated through a capillary with a diameter of 200 ⁇ m with a constant negative pressure resulting in high shear stress.
  • the capillary ends with a membrane having an aperture with a diameter of 150 ⁇ m.
  • the thrombocytes are then activated by collagen and ADP.
  • the test Upon aggregation the blood flow is stopped due to clogging, which is referred to as closing time.
  • the test automatically stops after 300 seconds.
  • the normal value is between 62.5
  • Dilute krill oil solutions were added to whole human blood samples and allowed to react in accordance with the following steps:
  • Figure 2 shows the effects of various oils on the rate of aggregation of human whole blood.
  • the fish oil can be diluted to a concentration of only about I x IO "4 before it looses its effect.
  • a commercially available krill oil can be diluted to about 5 x 10 '6 before it looses its effect (i.e. it is about 500 times more effective than fish oil).
  • Krill oil prepared in the manner described here can be diluted to a concentration of about 5 x 10 "12 before it looses its effect. This is a million times more effective than the existing krill oil preparations and five hundred million times better than fish oil (note that the abscissa is a logarithmic scale).
  • Figure 3 shows the inhibiting effect of krill oil on the aggregation of thrombocytes in blood samples from 6 subjects. It also appears that the effect varies from subject to subject; and furthermore blood from one of the subjects was not influenced at all by the presence of krill oil.
  • Krill oil A Krill caught in large nets and subjected to a long process time
  • Krill oil B Krill caught in smaller nets and subjected to a short process time
  • Fish oil B Pikasol (OTC registered natural pharmaceutical containing concentrated Omega-3 rich fish oil; contains 62% omega-3 fatty acids, mainly EPA and DHA; Pikasol is produced from highly refined fish oil from the cleanest oceans in the world)
  • the oils are dissolved in a 1 :1 mixture with glycerol and CPD (Gly/CPD-mixture). Every single dillution is performed with the Gly/CPD-mixture to ensure that the glycerol concentration remains constant about 5x10 "3 Vol%.
  • Krill oil prepared by the process according to the present invention has a strong inhibitory effect on human thrombocyte aggregation in blood samples
  • the difference between the intensity of the effect may possibly be ascribed to certain proteins of the krill oil, and
  • Phospholipids are to be extracted from the solid fraction obtained in example 1 (step 4) using ethanol. After removal of the ethanol, the phospholipids are to be mixed with the krill oil phase obtained from the liquid fraction in example 1 (step 7) into a krill oil composition.
  • the antithrombotic effects of this krill oil composition are to be compared with other krill oil products extracted with organic solvents by investigating the effect on the aggregation time of thrombocytes in-vitro.
  • the krill oil products (mixtures of krill triglycerides and krill phospholipids) for this comparison are to be extracted from krill or krill meal using organic solvents as described in US 6,800,299. It is to be observed that the anti-thrombotic effects of the krill oil composition obtained by the methods described herein are superior to any krill oil product extracted with organic solvents such as acetone.
  • the krill oil compositions tested in example 4 are to be administered in humans (in- vivo) for a period of 5 weeks. Diets are to contain approximately 38% of energy as fat excluding the lipid in the supplement. Around 2 g of each product are to be administered in a way that preserves the biological effect of the krill oil. Non-limiting examples of administration are oral, sublingual or transdermal. After termination of the experiment, ex vivo and in vitro platelet aggregation, and variables of coagulation, fibrinolysis, and hematology are to be evaluated.
  • Ex vivo platelet aggregation time are to be measured by filtragometry and in vitro platelet aggregation induced by collagen and ADP measured by PFA 100 aggregometer.
  • Variables of coagulation factor VII amidolytic activity and concentrations of fibrinogen and prothrombin fragment 1 and 2) and fibrinolysis [plasminogen activator inhibitor (PAI) activity and concentrations of tissue plasminogen activator (tPA)/PAI-1 complexes] are to be determined by standard methods.
  • PAI plasminogen activator inhibitor
  • tPA tissue plasminogen activator

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  • Wood Science & Technology (AREA)
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Abstract

L'invention concerne un nouvel extrait de lipides marins pouvant être obtenu par un procédé faisant appel à une température de traitement inférieure à 60 °C; à une rupture mécanique et physique de la membrane cellulaire lipidique pour faciliter l'extraction à basse température; le traitement se déroulant sous gaz inerte afin d'empêcher l'oxydation ou la dénaturation des graisses et des protéines; des cuves de traitement intermédiaires étant maintenues à un niveau minimum afin de réduire le temps de séjour; et l'huile étant congelée immédiatement après récupération afin de la stabiliser.
PCT/IB2007/000099 2006-01-13 2007-01-15 Extrait de krill prevenant la thrombose WO2007080515A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US75895706P 2006-01-13 2006-01-13
USUS60/758,957 2006-01-13
DKPA200600058 2006-01-13
DKPA200600058 2006-01-13
US77763006P 2006-02-28 2006-02-28
USUS60/777,630 2006-02-28

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WO2007080515A1 true WO2007080515A1 (fr) 2007-07-19

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Cited By (33)

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WO2010097701A1 (fr) * 2009-02-26 2010-09-02 Aker Biomarine Asa Compositions phospholipidiques à faible viscosité
WO2010136900A2 (fr) 2009-05-28 2010-12-02 Aker Biomarine Asa Procédés d'utilisation de l'huile de krill à des fins de traitement des facteurs de risque associés aux affections métaboliques, cardiovasculaires et inflammatoires
US20110189374A1 (en) * 2008-09-26 2011-08-04 Nippon Suisan Kaisha, Ltd. Method for concentrating lipids
WO2011119228A1 (fr) 2010-03-23 2011-09-29 Virun, Inc. Nanoémulsion comprenant un sucroester d'acides gras
WO2011162802A1 (fr) 2010-06-21 2011-12-29 Virun, Inc. Compositions contenant des composés non polaires
US8337931B2 (en) 2008-06-23 2012-12-25 Virun, Inc. Compositions containing non-polar compounds
EP2548456A1 (fr) 2008-03-20 2013-01-23 Virun, Inc. Émulsions comprenant un dérivé de peg de tocophérol
US8372812B2 (en) 2009-02-26 2013-02-12 Aker Biomarine Asa Phospholipid and protein tablets
WO2013120025A1 (fr) 2012-02-10 2013-08-15 Virun, Inc. Compositions de boisson contenant des composés non polaires
WO2013127727A1 (fr) * 2012-02-29 2013-09-06 B. Braun Melsungen Ag Émulsion contenant des hormones comprenant des phospholipides de krill
US8609157B2 (en) 2009-10-30 2013-12-17 Tharos Ltd. Solvent-free process for obtaining phospholipids and neutral enriched krill oils
US8697138B2 (en) 2007-03-28 2014-04-15 Aker Biomarine As Methods of using krill oil to treat risk factors for cardiovascular, metabolic, and inflammatory disorders
AU2014100741B4 (en) * 2007-08-29 2014-09-11 Aker Biomarine Antarctic As Processes and products thereof
WO2014151109A1 (fr) 2013-03-15 2014-09-25 Virun, Inc. Formulations de dérivés solubles dans l'eau de vitamine e et compositions les contenant
US8960582B2 (en) 2011-04-27 2015-02-24 John Kelson Micro-spike algae harvesting and biofuel extraction system
CN104388188A (zh) * 2014-11-10 2015-03-04 大连工业大学 提取甘油三酯型南极磷虾油和南极磷虾磷脂的方法
US9028877B2 (en) 2007-03-28 2015-05-12 Aker Biomarine Antarctic As Bioeffective krill oil compositions
WO2016044805A1 (fr) 2014-09-18 2016-03-24 Virun, Inc. Compositions de gel mou et concentrés pré-gel
WO2016075669A1 (fr) * 2014-11-14 2016-05-19 Tharos Ltd. Procédé sans solvant d'obtention d'huiles de krill enrichies en phospholipides et en lipides neutres par fusion et par évaporation
US9351517B2 (en) 2013-03-15 2016-05-31 Virun, Inc. Formulations of water-soluble derivatives of vitamin E and compositions containing same
US9693574B2 (en) 2013-08-08 2017-07-04 Virun, Inc. Compositions containing water-soluble derivatives of vitamin E mixtures and modified food starch
US9788564B2 (en) 2008-03-20 2017-10-17 Virun, Inc. Compositions containing non-polar compounds
US9861611B2 (en) 2014-09-18 2018-01-09 Virun, Inc. Formulations of water-soluble derivatives of vitamin E and soft gel compositions, concentrates and powders containing same
US9867856B2 (en) 2014-01-10 2018-01-16 Aker Biomarine Antarctic As Phospholipid compositions and their preparation
US10016363B2 (en) 2014-09-18 2018-07-10 Virun, Inc. Pre-spray emulsions and powders containing non-polar compounds
CN108559622A (zh) * 2018-03-19 2018-09-21 中国水产科学研究院东海水产研究所 一种可用于船载的磷虾油提取方法
US10456412B2 (en) 2015-02-11 2019-10-29 Aker Biomarine Antarctic As Lipid extraction processes
US10704011B2 (en) 2013-06-14 2020-07-07 Aker Biomarine Antarctic As Lipid extraction processes
US10864223B2 (en) 2015-02-11 2020-12-15 Aker Biomarine Antarctic As Lipid compositions
CN112617011A (zh) * 2021-01-11 2021-04-09 海南大学 一种凡纳滨对虾卵巢促熟的配合饲料及其制备方法
CN114073864A (zh) * 2022-01-19 2022-02-22 华南理工大学 一种四液相体系同步萃取分离原料中多组分的方法
EP3813687A4 (fr) * 2018-06-28 2022-03-23 Marizyme Biotech Compositions pharmaceutiques et procédés pour le traitement de la thrombose et l'administration par des dispositifs médicaux
EP4005589A1 (fr) * 2006-12-05 2022-06-01 Marizyme, Inc. Composition enzymatique à libération contrôlée et procédés d'utilisation

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DE3038190A1 (de) * 1979-10-11 1981-04-23 Alfa-Laval AB, 14700 Tumba Verfahren zur herstellung von nahrungs- bzw. futtermitteln aus krill-rohmaterial
JPS6323819A (ja) * 1986-07-16 1988-02-01 Kao Corp 血小板凝集抑制剤
WO1995033471A1 (fr) * 1994-06-07 1995-12-14 Hellgren, Lars Thrombolyse intravasculaire
WO2002102394A2 (fr) * 2001-06-18 2002-12-27 Neptune Technologies & Bioressources Inc. Krill et/ou extraits marins pour la prevention et/ou le traitement des maladies cardiovasculaires, de l'arthrite, du cancer de la peau, du diabete, du syndrome premenstruel et du transport transdermique
WO2003000061A1 (fr) * 2001-06-21 2003-01-03 Transucrania, S.A. Procede de transformation de crustaces et plus particulierement de krill antarctique et semi-produits obtenus par ce procede
WO2005075613A1 (fr) * 2004-02-06 2005-08-18 Adrien Beaudoin Procede pour empecher l'oxydation de lipides dans des huiles animales et vegetales et compositions produites selon ce procede

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* Cited by examiner, † Cited by third party
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US4036993A (en) * 1975-04-25 1977-07-19 Tensei Suisan Company, Limited Process for preparation of fish meat extracts
DE3038190A1 (de) * 1979-10-11 1981-04-23 Alfa-Laval AB, 14700 Tumba Verfahren zur herstellung von nahrungs- bzw. futtermitteln aus krill-rohmaterial
JPS6323819A (ja) * 1986-07-16 1988-02-01 Kao Corp 血小板凝集抑制剤
WO1995033471A1 (fr) * 1994-06-07 1995-12-14 Hellgren, Lars Thrombolyse intravasculaire
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