WO2014167162A1 - Extracto antioxidante a partir de macroalgas pardas y procedimiento de obtención - Google Patents

Extracto antioxidante a partir de macroalgas pardas y procedimiento de obtención Download PDF

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Publication number
WO2014167162A1
WO2014167162A1 PCT/ES2014/070288 ES2014070288W WO2014167162A1 WO 2014167162 A1 WO2014167162 A1 WO 2014167162A1 ES 2014070288 W ES2014070288 W ES 2014070288W WO 2014167162 A1 WO2014167162 A1 WO 2014167162A1
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Prior art keywords
extract
macroalga
lyophilized
water
macroalgae
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Ceased
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PCT/ES2014/070288
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English (en)
Spanish (es)
French (fr)
Inventor
Jorge Sineiro Torres
Marivel SÁNCHEZ GUERRERO
María José NÚÑEZ GARCÍA
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Universidade de Santiago de Compostela
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Universidade de Santiago de Compostela
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Priority to US14/784,203 priority Critical patent/US20160074317A1/en
Priority to EP14782293.6A priority patent/EP2997963A4/en
Priority to CN201480033395.3A priority patent/CN105377232A/zh
Priority to JP2016507014A priority patent/JP2016522171A/ja
Priority to KR1020157032242A priority patent/KR20150140382A/ko
Publication of WO2014167162A1 publication Critical patent/WO2014167162A1/es
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23BPRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00Preservation of foods or foodstuffs, in general
    • A23B2/70Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729Organic compounds; Microorganisms; Enzymes
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L17/00Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/60Edible seaweed
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/02Algae
    • A61K36/03Phaeophycota or phaeophyta (brown algae), e.g. Fucus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34Alcohols
    • A61K8/347Phenols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics 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
    • A61K8/9706Algae
    • A61K8/9711Phaeophycota or Phaeophyta [brown algae], e.g. Fucus
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics 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
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00Food compositions, function of food ingredients or processes for food or foodstuffs
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23VINDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00Function of food ingredients
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10General cosmetic use
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52Stabilizers
    • A61K2800/522Antioxidants; Radical scavengers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/82Preparation or application process involves sonication or ultrasonication
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/84Products or compounds obtained by lyophilisation, freeze-drying

Definitions

  • the present invention relates to the extraction of compounds from macroalgae. More specifically, the invention relates to the extraction of antioxidants from brown macroalgae.
  • Antioxidants are secondary metabolites present in macroalgae, plants, and particularly in fruits. They are compounds that inhibit or prevent the oxidation of a substrate.
  • synthetic antioxidant compounds such as butylated hydroxytoluene (BHT), propyl gallate or butyrohydroxyanisole (BHA) are used.
  • BHT butylated hydroxytoluene
  • BHA butyrohydroxyanisole
  • Natural antioxidants such as those from grape extracts, rosemary, cocoa, etc., are being better welcomed due to their low toxicity and high antioxidant activity.
  • a large family of antioxidant compounds are the florotannins present in macroalgae that show good antioxidant activity
  • Phenolic Compounds in the Brown Seaweed Ascophyllum nodosum Distribution and Radical-scavenging Activities, Audibert, L, Fauchon.M., Blanc.N., Hauchard, D.
  • the extracts obtained from the treatment of brown macroalgae can be used for food, cosmetic and / or pharmaceutical consumption because of their content in fucoidans and florotannins.
  • brown macroalgae such as Bifurcaria bifurcata and Ascophyllum nodosum
  • the high content in fucoidanos causes that these extracts possess a humectante capacity in the skin, whereas the antioxidant power comes given by the presence of florotaninos.
  • the obtaining of a natural product that does not possess a strong characteristic aroma is desirable for its use as a cosmetic ingredient so as not to interfere with other desired ones, which is favored with aqueous extraction and avoiding the use of organic solvents.
  • Another desirable characteristic of the extract extraction process is that the solvents used are cheap, renewable, of low or no toxicity and that its
  • Crude extracts or isolated fractions often exhibit higher antioxidant activity than synthetic antioxidants such as BHA (butyrohydroxyanisole) or BHT (butyrohydroxytoluene).
  • BHA butyrohydroxyanisole
  • BHT butyrohydroxytoluene
  • the process object of the present invention allows to use water to obtain a stable product, easy to handle and add to different products and free of traces of 30 solvents.
  • the method of extracting the antioxidant from a brown macroalga comprises: a) If fresh macroalga is used, it is washed with running water that removes sands and epiphytes, and then dried with absorbent paper. In the case that dry seaweed is used, this cleaning process with water is not necessary. b) The dry or fresh algae is then mixed with water at a liquid / solid (L / S) ratio between 3 and 5 g / g. c) The previous mixture is then subjected to a grinding process, preferably in a blade mill, until the particle size is reduced between 0.5 and 2 mm for dry macroalga and between 0.5 and 3 mm for fresh macroalga. d) Mix the crushed macroalga with a liquid solvent comprising pure ethanol or mixtures ethanol: water in a ratio of 1: 1 v / v, in a Liquid / Solid (L / S) ratio of between 5 and
  • the product is stored refrigerated at less than 5 ° C and protected from light to prevent its alteration.
  • the invention relates to a stable antioxidant extract obtained from the processing of brown macroalgae, more specifically macroalgae algae of the species Bifurcaria bifurcata, Ascophyllum nodosum, Saccorhiza polysrissas and Sargassum muticum BRIEF DESCRIPTION OF THE FIGURES
  • Figure 1 shows the scheme for ultrasound-assisted cell disruption in a continuous macroalgal feeding system.
  • Figure 2 shows the detection of florotannins by HPLC on a C18 reverse phase column.
  • Figure 3 shows the ultraviolet profile of the extract of Bifurcaria bifurcata, with a characteristic profile of florotannins and similar to that of phloroglucinol.
  • the invention is directed to an aqueous antioxidant extract obtained from brown macroalgae characterized by a) a carbohydrate content between 33 and 156 mg glucose / g lyophilized; b) a content of fucoidan, expressed as total sulfates after digestion of the sample, between 44 and 118 mg of sulphates / g of lyophilisate; c) a content of florotannins, expressed as phloroglucinol, between 12 and 62.4 mg phloroglucinol equivalents / g lyophilisate; and d) a content in alginates, between 10 and 55 mg equivalents of glucuronic acid / g of lyophilizate.
  • the invention is directed to a cosmetic and / or food composition comprising the antioxidant extract object of the present invention.
  • FIG. 1 is shown the scheme for ultrasonic assisted cell disruption in a continuous macroalgal feed system composed of an ultrasonic generating unit that includes a sonotrode (105) disposed in a continuous flow cell (104), which is fed by a main peristaltic pump (102) and a recirculation pump (103).
  • the extraction process of the aqueous antioxidant compound comprises the following steps: a) 120 g of fresh macroalga were washed with potable water and subsequently with distilled water. b) 300 mL of water were added c) The macroalga was pre-crushed, by operating a blade mixer for 10 min, obtaining a particle size of less than 3 mm. d) Water was added to the preparation obtained in the previous step until obtaining an L / S ratio of 10 and it was introduced in a feed tank (100) that is mixed by means of a stirrer (101).
  • Table 1 One of the extraction conditions described in Table 1 was selected, which summarizes a 2 2 factorial experimental design with 4 central points.
  • the continuous ultrasonic extraction conditions considered the power parameters (such as amplitude or percentage of the applied nominal power) and recirculation ratios of the inlet flow rate of the alga broth to the continuous flow cell (sonicated or ultrasonic cell) ( 104) in which a sonotrode (105) continuously applies ultrasonics to the mixture with a power density in the range between 3 and 13 W / cm 3 .
  • Table 1 summarizes the combination of treatments performed for the experimental design.
  • the extraction assembly requires an ultrasound-assisted extraction system as shown in Figure 1.
  • the sedimentable solid residue was allowed to settle and separated from the supernatant by decantation.
  • the next step was to centrifuge and separate the supernatant again.
  • a lyophilized extract (106) was obtained, which in this particular embodiment comprises a total volume of 1400 mL in which and finally to obtain a solid and dry extract.
  • Amplitude adjustment codes -1, 0 and 1 correspond to amplitudes of 50%, 70% and 90%.
  • Recirculation ratio codes -1, 0 and +1 correspond to 1, 1 .5 and 2, with a constant recirculation flow rate of 300 mL / min
  • the extraction performance on a wet basis from fresh macroalga is within a range of 2.9 - 6.6% (w / w); while the yield of extraction for dry seaweed is within the range 27.7 and 57.3% (w / w); the yields for each of the algae species analyzed are shown in Table 2.
  • the maximum absorbance of this lyophilized extract and subsequently redissolved in water, compared to a water target is between 250 nm and 280 nm, as It is collected in Figure 3.
  • Polyphenols means a whole family of compounds present in vegetables, which contains or are derived from the phenol group: benzoic acid derivatives, cinnamic acid derivatives, flavonoids, etc.
  • the DPPH radical inhibition assay proposed in "Use of a free radical method to evaluate antioxidant activity", Brand-Williams W, Cuvelier ME, Berset C. LWT Food Sci Technol 28: 5-30 18 (1995), was used to determine the donor capacity of protons by the extract. The method was applied with a slight modification as described, where to 980 ⁇ _ of a methanolic solution of the radical (6.9 * 10 "5 mol / L) was added 20 ⁇ _ of an aqueous solution of the extract.
  • Polysaccharides are understood as the polymers formed from sugars, mainly hexoses and / or pentoses, which function as a structural component and energy reserve in vegetables.
  • the content of polysaccharides was determined by the phenol-sulfuric method, proposed in Colorimetric method for determination of sugars and related substances, Dubois, M .; Gil ⁇ es, K. A .; Hamilton, J. K .; Rebers, P. A .; Smith, F. Anal. Chem., 28, 350-356, 1956.
  • An average carbohydrate content of 156.7 mg of glucose / g of lyophilisate was obtained from the extract obtained from the macroalga Bifurcaria bifurcata, being 29% higher than that obtained from Ascophyllum nodosum in similar conditions.
  • Fucoidans are a family of polysaccharides characteristic of algae, which are formed by polymerization of fucose derivatives, a sulfated sugar.
  • the average content of fucoidan was determined by the procedure described in Determination of inorganic sulphate in studies on the enzymatic and non-enzymic hydrolysis of carbohydrate and other sulphate esters, Dodgson, Dodgson, KS. Biochem. J., 78, pp. 312-317, 1961, and is expressed as total sulfates after digestion of the sample.
  • the average value in extracts of Bifurcaria bifurcata is 1 18 mg of sulfates / g of lyophilisate, 134% higher than an extract of Ascophyllum nodosum obtained in similar conditions.
  • Sulfur levels determined by ICP-OES techniques (average of 36.3 mg S / g lyophilized) were double those obtained for Ascophyilum nodosum (average of 18.14 mg / g).
  • the main polysaccharides in algae are the so-called alginates, formed by polymerization mainly glucuronic acid.
  • the content of alginates was estimated from the uric acid content according to the method proposed in New method for quantitative determination of uronic acids, Blumenkrantz et al., Blumenkrantz, N. and Asboe-Hansen, G. Anal. Biochem, 54, pp. 484-489, 1973.
  • the extract of Bifurcaria bifurcata showed an average content of alginates, expressed as uranic acids and using glucuronic acid as standard, of 55.1 mg / g of lyophilisate, being 15% higher than an extract of Ascophyilum nodosum obtained in the same conditions.
  • the Folin-Ciocalteau method of determining total polyphenols was used, using phloroglucinol as standard.
  • Florotannin chromatographic detection Florotannins are understood to be polymers generated by the polymerization of phloroglucinol (1, 3,5-trihydroxybenzene), in parallel with the name tannins, formed by polymerization of catechin / epicatechin and derivatives. Tannins are components of the cell wall of plants and florotannins are components of macroalgae.

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PCT/ES2014/070288 2013-04-12 2014-04-10 Extracto antioxidante a partir de macroalgas pardas y procedimiento de obtención Ceased WO2014167162A1 (es)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US14/784,203 US20160074317A1 (en) 2013-04-12 2014-04-10 Antioxidant extract from brown macroalgae and method for obtaining same
EP14782293.6A EP2997963A4 (en) 2013-04-12 2014-04-10 ANTIOXIDANE EXTRACT FROM BROWN MACROALGEN AND METHOD FOR OBTAINING THEREOF
CN201480033395.3A CN105377232A (zh) 2013-04-12 2014-04-10 来自褐色巨藻的抗氧化剂萃取物以及其获得方法
JP2016507014A JP2016522171A (ja) 2013-04-12 2014-04-10 大型褐藻類からの抗酸化物質抽出物およびそれを得るための方法
KR1020157032242A KR20150140382A (ko) 2013-04-12 2014-04-10 갈색 거대조류로부터의 산화방지제 추출물 및 그의 수득 방법

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ESP201330523 2013-04-12
ES201330523A ES2441469B2 (es) 2013-04-12 2013-04-12 Extracto antioxidante a partir de macroalgas pardas y procedimiento de obtención

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US (1) US20160074317A1 (enExample)
EP (1) EP2997963A4 (enExample)
JP (1) JP2016522171A (enExample)
KR (1) KR20150140382A (enExample)
CN (1) CN105377232A (enExample)
ES (1) ES2441469B2 (enExample)
WO (1) WO2014167162A1 (enExample)

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FR3158225A1 (fr) 2024-01-16 2025-07-18 Laboratoire Clemascience Compositions nutraceutiques et leur utilisation pour induire une perte de poids corporel et/ou une réduction de l’accumulation de graisse.

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CN106070339B (zh) * 2016-06-08 2019-04-19 北京大学深圳研究生院 具有抑藻活性的褐藻多酚组合物及其制备方法和应用
RU2650808C1 (ru) * 2016-12-09 2018-04-17 Федеральное государственное бюджетное учреждение науки Мурманский морской биологический институт Кольского научного центра Российской академии наук (ММБИ КНЦ РАН) Сухой экстракт из фукусовых водорослей, обладающий антиоксидантным действием, и способ его получения
TWI690323B (zh) * 2017-05-09 2020-04-11 大江生醫股份有限公司 泡葉藻萃取物用於調節基因群組表現之用途
CN108066244A (zh) * 2018-02-02 2018-05-25 广州赛莱拉干细胞科技股份有限公司 一种含褐藻多酚的组合物
CN108186420B (zh) * 2018-02-27 2020-06-30 泉州师范学院 铁钉菜提取物在制备海藻源护肤品中的应用
CN108210375B (zh) * 2018-02-27 2020-02-18 泉州师范学院 一种含有铁钉菜提取物的面膜及其制备方法
CN108309834A (zh) * 2018-04-19 2018-07-24 广州赛莱拉干细胞科技股份有限公司 基于褐藻提取物的护肤组合物
GB2579600B (en) 2018-12-05 2023-07-05 Byotrol Plc Anti-viral composition
CN112493306A (zh) * 2020-12-31 2021-03-16 宜昌顶好奇食品科技有限公司 一种禽肉的解冻方法
FI130788B1 (en) * 2021-05-06 2024-03-19 Origin By Ocean Procedure for processing macroalgae
CN113261676A (zh) * 2021-06-08 2021-08-17 山东海之宝海洋科技有限公司 一种食品添加剂组合物及其制备方法和应用
CN113876640B (zh) * 2021-11-16 2023-10-31 北京青颜博识健康管理有限公司 一种抗糖化海藻来源组合物及其制备方法和在美容产品中的应用
WO2024050647A1 (en) * 2022-09-08 2024-03-14 Seachange Biochemistry Inc. Extraction system and method
EP4590285A1 (en) 2022-09-21 2025-07-30 Bioatlantis Limited Phlorotannins and alpha-fucans to treat type 2 diabetes mellitus
US20250368573A1 (en) 2023-05-25 2025-12-04 Blue Evolution Inc. Ecofriendly biopolymer admixture for cement and concrete applications

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US20080280994A1 (en) * 2004-08-17 2008-11-13 Ocean Nutrition Canda Ltd. Ascophyllum Compositions and Methods
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WO2025153574A1 (fr) 2024-01-16 2025-07-24 Laboratoire Clemascience Compositions nutraceutiques et leur utilisation pour induire une perte de poids corporel et/ou une réduction de l'accumulation de graisse

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US20160074317A1 (en) 2016-03-17
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