WO2007049786A1

WO2007049786A1 - Fat-soluble oil comprising fucoxanthin, process for production of the oil, and process for production of fucoxanthin

Info

Publication number: WO2007049786A1
Application number: PCT/JP2006/321658
Authority: WO
Inventors: Kazuo Miyashita; Masashi Hosokawa; Tokutake Sashima; Takanori Sasaki
Original assignee: National University Corporation Hokkaido University; Marine Tec Kamaishi Inc.
Priority date: 2005-10-28
Filing date: 2006-10-30
Publication date: 2007-05-03
Also published as: JP5076903B2; JPWO2007049786A1

Abstract

[PROBLEMS] To provide a fat-soluble oil comprising fucoxanthin which is extracted with a high yield in an economically advantageous manner, a process for production of the oil, and a process for production of fucoxanthin. [MEANS FOR SOLVING PROBLEMS] A fat-soluble oil almost certainly comprising fucoxanthin can be extracted from a brown alga by performing a first step wherein the brown alga is heat-treated and a second step wherein a fat-soluble oil is extracted from the brown alga heat-treated in the first step with an organic solvent. Fucoxanthin can be purified from a fat-soluble oil readily by developing the fat-soluble oil by silica gel column chromatography, wherein the fat-soluble oil is produced from the heat-treated brown alga and has chlorophyll partially decomposed by immersing the brown alga in hot water.

Description

Specification

Fat-soluble oil containing fucoxanthin, method for producing the same, and method for producing fucoxanthin

Technical field

[0001] The present invention relates to a fat-soluble oil containing fucoxanthin extracted from brown algae, a production method for extracting a fat-soluble oil containing fucoxanthin from brown algae in a high yield, and the obtained fat-soluble oil. The present invention relates to a method for producing fucoxanthin for purifying fucoxanthin.

Background art

[0002] Fucoxanthin contained in fat-soluble oils of brown algae is a kind of carotenoid, and in the latter half of the 1960s, a method for extracting fucoxanthin at the laboratory level using brown algae organic solvent was reported. For example, the content of the disclosure is incorporated herein by reference, and in Non-patent Document 1, it was obtained by extracting 20 kg of dried brown algae from 20 kg of methanol at room temperature for 24 hours. The fat-soluble oil is purified by chromatography to obtain 2 g of fucoxanthin per 5 kg of dried brown algae.

[0003] In addition, non-patent document 2 incorporated in the present specification by reference refers to Non-Patent Document 2 in which 5.7 kg of raw brown algae is dried at 40 ° C for 2 days to 1.2 kg of brown algae. On the other hand, fat-soluble oil is extracted using 4 L of a mixed solution of acetone and methanol (acetone: methanol = 7: 3) to obtain 740 mg of crude purified fucoxanthin (470 mg of purified product).

[0004] As is clear from these academic papers and the academic literature cited therein, fat-soluble oil is extracted using dried or raw brown algal power organic solvent and purified by chromatography. The technique is a known technique.

[0005] In recent years, fucoxanthin contained in this brown algae has an anti-obesity effect (non-patent document 3 whose disclosure is incorporated herein by reference) and is highly effective for cancer cells. It has been found to have the ability to induce apoptosis (the disclosure of which is incorporated herein by reference). Thus, fucoxanthin was found to have extremely high bioactivity, and several production methods were provided. It is.

[0006] Fucoxanthin is not contained in dry seaweed as much as 1%. In general, extraction of fat-soluble oils containing fucoxanthin from brown algae is recommended to improve the extraction efficiency. The above-mentioned known technique of extracting using an organic solvent is used. However, in this method, the brown algae residue after extraction has a green color derived from chlorophyll, and the residual pigment component containing fucoxanthin can be seen. Therefore, it is very difficult to extract fat-soluble oil almost completely by conventional techniques.

[0007] On the other hand, when fat-soluble oil is extracted from raw brown algae using an organic solvent, there is a fact that the color of the brown algae residue after extraction of the fat-soluble oil becomes white. It can be seen that it is almost completely extracted. However, it is impossible to preserve raw brown algae for a long time without freezing and salting. Cryopreservation is not suitable from the viewpoint of supplying fat-soluble oil in brown algae stably and economically. Salted brown algae are not suitable for economical storage compared to dried brown algae due to their increased volume and weight.

[0008] That is, in the production methods reported so far, stable supply of raw materials is difficult, and furthermore, it is very difficult to completely extract fat-soluble oil in brown algae economically. There was a problem.

[0009] As an industrial method for producing fucoxanthin, methods for obtaining fucoxanthin from the purification of an extract obtained using a dry or raw brown algal organic solvent (Patent Documents 1 to 5) have been reported.

[0010] Patent Document 1 incorporated in the present specification discloses a method for producing fucoxanthin as an algal power antioxidant. According to the example described in Patent Document 1, Phyeoductylum tricornatum, which is a kind of diatom, is cultured, and the obtained alga body is treated with an organic solvent such as black mouth form Z methanol (2: 1). Soluble oil is extracted. Dry alga bodies are used for extraction, and no pretreatment is performed to increase extraction efficiency.

[0011] The power of disclosure content by reference In Patent Document 2 incorporated in the present specification, brown algae is an ethanol aqueous solution having a temperature of 0 ° C to 50 ° C and a concentration of 55% to 70%. A method of obtaining fucoxanthin by bringing it into contact with ethanol and extracting it with an aqueous ethanol solution is disclosed. According to the example of Patent Document 2, after 40 kg of salted kombu is desalted, fat-soluble oil (yellow colorant) is extracted with 287 kg of 70% ethanol, and 3 kg per 10 Og of yellow colorant extraction residue. 8 mg of fucoxanthin is obtained (36.5 mg per 100 g of dried comb). The brown algae used are free of salted salt and are not pretreated to increase extraction efficiency.

[0012] Patent Document 3 incorporated in the present specification discloses a method of producing fucoxanthin from brown algae with a reduced water content. According to the production example of Patent Document 3, fat-soluble oil is extracted from 100 g of dry ground powdered wakame using petroleum, and from 18 g of salted wakame, 51 mg of fucoxanthin is obtained from 100 g of dried powdered wakame. . These wakame are pre-treated to increase extraction efficiency!

[0013] The power of disclosure content by reference In Patent Document 4 incorporated in the specification of the present application, the state of raw or dry matter is not questioned (and the shape is not limited) from seaweed to organic solvent. A method for extracting and purifying fucoxanthin is disclosed. In this example of Patent Document 4, 200 g of powdered seaweed ground to a fine powder after drying was refluxed and extracted with 500 mL of 95% ethanol for 1 hour to obtain 80 mg of fucoxanthin (40 mg per 100 g of dried wakame). These seaweeds are not pretreated to increase extraction efficiency.

[0014] The power of disclosure content by reference In Patent Document 5 incorporated in the present specification, a method for purifying fucoxanthin by extracting fat-soluble oil with an organic solvent such as algae plate or filamentous force. Is disclosed. Using an organic solvent in an amount of 1: 1 to 1: 100 from the discoid body, etc. (in the case of ethanol, 0 ° C to 60 ° C, 0.5 hour to 100 hours) The resulting extract strength also purifies fucoxanthin. According to the example of this Patent Document 5, the almond body of Okina Mozuku discoid and Okina Mozuku, Ito Mozuku and Tongan Mozuku are sufficiently washed with water and freeze-dried, and the dry body lg is extracted with lOOmL of ethanol to extract a fat-soluble oil. ing. 11.82, 0.076, 0.002, and 326mg fucos per lyophilized Okina Mozuku disc, Okina Mozuku, Ito Mosque, Nga Mosque lg, respectively Xanthine is obtained (1182, 7.6, 2, and 32.6 mg per lOOg of dry algae, respectively). These algae are not pretreated to increase extraction efficiency.

[0015] The power of disclosure content by reference In Patent Document 6 incorporated in the present specification, raw seaweed power is also extracted from fat-soluble oil using ethanol at a concentration of 80 to 100%, and fucoxanthin is extracted. A method for purification is disclosed. According to the example, 10 g of raw seaweed (water content 90%) was extracted with 80 mL of 100% ethanol at a temperature of 20 ° C and an extraction time of 1 or 3 hours, and the fucoxanthin content was 0.018 mg / mL ( 14 4mg per lOOg of dried wakame. In addition to this, the ability to purify fucoxanthin under various conditions was cited as the most extracted fucoxanthin. In addition to raw wakame, only raw wakame, which has examples of raw kumbu and raw hondawala, are shown. These algae are pre-treated to increase extraction efficiency.

[0016] In the above-described conventional method for producing fucoxanthin from brown algae, problems to be overcome still remain from the viewpoints of the above-described economic efficiency, stable supply, yield, and convenience. .

[0017] Non-Patent Document 1: R. Bonnett, et al., Journal of Chemical Society (C), 1969 (1969) 429-454.

Non-Patent Document 2: J. A. Haugan and S. Liaaen—Jensen, Phytochemistry

28 (1989) 2797-2798.

Non-Patent Document 3: Maeda et al., Biochemical and Biophysical Research Comunications, 332 (2005) 392—397.

Non-Patent Document 4: Hosokawa, BIO INDUSTRY, 21 (2004) 52—57.

Patent Document 1: Japanese Patent Laid-Open No. 7-224278

Patent Document 2: JP-A-9-173012

Patent Document 3: Japanese Patent Laid-Open No. 10-158156

Patent Document 4: JP 2001-335480 A

Patent Document 5: Japanese Unexamined Patent Application Publication No. 2004-35528

Patent Document 6: Japanese Unexamined Patent Application Publication No. 2004-75634

Disclosure of the invention Problems to be solved by the invention

[0018] The present invention has been made in view of the problems of the prior art, and is a fat-soluble oil containing fucoxanthin extracted economically in high yield, a method for producing the same, and a method for producing fucoxanthin. The purpose is to provide.

Means for solving the problem

[0019] As a result of intensive studies on the above problems, the inventors of the present invention have made dried brown algae heat-treated in hot water so as to contain moisture, and the brown algae containing the moisture are treated. As a result, when the fat-soluble oil was extracted using an organic solvent, it was found that the fat-soluble oil containing fucoxanthin was almost completely extracted. In the conventional general recognition, contrary to the fact, fucoxanthin itself is very unstable to heat, and cis-trans isomerism causes thermal decomposition. For this reason, it is considered that most of the fucoxanthin bound in the photosynthetic pigment protein of brown algae is decomposed by hot water heating treatment. Methods for extracting fucoxanthin and purifying fucoxanthin have been described in any non-patent literature such as academic papers and patent literature. However, the present inventors have overturned the conventional common sense and found the fact that the brown algae, particularly fucoxanthin bound in the photosynthetic chromoprotein, hardly decomposes. Furthermore, the present inventors easily purify fucoxanthin by developing this special fat-soluble oil in silica gel column chromatography by decomposing part of chlorophyll by immersing brown algae in hot water. I found out that I can do it.

[0020] The fat-soluble oil containing fucoxanthin of the present invention is obtained by heat-treating brown algae.

[0021] The method for producing a fat-soluble oil containing fucoxanthin according to the present invention includes a first step of heat-treating brown algae, and a fat-soluble oil using an organic solvent from the brown algae heat-treated in the first step. It consists of the 2nd process to extract, It is characterized by the above-mentioned.

[0022] The heat treatment in the first step can be performed in hot water.

[0023] The temperature of the hot water is preferably 50 ° C or higher.

[0024] It is desirable to perform heating in the hot water for 1 minute to 30 minutes.

[0025] The heat treatment in the first step may be a treatment with heated steam. Such treatment with heated steam is also preferably performed for 1 minute or more and 30 minutes or less.

[0026] It is desirable that the water content of the brown algae before the heat treatment in the first step is 50% or less.

[0027] The brown algae are Acinetospora (scientific name: Acinetospora crinita), Tawaragatashimidoro (scientific name: Hincksia mitchellae), Matsumo (scientific name: Analipus Japonicus), Isoiiwatake (scientific name: Ralfsia verrucosa), Yochakuro! Schiff (scientific name: Sphacelaria divaricata), Kashirazaki (scientific name: Halopteris filicina), Yezojahaz (scientific name: Dictyopteris divaric ata), Herayanozu (scientific name: Dictyopteris prolifera), Usnoyanozu (scientific name: Dictyopt eris punctata) : Dictyopteris undulata), Amygusa (scientific name: Dictyota dichotoma), Kazuno Amidji (scientific name: Dictyota divaricata), Itoamiji (scientific name: Dictyota linearis), Fukurinamiji (scientific name: Dilophus okamurae), Futao = (/ child name: distro, seo)ォオキ (scientific name: Labophora vanegata), Sanadagusa ('name: Pachydictyon coriaceum), umyuchi 学 (scientific name: Padina japonica), Ukinachi 学 (scientific name: Padina minor), tsuyu crasum (scientific name: padina minor) Common gussa (Scientific name: S patoglossum pacificum, Shikamikusa e, Shimao Gi (scientific name: Zonaria diesingiana), -Semozuku (scientific name: Acrothrix pacifica), Nagamatsumo (scientific name: Chordaria flageliformis), Okina Mozuku (scientific name: Clodosiphon o kamuranus, scientific name: Papenfussiella kuros otrichia divaricata), ftmozuku (scientific name: Tmocladia crassa), Ίnkke (scientific name: Ishig e okamurae), iroguchi (scientific name: Ishige sinicola), neno limo (scientific name: Leathesia diffo rmis), n ヮ noka ヮ (gi name: Petrospongium rugosum) Mozuku (scientific name: Nemacystus desipiens), Common Nagabukuro (scientific name: Asperococcus bullosus), Iwahige (scientific name: Myelophysus simplex), Hosozobukuro (name: Coilodesme cystoseirae), Ukiyoyomo name: Dictyo siphon foeniculaceu: ^ Punctaria lati folia), foxtail duck (scientific name: Colpomenia phaeodactyla), fukurofunori (scientific name: Col pomenia sinuosa), gakome Li ( 'formic name: hydroclathrus clathratus), Nonono glue (' formic name: Petalonia binghamiae), 7 Yamonori (scientific name: Scytosiphon lomentaria), Ke Berrigusa (scientific name: Cutleria adspersa), Muchimo (scientific name: Cutleia cylindrica), Hiram Chimo (scientific name: Cutleria multifida), Ichimegasa (scientific name: Carpomitra costata), Kyari ('gi name: ¾porochunus radiciformis), Unorengusa (scientific name: ia) a), Tobacco rush (scientific name: Desmarestia tabacoides), Hosobawa turtle (scientific name: Alaria an gusta), Chigaiso (scientific name: Alaria crassifolia), O-Wakame (scientific name: Alaria fistulosa), Ainu turtle (scientific name: Alaria praelonga), huawakame (scientific name) : Undaria petersenia na), Wakame (scientific name: Undaria pinnatifida), Hirome ('gi name: Undaria undarioides), Tsurmo (scientific name: Chorda filum), Amame (scientific name: Agarum clathratum), Nekoashikombu (scientific name: Arthrothamnus bifidus) (Scientific name: Costaria costata), Kajime (scientific name: Ecklonia cava), Kurome (scientific name: Ecklonia kurome), Nonore arame (scientific name: Eckl onia stoloni) fera), arame (scientific name: Eisenia bicyclis), toro kombu (scientific name: Kjellma niella gyrata), gagara kombu (scientific name: Laminaria coriacea), onikombu (scientific name: Laminaria diabolica), macombu ('gi name: Laminaria japonica), nagacomb (' name: Laminaria longissima), Goheikonbu (child name: Laminaria yezonsis), Hinomata (scientific name: Fucus distichus), Yezo shige (scientific name: Silvetia babingtonii), Nebutomok (name: Cystoseria crassipes), Nyolomoku (scientific name: Myagropsis myagens Name: sargassum confusum), Futaemoku ('hand name: Sargassum dupnc atum), Hinki (scientific name: Sargassum fusiformis), Isomok (' child name: sargassum nem iphyllum), Akamoku (scientific name: Sargassum horneri, Sawtoothum macrocar (scientific name: Sargassu m macrocar) ), Togemoku (scientific name: Sargassum micr ac anthum), Cavemog (scientific name: sargassum miyabei), Tamano, Noki Kimoku ('gi name: S argassum muticum, naphtho samo name: sargassum nigrifolium), tamananmog (scientific name: Sargassum ηιρροηι cum), yamatamok (scientific name: Sargassum patens), mametawara (scientific name: Sargassum p iluliferum), ono ヽ mok (scientific name: sargassum ring : Sar gassum siliquastrum), Utofuno (scientific name: Sargassum thunbergu), Yoremoku mod ³ r ('gi name: Sargassum yamamotoi), Endumoku (gi name: Sargassum yendoi), Rappa moku (scientific name: Turbinaria ornata) force At least one kind selected You can do that. [0028] The water content of the brown algae before heat treatment in the first step and extraction of the fat-soluble oil using an organic solvent in the second step is preferably 30% or more.

[0029] The temperature of the brown algae before the heat treatment in the first step and the extraction of the fat-soluble oil using an organic solvent in the second step can be set to 50 ° C or lower.

[0030] The organic solvent may be at least one selected from alcohols, ethers, ketos, aliphatic hydrocarbon halogen compounds, aliphatic hydrocarbons, and aromatic hydrocarbon power. Particularly, alcohols having a carbon number of ~ are preferred.

[0031] The temperature of the organic solvent may be not lower than the melting point of the organic solvent and lower than the boiling point.

[0032] The fucoxanthin content and Z or water-soluble component content can be controlled by the number of extractions with the organic solvent.

[0033] The method for producing fucoxanthin of the present invention comprises using fucoxanthin from a fat-soluble oil containing fucoxanthin obtained by the method for producing a fat-soluble oil containing fucoxanthin of the present invention using chromatography. Isolation 'characterized by purification.

[0034] Further, the method for producing fucoxanthin of the present invention is characterized in that fucoxanthin is isolated and purified from a fat-soluble oil containing fucoxanthin extracted by heat treatment of brown algae using chromatography. .

[0035] Furthermore, the fat-soluble oil containing fucoxanthin of the present invention can be produced by the method for producing a fat-soluble oil containing fucoxanthin of the present invention.

In addition, the fucoxanthin of the present invention can be produced by the method for producing fucoxanthin of the present invention.

In addition, the functional food of the present invention can be obtained by adding the fat-soluble oil containing the fucoxanthin of the present invention or the fucoxanthin of the present invention.

The invention's effect

[0038] The fat-soluble oil containing fucoxanthin of the present invention, a method for producing the same, and a method for producing fucoxanthin can extract a fat-soluble oil containing brown algal power fucoxanthin in a high yield and economically. Became. Furthermore, it has become possible to purify fucoxanthin in a high yield and economically from the obtained fat-soluble oil containing fucoxanthin. [0039] Further, by adding fucoxanthin or a fat-soluble oil containing fucoxanthin to a food material, a functional food having various functions can be produced depending on the application. BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, the best mode for carrying out the present invention will be described in detail with reference to the drawings and tables. The present invention is not limited to this embodiment.

[0041] Fig. 1 is a flowchart of fat-soluble oil extraction and fucoxanthin purification when dry wakame is used as a brown algae, and Fig. 2 is a flowchart of fucoxanthin purification, and the wakame power of brown algae also uses ethanol. A series of operations for extracting fat-soluble oil and isolating fucoxanthin was shown. Here, the term fat-soluble oil means a fat-soluble oil from which brown algae power is extracted in the present invention. Fat-soluble oil extracted from wakame may be referred to as wakame oil, but here wakame belongs to brown algae, so it is fat-soluble oil!

[0042] It is also possible to use an unused part (for example, a part that has been discarded in the past). This wakame was used in the state of being roughly cut as it was without being powdered because of the ease of operation in removing water from the surface of wakame after hot water heating and recovering the extract after extraction with ethanol. However, powdered dried seaweed can shorten the extraction time, so it is desirable to powder it if a large centrifuge can be used.

[0043] As the first step of heat-treating brown algae in the method for producing a fat-soluble oil containing fucoxanthin of the present invention, heating is performed for 1 to 30 minutes in hot water. If it is less than 1 minute, the hot water heat treatment is not effective. On the other hand, if the heating time is 30 minutes or less, heating problems exceeding 30 minutes are not particularly effective, and there are cost problems such as time and utility costs, and decomposition of fucoxanthin, which is an active ingredient, also occurs.

[0044] If the heat treatment time is such a time that chlorophyll is more selectively decomposed without decomposing fucoxanthin, the heat treatment time can be further increased. In addition, when producing fat-soluble oil including chlorophyll, the heat treatment time can be reduced. That is, it is desirable to adjust the heat treatment time according to the target product. [0045] The brown algae in the method for producing a fat-soluble oil containing fucoxanthin of the present invention is heat-treated. In the first step, if the brown algae can contain enough water, the weight ratio of the brown algae to the hot water should be about 1: 15-17. Heat treatment can be performed. However, it is possible to further reduce the weight of hot water, and instead of this hot water heat treatment operation, it is also possible to give water to brown algae by means such as using heated steam.

[0046] It is desirable to adjust the water content of the brown algae after the hot water heat treatment according to the component of the fat-soluble oil for the purpose by removing water on the surface. However, if the water content of brown algae after heat treatment becomes extremely low (less than 10%), the fat-soluble oil will not be extracted at all. Therefore, it is necessary to avoid the water content from becoming extremely low. The water content of the brown algae after treatment is preferably 10% or more, more preferably 30% or more.

[0047] Before the brown algae after the hot water heat treatment in the first step are dried, the second step of extracting the fat-soluble oil using the brown alga power organic solvent after the hot water heat treatment is performed. Start, immerse in an organic solvent such as ethanol, stir the solution, and let stand.

[0048] The solution is filtered, concentrated and dried. This operation can be performed using a rotary evaporator or can be substituted using a freeze dryer. It is possible to obtain a crude fat-soluble oil to be used as a food material by extracting the dried product obtained again with ethanol.

[0049] By repeatedly performing the extraction operation with ethanol in the second step, different fat-soluble oils can be obtained.

[0050] [Example]

Next, examples of the present invention will be described.

In this example, a commercially available dried wakame was used as the brown algae. The commercially available dried seaweed 10 Og was heated in hot water 1.5 to 1.7 L for 15 minutes. The surface of the seaweed after the hot water heat treatment was removed, and as a result, this operation contained 500 g of water (total 600 g) per 100 g of seaweed.

[0051] Before the wakame after the hot water heating treatment in the first step is dried, the second step of extracting the fat-soluble oil from the wakame after the hot water heating treatment using an organic solvent is performed. The solution was started, immersed in _{1 L} of ethanol, stirred for 5 minutes, and allowed to stand for 1 hour. [0052] This solution was filtered, concentrated and dried using a rotary evaporator, and sufficient water was removed from the resulting extracted dried product using nitrogen gas. Add 50 mL of a 2: 1 volume ratio of chloroform: methanol mixed solution to this dried extract and filter the resulting solution. Concentrate and dry again using a rotary evaporator, and again with nitrogen gas. The solvent was removed sufficiently.

[0053] The extraction operation with ethanol in the second step was repeated a total of 4 times to obtain a total of 4 types of fat-soluble oils. In each of these four extraction operations, boiled seaweed was used for the first time, and ethanol extraction residue was immersed in 1 L of ethanol for the second to fourth time, and this solution was stirred for 5 minutes and allowed to stand. . However, in each extraction operation, the first and second standing time was 1 hour. The third settling time was 15 hours and the fourth settling time was 1 day.

[0054] Fig. 3 shows a wakame residue after ethanol extraction of dry wakame power in an example in which the above-described method for producing a fat-soluble oil containing fucoxanthin of the present invention was carried out, and a conventional hot water heating as a comparative example. Shows a photo of wakame residue after ethanol extraction without treatment. As shown in the figure, it can be seen that the appearance of the wakame residue in the example of the present invention is almost white as compared with the conventional example, and the fat-soluble oil containing fucoxanthin (orange) is almost completely extracted. .

[0055] Fig. 4 shows the fat-soluble oil and water-soluble component weight extracted from dried wakame lOOg, and Fig. 5 shows only the weight of the water-soluble component extracted from dried wakame lOOg. As can be seen from FIG. 4 and FIG. 5, the fat-soluble oil was the most during the second extraction. These four types of fat-soluble oils are dissolved in a minimum amount of 30% acetone 'hexane, and then subjected to two rounds of purification and purification by column chromatography, whereby high purity fucoxanthin with a purity of 95% or more is obtained. Obtained. At that time, silica gel was used as the filler, and 30% acetone'-hexane mixed solution was used as the developing solvent.

[0056] FIG. 6 shows the weight of fucoxanthin obtained by purification by column chromatography for four types of fat-soluble oils obtained by repeating the extraction operation of ethanol extraction from dried wakame lOOg four times. Figure 7 shows four fat-soluble oils obtained by repeating the extraction operation of ethanol from dried seaweed lOOg four times, and fucoxan contained in the ethanol extract. The percentage of chin is shown. Figure 8 shows the total weight of fat-soluble oil (excluding fucoxanthin), water-soluble components, and fucoxanthin until the third extraction by repeating the extraction operation of extracting 100 grams of dried seaweed with ethanol three times.

[0057] Fucoxanthin content per 100 g of dried wakame was 85 mg for the first extraction, 79 mg for the second extraction, 41 mg for the third extraction, and 28 mg for the fourth extraction. The percentage of fucoxanthin content in the fat-soluble oil was 5.1% and 6.4% in the first and fourth extracts, respectively, and more than 5%. In the fourth extraction, the ethanol extract itself showed fucoxanthin content close to 4.9% and 5%. In other words, it means that it can be used as a suitable food material by collecting extracts with a specific number of extractions or a collection of them.

[0058] Therefore, the fucoxanthin content and the Z or water-soluble component content can be controlled by the number of extractions with an organic solvent, and furthermore, an extract with a specific number of extractions can be appropriately blended to produce an appropriate fucoxin according to the application. A fat-soluble oil having a xanthine content can be obtained.

[0059] As shown in FIG. 8, a fat-soluble oil containing 205 mg of fucoxanthin could be produced as a material mixed with the third ethanol extract. In other words, in the conventional method, the high purity fucoxanthin obtained when the dried wakame was powdered and extracted with ethanol was about 18 to 144 mg per 100 g of dried wakame. 4 to 5 times higher yield.

Industrial applicability

[0060] The extracted fucoxanthin and the fat-soluble oil containing the extracted fucoxanthin can be used as a functional food material for adding to a food material or the like, and can be used in the field of food. In addition to that, it is possible to consider other uses in the fields of medicine and agriculture.

Brief Description of Drawings

[0061] FIG. 1 is a flowchart showing an embodiment for carrying out the present invention, which is a flowchart of extraction of fat-soluble oil from dried seaweed and purification of fucoxanthin.

FIG. 2 is another flowchart showing a form for carrying out the present invention, and is a flowchart of fucoxanthin purification. (3) Dry wakame strength after carrying out the method for producing a fat-soluble oil containing fucoxanthin according to the embodiment of the present invention and the wakame residue after ethanol extraction, and the dried wakame without the conventional hot water heat treatment as a comparative example Fig. 4 shows a photograph of wakame residue after ethanol extraction. 4) The method for producing a fat-soluble oil containing fucoxanthin of the present invention was used, and the fat-soluble oil and water-soluble oil extracted from 1 OOg of dried wakame. Indicates the weight of the component.

[5] The weight of water-soluble components extracted from ethanol from 100 g of dried seaweed by carrying out the method for producing a fat-soluble oil containing fucoxanthin of the present invention is shown.

圆 6] Indicates the weight of fucoxanthin obtained by purifying the fat-soluble oil extracted from ethanol from 100 g of dried seaweed by carrying out the method for producing a fat-soluble oil containing fucoxanthin of the present invention.

FIG. 7 shows the proportion of fucoxanthin contained in a fat-soluble oil obtained by carrying out the method for producing a fat-soluble oil containing fucoxanthin of the present invention and an ethanol extract.

FIG. 8 shows the weight of the fat-soluble oil, water-soluble component and fucoxanthin until the third extraction by carrying out the method for producing the fat-soluble oil containing fucoxanthin of the present invention.

Claims

The scope of the claims

[1] A fat-soluble oil containing fucoxanthin, which is obtained from heat-treated brown algae.

[2] A fucoxanthin comprising a first step of heat-treating brown algae and a second step of extracting fat-soluble oil from the brown algae heat-treated in the first step using an organic solvent. The manufacturing method of the fat-soluble oil to contain.

[3] The method for producing a fat-soluble oil containing fucoxanthin according to claim 2, wherein the heat treatment in the first step is a heat treatment in hot water.

[4] The method for producing a fat-soluble oil containing fucoxanthin according to claim 3, wherein the temperature of the hot water is 50 ° C or higher.

5. The method for producing a fat-soluble oil containing fucoxanthin according to claim 2, wherein the heat treatment in the first step is treatment with heated steam.

[6] The method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 3 to 5, wherein heating is performed for 1 minute to 30 minutes with the hot water or heated steam.

7. The method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 2 to 5, wherein the water content of the brown algae before heat treatment in the first step is 50% or less.

[8] The brown algae are Acinetospora (scientific name: Acinetospora crinita), Tawaragashimidoro (scientific name: Hincksia mitchellae), Matsumo (scientific name: Analipus Japonicus), Isoiwatake (scientific name: Ralfsia verrucosa), Yochakuro! Schiff (scientific name: Sphacelaria divaricata), Kashirazaki (scientific name: Halopteris filicina), Yezojahaz (scientific name: Dictyopteris divaric ata), Herayanozu (scientific name: Dictyopteris prolifera), Usnoyanozu (scientific name: Dictyopt eris punctata) : Dictyopteris undulata), Amygusa (scientific name: Dictyota dichotoma), Kazuno Amidji (scientific name: Dictyota divaricata), Itoamiji (scientific name: Dictyota linearis), Fukurinamiji (scientific name: Dilophus okamurae), Futao = (/ child name: distro, seo)ォオキ (scientific name: Labophora vanegata), Sanadagusa ('name: Pachydictyon coriaceum), umyuchi 学 (scientific name: Padina japonica), Ukinachi 学 (scientific name: Padina minor), tsuyu crasum (scientific name: padina minor) Common Gusa (scientific name: S patoglossum pacificum), Jigamigusa (scientific name: Stypopodium zonale), Shimaogi (scientific name: Zonaria diesingiana), -Semozuku (scientific name: Acrothrix pacificaj), Nagamatsumo (scientific name: Chordaria flageliformis), Okina mozuku (scientific name: clomura omurasi Papenfussiella kuromo), Ishimosque (scientific name: Sphaer otrichia divaricata), ft mosque (scientific name: Ί moc dia crassa), Ink (scientific name: Isnig e okamurae), Iroguchi (scientific name: Ishige sinicola, Nonorimo ('child name: Leathesia diffo rmis ノ, N ヮノカヮ ('Gi: Petrospongium rugosum ;, Mozuku (' Gema: Nemacystus desipiens), Common Nagabukuro (scientific name: Asperococcus bullosus), Iwahige (scientific name: Myeiopnysus simplex), Hosoezofukuro (scientific name: Coiiodesme cystose) Kiyo-mo ('Name: Dictyo siphon foeniculaceu), Nono-no-mod: ^ (Scientific name: Punctaria lati folia), Hosokubi-Tamo (Scientific name: Colpomenia p haeodactyla), Fukurofunori (scientific name: Col pomenia sinuosa), sword comenori ('gi name: hydroclathrus clathratus), ヽノノノリ (' name: Petalonia binghamiae), 7 monsters (scientific name: Scytosiphon lomentaria), Querberigusa (scientific name: Cutleria adspers) Muchimo (scientific name: Cutleia cylindrica), Hiram Chimo (scientific name: Cutleria multifida), Ichimegasa (scientific name: Carpomitra costata), Kayari ('Ghi name: ¾porochunus radiciformis), Unorengusa (scientific name: Desmarestia ligulat a), Tobacco de mar (scientific name) tabacoides), Hosovakameka (scientific name: Alaria an gusta), Chigaiso (scientific name: Alaria crassifolia), O-wakame (scientific name: Alaria fistulosa), Ainucamame (scientific name: Alaria praelonga), Aowakame (scientific name: Undaria petersenia na), Wakame Scientific name: Undaria pinnatifida), Hirome ('gi name: Undaria undarioides), Turum (scientific name: Chorda filum), Aname (scientific name: Agarum clathratum) Nekoshcomb (scientific name: Arthrothamnus bifidus), Suzime (scientific name: Costaria costata), Kajime (scientific name: Ecklonia kurome), Kurome (scientific name: Ecklonia stolonifera), Arame (cycling name: Eisenia bi Trollo Kombu (scientific name: Kjellma niella gyrata), Gagara Kombu (scientific name: Laminaria coriacea), Oni Kombu (scientific name: Laminaria diabolica), Macombe ('gimin: Laminaria japonica), Nagacomb (' name: Laminaria longissima), Goheikonbu (child: Laminaria yezonsis), Hinomata (scientific name: Fucus distichus), Yezo shige (scientific name: Silvetia babingtonii), Nebutomok ( Scientific name: Cystoseria crassipes), Dioromok (scientific name: Myagropsis myagroides), Funsunmoku ('gi name: sargassum confusum), Fyemog (scientific name: Sargassum duplic a turn ;, Hinnya (scientific name: sargassum fusiformis), Isomok (' sum name: sar hem iphyllum), akamoku ('gis name: Sargassum horneri), saw moss (' hand name: Sargassum m macrocarpum), tokumoku ('child name: sargassum micr ac anthum), cyamoku (scientific name: sargassum miyabei), tamaノヽノヽ = モグ (scientific name: Sargassum muticum), naphtho samo ('gi name: sargassum nigrifolium), tamananmok (scientific name: Sargassum nipponi cum), yamatamok (scientific name: Sargassum patens J, mametawala (scientific name: Sargassum p iluliferum), ォノヽモクScientific name: Sargassum ringgoldianum), Yoremoku (scientific name: Sar gassum siiiquastrum), Umitofuno (scientific name: Sargassum thunbergu no, Yoremokumo 卜 ki (scientific name: Sargassum yamamotoi), End ¹ Nomoku The method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 2 to 7, which is at least one selected from (scientific name: Sargassum yendoi) and trumpet moku (scientific name: Turbinaria ornata).

[9] The heat content in the first step, and the moisture content of the brown algae before extracting the fat-soluble oil using the organic solvent in the second step is 30% or more. The manufacturing method of the fat-soluble oil containing the fucoxanthin as described in any one.

[10] The heat treatment in the first step, and the temperature of the brown algae before extraction of the fat-soluble oil using the organic solvent in the second step is 50 ° C or lower. A method for producing a fat-soluble oil containing fucoxanthin according to 1.

[11] The fuco according to claim 2, wherein the organic solvent is at least one selected from alcohols, ethers, ketos, aliphatic hydrocarbon halogen compounds, aliphatic hydrocarbons, and aromatic hydrocarbon powers. A method for producing a fat-soluble oil containing xanthine.

12. The method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 2 to 11, wherein the temperature of the organic solvent is not lower than the melting point and lower than the boiling point of the organic solvent.

[13] The fucoxanthin according to any one of claims 2 to 12, wherein the fucoxanthin content and Z or water-soluble component content are controlled by the number of extractions with the organic solvent. A method for producing a fat-soluble oil.

[14] A method for producing fucoxanthin, comprising isolating and purifying fucoxanthin from a fat-soluble oil containing fucoxanthin extracted by heat treatment of brown algae using a chromatograph.

[15] From the fat-soluble oil containing fucoxanthin obtained by the method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 2 to 13, fucoxanthin is isolated using chromatography. A method for producing fucoxanthin, which comprises purifying.

[16] A fat-soluble oil containing fucoxanthin obtained by the method for producing a fat-soluble oil containing fucoxanthin according to any one of claims 2 to 13.

[17] Fucoxanthin obtained by the process for producing fucoxanthin according to claim 14 or claim 15.

[18] A functional food comprising the fat-soluble oil containing the fucoxanthin according to claim 1 or 16, or the fucoxanthin according to claim 17.