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WO2008108001A1 - Galactolipide - Google Patents

Galactolipide Download PDF

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Publication number
WO2008108001A1
WO2008108001A1 PCT/JP2007/054598 JP2007054598W WO2008108001A1 WO 2008108001 A1 WO2008108001 A1 WO 2008108001A1 JP 2007054598 W JP2007054598 W JP 2007054598W WO 2008108001 A1 WO2008108001 A1 WO 2008108001A1
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WO
WIPO (PCT)
Prior art keywords
acyl chain
acid acyl
acid
chain
eicosenoic
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
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PCT/JP2007/054598
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English (en)
Japanese (ja)
Inventor
Assunta Napolitano
Virginia Carbone
Paola Saggese
Cosimo Pizza
Kinya Takagaki
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Toyo Shinyaku Co Ltd
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Toyo Shinyaku Co Ltd
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.)
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Priority to PCT/JP2007/054598 priority Critical patent/WO2008108001A1/fr
Priority to JP2009502416A priority patent/JPWO2008108001A1/ja
Publication of WO2008108001A1 publication Critical patent/WO2008108001A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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

Definitions

  • the present invention relates to galatatolipid. More specifically, monogalactosyldiacylglycerol (MG D G) and digalactosyldiacylglycerol
  • Ipomoea batatas L. (Satsumaimo) is a tuberous perennial plant grown in many countries whose edible roots are eaten raw or after being cooked in various ways.
  • Sweet potato leaves are an excellent source of biologically active anthocyanin and polyphenol components. 15 different anthocyanin compounds and 6 different polyphenol compounds were identified and quantified. Recent studies on the nutritive composition and physiological functions of sweet potato leaves when used in vegetables, tea, strawberries, bread, and confections have shown that they provide a beneficial food supply for beneficial polyphenolic compounds. Suggested that it could be a source. In addition, they are rich in vitamin B, iron, calcium, sub- and protein.
  • glycolipid structure determination an analytical approach based on mass spectrometry is used to determine the structure of the fatty acid acyl group of the glyce mouth glycolipid.
  • GG Orgambide et al. Lipids, 28th, 1993, p. 975
  • Fatty acids were identified by comparing retention times and mass spectra.
  • Another analytical strategy is to compare the collision-dissociation (CID) spectrum pattern of the carpoxy ion (RC00—) generated by negative ion fast atom bombardment mass spectrometry (FAB / MS) of glyce mouth lipids with that of the standard product.
  • CID collision-dissociation
  • RC00— carpoxy ion
  • FAB / MS negative ion fast atom bombardment mass spectrometry
  • MG DG monogalactosyldiacylglycerol
  • DGDG digalatatosyldiacylglycerol
  • Galactosylglycerols such as MG D G and D G D G are also noted for their bioactivity. For example, it is known to have anti-inflammatory properties (from A. Bruno et al., Eur. J. phar macol., 524, 2005, p. 159) and to inhibit carcinogenesis. Disclosure of the invention
  • the present inventors have discovered several novel galactolipids, monogalactosyl diacylglycerol (MG D G) and digalactosyl diacyl glycerol (D G D G) compounds from fractions of the low polar fraction of sweet potato leaves.
  • MG D G monogalactosyl diacylglycerol
  • D G D G digalactosyl diacyl glycerol
  • the present invention provides a monogalactosyldiacylglycerol compound or a derivative thereof having the following structural formula (I):
  • R 2 is a linolenic acid acyl chain
  • R 2 is 9, 12-nonadecadienoic acid Is it a chain?
  • R 1 is a 9, 12-nonadecamate asil chain and R 2 is an ⁇ -linolenic acid asil chain;
  • R an arachidate chain and R 2 is an oleate chain
  • Ri is an arachidic acid acyl chain and R 2 is a linoleic acid acyl chain;
  • R 2 is a linoleic acid acyl chain
  • R 1 ⁇ is an 11-eicosenoic acid acyl chain and R 2 is an ⁇ -linolenic acid acyl chain;
  • R 2 is a 9, 12-nonadecadienic acid chain
  • R 2 is an 11-eicosenoic acid chain
  • Shaye is a heneicosanoic acid acyl chain
  • R 2 is an ⁇ -linolenic acid acyl chain.
  • the present invention also provides a digalactosyldiacylglycerol compound or derivative thereof having the following structural formula (I I):
  • R 2 is an ⁇ -linolenic acid acyl chain
  • R 1 ⁇ is an 11-eicosenoic acid acyl chain and R 2 is an ⁇ -linolenic acid acyl chain;
  • R 2 is a 9, 12-nonadecadienic acid acyl chain
  • R 1 ⁇ is the 11-eicosenoic acid chain
  • R 2 is the 11-eicosenoic acid chain
  • the present invention also provides a food containing at least one selected from the above-mentioned monogalactosyldiacylglycose oral compounds or derivatives thereof. Also provided is a food containing at least one selected from the group consisting of the above-mentioned digalatatosyldiacylglycerol compounds or derivatives thereof.
  • the food further contains at least one selected from the group consisting of wheat leaf and kale.
  • the food further contains at least one selected from the group consisting of indigestible dextrin, oligosaccharide, and lactic acid bacteria.
  • the present invention also provides a method for producing the monogalactosyldiacylglycerol compound or derivative thereof, the method comprising:
  • the present invention also provides a method for producing the above-mentioned digalatatosyldiacylglycerol compound or a derivative thereof,
  • Galatatolipid is a kind of glyce mouth lipid.
  • Galatatolipids include monogalactosyl diacyl glycerol (MG D G) and digalactosyl diacyl glycerol (D G D G).
  • MG D G monogalactosyl diacyl glycerol
  • D G D G digalactosyl diacyl glycerol
  • MG DG has a structure in which two fatty acid acyl groups are bound to the sn-1 and sn-2 positions of the glycerol skeleton, and one galactose is ether-linked to the sn-3 position of glycerol mouth. Have.
  • D G D G has a structure in which two fatty acid acyl groups are bonded to the sn-1 and sn-2 positions of the glycerol skeleton, and two galactoses are bonded to the glycerol sn 3 position.
  • galactolipid refers to both MG D G and D GD G.
  • the present invention provides novel galagtolipids as described below.
  • the present invention provides a monogalactosyl diacylglycose oral compound or derivative thereof having the following structural formula (I): here,
  • R 2 is an ⁇ -linolenic acid acyl chain
  • R 2 is an ⁇ -linolenic acid acyl chain
  • R i is an arachidic acid acyl chain and R 2 is an oleic acid acyl chain;
  • R an arachidate acyl chain and R 2 is a linoleic acid acyl chain;
  • R 2 is a linoleic acid acyl chain
  • R 1 an 11-eicosenoic acid chain and R 2 is a 9, 12-nonadecaic acid chain;
  • R 1 ⁇ is an 11-eicosenoic acid chain and R 2 is an 11-eicosenoic acid chain;
  • the present invention also provides a digalactosyldiacylglycerol compound having the following structural formula (II) or a derivative thereof:
  • R 1 a palmitate palmitate and R 2 is a 9, 12-nonadecamate chain;
  • R 2 is an ⁇ -linolenic acid acyl chain
  • Is 11-eicosenoic acid acyl chain and R 2 is ⁇ -linolenic acid asinole chain;
  • R 2 is a 9, 12-nonadecadienic acid acyl chain
  • R 1 is an 11-eicosenoic acid chain and R 2 is an 11-eicosenoic acid chain.
  • Examples of the fatty acid of the acyl chain in the galactolipid of the present invention include the following: palmitic acid (C16: 0); stearic acid (C18: 0); oleic acid (C18: ln-9); linoleic acid (C18: 2 6-6); ⁇ -linolenic acid (C18: 3 n-3); Nona Decadienoic acid (C19: 2), especially with double bonds at 9 and 12 positions; arachidic acid (C20: 0); 11-eicosenoic acid (C20: l n-9); and heneicosanoic acid (C2l: 0) )
  • the double bond can be cis or trans.
  • Linoleic acid and ⁇ -linolenic acid usually have a cis-type double bond. In nonadecadienoic acid or 11'-eicosenoic acid, the double bond can be cis or trans.
  • the galatatolipid of the present invention can be produced from sweet potato leaves.
  • the variety of sweet potato is not particularly limited.
  • potato shoots of varieties such as Joy White, Koganesengan, Shiku Yutaka, Sweet Mustache, Ayamurasaki, and Suio can be used.
  • the sweet potato leaves used in the present invention are preferably shoot leaves appearing on the ground when sweet potatoes are cultivated.
  • the leaves of shoots grown from the ground are preferably grown to 10 cm or more, more preferably 30 cm or more, more preferably 60 cm or more. Further, when the length from the position where the stem of the sweet potato goes out from the ground to the tip is measured, the length is preferably within 300 cm, more preferably within 200 cm, further Preferably, shoot leaves that are within 150 cm are used. If it exceeds 300 cm, the tip of the shoot will touch the ground, making it more susceptible to harmful insects and the like, and a sufficient amount of leaves may not be obtained.
  • shoots in a green state that is, young leaves of sweet potato shoots.
  • young shoots of sweet potato shoots refers to leaves within 60 cm from the tip of the sweet potato shoots.
  • the sweet potato leaves as described above may be subjected to processing described later, preferably after washing adhering mud or the like with water.
  • Heat treatment is used to stabilize the quality by deactivating enzymes in the sweet potato leaves, and The purpose is to prevent the curiosity of the clover leaves.
  • Examples of the heat treatment include branching treatment (for example, blanching), dry heat treatment, microwave treatment, infrared ray or far-infrared treatment, steam treatment, and the like. Of these heat treatments, blanching treatment is preferably used.
  • each treatment may be performed after cutting the sweet potato leaves into a major axis of about 10 to 30 cm as necessary.
  • the planting treatment may be carried out by a method commonly used by those skilled in the art so that the color of the sweet potato leaves, that is, the color of chlorophyll, which is the color of the green plant, does not fade.
  • An example of such a blanching process is boiling.
  • the optimum conditions for blanching treatment vary greatly depending on the plant used. In some cases, the blanching process may damage flavor and nutrients and deactivate the physiological activity of useful ingredients. Therefore, in the present invention, the pH is preferably 5.4 or more, more preferably 5.6 to 8.4, more preferably 5.6 to 8.0, and most preferably 5.6 to 7.6. Blanching with hot water. By such branching treatment, it is possible to efficiently obtain sweet potato leaves having high activity such as antioxidant activity and high content of components such as polyphenol.
  • salt is added in an amount of 0.1 to 5 mass per hot water in order to improve the flavor. It is preferable to add at a ratio of / 0 , preferably 0.2 to 3% by mass.
  • pH adjustment treatments When performing dry heat treatment, microwave treatment, infrared or far-infrared treatment, and water vapor treatment, perform these pH adjustment treatments such as spraying a solution adjusted for pH on sweet potato leaves. It is preferable to carry out the treatment.
  • the pH adjustment process is performed by a method commonly used by those skilled in the art. For example, when adjusting to basic conditions, sodium hydroxide, baking soda, calcium carbonate (egg shell calcium , Scallop shell calcium, coral calcium, etc.), and calcium oxide obtained by firing these calcium carbonates can be used for treatment. Further, alkaline ionized water or the like may be used.
  • a solution of an organic acid such as acetic acid, citrate, ascorbic acid, tartaric acid, malic acid or fumaric acid may be used.
  • the amount of these pH adjusting agents may be adjusted appropriately according to the adjusting agent used.
  • the heating temperature in the heat treatment is higher than 80 ° C., preferably 90 ° C. or higher.
  • the heating time is 5 minutes or less, preferably 3 minutes or less, and most preferably 10 seconds to 3 minutes.
  • Cooling can be done by methods commonly used by those skilled in the art, such as immersing the potato leaves after heat treatment in cooling water or quenching them with cold air.
  • immersing the potato leaves after heat treatment in cooling water or quenching them with cold air.
  • water of 30 ° C. or lower preferably water of 2 ° C. or lower is used.
  • the lower the cooling temperature the brighter the sweet potato leaves are and the more beautiful they look.
  • the cooling time is an arbitrary time according to the processing amount of the sweet potato leaves, but it is preferable to carry out the cooling until the sweet potato leaves themselves reach a temperature equal to the cooling temperature.
  • Drying is preferably used because the quality of the sweet potato leaves before processing can be maintained. Drying is performed using any drying method commonly used by those skilled in the art. Drying is performed using a dryer according to the drying method, for example, a hot air dryer, a high-pressure steam dryer, an electromagnetic wave dryer, a direct-fired heater, a rotary draft dryer, a freeze dryer, or a vacuum concentrator. Done. Of these, hot air dryers, direct-fired dryers, and rotary draft dryers are preferable from the viewpoint of cost and drying efficiency.
  • Drying is preferably performed so that the moisture content in the dried product is 5% by mass or less.
  • the drying treatment is performed at a temperature of about 60 to 1550 ° C. under normal pressure, so that a sweet and colorful dried powder of sweet potato leaves can be obtained. 6 0 under reduced pressure. If it is performed at a temperature below C, preferably above the temperature at which sweet potato leaves freeze and below 60 ° C., drying can be performed while reducing the loss of nutrient components. ''
  • the two-stage drying can be performed using, for example, a hot air dryer.
  • primary drying is performed at a temperature of 60 to 80 ° C. until the water content becomes 25 mass% or less.
  • secondary drying is performed at a temperature higher than the primary drying until the moisture content of the primary dried potato leaves is 5% by mass or less.
  • the temperature of secondary drying is preferably 70 to 90 ° C, and more preferably around 80 ° C to obtain a sweet potato leaf powder having a high polyphenol content and a bright color. Can do.
  • the temperature difference between primary drying and secondary drying is preferably about 5 to 15 ° C, and more preferably about 10 ° C.
  • the temperature of the subsequent drying is preferably 75 to 85 ° C., more preferably about 80 ° C.
  • the drying time is shortened and the green sweet flavor of sweet potato leaves is maintained.
  • the temperature difference within a certain range as described above, water management of the green leaves in the drying process is facilitated and drying is performed efficiently.
  • the potato leaves dried in this manner may be further powdered to obtain a dry powder.
  • hot air dryer, direct-fired heater, and rotary type A ventilation dryer is preferably used.
  • the dried powder of sweet potato leaves may be further pulverized to further reduce the particle size. Since sweet potato leaves have different parts from the stem, leaf and petiole, it is preferable to go through a coarse pulverization step or a fine pulverization step from the viewpoint of increasing the pulverization efficiency.
  • Coarse rice cake 0 The process of cutting the dried green potato leaves with any machine or apparatus known to those skilled in the art such as cutter, slicer, dicer and the like.
  • the major axis is preferably 2 O mm or less, more preferably 0.1 to L O mm.
  • the fine pulverization step is a step of finely pulverizing the coarsely pulverized potato leaves to obtain fine pulverized powder.
  • 90% by mass is finely pulverized so that it passes through the 200 mesh section.
  • the fine pulverization is performed by using a machine or an apparatus normally used by those skilled in the art, such as a crusher, a mill, a blender, and a stone mill.
  • heat sterilization it is performed before the fine powder mashing process.
  • the coarsely ground sweet potato leaves can be uniformly heated, the flavor of the green leaves can be improved, and efficient sterilization can be performed. This heat treatment is performed at 110 ° C.
  • a high-pressure sterilizer for example, a heat sterilizer, a pressure steam sterilizer, or the like
  • a high-pressure sterilizer for example, a heat sterilizer, a pressure steam sterilizer, or the like
  • coarsely ground sweet potato leaves are, for example, saturated with steam at 110 to 200 ° C under pressure of 0.5 to 10 kg / cm 2 , Heat sterilization treatment for 2 to 10 seconds. If necessary, the moisture contained during heating with saturated water steam is further dried.
  • the texture is improved by finely kneading, and preferably, the texture is further improved by sequentially performing the steps of coarse pulverization, heat treatment, and fine pulverization. It becomes easy to mix.
  • the dried potato leaves may be prepared by coarsely mashing the potato leaves before the drying treatment into fine pieces or pastes, and then performing the above drying treatment. Ie powdering
  • the treatment may be performed using dried potato leaves, or may be performed using undried (eg, fresh leaves, boiled potato leaves, etc.) potato leaves.
  • a vacuum concentrator is preferable in terms of production cost and drying efficiency.
  • the extract of sweet potato leaves when used as an extract powder, it may be pulverized using a spray dryer such as a spray dryer.
  • a spray dryer When a spray dryer is used, excipients such as dextrin, cyclodextrin, starch, and maltose are added as necessary to increase the recovery rate.
  • dextrin is used.
  • the mass ratio of squeezed to dextrin is preferably 1:10 to 5: 1.
  • the drying to obtain the extract powder is preferably performed so that the water content in the extract powder is 5% by mass or less.
  • the pressing process is performed using, for example, a pressing machine.
  • a pressing machine As a result, the juice of sweet potato leaves is obtained.
  • the term “sweet potato leaf” includes not only fresh leaves but also potato leaves that have been processed as described in (1) to (3) above.
  • the galactolipid of the present invention is obtained by transferring methanol extract of the above sweet potato leaves, methanol, water, Z-acetonitrile, as described in the following examples, for example. It can be separated and recovered by subjecting it to a solid phase extraction method used as a phase.
  • the following examples detail the procedure for separating galactolipids of the present invention, but the method for obtaining galactolipids of the present invention is not limited thereto.
  • a method for producing the galactolipid or derivative thereof of the present invention which comprises (1) a step of subjecting sweet potato leaves to methanol extraction, (2) a step of separating a low polarity fraction by solid phase extraction, and (3) Includes a step of separation using high performance liquid chromatography.
  • the extraction process is performed by adding methanol (including water-containing methanol) to sweet potato leaves (raw leaves, dry powder, extract powder, etc.).
  • the low polarity fraction can be obtained by, for example, extracting the above extract from a C-18 sep-pak cartridge (Waters
  • the cartridge can be preconditioned with methanol, water, and 0.2% formic acid, washed with 0.2% formic acid and 0.2% formic acid / methanol (50:50, v / v), and then the low polarity fraction. Can be eluted with methanol.
  • the eluted low polar fraction can be separated by mobile phase (elution method A) of methanol Z water / acetonitrile (90.5: 7: 2.5), for example.
  • the mobile phase of methanolic water Z-acetonitrile (82: 5: 15: 2.5) (elution method)
  • the galactolipids collected from the sweet potato leaves can be used as needed by synthetic adsorbents (Diaion HP 20, Sephabies SP 8 25, Amberlite XAD4, MC Ige 1 CHP 20 P, etc.), dextran. It may be purified by a method usually used by those skilled in the art using a resin (such as CEFADEX LH-20).
  • the galatatolipid of the present invention may be in the form of a derivative. Any derivative that can be found in the naturally occurring form, for example, derivatives in which the alcoholic 0H of the galactose residue is substituted with various substituents, and food or pharmaceutically acceptable Any derivative that is capable can be included.
  • the galactolipid or derivative thereof of the present invention can be used for pharmaceuticals, foods and beverages, and cosmetics based on its biological activity.
  • the biological activity include an antitumor action, an anti-inflammatory action, and an antioxidant action.
  • the galagtolipid of the present invention can be used for the production of functional foods and supplements having anticholesterol action, blood flow improvement action and the like, and cosmetics having skin quality improvement effect, beauty effect and moisturizing effect. It can be used with ingredients such as food ingredients, pharmaceutical ingredients, excipients, extenders, binders, thickeners, emulsifiers, colorants, fragrances, or seasonings.
  • the galatatolipid or derivative thereof of the present invention can be incorporated into foods as described below.
  • Lactic acid bacteria especially lactic acid bacteria with high intestinal reach efficiency, for example, spore-forming lactic acid bacteria, lactic acid bacteria prepared by coating enteric substances, etc., specific strains with high intestinal reach Lactic acid bacteria, Bifidobacterium longam, Lactobacillus casei, Lactobacillus acidophilus, Rata topaticilus' Helveticas, Rata tobacillus delpureiki, Streptococcus thermobirarus, etc.) obtain.
  • Lactic acid bacteria especially lactic acid bacteria with high intestinal reach efficiency, for example, spore-forming lactic acid bacteria, lactic acid bacteria prepared by coating enteric substances, etc., specific strains with high intestinal reach Lactic acid bacteria, Bifidobacterium longam, Lactobacillus casei, Lactobacillus acidophilus, Rata topaticilus' Helveticas, Rata tobacillus delpureiki, Streptococcus thermobirarus, etc.
  • the food in powder form can be dispersed in water or the like and used as a green juice form.
  • it can be mixed with green leaves such as wheat leaves, kale, tomorrow leaves, and mulberry leaves, which are conventional green juice ingredients, preferably wheat powder or kale powder.
  • the food can also be in the form of beverages such as plant fermented juice, vegetable juice (eg carrot juice), plant extract, fruit juice and the like. Indigestible dextrins, oligosaccharides, and materials such as lactic acid bacteria can also be suitably incorporated into foods.
  • Foods are processed into forms such as granules, tablets, capsules (hard capsules, soft capsules, etc.), pills, powders, liquids, tea bags, and baskets, depending on the application.
  • Such processed foods can be eaten as they are, or they can be dissolved in water, hot water or milk. If powder or the like is provided in the form of a tea bag, the extract obtained by soaking in hot water can be used as a beverage.
  • Methanol for HPLC was purchased from: [. T. Baker (Baker Mallinckrodt, Phillipsburg, NJ, USA). Acetonitrinore (ACN) and formic acid were obtained from Carlo Erba (Milan, Italy). HPLC water (18 mQ) was prepared using a Millipore Milli-Q water purifier (Millipore Corp., Bedford, MA, USA). 1. 2. Sample preparation
  • a sample (3 g) of air-dried sweet potato leaves was extracted with 60 mM MeOH at room temperature for 8 days. The extract was filtered to give a yield of 313.13 mg.
  • the methanol extract was passed through a C-18 sep-pak cartridge (Waters Corporation, Milford, Massachusetts, USA). The cartridge was preconditioned with methanol, water, and 0.2% formic acid. After washing with 0.2% formic acid and 0.2% formic acid / methanol (50:50, v / v), the low polar components were eluted with methanol and used for chromatographic analysis.
  • a mobile phase of methanolic water Z-acetonitrile (82.5: 15: 2.5) was also used to improve the separation of the more polar galactolipids.
  • the eluate is injected directly into the electrospray ion source, and MS1 and MS / MS spectra are obtained in positive ion mode, using software provided by the manufacturer (Waters Mass Lynx 4.0 software). Elucidated using.
  • the desolvation and source temperatures were 180 ° C and 100 ° C, respectively.
  • the operating conditions optimized for the detection of galactolipids were as follows: Kybilly voltage 3400V, sample cone voltage 40V, extraction voltage 1.5V, impact cell voltage 7V.
  • MS / MS spectra were obtained in measurement scan mode using impact energy in the range of 30-45V. MS / MS spectra were recorded in the 50-1500 m / z region.
  • the galactolipid separated by HPLC was exposed to 2.5 ml of a methanol solution containing 2% sulfuric acid at 80 ° C. for 4 hours and subjected to a transesterification reaction. After completion of the reaction, the reaction tube was cooled. Then, 2.0 ml of water and 1.0 ml of hexane were added to each reaction tube, sealed, and mixed by vortexing for 10 minutes. The reaction tube to promote centrifuged to phase separate for 1 minute at 4000 r P m, and; ⁇ transferred hexane phases in GC measurement vials. To the remaining aqueous phase was added 1.0 ml of hexane and extraction was performed as described above. This process Repeated twice.
  • the initial oven temperature is 40 ° C (5 minutes), programmed to increase to 60 ° C at 4 ° C / minute, then 15 to 150 ° C at Z minutes, and 280 ° at 3 ° C / minute C was heated to 300 ° C in 20 ° CZ minutes.
  • the total execution time was 60 minutes.
  • Helium was a carrier gas and l ml / min was a column flow.
  • Mass spectrometry was performed at 70 eV ionization energy and a 50 ⁇ 500 mass range was analyzed with a scan time of 0.5 seconds.
  • the combined analysis of NMR and a selective one-dimensional T0CSY (total correlation spectroscopy) vector identified the presence of one unit of ⁇ -D-galactoviranosyl.
  • the j3 -glycosidation to glycerol shows that the anomeric carbon (C1, position) has a low magnetic field shift ( ⁇ 105) and the proton (HI, position) has a high magnetic field shift ( ⁇ 4 26), it was confirmed that the coupling constant of 3 JHI- -H2- was very large (J> 7Hz).
  • the coupling constant of 3 J H2 , _ H3 is large (J> 9 Hz), and the coupling constant of the H4 and protons in the sugar part is small ( ⁇ 3.86, J ⁇ 3Hz), the constituent sugar was found to be galactose.
  • the HSQC Heteronuclear Single Qua ntum Correlation: By examining the spectrum, it was found that the sugar part consists of disaccharides.
  • HMBC Heteronuclear Multiple Bond Correlation
  • fatty acid composition of each galactolipid could be determined.
  • C19 2 Nonadecadienoic acid;
  • C21: 0 one or two fatty acids in heneicosanoic acid may be present as fatty acids in galactolipids I understood, but could not determine the three-dimensional structure.
  • the acid strength of the elution solvent also affected the fragmentation pattern of the MS / MS spectrum.
  • the LC-ESI / MS / MS data measured for MG DG compounds under acidic conditions show that fragmentation with [M + H-162] + ion formation occurs in addition to the fragment ions generated by cleavage of the galactose moiety. It showed that it was detected.
  • the DGDG compound Since the DGDG compound has two galactosyl units, its MS / MS spectrum was derived from the [M + H-162] + MG DG ion derivative by the disappearance of the second sugar (ie, the outer sugar) Product fragment ions were also detectable.
  • the determination of the degree of unsaturation of fatty acids and the position of double bonds in the galactolipid chain was accomplished by analyzing the high molecular weight region of the MS / MS spectrum.
  • oleic acid C18: ln-9 cis
  • linoleic acid C18: 2 n-6 cis
  • ⁇ -linolenic acid CI 8 : 3 ⁇ -3 cis
  • nonadecadienoic acid CI 9 : 2
  • Arachidic acid C20: 0
  • 11-eicosenoic acid C20: l n-9 cis
  • heneicosanoic acid C21: 0).
  • the MS / MS spectrum is an MGDG and DGDG upper series with a large number of C (i.e. at least one of the two carbons of the glycerol skeleton is C20: 0, C20: l, and C21: 0 (With some fatty acids attached) produced a more complex spectrum, especially in the high molecular weight region, and a variety of strong fragment ions in addition to the fragments already described.
  • Figure 1 shows the LC-ESI / MS / MS spectrum of compound (11).
  • A is the overall spectrum
  • (b) is the high molecular weight region
  • (c) is the low molecular weight region.
  • two fragment ion peaks at m / z 519.6 and 551.5 were prominently detected. These were thought to be the result of the disappearance of the two fatty acids, icosenoic acid (C20: 1) and linolenic acid (C18: 3), respectively, thereby determining the fatty acid composition.
  • the binding position of each fatty acid acyl chain in the MGDG molecule was determined by the relative intensity of [M + Na-R x C0 2 H] + ions. Specifically, eicosenoic acid (20: 1) at sn-1 and linolene at sn-2 It was confirmed that the fatty acid chain of acid (18: 3) was present.
  • the low molecular weight region shows fragment ions associated with the sugar moiety.
  • the explanation is given below with reference to Fig. 1 (c). Cleavage of the glycosidic bond yields fragment ion peaks at m / z 185.1 and m / z 203.1, which are the hydroxyl groups removed from the sugar ring (m / z 185.1) (M / z 203. 1), and it was determined that the ions were added by sodium.
  • the fragment ion peak at m / z 243.2 is the cleavage of two neutral fatty acids simultaneously from the galactosylglycerol skeleton.
  • the sodium-bound ions of m / z 301.3 and 315.3 were formed by the disappearance of one fatty acid and the elimination of a part of the acyl chain of the other fatty acid. This detachment occurred in the part of the other fatty acid in the chain of the acyl chain up to two or three positions away from the carbon.
  • the fragment ion at m / z 755.8 is C 3 H 4 of the sn-2 fatty acid acyl group and CH 4 of the sn-1 fatty acid acyl group. It could be formed by either the disappearance of each, or the disappearance of two C 2 H 4 in both acyl chains.
  • the MS / MS spectrum in the molecular weight range of 771.8.—551.5 was analyzed.
  • the double bond of the sn-2 acyl group is located at the 9th and 12th carbons, and that the double bond of the sn-1 acyl group is located at the 1st carbon.
  • the former was confirmed to be 9, 12, 15-octadecatrynoic acid, and the latter was found to be due to 11-eicosenoic acid.
  • Figure 2 shows the LC-ESI / MS / MS spectrum of compound (24).
  • (A) is the overall spectrum
  • (b) is the high molecular weight region
  • (c) is the low molecular weight region.
  • the MS / MS spectrum (FIG. 2) showed a fragmentation pattern very similar to the MGDG molecule of compound 11 of Example 1 above.
  • FIG. 3 shows the MS / MS spectrum of compound (7).
  • A is the overall spectrum
  • (b) is the high molecular weight region.
  • the MS / MS spectrum showed two strong ions at m / z 519.5 and 535.5. These correspond to [M + Na- personally1]. + Fragment ion and [M + Na-R 2 C0 2 H] + fragment ion.
  • the high molecular weight region of the spectrum (Fig. 3 (b)) shows the two generated fragment ions of m / z 651.8 and 633.8 with [M + Na-162] + opium [M + Na-180] + respectively.
  • the presence of in the low molecular weight region of the spectrum, [R 2 C0] + fragment ions and [R 2 C0 + 74] + Fragment of m / z 26 1.3 and 35.4
  • the fragment ion peaks already described at m / z 185.1 and 203.2 were seen with the dopant ions.
  • the position of the double bond in the chain was determined by analyzing the fragmentation pattern of the high molecular weight region of the spectrum.
  • R 2 represent a fatty acid acyl group bonded to the sn-1 position and a fatty acid acyl group bonded to the sn-2 position, respectively.
  • the notation of fatty acid acyl groups follows the notation used when discussing biosynthesis. The position of the double bond is described with a number from the side opposite to the carbonyl group. For example, the linolenic acid has cis double bonds at the 9th, 12th, and 15th positions. : 3 n-6 cis ".
  • the obtained sweet potato leaves were cut to about 5 mm and immersed in 2 L hot water (90 ° C) adjusted to pH 8.0 for 1 minute. Next, it was cooled with water at 25 ° C, and the cooled sweet potato leaves were centrifuged for 30 seconds to be dehydrated to some extent. After dehydration, dry with warm air (primary drying) for 2 hours at 70 ° C in a dryer until the water content reaches about 20% by mass, and further at 80 ° C so that the final water content becomes 3% by mass. Hot air drying (secondary drying) was performed for 4 hours. Next, steam sterilization was performed using saturated steam at 150 ° C for 3 seconds. Next, the water contained in the sweet potato leaves is dried by warm air drying, and then finely ground using a hammer mill so that 90% by mass passes through the 200 mesh section, and the dry powder of sweet potato leaves (80 g) is added. Obtained.
  • foods (tablets; 2.00 mg / tablet) can be produced in the following amounts. ⁇
  • a food (granule) is produced with the following blending amount.
  • Example 8 Using the dry powder and indigestible dextrin of Example 5 above, a food can be produced. (Example 8)
  • a food can be produced using the dry powder and oligosaccharide of Example 5 above.
  • a food can be produced using the dry powder and lactic acid bacteria of Example 5 above.
  • the galatatolipid of the present invention can be used in pharmaceuticals, foods and beverages, and cosmetics.
  • the biological activity include an antitumor action, an anti-inflammatory action, and an antioxidant action.
  • Galatatolipids of the present invention are functional foods, supplements, and skin quality improving effects, cosmetic effects, and moisturizing effects that have anti-cholesterol effects, blood flow improving effects, etc. It can be used for the production of cosmetics with fruits.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
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  • Food Science & Technology (AREA)
  • Mycology (AREA)
  • Crystallography & Structural Chemistry (AREA)
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  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Saccharide Compounds (AREA)

Abstract

L'invention porte sur un nouveau composé monogalactosyldiacylglycérol ou digalactosyldiacylglycérol ou un dérivé de ceux-ci ; sur un procédé de fabrication du composé ou du dérivé ; et sur un aliment contenant le composé.
PCT/JP2007/054598 2007-03-02 2007-03-02 Galactolipide Ceased WO2008108001A1 (fr)

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JP2012025706A (ja) * 2010-07-26 2012-02-09 National Institute Of Advanced Industrial Science & Technology 抗酸化剤及びその利用
CN102905543A (zh) * 2010-05-25 2013-01-30 雀巢产品技术援助有限公司 协同抗氧化剂组合物
BE1021587B1 (fr) * 2013-08-30 2015-12-16 S.A. Laboratoires Pharmaceutiques Trenker Composition pour le soin de la peau et son procede de preparation
JP2016056178A (ja) * 2015-11-10 2016-04-21 株式会社東洋新薬 抗糖化用組成物

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102905543A (zh) * 2010-05-25 2013-01-30 雀巢产品技术援助有限公司 协同抗氧化剂组合物
US9068138B2 (en) 2010-05-25 2015-06-30 Nestec S.A. Synergistic antioxidant composition
JP2012025706A (ja) * 2010-07-26 2012-02-09 National Institute Of Advanced Industrial Science & Technology 抗酸化剤及びその利用
BE1021587B1 (fr) * 2013-08-30 2015-12-16 S.A. Laboratoires Pharmaceutiques Trenker Composition pour le soin de la peau et son procede de preparation
JP2016056178A (ja) * 2015-11-10 2016-04-21 株式会社東洋新薬 抗糖化用組成物

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