WO2014091988A1 - Extrait de lait de soja fermenté et extrait d'hypocotyle fermenté - Google Patents

Extrait de lait de soja fermenté et extrait d'hypocotyle fermenté Download PDF

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WO2014091988A1
WO2014091988A1 PCT/JP2013/082603 JP2013082603W WO2014091988A1 WO 2014091988 A1 WO2014091988 A1 WO 2014091988A1 JP 2013082603 W JP2013082603 W JP 2013082603W WO 2014091988 A1 WO2014091988 A1 WO 2014091988A1
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fermented
extract
soymilk
isoflavone
lactic acid
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PCT/JP2013/082603
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Japanese (ja)
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由貴 山▲崎▼
幹雄 場家
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キッコーマン株式会社
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Priority to JP2014552005A priority Critical patent/JP6322580B2/ja
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L11/00—Pulses, i.e. fruits of leguminous plants, for production of food; Products from legumes; Preparation or treatment thereof
    • A23L11/50—Fermented pulses or legumes; Fermentation of pulses or legumes based on the addition of microorganisms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/48—Fabaceae or Leguminosae (Pea or Legume family); Caesalpiniaceae; Mimosaceae; Papilionaceae
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60—Sugars; Derivatives thereof
    • A61K8/602—Glycosides, e.g. rutin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics 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
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2236/00—Isolation 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/85—Products or compounds obtained by fermentation, e.g. yoghurt, beer, wine

Definitions

  • the present invention relates to a fermented soymilk extract containing a high content of isoflavone aglycone and polyamine, and in particular, has a low sugar content and a cell activation effect, an antioxidant effect, an anti-glycation effect and a moisturizing effect on epidermal keratinocytes and skin fibroblasts. It is related with the soymilk fermented extract which has anti-aging effects, such as.
  • the present invention also relates to a hypocotyl fermented extract obtained by fermenting soybean hypocotyls with lactic acid bacteria, in particular, high content of isoflavone aglycone and polyamine, cell activation action against epidermal keratinocytes and skin fibroblasts,
  • the present invention relates to a hypocotyl fermented extract having an anti-aging action such as an oxidizing action and an anti-glycation action.
  • soy milk contains high-quality proteins, isoflavone compounds, and the like, and further, it is expected to exhibit various physiological effects by producing soy peptide, isoflavone aglycone, and the like by fermentation.
  • the soymilk fermented extract is a quasi-drug raw material standard (hereinafter sometimes referred to as “Kotohara regulations”) 2006 (March 31, 2006, from the medicinal diet No. 0331030, Ministry of Health, Labor and Welfare, Ministry of Health, Labor and Welfare) "Liquid” (component code 532101).
  • the soymilk fermented solution is “an extract obtained by adding ethanol to a culture solution obtained by fermenting soymilk obtained from soybean seeds with Lactobacillus delbrueckii (L. delbrueckii) and filtering. Includes 0.01 to 0.04% nitrogen when quantified. "If it satisfies this, it can be said that safety is confirmed from the viewpoint of actual use.
  • L. delbrueckii is a lactic acid bacterium that has been used for a long time in the production of yogurt, and is considered to be highly safe from experience.
  • Isoflavone compounds contained in soybean are known to have physiological activities such as estrogenic activity, anti-estrogenic activity, and antioxidant activity, and their usefulness has attracted attention.
  • soybean is powdered as it is and the isoflavone compound is measured, the presence of 12 types of isoflavone compounds is confirmed. These are based on three types of daidzein, genistein, and glycitein (these are called isoflavone aglycones) (Chemical Formula 1).
  • isoflavone glycosides (daidine, genistin, glycitin) having these as basic skeletons, and compounds in which these isoflavone glycosides are further modified by acetylation or malonylation It exists as (Chemical formula 2).
  • isoflavone aglycone is generally considered to have a high pharmacological action because it is closer to the structure of estrogen than isoflavone glycoside. Moreover, since the hydrophobicity is higher than that of the isoflavone glycoside, it can be expected that the permeability to the skin is high. For example, with respect to genistein, it has been shown that application may have an effect of preventing skin aging (see Non-Patent Document 3, for example).
  • the amount of isoflavone compound itself is small in nature, and particularly the amount of isoflavone aglycone is extremely small.
  • soybeans contain polyamines.
  • Polyamine is a generic term for aliphatic hydrocarbons having two or more primary amino groups, and is a natural product that exists universally in the living body, and more than 20 types of polyamines have been found.
  • Typical polyamines include putrescine, spermidine, spermine and cadaverine.
  • the main physiological functions of polyamines are as follows: (1) Stabilization and structural change of nucleic acid by interaction with nucleic acid (2) Promoting action on various nucleic acid synthesis systems (3) Activation of protein synthesis system (4) Cell membrane (5) Elimination of active oxygen (6) Promotion of cell growth (7) Antiallergic action is known (for example, see Patent Document 5 and Non-Patent Documents 4 and 5) ).
  • fermented soy milk rich in isoflavone aglycone can be obtained by using lactic acid bacteria having a ⁇ -glucosidase activity, Bifidobacterium, etc. as a method for degrading isoflavone glycosides into isoflavone aglycones ( For example, see Patent Document 6 and Non-Patent Document 6-11).
  • polyamines obtained after these fermentations have not been confirmed.
  • Non-Patent Document 6-11 there are particularly few reports on conversion to isoflavone aglycone in soy milk (see, for example, Non-Patent Document 6-11).
  • Non-Patent Documents 6 and 7 L. Due to the co-culture of delbrueckii and other lactic acid bacteria, L. It is difficult to say that the conversion is made by delbrueckii alone.
  • Non-Patent Document 8 L., which is an enteric bacterium of birds.
  • delbrueckii analogues have been reported to convert genistin to genistein in a synthetic medium, the strain has not been fully identified.
  • Non-Patent Document 9 L. delbrueckii subsp. Although conversion to isoflavone aglycone by bulgaricus alone has been reported, the isoflavone content of the soymilk used for fermentation (reconstituted liquid with soybean isolate protein) is small (total amount 42 mg / L, 103 ⁇ M), and the resulting isoflavone aglycone is about 24 mg. / L (about 90 ⁇ M). About the nonpatent literature 10 and 11, the fermented liquor of high isoflavone aglycone content is obtained by fermenting soymilk, without adding saccharides.
  • Non-Patent Document 12 reports that when glucose is added to soy milk and fermented with lactic acid bacteria, the isoflavone glycoside is converted to the aglycon when a specific strain is used. However, the amount of polyamine has not been confirmed for any of these fermentations.
  • soybean hypocotyls which are the parts that become buds and roots when germinating soybeans, are rich in micronutrients such as proteins and oligosaccharides, as well as isoflavones and saponins. It has been reported that a fermented product containing equol is obtained by fermenting with a specific Lactococcus d'Albier having (Patent Document 8).
  • Skin is a tissue composed of epidermis and dermis, and functions as a barrier that protects the body from physical or chemical stress from the outside.
  • the epidermis existing outside the skin consists of a basal layer, a spiny layer, a granule layer, and a stratum corneum, and is mainly composed of keratinocytes.
  • the keratinocytes that have divided in the basement membrane move to the upper layer through differentiation and maturation, reach the outer layer of the horny layer, and then drop off and repeat turnover (metabolism) to form the epidermis.
  • epidermal keratinocyte activators are used for improving skin roughness, moisturizing effect, skin dullness improving effect, whitening effect, and skin texture improvement.
  • soymilk fermented extract the hair-growth effect by estrogen receptor ⁇ agonist activation has been reported (for example, see Patent Document 3), but remarkable cell activation against epidermal keratinocytes by isoflavone aglycone and polyamine-rich fermented soymilk fermented extract. No effect has been reported so far.
  • Skin fibroblasts are cells that exist in the dermis and produce collagen, elastin, hyaluronic acid, and the like, and are known to contribute to forming a dermal structure by using collagen as a fiber bundle.
  • an agent having an activating effect on skin fibroblasts is useful as an active ingredient of a skin external preparation, particularly a skin external preparation for preventing aging.
  • no significant cell activation effect on skin fibroblasts by isoflavone aglycone and soymilk fermented extract containing a high amount of polyamine has been reported so far.
  • the skin is an organ located in the outermost layer of the living body, and is an organ that is greatly affected by the external environment.
  • the most important of these is the presence of ultraviolet rays.
  • reactive oxygen species are generated and converted into various radical species in the living body, which has the positive effect of sterilization, elimination of invading substances into the body, etc., but due to its high reactivity, the epidermis Attacks hyaluronic acid, collagen, elastin, and fibroblasts, which are constituents of cells and tissues, and the dermis, and negative effects are caused by their deterioration, reduction, or degeneration.
  • an agent having an action of eliminating active oxygen species is useful as an active ingredient of a skin external preparation, particularly a skin external preparation for preventing aging.
  • a skin external preparation for preventing aging.
  • the antioxidant effect of isoflavone aglycone and polyamine-rich soymilk fermented extract has not been reported so far.
  • Carbohydrates are very important as energy sources in living organisms including humans.
  • carbohydrates are known to cause glycation reactions with proteins.
  • the first stage is a non-enzymatic reaction between a carbonyl group of a carbohydrate and an amino group such as a protein, and finally a final glycation product (hereinafter referred to as “AGEs”) from a Schiff base through an Amadori compound.
  • AGEs final glycation product
  • Due to the saccharification reaction the protein is modified non-enzymatically by sugar, and as a result, denaturation of the protein, cross-linking between proteins, and the like occur, resulting in a decrease in protein function.
  • the glycation reaction not only causes direct damage by modifying and changing the structure of extracellular matrix constituent proteins such as collagen, but also affects cellular responses by being recognized by receptors with glycated proteins as ligands. Bring.
  • the extracellular matrix components such as collagen occupy the majority of the dry weight in tissues such as bone and skin. Therefore, for example, when collagen is glycated and abnormally crosslinked, osteoporosis, osteoarthritis, etc. occur in bone and cartilage tissue, and elasticity in skin, dullness due to yellowing, etc. occur. . Furthermore, since abnormally cross-linked collagen and the like are less susceptible to degradation by collagenase or the like, expression of collagenase or the like is induced, and problems such as degradation to normal collagen occur.
  • the saccharification reaction is suppressed in some form, that is, the formation of AGEs can be suppressed, or the degradation of AGEs can be promoted, it is effective in preventing or improving skin elasticity and dullness. Expected to be.
  • N-phenacyl thiazolium bromide is known as a compound having an anti-glycation action (see, for example, Non-Patent Document 14).
  • this compound has a safety problem and is not suitable as a pharmaceutical or a topical skin preparation.
  • an ingredient derived from a natural product having an anti-glycation action for example, an extract from olive is known (see, for example, Patent Document 12).
  • an extract from olive is known (see, for example, Patent Document 12).
  • the provision of a substance having an anti-glycation action is not sufficient, and the development and provision of a further new anti-glycation action substance is strongly demanded.
  • soybean hot water extract and isoflavone are also reported to have an anti-glycation effect (see, for example, Patent Document 13), the production of AGEs cannot be completely suppressed using these, and the effect Is not enough.
  • no anti-glycation action by isoflavone aglycone and polyamine-rich soymilk fermented extract has been reported so far.
  • the amount of moisture in the stratum corneum is closely related to the condition of the skin, and in order to maintain healthy bare skin, it is necessary that the stratum corneum retains moderate moisture.
  • the stratum corneum has a barrier function that prevents foreign matter from entering the skin and transpiration of moisture necessary for the living body. When the stratum corneum barrier function is lowered, the stratum corneum water content is lowered with an increase in the transdermal water transpiration amount, and rough skin and various aging symptoms are caused.
  • an agent having an effect of increasing the amount of moisture in the stratum corneum or an agent having an effect of enhancing the function of the stratum corneum is useful as an active ingredient of an external preparation for skin, particularly an external preparation for preventing aging.
  • an external preparation for skin particularly an external preparation for preventing aging.
  • the moisturizing action of isoflavone aglycone and polyamine-rich soymilk fermented extract has not been reported so far.
  • Japanese Patent No. 2804312 Japanese Patent No. 3184114 JP 2012-176931 A JP 2006-070146 A JP 2009-234939 A JP 2001-340059 A Japanese Patent No. 3014145 Japanese Patent No. 5030790 JP 2012-006954 A JP 2012-46544 A JP 2012-102054 A JP 2001-122758 A JP 2012-2119014 A
  • the first problem is that the content of the isoflavone compound, which is a component particularly expected as a physiologically active substance contained in soybean, is extremely small.
  • soymilk fermented extracts have a low isoflavone compound content (0 to 120 ⁇ M) and a lower isoflavone aglycone content (0 to 60 ⁇ M, conversion rate to isoflavone aglycone 0 to 50%). From such a background, a fermented soymilk extract having a high content of isoflavone aglycone is strongly demanded.
  • the second problem is that the content of polyamine, which is a component expected as another physiologically active substance, is low.
  • the total amount of polyamine in the soymilk fermented extract actually marketed is 10 to 15 ⁇ M, and therefore, a fermented soymilk extract having a high polyamine content is strongly demanded.
  • the reason for the very low polyamine content of commercially available soymilk fermented extract is that the solubility of polyamine is low in ethanol used in production. Therefore, in order to produce a fermented soymilk extract having a high polyamine content, it is necessary to improve the concentration of the polyamine in the fermentation broth and optimize the concentration of the organic solvent used for extraction.
  • a third problem is that carbohydrates such as glucose remain. It has been reported that oligosaccharides contained in soybeans are sucrose (sucrose, 5%), stachyose (4%), raffinose (1.1%), and verbus course (trace) (for example, Fumio Yamauchi et al. Ed., “Soy Science”, Asakura Shoten, 1993, p. 49), in lactic acid bacteria fermentation using soybean raw materials such as soy milk, depending on the type of lactic acid bacteria, there is a shortage of carbohydrates. When sugars such as glucose are added to compensate for this, it is considered that undigested sugars remain in the fermentation broth.
  • This invention is made
  • the present inventors performed lactic acid bacteria fermentation of soy milk without supplementing carbohydrates, and by extracting this, isoflavone aglycone and polyamine are highly contained, A fermented soymilk extract with a low glucose content is obtained, which further has anti-aging effects such as cell activation, antioxidant, anti-glycation and moisturizing effects on epidermal keratinocytes and skin fibroblasts. I found it.
  • fermenting soybean hypocotyls with lactic acid bacteria and extracting them yields a hypocotyl fermented extract containing a high content of isoflavone aglycone and polyamine, which further promotes cell activation against epidermal keratinocytes and skin fibroblasts. It has been found that it has an anti-aging action such as an action, an antioxidant action and an anti-glycation action, and has completed the present invention. That is, the present invention relates to the following.
  • step (A), (B) and (C) (A) a step of fermenting soy milk with lactic acid bacteria; (B) a step of mixing the fermented product obtained in step (A) and an organic solvent; and (C) a step of removing the solid content produced in step (B);
  • step (A) The fermented soymilk extract according to any one of [1] to [3], wherein the lactic acid bacterium in the step (A) is Lactobacillus delbrueckii.
  • step (P) the soymilk fermented extract according to any one of [1] to [4], which is obtained by a method comprising a step of (P) pre-culture with soymilk.
  • the anti-aging agent according to [8] which has one or more of a skin keratinocyte activation effect, a skin fibroblast activation effect, an antioxidant effect, an anti-glycation effect and a moisturizing effect.
  • a cosmetic, an external preparation for skin, a pharmaceutical or a food or drink comprising the fermented extract according to any one of claims [1] to [7].
  • a method for producing a polyamine which comprises fermenting soy milk with lactic acid bacteria and then extracting the polyamine.
  • a method for producing a polyamine comprising fermenting a soybean hypocotyl with lactic acid bacteria and then extracting the polyamine.
  • a method for producing isoflavone aglycone or polyamine comprising a step of fermenting soybean hypocotyl with Lactobacillus delbrueckii.
  • a fermented soymilk product obtained by fermentation with a lactic acid bacterium selected from delbrueckii JCM 1012.
  • a soymilk fermented extract containing a high content of isoflavone aglycone and polyamine and in particular, it has a low sugar content and has a cell activation effect and an antioxidant effect on epidermal keratinocytes and skin fibroblasts.
  • the fermented soymilk extract exhibiting anti-aging effects such as anti-glycation action and moisturizing action can be provided.
  • a hypocotyl fermented extract obtained by fermenting soybean hypocotyls with lactic acid bacteria can be provided, in particular, high content of isoflavone aglycone and polyamine, and epidermal keratinocytes and skin fibers.
  • hypocotyl fermented extract having an anti-aging action such as a cell activation action, an antioxidant action and an anti-glycation action on blast cells.
  • the fermented soymilk extract and hypocotyl fermented extract of the present invention are useful for cosmetics, pharmaceuticals, and foods and drinks, and particularly useful for cosmetics.
  • the “fermented soymilk extract” means the following steps (A), (B) and (C): (A) a step of fermenting soy milk with lactic acid bacteria; (B) refers to an extract obtained by a method comprising a step of mixing the fermented product obtained in step (A) with an organic solvent; and (C) a step of removing the solid content produced in step (B).
  • soy milk refers to various known soy milks, and includes, for example, unprepared soy milk, prepared soy milk, soy milk beverages, and the like. It can be prepared from one or more parts of soybean seed endosperm, hypocotyl (also referred to as germ) and skin (hereinafter referred to as soybean raw material), and each is extracted from one or more parts and mixed appropriately. You can also A suspension obtained by appropriately pulverizing and immersing a soybean raw material or a slurry obtained by immersing a soybean raw material and then wet pulverizing it can be used as a fermentation raw material as the soy milk of the present invention.
  • soy milk of the present invention also includes so-called soy bean prepared by dissolving, suspending, or homogenizing powdered soy beans or whole-grain soybeans in water, and soy milk made from these soy milk.
  • soy milk of the present invention includes so-called protein beverages that have soy protein as a main component and have a soy milk-like flavor.
  • Soybean varieties, brands, and colors are not particularly limited, and for example, domestic soybeans, US soybeans such as IOM, genetically modified soybeans, or genetically non-recombinant soybeans can be used. Green soybeans, which are immature seeds of soybeans, can also be used.
  • soymilk fermented extract containing a high amount of isoflavone aglycone soymilk having a total content of isoflavone compounds of isoflavone aglycone and isoflavone glycoside (including acetyl glycoside and malonyl glycoside) of 150 ⁇ M or more is preferably used.
  • the lactic acid bacterium is not particularly limited as long as it is a bacterium that produces lactic acid from saccharides by fermentation.
  • Lactobacillus bacteria are preferably used, and are described in the outer standard of soymilk fermentation broth.
  • delbrueckii is particularly preferably used.
  • L. As for delbrueckii there is no particular limitation on the subspecies. delbrueckii subsp. lactis, L.L. delbrueckii subsp. bulgaricus, L .; delbrueckii subsp. delbrueckii and the like.
  • delbrueckii subsp. lactis JCM 1105 From the viewpoint of obtaining a soymilk fermented extract with a low glucose and sucrose content and a soymilk fermented extract with a high polyamine content, delbrueckii subsp. lactis JCM 1105, L. delbrueckii subsp. lactis JCM 1148, L. delbrueckii subsp. bulgaricus JCM 1001, L. delbrueckii subsp. lactis JCM 1010 and L. delbrueckii subsp. Bacteria selected from delbrueckii JCM 1012 are preferably used.
  • a lactic acid bacterium having a high conversion rate from an isoflavone glycoside to isoflavone aglycone described below is preferably used.
  • delbrueckii subsp. Lactis JCM 1105 or 1148 strain is particularly preferably used.
  • the fermentation conditions for the lactic acid bacteria in the step (A) are not particularly limited as long as the lactic acid bacteria grow and the soymilk is fermented, and can be appropriately selected according to the type of the lactic acid bacteria to be used. Soymilk fermentation can be confirmed by an increase in the amount of lactic acid in the fermented product.
  • the conversion rate of isoflavone glycosides in soymilk to isoflavone aglycone is 50% or more, particularly 55% or more are preferable.
  • the conversion rate of isoflavone aglycone is calculated by calculating the molar concentration of various isoflavone compounds before and after fermentation, [(isoflavone glycoside before fermentation) ⁇ (isoflavone glycoside after fermentation)] / (before fermentation). It can be calculated as (isoflavone glycoside) ⁇ 100 (%).
  • the soy milk used for fermentation can be added with sugars, nitrogen sources, etc. as necessary, pH can be adjusted, and sterilization can be performed by heating or the like.
  • soymilk extract with a low content of carbohydrates particularly, reducing sugars used as a raw material for the Maillard reaction
  • Such saccharides include: all monosaccharides including, for example, glucose, fructose and glyceraldehyde, reducing sugars such as maltose-type disaccharides or oligosaccharides including lactose, arabinose and maltose; and, for example, by hydrolysis, such as sucrose
  • reducing sugars such as maltose-type disaccharides or oligosaccharides including lactose, arabinose and maltose
  • hydrolysis such as sucrose
  • sucrose Non-reducing sugars that are reducing sugars are exemplified.
  • the lactic acid bacteria to be inoculated may be pre-cultured in any medium, and can be cultured in, for example, plant-derived raw material medium (soy milk, plant-derived peptone, etc.), yeast extract, various synthetic media (MRS medium, etc.), etc. .
  • pre-culture can be performed using soy milk from the viewpoint of simplifying the production process and avoiding the use of a medium containing animal-derived materials.
  • the culture conditions for pre-culture are not particularly limited as long as lactic acid bacteria are increased.
  • the fermentation temperature can be appropriately selected according to the type of lactic acid bacteria, and is not particularly limited, but can be carried out at 10 to 50 ° C., preferably 20 to 40 ° C.
  • cultivation it may leave as it is or may be controlled with an acid or an alkali.
  • Various carbon sources and nitrogen sources can also be fed. Any conditions such as aerobic conditions, anaerobic conditions, stirring culture, and stationary culture can be selected depending on the type of lactic acid bacteria to be used.
  • Fermentation time can be appropriately selected according to the type of lactic acid bacteria, and is not particularly limited. Fermentation can be performed for 6 to 72 hours, conveniently 12 to 60 hours.
  • lactic acid can be an indicator of the progress of lactic acid bacteria fermentation
  • the culture can be stopped depending on the concentration of lactic acid. For example, the culture is stopped when the lactic acid concentration reaches 0.1 to 7 mg / mL. can do.
  • the sugar has been reduced by analyzing the sugar in the culture solution, and cultured in a state where the sugar is consumed.
  • the saccharide include glucose, fructose, sucrose, and maltose.
  • the method for analyzing these carbohydrates is not particularly limited, but is preferably a phosphate-phenylhydrazine method (a method in which a saccharide is separated by a column and then reacted with a phosphate-phenylhydrazine reagent to detect it after fluorescence derivatization. ) Or a method using a biosensor.
  • the pH of the fermented product may be adjusted as necessary. For example, the pH lowered due to the production of lactic acid may be appropriately adjusted to neutral with alkali. After completion of fermentation, the formed card may be destroyed by stirring.
  • the obtained fermented product may be mixed with an organic solvent in the step (B) as it is, but from the viewpoint of efficiently removing the high molecular protein in the step (B), heat sterilization may be performed after completion of the fermentation. desirable.
  • the heating conditions are not particularly limited as long as the solids are sufficiently formed. For example, the heating is performed at 60 to 120 ° C. for 1 to 120 minutes, and conveniently at 80 to 110 ° C. for 20 to 60 minutes. Can be implemented.
  • the obtained fermented product is mixed with an organic solvent.
  • desired components such as an isoflavone compound
  • desired components can be extracted in the organic solvent from the obtained fermented material.
  • a polar solvent miscible with water is preferably used.
  • those having high safety are preferable, and ethanol, butylene glycol, and the like are particularly preferably used.
  • ethanol is described in the outer standard of a soymilk fermentation liquid, it is used especially preferably.
  • ethanol is also preferably used when blending fermented soymilk extract with food and drink and oral medicine.
  • an amount and a concentration at which a solid content is generated and separated from a clear extract are preferable.
  • an organic solvent in an amount of 5 to 90% (v / v) can be added to a culture solution.
  • v / v a culture solution
  • ethanol 15% (v / v) or more, preferably 50% (v / v) or more of ethanol can be added to the culture solution.
  • operations such as heating, cooling, and standing can also be performed.
  • Step (C) for removing the solid content generated in the step (B) is performed.
  • Step (C) can be performed using any method that can remove solids, and for example, a method of separating the supernatant by standing or centrifuging, a method of filtering, or the like can be used.
  • additional steps may be performed depending on the purpose.
  • inclusion of desired components such as isoflavone compounds can also be carried out by adding cyclodextrin or the like.
  • the addition of cyclodextrin can be performed at any stage as long as it is performed prior to the removal of the solid content in the step (C).
  • cyclodextrin ⁇ -cyclodextrin or ⁇ -cyclodextrin can be used, and ⁇ -cyclodextrin can be preferably used for the purpose of inclusion of an isoflavone compound.
  • the “hypocotyl ferment extract” means the following steps (A ′), (B ′) and (C ′): (A ′) a step of fermenting soybean hypocotyls with lactic acid bacteria; (B ′) a step of mixing the fermented product obtained in step (A ′) with an organic solvent; and (C ′) a step of removing solids produced in step (B ′); For example, a liquid obtained by removing the solid content in the step (C ′), a concentrated liquid obtained by concentrating this, or a solid obtained by drying the liquid may be used.
  • soy hypocotyl refers to a soy hypocotyl (also referred to as germ), which is not only a raw soy hypocotyl but also subjected to any pretreatment such as degreasing, roasting, dipping, and heat treatment. Including.
  • the soybean hypocotyl itself can be used, or it may be pulverized.
  • a suspension of soybean hypocotyl or its pulverized product suspended in water or a hypocotyl extract obtained by extracting soybean hypocotyl or its pulverized product with water and removing the solid content It can also be used.
  • soybean hypocotyl The variety, brand, and color of the soybean from which the soybean hypocotyl is derived are not particularly limited, and any soybean can be used in the same manner as mentioned for the soy milk.
  • Steps (A ′), (B ′) and (C ′) are the same as steps (A), (B) and (C), respectively, except that soybean hypocotyl is used instead of soy milk. Can do.
  • the soymilk fermented extract or hypocotyl fermented extract (hereinafter also simply referred to as “fermented extract”) thus obtained can be used as it is as a raw material for cosmetics, external preparations for skin, pharmaceuticals and foods and drinks. Further, it can be appropriately diluted with water, an organic solvent or the like, or a preservative such as paraben or phenoxyethanol can be added. Further, for example, the organic solvent can be distilled off by heating or decompression, the components can be concentrated, and pulverization can be performed by freeze drying or spray drying. The powdered product can be dissolved, dispersed or suspended in water or an organic solvent.
  • the fermented extract of the present invention preferably has a high content of isoflavone compounds from the viewpoint of exerting various actions.
  • the isoflavone analysis can be performed using a known method capable of analyzing various isoflavone compounds, and preferably an HPLC method is used.
  • the isoflavone compound refers to daidzein, daidzin, acetyl daidzin, malonyl daidzin, genistein, genistin, acetylgenistin, malonylgenistin, glycitein, glycitin, acetylglycitin and malonylglycitin.
  • daidzein, genistein and glycitein which are isoflavone aglycones, are particularly large from the viewpoint of exerting various actions.
  • the concentration of the isoflavone compound contained in the fermented extract of the present invention is preferably as high as possible from the viewpoint of exhibiting various actions, and preferably contains 150 ⁇ M or more of the isoflavone compound.
  • isoflavone aglycone is preferably 75 ⁇ M or more, and more preferably 150 ⁇ M or more.
  • the isoflavone aglycone content is preferably 550 ⁇ M or more, more preferably 700 ⁇ M or more, and further preferably 1000 ⁇ M or more.
  • the glycitein content is particularly preferably 100 ⁇ M or more, and more preferably 200 ⁇ M or more.
  • the fermented extract of the present invention preferably has a high polyamine content from the viewpoint of exhibiting various effects.
  • the polyamine analysis can be performed using a known method capable of analyzing various polyamines such as an HPLC method and an enzymatic method, and the HPLC method is preferably used. Specifically, Novella-Rodriguez S.M. Based on these methods (J. Agric. Food Chem., 48, 5117-5123 (2000)), polyamines can be analyzed using HPLC.
  • the polyamine is not particularly limited as long as it is an aliphatic hydrocarbon having two or more primary amino groups, and examples thereof include putrescine, spermidine, spermine, and cadaverine.
  • the concentration of the polyamine contained in the fermented extract of the present invention is preferably as high as possible from the viewpoint of exhibiting various effects, and the total of putrescine, spermidine and cadaverine, which are the main polyamines in the fermented extract, is preferably 20 ⁇ M or more, and 30 ⁇ M. More preferably, it is more preferably 40 ⁇ M or more.
  • the sum of spermidine and cadaverine is preferably 310 ⁇ M or more, and more preferably 400 ⁇ M or more.
  • the fermented extract of the present invention may have the above content by adding each of these components itself (raw powder etc.) to the above isoflavone compound, isoflavone aglycone and polyamine. Since it is expensive, it is desirable that it is a fermented extract satisfying the above content without adding such from the viewpoint of economy.
  • the present inventors confirmed that the fermented extract of this invention shows a high effect (an antioxidant action, an anti-glycation action, etc.) compared with an isoflavone compound alone. ing.
  • the carbohydrate contained in the obtained fermented extract is a raw material for the Maillard reaction that causes aging, and it causes stickiness when applied to the skin when blended in cosmetics, so less is preferable .
  • sugars include glucose, fructose, sucrose, and maltose.
  • the method for analyzing these carbohydrates is not particularly limited, but is preferably a phosphate-phenylhydrazine method (a method in which a saccharide is separated by a column and then reacted with a phosphate-phenylhydrazine reagent to detect it after fluorescence derivatization. ) Or a method using a biosensor.
  • the fermented extract of the present invention preferably has a saccharide content of 4.0 mg / mL or less, more preferably 3.0 mg or less, and even more preferably 1.5 mg / mL or less.
  • the sum of the contents of glucose and sucrose is preferably 3.0 mg / mL or less, and more preferably 1.5 mg / mL or less.
  • the fermented extract of the present invention comprises a sum of glucose and sucrose contents (mg / mL): an isoflavone compound content ( ⁇ M), that is, a sum of glucose and sucrose contents (mg / mL) /
  • the content ( ⁇ M) of the isoflavone compound is preferably 0.1 or less, more preferably 0.05 or less, further preferably 0.015 or less, and particularly preferably 0.01 or less. preferable.
  • the fermented extract of the present invention contains isoflavone aglycone, and sum of glucose and sucrose content (mg / mL): isoflavone aglycone content ( ⁇ M), that is, sum of glucose and sucrose content.
  • the content ( ⁇ M) of (mg / mL) / isoflavone aglycone is preferably 0.2 or less, more preferably 0.1 or less, and particularly preferably 0.01 or less.
  • the fermented extract of the present invention comprises the sum of glucose and sucrose content (mg / mL): the content of polyamine ( ⁇ M), that is, the sum of glucose and sucrose content (mg / mL) / polyamine.
  • the content ( ⁇ M) is preferably 0.3 or less, more preferably 0.25 or less, further preferably 0.1 or less, and particularly preferably 0.05 or less.
  • the other components of the fermented extract of the present invention are not particularly limited, but the liquid nitrogen content is preferably 0.01 to 0.04% described in the outer standard.
  • the fermented extract of the present invention may be suspended or transparent, and the color is preferably, for example, pale yellow, pale brown or colorless.
  • the fragrance is not particularly limited, but a fragrance having a small soybean odor and a refreshing fragrance of lactic acid bacteria fermentation is preferable.
  • the fermented extract of the present invention exhibits one or more of cell activation action, antioxidant action, anti-glycation action and moisturizing action on epidermal keratinocytes and dermal fibroblasts, In one embodiment, it preferably exhibits at least one of cell activation and anti-glycation effects on epidermal keratinocytes and dermal fibroblasts.
  • the cell activation activity of epidermal keratinocytes is determined by adding 0.01 to 50% of the fermented extract of the present invention to commercially available normal human epidermal keratinocytes (Kurabo Co., Ltd.) to prepare a culture solution. This can be used to determine whether to promote cell growth.
  • the sample has an activation activity of epidermal keratinocytes
  • the activity when no sample is added is 100%.
  • the activation activity of epidermal keratinocytes when a sample is added is 110% or more.
  • the cell activation activity of skin fibroblasts is prepared by adding 0.01 to 50% of the fermented extract of the present invention to commercially available normal human skin fibroblasts (manufactured by Kurabo) to prepare a culture solution. This can be used to determine whether to promote cell growth.
  • the case where the sample has a fibroblast activation activity refers to a case where the activation activity of the fibroblast when the sample is added is 110% or more, assuming that the activity when the sample is not added is 100%.
  • the antioxidant action can be measured by adding the fermented extract of the present invention to DPPH radical, which is a pseudo-active oxygen, and determining whether or not to erase the DPPH radical.
  • DPPH radical which is a pseudo-active oxygen
  • the case where the sample has an antioxidant action means that the DPPH radical elimination rate when the sample is added is 10% or more when the DPPH radical elimination rate without addition of the sample is 0%.
  • Antioxidant action is prepared by adding 0.01 to 50% of the fermented extract of the present invention to commercially available normal human epidermal keratinocytes (Kurabo Co., Ltd.). This can be used to determine whether to reduce cell damage due to exposure to reactive oxygen species.
  • the case where the sample has a cytoprotective action refers to the case where the cell viability when the sample is added is increased by 10% or more with respect to the cell viability when the sample is not added under the condition where the active oxygen is exposed.
  • the anti-glycation action can be measured by adding the fermented extract of the present invention to a mixed solution of glucose and human serum albumin and using this to determine whether to suppress the production of AGEs.
  • the case where the sample has an anti-glycation effect refers to the case where the AGEs production inhibitory activity when the sample is added is 10% or more, for example, when the sample-free AGEs production inhibitory activity is 0%.
  • the moisturizing effect is measured by measuring the stratum corneum water content and transdermal water transpiration after applying the skin lotion containing 0.01 to 50% of the fermented extract of the present invention to humans. It can be measured by confirming the decrease in the amount.
  • the moisture content of the stratum corneum increases by 10% or more compared to the case where the sample cost-containing lotion is applied by applying the sample-containing lotion, or the transdermal moisture transpiration amount is 10 If it decreases by more than%.
  • the present invention also relates to an anti-aging agent containing the fermented extract of the present invention.
  • an anti-aging agent containing the fermented extract of the present invention.
  • the present invention also relates to a cosmetic and a skin external preparation containing the fermented extract of the present invention.
  • the cosmetic and external preparation for skin of the present invention can be prepared by blending the fermented extract of the present invention with various types of base materials known as normal cosmetic and external preparation for skin according to conventional methods.
  • the blending amount of the fermented extract is preferably 0.01 to 50% by mass with respect to the total amount from the viewpoint of effects and stability.
  • the form of the cosmetic and the external preparation for skin is not particularly limited, and any dosage form such as an emulsion, cream, aqueous solution, pack, etc. can be selected.
  • ingredients blended in normal cosmetics and skin external preparations such as oils, powders, purified water, polymer compounds, gelling agents, ultraviolet rays Absorbers, ultraviolet scattering agents, antioxidants, dyes, preservatives, fragrances, and cosmetic ingredients can be appropriately selected and used within a range not impairing the effects of the present invention.
  • a pharmaceutical preparation can be prepared by adding a pharmaceutically acceptable excipient.
  • the pharmaceutical preparation is not particularly limited, but is externally applied to tablets, capsules, granules, fine granules, powders, liquids, syrups, chewable, troches, etc., ointments, gels, creams, patches, etc.
  • the dosage form may be an agent, injection, sublingual, inhalant, eye drop, suppository and the like.
  • the pharmaceutical of this invention can also be provided as a kit containing the fermented extract of this invention.
  • the fermented extract of the present invention can be added to food and drink from the viewpoint of ease of ingestion.
  • the food and drink include supplements, foods for specified health use, functional nutritional foods, health foods, functional foods, health supplements, and normal foods and drinks.
  • the shape of the food and drink includes liquids such as juices, soft drinks, drinks, teas, solids such as biscuits, tablets, granule powders, powders and capsules, semi-fluid forms such as pastes, jellies, soups, seasonings, dressings, etc. Is mentioned.
  • the present invention is also characterized in that the soy milk is fermented with lactic acid bacteria and then the polyamine is extracted, and the method for producing polyamines, and the soybean hypocotyl is fermented with lactic acid bacteria and then the polyamines are extracted.
  • the present invention also relates to a method for producing a polyamine.
  • a polyamine can be produced without the addition of an acid.
  • the method can be carried out with reference to the above description relating to the fermented extract of the present invention.
  • the fermentation of soy milk with lactic acid bacteria and the fermentation of soybean hypocotyls with lactic acid bacteria are carried out by performing the above steps (A) and (A ′). Can be done with reference.
  • Extraction of the polyamine from the fermented product can be performed using a technique known to those skilled in the art, for example, referring to the steps (B) and (C) and the steps (B ′) and (C ′). be able to.
  • the present invention also relates to a method for producing isoflavone aglycone or polyamine, comprising a step of fermenting soybean hypocotyls with lactic acid bacteria Lactobacillus delbrueckii.
  • the method can be carried out with reference to the above description regarding the fermented extract of the present invention.
  • soy milk is also added to L. delbrueckii subsp. lactis JCM 1105, L. delbrueckii subsp. lactis JCM 1148, L. delbrueckii subsp. bulgaricus JCM 1001, L. delbrueckii subsp. lactis JCM 1010 and L. delbrueckii subsp.
  • the present invention also relates to a fermented soymilk obtained by fermentation with a lactic acid bacterium selected from delbrueckii JCM 1012 and a fermented hypocotyl obtained by fermenting a soy hypocotyl with lactobacillus delbrueckii.
  • These fermented products can be obtained by referring to the above description of the fermented extract of the present invention, for example, referring to the above steps (A) and (A ′).
  • delbrueckii obtained from RIKEN was inoculated into MRS medium and pre-cultured at 37 ° C. for 24 hours.
  • the culture medium was collected by centrifugation, and then the 10-fold concentrated bacterial solution was inoculated into non-adjusted soy milk (manufactured by Kikkoman Soy Foods) and anaerobically cultured at 37 ° C. for 48 hours.
  • the mixture was heated at 100 ° C. for 30 minutes, and then ethanol was added to a content of 50% (v / v) and stirred.
  • the added solution was allowed to stand at 4 ° C. for 24 hours, and then insoluble matters were removed by centrifugation and filtration to obtain a clear fermented soymilk extract.
  • Example 1-2 ⁇ Preparation of fermented soymilk extract that has been pre-cultured with unadjusted soymilk>
  • the soymilk fermented extract was prepared by the method shown below.
  • L. delbrueckii JCM 1105 was inoculated into unconditioned soymilk and pre-cultured at 37 ° C. for 24 hours.
  • the culture medium was collected by centrifugation, and then the 10-fold concentrated bacterial solution was inoculated into unadjusted soymilk (manufactured by Kikkoman Soy Foods) and cultured at 37 ° C. for 48 hours. After completion of the culture, the mixture was heated at 100 ° C.
  • L. delbrueckii subsp. lactis JCM 1105 or L. delbrueckii subsp. lactis JCM 1148 obtained from RIKEN
  • inoculated into MRS medium pre-cultured at 37 ° C. for 24 hours
  • heat at 100 ° C. for 30 minutes add ethanol to 50% (v / v), stir, let stand at 4 ° C. for 24 hours, and then remove insoluble matter by centrifugation and filtration.
  • a clear hypocotyl fermented extract was obtained.
  • Example 2 Preparation of hypocotyl extract (non-fermented)> The hypocotyl extract prepared in Example 2 is heated at 100 ° C. for 30 minutes, and then ethanol is added to a content of 50% (v / v), followed by centrifugation and filtration to obtain a clear hypocotyl extract. (Non-fermented) was obtained.
  • a linear gradient starting with the containing solution and ending with 35% eluent A and 65% eluent B was used.
  • the flow rate was 2.0 mL / min, and the absorbance at 254 nm was measured using a UV detector.
  • the isoflavone content in the sample was calculated by determining the peak area of each isoflavone from the standard solution and the HPLC chart of the sample.
  • a purified product of isoflavone compound manufactured by Wako Pure Chemical Industries (Daidin, glycitin, genistin, daidzein, glycitein, genistein, 6 "-O-acetyldaidine, 6" -O-acetylglycitin, 6 "-O- Acetylgenistin, 6 ′′ -O-malonyldaidine, 6 ′′ -O-malonylglycitin and 6 ′′ -O-malonylgenistin) were used.
  • the conversion rate from isoflavone glycosides to isoflavone aglycones was calculated by calculating the molar concentration of isoflavone glycosides (including malonyl glycosides) before and after fermentation, and [(isoflavone glycosides before fermentation)-(fermentation Later isoflavone glycoside)] / (isoflavone glycoside before fermentation) ⁇ 100 (%).
  • Table 1 shows the concentrations of various isoflavones in the samples of the examples and comparative examples and the commercially available soymilk fermentation broth.
  • Example 1-1 Regarding the fermented soymilk extract prepared in Example 1-1, there was a difference in the presence or absence of aglyconization depending on the type of lactic acid bacteria used.
  • Bulgaricus JCM 1001 When Bulgaricus JCM 1001 was used, the reduction of isoflavone glycosides daidin and genistin and the formation of isoflavone aglycones daidzein and genistein were observed, and a fermented soymilk extract containing high isoflavone aglycone content was obtained.
  • the concentration of these isoflavone aglycones was higher than the soymilk fermentation broth already on the market.
  • the soymilk fermented extract prepared in Example 1-2 also showed aglyconization of isoflavones, not only MRS medium but also unadjusted soymilk can be used for the pre-culture of the soymilk fermented extract. Became clear.
  • hypocotyl fermented extract prepared in Example 2 is also described in L.P. delbrueckii subsp. lactis JCM 1105 and L. delbrueckii subsp.
  • Lactis JCM 1148 was used, compared to the hypocotyl extract (non-fermented) prepared in Comparative Example 2, the reduction of isoflavone glycosides daidin, glycitin and genistin and isoflavone aglycone daidzein, glycitein and An increase in genistein was observed.
  • the isoflavone aglycone content of the hypocotyl fermented extract was higher than that of the fermented soymilk extract of Example 1-1 prepared using the same lactic acid bacteria for fermentation.
  • glycitein which was shown to have a particularly large contribution to the AGEs production inhibitory activity in Test Example 4 described later, contained a large amount of 200 ⁇ M or more.
  • Example 1-1 concentration of putrescine, spermidine and cadaverine in the fermented soymilk extract prepared in Example 1-1 was about 2.0-2.5 times higher than the soymilk extract (non-fermented) of Comparative Example 1. It was. The concentration of these polyamines was higher than the soymilk fermentation broth already on the market.
  • the concentrations of putrescine, cadaverine and spermidine in the hypocotyl fermented extract prepared in Example 2 should be about 1.4 to 3.0 times higher than the hypocotyl extract (non-fermented) of Comparative Example 2. I understood.
  • the concentration of spermine was very small compared to the measurement limit or less than putrescine, cadaverine and spermidine.
  • the polyamine content of the hypocotyl fermented extract was even higher than that of the soymilk fermented extract, and in particular, contained very large amounts of spermidine and cadaverine.
  • each component in Tables 4 and 5 was calculated as follows: (A1) Isoflavone compound: Total amount ( ⁇ M) of nine isoflavones described in Table 1 (A2) Isoflavone aglycone: total amount ( ⁇ M) of daidzein, glycitein and genistein listed in Table 1 (B) Polyamine: Total amount ( ⁇ M) of putrescine, spermidine and cadaverine described in Table 2 (C) Carbohydrate: Total amount (mg / mL) after converting glucose and sucrose contents shown in Table 3 to ⁇ M
  • Normal human epidermal keratinocytes [manufactured by Kurabo Industries, product name NHEK (NB)] are seeded in a 96-well microplate so as to be 5 ⁇ 10 3 cells per well, at 37 ° C. in a carbon dioxide concentration of 5 vol%. Cultured for 48 hours.
  • HuMedia-KG2 medium HuMedia-KG2 medium (Kurabo) was used. Subsequently, the medium was replaced with a sample culture solution prepared at each concentration using HuMedia-KB2 (manufactured by Kurabo Industries) medium, and further cultured for 48 hours. Each sample culture solution was prepared so that the final ethanol concentration was 1%.
  • the cell activation effect evaluation results in the epidermal keratinocytes are shown in FIG. 1 as relative values [Index (%)] with the cell activation effect in the blank with no sample taken as 100. No significant epidermal cell activation effect was observed in the blank ethanol 1% and the soymilk extract of Comparative Example 1 (non-fermented), whereas in the soymilk fermented extract of Example 1-1, L. delbrueckii subsp. lactis JCM 1105 and L. delbrueckii subsp. In both samples fermented with lactis JCM 1148, a significant cell activating effect was observed at 124%. Further, the hypocotyl fermented extract of Example 2 is also described in L. delbrueckii subsp.
  • Test Example 2 Evaluation of cell activation effect of fermented extract in skin fibroblasts For the same sample as in Test Example 1, the cell activation action in skin fibroblasts was evaluated by the method shown below. All samples were adjusted to pH 7.4 ⁇ 0.05 using 1N sodium hydroxide, and then sterilized by filtration with a 0.20 ⁇ m filter.
  • Normal human skin fibroblasts [manufactured by Kurabo Industries, product name NHDF (NB)] are seeded in a 96-well microplate so as to be 2 ⁇ 10 3 cells per well, at 37 ° C. in a carbon dioxide concentration of 5 vol%. Cultured for 48 hours. As the seeding medium, 10% FBS-containing DMEM medium (manufactured by Life Technology) was used. Subsequently, it replaced
  • the number of viable cells was measured using Cell Counting Kit-8 (manufactured by Dojin Chemical).
  • 10% FBS-containing DMEM medium was used as a positive control, and 1% ethanol-containing FBS-free DMEM medium was used as a blank for each sample.
  • the cell activation effect evaluation results in skin fibroblasts are shown in FIG. 2 as relative values [Index (%)] with the cell activation effect in the blank with no sample taken as 100.
  • 1% ethanol as a blank and the soymilk extract of Comparative Example 1 (non-fermented) no dermal fibroblast activation effect was observed, whereas in the soymilk fermented extract of Example 1-1, L. delbrueckii subsp.
  • lactis JCM 1105 113%. delbrueckii subsp.
  • a significant cell activation effect was observed at 117%, and a tendency for the action to be enhanced by fermentation was observed.
  • hypocotyl fermented extract of Example 2 is also described in L.P. delbrueckii subsp.
  • L. delbrueckii subsp L. delbrueckii subsp.
  • lactis JCM 1148 a strong cell activation effect was observed at 137%, and the effect of the hypocotyl fermented extract was higher than that of the fermented soymilk extract of Example 1-1.
  • FIG. 2 it was confirmed that the fermented extract of the present invention has a very strong cell activation effect on normal human skin fibroblasts.
  • DPPH radical elimination rate ⁇ 1 ⁇ (B) / (A) ⁇ ⁇ 100 Trolox was used as a positive control having an antioxidant effect, and 50% ethanol was used as a blank for each sample.
  • the evaluation results of antioxidant action are shown in FIG.
  • the DPPH radical scavenging activity in the soymilk extract of Comparative Example 1 (non-fermented) was 54%, whereas in the soymilk fermented extract of Example 1-1, L. delbrueckii subsp. 76% for the sample fermented with lactis JCM 1105; delbrueckii subsp.
  • a DPPH radical scavenging activity as high as 69% was observed, and a tendency to enhance the action by fermentation was recognized.
  • the DPPH radical scavenging activity in the hypocotyl extract (non-fermented) of Comparative Example 2 was 77%, whereas in the hypocotyl fermented extract of Example 2, L. delbrueckii subsp. In the sample fermented with lactis JCM 1105, L. delbrueckii subsp. In the sample fermented with lactis JCM 1148, an extremely high DPPH radical scavenging activity of 80% was observed, and a tendency for the action to be enhanced by fermentation was observed. The effect of the hypocotyl fermented extract was higher than that of the fermented soymilk extract of Example 1-1.
  • the results of evaluating the antioxidant activity of the isoflavone preparation by the same method are shown in FIG.
  • a high DPPH radical scavenging activity was not observed even in the 200 ⁇ M isoflavone preparation, which is more than the isoflavone contained in the fermented soymilk fermented with lactis JCM 1148. From this, it was considered that most of the DPPH radical scavenging activity of the fermented extract was exhibited by active ingredients other than isoflavones. Therefore, the fermented extract of the present invention contains a component having high antioxidant ability other than isoflavone in addition to isoflavone widely known as an antioxidant substance, and exhibits a very strong antioxidant action. Was confirmed.
  • Test Example 4 Evaluation of anti-glycation effect of fermented extract About the same sample as Test Example 3, the anti-glycation effect was evaluated by the method shown below. All samples were adjusted to pH 7.4 ⁇ 0.05 using 1N sodium hydroxide, and then sterilized by filtration with a 0.20 ⁇ m filter.
  • the test solution was dispensed into a 96-well plate, and fluorescence was measured at an excitation wavelength of 370 nm and a fluorescence wavelength of 440 nm.
  • the fluorescence in the case of sample addition is (A)
  • the fluorescence of the reaction blank is (B)
  • the fluorescence of the positive control is (C)
  • the fluorescence of the positive control blank is (D)
  • the AGEs production inhibitory activity is Defined.
  • AGEs production inhibitory activity ⁇ 1- (AB) / (CD) ⁇ ⁇ 100
  • aminoguanidine was used as a positive control having AGEs production inhibitory activity.
  • the anti-glycation effect evaluation results of the fermented extract are shown in FIG.
  • the AGEs production inhibitory activity of the soymilk extract of Comparative Example 1 (non-fermented) was 17%, whereas the soymilk fermented extract of Example 1-1 had L. delbrueckii subsp. 30% for the sample fermented with lactis JCM 1105; delbrueckii subsp.
  • a high AGEs production inhibitory activity of 36% was observed, and a tendency for the action to be enhanced by fermentation was observed.
  • the AGEs production inhibitory activity in the hypocotyl extract (non-fermented) of Comparative Example 2 was 81%, whereas in the hypocotyl fermented extract of Example 2, L. delbrueckii subsp. lactis JCM 1105 and L. delbrueckii subsp. Both samples fermented with lactis JCM 1148 showed a very high AGEs production inhibitory activity of 100%, and a tendency for the action to be enhanced by fermentation was observed, similar to the fermented soymilk extract. The effect of the hypocotyl fermented extract was higher than that of the fermented soymilk extract of Example 1-1.
  • the anti-glycation effect of the fermented soymilk extract may have a synergistic effect due to the combination of isoflavones, or may be exhibited by an active ingredient other than isoflavones.
  • the anti-glycation action of the hypocotyl fermented extract shown in FIG. 5 may be mainly exerted by glycitein. It was.
  • Normal human epidermal keratinocytes [manufactured by Kurabo Industries, product name NHEK (NB)] are seeded in a 96-well microplate so as to be 10 ⁇ 10 3 cells per well, at 37 ° C. in a carbon dioxide concentration of 5 vol%. Cultured for 24 hours. As the seeding medium, HuMedia-KG2 medium (Kurabo) was used. Subsequently, the medium was replaced with a sample culture solution prepared at each concentration using HuMedia-KB2 (Kurabo) medium, and further cultured for 24 hours. Each sample culture solution was prepared so that the final ethanol concentration was 1%.
  • tert-butyl hydroxide (t-BHP) was exposed to a final concentration of 0.5 mM and cultured for 2 hours. Next, each well was thoroughly washed with HBSS ( ⁇ ), and further cultured in HuMedia-KB2 medium for 22 hours.
  • FIG. 7 shows the evaluation results of the antioxidant effect (cytoprotective action).
  • the cell viability of the soymilk extract (non-fermented) of Comparative Example 1 was 14%, whereas the fermented soymilk extract of Example 1-1 had a high cell viability of 48%. A tendency to enhance the protective effect was observed. As is clear from FIG. 7, it was confirmed that the fermented soymilk extract of the present invention has a very strong antioxidant effect.
  • Example 6 Evaluation of moisturizing action of fermented soymilk extract Among the fermented soymilk extracts prepared in Example 1-1, L. delbrueckii subsp. About the soymilk fermented extract prepared using lactis JCM 1148, the moisturizing effect in human in vivo was evaluated by the method shown below. All samples were adjusted to pH 7.4 ⁇ 0.05 using 1N sodium hydroxide, and then sterilized by filtration with a 0.20 ⁇ m filter.
  • the test site of 3 cm square was taken on the inner side of the forearm of the subject, and the test sample was applied 3 times a day for 3 days.
  • the stratum corneum moisture content and transdermal moisture transpiration were measured 8 to 10 hours after the final application of the test sample.
  • a highly sensitive stratum corneum film thickness / moisture meter ASA-MX3 was used for the measurement of the stratum corneum moisture content
  • Vaposcan AS-VT100RS both manufactured by Asahi Biomed Co., Ltd. was used for the measurement of the transdermal moisture transpiration amount.
  • FIGS. The results of evaluating the moisturizing effect of the fermented soymilk extract are shown in FIGS.
  • the stratum corneum moisture content increased by 10% or more by application of the soymilk fermented extract-containing lotion.
  • the tendency for the transdermal moisture transpiration amount to decrease by 10% or more by application of the soymilk fermented extract-containing lotion was observed. From this, it was confirmed that the fermented soymilk extract has a stratum corneum moisture content increasing action and a stratum corneum barrier function enhancing action, and exerts a moisturizing action in human in vivo.
  • a soymilk fermented extract containing a high content of isoflavone aglycone and polyamine and in particular, it has a low sugar content and has a cell activation effect and an antioxidant effect on epidermal keratinocytes and skin fibroblasts.
  • the fermented soymilk extract exhibiting anti-aging effects such as anti-glycation action and moisturizing action can be provided.
  • a hypocotyl fermented extract obtained by fermenting soybean hypocotyls with lactic acid bacteria can be provided, in particular, high content of isoflavone aglycone and polyamine, and epidermal keratinocytes and skin fibers.
  • hypocotyl fermented extract having an anti-aging action such as a cell activation action, an antioxidant action and an anti-glycation action on blast cells.
  • the soymilk fermented extract and hypocotyl fermented extract of the present invention have industrial applicability in the fields of cosmetics, pharmaceuticals, and foods and drinks.

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Abstract

La présente invention a pour but de proposer des extraits fermentés qui sont utiles comme matière de départ pour des produits cosmétiques, des médicaments, des aliments, des boissons, etc. Un extrait de lait de soja fermenté ou un extrait d'hypocotyle fermenté qui contient des isoflavone aglycones et des polyamines et a un ou plusieurs effets antivieillissement tels qu'un effet d'activation de kératinocyte épidermique, un effet d'activation de fibroblaste dermique, un effet anti-oxydant et un effet anti-diastatique, ledit extrait fermenté étant obtenu par un procédé qui comprend une étape de fermentation de lait de soja ou d'hypocotyle de soja à l'aide d'une bactérie d'acide lactique, une étape de mélange du produit de fermentation ainsi obtenu avec un solvant organique et une étape d'élimination de matières solides de celui-ci.
PCT/JP2013/082603 2012-12-11 2013-12-04 Extrait de lait de soja fermenté et extrait d'hypocotyle fermenté WO2014091988A1 (fr)

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JP2015209423A (ja) * 2014-04-30 2015-11-24 学校法人同志社 イソフラボンアグリコン又はイソフラバノンアグリコンを含有する抗糖化剤
JP2016123395A (ja) * 2015-01-08 2016-07-11 学校法人加計学園 テンペ発酵物の製造方法
JP2016169206A (ja) * 2015-03-09 2016-09-23 御木本製薬株式会社 皮膚外用剤、しわ改善促進剤、たるみ改善促進剤、マトリックスメタロプロテアーゼ遺伝子発現阻害剤。
JP2017155029A (ja) * 2016-03-02 2017-09-07 株式会社ピカソ美化学研究所 豆乳発酵物
JP2018186751A (ja) * 2017-05-02 2018-11-29 有限会社花立山農業研究所 大豆発酵食品、及び大豆発酵食品の製造方法
CN112804886A (zh) * 2018-08-08 2021-05-14 株式会社明治 植物化学物质吸收促进用组合物
WO2020032100A1 (fr) * 2018-08-08 2020-02-13 株式会社明治 Composition favorisant l'absorption de substances phytochimiques
US20210299194A1 (en) * 2018-08-08 2021-09-30 Meiji Co., Ltd. Composition for promoting absorption of phytochemicals
US11684644B2 (en) * 2018-08-08 2023-06-27 Meiji Co., Ltd. Composition for promoting absorption of phytochemicals
CN112804886B (zh) * 2018-08-08 2024-02-06 株式会社明治 植物化学物质吸收促进用组合物
JP2020100574A (ja) * 2018-12-20 2020-07-02 株式会社光英科学研究所 皮膚用保湿機能剤
JP7179328B2 (ja) 2018-12-20 2022-11-29 株式会社光英科学研究所 経口投与用の皮膚用保湿機能剤
KR20200099308A (ko) * 2019-02-14 2020-08-24 강원대학교산학협력단 대두 배아를 이용한 폴리아민 고함유 발효물의 제조 방법
KR102288725B1 (ko) 2019-02-14 2021-08-11 강원대학교산학협력단 대두 배아를 이용한 폴리아민 고함유 발효물의 제조 방법
JP2021075504A (ja) * 2019-11-13 2021-05-20 東洋紡株式会社 抗糖化剤
JP7476517B2 (ja) 2019-11-13 2024-05-01 東洋紡株式会社 抗糖化剤

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