KR101773348B1 - New compounds isolated from chestnut honey and antioxidant composition comprising the chestnut honey extract or fraction comprising the same - Google Patents
New compounds isolated from chestnut honey and antioxidant composition comprising the chestnut honey extract or fraction comprising the same Download PDFInfo
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- KR101773348B1 KR101773348B1 KR1020150136881A KR20150136881A KR101773348B1 KR 101773348 B1 KR101773348 B1 KR 101773348B1 KR 1020150136881 A KR1020150136881 A KR 1020150136881A KR 20150136881 A KR20150136881 A KR 20150136881A KR 101773348 B1 KR101773348 B1 KR 101773348B1
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Images
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
- 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
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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
- 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
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- 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
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
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- 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
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2200/00—Function of food ingredients
- A23V2200/30—Foods, ingredients or supplements having a functional effect on health
Abstract
The present invention relates to an antioxidative composition comprising as an active ingredient, a novel compound isolated from a honey, and a honey extract or a fraction thereof containing the same.
The present invention provides a novel compound having antioxidative activity isolated from the honey, or the present invention is also characterized by providing an antioxidative food composition or a cosmetic composition comprising as an active ingredient an extract of Bream containing the compound or a fraction thereof .
According to the present invention, it is possible to isolate new compounds from domestic honey to thereby reveal the functional characteristics of domestic honey, to enable physiological activity test for new substances, and to use as a marker for confirming the origin of domestic honey There is provided an antioxidative composition comprising as an active ingredient a novel compound and a honey extract or a fraction thereof separated therefrom.
Description
The present invention relates to an antioxidative composition comprising as an active ingredient, a novel compound isolated from a honey and a honey extract or a fraction thereof containing the same, and more particularly to a composition for antioxidation comprising three kinds of novel compounds having antioxidative activity Castanea crenata Sieb) extract or a fraction thereof as an active ingredient.
Honey is collected by honey bees collected from flowers, stored in beehives, then dialed, aged sugar beetles, honey bees store the honey in the honeycomb, and several times by adding the digestive juice, This becomes fructose and glucose.
Honey is composed of 70 ~ 80% of saccharides and monosaccharides such as fructose and glucose are 36 ~ 38% and 34 ~ 36%, respectively. Honey is high in energy (3.3kcal / g) and is a natural sweetener that has been widely used around the world.
Especially honey contains a large amount of substances related to various physiological activities, so it can be said that its value as a functional food is also great. Representative functional honey is Manuka honey from New Zealand, and its research is actively carried out mainly on various functions such as antibacterial, antioxidant and anti-cancer.
Some of the factors related to the functionality of these honeys include flavonoids, phenolic acids, enzymes (glucose oxidase, catalase), vitamin C, organic acids, and amino acids.
The honey is a honey with a chestnut flower. It is collected in the middle of June, and is dark brown or black. Especially, it contains potassium, iron, and so on, and it is effective to improve the stomach and liver and it is said to be good for calming the cough. In general, honey with a dark color has high antioxidant and antioxidant activity because of high content of phenol and flavonoid.
According to the results of the research so far, it has been found that quinolinone series alkaloid substances are present in a large amount in the honey (non-patent document 1 / Beretta et al 2009, non-patent
However, few systematic studies have been conducted on the substances contained in domestic honey.
Accordingly, the inventors of the present invention have analyzed 16 alkaloid substances contained in the honey by analyzing the alkaloid substances contained in domestic honey, and three novel compounds were isolated and identified, And they confirmed that they have excellent antioxidative activity, thereby completing the present invention.
It is an object of the present invention to provide a novel compound having antioxidative activity isolated from the honey.
Another object of the present invention is to provide an antioxidative food composition or a cosmetic composition containing an extract of Bream comprising a novel compound having an antioxidative activity isolated from the honey, or a fraction thereof as an active ingredient.
It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are not intended to limit the invention to the particular embodiments that are described. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory and are not restrictive of the invention, There will be.
In order to achieve the above object, the present invention provides a novel compound having an antioxidative activity fractionally extracted from honey.
The present invention also provides an antioxidative food composition or cosmetic composition comprising as an active ingredient an extract of Bream containing the compound or a fraction thereof.
At this time, it is characterized in that the honey extract is sequentially extracted with methanol and ethanol.
The fraction is characterized by being an ethyl acetate fraction obtained by re-dissolving the above-mentioned extract of water of the present invention in water, followed by fractionation with n-hexane, ethyl acetate and n-butanol.
According to the present invention, there is provided an antioxidative food composition or cosmetic composition comprising as an active ingredient an extract of Bream or a fraction thereof having an excellent antioxidative activity.
In addition, by separating the novel compound from the fractions of the extract of the extract of the present invention, it is possible to identify the functional properties of domestic honey, to test the physiological activity of a novel substance, and to use it as a marker for confirming the origin of domestic honey .
FIG. 1 is a view showing an extraction process for isolating and purifying physiologically active substances from honey.
FIG. 2 is a view showing a solvent fractionation process of a honey extract. FIG.
FIG. 3 is a diagram showing the results of TLC analysis of each fraction after solvent fractionation of a honey extract. FIG.
(A): light irradiation at 365 nm
(B): light irradiation at 254 nm
(C): DPPH ethanol solvent spray
(D): cerium sulfate hydrate coloration
4 is a diagram showing the Amberlite XAD-2 column chromatography process of the ethyl acetate (EtOAc) fraction obtained after solvent fractionation.
FIG. 5 shows TLC analysis results after column chromatography on Amberlite XAD-2 of the ethyl acetate (EtOAc) fraction obtained after solvent fractionation.
(A): light irradiation at 365 nm
(B): light irradiation at 254 nm
Figure 6 is a diagram showing the chemical structures of 16 alkaloid substances isolated from the ethyl acetate (EtOAc) fraction obtained after solvent fractionation.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, the present invention will be described in detail, and a detailed description of known functions and configurations that may unnecessarily obscure the gist of the present invention will be omitted.
The present invention provides a composition for antioxidation comprising as an active ingredient, a novel compound isolated from a honey, and a honey extract or a fraction thereof containing the same.
The method of extracting and separating the extract of the present invention as an effective ingredient of the antioxidant composition of the present invention or its fractions will be described in detail as follows.
1. Step 1: Production of honey extract
First, domestic honey extract is extracted by solvent extraction of domestic honey.
At this time, the method for preparing the extract of the present invention is preferably warmed and extracted by reflux or extraction at room temperature, but it is not limited thereto. The number of extraction times is preferably 1 to 5 times, more preferably 3 times, but is not limited thereto.
The extract may be water, C1-C4 alcohol or a mixture thereof, more preferably C1-C4 alcohol extract, most preferably methanol and ethanol, . ≪ / RTI >
Thereafter, a method such as concentration or freeze-drying may further be carried out.
2. The second step; Production of fractions derived from chestnut honey extract
A fraction is obtained from the above-mentioned extract of the honey through a solvent fraction.
In other words, the thus-obtained extract of the honey is re-dissolved in water and then fractionated with n-hexane, ethyl acetate and n-butanol in order to obtain fractions.
TLC analysis of these fractions showed that the fractions containing the antioxidant compounds and the fractions which were easy to purify were ethyl acetate fraction.
Thus, the ethyl acetate fraction containing the highest amount of the antioxidative active substance was subjected to Amberlite XAD-2 column chromatography using water and methanol, and the fraction thus obtained was subjected to HPLC to obtain 16 kinds of alkaloid substances And the compounds of the following formulas (1) to (3) are novel compounds.
Accordingly, the present invention provides a novel compound having an antioxidative activity represented by the following general formula (1).
[Chemical Formula 1]
2,3-dihydropyrrolo [1,2-a] quinazolin-5 ( 1H ) -one
The present invention also provides a novel compound having an antioxidative activity represented by the following general formula (2).
(2)
3- (2 ' -pyrrolidinyl) -kynurenic acid
The present invention also provides a novel compound having an antioxidative activity represented by the following general formula (3).
(3)
3-dihydro-spiro [2 (1H), 3 '(1'H) -diquinoline] -3', 4,4'- trione (spirodiquinolinone)
As described above, the honey extract or the fractions thereof containing the compounds of the formulas (1) to (3) of the present invention, which are novel compounds as described above, exhibit antioxidative activity, and thus can be usefully used as an antioxidant in health functional foods and cosmetics have.
Accordingly, the present invention provides an antioxidant food composition comprising the above-mentioned extract of Bream or a fraction thereof as an active ingredient.
In addition, the extract of the present invention or a fraction thereof may be added to a health food or beverage for the purpose of preventing accumulation of active oxygen or removing active oxygen generated.
When the extract of the present invention or the fraction thereof is used as a food additive, the extract of the present invention or the fraction thereof may be used as it is or may be used together with other food or food ingredients, and may be suitably used according to a conventional method.
The amount of the active ingredient to be mixed can be suitably determined according to the intended use (prevention, health or therapeutic treatment). Generally, in the production of food or beverage, the extract of the present invention or a fraction thereof is added in an amount of not more than 10% by weight, preferably not more than 5% by weight based on the raw material. However, in the case of long-term consumption intended for health and hygiene purposes or for health control purposes, the amount may be less than the above range, and since there is no problem in terms of safety, the active ingredient may be used in an amount exceeding the above range .
There is no particular limitation on the kind of the food. Examples of the food to which the above substance can be added include dairy products including meat, sausage, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, ice cream, various soups, drinks, tea, Alcoholic beverages, and vitamin complexes, all of which include healthy foods in a conventional sense.
The health beverage composition of the present invention may contain various flavors or natural carbohydrates as an additional ingredient such as ordinary beverages. The above-mentioned natural carbohydrates are monosaccharides such as glucose and fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, and sugar alcohols such as xylitol, sorbitol and erythritol. Examples of sweeteners include natural sweeteners such as tau martin and stevia extract, synthetic sweeteners such as saccharin and aspartame, and the like. The ratio of the natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 ml of the composition of the present invention.
In addition to the above, the composition of the present invention may further contain various nutrients, vitamins, electrolytes, flavors, colorants, pectic acids and salts thereof, alginic acid and its salts, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, A carbonating agent used in a carbonated beverage, and the like. In addition, the composition of the present invention may include natural fruit juice, fruit juice beverage, and flesh for the production of vegetable beverages. These components may be used independently or in combination. The proportion of such additives is not critical, but is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.
The present invention also provides a cosmetic composition for antioxidation comprising the above-mentioned extract of Bream or a fraction thereof as an active ingredient.
The cosmetic composition of the present invention may be prepared by mixing with an external skin excipient such as water, physiological saline, glycerol, a surfactant, a moisturizer, a thickener, a chelating agent and a pigment, Depending on the method of manufacturing the cosmetic composition, it can be prepared in various forms. For example, the cosmetic composition may contain ointment, cream, softening lotion (skin), convergent lotion (lotion), emulsion, astringent, massage cream, nutritional cream, essence , A pack, a powder, a suspension, a spray or a serum, and the like.
In addition, the cosmetic composition of the present invention may contain customary adjuvants such as stabilizers, solubilizers, vitamins, pigments, and flavorings commonly used in the field of the composition. In the above composition, the content of the honey extract or its fraction may be in an amount effective to achieve an antioxidative effect, for example, 0.001 to 10% by weight based on the total weight of the composition, preferably about 0.01 to 5% %, ≪ / RTI > but is not limited thereto.
Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples. However, these Examples and Experimental Examples are for illustrative purposes only and do not limit the scope of protection of the present invention.
Example 1 Production of Bum Extract
As shown in FIG. 1, 25 L of MeOH (25 L) was added to 25.95 kg of honey, and the mixture was allowed to stand for 2 hours, followed by suction filtration (No. 2, Whatman).
Then, 21 L of MeOH was added to the lower layer, and the mixture was stirred at 4 ° C. for 24 hours. Only the upper layer was filtered again.
Subsequently, 6 L of EtOH was added to the lower layer again, and the mixture was stirred at 4 ° C for 24 hours, and then only the upper layer was filtered.
The obtained filtrate (MeOH extract and EtOH extract) were combined and concentrated using a vacuum concentrator to obtain 12.21 kg of the extract of the present invention.
The above-mentioned honey extract was dissolved in H 2 O and adjusted to 13.5 L. 13 L of the extract (11.76 kg, 25 kg wet wt. Eq.) Of honey was used as a sample of the following experiment.
Example 2: Preparation of fraction derived from chestnut honey extract
As shown in Fig. 2, a H 2 O suspension (13 L, 25 kg wet wt. Eq.) Of the honey extract (11.76 kg) prepared in Example 1 was dissolved in hexane (13 L x 3 ), Ethyl acetate (EtOAc, 13 L × 3), and water saturated butanol (BuOH, 13 L × 3) were successively subjected to solvent fractionation.
The obtained fractions were concentrated under reduced pressure and the weight was measured. As a result, an n-hexane layer (0.848 g), an EtOAc layer (48.16 g), a BuOH layer (747.864 g) and a H 2 O layer were obtained.
<Experimental Example 1> TLC analysis and antioxidant activity of fractions derived from the extract of chestnut honey
1. Experimental Method
Each of the fractions obtained in Example 2 was spotted on a TLC plate (
In addition, the cerium sulfate hydrate coloring reagent was further sprayed and then heated on a hot plate at about 150 ° C to detect a color-contained component.
2. Experimental results
As shown in FIG. 3, TLC analysis was performed on each of the fractions obtained after solvent fractionation, and the tendency of the compounds contained in each fraction was compared and analyzed.
As a result, it was confirmed that the compounds contained in the honey extract were uniformly divided into the EtOAc layer, the BuOH layer and the H 2 O layer, and only a small amount of the compounds were migrated to the n-hexane layer
As a result of examining the presence of antioxidant active compounds by spraying DPPH ethanol solution, as shown in FIG. 3C, in the case of n-hexane layer and BuOH layer, purple-colored spots were hardly shown, And the BuOH layer showed little or very small amount of compounds having antioxidant activity.
In contrast, the EtOAc layer showed higher antioxidative activity than the n-hexane layer and the BuOH layer, and the discoloration of purple color was strongly observed at Rf 0.27-0.97, suggesting that a large amount of antioxidant compounds exist.
In the H 2 O layer, violet decolorization was strong at Rf 0-0.17. It was judged that the compounds having antioxidant activity in the H 2 O layer were highly polar.
As a result of spraying the cerium sulfate hydrate coloring reagent, black spots were observed in the H 2 O layer as shown in FIG. 3D. This is probably due to the highly polar compounds of sugars and amino acids, suggesting the presence of large amounts of phenolic compounds as the black and yellow spots are observed in the EtOAc layer.
From the above results, it was determined that most of the compounds having antioxidative activity contained in the honey were transferred into the EtOAc layer and the H 2 O layer. However, in the case of the H 2 O layer, it was considered that the purification of the useful component would not be easy when the sample itself contained a large amount of sugar.
Therefore, we tried to investigate the structure of antioxidant compounds in the EtOAc layer containing many kinds of antioxidant compounds in the fraction after solvent fractionation.
Experimental Example 2 Isolation of Compound from Ethyl Acetate Fraction from Bum Extract (16 Compounds)
1. Experimental Method
34.7 g of the EtOAc fraction of Example 2 (48.16 g) was subjected to Amberlite XAD-2 column chromatography to isolate the antioxidant from the compound.
After slurrying with Amberlite XAD-2 (521 μM; Supelco, Bellefonte, PA, USA) with H 2 O and filling the column (5.0 × 84 cm, 1750 mL), the EtOAc fractions were dissolved in the same solvent After charge, H 2 O was eluted with about 3 times the bed volume of 5.2 L and the MeOH concentration was increased by 20% from 20% to 100% by step-wise elution to about 2 2.6 L of the eluate was eluted, and finally 4 L of acetone was eluted.
The eluted H 2 O solution (5.2 L) was taken as one fraction and the 20% to 80% MeOH eluate was taken as one fraction of 100 mL. 100% MeOH eluate was separated into three fractions of 900 mL and acetone eluate was separated into fractions of 1 L each.
Finally, the total fractions obtained were 113 (FIG. 4), and TLC analysis was performed for each batch.
In this TLC analysis, 113 fractions obtained after column chromatography on Amberlite XAD-2 were spotted on a TLC plate and developed with BuOH / AcOH / H 2 O = 4: 1: 2 (v / v / v) And 365 nm, respectively.
2. Experimental results
As a result of TLC analysis of each fraction obtained after column chromatography, the result was as shown in FIG. 5, and the compounds were detected at the positions where the polarity of Rf 0.12-0.35 was judged to be high by the first eluting solvent (H 2 O) It was judged that the sugar compounds contained in the bore EtOAc layer were removed with little other components.
However, the TLC trends of the eluates did not reveal the ease of grouping the eluted fractions.
Experimental Example 3 Purification by HPLC
1. Experimental Methods and Results
ODS-HPLC analysis was performed on some of the fractions in order to examine in detail the tendency of the compounds contained in each of the fractions, since the TLC trend of the eluates did not show any easy characteristics for grouping the elution fractions.
At this time, a total of 113 fractions finally obtained were grouped into 9 groups based on the TLC analysis of FIG. 5, and the fractions were named EL-G0 to G9 as shown in Table 1 below.
Semi-preparative ODS-HPLC was then used to isolate the alkaloid material from the fraction G3 (H 2 O / MeOH, 6: 4, v / v, 248.4 mg) The column was eluted with 5% MeCN (pH 2.65 by TFA, eluent A) and 60% MeCN (pH 2.65 by TFA, eluent B) using a shim-pack PREP-ODS (H) KIT column (20> 250 mm, Shimadzu) Gradient elution with 17% B for 30 min and 100% B for 45 min.
As a result, the mixture G3a ( tR 22.8 min, 5.2 mg), compound 2 ( tR 28.2 min, 9.1 mg), a mixture of
The column was eluted with 2% MeCN (pH 2.65 by TFA, 92 eluent C) and 40% MeCN (pH 2.65 by TFA, eluent D) using a shim-pack PREP-ODS (H) KIT column (20> 250 mm, Shimadzu) ) With a gradient of 17% D for 30 min.
The fraction G8 (H 2 O / MeOH, 2: 8, v / v, 1216.2 mg) was dissolved in 100 ml of water and fractionated with CHCl 3 (3 L, 3 ×) to obtain G8-C (CHCl 3 layer, 779.4 mg). Fraction G8-C (779.4 mg) was isolated using semi-preparative ODS-HPLC. Likewise, gradient elution was carried out between 30% MeOH (eluent E) and 70% MeOH (eluent F) for 30 min at 100% F to yield compound 7 ( tR 17.2 min, 4.0 mg), 8 ( tR 19.7 min, 7.6 mg), 9 ( tR 21.0 min, 75.0 mg), 10 ( tR 23.0 min, 67.5 mg), G8-C7 ( tR 24.7 min, 16.7 mg), G8-C8 ( tR 27.1 min, 20.2 mg) and G8-C9 ( tR 29.4 min, 32.1 mg). Next, semi-preparative ODS-HPLC was performed using 20% MeCN (pH 2.65 by TFA, eluent G) and 40% MeCN (eluent H), and eluted with 100% H for 30 min and maintained at 100% H for 60 min ( TR 24.2 min, 1.1 mg), 12 ( tR 27.7 min, 3.0 mg), and 13 ( tR 29.5 min, 1.0 mg) from G8-C7 (16.7 mg), 14 ( tR 19.4 min, 1.1 mg) and 15 ( tR 26.8 min, 1.6 mg) from G8-C8 (20.2 mg), and 16 ( tR 31.4 min, 1.6 mg).
<Experimental Example 3> Structural analysis of isolated alkaloid materials
The structures of the sixteen isolated alkaloid substances are as shown in FIG. 6, of which 13 are known compounds, and these 13 known compounds can be identified easily from NMR and MS analyzers.
Therefore, three kinds of
1)
For the structural analysis of
1 sp 2 carbon proton signals of the four species in the H NMR spectrum [б 8.48 (1H , d, J = 7.8 Hz, H-5), 7.42 (1H, t, J = 7.8 Hz, H-6), 7.71 ( (1H, t, J = 7.8 Hz, H-7), 7.83 (1H, d, J = 7.8 Hz, H-8).
In addition to the three kinds of methylene carbon proton signal [4.02 (2H, t, J = 8.0 Hz, H-1 '), 1.89 (2H, m, H-2'), 2.96 (2H, t, J = 7.0 Hz, H 3 ')] were detected, and 13 carbon signals contained 8 sp 2 carbons via 13 C NMR, 4 quaternary carbons at б 175.9-121.8 and three
As a result, it was confirmed that quinazolinone was bonded to the propane moiety and was determined to be 2,3-dihydropyrrolo [1,2-a] quinazolin-5 (1H) -one. This compound has been artificially synthesized and published by other researchers, but this is the first time it has been found in nature.
2)
Molecular weight peaks m / z 293.1 [M + H] + and 315.1 [M + Na] + were observed in the ESI-MS (positive) spectrum and the molecular weight of the
Eight kinds of sp 2 carbon proton signals were detected in the 1 H NMR spectrum, and it was found that the benzene ring with the second substituent was present at δ 8.15-6.75.
In addition, one methyl proton signal [δ 3.76 (1H, d, J = 13.5 Hz, H-3a) and 3.59 The signal [僚 8.52 (1H, s, H-1), 12.26 (1H, s, H-1 ')] was detected.
13 C NMR showed that the moieties with the second substituent benzene ring were bonded to carbon number 12 [149.6-114.7].
3 carbonyl carbon [б 189.5 (C-4), 169.8 (C-2 '), and 191.3 (C-3')] and one quaternary sp3 carbon [б 68.0 (C-2), 149.6 (C-8a), 141.0 (C-8), and carbon black d 68.0 (C-2)].
Based on the MS and 1D-NMR results, the skeleton of
From the results of 1 H- 1 H COZY (bold lines) and HMBC (arrows) spectra,
3)
The molecular weight of
1 H NMR results confirm that there are four 1,2-substituted benzene rings [б 8.32-7.46].
In addition, one methyline proton signal [δ 4.46 (1H, dd, J = 11.8, 3.8 Hz, H-2 ") was observed and four methylene proton signals were observed [б 4.37-1.09].
According to 13 C NMR results, ten sp2 carbons signals, six quaternary substitution carbon signals [б 176.3-120.5] and five SP3 carbon signals [б 58.9-24.2] were detected.
Three of the six sp2 carbons signals were nitrogen-bearing carbons [162.6 (C-2), 143.0 (C-2), and 141.9 (C-8a)], two carbonyl carbons [б 176.3 -4) and 162.6 (C-2 ').
These results suggest that the compound is 3- (2'-pyrrolidinyl) -kynurenic acid.
≪ Formulation Example 1: Preparation of cosmetic &
Using the ethyl acetate fraction derived from the honey extract prepared in Example 2 as an active ingredient, the essence was prepared in the following composition.
[Furtherance]
10 mg of the active ingredient on the basis of the total weight, 3.0 mg of glycerin, 0.05 mg of EDTA, 0.04 mg of benzophenone-9, 0.2 mg of carboxyvinyl polymer, 0.18 mg of triethanolamine, 0.6 mg of oxydoteth-25, 1.0 mg of glyceryl monostearate , Preservative 0.01 mg, perfume 0.01 mg, purified water balance
≪ Preparation Example 2: Preparation of Ointment Agent >
Using the ethyl acetate fraction derived from the honey extract prepared in Example 2 as an active ingredient, the essence was prepared in the following composition.
[Furtherance]
60% by weight of hydrogenated castor oil, 0.5% by weight of sorbitan sesquioleate, 5.0% by weight of petroleum jelly, 5.0% by weight of liquid paraffin, 10.0 wt%
≪ Formulation Example 3: Preparation of health food &
Using the ethyl acetate fraction derived from the honey extract prepared in Example 2 as an active ingredient, a health drink was produced in the following composition.
2 mg of inositol hydrochloride, 50 mg of orthoacid, 0.48 to 1.28 mg of active ingredient, and 200 ml of water were added to a solution of 5 mg of honey, 5 mg of chitosanamide, 10 mg of nicotinic acid amide, 3 mg of riboflavin sodium chloride,
A beverage was prepared using the above-mentioned composition and content by a conventional method.
≪ Formulation Example 3: Preparation of flour food &
0.5 to 5 parts by weight of the ethyl acetate fraction derived from the honey extract prepared in Example 2 according to the present invention was added to 100 parts by weight of wheat flour, and bread, cake, cookies, crackers and noodles were prepared using the mixture, .
It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the inventions. You can implement the examples. The scope of the present invention is defined by the appended claims, and all differences within the scope of the claims are to be construed as being included in the present invention.
Claims (11)
(2)
(3)
Lt; / RTI > is extracted fractionally from the honey.
Lt; / RTI > antioxidant activity.
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| KR102535211B1 (en) * | 2021-11-23 | 2023-05-26 | 주식회사 케뎀 | Composition for gastrointestinal protection comprising chestnut honey extract and cabbage juice and manufacturing method thereof |
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- 2015-09-25 KR KR1020150136881A patent/KR101773348B1/en active IP Right Grant
Non-Patent Citations (2)
| Title |
|---|
| Adv. Synth. Catal. 2013, 355, 2179-2184. |
| Journal of Food Biochemistry, 2009, 33, 470-481. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102535211B1 (en) * | 2021-11-23 | 2023-05-26 | 주식회사 케뎀 | Composition for gastrointestinal protection comprising chestnut honey extract and cabbage juice and manufacturing method thereof |
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