JP2004267155A - Food and drink, pharmaceutical, arteriosclerosis preventive, and agent for suppressing oxidative denaturation of ldl - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a food and drink (health food), a pharmaceutical, an arteriosclerosis preventing agent and an agent for suppressing oxidative denaturation of LDL capable of effectively suppressing the oxidative denaturation of LDL (low-density lipoprotein) in blood. <P>SOLUTION: The food and drink, pharmaceutical, arteriosclerosis preventing agent and agent for suppressing oxidative denaturation of LDL contain a flavonoid aglycone derived from lemon as an active component. Examples of the flavonoid aglycone are eriodictyol and diosmetin. These flavonoid aglycones can be produced by converting flavonoid glycosides derived from lemon into aglycone. The aglyconization is carried out e.g. by β-glucosidase treatment or microbial fermentation with microorganisms of the genus Aspergillus. <P>COPYRIGHT: (C)2004,JPO&NCIPI

Description

[0001]
TECHNICAL FIELD OF THE INVENTION
The present invention relates to foods and drinks, pharmaceuticals, arteriosclerosis preventive agents and LDL which can be used for prevention or treatment of arteriosclerosis or the like by suppressing oxidative degeneration of low density lipoprotein (LDL) in blood. It relates to an oxidation denaturation inhibitor. More specifically, foods and drinks (health foods), pharmaceuticals, and prevention of arteriosclerosis containing a flavonoid aglycone as an active ingredient, which has an effect of rapidly and efficiently suppressing the oxidative denaturation of LDL in vivo and in vitro. And LDL oxidative denaturation inhibitors.
[0002]
[Prior art]
Hitherto, it has been reported that when a healthy person ingests lemon juice, a high antioxidant effect on LDL is exhibited (see Non-Patent Document 1). This report reported that 12 healthy male subjects were ingested 500 ml of lemon juice squeezed with a juicer or the same amount of vitamin C as 500 ml of lemon juice after fasting overnight, before ingestion, 1,2,4 ingestion. After an hour, blood is collected, and the antioxidant ability of LDL is measured by the conjugated diene method using an azo compound. As a result, in the lemon juice, an increase in antioxidant ability against LDL was significantly observed 1 hour after ingestion, but no significant difference was observed in vitamin C. Furthermore, it has been reported that almost similar results were obtained in in vitro tests. That is, this report strongly suggested that not the vitamin C in the lemon juice, but a flavonoid (glycoside) specific to lemon such as eriocitrin greatly contributed to the increase in the antioxidant ability. is there. On the other hand, Patent Document 1 discloses an apoptosis inducer containing at least one of eriocitrin, eriodictyol, 3,4-dihydroxyhydrocinamic acid, and phloroglucinol as an active ingredient, and a medicament containing the apoptosis inducer Compositions and health foods and drinks are disclosed.
[0003]
[Patent Document 1]
JP 2001-199881 A
[Non-patent document 1]
Chika Sakurai et al., Examination of antioxidant activity of lemon juice against human LDL, "Abstracts of the 56th Annual Meeting of the Japan Society of Nutrition and Food Science", Japan Society of Nutrition and Food Science, June 20, 2002, p. 358.
[0004]
[Problems to be solved by the invention]
However, although the antioxidant effect of LDL by the lemon juice has shown a statistically significant increase, it is still insufficient. In addition, flavonoids such as eriocitrin, which are considered to be active ingredients in lemon juice, exist in the form of glycosides, and a more efficient method has been required from the viewpoint of absorbability in the body. On the other hand, the pharmaceutical composition and the health food or beverage described in Patent Document 1 have an effect of inducing the apoptosis of the active ingredient.
[0005]
The present invention has been made by paying attention to the problems existing in the prior art as described above. It is an object of the present invention to provide foods and drinks, pharmaceuticals, arteriosclerosis preventive agents and LDL oxidation degeneration inhibitors that can effectively suppress oxidative denaturation of low-density lipoprotein in blood.
[0006]
[Means for Solving the Problems]
In order to achieve the above object, the food or drink of the invention according to claim 1 is a food or drink containing eriodictyol and / or diosmetin, and has an effect of suppressing oxidative denaturation of low-density lipoprotein in blood. Which is characterized by having
[0007]
The food or drink of the invention according to claim 2 is a food or drink containing a flavonoid aglycone derived from lemon, wherein the flavonoid aglycone is obtained through a step of aglyconizing a flavonoid glycoside derived from lemon. It is characterized by having.
[0008]
The food or drink according to the third aspect of the present invention is characterized in that, in the second aspect, the food or beverage has an action of suppressing oxidative denaturation of low-density lipoprotein in blood.
[0009]
The food and drink of the invention according to claim 4 is characterized in that, in the invention according to claim 2 or 3, the aglyconization treatment is glycosidase treatment or microbial fermentation treatment with a microorganism of the genus Aspergillus. .
[0010]
The medicament of the invention according to claim 5 is a medicament containing eriodictiol and / or diosmetin as an active ingredient, and has an action of suppressing oxidative denaturation of low-density lipoprotein in blood. Things.
[0011]
The arteriosclerosis preventive agent of the invention according to claim 6 is an arteriosclerosis preventive agent containing eriodictyol and / or diosmetin as an active ingredient, and is used for the purpose of preventing arteriosclerosis. Is what you do.
[0012]
The LDL oxidation degeneration inhibitor according to the invention of claim 7 is an LDL oxidation degeneration inhibitor containing eriodictyol and / or diosmetin as an active ingredient, and suppresses the oxidative degeneration of low-density lipoprotein in blood. It is characterized by having the action to perform.
[0013]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, embodiments embodying the present invention will be described in detail.
The food or drink (health food) of the embodiment contains a flavonoid aglycone (hereinafter, referred to as aglycone) derived from lemon fruit as an active ingredient. This food or drink exerts a particularly high antioxidant effect on blood LDL, and also contains the active ingredient having excellent absorbability in the body, so that it suppresses oxidative degeneration of ingested human blood LDL. It is possible to effectively prevent arteriosclerosis.
[0014]
The food or drink is mainly produced by a first production method which is produced through a step of adding the aglycone to a beverage or food, or a material containing a glycoside of the aglycone (flavonoid glycoside) (such as lemon fruit). ) Is subjected to an aglyconization treatment (microbial fermentation or enzyme treatment) by the second production method. Examples of the aglycone to be added in the first production method include a commercially available product, an organically synthesized product, a product obtained by extracting, purifying, and isolating a lemon fruit or a component thereof from an aglycone-treated product. However, it is most preferably obtained from a lemon fruit because mass production is easy at low cost. That is, both the first and second production methods include a step of intentionally containing aglycone.
[0015]
In the first and second manufacturing methods, another processing step other than the above steps may be performed. For example, it can also be manufactured by adding processing steps such as dilution, concentration, and powdering, or by adding the food or drink obtained by the second manufacturing method to another beverage or food. Examples of the beverage or food include sports drinks, tea drinks, tea leaves, herbs, dairy products such as milk and yogurt, foods containing gelling agents such as pectin and carrageenan, excipients such as lactose and dextrin, flavors, and sweetness. And oils and fats. When used as a preparation (health food), it may be in the form of tablets, powders, granules, capsules, syrups, candies, and the like.
[0016]
Examples of the aglycone include eriodictyol, diosmetin, and the like. The active ingredient is a component that functions to suppress the oxidative denaturation of LDL, and one or both of the two types of aglycone are suitably used. That is, both aglycones were confirmed to have high antioxidant activity in in vitro tests, and it was also confirmed that both aglycones significantly improved in vivo absorption compared to glycosides with sugar chains. Therefore, both aglycones can exhibit the function as an active ingredient. Furthermore, of these two types of aglycones, eriodictiol, which has been confirmed to exhibit the highest antioxidant action (similar to α-tocopherol) in the above test, is contained as an active ingredient. preferable.
[0017]
The aglycone is obtained by subjecting a flavonoid glycoside contained in a lemon fruit or a raw material composed of components of the lemon fruit to an aglyconization treatment. The flavonoid glycoside has a structure in which aglycone and sugar are linked by a glycosidic bond. That is, the aglycone is generated (released) by an enzyme reaction (glycosidase reaction) that cleaves a glycosidic bond of the flavonoid glycoside. At this time, sugar is also generated (released) as a by-product of the enzymatic reaction.
[0018]
The constituents of the lemon fruit include fruit juice, pericarp (albedo, flavedo), carbohydrate membrane, and sorghum. As the raw material, it is most preferable to use a squeezed residue obtained by squeezing fruit juice from the lemon fruit, since the time and effort required for production can be saved and the effective use of the lemon fruit can be easily achieved. The juice residue contains lemon peel (albedo and flavedo), a carcass membrane, a portion of the sap, and a very small amount of lemon juice that could not be squeezed.
[0019]
Examples of the flavonoid glycoside include eriocitrin, which is a glycoside of eriodictiol and rutinose (L-rhamnosyl-D-glucose), and diosmin, which is a glycoside of diosmetin and rutinose. 6,8-di-C-β-glucosyldiosmin (DGD), which is a glycoside of diosmetin and glucose, and 6 which is a glycoside of diosmetin and glucose -C-β-glucosyldiosmin (6-C-β-glucosyldiosmin; GD) and the like. These flavonoid glycosides are contained in a large amount in a juice residue obtained by squeezing fruit juice from lemon fruit among constituents of lemon fruit. In addition, the eriocitrin is contained in a larger amount in lemon than other citrus fruits.
[0020]
Examples of the aglyconization treatment include a glycosidase treatment and a microorganism fermentation treatment using a microorganism of the genus Aspergillus.
The glycosidase treatment is a treatment in which glycosidase acts on the raw material to carry out an enzymatic reaction for cleaving glycoside bonds of flavonoid glycosides contained in the raw material. As the glycosidase treatment, in order to increase the efficiency of the treatment, it is preferable to add glycosidase to the extract of the constituents of the lemon fruit other than the juice or the lemon juice to carry out the enzyme reaction. Alternatively, the enzyme reaction may be carried out by contacting the fruit juice or the extract with a carrier on which glycosidase having enzyme activity is immobilized. Glycosidases (heterosidase, β-glycosidase) are used as the glycosidase. In addition, as the lemon juice, a concentrated liquid or a diluted liquid thereof may be used. When the glycosidase is added to the raw material, the glycosidase may be inactivated or removed after the glycosidase treatment.
[0021]
The solution containing aglycone after the glycosidase treatment can be used as it is as a food or drink, or can be used as a food or drink by diluting, concentrating, or powdering (second production method). Further, the solution containing the aglycone is used as a food or drink by adding it to a beverage or a food as it is, or after performing a processing step such as dilution, concentration or drying, or extraction of the aglycone, purification or After isolation, it can be used as a food or beverage by adding it to the beverage or food (first production method).
[0022]
The microbial fermentation treatment is performed by inoculating the raw material with a microorganism of the genus Aspergillus and culturing the microorganism under a predetermined fermentation condition for a predetermined period. In this microbial fermentation treatment, aglycone is liberated from flavonoid glycosides mainly by glucosidase (β-glucosidase) produced by the vegetative hypha of the microorganism. Examples of the microorganisms include Aspergillus saitoi, Aspergillus niger, Aspergillus awageri, and Aspergillus oryzae, or Aspergillus oryzae or A. Aspergillus tamarii and other Aspergillus tamarii and the like.
[0023]
As a method of inoculating the microorganism with the raw material, spores of the microorganism can be directly sprinkled on the raw material and adhered. Further, after performing a preliminary culture process of shaking culture of the medium containing the microorganisms in advance under aerobic conditions, the medium after the preliminary culture process is sprinkled and attached so as to spread over the entire raw material, or after the preliminary culture, It is also possible to inoculate by immersing the raw material in the medium. Of these inoculation methods, it is most preferable to sprinkle the medium after the preliminary culture treatment onto the raw material since the microorganism fermentation treatment proceeds relatively uniformly.
[0024]
The pre-culture treatment is performed in order to advance the microorganism fermentation treatment quickly and smoothly by sufficiently growing and activating the microorganisms used in the microorganism fermentation treatment in advance. This pre-culture treatment is carried out under aerobic conditions at 20 to 40 ° C. for at least 5 days or more, and preferably until the mycelium of the microorganism covers about 1/3 of the medium surface. As the medium, a medium for fungi such as a potato dextrose-containing medium or a Zapec medium or various liquid mediums containing organic substances such as okara are suitably used. Further, in this preliminary culture treatment, it is preferable to adjust the pH of the medium at the start of the culture to 3 to 7 in order to improve the growth of the microorganism. The shaking speed for the shaking culture is preferably 50 rpm or more, more preferably 50 to 200 rpm. If the shaking speed is less than 50 rpm, the mycelium cannot be sufficiently grown because the entire medium containing the microorganism is not aerobic. On the other hand, when the shaking speed exceeds 200 rpm, the shaking of the culture medium is so severe that the formation of cells of the microorganism may be suppressed.
[0025]
As the microbial fermentation treatment conditions when inoculating the microorganisms activated by the pre-culture treatment to the raw material, the microorganism fermentation treatment can be easily performed under aerobic conditions, for example, it is formed in a bottomed cylindrical shape. A culture vessel having a wide bottom and a shallow depth, such as a culture dish, is preferably used. Further, it is preferable to place the raw material uniformly on the bottom of the culture vessel. The fermentation temperature is preferably 10 to 40 ° C, more preferably 20 to 40 ° C, as conditions suitable for the growth of the microorganism. In addition, as a condition suitable for the growth of the microorganism, it is preferable to perform a microorganism fermentation treatment in a dark place.
[0026]
The fermentation period for obtaining a large amount of the aglycone is preferably 2 to 12 days, more preferably 2 to 8 days, and still more preferably 3 to 7 days. When the fermentation period is less than 2 days, a sufficient amount of aglycone is not produced because the microorganism fermentation by the microorganism hardly progresses. On the other hand, when the time exceeds 12 days, the decomposition or hydroxylation reaction of the generated aglycone may proceed.
[0027]
The fermented product obtained by the above-described microbial fermentation treatment is in a state in which the decomposition of the fiber proceeds by fermentation and is very brittle and easily collapsed. In this fermented product, solids such as unfermented raw materials having insufficient fibrous degradation during fermentation and mycelia of inoculated strains formed during fermentation are present. Compared to the previous raw material, the volume is about 1/10.
[0028]
This fermented product can be used as it is as a food or drink, or can be used as a food or drink by diluting, concentrating, or pulverizing it (second production method). The fermented product can be used as a food or drink by adding it to a beverage or food after being subjected to processing steps such as dilution, concentration, or drying (first production method). The fermented product can be used as a food or drink by extracting, purifying, or isolating aglycone and then adding it to a beverage or food (first production method).
[0029]
In purifying the active ingredient in the fermented product, first, a solid content removal treatment for removing solid content mainly from the inoculum and the unfermented raw material is performed. The solid content removal treatment is performed by immersing the fermented product containing the solid content in a polar solvent, extracting the active ingredient by transferring the active ingredient into the solvent, and filtering or 2,000 xg for 30 minutes using gauze or a coarse mesh. This is a process of removing the solid content by performing a slight centrifugation. The extraction conditions for extracting the fermented product in a polar solvent are preferably extracted at room temperature for 2 hours or more from the viewpoint of extraction efficiency.
[0030]
As the polar solvent, methanol, ethanol, an aqueous solution thereof, or water is suitably used. Further, lower alcohols such as butanol and isopropanol or their aqueous solutions can also be used. Further, as the polar solvent, methanol, an aqueous solution thereof or water is preferably used from an economic viewpoint when a large amount of fermented product is treated, and water is most preferably used from the viewpoint of purification cost. In addition, when the fermented product is directly added to the health food material, it is preferable to use ethanol, an aqueous solution thereof, or water. Further, in order to kill the microorganism and stop the microbial fermentation, it is preferable to use methanol, ethanol or an aqueous solution of high concentration thereof (for example, 20% by volume or more).
[0031]
Furthermore, it is also possible to carry out a fiber removal treatment for separating and removing water-soluble fiber components mainly composed of pectin contained in the fermented product after the solid content removal treatment. This fiber content removal treatment is a treatment in which the fermented product after the solid content removal treatment is centrifuged to remove water-soluble fiber components by precipitation (at the bottom of a centrifuge tube or the like). In addition, this fiber content removal treatment may be performed by centrifuging at 11,000 × g and a centrifugal force of about 20 minutes when methanol or ethanol is used as the polar solvent, and when water or an aqueous solution is used as the polar solvent. Is centrifuged with a stronger centrifugal force.
[0032]
The concentration of the active ingredient (aglycone) contained in the beverage as a food or drink is not particularly limited, but is preferably 0.05 to 30% by weight, more preferably 0.1 to 30% by weight, because the absorption rate in the body is fast and the drink is easy to drink. The content is preferably 5 to 10% by weight. The content of the active ingredient contained in foods or preparations as food or drink is not particularly limited, but is preferably 0.1 to 99% by weight, more preferably 0.5 to 90% by weight because it is easy to ingest orally. It is good. The intake of the active ingredient is preferably 500 to 5000 mg, more preferably 1000 to 3000 mg per adult day. If the daily intake of this active ingredient is less than 500 mg, oxidative degeneration of blood LDL may not be effectively suppressed, while if it exceeds 5000 mg, it is uneconomical. Furthermore, since the food or drink is remarkably excellent in immediate effect, it is preferable to take the food several times a day (2 to 3 times or more), especially before and after intense exercise, stress, and before and after smoking. It is recommended to take it when it is easily exposed to oxidative stress. In the case of a child, the intake is adjusted mainly depending on the body weight, but a half of the intake of the adult is a guide.
[0033]
The medicament of the embodiment contains the above-mentioned active ingredient, and preferably contains eriodictiol or diosmetin with an improved degree of purification. This medicament can be administered by injection or applied to the skin, but is mainly administered orally, and can be used for treating arteriosclerosis by suppressing oxidative degeneration of blood LDL. The content or concentration of the active ingredient in the drug may be the same as that of the above-mentioned food or drink (preferably a preparation) regardless of the administration form, and the usage and dose such as the daily dose, What is necessary is just to be the same as the intake in the case of the said food and drink.
[0034]
The effects exerted by the above embodiment will be described below.
The food or beverage of the embodiment intentionally contains aglycone (eriodictiol or diosmetin) derived from lemon. For this reason, since the food or drink contains the aglycone as an active ingredient in a high content, it is possible to extremely quickly and effectively suppress the oxidative degeneration of blood LDL, and to achieve a lifestyle-related disease centering on arteriosclerosis. Can exert a very high effect on the prevention of Further, since the active ingredient is remarkably excellent in absorbability in the body, the oxidative modification of blood LDL can be suppressed very quickly.
[0035]
Further, since the food or drink is to be orally ingested in the form of a beverage, a food or a preparation, it can be ingested remarkably easily and is very useful. In addition, the aglycone is usually hardly produced only by squeezing or extracting lemon juice or lemon fruit, and is almost always produced in a processing step other than the aglyconization treatment. I can't get it. On the other hand, since the pharmaceutical product of the embodiment contains aglycone derived from lemon (eriodictiol or diosmetin) as an active ingredient, it is possible to extremely quickly and effectively suppress oxidative denaturation of blood LDL, It can be highly effective in treating lifestyle-related diseases centering on arteriosclerosis.
[0036]
【Example】
Hereinafter, examples and comparative examples that embody the above embodiment will be described.
After fasting overnight, 10 test subjects (healthy males) were orally ingested the samples, and blood was collected from the test subjects before and 0.5, 1, 2, and 4 hours after ingestion, and the azo compound was collected. The antioxidant ability of blood LDL was measured by the conjugated diene method used. As the sample, 4.5 g of lemon flavonoid powder obtained by water extraction from lemon peel (Comparative Example 1), 4.5 g of lemon flavonoid powder and 1.33 g of vitamin C powder (Comparative Example 2), or lemon flavonoid powder 4 An aglycone-containing powder (Example 1) obtained by treating 0.5 g of β-glucosidase was used.
[0037]
The amount of the vitamin C powder used was the same as the amount of the vitamin C contained in 4.5 g of the lemon flavonoid powder determined by the hydrazine method. The aglycone-containing powder was obtained by dissolving 4.5 g of lemon flavonoid powder in water, adding 1000 units of β-glucosidase manufactured by Sigma, reacting at 37 ° C. for 60 minutes, and then drying. It is a powder and contains high content of aglycone obtained by subjecting a lemon flavonoid glycoside to aglyconization.
[0038]
As a result, in Comparative Examples 1 and 2, at any time after 0.5, 1, 2, and 4 hours of ingestion, the lag time, which is an index indicating the strength of the antioxidant ability of LDL as compared to before the ingestion, was higher. No significant prolongation was observed. On the other hand, in Example 1, the lag time before ingestion was 47.1 ± 5.3 minutes (p <0.05), but the lag time 0.5 hour after ingestion was 50.0 ± 5. After 7 minutes (p <0.05), the measurement of the antioxidant capacity of LDL also showed a significant extension of the lag time. Therefore, it was confirmed that the blood LDL of the test subject after ingestion of aglycone has a significantly high antioxidant ability and is less susceptible to arteriosclerosis.
[0039]
Next, in order to consider the significant extension of the lag time in Example 1, the in vivo absorption amounts of the lemon flavonoid powder of Comparative Example 1 and the aglycone-containing powder of Example 1 were measured by Miyake et al. , Journal of Agricultural and Food Chemistry, Vol. 48, 3217-3224 (2000). That is, β-glucuronidase and sulfatase were added to the serum collected in Comparative Example 1 and Example 1 and incubated at 37 ° C., and then oxalic acid was added to remove proteins. The sample was applied to a Sep-Pak C18 column (manufactured by Advantic), washed with water, eluted with methanol, and concentrated under reduced pressure to prepare an analysis sample. The amount of the flavonoid metabolites eriodictiol, homoeriodictiol, and hesperetin, which are metabolites of lemon flavonoids, was determined by HPLC to determine the amount absorbed in the body.
[0040]
As a result, when the aglycone-containing powder of Example 1 was taken, it was confirmed that aglycone was absorbed into the body at a high concentration at a very early stage of taking 0.5 to 1 hour, and 4 hours. It was confirmed that a relatively high concentration was maintained until later. From this, it was confirmed that aglycone was absorbed into the body very quickly and in large amounts compared to glycosides, and it was interpreted that this improved absorption in the body was linked to the above-mentioned prolonged lag time. can do.
[0041]
This embodiment can be embodied with the following modifications.
-In foods and drinks, aglycones derived from citrus fruits other than lemon may be contained as an active ingredient. The aglycone includes eriodictyol or diosmethine. As the citrus other than the lemon, lime or sudachi is suitably used. Even in the case of such a configuration, the same effect as the above embodiment can be exerted.
[0042]
As a technique to which the present invention is applied, the active ingredient of the above embodiment may be contained in cosmetics or quasi-drugs. At this time, the content or concentration of the active ingredient in the cosmetic or quasi-drug may be the same as in the case of the above-mentioned food or drink. Further, the daily use amount of the active ingredient may be the same as in the case of the above-mentioned food and drink. With such a configuration, it is possible to provide a cosmetic or quasi-drug having a function of effectively suppressing oxidative denaturation of blood LDL.
[0043]
Further, technical ideas that can be grasped from the embodiment will be described below.
-A medicine containing a lemon-derived flavonoid aglycone as an active ingredient, which has an action of suppressing oxidative denaturation of low-density lipoprotein in blood. With such a configuration, oxidative denaturation of low-density lipoprotein in blood can be effectively suppressed.
[0044]
The food or drink according to any one of claims 1 to 4, wherein the food or drink is manufactured through a step of adding a flavonoid aglycone derived from lemon.
The food or beverage according to any one of claims 1 to 4, further comprising a flavonoid aglycone at a higher concentration than lemon juice or lemon peel.
[0045]
-The food or drink according to any one of claims 2 to 4, wherein the flavonoid aglycone is eriodictyol and / or diosmetin.
[0046]
【The invention's effect】
As described above, according to the present invention, the following effects can be obtained.
The food or drink of the invention according to any one of claims 1 to 4, the pharmaceutical product of the invention of claim 5, the arteriosclerosis preventive agent of the invention of claim 6, and the LDL oxidative modification of the invention of claim 7 According to the inhibitor, oxidative denaturation of low-density lipoprotein in blood can be effectively suppressed.

Claims (7)

A food or drink containing erioctithiol and / or diosmetin, which has an action of suppressing oxidative denaturation of low-density lipoprotein in blood. A food or drink containing a lemon-derived flavonoid aglycone, wherein the flavonoid aglycone is obtained through a step of subjecting a lemon-derived flavonoid glycoside to an aglycone treatment. The food or drink according to claim 2, which has an action of suppressing oxidative denaturation of low-density lipoprotein in blood. The food or drink according to claim 2 or 3, wherein the aglyconization treatment is a glycosidase treatment or a microorganism fermentation treatment with a microorganism of the genus Aspergillus. A drug containing eriodictyol and / or diosmetin as an active ingredient, the drug having an action of suppressing oxidative denaturation of low-density lipoprotein in blood. An arteriosclerosis preventive agent containing eriodictiol and / or diosmetin as an active ingredient, which is used for the purpose of preventing arteriosclerosis. An LDL oxidation / denaturation inhibitor containing eriodictyol and / or diosmetin as an active ingredient, the LDL oxidation / denaturation inhibitor having an action of inhibiting the oxidation / denaturation of low-density lipoprotein in blood.