JPH04346933A - Multiplication inhibitor against dental caries fungus and pathogenic fungus of periodontal disease - Google Patents
Multiplication inhibitor against dental caries fungus and pathogenic fungus of periodontal diseaseInfo
- Publication number
- JPH04346933A JPH04346933A JP3148069A JP14806991A JPH04346933A JP H04346933 A JPH04346933 A JP H04346933A JP 3148069 A JP3148069 A JP 3148069A JP 14806991 A JP14806991 A JP 14806991A JP H04346933 A JPH04346933 A JP H04346933A
- Authority
- JP
- Japan
- Prior art keywords
- dental caries
- fungus
- citrus
- extract
- peel
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 208000002925 dental caries Diseases 0.000 title claims abstract description 26
- 208000028169 periodontal disease Diseases 0.000 title abstract description 8
- 239000003112 inhibitor Substances 0.000 title abstract description 5
- 241000233866 Fungi Species 0.000 title abstract 4
- 244000053095 fungal pathogen Species 0.000 title abstract 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 24
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 17
- 239000000284 extract Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 235000005979 Citrus limon Nutrition 0.000 claims abstract description 9
- 244000131522 Citrus pyriformis Species 0.000 claims abstract description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 241001672694 Citrus reticulata Species 0.000 claims abstract description 7
- 240000000560 Citrus x paradisi Species 0.000 claims abstract description 5
- 244000175448 Citrus madurensis Species 0.000 claims abstract description 4
- 235000017317 Fortunella Nutrition 0.000 claims abstract description 4
- 244000052769 pathogen Species 0.000 claims description 18
- 230000003239 periodontal effect Effects 0.000 claims description 18
- 241000894006 Bacteria Species 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 239000003966 growth inhibitor Substances 0.000 claims description 6
- 241000207199 Citrus Species 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- 235000005976 Citrus sinensis Nutrition 0.000 claims description 3
- 240000002319 Citrus sinensis Species 0.000 claims description 3
- 229940034610 toothpaste Drugs 0.000 claims description 3
- 239000000606 toothpaste Substances 0.000 claims description 3
- 241000555678 Citrus unshiu Species 0.000 claims 1
- 239000003599 detergent Substances 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 15
- 239000007788 liquid Substances 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 244000183685 Citrus aurantium Species 0.000 abstract 1
- 235000007716 Citrus aurantium Nutrition 0.000 abstract 1
- 241000273649 Citrus hassaku Species 0.000 abstract 1
- 241001337999 Citrus iyo Species 0.000 abstract 1
- 241001561395 Citrus natsudaidai Species 0.000 abstract 1
- 239000000551 dentifrice Substances 0.000 abstract 1
- 239000005445 natural material Substances 0.000 abstract 1
- 235000015203 fruit juice Nutrition 0.000 description 5
- 239000000401 methanolic extract Substances 0.000 description 5
- 229930014626 natural product Natural products 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 241000606125 Bacteroides Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 239000002044 hexane fraction Substances 0.000 description 2
- 239000002440 industrial waste Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241001478240 Coccus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000004195 gingiva Anatomy 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Cosmetics (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、虫歯菌、歯周病原菌増
殖阻害剤に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an agent for inhibiting the growth of dental caries and periodontal pathogens.
【０００２】更に詳細には、本発明は、柑橘類の果皮も
しくは果皮含有物の有機溶媒抽出物もしくはその処理物
を有効成分とする虫歯菌、歯周病原菌増殖阻害剤に関す
るものである。そして、果汁製造時に大量に産出され、
産業廃棄物とされている果汁搾り粕（果皮）の有効利用
として、果汁搾り粕（果皮）から虫歯菌、歯周病原菌増
殖阻害剤を得ることができる。More specifically, the present invention relates to an inhibitor of the growth of dental caries and periodontal pathogens, which contains an organic solvent extract of citrus peel or peel-containing material, or a processed product thereof as an active ingredient. It is produced in large quantities during fruit juice production,
As an effective use of fruit juice residue (pericarp), which is considered industrial waste, it is possible to obtain dental caries and periodontal pathogen growth inhibitors from the fruit juice residue (pericarp).
【０００３】従来、天然物由来で虫歯菌や歯周病原菌の
増殖を阻害する有効な物質は見出されていない。[0003] Hitherto, no substance derived from natural products that is effective in inhibiting the growth of dental caries bacteria and periodontal pathogens has been found.
【０００４】天然物由来で虫歯菌や歯周病原菌に対する
阻害物質が見出されれば、その物質を口内清浄剤や食品
に配合することによって、虫歯や歯周病を予防すること
が可能となる。[0004] If a substance derived from natural products that inhibits dental caries and periodontal pathogens is found, it will be possible to prevent dental caries and periodontal disease by incorporating the substance into mouth cleansers and foods.
【０００５】[0005]
【課題を解決するための手段】本発明者らは、天然物由
来の虫歯菌、歯周病原菌増殖阻害剤を求めて鋭意研究し
たところ、レモン、グレープフルーツなどの柑橘類の果
皮に虫歯菌、歯周病原菌の増殖を阻害する物質が含まれ
ていることを知ったのである。[Means for Solving the Problems] The present inventors conducted extensive research in search of growth inhibitors for dental caries bacteria and periodontal pathogens derived from natural products, and found that dental caries bacteria and periodontal pathogens were found on the peels of citrus fruits such as lemons and grapefruits. They learned that it contains substances that inhibit the growth of pathogenic bacteria.
【０００６】本発明は柑橘類の果皮もしくは果皮含有物
の有機溶媒抽出物もしくはその処理物を有効成分とする
虫歯菌、歯周病原菌増殖阻害剤に関するものである。The present invention relates to an agent for inhibiting the growth of dental caries and periodontal pathogens, which contains an organic solvent extract of citrus peel or peel-containing material, or a processed product thereof as an active ingredient.
【０００７】本発明において用いる柑橘類としてはレモ
ン、グレープフルーツ、ネーブルオレンジ、はっさく、
温州ミカン、キンカン、いよかん、夏ミカン、ダイダイ
などが例示されるが、柑橘類であれば広く使用すること
ができる。Citrus fruits used in the present invention include lemon, grapefruit, navel orange, hassaku,
Examples include unshiu mandarin oranges, kumquats, iyokan, summer mandarin oranges, and Japanese oranges, but any citrus fruit can be used.
【０００８】本発明においては柑橘類の果皮もしくは果
皮含有物が使用されるが、一般的には果汁を搾汁した後
の果皮のついた搾り粕や分離した果皮が使用される。[0008] In the present invention, citrus fruit peel or pericarp-containing material is used, but in general, pomace lees with pericarp attached after squeezing the fruit juice or separated pericarp are used.
【０００９】本発明において、虫歯菌、歯周病原菌増殖
阻害性成分は柑橘類の果皮もしくは果皮含有物の有機溶
媒抽出物に含まれることが明らかとなった。In the present invention, it has been revealed that components inhibiting the growth of dental caries bacteria and periodontal pathogens are contained in organic solvent extracts of citrus fruit peels or peel-containing materials.
【００１０】有機溶媒としては、メタノール、エタノー
ル、クロロホルム、酢酸エチル、ｎ−ブタノールなどが
あるが、好ましい有機溶媒としてはメタノール、エタノ
ール、クロロホルムがあげられる。Examples of organic solvents include methanol, ethanol, chloroform, ethyl acetate, and n-butanol, and preferred organic solvents include methanol, ethanol, and chloroform.
【００１１】レモン搾り粕をメタノールで抽出処理し、
後減圧濃縮乾固して得たメタノール抽出物の物性は次の
表１に示す通りである。[0011] Lemon squeezed lees is extracted with methanol,
The physical properties of the methanol extract obtained by concentrating to dryness under reduced pressure are shown in Table 1 below.
【００１２】0012
【表１】[Table 1]
【００１３】本発明におけるメタノールなどの有機溶媒
抽出物については、これを更にヘキサンで抽出処理し、
液部を減圧濃縮乾固して有効成分をより濃縮することが
できる。[0013] Regarding the organic solvent extract such as methanol in the present invention, this is further extracted with hexane,
The active ingredient can be further concentrated by concentrating the liquid part to dryness under reduced pressure.
【００１４】レモン搾り粕のメタノール抽出物を更にヘ
キサンで抽出処理し、液部を減圧濃縮乾固して得たメタ
ノール抽出物ヘキサン可溶画分の物性は次の表２に示す
通りである。The methanol extract of lemon juice was further extracted with hexane, and the liquid portion was concentrated to dryness under reduced pressure. The physical properties of the hexane-soluble fraction of the methanol extract were as shown in Table 2 below.
【００１５】[0015]
【表２】[Table 2]
【００１６】本発明においては、柑橘類の果皮もしくは
果皮含有物の有機溶媒抽出物もしくはその処理物に虫歯
菌、歯周病原菌の増殖阻害性を見出したもので、有機溶
媒抽出物やそのヘキサン可溶画分、更にはこれらの精製
物などが有効成分として使用されるものである。[0016] In the present invention, it has been found that an organic solvent extract of citrus fruit peel or pericarp containing material or a processed product thereof has the ability to inhibit the growth of dental caries bacteria and periodontal pathogens. Fractions and even purified products thereof are used as active ingredients.
【００１７】本発明における有効成分は歯みがき、口内
清浄剤又は各種食品に添加することによって虫歯菌、歯
周病原菌の増殖を阻害し、虫歯を防止し、歯周病を抑制
することを可能とするものである。[0017] The active ingredient of the present invention can be added to toothpaste, mouth cleansers, or various foods to inhibit the growth of caries bacteria and periodontal pathogens, prevent tooth decay, and suppress periodontal disease. It is something.
【００１８】次に、本発明の実施例を示す。Next, examples of the present invention will be shown.
【００１９】[0019]
【実施例１】１Ｋｇのレモン搾り粕に２Ｋｇの表３の各
種有機溶媒を加え、室温で１夜放置し、抽出処理した。[Example 1] 2 kg of various organic solvents shown in Table 3 were added to 1 kg of lemon squeezed lees, and the mixture was left at room temperature overnight for extraction.
【００２０】抽出液を分離し、これを減圧濃縮乾固し、
これをすべて約倍量のメタノールに溶解し、各試料とし
た。[0020] Separate the extract, concentrate it to dryness under reduced pressure,
All of this was dissolved in about double the amount of methanol to prepare each sample.
【００２１】得られた各試料を虫歯菌（Ｓｔｒｅｐｔｏ
ｃｏｃｃｕｓ ｍｕｔａｎｓ）又は歯周病菌（Ｂａｃ
ｔｅｒｏｉｄｅｓ ｇｉｎｇｉｖａｌｉｓ）をまいた
ブイヨン寒天培地上に流して、菌増殖阻害活性を調べた
。その結果は次の表３に示される。[0021] Each of the obtained samples was infected with Streptococcus bacteria.
coccus mutans) or periodontal disease bacteria (Bac
The bacterial growth inhibitory activity was examined by pouring the mixture onto a bouillon agar medium on which teroides gingivalis was spread. The results are shown in Table 3 below.
【００２２】[0022]
【表３】[Table 3]
【００２３】[0023]
【実施例２】果汁製造時に産出され、産業廃棄物である
柑橘果実（レモン、グレープフルーツ、ネーブルオレン
ジ、はっさく、温州ミカン、キンカン、いよかん）搾り
粕の抽出液から、虫歯菌、歯周病原菌の増殖阻害活性を
調べた。[Example 2] Growth of dental caries bacteria and periodontal pathogens from extracts of citrus fruit (lemon, grapefruit, navel orange, hassaku, unshiu mandarin, kumquat, and iyokan) pomace produced during fruit juice production and which is industrial waste. The inhibitory activity was investigated.
【００２４】柑橘果実搾り粕３００ｇに１００％メタノ
ール５００ｍｌを加え、室温で１日放置して抽出し、減
圧濃縮乾固して１３．５ｇのサンプルを得た。[0024] 500 ml of 100% methanol was added to 300 g of citrus fruit pomace, left to stand for one day at room temperature for extraction, and concentrated to dryness under reduced pressure to obtain a 13.5 g sample.
【００２５】虫歯の主原因菌として知られるＳｔｒｅｐ
ｔｏｃｏｃｃｕｓ ｍｕｔａｎｓ、または虫周菌とし
て知られるＢａｃｔｅｒｏｉｄｅｓ ｇｉｎｇｉｖａ
ｌｉｓ、Ｂａｃｔｅｒｏｉｄｅｓ ｉｎｔｅｒｍｅｄ
ｉｕｓについての増殖阻害効果を調べた。ブレインハー
トインヒュージョン（ＢＨＩ）液体培地、ＧＡＭ液体培
地の５ｍｌに、それぞれの菌を１０５ｃｅｌｌｓ／ｍｌ
になるように接種し、３７度で３日間、静置培養した。
上記の培地にサンプルを添加して培養後、トーマの血球
計算盤で菌数測定し、１０８ｃｅｌｌｓ／ｍｌ以上の場
合に増殖と判断した。それぞれの柑橘果実搾り粕サンプ
ルの最小阻害濃度を調べた。その結果は次の表４に示さ
れる。[0025] Strep is known as the main cause of tooth decay.
Bacteroides gingiva, also known as tococcus mutans
lis, Bacteroides intermed
The growth inhibitory effect on the ius was investigated. Add 105 cells/ml of each bacteria to 5 ml of Brain Heart Infusion (BHI) liquid medium and GAM liquid medium.
The cells were inoculated and cultured stationary at 37 degrees for 3 days. After adding the sample to the above medium and culturing, the number of bacteria was measured using a Tomah hemocytometer, and growth was determined when the number was 108 cells/ml or more. The minimum inhibitory concentration of each citrus fruit pomace sample was investigated. The results are shown in Table 4 below.
【００２６】[0026]
【表４】[Table 4]
【００２７】[0027]
【実施例３】実施例１で得たレモン搾り粕メタノール抽
出液濃縮乾固物に、１００ｍｌの水を加えて溶かし、分
液漏斗に移す。これに、２０ｍｌのヘキサンを加え、ヘ
キサン可溶画分を集めた。（この回収操作を３回繰り返
した。）これを減圧濃縮乾固してヘキサン画分濃縮乾固
物とした。[Example 3] Add 100 ml of water to the concentrated and dried lemon juice methanol extract obtained in Example 1 to dissolve, and transfer to a separatory funnel. 20 ml of hexane was added to this, and the hexane soluble fraction was collected. (This collection operation was repeated three times.) This was concentrated to dryness under reduced pressure to obtain a hexane fraction concentrated to dryness.
【００２８】メタノール抽出液濃縮乾固物及びヘキサン
画分濃縮乾固物について、実施例２と同様の方法で最小
阻害濃度を調べた。その結果は次の表５に示される。The minimum inhibitory concentration of the concentrated and dried methanol extract and the concentrated and dried hexane fraction was examined in the same manner as in Example 2. The results are shown in Table 5 below.
【００２９】[0029]
【表５】[Table 5]
【００３０】[0030]
【発明の効果】本発明の虫歯菌、歯周病原菌増殖阻害剤
は柑橘類の果皮から抽出されたもので、安全性がきわめ
て高く、歯みがき、口内清浄剤、各種食品に適宜添加す
ることができる。[Effects of the Invention] The growth inhibitor for dental caries and periodontal pathogens of the present invention is extracted from the peel of citrus fruits, and is extremely safe and can be appropriately added to toothpaste, mouth cleansers, and various foods.
Claims (5)
機溶媒抽出物もしくはその処理物を有効成分とする虫歯
菌、歯周病原菌増殖阻害剤。1. An agent for inhibiting the growth of dental caries and periodontal pathogens, which contains an organic solvent extract of citrus peel or peel-containing material, or a processed product thereof as an active ingredient.
ネーブルオレンジ、はっさく、温州ミカン、キンカン、
いよかん、夏ミカン、ダイダイから選択されたものであ
る請求項１の虫歯菌、歯周病原菌増殖阻害剤。[Claim 2] The citrus fruit is lemon, grapefruit,
Navel orange, Hassaku, Satsuma mandarin orange, Kumquat,
The growth inhibitor of dental caries and periodontal pathogens according to claim 1, which is selected from Japanese mandarin orange, summer mandarin orange, and Japanese mandarin orange.
タノール、エタノール、クロロホルム又は酢酸エチルに
よる抽出物を有効成分とする虫歯菌、歯周病原菌増殖阻
害剤。3. An agent for inhibiting the growth of dental caries and periodontal pathogens, the active ingredient being an extract of citrus peel or peel containing material using methanol, ethanol, chloroform or ethyl acetate.
機溶媒抽出物からのヘキサン可溶画分を有効成分とする
虫歯菌、歯周病原菌増殖阻害剤。4. A growth inhibitor for dental caries and periodontal pathogens, the active ingredient being a hexane-soluble fraction from an organic solvent extract of citrus peel or peel-containing material.
原菌増殖阻害剤を添加してなる歯みがき、口内清浄剤又
は食品。5. A toothpaste, a mouth cleansing agent, or a food product containing the growth inhibitor of dental caries bacteria and periodontal pathogens according to claims 1 to 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3148069A JPH04346933A (en) | 1991-05-24 | 1991-05-24 | Multiplication inhibitor against dental caries fungus and pathogenic fungus of periodontal disease |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3148069A JPH04346933A (en) | 1991-05-24 | 1991-05-24 | Multiplication inhibitor against dental caries fungus and pathogenic fungus of periodontal disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04346933A true JPH04346933A (en) | 1992-12-02 |
Family
ID=15444518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3148069A Pending JPH04346933A (en) | 1991-05-24 | 1991-05-24 | Multiplication inhibitor against dental caries fungus and pathogenic fungus of periodontal disease |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04346933A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245412A (en) * | 1995-03-08 | 1996-09-24 | Norin Suisansyo Chugoku Nogyo Shikenjo | Composition showing inhibitory activity against arachidonic acid metabolizing enzyme and its production |
| WO1998016239A1 (en) * | 1996-10-14 | 1998-04-23 | Korea Institute Of Science And Technology | CITRUS PEEL EXTRACT AS 3-HYDROXY-3-METHYLGLUTARYL CoA(HMG-CoA) REDUCTASE INHIBITOR |
| JP2008069138A (en) * | 2006-09-15 | 2008-03-27 | Chun-Erh Wang | Oral composition |
| CN105963217A (en) * | 2016-07-09 | 2016-09-28 | 青岛大学 | Preparation method of toothpaste composition with caries prevention effect |
| WO2019159434A1 (en) * | 2018-02-15 | 2019-08-22 | 理恵 堤 | Yuko-containing composition |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5785319A (en) * | 1980-11-16 | 1982-05-28 | Tsurui Yakuhin Kogyo Kk | Agent for dental caries |
| JPS5929620A (en) * | 1982-08-11 | 1984-02-16 | T Hasegawa Co Ltd | Preventing agent for carious tooth |
| JPS59175410A (en) * | 1983-03-26 | 1984-10-04 | Kanebo Shokuhin Kk | Cariostatic agent |
| JPS61122221A (en) * | 1984-11-19 | 1986-06-10 | Osaka Chem Lab | Remedy for periodontosis |
| JPS62148426A (en) * | 1985-12-23 | 1987-07-02 | Rooto Seiyaku Kk | Remedy for periodontosis |
-
1991
- 1991-05-24 JP JP3148069A patent/JPH04346933A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5785319A (en) * | 1980-11-16 | 1982-05-28 | Tsurui Yakuhin Kogyo Kk | Agent for dental caries |
| JPS5929620A (en) * | 1982-08-11 | 1984-02-16 | T Hasegawa Co Ltd | Preventing agent for carious tooth |
| JPS59175410A (en) * | 1983-03-26 | 1984-10-04 | Kanebo Shokuhin Kk | Cariostatic agent |
| JPS61122221A (en) * | 1984-11-19 | 1986-06-10 | Osaka Chem Lab | Remedy for periodontosis |
| JPS62148426A (en) * | 1985-12-23 | 1987-07-02 | Rooto Seiyaku Kk | Remedy for periodontosis |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08245412A (en) * | 1995-03-08 | 1996-09-24 | Norin Suisansyo Chugoku Nogyo Shikenjo | Composition showing inhibitory activity against arachidonic acid metabolizing enzyme and its production |
| WO1998016239A1 (en) * | 1996-10-14 | 1998-04-23 | Korea Institute Of Science And Technology | CITRUS PEEL EXTRACT AS 3-HYDROXY-3-METHYLGLUTARYL CoA(HMG-CoA) REDUCTASE INHIBITOR |
| JP2008069138A (en) * | 2006-09-15 | 2008-03-27 | Chun-Erh Wang | Oral composition |
| CN105963217A (en) * | 2016-07-09 | 2016-09-28 | 青岛大学 | Preparation method of toothpaste composition with caries prevention effect |
| WO2019159434A1 (en) * | 2018-02-15 | 2019-08-22 | 理恵 堤 | Yuko-containing composition |
| JP2022113827A (en) * | 2018-02-15 | 2022-08-04 | 株式会社シトリアン | Citrus yoko-containing composition |
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