JPH07157494A - New isoflavone glycoside and cosmetic containing the same - Google Patents
New isoflavone glycoside and cosmetic containing the sameInfo
- Publication number
- JPH07157494A JPH07157494A JP30507393A JP30507393A JPH07157494A JP H07157494 A JPH07157494 A JP H07157494A JP 30507393 A JP30507393 A JP 30507393A JP 30507393 A JP30507393 A JP 30507393A JP H07157494 A JPH07157494 A JP H07157494A
- Authority
- JP
- Japan
- Prior art keywords
- isoflavone glycoside
- cosmetic
- whitening effect
- glycoside
- glucosyl
- 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.)
- Granted
Links
Landscapes
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は皮膚美白効果に優れ、日
焼けによるシミ、ソバカスを防止する効果に優れた新規
イソフラボン配糖体及びこれを含有する化粧料に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel isoflavone glycoside having an excellent skin whitening effect and an effect of preventing spots and freckles caused by sunburn, and a cosmetic containing the same.
【０００２】[0002]
【従来の技術】皮膚のシミ、ソバカスは一般に紫外線に
よる刺激やホルモン異常などによって、メラノサイトが
活性化され、そこで生合成されたメラニン色素が皮膚に
沈着して発生するものと考えられている。従来、このよ
うなシミ、ソバカスに対する治療の方法として、アスコ
ルビン酸類、ハイドロキノン誘導体、コウジ酸類、胎盤
抽出物などのメラニン抑制剤が用いられてきたが、これ
らの物質は単独で使用した場合、メラニン生成抑制効果
は弱く、化粧品などに配合した場合充分な美白効果を発
現できないものであった。2. Description of the Related Art It is generally considered that blemishes and freckles on the skin are generally activated by the stimulation of ultraviolet rays, hormonal abnormalities, etc., and the melanin pigment biosynthesized there is deposited on the skin. Conventionally, as a method for treating such spots and freckles, melanin inhibitors such as ascorbic acids, hydroquinone derivatives, kojic acids, and placenta extract have been used, but when these substances are used alone, they produce melanin. The inhibitory effect was weak, and when blended in cosmetics and the like, a sufficient whitening effect could not be exhibited.
【０００３】[0003]
【発明が解決しようとする課題】従って、本発明の目的
は皮膚の美白効果に優れ、シミ、ソバカスを有効に予防
・治療し得る物質及びこれを含有する化粧料を提供する
ことにある。SUMMARY OF THE INVENTION Therefore, an object of the present invention is to provide a substance having an excellent whitening effect on the skin and capable of effectively preventing and treating spots and freckles, and a cosmetic containing the same.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、斯かる実
情に鑑み、優れた美白効果を有する化粧料を開発すべく
鋭意研究を重ねた結果、下記一般式（１）で表わされる
新規イソフラボン配糖体がメラニンの生成を抑制し、色
素沈着を防止し、優れた美白効果を示すことを見出し、
更にこれとアスコルビン酸類等の公知の美白剤とを組合
せると美白効果が相乗的に高まることを見出し本発明を
完成した。In view of such circumstances, the present inventors have earnestly studied to develop a cosmetic having an excellent whitening effect, and as a result, a novel compound represented by the following general formula (1). It was found that isoflavone glycosides suppress the production of melanin, prevent pigmentation, and exhibit an excellent whitening effect,
Further, they have found that the combination of this with a known whitening agent such as ascorbic acid synergistically enhances the whitening effect, and completed the present invention.
【０００５】すなわち本発明は、下記一般式（１）That is, the present invention provides the following general formula (1)
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】（式中、Ｒ1 はアピオシル基、グルコシル
基又は水素原子を示し、Ｒ2 は水素原子又は水酸基を示
し、Ｒ3 は水素原子又はグルコシル基を示す）で表わさ
れるイソフラボン配糖体の第一の発明と、これを含有す
る化粧料の第二の発明と、これとアスコルビン酸類、ハ
イドロキノン誘導体、コウジ酸類及び胎盤抽出物から選
ばれる１種又は２種以上とを含有する化粧料の第三の発
明を提供するものである。Of the isoflavone glycoside represented by the formula: wherein R 1 represents an apiosyl group, a glucosyl group or a hydrogen atom, R 2 represents a hydrogen atom or a hydroxyl group, and R 3 represents a hydrogen atom or a glucosyl group. A first invention, a second invention of a cosmetic composition containing the same, and a second invention of a cosmetic composition containing the same and one or more selected from ascorbic acids, hydroquinone derivatives, kojic acids and placenta extracts. It provides the third invention.
【０００８】本発明のイソフラボン配糖体は、前記一般
式（１）で表わされるものであるが、このうち、６″−
Ｏ−アピオシルプエラリン−４′−Ｏ−グルコシド、
６″−Ｏ−グルコシルプエラリン、３′−ヒドロキシプ
エラリン−４′−Ｏ−グルコシド、６″−Ｏ−アピオシ
ル−３′−ヒドロキシプエラリンが美白効果が高く化粧
料に用いるのに好ましい。The isoflavone glycoside of the present invention is represented by the above general formula (1). Of these, 6 ″-
O-apiosylpuerarin-4'-O-glucoside,
6 ″ -O-glucosyl puerarin, 3′-hydroxypuerarin-4′-O-glucoside, and 6 ″ -O-apiosyl-3′-hydroxypuerarin are preferable for use in cosmetics because of their high whitening effect.
【０００９】本発明のイソフラボン配糖体（１）は、例
えば葛根抽出液よりクロマトグラフィーにて分取する方
法等により得られる。The isoflavone glycoside (1) of the present invention can be obtained, for example, by a method such as fractionation from Kuzukon extract by chromatography.
【００１０】すなわち乾燥葛根を粉砕し、水、エタノー
ル等のアルコール、アセトンなどの親水性有機溶媒、又
はこれらの混合溶液を用いて抽出液を得る。得られた抽
出液から溶媒を除去して得た残渣をヘキサン、石油エー
テル、ジエチルエーテル、クロロホルム、メチルエチル
ケトン、酢酸エチル、アセトン、イソプロピルアルコー
ル、メタノール、エタノールより選ばれる少なくとも一
つの溶媒を溶出溶媒として、ＤＩＡＩＯＮ ＨＰ−２
０、ＴＳＫＧＥＬ ＨＷ−４０などのポーラスポリマ
ー、Ｓｅｐｈａｄｅｘ ＬＨ−２０などのセファデック
ス、ポリアミド、セルロース、逆相系シリカゲル、シリ
カゲルなどを担体に用いたカラムクロマトグラフィー、
分取ＨＰＬＣ、調製薄層クロマトグラフィーに付すこと
により上記のイソフラボン配糖体を得ることができる。That is, dried kudzu roots are crushed and an extract is obtained using water, alcohol such as ethanol, hydrophilic organic solvent such as acetone, or a mixed solution thereof. The residue obtained by removing the solvent from the obtained extract is hexane, petroleum ether, diethyl ether, chloroform, methyl ethyl ketone, ethyl acetate, acetone, isopropyl alcohol, methanol, at least one solvent selected from ethanol as an elution solvent, DIAION HP-2
0, column chromatography using a porous polymer such as TSKGEL HW-40, Sephadex such as Sephadex LH-20, polyamide, cellulose, reverse phase silica gel, silica gel, etc. as a carrier,
The above isoflavone glycoside can be obtained by subjecting it to preparative HPLC and preparative thin layer chromatography.
【００１１】本発明の化粧料は、上記イソフラボン配糖
体（１）を配合したものであるが、この配合量は化粧料
全重量に対し、０．００００１〜２．５重量％とするこ
とが好ましく、特に０．０００１〜１重量％（以下、単
に「％」という）とすることが美白効果のため好まし
い。The cosmetic of the present invention contains the above-mentioned isoflavone glycoside (1), and the amount of this is 0.00001 to 2.5% by weight based on the total weight of the cosmetic. In particular, 0.0001 to 1% by weight (hereinafter, simply referred to as "%") is preferable for whitening effect.
【００１２】本発明の化粧料は、イソフラボン配糖体
（１）と共に、アスコルビン酸類、ハイドロキノン誘導
体、コウジ酸類及び胎盤抽出物から選ばれる１種又は２
種以上を配合せしめると相乗的に美白効果を高めること
ができる。The cosmetic of the present invention comprises, together with the isoflavone glycoside (1), one or two selected from ascorbic acids, hydroquinone derivatives, kojic acids and placenta extracts.
Blending more than one species can enhance the whitening effect synergistically.
【００１３】本発明に用いるアスコルビン酸類として
は、Ｌ−アスコルビン酸、Ｌ−アスコルビン酸リン酸エ
ステル、Ｌ−アスコルビン酸硫酸エステル及びそれぞれ
の金属塩、例えばナトリウム塩、カリウム塩、マグネシ
ウム塩、カルシウム塩、アルミニウム塩などを好ましい
ものとして挙げることができるが、これらに限定される
ものではない。Examples of the ascorbic acid used in the present invention include L-ascorbic acid, L-ascorbic acid phosphoric acid ester, L-ascorbic acid sulfuric acid ester and metal salts thereof, such as sodium salt, potassium salt, magnesium salt, calcium salt, Aluminum salts and the like can be mentioned as preferable ones, but the present invention is not limited thereto.
【００１４】また、ハイドロキノン誘導体としては、ハ
イドロキノンと糖の縮合物、アルキル化ハイドロキノン
と糖の縮合物などがあり、例えばアルブチン等を好まし
いものとして挙げることができる。コウジ酸類として
は、コウジ酸、コウジ酸のモノエステル及びジエステ
ル、例えばコウジ酸ブチレート、コウジ酸パルミテー
ト、コウジ酸ステアレート、コウジ酸オレエートなどを
好ましいものとして挙げることができるがこれらに限定
されるものではない。As the hydroquinone derivative, there are condensates of hydroquinone and sugar, condensates of alkylated hydroquinone and sugar, and preferred examples include arbutin and the like. Examples of kojic acids include kojic acid, monoesters and diesters of kojic acid, such as butyrate of kojic acid, palmitate of kojic acid, stearate of kojic acid, and oleate of kojic acid, but are not limited thereto. Absent.
【００１５】胎盤抽出物としては牛、豚などの動物の胎
盤の水溶性成分を挙げることができ、市販されている水
溶性プラセンタエキスを用いてもよい。Examples of the placenta extract include water-soluble components of placenta of animals such as cows and pigs, and commercially available water-soluble placenta extract may be used.
【００１６】本発明の化粧料にこれらのアスコルビン酸
類等の美白剤の１種又は２種以上配合する場合、その配
合量は化粧料の０．０１〜３０％、特に０．１〜５％と
することが好ましい。すなわちこれが０．０１％未満で
はイソフラボン配糖体（１）との相乗効果が得られにく
く、３０％を超えると化粧料としての保存安定性や使用
感が著しく劣るため好ましくない。When one or more of these whitening agents such as ascorbic acid are blended in the cosmetic of the present invention, the blending amount is 0.01 to 30%, particularly 0.1 to 5% of the cosmetic. Preferably. That is, if it is less than 0.01%, it is difficult to obtain a synergistic effect with the isoflavone glycoside (1), and if it exceeds 30%, storage stability and usability as cosmetics are remarkably deteriorated, which is not preferable.
【００１７】更に、本発明の化粧料には、本発明の効果
を損わない範囲において、上記必須成分以外の通常化粧
品、医薬部外品、医薬品等に用いられる各種任意成分を
適宜配合することができる。かかる任意成分としては、
例えば精製水、エタノール、油性物質、保湿剤、増粘
剤、防腐剤、乳化剤、薬効成分、粉体、紫外線吸収剤、
色素、香料、乳化安定剤、pH調整剤等を挙げることがで
きる。具体的には、油性成分としては流動パラフィン、
ワセリン、パラフィンワックス、スクワラン、ミツロ
ウ、カルナウバロウ、オリーブ油、ラノリン、高級アル
コール、脂肪酸、高級アルコールと脂肪酸の合成エステ
ル油、シリコーン油等が挙げられ、保湿剤としてはソル
ビトール、キシリトール、グリセリン、マルチトール、
プロピレングリコール、１，３−ブチレングリコール、
１，４−ブチレングリコール、ピロリドンカルボン酸ナ
トリウム、乳酸、乳酸ナトリウム、ポリオキシプロピレ
ン脂肪酸エステル、ポリエチレングリコール等が挙げら
れ、増粘剤としてはカルボキシビニルポリマー、カルボ
キシメチルセルロース、ポリビニルアルコール、カラギ
ーナン、ゼラチン等の水溶性高分子、塩化ナトリウム、
塩化カリウム等の電解質などが挙げられ、防腐剤として
は尿素、メチルパラベン、エチルパラベン、プロピルパ
ラベン、ブチルパラベン、安息香酸ナトリウム等が挙げ
られ、乳化剤としてはポリオキシエチレンアルキルエー
テル、ポリオキシエチレン脂肪酸エステル、ポリオキシ
エチレンソルビタン脂肪酸エステル、グリセリン脂肪酸
エステル、ポリグリセリン脂肪酸エステル、ポリオキシ
エチレングリセリン脂肪酸エステル、ポリオキシエチレ
ン硬化ヒマシ油、ポリオキシエチレンソルビトール脂肪
酸エステル等の非イオン界面活性剤が挙げられ、粉体と
してはタルク、セリサイト、マイカ、カオリン、シリ
カ、ベントナイト、バーミキュライト、亜鉛華、雲母、
雲母チタン、酸化チタン、酸化マグネシウム、酸化ジル
コニウム、硫酸バリウム、ベンガラ、酸化鉄、群青等が
挙げられる。本発明の化粧料は、系の安定性のため酸性
〜中性（pH７以下）とすることが好ましい。ここで用い
るpH調整剤としては乳酸−乳酸ナトリウム、クエン酸−
クエン酸ナトリウム等の緩衝剤が挙げられる。Further, the cosmetic of the present invention may be appropriately blended with various optional components used in ordinary cosmetics, quasi drugs, pharmaceuticals, etc. other than the above-mentioned essential components, within a range that does not impair the effects of the present invention. You can Such optional components include
For example, purified water, ethanol, oily substances, moisturizers, thickeners, preservatives, emulsifiers, medicinal ingredients, powders, ultraviolet absorbers,
Examples thereof include dyes, fragrances, emulsion stabilizers and pH adjusters. Specifically, as the oil component, liquid paraffin,
Vaseline, paraffin wax, squalane, beeswax, carnauba wax, olive oil, lanolin, higher alcohols, fatty acids, synthetic ester oils of higher alcohols and fatty acids, silicone oils, and the like, and moisturizing agents include sorbitol, xylitol, glycerin, maltitol,
Propylene glycol, 1,3-butylene glycol,
1,4-butylene glycol, sodium pyrrolidonecarboxylate, lactic acid, sodium lactate, polyoxypropylene fatty acid ester, polyethylene glycol and the like can be mentioned. As the thickener, carboxyvinyl polymer, carboxymethylcellulose, polyvinyl alcohol, carrageenan, gelatin and the like can be mentioned. Water-soluble polymer, sodium chloride,
Examples include electrolytes such as potassium chloride, preservatives such as urea, methylparaben, ethylparaben, propylparaben, butylparaben, sodium benzoate, and the like, emulsifiers such as polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, Nonionic surfactants such as polyoxyethylene sorbitan fatty acid ester, glycerin fatty acid ester, polyglycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxyethylene sorbitol fatty acid ester, and the like, and powders Is talc, sericite, mica, kaolin, silica, bentonite, vermiculite, zinc flower, mica,
Examples thereof include titanium mica, titanium oxide, magnesium oxide, zirconium oxide, barium sulfate, red iron oxide, iron oxide and ultramarine. The cosmetic of the present invention is preferably acidic to neutral (pH 7 or less) for stability of the system. The pH adjuster used here is lactic acid-sodium lactate, citric acid-
Examples include buffering agents such as sodium citrate.
【００１８】本発明の化粧料は常法に従って製造するこ
とができる。また、本発明の対象となる化粧料は、一般
の皮膚化粧料に限定されるものではなく、医薬部外品、
外用医薬品等を包含するものであり、その剤型もその目
的に応じて任意に選択することができ、クリーム状、軟
膏状、乳液状、ローション状、溶液状、ゲル状、パック
状、スティック状等とすることができる。The cosmetic material of the present invention can be manufactured by a conventional method. Further, the cosmetics to which the present invention is applied are not limited to general skin cosmetics, but include quasi-drugs,
It includes external medicines, and its dosage form can be arbitrarily selected according to its purpose, and is in the form of cream, ointment, emulsion, lotion, solution, gel, pack, stick. And so on.
【００１９】[0019]
【発明の効果】本発明のイソフラボン配糖体（１）は、
優れた皮膚の美白効果と日焼け等によるシミ及びソバカ
スの予防及び治療効果とを有し、この効果は、アスコル
ビン酸類等を併用することにより相乗的に高められる。
従って、これらを配合した化粧料は優れた美白効果を示
す。The isoflavone glycoside (1) of the present invention is
It has an excellent skin whitening effect and a preventive and therapeutic effect on spots and freckles due to sunburn and the like, and this effect is synergistically enhanced by the combined use of ascorbic acid and the like.
Therefore, the cosmetics containing them show an excellent whitening effect.
【００２０】[0020]
【実施例】以下、実施例を挙げて本発明を更に詳細に説
明するが、本発明はこれらに限定されるものではない。The present invention will be described in more detail with reference to examples, but the present invention is not limited thereto.
【００２１】実施例１ イソフラボン配糖体の製造：葛根原体（粉末）１００ｇ
を２０％エタノール水１リットルで室温にて抽出し、濾
過後濃縮して粗抽出物（３９．８ｇ）を得た。これを
０．５リットルの水に溶解したのち等量の酢酸エチルで
３回分配して得た水層をＤＩＡＩＯＮ ＨＰ−２０カラ
ムクロマトに供した。水洗後、２０％メタノール溶出区
（画分Ａ１．２ｇ）、４０％メタノール溶出区（画分Ｂ
２．８ｇ）を得た。画分Ｂを中圧逆相クロマト（メルク
社 ローバーカラム ＲＰ−１８ ｓｉｚｅＢ、メタノ
ール・水系）に供し２０％メタノール画分（画分Ｂ−２
０）、３０％メタノール画分（画分Ｂ−３０）を得た。
画分Ｂ−２０を更にＨＰＬＣ（ＪＡＩＧＥＬ ＯＤＳ
１０μm １０×２５０mm、０．３％酢酸水：アセトニト
リル＝９：１、流速９ml／min 、検出ＵＶ２５４nm）に
供し、３′−ヒドロキシプエラリン−４′−Ｏ−グルコ
シドを１５．２mg得た。同様に画分Ｂ−３０をＨＰＬＣ
（３％酢酸水：アセトニトリル＝８８：１２）に供し、
６″−Ｏ−アピオシルプエラリン−４′−Ｏ−グルコシ
ドを１２．２mg、６″−Ｏ−グルコシルプエラリンを１
８．０mg、６″−Ｏ−アピオシル−３′−ヒドロキシプ
エラリンを８．２mg得た。以下に機器分析結果を示す。Example 1 Production of isoflavone glycoside: Kuzukogen (powder) 100 g
Was extracted with 1 liter of 20% ethanol water at room temperature, filtered and concentrated to obtain a crude extract (39.8 g). This was dissolved in 0.5 liter of water and then partitioned three times with an equal amount of ethyl acetate, and the obtained aqueous layer was subjected to DIAION HP-20 column chromatography. After washing with water, 20% methanol elution zone (fraction A 1.2 g), 40% methanol elution zone (fraction B)
2.8 g) was obtained. Fraction B was subjected to medium pressure reverse phase chromatography (Merck Rover column RP-18 sizeB, methanol / water system) to obtain a 20% methanol fraction (fraction B-2).
0) and a 30% methanol fraction (fraction B-30) were obtained.
Fraction B-20 was further analyzed by HPLC (JAIGEL ODS
10 μm 10 × 250 mm, 0.3% acetic acid water: acetonitrile = 9: 1, flow rate 9 ml / min, detection UV254 nm) to obtain 15.2 mg of 3′-hydroxypuerarin-4′-O-glucoside. Similarly, fraction B-30 was analyzed by HPLC.
(3% acetic acid water: acetonitrile = 88: 12),
6 "-O-apiosylpuerarin-4'-O-glucoside 12.2 mg, 6" -O-glucosylpuerarin 1
8.0 mg and 6 ″ -O-apiosyl-3′-hydroxypuerarin of 8.2 mg were obtained. The results of instrumental analysis are shown below.
【００２２】６″−Ｏ−アピオシルプエラリン−４′−
Ｏ−グルコシド FAB-MS (M+H)+ 7111 H-NMR δ(DMSO-d6) TMS ; 4.77(d,J=2.8Hz,1H), 4.80
(d-like,1H),4.92(d,J=7.0Hz,1H), 7.00(d,J=8.8Hz,1
H),7.08(d,J=8.7Hz,2H), 7.52(d,J=8.7Hz,2H),7.94(d,J
=8.8Hz,1H), 8.40(s,1H).13 C-NMR δ(DMSO-d6) TMS ; 60.7, 62.9, 68.3, 69.7,
70.5, 70.7,73.2, 73.2, 73.4, 75.7, 76.6, 77.0, 78.
6,78.7, 80.0, 100.3, 102.4, 109.0, 112.5,115.0, 11
5.9, 116.8, 116.7, 122.8, 125.5,126.3, 129.9, 153.
1, 156.1, 157.1, 161.1,174.8.6 "-O-apiosylpuerarin-4'-
O-Glucoside FAB-MS (M + H) + 711 1 H-NMR δ (DMSO-d 6 ) TMS; 4.77 (d, J = 2.8Hz, 1H), 4.80
(d-like, 1H), 4.92 (d, J = 7.0Hz, 1H), 7.00 (d, J = 8.8Hz, 1
H), 7.08 (d, J = 8.7Hz, 2H), 7.52 (d, J = 8.7Hz, 2H), 7.94 (d, J
= 8.8Hz, 1H), 8.40 (s, 1H). 13 C-NMR δ (DMSO-d 6 ) TMS; 60.7, 62.9, 68.3, 69.7,
70.5, 70.7, 73.2, 73.2, 73.4, 75.7, 76.6, 77.0, 78.
6,78.7, 80.0, 100.3, 102.4, 109.0, 112.5, 115.0, 11
5.9, 116.8, 116.7, 122.8, 125.5, 126.3, 129.9, 153.
1, 156.1, 157.1, 161.1, 174.8.
【００２３】６″−Ｏ−グルコシルプエラリン FAB-MS (M+H)+ 5791 H-NMR δ(DMSO-d6) TMS ; 4.14(d,J=7.4Hz,1H), 4.80
(d,J=9.8Hz,1H),6.80(d,J=8.6Hz,2H), 6.99(d,J=8.8Hz,
1H),7.40(d,J=8.6Hz,2H), 7.94(d,J=8.8Hz,1H),8.34(s,
1H).13 C-NMR δ(DMSO-d6) TMS ; 60.7, 69.0, 69.7, 70.1,
70.4, 73.1,73.2, 76.3, 76.5, 78.2, 79.8, 102.8,10
9.0, 112.1, 114.9, 115.9, 116.6,116.7, 122.4, 123.
0, 126.4, 130.0,152.7, 156.1, 156.8, 160.9, 175.1.6 "-O-glucosylpuerarin FAB-MS (M + H) + 579 1 H-NMR δ (DMSO-d 6 ) TMS; 4.14 (d, J = 7.4Hz, 1H), 4.80
(d, J = 9.8Hz, 1H), 6.80 (d, J = 8.6Hz, 2H), 6.99 (d, J = 8.8Hz,
1H), 7.40 (d, J = 8.6Hz, 2H), 7.94 (d, J = 8.8Hz, 1H), 8.34 (s,
1H). 13 C-NMR δ (DMSO-d 6 ) TMS; 60.7, 69.0, 69.7, 70.1,
70.4, 73.1,73.2, 76.3, 76.5, 78.2, 79.8, 102.8,10
9.0, 112.1, 114.9, 115.9, 116.6, 116.7, 122.4, 123.
0, 126.4, 130.0, 152.7, 156.1, 156.8, 160.9, 175.1.
【００２４】３′−ヒドロキシプエラリン−４′−Ｏ−
グルコシド FAB-MS (M+H)+ 5951 H-NMR δ(DMSO-d6) TMS ; 4.73(d,J=7.1Hz,1H), 4.80
(d,J=9.8Hz,1H),6.92(dd,J=2.0Hz,8.6Hz,1H),6.98(d,J=
8.9Hz,1H), 7.08(d,J=2.0Hz,1H),7.14(d,J=8.6Hz,1H),
7.93(d,J=8.8Hz,1H),8.37(s,1H).13 C-NMR δ(DMSO-d6) TMS ; 60.8, 61.4, 69.8, 70.5,
70.7, 73.3,73.5, 75.9, 77.2, 78.8, 81.8, 102.4,11
2.7, 115.1, 115.3, 116.5, 116.7, 119.8,122.8, 126.
2, 126.8, 145.1, 146.4, 153.1,155.2, 161.3, 174.7.3'-hydroxypuerarin-4'-O-
Glucoside FAB-MS (M + H) + 595 1 H-NMR δ (DMSO-d 6 ) TMS; 4.73 (d, J = 7.1Hz, 1H), 4.80
(d, J = 9.8Hz, 1H), 6.92 (dd, J = 2.0Hz, 8.6Hz, 1H), 6.98 (d, J =
8.9Hz, 1H), 7.08 (d, J = 2.0Hz, 1H), 7.14 (d, J = 8.6Hz, 1H),
7.93 (d, J = 8.8Hz, 1H), 8.37 (s, 1H). 13 C-NMR δ (DMSO-d 6 ) TMS; 60.8, 61.4, 69.8, 70.5,
70.7, 73.3, 73.5, 75.9, 77.2, 78.8, 81.8, 102.4, 11
2.7, 115.1, 115.3, 116.5, 116.7, 119.8, 122.8, 126.
2, 126.8, 145.1, 146.4, 153.1, 155.2, 161.3, 174.7.
【００２５】６″−Ｏ−アピオシル−３′−ヒドロキシ
プエラリン FAB-MS (M+H)+ 5651 H-NMR δ(DMSO-d6+D2O)TMS ; 4.83(d,J=3.2Hz,1H),4.8
7(d-like,1H),6.82(d-like,1H),6.87(d-like,1H),7.02
(br.s,1H),7.04(d,J=8.9Hz,1H),7.99(d,J=8.9Hz,1H),8.
27(s,1H).13 C-NMR δ(DMSO-d6+D2O)TMS ; 63.5, 68.8, 70.8, 71.
4, 73.8, 74.0,76.4, 78.9, 79.3, 80.5, 109.5, 112.
8,115.8, 116.2, 117.1, 117.5, 120.9,123.7, 124.0,
127.3, 145.2, 145.6,153.6, 156.9, 161.6, 176.2.6 "-O-apiosyl-3'-hydroxypuerarin FAB-MS (M + H) + 565 1 H-NMR δ (DMSO-d 6 + D 2 O) TMS; 4.83 (d, J = 3.2Hz , 1H), 4.8
7 (d-like, 1H), 6.82 (d-like, 1H), 6.87 (d-like, 1H), 7.02
(br.s, 1H), 7.04 (d, J = 8.9Hz, 1H), 7.99 (d, J = 8.9Hz, 1H), 8.
27 (s, 1H). 13 C-NMR δ (DMSO-d 6 + D 2 O) TMS; 63.5, 68.8, 70.8, 71.
4, 73.8, 74.0, 76.4, 78.9, 79.3, 80.5, 109.5, 112.
8,115.8, 116.2, 117.1, 117.5, 120.9,123.7, 124.0,
127.3, 145.2, 145.6, 153.6, 156.9, 161.6, 176.2.
【００２６】実施例２ 表２の配合組成に従って、美白剤とイソフラボン配糖体
を表３、表４の組成で含有するクリーム（pH６．０）を
調製し、その連続塗布による美白効果について下記試験
により調べた。その結果を表５に示した。Example 2 A cream (pH 6.0) containing a whitening agent and an isoflavone glycoside in the composition shown in Tables 3 and 4 was prepared according to the composition of Table 2, and the following test was conducted for the whitening effect by continuous application thereof. Investigated by. The results are shown in Table 5.
【００２７】（ＵＶ−Ｂ誘導色素斑に対する美白効果試
験）被試験者２０名の上腕内側部にＵＶ−Ｂ領域の紫外
線を最小紅斑量の２倍量を１日１回２日間にわたり照射
し誘導した色素斑に、１日２回、１ケ月間被検部位に試
料を連続塗布することによる美白効果を調べた。評価
は、色差計（村上色彩製ＣＭＳ−１２００）を用いて測
定を行い、得られたマンセル値よりＬ*値を算出し、そ
の回復をあらわすΔΔＬ*値を用いた。尚、ΔΔＬ*値は
以下のように定義した。試料塗布開始直前の試料塗布被
験部位及び試料未塗布被験部位のＬ*値をそれぞれ
ＬO 、ＬO'、連続塗布１ケ月後の各々の部位のＬ*値を
それぞれＬ1、Ｌ1'としてΔΔＬ*は以下の式で表わし
た。(Whitening Effect Test on UV-B Induced Pigment Spots) 20 subjects to be examined were irradiated with UV rays in the UV-B region at twice the minimum erythema dose once a day for 2 days to induce the induction. The whitening effect obtained by continuously applying the sample to the tested spots twice a day for one month was examined. The evaluation was performed using a color difference meter (CMS-1200 manufactured by Murakami Color Co., Ltd.), the L * value was calculated from the obtained Munsell value, and the ΔΔL * value representing the recovery was used. The ΔΔL * value was defined as follows. Sample application test site and the sample uncoated test site L * value of each L O of the sample application immediately before, as L O ', each of the sites in the L * values after each successive coating 1 month L 1, L 1' ΔΔL * is expressed by the following formula.
【００２８】[0028]
【数１】ΔΔＬ*＝（Ｌ1−ＬO）−（Ｌ1'−ＬO'）## EQU1 ## ΔΔL * = (L 1 −L O ) − (L 1 '−L O ')
【００２９】また、評価は被試験者２０名の下記表１の
評価点の平均値で示した。The evaluation is shown by the average value of the evaluation points of the 20 test subjects in Table 1 below.
【００３０】[0030]
【表１】 [Table 1]
【００３１】[0031]
【表２】 [Table 2]
【００３２】[0032]
【表３】 [Table 3]
【００３３】[0033]
【表４】 [Table 4]
【００３４】[0034]
【表５】 [Table 5]
フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ａ６１Ｋ 7/00 Ｋ Ｘ 7/48 Continuation of front page (51) Int.Cl. 6 Identification code Office reference number FI Technical display area A61K 7/00 K X 7/48
Claims (3)
子を示し、Ｒ2 は水素原子又は水酸基を示し、Ｒ3 は水
素原子又はグルコシル基を示す）で表わされるイソフラ
ボン配糖体。1. The following general formula (1): (In the formula, R 1 represents an apiosyl group, a glucosyl group or a hydrogen atom, R 2 represents a hydrogen atom or a hydroxyl group, and R 3 represents a hydrogen atom or a glucosyl group).
有する化粧料。2. A cosmetic containing the isoflavone derivative according to claim 1.
体、コウジ酸類及び胎盤抽出物から選ばれる１種又は２
種以上と請求項１記載のイソフラボン誘導体とを含有す
る化粧料。3. One or two selected from ascorbic acids, hydroquinone derivatives, kojic acids and placenta extracts.
A cosmetic containing at least one species and the isoflavone derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30507393A JP3271840B2 (en) | 1993-12-06 | 1993-12-06 | Novel isoflavone glycosides and cosmetics containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP30507393A JP3271840B2 (en) | 1993-12-06 | 1993-12-06 | Novel isoflavone glycosides and cosmetics containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07157494A true JPH07157494A (en) | 1995-06-20 |
| JP3271840B2 JP3271840B2 (en) | 2002-04-08 |
Family
ID=17940793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP30507393A Expired - Fee Related JP3271840B2 (en) | 1993-12-06 | 1993-12-06 | Novel isoflavone glycosides and cosmetics containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3271840B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093411A (en) * | 1998-03-16 | 2000-07-25 | The Procter & Gamble Company | Compositions for regulating skin appearance |
| EP1057475A1 (en) * | 1999-06-04 | 2000-12-06 | Beiersdorf AG | Use of ascorbic acid and one or more flavone derivatives and/or flavanone derivatives particularly flavonoids for the preparation of cosmetic or dermatological compositions for preventing or relieving of sunburns |
| EP1205179A1 (en) * | 2000-11-10 | 2002-05-15 | L'oreal | Cosmetic composition comprising an aminophenol derivative and an isoflavonoid |
| JP2003002819A (en) * | 2001-06-22 | 2003-01-08 | Naris Cosmetics Co Ltd | Skin care composition |
| WO2003051864A1 (en) * | 2001-12-19 | 2003-06-26 | Novogen Research Pty Ltd | Isoflavonoid conjugates, compositions thereof and therapeutic methods involving same |
| KR100482355B1 (en) * | 2002-05-02 | 2005-04-14 | 주식회사 알로에마임 | Liposome or nanoemulsion containing dipalmitoyl hydroxyproline and soy isoflavone and a cosmetic composition containing the liposome and/or the nanoemulsion and method thereof |
| JP2006257015A (en) * | 2005-03-16 | 2006-09-28 | Maruzen Pharmaceut Co Ltd | New c-glycoside compound, collagen production promotor, skin cosmetic and beverage and food for beautification |
| JP2007106765A (en) * | 2005-10-11 | 2007-04-26 | L'oreal Sa | Use of c-glycoside compound for depigmenting human skin |
| JP2013540769A (en) * | 2010-10-13 | 2013-11-07 | 南京工▲業▼大学 | Fructosylated puerarin and its preparation and use |
| KR20210062861A (en) * | 2019-11-22 | 2021-06-01 | 오산대학교 산학협력단 | Composition of whitening containing Ipriflavone as inhibitor of PKA, cosmetic composition and pharmaceutical composition containing the same, and manufacturing method for the same |
-
1993
- 1993-12-06 JP JP30507393A patent/JP3271840B2/en not_active Expired - Fee Related
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6093411A (en) * | 1998-03-16 | 2000-07-25 | The Procter & Gamble Company | Compositions for regulating skin appearance |
| EP1057475A1 (en) * | 1999-06-04 | 2000-12-06 | Beiersdorf AG | Use of ascorbic acid and one or more flavone derivatives and/or flavanone derivatives particularly flavonoids for the preparation of cosmetic or dermatological compositions for preventing or relieving of sunburns |
| WO2000074641A1 (en) * | 1999-06-04 | 2000-12-14 | Beiersdorf Ag | Use of ascorbic acid and one or more flavone derivatives and/or flavan derivatives, especially flavonoids, for producing cosmetic or dermatological preparations used to prevent or sooth sunburns |
| EP1205179A1 (en) * | 2000-11-10 | 2002-05-15 | L'oreal | Cosmetic composition comprising an aminophenol derivative and an isoflavonoid |
| FR2816502A1 (en) * | 2000-11-10 | 2002-05-17 | Oreal | COSMETIC COMPOSITION CONSISTING OF AN AMINOPHENOL DERIVATIVE AND AN ISOFLAVONOIDE |
| JP2003002819A (en) * | 2001-06-22 | 2003-01-08 | Naris Cosmetics Co Ltd | Skin care composition |
| WO2003051864A1 (en) * | 2001-12-19 | 2003-06-26 | Novogen Research Pty Ltd | Isoflavonoid conjugates, compositions thereof and therapeutic methods involving same |
| KR100482355B1 (en) * | 2002-05-02 | 2005-04-14 | 주식회사 알로에마임 | Liposome or nanoemulsion containing dipalmitoyl hydroxyproline and soy isoflavone and a cosmetic composition containing the liposome and/or the nanoemulsion and method thereof |
| JP2006257015A (en) * | 2005-03-16 | 2006-09-28 | Maruzen Pharmaceut Co Ltd | New c-glycoside compound, collagen production promotor, skin cosmetic and beverage and food for beautification |
| JP2007106765A (en) * | 2005-10-11 | 2007-04-26 | L'oreal Sa | Use of c-glycoside compound for depigmenting human skin |
| JP2013540769A (en) * | 2010-10-13 | 2013-11-07 | 南京工▲業▼大学 | Fructosylated puerarin and its preparation and use |
| KR20210062861A (en) * | 2019-11-22 | 2021-06-01 | 오산대학교 산학협력단 | Composition of whitening containing Ipriflavone as inhibitor of PKA, cosmetic composition and pharmaceutical composition containing the same, and manufacturing method for the same |
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|---|---|
| JP3271840B2 (en) | 2002-04-08 |
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