JPS5899498A - Flavonol glucoside - Google Patents
Flavonol glucosideInfo
- Publication number
- JPS5899498A JPS5899498A JP19521681A JP19521681A JPS5899498A JP S5899498 A JPS5899498 A JP S5899498A JP 19521681 A JP19521681 A JP 19521681A JP 19521681 A JP19521681 A JP 19521681A JP S5899498 A JPS5899498 A JP S5899498A
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- water
- compound
- sophorosyl
- formula
- 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.)
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- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は式
で表わされる7ラボン誘導体に関するもので、ある。た
だし、RIはソホロシル基、グルコシル基または水素を
意味し、−および狗は一方が水素を、他方が7エルロイ
ル基を意味する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a 7-rabone derivative represented by the formula: However, RI means a sophorosyl group, a glucosyl group, or hydrogen, and one of "-" and "dog" means hydrogen and the other means a 7-eruroyl group.
さらに詳しくは9本発明は0−78ルロイルグルコシル
ケン7エロールおよびその8−0−グルコシルもしくは
ソホロシル誘導体に関するものである。More specifically, the present invention relates to 0-78 luroylglucosilkene 7erol and its 8-0-glucosyl or sophorosyl derivatives.
これらの化合物はニラの抽出物から得られ。These compounds are obtained from chive extract.
あるいはこれを原料として加熱、酵素処理、酸処理等の
処理手段により得ることができ、線溶誘導活性および/
または抗アレルギー作用を有し医薬として期待される。Alternatively, it can be obtained as a raw material by treatment means such as heating, enzyme treatment, acid treatment, etc., and the fibrinolytic inducing activity and/or
It also has anti-allergic effects and is expected to be used as a medicine.
ニラ(AAlllu tuberosum Rottl
)は、広く食用に供されているが、その薬理作用につ
いては殆んど知られていない。漢方ではその種子が白色
帯下、頻尿らに用いられることもあるが、その葉茎部は
全く用いられていない。またニラの成分研究も少なく、
含硫黄揮発性物質が数種知られているが、その他の成分
に関してはこれまでに殆んど報告が見られない。Chive (AAllu tuberosum Rottl)
) are widely eaten, but little is known about their pharmacological effects. In Chinese medicine, the seeds are sometimes used to treat leucorrhoea and frequent urination, but the leaves and stems are not used at all. There is also little research into the ingredients of chives.
Although several types of sulfur-containing volatile substances are known, there have been few reports regarding other components.
本発明者らは、ニラの葉茎部の抽出エキスから線溶誘導
作用および/または抗アレルギー作用をもつ新規7ラボ
ノイドを単離し、7ラボノイドムと命名した。7ラボノ
イドAの構造は。The present inventors isolated a novel 7-rabonoid having fibrinolysis-inducing and/or anti-allergic activity from an extract of the leaf and stem of chive, and named it 7-rabonoid. 7 What is the structure of Lavonoid A?
ケンフェロール(kaesipharol )骨格を有
し、その8位にソホロース(sophoroge )
、また7位に2−7エルロイルグルコース(2−fer
uloyl glu−cosa )の結合したものであ
る。It has a kaesipharol skeleton, with sophorose at the 8th position.
, and 2-7 eruroylglucose (2-fer
uloyl glu-cosa).
7ラボノイドム水溶液を加熱することによりフェルロイ
ル基が2位から6位に転位した7ラボノイドBが得られ
、またこの7ラボノイドBを希酸で加水分解すると8位
ソホロースの脱離した7ラボノイドCが得られた。また
、7ラボノイドムを希酸で加水分解すれば、8位ソホロ
ースの血離した7ラボノイドDが得られ、さらに、7ラ
ボノイドAをヘスペリジナーゼで酵素分解することによ
り、8位ソホロースから1個のグルコースの脱離した7
ラボノイド!が得られた。これらの化合物は、いづれも
薬理活性を有し、かつ新規物質である。By heating an aqueous solution of 7-rabonoid, 7-rabonoid B with the feruloyl group rearranged from the 2-position to the 6-position is obtained, and when this 7-rabonoid B is hydrolyzed with a dilute acid, 7-rabonoid C with the sophorose at the 8-position eliminated is obtained. It was done. In addition, by hydrolyzing 7-lavonoidome with dilute acid, 7-labonoid D, which is separated from sophorose at position 8, is obtained.Furthermore, by enzymatically decomposing 7-lavonoid A with hesperidinase, one glucose is removed from sophorose at position 8. 7 who left
Labonoid! was gotten. All of these compounds have pharmacological activity and are new substances.
7ラボノイドAを得るには、ニラの葉茎部を新鮮のま\
あるいは乾燥したのち、水または含ま
水有機溶媒で抽出する。葉茎部はそのま^抽出してもよ
いが、抽出効率を高めるために切断または粉砕して用い
る方が望ましい。抽出溶媒は水のみよりも、それに適量
の有機溶媒2例えばメタノール、エタノール、プロパツ
ールなどのアルコ−“ル、ア七トン、ジオキサンなどを
添加した混合溶媒の方が抽出効率が良い。またベンゼン
、ヘキサンなどでクリロフィルなどの色素を除去したの
ち、水で抽出する方法でも良い。7 To obtain rabonoid A, use fresh chive leaves and stems.
Alternatively, after drying, extract with water or a water-containing organic solvent. The leaves and stems may be extracted as they are, but it is preferable to cut or crush them before use to increase extraction efficiency. As the extraction solvent, a mixed solvent containing an appropriate amount of an organic solvent 2 such as methanol, ethanol, alcohol such as propatool, acetate, dioxane, etc. is better than water alone.Also, benzene, A method of removing pigments such as chrylophyll with hexane or the like and then extracting with water may also be used.
ただし、いづれの溶媒を用いる場合でも、7ラボノイド
Aが熱に対して不安定であるため、抽出温度は室温以下
であることが望ましい。例えば、新鮮二う葉茎部を3乃
至5倍量の80−メタノールと室温8〜6日冷浸したの
ち、濾過して抽出液を得る。However, no matter which solvent is used, it is desirable that the extraction temperature be below room temperature because 7-rabonoid A is unstable to heat. For example, a fresh leaf stalk is soaked in 3 to 5 times the amount of 80-methanol at room temperature for 8 to 6 days, and then filtered to obtain an extract.
抽出液から7ラボノイドムを分離精製するには一般の天
然物の単一に用いられる公知の手段を適宜組合せて行う
ことができる。すなわち。Separation and purification of the 7-rabonoidome from the extract can be carried out by appropriately combining known means used for general natural products. Namely.
非極性多孔性ポリマー、デキストランゲル類。Non-polar porous polymers, dextran gels.
活性炭、lリアミド類やシリカゲル類を用いた吸着クロ
マトグラフィーや分配クロマトグラフィーが適用できる
。また、これらのクロマトグラフィーを高速液体クロマ
トグラフィー装置ヲ用いて行うこともできる。さらに必
要によりブタノールなど適当な笹媒を用いて再結晶する
こともできる。Adsorption chromatography or partition chromatography using activated carbon, lyamides, or silica gels can be applied. Moreover, these chromatography can also be performed using a high performance liquid chromatography apparatus. Furthermore, if necessary, recrystallization can be performed using a suitable bamboo medium such as butanol.
7ラボノイドムは新規物質であり1次の理化学的性質を
有する。7 Lavonoidom is a new substance and has first-order physical and chemical properties.
イ)性状:S−ブタノール−エタノールから再結晶した
とき、一点ZOO〜Sll”Cの淡黄褐色粉末品を与え
る。b) Properties: When recrystallized from S-butanol-ethanol, a pale yellowish brown powder product of ZOO~Sll''C is obtained.
→元素分析
計算値(c43H4・024・H2O)0 6B、1%
、 H51B1%
実測値
0 6B、2?%、H4,98%
ハ)呈色反応
塩酸マグネシウム反応、塩化第二鉄反応に陽性、ニンヒ
ドリン反応、ドラーゲンドルフ反応に陰性。→ Elemental analysis calculation value (c43H4・024・H2O) 0 6B, 1%
, H51B1% Actual value 0 6B, 2? %, H4, 98% c) Color reaction Positive for magnesium hydrochloride reaction and ferric chloride reaction, negative for ninhydrin reaction and Dragendorff reaction.
副索外部吸収スペクトル
λR−Hd(logg ) : 2BB (4,86L
246III龜X
(4J? )t 269 (4,81)、 88B (
4,42)λ”H−AIC” am (log g )
= 284 (4,85) 。Secondary cable external absorption spectrum λR-Hd (logg): 2BB (4,86L
246III 龜X (4J?)t 269 (4,81), 88B (
4,42) λ”H-AIC” am (log g)
= 284 (4,85).
墓1Lx
878(4,86)、80!(44B)、889(4,
813,899(4,08)
2””−””IC′511(log i ) : 24
B (4,58) 。Grave 1Lx 878 (4,86), 80! (44B), 889(4,
813,899(4,08) 2""-""IC'511(log i): 24
B (4,58).
ax
!68 (4,50>t 888 (4,60)λ””
−”0A0slI(1og g ) ! iB 8 B
(4,86) 。ax! 68 (4,50>t 888 (4,60)λ””
-”0A0slI(1og g)! iB 8 B
(4,86).
―亀X
247 (4J6 L 268 (4,Z9 L
8BB(4,41)
ホ)赤外線吸収スペクトル
へ)マススペクトル
FD−Maw/z:118B、 1119. 987
(M”+K)、971(M”+Na)、95?、8
09゜795.668,647,688,487.47
1゜ト)溶解性
水に易溶、ジメチルホルムアミド、ジメチルスルホキサ
イドに可溶、エタノール、メタノール、クロロホルム、
アセトン、ベンゼン。- Turtle X 247 (4J6 L 268 (4,Z9 L
8BB(4,41) e) To infrared absorption spectrum) Mass spectrum FD-Maw/z: 118B, 1119. 987
(M”+K), 971 (M”+Na), 95? , 8
09°795.668,647,688,487.47
1°) Solubility Easily soluble in water, soluble in dimethylformamide, dimethyl sulfoxide, ethanol, methanol, chloroform,
Acetone, benzene.
エーテル、酢酸エチルに難溶。Slightly soluble in ether and ethyl acetate.
チ)核磁気共鳴xペク)ルー(SOOMHz、DM80
−<ls −Dzo )δppm (JHz ) ”8
.80 (8H,s) 4.66(1M、 e
i、 J−Fl)4.9 ? (IH,t、 J−8)
5.46(IH,d、 J−8)5−69 (l
H1brei−J−8) 6−41 (l Hs ’
! )6.50(IH,1,J−16) 6.80(
IH,!l)6.88 (1)1. d、 J−8)
6J 5(tlH,(1,J−8)?、16(IH,
a、J−8) 7.81(IH,8)7.64 (L
H,(1,J−16) 8.11 (2H,d、 J
−8)す)酸分解物
IN−塩酸中、100°C,5時間加水分解したとき、
ケンフェロールおよびグルコースを生成する。h) Nuclear magnetic resonance x Baek) Lu (SOOMHz, DM80
−<ls −Dzo ) δppm (JHz) ”8
.. 80 (8H, s) 4.66 (1M, e
i, J-Fl) 4.9? (IH, t, J-8)
5.46 (IH, d, J-8) 5-69 (l
H1brei-J-8) 6-41 (l Hs'
! ) 6.50 (IH, 1, J-16) 6.80 (
IH,! l) 6.88 (1)1. d, J-8)
6J 5(tlH, (1, J-8)?, 16(IH,
a, J-8) 7.81 (IH, 8) 7.64 (L
H, (1, J-16) 8.11 (2H, d, J
-8) S) Acid decomposition product IN - When hydrolyzed in hydrochloric acid at 100°C for 5 hours,
Produces kaempferol and glucose.
ヌ)アルカリ分解物
1%力セイカリ水溶液中、室温、15時間加水分解した
とき、7!ルラ酸を生成する。n) Alkaline decomposition product When hydrolyzed in 1% aqueous alkaline solution at room temperature for 15 hours, 7! Produces lulic acid.
ル)糖のメチル化分析
アルジトールアセテート法により、 8,4.6−トリ
メチルグルコース1.00モルに対シ。) Methylation analysis of sugars per 1.00 mol of 8,4,6-trimethylglucose using the alditol acetate method.
2、8.4.6−チトラメチルグルコースを1.97モ
ル検出した。1.97 mol of 2,8.4.6-titramethylglucose was detected.
上記の理化学的性質から、7ラボノイドムの構造式は、
下記のごとく推定された。すなわち7ラポノイドAは8
−0−β−D−ソホロシルー7−0−β−D−(2’−
0−)、ルロイル)グルコシルケンフ!p−ルである。From the above physical and chemical properties, the structural formula of the 7-labonoidome is:
It was estimated as follows. That is, 7 laponoid A is 8
-0-β-D-sophorosyl7-0-β-D-(2'-
0-), Leroyil) Glucosyl kemp! It is p-le.
ド真水溶液を加熱すればよい。水溶液のpHは中性附近
もしくはアルカリ性であることが必要で、酸性側のpH
では転位反応が起り難い。ただし、アルカリ側のpHで
は、7エルロイル基の脱離などの副反応を助長するので
好ましくない。また反応温度は室温乃至ioo℃の間の
いづれを選んでもよいが、低温では9反応の進行が遅い
ため、80乃至100℃の範囲が望ましい。7ラボノイ
ドBの生成は1反応時間に比例して増加するが、10時
間以上の長時間では副反応が起るので、好ましくは2乃
至5時間の反応時間が適当である。反応液から7ラボノ
イドBを得るには反応液を氷冷し、生ずる沈でんを集メ
、 含水アルコールなどの溶媒から再結晶すればよい。All you have to do is heat the fresh water solution. The pH of the aqueous solution needs to be around neutral or alkaline, and the pH of the aqueous solution should be on the acidic side.
In this case, rearrangement reaction is difficult to occur. However, a pH on the alkaline side is not preferable because it promotes side reactions such as elimination of the 7-eruroyl group. Further, the reaction temperature may be selected from room temperature to 100°C, but is preferably in the range of 80 to 100°C since the progress of the 9 reaction is slow at low temperatures. Although the production of 7-rabonoid B increases in proportion to the reaction time, a reaction time of 2 to 5 hours is preferable since side reactions occur if the reaction time is longer than 10 hours. In order to obtain 7-rabonoid B from the reaction solution, the reaction solution may be cooled on ice, the resulting precipitate may be collected, and recrystallized from a solvent such as hydrous alcohol.
7ラボノイードBは以下の理化学的性質を有することか
ら、7ラボノイド真のiL位7エルロイル基が6位に転
位した構造であると推定された。Since 7-Labonoid B has the following physical and chemical properties, it was estimated that it has a structure in which the 7-Eluroyl group at the iL position of the 7-Labonoid is rearranged to the 6-position.
イ)性状=50襲メタノールから再結晶したとき融点z
14〜217℃の微黄色針状晶を与える。b) Properties = melting point z when recrystallized from 50% methanol
Gives pale yellow needles at 14-217°C.
口)元素分析
計算値(Cn5HasO244H20)0 1a、44
%、 H5,81% −実測値
0 62.88%、 )1 6.09%ハ)溶解性
アルカリ性水溶液、ジメチルホルムアミドお−よびジメ
チルスルホキサイドに易溶、エタノールに可溶、水およ
びベンゼン、酢酸エチル。mouth) Elemental analysis calculated value (Cn5HasO244H20) 0 1a, 44
%, H5, 81% - Actual value 0 62.88%, ) 1 6.09% c) Soluble Alkaline aqueous solution, easily soluble in dimethylformamide and dimethyl sulfoxide, soluble in ethanol, water and benzene, Ethyl acetate.
エーテル、メタノールなどに難溶。Slightly soluble in ether, methanol, etc.
二)紫外線吸収スペクトル
KtOH
λ w(logg) :28B(4,81)t 24
7IIaX
(4,21)、 268 (4,2幻、88B(4,8
8)λ″″toH+A10”sm(logg) :
Z 8 5 (4,8OLaX
!79(4,28L 80B(4,16)、888(4
,80)、 896 (8J4 )λItO)))−N
aOAc
mix sa(logg) : 2 B 4 (
449) 。2) Ultraviolet absorption spectrum KtOH λ w (logg): 28B(4,81)t 24
7IIaX (4,21), 268 (4,2 illusion, 88B (4,8
8) λ″″toH+A10″sm (logg):
Z 8 5 (4,8OLaX!79(4,28L 80B(4,16), 888(4
,80), 896 (8J4)λItO)))-N
aOAc mix sa(logg): 2 B 4 (
449).
248(4,1?)、168(4,19)、8B4(4
,81)
ホ) 赤外i吸収スペクトル
y””cwl−”: 8400.1655.1600.
1080ax
へ)マススペクトル
FD−M8 11/!W : 987 (M”+K L
9? 1(M”+Na)、8(DI、795,668
,681ト)核磁気共鳴スペクトル(200MHK、
DM80−<1s−DzO)δppm (JHz )
:8.80 (8H,g ) 4.21 (I
H,da、 J−12,8)4.5、J(IH,J−I
J) 4.66(IH,d、J−8)6.18(I
H,a、−J−8) 5.70(1)1.b惰J−8
)6.47(IH,!、J−16) 6.55(IH
,s)6.81(LH,+1.J−8) 6.85(
LH,1m)6.98(81(、d、 J−8) 7
.08(IH,d、 J−83?J?(IH,8)
7.59(IH,d、J−16)8.1 B
(2H,(1,J−8)
7ラボノイドCは、7ラボノイドBの部分加水分解によ
って得られる。7ラポノイドのグルコサイドは結合位置
により酸加水分解に対する抵抗性が興なることは公知(
例えば、 J、B。248 (4,1?), 168 (4,19), 8B4 (4
, 81) e) Infrared i absorption spectrum y""cwl-": 8400.1655.1600.
To 1080ax) Mass Spectrum FD-M8 11/! W: 987 (M”+K L
9? 1 (M”+Na), 8 (DI, 795,668
, 681) Nuclear magnetic resonance spectrum (200MHK,
DM80-<1s-DzO) δppm (JHz)
:8.80 (8H,g) 4.21 (I
H, da, J-12, 8) 4.5, J (IH, J-I
J) 4.66 (IH, d, J-8) 6.18 (I
H, a, -J-8) 5.70 (1) 1. bina J-8
) 6.47 (IH,!, J-16) 6.55 (IH
,s) 6.81(LH,+1.J-8) 6.85(
LH, 1m) 6.98 (81 (, d, J-8) 7
.. 08 (IH, d, J-83?J? (IH, 8)
7.59 (IH, d, J-16) 8.1 B
(2H, (1, J-8) 7 Laponoid C is obtained by partial hydrolysis of 7 Laponoid B. It is known that the glucoside of 7 Laponoid has resistance to acid hydrolysis depending on the bond position (
For example, J, B.
Harborne、 Phytochem+1stry
it 107 (1’965年))であり、7位グル
コサイドを残し、8位グルコサイドのみを選択的に加水
分解することができる。この方法を適用して、7ラボノ
イドBから得た7ラボノイドCの理化学的性質は表1に
示した。Harborne, Phytochem+1try
it 107 (1'965)), and can selectively hydrolyze only the glucoside at the 8-position while leaving the glucoside at the 7-position. The physicochemical properties of 7-rabonoid C obtained from 7-rabonoid B by applying this method are shown in Table 1.
7ラボノイドDは、同様にして、7ラボノイドムの8位
グルコサイドを部分加水分解して得られ、その理化学的
性質は表1に示し、た。7-Labonoid D was similarly obtained by partially hydrolyzing the 8-position glucoside of 7-Labonoid, and its physicochemical properties are shown in Table 1.
7ラボノイドXは、7ラボノイドAの8位ソホp−スの
非還元末端のグルコースのみを選択的に加水分解する方
法1例えばヘスペリジナ−ゼを用いる酵素分解で得るこ
とができる。7ラボノイド!の理化学的性質は表1に示
した。7-lavonoid 7 Labonoid! The physical and chemical properties of are shown in Table 1.
表17ラボノイドO,Dおよび2の理化学的性質
7ラボノイドム、B、O,Dおよび2の線溶誘導活性お
よび抗アレルギー活性を試験した結果を表2に示した。Table 17 Physical and chemical properties of rabonoids O, D, and 2 7 Table 2 shows the results of testing the fibrinolytic inducing activity and antiallergic activity of rabonoids B, O, D, and 2.
表27ラボノイドム、 B、 O,Dおよび冨の薬理活
性
注1)ラットに検体を静脈内投与し、10分後援血した
血液のニーグロブリン溶解時間を測定し、投与前のそれ
と比較して、投与前/投与後×100(4)士標準誤差
で示した。一群8匹。Table 27 Pharmacological activities of Lavonoidom, B, O, D, and Tomi Note 1) The specimen was administered intravenously to rats, and the niglobulin dissolution time of the blood that was sponsored for 10 minutes was measured and compared with that before administration. Before/after administration x 100(4) standard error. 8 animals per group.
注2)う、)POA反応(抗卵白アルブミンラ。Note 2) U,) POA reaction (anti-ovalbumin la.
ト血清を感作後48時間惹起)の抑制率で示した。抑制
率は各群の色素漏出面積から次式により求めた。一群5
匹。The inhibition rate was expressed in 48 hours after sensitization with human serum. The inhibition rate was calculated from the dye leakage area of each group using the following formula. Group 5
A fish.
抑制率(4)−(対照群−投薬群)/対照群±標準誤差
注8)5119/119投与
注43g119/J投与
注5)ジナトリウムクロモグリケート
実施例1
ニラの集綿(湿重量S、0I9)を粉砕し、80襲メタ
ノールt、htで室温にて6日間抽出した。Inhibition rate (4) - (control group - medication group) / control group ± standard error Note 8) 5119/119 administration Note 43g119/J administration Note 5) Disodium cromoglycate Example 1 Chive cotton collection (wet weight S , 0I9) was ground and extracted with 80 rounds of methanol at room temperature for 6 days.
濾過後、濾液からメタノールを留去し、得られた水溶液
を多孔性樹脂(三菱化成製ダイヤイオンHP−20)1
.01f)カラムに通過させ、水81で洗浄した。つぎ
に80%メタノール11で溶離する部分を集め、濃縮乾
固して、濃褐色粉末が14.Oj得た。After filtration, methanol is distilled off from the filtrate, and the resulting aqueous solution is treated with porous resin (Diaion HP-20 manufactured by Mitsubishi Kasei) 1
.. 01f) Passed through a column and washed with water 81. Next, the fraction eluted with 80% methanol 11 was collected and concentrated to dryness to give a dark brown powder 14. I got Oj.
この粉末9.0gをlθ%メタノールllに溶かし、1
0%メタノールで充填した=HP−20(1,Oj)カ
ラムにかけた。カラムをlogメタノール11,50%
メタノール11で洗浄後80%メタノール21で溶離す
る部分を集め。Dissolve 9.0 g of this powder in 1 liter of lθ% methanol,
Applied to =HP-20(1,Oj) column packed with 0% methanol. log column methanol 11,50%
After washing with methanol 11, the portion eluted with 80% methanol 21 was collected.
濃縮乾固すれば、茶褐色粉末がL489得られた。When concentrated to dryness, L489 was obtained as a brown powder.
つぎにこの粉末1.609を60%メタノール80−に
溶かし、逆相系シリカゲル(東洋曹達製78に−GKL
LS−4100DSi9IL)(IXl1インチ)カラ
ムを用いて高速液体クロマト装置による分取を行った。Next, this powder 1.609 was dissolved in 60% methanol 80- and dissolved in reverse-phase silica gel (Toyo Soda 78-GKL).
Fractionation was performed using a high performance liquid chromatography device using a LS-4100DSi9IL (IX1 1 inch) column.
溶媒は60%メタノール、流速は14gLt/分、サン
プルの注入量は毎回8−とじ、紫外部2645m に
よって検出した。活性画分として保持時間6ないし8分
の部分を分取し、濃縮乾固して0.509の茶褐色粉末
を得た。The solvent was 60% methanol, the flow rate was 14 gLt/min, the sample injection amount was 8-fold each time, and detection was performed by ultraviolet light at 2645 m2. A portion with a retention time of 6 to 8 minutes was collected as an active fraction and concentrated to dryness to obtain a brown powder of 0.509.
さらに、精製するために再びLS−410カラムにかけ
た。すなわち、この粉末846■を459&メタノール
17.8−に溶かし、LS−410カラム(IXIIイ
ンチ)を接属した高速液体クロマト装置により分画した
。46弾メタノールを流速14@t/mllで流し、1
8ないし21分の保持時間で溶出する活性画分を集めt
濃縮乾固すれば淡褐色粉末が44m9得られた。Furthermore, it was applied to an LS-410 column again for purification. That is, 846 ml of this powder was dissolved in 459 ml of methanol and 17.8 ml of methanol, and fractionated using a high performance liquid chromatograph equipped with an LS-410 column (IXII inch). 46 bullet methanol was flowed at a flow rate of 14@t/ml,
Collect active fractions eluting at retention times of 8 to 21 minutes.
Concentration to dryness yielded 44 m9 of light brown powder.
この粉末を襲−ブタノール−エタノールの混合溶媒から
再結晶し、7ラボノイドAを淡黄褐色粉末品として得た
。This powder was recrystallized from a mixed solvent of butanol and ethanol to obtain 7-rabonoid A as a pale yellowish brown powder.
実施例2
7ラボノイドムl(1”9をpH7,0のリン酸緩衡液
1O69−に溶解し、沸騰水浴上で8時間加熱した。−
晩冷蔵庫内に放置し、生じた沈殿を遠心分離した。沈殿
は水5sa/で洗浄後、50%メタノールで再結晶し、
微黄色針状晶の7ラボノイドBを55■得た。Example 2 7 ml of rabonoid (1"9) was dissolved in 1O69 of phosphate buffer pH 7.0 and heated on a boiling water bath for 8 hours.
The mixture was left in the refrigerator overnight, and the resulting precipitate was centrifuged. The precipitate was washed with 5 sa/ml of water and then recrystallized with 50% methanol.
55 μ of 7-Labonoid B in the form of pale yellow needle-like crystals were obtained.
実施例8
7ラボメイド840■を2.5s硫酸の50%エタノー
ル溶液l〇−中で100分間加熱還流した。反応液を酢
酸エチルで抽出し、酢酸エチル相を水洗、乾燥後、濃縮
乾固した。得られた黄色粉末をエタノールから再結晶す
れば、黄色針状晶の7ラボノイドclBN9が得られた
。Example 8 7 Labomade 840■ was heated under reflux for 100 minutes in a 2.5 s solution of sulfuric acid in 50% ethanol. The reaction solution was extracted with ethyl acetate, and the ethyl acetate phase was washed with water, dried, and then concentrated to dryness. When the obtained yellow powder was recrystallized from ethanol, yellow needle-like crystals of 7-lavonoid clBN9 were obtained.
実施例会
7ラボノイドA30119を5%硫a!8−に溶解し、
沸騰水浴上で100分間加熱した。冷却後生じた黄色沈
殿をエタノールから再結晶して。Example meeting 7 Labonoid A30119 with 5% sulfur a! 8- dissolved in
Heat on boiling water bath for 100 minutes. After cooling, the yellow precipitate formed was recrystallized from ethanol.
黄色粉末品のフラボノイドD10169を得た。Flavonoid D10169 was obtained as a yellow powder.
実施例5
7ラボノイドA100wkgをpH4のクエン酸−リン
酸緩衝液z5−中で可溶性へスペリジナーゼ(田辺)2
00■を用い87℃で40時間酵素分解した。冷却後生
じた沈殿を十分に水洗し、黄色粉末品の7ラポノイドに
61”9を得た。Example 5 7 Labonoid A 100 wkg was soluble in hesperidinase (Tanabe) 2 in citrate-phosphate buffer pH 4.
Enzymatic digestion was carried out using 00■ at 87°C for 40 hours. After cooling, the resulting precipitate was thoroughly washed with water to obtain 7 Laponoid 61''9 as a yellow powder.
Claims (1)
、&および&は一方が水素を、他方が7エルロイル基を
あられす。)であられされる7ラボン誘導体。 (g)s−o−β−D−ソホロシルー7−0−β−D−
(!’−0−フェルロイル)−グルコシルケン7!ロー
ルである特許請求の範囲第一項記載の化合物。 (8) 8−0−β−O−ソホロシルー7−〇−β−D
−(6’−0−7エルロイル)−グルコシルケン7!ロ
ールである特許請求の範囲第一項記載の化合物0[Scope of Claims] (In the formula, R1 is a sophorosyl group, a glucosyl group, or hydrogen, & and & are each hydrogen and the other is a 7-eruroyl group.) (g) so-β-D-sophorosyl-7-0-β-D-
(!'-0-feruloyl)-glucosilkene 7! The compound according to claim 1, which is a role. (8) 8-0-β-O-sophorosyl-7-〇-β-D
-(6'-0-7 Elroyl)-Glucosilkene 7! Compound 0 according to claim 1, which is a role
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19521681A JPS5899498A (en) | 1981-12-04 | 1981-12-04 | Flavonol glucoside |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP19521681A JPS5899498A (en) | 1981-12-04 | 1981-12-04 | Flavonol glucoside |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5899498A true JPS5899498A (en) | 1983-06-13 |
JPS6365075B2 JPS6365075B2 (en) | 1988-12-14 |
Family
ID=16337389
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP19521681A Granted JPS5899498A (en) | 1981-12-04 | 1981-12-04 | Flavonol glucoside |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5899498A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859488A (en) * | 1987-09-15 | 1989-08-22 | Kabushiki Kaisha Yakult Honsha | Liquid food for curing constipation: polydextrose and oligosaccharide |
WO1997001343A2 (en) * | 1995-06-28 | 1997-01-16 | Institut Français Du Petrole | Utilization of sophorolipids as therapeutically active substances or cosmetic products, in particular for the treatment of the skin |
US5627157A (en) * | 1989-06-03 | 1997-05-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-glycosyl hesperidin and its uses |
-
1981
- 1981-12-04 JP JP19521681A patent/JPS5899498A/en active Granted
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859488A (en) * | 1987-09-15 | 1989-08-22 | Kabushiki Kaisha Yakult Honsha | Liquid food for curing constipation: polydextrose and oligosaccharide |
US5627157A (en) * | 1989-06-03 | 1997-05-06 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | α-glycosyl hesperidin and its uses |
WO1997001343A2 (en) * | 1995-06-28 | 1997-01-16 | Institut Français Du Petrole | Utilization of sophorolipids as therapeutically active substances or cosmetic products, in particular for the treatment of the skin |
WO1997001343A3 (en) * | 1995-06-28 | 1997-03-13 | Inst Francais Du Petrole | Utilization of sophorolipids as therapeutically active substances or cosmetic products, in particular for the treatment of the skin |
Also Published As
Publication number | Publication date |
---|---|
JPS6365075B2 (en) | 1988-12-14 |
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