JPS5953497A - Glycerin glycoside - Google Patents
Glycerin glycosideInfo
- Publication number
- JPS5953497A JPS5953497A JP57163685A JP16368582A JPS5953497A JP S5953497 A JPS5953497 A JP S5953497A JP 57163685 A JP57163685 A JP 57163685A JP 16368582 A JP16368582 A JP 16368582A JP S5953497 A JPS5953497 A JP S5953497A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- water
- solvent
- glycoside
- group shown
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Medicines Containing Plant Substances (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は植物に対する抗菌、抗ウィルス剤、昆虫や野ね
ずみ等の摂食阻害剤、41t1物の生長抑制剤などとし
て使用される下記一般式(1)で示される新規グリセリ
ン配糖体に関する。Detailed Description of the Invention The present invention provides a novel glycerin represented by the following general formula (1) that is used as an antibacterial and antiviral agent for plants, a feeding inhibitor for insects and field mice, a growth inhibitor for 41t1, etc. Concerning glycosides.
(但し、R1け了セチル基又は
J11
を示し、R2に水素Jル子又は
OH
を示すが、R1及びR2の少なくも一つはOH
であり、R3水酸基を示す。)
従来、グリセリンにグルコースが結合したグリセロール
グルコサイト9は知られているが、本発明者らはホソパ
ハカタユリの鱗茎等を用い、これを抽出2分画すること
により、グリセリンにフェノール性化合物が付加した前
記(1)式で示されるグリセロールグルコサイドが得ら
れると共に、これが新規物質であり、かつこの化合物が
植物に対する抗菌、抗ウィルス剤などとして有効に使用
されることを知見し、本発明をなすに至ったものである
。(However, R1 represents a cetyl group or J11, and R2 represents hydrogen or OH, but at least one of R1 and R2 is OH, and R3 represents a hydroxyl group.) Conventionally, glycerin contains glucose. Although bound glycerol glucosite 9 is known, the present inventors extracted and fractionated it into two fractions using the scales of Hosopahaca lily, etc., and thereby obtained the compound represented by the above formula (1) in which a phenolic compound is added to glycerin. The inventors have discovered that glycerol glucoside is obtained, that this is a new substance, and that this compound can be effectively used as an antibacterial and antiviral agent for plants, leading to the present invention.
以下、本発明につき更に詳しく説明する。The present invention will be explained in more detail below.
本発明に係る新規グリセリン配糖体は、前記一般式(1
)で示される化合物であり、これらの仕合’I’rr)
を具体的に例示すると、式(2)
で示される化合物(1−0−/?シラーマリルー3−0
−β−D−グルコピラノシルグリセロール)及び式(3
)
で示される化合物(1−o−zfラークマリル−2−〇
−β−D−グリコピラノシルー3−アセチルグリセロー
ル)などが挙げられる。The novel glycerin glycoside according to the present invention has the general formula (1
), and these combinations 'I'rr)
To specifically illustrate, the compound represented by the formula (2) (1-0-/?Silamaryl-3-0
-β-D-glucopyranosylglycerol) and formula (3
) (1-o-zf lacmaryl-2-〇-β-D-glycopyranosyl-3-acetylglycerol) and the like.
これらの化合物はいずれも苦味を有する物質で、ペンチ
ノン試薬に対して陽性である。All of these compounds have a bitter taste and are positive for the pentynon reagent.
本発明の新規グリセリン配糖体は、例えに1゛ホソノ々
ハカタユリ(Lillum regale Wllso
n)、タカサゴユリ(Ll目um formosanu
m Wall)等の全草、好適には鱗茎を用い、これを
水、メタノール、ブタノール、含水メタノール、含水エ
タノール等の抽出溶媒を使用して室温下もしくは加熱下
に抽出を行ない、その抽出液を水不溶性有機溶媒と水と
の分配溶媒を用いて分配し、更に分取した水層を水tf
t溶性有機溶媒を用いて分配することにより得られる水
難溶性有機溶媒層をカラムクロマトグラフィーに付し、
その苦味画分を採取することにより、得ることができる
。この場合、水不溶性有機溶媒トシてはクロロホルム、
エチルエーテル、塩化メチレン、酢酸エチル、ベンゼン
等が用いられる。The novel glycerin glycoside of the present invention can be obtained from, for example, 1.
n), Japanese lily (Ll order um formosanu)
Using the whole plant (preferably the bulb) such as M Wall), extract the whole plant using an extraction solvent such as water, methanol, butanol, aqueous methanol, or aqueous ethanol at room temperature or under heat, and then extract the extract. A water-insoluble organic solvent and water are distributed using a distribution solvent, and the separated aqueous layer is divided into water
The slightly water-soluble organic solvent layer obtained by partitioning using a t-soluble organic solvent is subjected to column chromatography,
It can be obtained by collecting its bitter fraction. In this case, the water-insoluble organic solvent is chloroform,
Ethyl ether, methylene chloride, ethyl acetate, benzene, etc. are used.
また、水離溶性有機溶媒としてはブタノール、アミルア
ルコール、ヘキシルアルコールなトカ用いられる。Further, as the water-soluble organic solvent, butanol, amyl alcohol, and hexyl alcohol are used.
寸だ、カラムクロマトグラフィーとしてはシリカゲル゛
カラムクロマトグラフィーが好オしく、使用する溶出溶
媒としては塩化メチレン−メタノール、酢酸エチル−エ
タノール、クロロホルム−エタノール、アセトン、酢酸
エチル、ペンl:’ 7−1タノール、ベンゼン−エタ
ノール等がHシ)C,) f+る。As for column chromatography, silica gel column chromatography is preferred, and the elution solvents used are methylene chloride-methanol, ethyl acetate-ethanol, chloroform-ethanol, acetone, ethyl acetate, pen l:'7-1 Tanol, benzene-ethanol, etc. are Hshi)C,)f+ru.
なお、カラムクロマトグラフィーにより?1)も−Jま
た苦味画分は更に分取薄層クロマトグラフィーCでイー
1し、その苦味画分を採取することができる。この場合
、分取りロマトグラフィーとしてけンリヵヶ゛ル分取り
ロマトグラフィーが採斤1し1!’t、iた展111)
溶媒としては前記溶出溶媒と同様のものがIII・出し
得る。Furthermore, by column chromatography? 1) Also, the bitter fraction can be further subjected to preparative thin layer chromatography C to collect the bitter fraction. In this case, the preparative chromatography is based on quenching chromatography. 't, ita exhibition 111)
As the solvent, the same solvent as the above-mentioned elution solvent can be used.
本発明の新規グリセリン配糖体は、耐病性が強く、抗菌
、抗ウィルス作用を有するため、4114物に対する抗
菌、抗ウィルス剤として使用しイ!+、’1/こ昆虫や
野ねずみに対して摂食阻害作用を有するため、これらに
対する摂取阻害剤として使1[4することができ、更に
カイワレダイコン等の植物の生長を抑制する作用を有す
るだめ、植物の生長抑制剤として使用することができる
など、農薬と17での用途を有する。また、保湿ン乍用
、朋荒わ予防作用を有し、更にイ111胞毒性を認めら
れないため、各J’li化粧料、医薬品制料としての用
途もイ1する。The novel glycerin glycoside of the present invention has strong disease resistance and has antibacterial and antiviral effects, so it can be used as an antibacterial and antiviral agent against 4114 substances! +、'1/Since it has an ingestion inhibitory effect on insects and field mice, it can be used as an ingestion inhibitor against them, and it also has the effect of suppressing the growth of plants such as Japanese radish. It has 17 uses as a pesticide, including being able to be used as a plant growth inhibitor. In addition, it has moisturizing and anti-inflammatory effects, and is not found to be toxic to 111 cells, so it can also be used as cosmetics and pharmaceutical products.
次に製端例を示す。Next, an example of edge production is shown.
〔巾、゛1造例〕
市販のホソバハカタユリの鱗茎8.6 kg(生重量)
を細かくきざみ、これを熱メタノール18!で抽出する
操作を3回縁り返した。抽I′1′1液をエバポレータ
ーで濃縮した後、クロロホルム−水(1:1)で約2回
分配し、唄にその水層を約倍肴のn−ブタノールで分配
して、クロロホルム層、n−ブタノール層、水JRの3
部分を得た。[Width, ゛1 example] Commercially available lily scales 8.6 kg (fresh weight)
Finely chop it and heat it with methanol 18! The extraction operation was repeated three times. After concentrating the extract I'1'1 solution with an evaporator, it was distributed about twice with chloroform-water (1:1), and the aqueous layer was partitioned with about twice as much n-butanol to form the chloroform layer, n-butanol layer, water JR 3
Got the part.
次に、n−ブタノール層をシリカゲルカラムクロマトグ
ラフィーに付し、クロロホルム−メタノール系で溶出し
た。この場合、クロロホルム:メタノール−20: 1
から順次極性を上げていき、その溶出フラクションを採
取した。そのうち、苦味のある7ラクシヨンを集め、更
にシリカダル分取りロマトグラフィー(分取薄層クロマ
トグラフィー)に付した。クロロホルム:メタノール=
3:1で2回展開し、R40,54付近を分取すること
により、式(2)の化合物16.0gを得、またクロロ
ホルム;メタノール−4−1で2回IΦ開し、Rf05
5付近を分取することにより、式(3)のイ)α物5.
5.9を得た。Next, the n-butanol layer was subjected to silica gel column chromatography and eluted with chloroform-methanol system. In this case, chloroform:methanol-20:1
The polarity was increased sequentially from then on, and the eluted fractions were collected. Among them, bitter-tasting 7-lactone was collected and further subjected to silica dal preparative chromatography (preparative thin layer chromatography). Chloroform: methanol =
By developing twice with 3:1 and fractionating around R40,54, 16.0 g of the compound of formula (2) was obtained.
By fractionating around 5, a) α product 5 of formula (3) is obtained.
5.9 was obtained.
式(2)の化合物の特性値
性状:淡黄色粉末
〔α几5ニー17°(C1,0チ、メタノール)Pへ4
R(CD501”)) :
δ3.56〜4.57 (g]ucose glyce
rol proton)6.33(I H,d 、 J
=16Hz、Ar−CTT=CH−’16.80 (2
H+d 、J=RHz 、aromatic prot
on)7.45 (2T(+d 、J=811v 、
aromatic proton)7.65 (IH,
d 、J=1 fd(y 、Ar−CH=CH−)式(
3)の化合物の特fI・値
性状:淡黄色粉末
〔α〕、−34°(C1,0%、メタノール)IRνK
11r dl : 3350(OH)、1710(C
=O)、1635(C=C)aX
P皿(CD30D):
δ3.56〜4.6(1(gluco!Ie glye
erol prntnn)6.34 (IH,d、J=
16Hz、Ar−CT1=Cl1−)6.81 (2
H+d、J=8T(z、aromatiCproton
)7.47 (2H,d、J=8Hz、aromat
ic proton)7.68 (H(、d、J=1
6Hz、Ar−CH=C)I−)2、+15 (3H
,S、−C−CT(3)II −一
〇
第 1 表
式(2)の化合物530mQに3 qbCH5ONa
4 mlを加え、宇部で3時間数[6゛後、アンバーラ
イトItえ一120カラムを通し、溶出物をシリカケ゛
ルクロマトグラフイーに付したところ、メチル−p−フ
マレート131.2ml?と下記式(4)で示される化
合物1666mqを得だ。Characteristics of the compound of formula (2) Properties: Pale yellow powder
R (CD501”): δ3.56-4.57 (g] ucose glyce
rol proton) 6.33 (I H, d, J
=16Hz, Ar-CTT=CH-'16.80 (2
H+d, J=RHz, aromatic prot
on) 7.45 (2T(+d, J=811v,
aromatic proton) 7.65 (IH,
d, J=1 fd(y, Ar-CH=CH-) formula (
Characteristic fI/value of compound 3) Properties: Pale yellow powder [α], -34° (C1,0%, methanol) IRνK
11r dl: 3350 (OH), 1710 (C
=O), 1635(C=C)aX P dish (CD30D): δ3.56-4.6(1(gluco!Ie glye
erol prntnn) 6.34 (IH, d, J=
16Hz, Ar-CT1=Cl1-)6.81 (2
H+d, J=8T(z, aromatiCproton
)7.47 (2H, d, J=8Hz, aromat
ic proton) 7.68 (H(, d, J=1
6Hz, Ar-CH=C)I-)2, +15 (3H
,S,-C-CT(3)II-10th 1 3 qbCH5ONa to 530 mQ of the compound of formula (2)
After 3 hours in Ube, the eluate was subjected to silica gel chromatography, and 131.2 ml of methyl p-fumarate was obtained. 1666 mq of a compound represented by the following formula (4) was obtained.
捷た、式(3)の化合物507 mQを月1い、回イ)
−に処理を行なってメチル−p−クマレー1−121.
3m9 ト下記式(5)で示される化合物166.8m
Qを得た。507 mQ of the diluted compound of formula (3) once a month)
- treated with methyl-p-coumaret 1-121.
3m9 Compound 166.8m represented by the following formula (5)
I got Q.
式(2)の化合物57.3 mgにピリジ:/ Q、
5 ml、無水酢酸0.5 mlを加え、−晩放置後、
常法に従って処理し、式(2)の化合物のへキサアセテ
ート71.01n9を得た。57.3 mg of the compound of formula (2) was added with pyridine:/Q,
Add 5 ml and 0.5 ml of acetic anhydride, and leave to stand overnight.
Treatment was performed according to a conventional method to obtain hexaacetate 71.01n9 of the compound of formula (2).
壕だ、式(3)の化合物108.91119から同様の
操作を行なって式(3)の化合物のペンタアセテート1
30m9を得た。The pentaacetate 1 of the compound of formula (3) is obtained by performing the same operation from compound 108.91119 of formula (3).
30m9 was obtained.
式(2)の化合物のヘキサアセテ−) ’% B 値性
状:無色釧状結晶
8点:142〜144℃(エタノールで再結晶)IRV
KBrcm−1二 1740(C=O)、 16
35(C−r)ax
PMR(cDct3):
δ200〜2.08(15H,0COC’ルー×5)2
.30 (3H、S 、 arom、0cOcH3)
3.6(1〜4.44(glucose glycer
ol proton)4.59 (IH+d+J=8
Hz+anomerlc proton)4.92〜5
.40(glucose glycerol prot
on)6.41 (IH,d、J=]6)(z、Ar
−CT■−CH−)7.51 (2)Ld+J=8T
Iz、aromatic proton)7.58
(2H,CJ=8Hz、aromatic proto
n)7.70 (IH,d、J=16T(z、Ar−
CH=CH−)元素分析値:C3oH360,6
CII O
計算値 55.21% 556チ 3923%実測値
55.00% 563% 3937チMS m、’Z
: 652(M−’)、610(M−OAc)式(
3)の化合物のペンタアセテート特性値性状:無色針状
結晶
融点: 】18〜120℃(エタノールで+’lTj結
、Jr!I)rRνKBr −1・
m□側 、 1740(C=O)、 1640(C=C
)PMR(CDC13) :
δ3.59〜4.45(glucoIIe glyce
rol proton)4.71 (IH,d+J=
’8Hz、anomericproton)4.92〜
5.40(glucose glycsrol pro
ton)6.40 (II(、d、J=16)1z、
Ar−CH=CH−)7.16 (2H,d、J=8
Hz、aromatleproton)7.59 (
2rI、d、J=RHz、aromatlcproto
n)7.72 (HI+d+J=]6ITz、Ar−
CI=(JT−)元素分析値:c3oH56o16
CHO
計算値55.21% 556チ 39.23%実測値5
514% 5.58% 3928%MS m/2 :
652(M”)、 610(M−OAc)式(2)及び
式(3)の化合物の酵素分解式(2)の化合物25 (
I mqを25mgのエムルシンを用イてPI−14,
0のアセテート緩衝液中で37℃において4時間反応を
行ない、反応液をn−ブタノールで分配し、n−ブタノ
ール層より式(6)で示される化合物98.4 m/?
を:4!) 、才だ水層よりグルコースを得た。Hexaacetate of the compound of formula (2) '% B value Properties: 8 colorless cylindrical crystals: 142-144°C (recrystallized with ethanol) IRV
KBrcm-12 1740 (C=O), 16
35(C-r)ax PMR (cDct3): δ200 ~ 2.08 (15H, 0COC'ru x 5) 2
.. 30 (3H, S, arom, 0cOcH3)
3.6(1~4.44(glucose glycer)
ol proton) 4.59 (IH+d+J=8
Hz+anomerlc proton) 4.92~5
.. 40 (glucose glycerol prot
on)6.41 (IH, d, J=]6) (z, Ar
-CT■-CH-)7.51 (2) Ld+J=8T
Iz, aromatic proton) 7.58
(2H, CJ=8Hz, aromatic proto
n) 7.70 (IH, d, J=16T(z, Ar-
CH=CH-) Elemental analysis value: C3oH360,6 CII O Calculated value 55.21% 556CH 3923% Actual value
55.00% 563% 3937chiMS m,'Z
: 652 (M-'), 610 (M-OAc) formula (
Pentaacetate properties of compound 3) Properties: Colorless needle-like crystals Melting point: ] 18-120°C (+'lTj with ethanol, Jr!I) rRνKBr -1・m□ side, 1740 (C=O), 1640 (C=C
) PMR (CDC13): δ3.59-4.45 (glucoIIe glyce
rol proton) 4.71 (IH, d+J=
'8Hz, anomeric proton) 4.92 ~
5.40 (glucose glycsrol pro
ton)6.40 (II(,d,J=16)1z,
Ar-CH=CH-)7.16 (2H, d, J=8
Hz, aromatleproton) 7.59 (
2rI, d, J=RHz, aromatlcproto
n) 7.72 (HI+d+J=]6ITz, Ar-
CI=(JT-) Elemental analysis value: c3oH56o16 CHO Calculated value 55.21% 556chi 39.23% Actual value 5
514% 5.58% 3928%MS m/2:
652 (M”), 610 (M-OAc) Enzymatic decomposition of compounds of formula (2) and formula (3) Compound 25 of formula (2)
PI-14 using 25 mg of emulcin,
The reaction was carried out at 37°C for 4 hours in an acetate buffer solution of 0.0, the reaction solution was partitioned with n-butanol, and from the n-butanol layer, 98.4 m/? of the compound represented by formula (6) was obtained.
:4! ), glucose was obtained from the aqueous layer.
また、式(3)ノ化合物250mqを25 mQl)
x ムルシンを用いて同様に反応を行ない、反応液を酢
酸エチルで分配し、酢酸エチル層より式(7)で示さt
]る化合物751nQをイn1水層よリグルコースを得
た。In addition, 250 mq of the compound of formula (3) was added to 25 mQl)
A reaction was carried out in the same manner using
] Compound 751nQ was extracted from the in1 aqueous layer to obtain religlucose.
υ 出願人 ライオン株式会社υ Applicant: Lion Corporation
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57163685A JPS5953497A (en) | 1982-09-20 | 1982-09-20 | Glycerin glycoside |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57163685A JPS5953497A (en) | 1982-09-20 | 1982-09-20 | Glycerin glycoside |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS5953497A true JPS5953497A (en) | 1984-03-28 |
Family
ID=15778646
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57163685A Pending JPS5953497A (en) | 1982-09-20 | 1982-09-20 | Glycerin glycoside |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5953497A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5358656A (en) * | 1991-12-31 | 1994-10-25 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising glyceroglycolipids having an amine linkage as a surfactant or cosurfactant |
EP0770378A1 (en) * | 1995-11-02 | 1997-05-02 | Beiersdorf Aktiengesellschaft | Cosmetic preparations with an effective amount of glycosylglycerides |
EP0824915A2 (en) * | 1996-08-23 | 1998-02-25 | Beiersdorf Aktiengesellschaft | Preparation of glycoglycerolipids, their use as surfactants and cosmetic or dermatological compositions containing them |
JP2001316208A (en) * | 2000-04-28 | 2001-11-13 | Kao Corp | Agent for vitalizing plant |
JP2007112759A (en) * | 2005-10-21 | 2007-05-10 | Biseibutsu Riyo Shinkino Busshitsu Seisan Gijutsu Kenkyu Kumiai | Insect pest feeding inhibitor and method |
WO2007124991A1 (en) * | 2006-04-27 | 2007-11-08 | Beiersdorf Ag | Cosmetic preparation with aquaporin stimulators and the use thereof |
JP2009541371A (en) * | 2006-07-03 | 2009-11-26 | ヒーベン・ビタル・ライセンス・アンパルトセルスカブ | Process for the production of mono- or diacylglycerol product glycosides from plant material |
CN103641867A (en) * | 2013-12-05 | 2014-03-19 | 湖南农业大学 | High-speed counter-current chromatography separation method and application of phenolic acid glycoside compounds in traditional Chinese medicine lily |
JP2015221768A (en) * | 2014-05-23 | 2015-12-10 | 日本メナード化粧品株式会社 | External or internal preparation for skin |
-
1982
- 1982-09-20 JP JP57163685A patent/JPS5953497A/en active Pending
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5358656A (en) * | 1991-12-31 | 1994-10-25 | Lever Brothers Company, Division Of Conopco, Inc. | Compositions comprising glyceroglycolipids having an amine linkage as a surfactant or cosurfactant |
EP0770378A1 (en) * | 1995-11-02 | 1997-05-02 | Beiersdorf Aktiengesellschaft | Cosmetic preparations with an effective amount of glycosylglycerides |
EP0824915A2 (en) * | 1996-08-23 | 1998-02-25 | Beiersdorf Aktiengesellschaft | Preparation of glycoglycerolipids, their use as surfactants and cosmetic or dermatological compositions containing them |
EP0824915A3 (en) * | 1996-08-23 | 1999-04-28 | Beiersdorf Aktiengesellschaft | Preparation of glycoglycerolipids, their use as surfactants and cosmetic or dermatological compositions containing them |
JP2001316208A (en) * | 2000-04-28 | 2001-11-13 | Kao Corp | Agent for vitalizing plant |
JP2007112759A (en) * | 2005-10-21 | 2007-05-10 | Biseibutsu Riyo Shinkino Busshitsu Seisan Gijutsu Kenkyu Kumiai | Insect pest feeding inhibitor and method |
WO2007124991A1 (en) * | 2006-04-27 | 2007-11-08 | Beiersdorf Ag | Cosmetic preparation with aquaporin stimulators and the use thereof |
JP2009541371A (en) * | 2006-07-03 | 2009-11-26 | ヒーベン・ビタル・ライセンス・アンパルトセルスカブ | Process for the production of mono- or diacylglycerol product glycosides from plant material |
CN103641867A (en) * | 2013-12-05 | 2014-03-19 | 湖南农业大学 | High-speed counter-current chromatography separation method and application of phenolic acid glycoside compounds in traditional Chinese medicine lily |
CN103641867B (en) * | 2013-12-05 | 2015-06-24 | 湖南农业大学 | High-speed counter-current chromatography separation method and application of phenolic acid glycoside compounds in traditional Chinese medicine lily |
JP2015221768A (en) * | 2014-05-23 | 2015-12-10 | 日本メナード化粧品株式会社 | External or internal preparation for skin |
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