JPH054998A - Sterol compound - Google Patents
Sterol compoundInfo
- Publication number
- JPH054998A JPH054998A JP3266784A JP26678491A JPH054998A JP H054998 A JPH054998 A JP H054998A JP 3266784 A JP3266784 A JP 3266784A JP 26678491 A JP26678491 A JP 26678491A JP H054998 A JPH054998 A JP H054998A
- Authority
- JP
- Japan
- Prior art keywords
- ethyl acetate
- resulting
- compound
- collected
- extract
- 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
- -1 Sterol compound Chemical class 0.000 title claims abstract description 10
- 229930182558 Sterol Natural products 0.000 title claims abstract description 9
- 235000003702 sterols Nutrition 0.000 title claims abstract description 9
- 239000000126 substance Substances 0.000 claims description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 238000000034 method Methods 0.000 abstract description 7
- 241000243142 Porifera Species 0.000 abstract description 6
- 239000000284 extract Substances 0.000 abstract description 6
- 208000032839 leukemia Diseases 0.000 abstract description 5
- 241000778209 Xestospongia Species 0.000 abstract description 4
- 238000010898 silica gel chromatography Methods 0.000 abstract description 4
- 235000014653 Carica parviflora Nutrition 0.000 abstract description 3
- 241000243321 Cnidaria Species 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract description 3
- 239000000401 methanolic extract Substances 0.000 abstract description 3
- 239000000725 suspension Substances 0.000 abstract description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract description 2
- 235000011089 carbon dioxide Nutrition 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000706 filtrate Substances 0.000 abstract description 2
- 239000012520 frozen sample Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000118 anti-neoplastic effect Effects 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000000466 oxiranyl group Chemical group 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 210000004027 cell Anatomy 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 229940009456 adriamycin Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- 239000012156 elution solvent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 101100005765 Arabidopsis thaliana CDF1 gene Proteins 0.000 description 2
- 101100007579 Arabidopsis thaliana CPP1 gene Proteins 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 235000019786 weight gain Nutrition 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FBFNMTGUOBUGFQ-UHFFFAOYSA-M 2-(2,5-diphenyltetrazol-1-ium-1-yl)-4,5-dimethyl-1,3-thiazole;bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=C(C=2C=CC=CC=2)N=NN1C1=CC=CC=C1 FBFNMTGUOBUGFQ-UHFFFAOYSA-M 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は、抗腫瘍作用を有するス
テロール化合物に関する。TECHNICAL FIELD The present invention relates to a sterol compound having an antitumor effect.
【0002】[0002]
【従来の技術】本化合物と類似の構造で抗腫瘍作用を有
するものは報告が無い。2. Description of the Related Art There is no report of a compound having a structure similar to this compound and having an antitumor effect.
【0003】[0003]
【発明が解決しようとする課題】本発明の目的は、抗腫
瘍作用を有する新規な化合物を提供することにある。The object of the present invention is to provide a novel compound having an antitumor effect.
【0004】[0004]
【課題を解決するための手段】Xestospongi
a属海綿は、沖縄県西表島近海のサンゴ礁で採集され
る。本発明者は、このXestospongia属海綿
の抽出物に抗腫瘍作用を有する新規なステロール化合物
が含まれることを見出し、本発明を完成した。[Means for Solving the Problems] Xestospongi
The sponge of the genus a is collected on a coral reef near the sea near Iriomote Island, Okinawa Prefecture. The present inventor has found that the extract of sponge of the genus Xestospongia contains a novel sterol compound having an antitumor effect, and completed the present invention.
【0005】本発明の化合物は、下記化2で示されるス
テロール化合物である。The compound of the present invention is a sterol compound represented by the following chemical formula 2.
【0006】[0006]
【化2】 [Chemical 2]
【0007】本発明の化2で示されるステロール化合物
は、Xestospongia属海綿を原料とし、これ
を有機溶媒で抽出し、該抽出液から得られるエキスを通
常用いられる手法で分画および精製することにより単離
される。当該有機溶媒は、たとえばメタノール、エタノ
ール、エーテル、アセトン、ベンゼン、トルエン、酢酸
エチルなどが用いられるが、これに限らず他の適当な有
機溶媒を用いることができる。分画および精製は、たと
えばシリカゲルカラムクロマトグラフィー、分取シリカ
ゲル薄層クロマトグラフィー、高速液体クロマトグラフ
ィー、などのクロマトグラフィー法、再結晶法などによ
り行われる。ここで用いられる溶出溶媒は、たとえばエ
ーテル、石油エーテル、n−ヘキサン、酢酸エチル、ベ
ンゼン、トルエン、アセトン、メタノール、エタノー
ル、クロロホルム、ジクロロメタンなどの単独または混
合溶媒である。The sterol compound represented by the chemical formula 2 of the present invention is obtained by extracting Xestospongia sponge as a raw material, extracting this with an organic solvent, and fractionating and purifying the extract obtained from the extract by a commonly used method. Isolated. As the organic solvent, for example, methanol, ethanol, ether, acetone, benzene, toluene, ethyl acetate or the like is used, but not limited to this, other suitable organic solvent can be used. Fractionation and purification are performed by, for example, a chromatography method such as silica gel column chromatography, preparative silica gel thin layer chromatography, high performance liquid chromatography, and the like, a recrystallization method, and the like. The elution solvent used here is, for example, ether, petroleum ether, n-hexane, ethyl acetate, benzene, toluene, acetone, methanol, ethanol, chloroform, dichloromethane or the like alone or as a mixed solvent.
【0008】[0008]
【発明の効果】本発明により、Xestospongi
a属海綿から新規なステロール化合物が単離され、これ
が抗腫瘍作用を有し医薬品として有用であることが見出
された。According to the present invention, Xestospongi
A novel sterol compound was isolated from a sponge of the genus a and it was found that it has an antitumor effect and is useful as a pharmaceutical.
【0009】試験例1[抗腫瘍作用(In vitro
KB細胞増殖阻害)のスクリーニング]方法 平底の96穴プレートの各穴にKB細胞1×103個/
0.1mlの細胞浮遊液(10%牛胎児血清添加MEM
培地に浮遊)を添加し24時間培養した。これにジメチ
ルスルホキシドに溶解し、培地で希釈した本発明化合物
液100μl(ジメチルスルホキシド最終濃度0.5
%)を添加し、さらに72時間培養した。培養後、4,
5−ジメチルチアゾール−2−イル−2,5−ジフェニ
ルテトラゾリウム ブロマイド試薬(発色試薬)を添加
し、さらに4時間培養した。Test Example 1 [Antitumor effect (In vitro
Screening for inhibition of proliferation of KB cells] Method 1 × 10 3 KB cells / well in a 96-well plate with a flat bottom
0.1 ml of cell suspension (MEM containing 10% fetal bovine serum)
(Suspended in the medium) was added and cultured for 24 hours. 100 μl of a solution of the compound of the present invention dissolved in dimethyl sulfoxide and diluted with a medium (final concentration of dimethyl sulfoxide was 0.5
%) Was added and the cells were further cultured for 72 hours. After culturing 4,
5-Dimethylthiazol-2-yl-2,5-diphenyltetrazolium bromide reagent (coloring reagent) was added, and the mixture was further cultured for 4 hours.
【0010】コントロールとして培地100μl(ジメ
チルスルホキシド最終濃度0.5%)を添加し、同様に
培養した。培養終了後、培地を除き、細胞を150μl
のジメチルスルホキシドに溶解して吸光度を測定し、コ
ントロール群の吸光度に対する本発明化合物群の吸光度
の比を求め、50%阻害濃度(IC50)を計算した。
その結果、IC50は0.042μg/mlであった。As a control, 100 μl of a medium (final concentration of dimethyl sulfoxide 0.5%) was added, and the cells were cultured in the same manner. After culturing, remove the medium and add 150 μl of cells.
Was dissolved in dimethylsulfoxide and the absorbance was measured, the ratio of the absorbance of the compound of the present invention to the absorbance of the control group was determined, and the 50% inhibitory concentration (IC 50 ) was calculated.
As a result, IC 50 was 0.042 μg / ml.
【0011】試験例2[In vivo P388白血
病に対する延命効果] 方法 P388白血病細胞5×105個をDBA/2系雌性マ
ウスに腹腔内移植し、7日目の腹水より腫瘍細胞を採取
した。生細胞5×106個/mlの細胞浮遊液(ハンク
ス平衡塩類溶液に浮遊)を調製し、その0.2ml(1
×106個/匹)をCDF1系雌性マウス(7週令)に
腹腔内移植した。細胞移植日をday0として、細胞移
植翌日より5日間、0.5%アラビアゴム−生理食塩水
に懸濁した本発明化合物を腹腔内投与した。Test Example 2 [Life extension effect on in vivo P388 leukemia] Method 5 × 10 5 P388 leukemia cells were intraperitoneally transplanted into DBA / 2 female mice, and tumor cells were collected from ascites on the 7th day. A cell suspension containing 5 × 10 6 viable cells / ml (suspended in Hank's balanced salt solution) was prepared, and 0.2 ml (1
CDF1 female mice (7 weeks old) were intraperitoneally transplanted (× 10 6 cells / mouse). The day of cell transplantation was set to day 0, and the compound of the present invention suspended in 0.5% gum arabic-physiological saline was intraperitoneally administered for 5 days from the day following cell transplantation.
【0012】対照薬としてアドリアマイシン(ADM)
を生理食塩水に溶解して用いた。効果は、マウスの生存
日数中央値(MST)を求め、Adriamycin (ADM) as a control drug
Was dissolved in physiological saline and used. The effect was obtained by calculating the median survival time (MST) of mice,
【0013】[0013]
【数1】 により判定した。結果を表1に示した。[Equation 1] It was judged by. The results are shown in Table 1.
【0014】[0014]
【表1】 [Table 1]
【0015】(注) 1.体重増加はday 4からday 1の体重を差で
示した。 2.コントロールのMSTは9.3日であった。(Note) 1. The weight gain was represented by the difference in body weight from day 4 to day 1. 2. The control MST was 9.3 days.
【0016】試験例3[In vivo L1210白
血病に対する延命効果] 方法 L1210白血病細胞1×105個をDBA/2系雌性
マウスに腹腔内移植し、7日目の腹水より腫瘍細胞を採
取した。生細胞5×105個/mlの細胞浮遊液(ハン
クス平衡塩類溶液に浮遊)を調製し、その0.2ml
(1×105個/匹)をCDF1系/雌性マウス(7週
令)に腹腔内移植した。細胞移植日をday 0とし
て、細胞移植翌日より5日間、0.5%アラビアゴム−
生理食塩水に懸濁した本発明化合物を腹腔内投与した。Test Example 3 [Life extension effect on in vivo L1210 leukemia] Method 1 × 10 5 L1210 leukemia cells were intraperitoneally transplanted into DBA / 2 female mice, and tumor cells were collected from ascites on the 7th day. Prepare a cell suspension containing 5 x 10 5 viable cells / ml (suspended in Hank's balanced salt solution) and prepare 0.2 ml of the suspension.
(1 × 10 5 cells / mouse) were intraperitoneally transplanted into CDF1 strain / female mice (7 weeks old). The day of cell transplantation was set to day 0, and 5 days from the day after cell transplantation, 0.5% gum arabic-
The compound of the present invention suspended in physiological saline was intraperitoneally administered.
【0017】対照薬としてアドリアマイシン(ADM)
を生理食塩水に溶解して用いた。効果は試験例2と同様
に判定した。結果を表2に示した。Adriamycin (ADM) as a control
Was dissolved in physiological saline and used. The effect was determined in the same manner as in Test Example 2. The results are shown in Table 2.
【0018】[0018]
【表2】 [Table 2]
【0019】(注) 1.体重増加はday 4からday 1の体重を差で
示した。 2.コントロールのMSTは9.1日であった。(Note) 1. The weight gain was represented by the difference in body weight from day 4 to day 1. 2. The control MST was 9.1 days.
【0020】[0020]
【実施例】次に、実施例を挙げて本発明をより具体的に
説明する。EXAMPLES Next, the present invention will be described more specifically by way of examples.
【0021】実施例 沖縄県西表島近海のサンゴ礁で採集したXestosp
ongia属海綿を直ちにドライアイスで凍結した。こ
の凍結試料(3.1kg)をメタノール(6L)で一晩
冷浸した。メタノール抽出液を▲ろ▼過し、▲ろ▼液を
減圧下濃縮して残査87.4gを得た。同様のメタノー
ル抽出をさらに2回行い、50gの抽出物を得た。メタ
ノール抽出物を合わせ(137.4g)、これを水1.
5Lに懸濁し、酢酸エチル1.5Lで3回抽出した。酢
酸エチル可溶部を合わせ、減圧下濃縮して酢酸エチル可
溶26.0gを得た。酢酸エチル可溶部21gをシリカ
ゲルカラムクロマトグラフィー(フジデビソンBW−8
20MH,500g)に付し、5画分を得た(画分1;
ヘキサン1000mlで溶出,画分2;ヘキサン:酢酸
エチル=2:1,1000mlで溶出,画分3;ヘキサ
ン:酢酸エチル=1:2,1000mlで溶出,画分
4;酢酸エチル1000mlで溶出,画分5;メタノー
ル1500mlで溶出)。ここで得た画分4(6.56
g)をさらにシリカゲルカラムクロマトグラフィー(フ
ジデビソンBW−820MH,150g,溶出溶媒;ヘ
キサン:酢酸エチル=1:1,1画分;40ml)に付
し、25画分を得た。画分13〜20(2.91g)を
フラッシュクロマトグラフィー(シリカゲル;フジデビ
ソンBW−300,200g,溶出溶媒;ヘキサン:酢
酸エチル=2:1,1画分;40ml)に付し、66画
分を得た。画分41〜47(460mg)は結晶化した
ので、これをヘキサン−酢酸エチルから再結晶し、無色
針状結晶の本発明化合物233mgを得た。Example Xestosp collected from a coral reef near Iriomote Island, Okinawa Prefecture
The sponges of the genus ongia were immediately frozen on dry ice. This frozen sample (3.1 kg) was cold-soaked with methanol (6 L) overnight. The methanol extract was filtered and the filtrate was concentrated under reduced pressure to obtain a residue of 87.4 g. The same methanol extraction was performed twice more to obtain 50 g of extract. The methanol extracts were combined (137.4 g) and this was added to water 1.
It was suspended in 5 L and extracted 3 times with 1.5 L of ethyl acetate. The ethyl acetate-soluble parts were combined, and concentrated under reduced pressure to obtain ethyl acetate-soluble 26.0 g. 21 g of ethyl acetate-soluble portion was subjected to silica gel column chromatography (Fujidevison BW-8
20 MH, 500 g) to give 5 fractions (fraction 1;
Elution with 1000 ml of hexane, fraction 2; elution with hexane: ethyl acetate = 2: 1, 1000 ml, fraction 3; elution with hexane: ethyl acetate = 1: 2, 1000 ml, fraction 4; elution with 1000 ml of ethyl acetate Min 5; eluted with 1500 ml of methanol). Fraction 4 obtained here (6.56)
g) was further subjected to silica gel column chromatography (Fujidevison BW-820MH, 150 g, elution solvent; hexane: ethyl acetate = 1: 1, 1 fraction; 40 ml) to obtain 25 fractions. Fractions 13 to 20 (2.91 g) were subjected to flash chromatography (silica gel; Fujidevison BW-300, 200 g, elution solvent; hexane: ethyl acetate = 2: 1, 1 fraction; 40 ml), and 66 fractions were collected. Obtained. Fractions 41 to 47 (460 mg) crystallized, and were recrystallized from hexane-ethyl acetate to obtain 233 mg of the present compound as colorless needle crystals.
【0022】融点;157〜158℃ 元素分析値; 計算値(%)C:75.94,H:10.11 実測値(%)C:75.64,H:10.20 IR(KBr) cm−1; 3490,3394,1708,1030Melting point: 157 to 158 ° C. Elemental analysis value; Calculated value (%) C: 75.94, H: 10.11 Measured value (%) C: 75.64, H: 10.20 IR (KBr) cm -1 ; 3490, 3394, 1708, 1030
【0023】1H−NMR(500MHz,CDC
l3)δ(ppm) 0.16(1H,q,J=4.5Hz),0.26(2
H,m),0.50(1H,heptet,J=5.9
Hz),0.73(3H,s),0.83(1H,
m),0.91(1H,m),0.95(3H),0.
96(1H,m),1.01(3H,s),1.02
(3H,d,J=6.1Hz),1.07(1H,d
d,J=7.8Hz,11.0Hz),1.45(1
H,m),1.50(1H,m),1.62(1H,
m),1.71(1H,qd,J=3.1Hz,13.
1Hz),1.75(1H,m),1.79(1H,t
d,J=4.2Hz,13.0Hz),1.95(1
H,m),2.03(1H,ddd,J=2.2Hz,
6.4Hz,14.0HZ),2.09(1H,dd
d,J=2.1Hz,3.8Hz,15.0Hz),
2.16(1H,dd,J=9.0Hz,10.8H
z),2.25(1H,t,J=14.3Hz),2.
31(1H,brd,J=13.5Hz),2.37
(1H,dt,J=6.5Hz,13.5Hz),2.
92(1H,d,J=3.9Hz),3.08(1H,
d,J=3.9Hz),3.39(1H,dd,J=
4.6Hz,11.0Hz),3.46(1H,dd,
J=2.4Hz,10.6Hz) 1 H-NMR (500 MHz, CDC
l 3 ) δ (ppm) 0.16 (1H, q, J = 4.5 Hz), 0.26 (2
H, m), 0.50 (1H, heptet, J = 5.9)
Hz), 0.73 (3H, s), 0.83 (1H,
m), 0.91 (1H, m), 0.95 (3H), 0.
96 (1H, m), 1.01 (3H, s), 1.02
(3H, d, J = 6.1 Hz), 1.07 (1H, d
d, J = 7.8 Hz, 11.0 Hz), 1.45 (1
H, m), 1.50 (1H, m), 1.62 (1H,
m), 1.71 (1H, qd, J = 3.1 Hz, 13.
1 Hz), 1.75 (1H, m), 1.79 (1H, t
d, J = 4.2 Hz, 13.0 Hz), 1.95 (1
H, m), 2.03 (1H, ddd, J = 2.2 Hz,
6.4 Hz, 14.0 HZ), 2.09 (1 H, dd
d, J = 2.1 Hz, 3.8 Hz, 15.0 Hz),
2.16 (1H, dd, J = 9.0Hz, 10.8H
z), 2.25 (1H, t, J = 14.3Hz), 2.
31 (1H, brd, J = 13.5Hz), 2.37
(1H, dt, J = 6.5Hz, 13.5Hz), 2.
92 (1H, d, J = 3.9Hz), 3.08 (1H,
d, J = 3.9 Hz), 3.39 (1H, dd, J =
4.6 Hz, 11.0 Hz), 3.46 (1 H, dd,
J = 2.4Hz, 10.6Hz)
【0024】13C−NMR(125MHZ,CDCl
3)δ(ppm) 8.2(CH3),11.4(CH3),12.4(C
H2),12.5(CH),18.9(CH3),1
9.1(CH3),23.7(CH2),26.8(C
H2),27.6(CH),28.8(CH2),2
9.4(CH2),31.0(CH2),33.7(C
H),34.9(CH),35.6(−C−),38.
1(CH2),38.4(CH2),40.1(C
H2),44.5(CH2),46.5(CH),4
8.1(CH),48.8(−C−),50.6(CH
2),52.2(CH),54.3(CH),65.8
(−C−),72.2(CH),77.4(CH),2
11.8(CO) 13 C-NMR (125 MHZ, CDCl
3 ) δ (ppm) 8.2 (CH 3 ), 11.4 (CH 3 ), 12.4 (C
H 2 ), 12.5 (CH), 18.9 (CH 3 ), 1
9.1 (CH 3), 23.7 ( CH 2), 26.8 (C
H 2 ), 27.6 (CH), 28.8 (CH 2 ), 2
9.4 (CH 2 ), 31.0 (CH 2 ), 33.7 (C
H), 34.9 (CH), 35.6 (-C-), 38.
1 (CH 2 ), 38.4 (CH 2 ), 40.1 (C
H 2 ), 44.5 (CH 2 ), 46.5 (CH), 4
8.1 (CH), 48.8 (-C-), 50.6 (CH
2 ), 52.2 (CH), 54.3 (CH), 65.8.
(-C-), 72.2 (CH), 77.4 (CH), 2
11.8 (CO)
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3266784A JPH054998A (en) | 1990-07-17 | 1991-07-15 | Sterol compound |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18861490 | 1990-07-17 | ||
JP2-188614 | 1990-07-17 | ||
JP3266784A JPH054998A (en) | 1990-07-17 | 1991-07-15 | Sterol compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH054998A true JPH054998A (en) | 1993-01-14 |
Family
ID=26505037
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP3266784A Pending JPH054998A (en) | 1990-07-17 | 1991-07-15 | Sterol compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH054998A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995001367A1 (en) * | 1993-06-30 | 1995-01-12 | Taisho Pharmaceutical Co., Ltd. | Sterol compound |
WO1998040399A1 (en) * | 1997-03-12 | 1998-09-17 | Taisho Pharmaceutical Co., Ltd. | Sterol compounds |
-
1991
- 1991-07-15 JP JP3266784A patent/JPH054998A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995001367A1 (en) * | 1993-06-30 | 1995-01-12 | Taisho Pharmaceutical Co., Ltd. | Sterol compound |
WO1998040399A1 (en) * | 1997-03-12 | 1998-09-17 | Taisho Pharmaceutical Co., Ltd. | Sterol compounds |
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