JPH07267940A - New 11-membered ring compound - Google Patents
New 11-membered ring compoundInfo
- Publication number
- JPH07267940A JPH07267940A JP6059390A JP5939094A JPH07267940A JP H07267940 A JPH07267940 A JP H07267940A JP 6059390 A JP6059390 A JP 6059390A JP 5939094 A JP5939094 A JP 5939094A JP H07267940 A JPH07267940 A JP H07267940A
- Authority
- JP
- Japan
- Prior art keywords
- membered ring
- ring compound
- new
- structural formula
- compound
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Epoxy Compounds (AREA)
Abstract
Description
【0001】[0001]
【産業上の利用分野】本発明は新規物質、より詳しくは
新規な11員環化合物に関する。FIELD OF THE INVENTION The present invention relates to a novel substance, and more particularly to a novel 11-membered ring compound.
【0002】[0002]
【従来の技術】各種の産業分野、就中、医薬の分野では
各種の疾患に対する有効な新薬の開発が期待されてい
る。2. Description of the Related Art In various industrial fields, in particular, in the field of medicine, the development of new drugs effective against various diseases is expected.
【0003】[0003]
【発明が解決しようとする課題】前項記載の従来の技術
の背景下に、本発明の制癌剤としての用途の期待される
新規化合物の提供を目的とする。Under the background of the prior art described in the preceding paragraph, it is an object of the present invention to provide a novel compound expected to be used as a carcinostatic agent of the present invention.
【0004】[0004]
【課題を解決するための手段】本発明者は、キク科(C
ompostae)の植物Mikania hirsu
tissimaの乾燥した葉および茎からの抽出成分中
に細胞毒性、延いては強い生育阻害活性を有するものの
あることを見出し、この成分を同定して本発明を完成し
た。Means for Solving the Problems The present inventor
ompostae) plant Mikania hirsu
It was found that some of the components extracted from dried leaves and stems of tissima have cytotoxicity, and thus, strong growth inhibitory activity, and this component was identified to complete the present invention.
【0005】即ち、本発明は、下記構造式(I)を有す
る新規な11員環化合物に関する。That is, the present invention relates to a novel 11-membered ring compound having the following structural formula (I).
【0006】[0006]
【化2】 [Chemical 2]
【0007】以下、本発明の化合物の生育阻害活性およ
び分離、同定について説明する。The growth inhibitory activity, isolation and identification of the compound of the present invention will be described below.
【0008】Mikania hirsutissim
aの乾燥葉と茎861.9gをミキサーにて粉末状に
し、超音波をかけながらエタノール2Lで3回抽出して
得られた抽出液を合し、減圧下にて濃縮し、39.8g
のエタノール抽出物を得た。この抽出物についてマウス
の白血病細胞(L−1210)に対する生育阻害活性試
験を行ったところ、かなり強い生育阻害がみられた。Mikania hirsutissim
861.9 g of dried leaves and stems of a were powdered with a mixer, extracted with 2 L of ethanol three times while applying ultrasonic waves, and the extracts obtained were combined and concentrated under reduced pressure to give 39.8 g.
The ethanol extract of When this extract was tested for growth inhibitory activity against mouse leukemia cells (L-1210), considerably strong growth inhibition was observed.
【0009】すなわち、得られた粗抽出物は、「Dia
ion HP−20」カラムクロマトグラフィーに付
し、40%含水メタノール(2L)、70%含水メタノ
ール(2L)、メタノール(3L)およびアセトン(2
L)で順次流出させた。次いで、各4画分を濃縮し、細
胞試験を行ったところ、メタノール画分(C画分と称す
る)に最も強い阻害活性が認められた。That is, the obtained crude extract is "Dia
ion HP-20 "column chromatography, 40% hydrous methanol (2 L), 70% hydrous methanol (2 L), methanol (3 L) and acetone (2 L).
L) was made to flow out sequentially. Then, each 4 fractions were concentrated and subjected to a cell test. As a result, the strongest inhibitory activity was observed in the methanol fraction (referred to as C fraction).
【0010】そこで、このメタノール画分をシリカゲル
カラムクロマトグラフィーにより分離・精製を行った
(「Wacogel C−200」順相)。移動相とし
ては、ヘキサン−酢酸エチル混合溶媒を用い、ヘキサ
ン:酢酸エチル=15:1(1L)から、順次ヘキサ
ン:酢酸エチル=13:1(1L)、10:1(1
L)、7:1(1L)、5:1(2L)、3:1(2
L)、2:1(3L)、1:1(2L)にて流出させ、
さらに酢酸エチル(1L)、メタノール(1L)にて流
出させて約50のフラクションに分けた後、各クラクシ
ョンを薄層クロマトグラフィーにより分析し、同一成分
と思われるフラクションはまとめ、全部で13画分とし
た。各画分を順次MH(C−1)、MH(C−2)、…
……およびMH(C−13)と称することにする。Therefore, this methanol fraction was separated and purified by silica gel column chromatography ("Wacogel C-200" normal phase). As the mobile phase, a hexane-ethyl acetate mixed solvent was used, and hexane: ethyl acetate = 15: 1 (1 L) to hexane: ethyl acetate = 13: 1 (1 L), 10: 1 (1
L), 7: 1 (1 L), 5: 1 (2 L), 3: 1 (2
L), 2: 1 (3L), 1: 1 (2L),
Further, after elution with ethyl acetate (1 L) and methanol (1 L) to divide into about 50 fractions, each fraction was analyzed by thin layer chromatography. Fractions considered to have the same component were collected and a total of 13 fractions were collected. And Each fraction is sequentially MH (C-1), MH (C-2), ...
... and MH (C-13).
【0011】各分画について、後に説明する方法で細胞
毒性試験を行なった。その結果を下記第1表に示す。Each fraction was tested for cytotoxicity by the method described later. The results are shown in Table 1 below.
【0012】[0012]
【表1】 [Table 1]
【0013】次に、強い生育阻害活性が見られたMH
(C−7)画分を高速液体クロマトグラフィー(HPL
C:シリカゲル20φ×250mm、流速8.0ml/
min、ヘキサン:酢酸エチル=5:1)にてさらに分
離・精製し、屈折率計(RI検出器)を用いて8つのピ
ークに対応する8画分を得た。各画分を順次C7−1、
C7−2、………およびC7−8と称することにする。Next, MH showing a strong growth inhibitory activity.
The (C-7) fraction was subjected to high performance liquid chromatography (HPL).
C: Silica gel 20φ × 250 mm, flow rate 8.0 ml /
min, hexane: ethyl acetate = 5: 1) for further separation and purification, and using a refractometer (RI detector), 8 fractions corresponding to 8 peaks were obtained. Each fraction is sequentially C7-1,
... and C7-8.
【0014】次いで、C7−8画分をさらにHPLC
(シリカゲル10φ×250mm、流速3.0ml/m
in、ヘキサン:酢酸エチル=3:1)にて分離・精製
し、同じ屈折率計を用いて5つのピークに対応する5画
分を得、最後の画分を同じ条件でHPLCに付して精製
し保持時間17minの精製物を得た。これをMH−6
と称することにする。Then, the C7-8 fraction was further subjected to HPLC.
(Silica gel 10φ × 250 mm, flow rate 3.0 ml / m
in, hexane: ethyl acetate = 3: 1), and separated and purified to obtain 5 fractions corresponding to 5 peaks using the same refractometer, and the last fraction was subjected to HPLC under the same conditions. Purification yielded a purified product with a retention time of 17 min. This is MH-6
I will call it.
【0015】なお、細胞毒性試験の詳細は、次の通りで
ある。The details of the cytotoxicity test are as follows.
【0016】12%の牛胎児血清およびL−グルタミン
0.3g/Lを含有する日水製薬(株)製「RPMI
1640」培地(ただし、カナマイシン100mg/L
および10%NaHCO3 を含有)に、マウス白血病細
胞(L−1210)を培養し、細胞数が約10×105
cells/mlになった時点で、上記培地で10倍に
希釈(10×104 cells/ml)し、2mlずつ
シャーレに分注した。"RPMI" containing 12% fetal bovine serum and L-glutamine 0.3 g / L manufactured by Nissui Pharmaceutical Co., Ltd.
1640 ”medium (however, kanamycin 100 mg / L
And containing 10% NaHCO 3 ), mouse leukemia cells (L-1210) were cultured to obtain a cell number of about 10 × 10 5.
At the time of reaching cells / ml, the cells were diluted 10-fold with the above medium (10 × 10 4 cells / ml) and dispensed in 2 ml aliquots.
【0017】次いで、下記第2表に示す各濃度のMH−
6のメタノール溶液10μl、対照として同量のメタノ
ールを加え、CO2 インキュベーター(CO2 5%、3
7°C)にて培養し、約3日後にトリパンブルーにて染
色後、生細胞数を計測した。Next, MH- of each concentration shown in Table 2 below.
10 μl of methanol solution of 6 and the same amount of methanol as a control were added, and CO 2 incubator (CO 2 5%, 3
After culturing at 7 ° C) and staining with trypan blue after about 3 days, the number of viable cells was counted.
【0018】[0018]
【表2】 [Table 2]
【0019】なお、阻害率の算出は、次の通りである。The inhibition rate is calculated as follows.
【0020】[0020]
【数1】 [Equation 1]
【0021】MH−6の同定データは、次の通りであ
る。The identification data of MH-6 are as follows.
【0022】mpは136〜139℃、[α]D 14=−
5.0°(MeOH、C=0.8)、HR−MS(高分
解能マススペクトル):222.1661(M+ )で、
分子式はC14H12O2 と同定され、また下記第3表に示
すNMRの化学シフトのデータから前記構造式を有する
ことがわかる。Mp is 136 to 139 ° C., [α] D 14 =-
5.0 ° (MeOH, C = 0.8), HR-MS (high resolution mass spectrum): 222.1661 (M + ),
The molecular formula was identified as C 14 H 12 O 2, and it can be seen from the NMR chemical shift data shown in Table 3 below that the compound has the above structural formula.
【0023】[0023]
【表3】 [Table 3]
【0024】[0024]
【発明の効果】本発明により、制癌剤として大いに期待
することのできる新規物質が提供されるところとなっ
た。INDUSTRIAL APPLICABILITY According to the present invention, a novel substance which can be greatly expected as an anticancer agent has been provided.
Claims (1)
環化合物。 【化1】 1. A novel 11-membered ring compound having the following structural formula (I): [Chemical 1]
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6059390A JPH07267940A (en) | 1994-03-29 | 1994-03-29 | New 11-membered ring compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6059390A JPH07267940A (en) | 1994-03-29 | 1994-03-29 | New 11-membered ring compound |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH07267940A true JPH07267940A (en) | 1995-10-17 |
Family
ID=13111916
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP6059390A Pending JPH07267940A (en) | 1994-03-29 | 1994-03-29 | New 11-membered ring compound |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH07267940A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002096348A3 (en) * | 2001-05-30 | 2004-05-06 | Sod Conseils Rech Applic | Product comprising mikanolide, dihydromikanolide or an analogue thereof combined with another anti-cancer agent for therapeutic use in cancer treatment |
US7091239B2 (en) * | 1999-12-01 | 2006-08-15 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | DNA polymerase inhibitors, mikanolide and dihydromikanolide |
-
1994
- 1994-03-29 JP JP6059390A patent/JPH07267940A/en active Pending
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7091239B2 (en) * | 1999-12-01 | 2006-08-15 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | DNA polymerase inhibitors, mikanolide and dihydromikanolide |
WO2002096348A3 (en) * | 2001-05-30 | 2004-05-06 | Sod Conseils Rech Applic | Product comprising mikanolide, dihydromikanolide or an analogue thereof combined with another anti-cancer agent for therapeutic use in cancer treatment |
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