JPS58134073A - Cyclopentenone derivative - Google Patents
Cyclopentenone derivativeInfo
- Publication number
- JPS58134073A JPS58134073A JP1628682A JP1628682A JPS58134073A JP S58134073 A JPS58134073 A JP S58134073A JP 1628682 A JP1628682 A JP 1628682A JP 1628682 A JP1628682 A JP 1628682A JP S58134073 A JPS58134073 A JP S58134073A
- Authority
- JP
- Japan
- Prior art keywords
- methylene chloride
- column chromatography
- compound
- formula
- cyclobentenone
- 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
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は一般式
(式中、Xは−CH2−C=C−又は−CH=C=CH
−であシ、三員項内の破線の箇所のいずれか一箇所は二
重結合を有する。)で表わされる新規シクロベンテノン
誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (wherein, X is -CH2-C=C- or -CH=C=CH
- Yes, one of the dashed lines in the three-membered term has a double bond. ) is related to a novel cyclobentenone derivative represented by
従来、多種の抗菌剤が開発され、使用されてきたが、抗
生物質に見られる如く、使用相反が多くなるにつれて耐
性−が出現することは良く知られた事実である。従って
これら薬剤の有効成分と全く異なる構造を崩して抗菌性
を゛示す化合物を開発することは、大きな意味があると
百える。A wide variety of antibacterial agents have been developed and used in the past, but it is a well-known fact that as antibiotics are used more frequently, resistance develops. Therefore, it would be of great significance to develop a compound that exhibits antibacterial properties by disrupting the structure that is completely different from the active ingredients of these drugs.
このような現況に鑑み、本発明者等は、多ねのコケ成分
中に抗菌性を示す化合物を検索した結果、前記一般式〇
)で表わされるシクロベンテノン誘導体がイネイモチ病
菌、大腸菌、ビール酵母、セレウス医、枯草菌及び緑1
Is1菌に対して抗菌性を廟することを見出し、本発明
を完成した。In view of this current situation, the present inventors searched for compounds exhibiting antibacterial properties in moss components of moss, and found that the cyclobentenone derivative represented by the above general formula , Dr. Cereus, Bacillus subtilis and green 1
They discovered that it has antibacterial properties against Is1 bacteria and completed the present invention.
前記一般式CI>で茨わさ扛るシクロベンテノン誘導体
はカモジゴケ(Dicranum scoparium
Hedw、 )あるいはシッポゴケ(Dicranum
japonicum Mi tt、 ) よシ抽出分離
したものであシ、これらは従来知られていない骨格を有
する新規化合物である。The cyclobentenone derivative represented by the general formula CI> is derived from Dicranum scoparium.
) or tail moss (Dicranum)
japonicum Mitt, ) and are extracted and separated, and are novel compounds with a skeleton that has not been previously known.
前記のコケは鮮度の高い状態のものを用い、抽出、単離
法は次のようにして行う。コケはブレングーあるいはホ
モジナイザーを用い細断して抽出を行うと効果が上がる
。抽出に当って溶媒は、含有取分の酸化、エステル化、
二重結合の異性化あるいはポリメリゼーション等を防ぐ
ようにする目的でアルミナカラム等を用いて過酸化物を
除いたり、単蒸留して用いるのが好ましい。抽出に用い
ることが出来る溶媒Lエーテル、塩化メチレン、あるい
は65〜80チメタノール等であり、これ−、ゝ
ら以外の有機溶媒、例えはクロロホルム、テトラ11
・
ヒドロフラン、アゼ、トン、メチルエチルケトン、ベン
ゼン等も上記のような注意を払って精製すれば使用する
ことが出来る。抽出は細断後1〜14日開室温で浸漬抽
出するかあるいはソックスレー抽出)を用いて抽出する
。抽出物はいずれの場合もg/に細によシ油状物として
得られる(収量約0.5〜2嘩)。粗抽出物から本発明
の化合物を精製するにはシリカゲルを用い九カラムクロ
マトグラフィーを組み合わせて行う。例えは吸着クロマ
トグラフィーをトルエン−酢酸エチル系で行い、次に吸
着クロマトグラフィーを塩化メチレン−メタノール系で
行い、′更に固定相に水を使い、移動相にヘキサン−酢
酸エチルを用いた分配クロマトグラフィーを行った後に
再ひ塩化メチレン−メタノール系による吸着クロマトグ
ラフィーを行う方法を採用出来る。これらの操作をする
ことにより本発明の化合物を純粋に単離出来る。各フラ
クションは30C以下で濃−瞥7′″)″お/″′は塩
化′チレン(いずれも精#!済み)溶液として一40p
で貯蔵すると変化を防止出来る。このように得られた各
フラクション溶液中の成分や精製の程度は随時薄層クロ
マトグラフィー(トルエン−酢酸エチル1:4;1:1
.あるいは塩化メチレン−メタノール14 : 1等)
で確認する。The above-mentioned moss is used in a highly fresh state, and extraction and isolation are performed as follows. It is more effective to extract moss by shredding it using a blender or a homogenizer. During extraction, the solvent is used to oxidize, esterify, and
In order to prevent double bond isomerization or polymerization, it is preferable to use an alumina column or the like to remove peroxides or to use simple distillation. Solvents that can be used for extraction include ether, methylene chloride, or 65-80 timeethanol, and organic solvents other than these, such as chloroform and tetra-11
- Hydrofuran, aze, methyl ethyl ketone, benzene, etc. can also be used if they are purified with the above precautions. Extraction is carried out using immersion extraction or Soxhlet extraction at an open room temperature for 1 to 14 days after shredding. The extract is obtained in each case as a finely ground oil in g/g (yield approximately 0.5-2 g). The compound of the present invention is purified from the crude extract by a combination of nine column chromatography using silica gel. For example, adsorption chromatography is performed in a toluene-ethyl acetate system, then adsorption chromatography is performed in a methylene chloride-methanol system, and then partition chromatography is performed using water as the stationary phase and hexane-ethyl acetate as the mobile phase. It is possible to adopt a method of carrying out adsorption chromatography using a methylene chloride-methanol system again after carrying out the above steps. By performing these operations, the compound of the present invention can be isolated in a pure manner. Each fraction was concentrated at a temperature below 30C.
Storage can prevent changes. The components and degree of purification in each fraction solution obtained in this manner were determined by thin layer chromatography (toluene-ethyl acetate 1:4; 1:1
.. or methylene chloride-methanol 14:1, etc.)
Check with.
本発明の前記一般式σ)で表わされるシクロベンテノン
鋳導体を農薬用抗菌剤として使用する場合には、原体を
そのままあるいは水に溶解して水溶液として使用しても
よいし、通常使用される形態すなわち粉剤、粒剤、粉粒
剤、水和剤、乳剤、液剤等いずれの製剤形態のものでも
使用出来る。When using the cyclobentenone cast conductor of the present invention represented by the above general formula σ) as an antibacterial agent for agricultural chemicals, the active substance may be used as it is or dissolved in water to form an aqueous solution, or it may be used as an aqueous solution using the conventionally used Any formulation form such as powder, granule, powder, wettable powder, emulsion, liquid, etc. can be used.
以下実施例によυ本発明を更に詳細に説明する。The present invention will be explained in more detail with reference to Examples below.
実施例1
カモジゴケ392gをエチルエーテル51中でブレング
ーによシ細断し、三角フラスコに移してそのまま2日間
厘温で抽出した。g過し、殖物体は丹ひエチルエーテル
21で4日間1dj様に抽出した。Example 1 392 g of Kamoji moss was shredded in ethyl ether 51 with a blender, transferred to an Erlenmeyer flask, and extracted as it was at room temperature for 2 days. The culture material was extracted with Tanhi ethyl ether 21 for 4 days in a 1dj manner.
抽出液はともに一動し、゛計6.5gの抽出物を侍た。Both extracts were stirred, and a total of 6.5 g of extract was served.
この試料をシリカゲルを用いた下記に示すカラムクロマ
トグラフィーにょシ精製し、8−、(2−、((イ)−
2−ペンテニル)−3−オキソ−4−シクロペンテン−
1−イル)−6−オクチン酸(以下シクロベンテノン誘
導体Aと称す。)を単離した。This sample was purified by column chromatography using silica gel as shown below, and 8-, (2-, ((i)-)
2-pentenyl)-3-oxo-4-cyclopentene-
1-yl)-6-octynoic acid (hereinafter referred to as cyclobentenone derivative A) was isolated.
なお、以下の実施例に於いて抗菌活性試験はすべてイネ
イモチ病菌に対して行った。In addition, in the following examples, all antibacterial activity tests were conducted against rice blast fungus.
カラムクロマトグラフィー1
ワコーゲルC−200(240g)をカラムにトルエン
で充填しく3.7X50−1抽出物6.7gをトルエン
溶液として注入した。酢酸エチル@Ijkトルエンに対
して5%ずつ増やして各々450 atずつ流し、酢酸
エチル40チ含有自分の第25〜27フラクシヨンに抗
菌性部370WIIを得た。Column Chromatography 1 A column of Wako Gel C-200 (240 g) was packed with toluene, and 6.7 g of the 3.7×50-1 extract was injected as a toluene solution. Ethyl acetate@Ijk was increased by 5% to toluene and 450 at each was flowed to obtain an antibacterial portion of 370 WII in the 25th to 27th fractions containing 40% ethyl acetate.
カラムクロマトグラフィー2
ワコーゲルC−200(50g”) 1il−カラムに
塩化メチレンで充填しく2.3X24crn)、カラム
クロマトグラフィー1で得た抗菌性部370”fを少量
の塩化メチレン溶液として注入した。メタノール含′I
kを塩化メチレンに対し、0.1%から10’%迄に遂
次増や&開し、O,S*メタツー−含有向分第16〜2
1フラクシ曹ンに抗菌性5s4qを得た。Column Chromatography 2 A Wako Gel C-200 (50 g") 1 il column was packed with methylene chloride (2.3 x 24 crn), and the antibacterial portion 370"f obtained in Column Chromatography 1 was injected as a small amount of methylene chloride solution. Methanol-containing 'I
The amount of k in methylene chloride was gradually increased from 0.1% to 10'%, and O, S
Antibacterial properties of 5s4q were obtained in 1 flax soda.
カラムクロマトグラフィー3
ワコーゲルC−C−200(40に水281114を含
ませてカラムを作製し、これにカラムクロマトグラフィ
ー2で得た抗菌性部84wqの5チ酢酸エチル含有へキ
サン溶液を注入し、酢酸エチル含量を5%ずつ増やして
展開し、5ts酢酸エチル含有の第3〜7フラクシヨン
に抗菌性部5811Pを得た。Column chromatography 3 A column was prepared by impregnating Wakogel C-C-200 (40) with 281,114 liters of water, and into this a hexane solution containing 84 wq of antibacterial ethyl acetate obtained in column chromatography 2 was injected. The ethyl acetate content was increased by 5% and developed to obtain antibacterial portion 5811P in the 3rd to 7th fractions containing 5ts ethyl acetate.
ワコーゲル(、’−200(10g)をカラムに塩化メ
チレンで充填し、カラムクロマトグラフィー3した。メ
タノール含iltを塩化メチレンに対して0.1チ〜0
.5チに増やして展開した。このうち0.1チの最初の
部分と0.5チの最初の部分のフラクション17〜31
から抗Ii1成分である無色油状物を酊34ダ、純粋に
得た。このものは以下に示す分析の結果8− (2−(
(イ)−2−ペンテニル)−3−オキソ−4−シクロペ
ンテン−1−イル)−6−オクチン酸でめることをm認
した。純度の確認eよシリカゲルTLC[塩化メチレン
:メタノール(14:1)2回展開;酢酸エチル:トル
エン(1:1);M色剤2 % Ce2 (804)3
in2N −H2SO,噴霧、加熱〕により黄色の8ポ
ツトを与えることにより行、りた。A column was filled with Wakogel (,'-200 (10 g) and methylene chloride, and column chromatography was performed.
.. The number was expanded to five. Of these, fractions 17 to 31 of the first part of 0.1 inch and the first part of 0.5 inch
34 days of pure colorless oil, which is the anti-Ii1 component, was obtained. This is the result of the analysis shown below 8- (2-(
(a) It was confirmed that the reaction mixture was dissolved with -2-pentenyl)-3-oxo-4-cyclopenten-1-yl)-6-octynic acid. Confirmation of purity e. Silica gel TLC [Developed twice with methylene chloride: methanol (14:1); ethyl acetate: toluene (1:1); M colorant 2% Ce2 (804)3
in 2N-H2SO, spraying, heating] to give 8 yellow spots.
□
NMR(400M)(z) 、′:δppm 7.70
(18,dd、 6゜−。□ NMR (400M) (z),': δppm 7.70
(18, dd, 6°-.
3Hz)、 6i30 (IH,dd、 6.2Hz)
。3Hz), 6i30 (IH, dd, 6.2Hz)
.
5.45 (IH,dddtl 11.212.6H2
)。5.45 (IH, dddtl 11.212.6H2
).
5.35(1ルaadto i 118+ 6+ 2H
2)13、HB (IH,ddddd、 8.6.5e
3.2Hz)。5.35 (1 le aadto i 118+ 6+ 2H
2) 13, HB (IH, dddd, 8.6.5e
3.2Hz).
2.57 (IH,dddd、 16.6.5.2H2
)。2.57 (IH, dddd, 16.6.5.2H2
).
2.53 (1)L da t−1615p 2Hz)
12.43(IH2ddd−11−6,5Hz)* 2
.37 (2H,t)? 2.28 (1)L ddd
d、 16.11゜8.2Hz) −2,24(1)
L dd tp 16,8゜2Hz)、 2.16
(2)L dd t、 2.2.7Hz)−2,08(
2)L ddq、6−2−7.5H2)#1.71(2
ル t t、 7.5t 7.5HzL 1.51
(2H,tt、 7t 7.5Hz)、 0.98
(3)Lt、 7.5Hz)e (他にGo2H)。2.53 (1) L da t-1615p 2Hz)
12.43 (IH2ddd-11-6,5Hz)*2
.. 37 (2H, t)? 2.28 (1) L ddd
d, 16.11°8.2Hz) -2,24(1)
L dd tp 16.8°2Hz), 2.16
(2) L dd t, 2.2.7Hz)-2,08(
2) L ddq, 6-2-7.5H2) #1.71 (2
Le t t, 7.5t 7.5HzL 1.51
(2H, tt, 7t 7.5Hz), 0.98
(3) Lt, 7.5Hz)e (also Go2H).
13C−NM旧δppm 210(s) 120(s)
、 &(s)、 165−40(d)、 133−48
(d)、 133.31(d)、126・77(d)、
83・45(s)、 77・2 o(s)。13C-NM old δppm 210(s) 120(s)
, &(s), 165-40(d), 133-48
(d), 133.31(d), 126.77(d),
83.45 (s), 77.2 o (s).
49.03(d)、 43・41(d)、 33.55
(t)、 28.10(t)、 23.89(t)、
23.66(t)、 20.85(t)。49.03(d), 43.41(d), 33.55
(t), 28.10(t), 23.89(t),
23.66(t), 20.85(t).
20.21(t)、 18.40(t)、 14−01
(2)。20.21(t), 18.40(t), 14-01
(2).
1)L(cm ”): 3600〜2500 (br
)* 3030−2950.1710,1590゜
MS(m/e):288.1671 (M )、 27
0(M+−H2O)、 259(M+−C2H5)、
220(M”−C5H1o)、 187(M −C5H
702)。1) L (cm ”): 3600~2500 (br
) * 3030-2950.1710, 1590°MS (m/e): 288.1671 (M), 27
0(M+-H2O), 259(M+-C2H5),
220(M”-C5H1o), 187(M-C5H
702).
〔α堅”:+191°、 (c=3.メタノール)λ叫
X(メタノール):217nm
(ε8550)。[α hard”: +191°, (c=3. methanol) λ cryX (methanol): 217 nm (ε8550).
実施例2
シツポゴケ569を70チメタノール(500sw/)
中でブレンダーにより細断し、三角フラスコに移し、そ
のまま室温で2日間抽出した。コケを#I適過後メタノ
ールを減圧留去し、ますへキサン、続いて酢酸エチルで
抽出した。酢酸エチル画分60岬を下記に示すシリカゲ
ルカラムクロマトグラフィーにより精製し、8−(2−
(の−2−ペンテニル)−3−オキソ−1−シクロペン
テン−1−イル)−6,7−オクタジエン酸(以下シク
ロベンテノン誘導体Bと称す。)を単離した。抗菌活性
試験はすべてイネイモチ病菌に対して行った。Example 2 70 timethanol (500 sw/) from Shitsupogo moss 569
The mixture was shredded in a blender, transferred to an Erlenmeyer flask, and extracted as it was at room temperature for 2 days. After removing the #I moss, methanol was distilled off under reduced pressure, and the mixture was extracted with hexane and then with ethyl acetate. Ethyl acetate fraction 60 Misaki was purified by silica gel column chromatography shown below to obtain 8-(2-
(-2-pentenyl)-3-oxo-1-cyclopenten-1-yl)-6,7-octadienoic acid (hereinafter referred to as cyclobentenone derivative B) was isolated. All antibacterial activity tests were conducted against the rice blast fungus.
カラムクロマトグラフィー 1
ワコーゲルC−20[)(12JF )をカラムにトル
エンで充填しく1.5X1!1111m+1)、抽出物
をトルエン溶液として注入した。酢酸エチルをトルエン
に対して10〜100チに遂次増やして展開したところ
、抗菌性−〜osWI酸エチルートルエン溶液で溶出し
、これを濃縮して油状物20wl1を得た。Column Chromatography 1 A Wako Gel C-20[) (12JF) column was packed with toluene (1.5×1!1111m+1), and the extract was injected as a toluene solution. When the amount of ethyl acetate was increased to 10 to 100 toluene and developed, an antibacterial osWI acid ethyl toluene solution was eluted, and this was concentrated to obtain 20 ml of oil.
岬を塩化メチレン溶液としてカラムに注入した。The cape was injected into the column as a methylene chloride solution.
2−メタノール−塩化メチレン溶液で展開し、7ラクシ
曹ン7〜8に抗菌活性部5fIIgを得たtカラムクロ
マトグラフィー 3
ワコーゲルC−200(3g )kカラムにエーテル−
ヘキサン1:1で充填し、カラムクロマトグラフィー2
で得たもの5ツを同溶媒に溶解して注入した。エーテル
を50〜100慢に遂次増やしつつ展開し、フラクショ
ン6〜14から抗菌成分1.4呼を純粋に得た。このも
のは以TK示もす分析結果から8−(2−(の−2−ペ
ンテニル)−3−オキソ−1−シクロペンテン−1−イ
ル)−6’、 7−オクタジエン酸であることを離間し
た。純度の確認はシリカゲルTLC(70%エーテル/
ヘキサン、呈色剤2 S Ce2(S04)3in 2
N−H2804噴霧、加熱)で行なったわ
NMR(400MHiN):Jppm6.37(IH,
dt、乙3Hz)、 5.5”j(IH,d’t、 7
.7Hz )、 5.40(IH,dtt、 11.7
.2Hz )、 5.27(I H。2-T column chromatography developed with methanol-methylene chloride solution to obtain the antibacterial active part 5fIIg in 7-lactic carbon 7-8. 3 Wakogel C-200 (3 g) K column with ether-
Packed with hexane 1:1, column chromatography 2
The five samples obtained in step 1 were dissolved in the same solvent and injected. The amount of ether was gradually increased by 50 to 100, and 1.4 antibacterial components were obtained in pure form from fractions 6 to 14. From the analysis results shown below, it was determined that this was 8-(2-(-2-pentenyl)-3-oxo-1-cyclopenten-1-yl)-6',7-octadienoic acid. . Purity was confirmed by silica gel TLC (70% ether/
Hexane, coloring agent 2 S Ce2 (S04) 3in 2
NMR (400MHiN): Jppm6.37 (IH,
dt, 3Hz), 5.5"j (IH, d't, 7
.. 7Hz), 5.40 (IH, dtt, 11.7
.. 2Hz), 5.27 (IH.
dtt、 11.7.2Hz)、 −、共土
3.02(2H,brd、 7Hz)。dtt, 11.7.2Hz), -, Kyodo
3.02 (2H, brd, 7Hz).
2.57(IH,dt、16.4Hz)、2.53(I
H。2.57 (IH, dt, 16.4Hz), 2.53 (I
H.
dt、16.4Hz)、2.40(2H,dd、4.4
Hz)。dt, 16.4Hz), 2.40 (2H, dd, 4.4
Hz).
2.59 (2H,t、 7Hz )、 2.17 (
2H,ddg。2.59 (2H, t, 7Hz), 2.17 (
2H, ddg.
2.7.7Hz )t 2.16(2H,ddt、3,
17Hり、 1.72(2H,tt、乙7Hz)、 1
.53(2H,it、乙7Hz)、 1.00(3H,
t、 7)。2.7.7Hz)t 2.16(2H, ddt, 3,
17H, 1.72 (2H, tt, Otsu 7Hz), 1
.. 53 (2H, it, Otsu 7Hz), 1.00 (3H,
t, 7).
MS(m/e ) : 288.1702(C,8H2
403M )。MS (m/e): 288.1702 (C, 8H2
403M).
+
259、1364(M −C2H5)、 187.11
25(M −C5H702)。+ 259, 1364 (M-C2H5), 187.11
25 (M-C5H702).
実施例3
抗イ・ネイモチ病菌活性試験
イネイモチ病菌の胞子を滅菌水Km濁し、辷れをポテト
−デキストロース−寒天培地と46′Oで混合し、その
際胞子濃度を10倍の対物レンズ1視野当ヤ約50個K
FA製した。このもの約10!lをシャーレに移して静
置、固化させた。その上にシクロベンテノン誘導偉人お
よびBの塩化メチレン溶液を浸ませた円形濾紙(径8m
mJl[さ0.7mm)をのせ、28℃で2日間培養し
、形成された阻止円径を測定した。結果は表1の通りで
ある。表中、ppmはシクロベンテノン誘導体A及びB
の8度を示す。なお、未処理のシャーレ上には菌糸が全
面生育していた。Example 3 Anti-potato fungus activity test The spores of the rice blast fungus were suspended in sterile water, and the spores were mixed with a potato-dextrose-agar medium at 46'O. Approximately 50 pieces
Made by FA. This thing is about 10! 1 was transferred to a petri dish and allowed to stand and solidify. A circular filter paper (diameter 8 m) was soaked with a methylene chloride solution of cyclobentenone derivative and B.
mJl [length: 0.7 mm] was placed on the plate, cultured at 28°C for 2 days, and the diameter of the inhibition circle formed was measured. The results are shown in Table 1. In the table, ppm is cyclobentenone derivative A and B.
8 degrees. Note that mycelium was growing all over the untreated petri dish.
表1
実施例4
抗大腸菌および抗ビール酵母活性試験
大腸菌を30−ci 4体振媛培養〔培地ニゲルコース
1.1M;ポリペプトンa7%;酵母抽出物0.5 %
: K2HPO40,5% ;蒸留水; pH7,2
; 50m!/−レKm地〔グルコース1.0%;ポリ
ペプトン0・7チ;酵母抽出物0.5チ:に2HPO4
0,5慢;寒天2−;蒸留水: pH7,5(以下寒天
培地と称す。)〕10mを入れ、静置、固化させt;。Table 1 Example 4 Anti-Escherichia coli and anti-brewer's yeast activity test 30-ci 4-body shaking culture of Escherichia coli [medium Nigelcose 1.1M; polypeptone a 7%; yeast extract 0.5%
: K2HPO40.5%; Distilled water; pH7.2
; 50m! /-LeKm ground [glucose 1.0%; polypeptone 0.7 t; yeast extract 0.5 t: 2HPO4
0.5; agar 2-; distilled water: pH 7.5 (hereinafter referred to as agar medium); 10 m was added and left to solidify.
得られた寒天培地平板上に先に用意した薗懸濁液0.5
dを注ぎ、ガラス棒を用いて均一に塗布した。濾紙円盤
(径8mm、厚さ0.7mm)にシクロベンテノン誘導
体AおよびBの塩化メチレン溶液を浸ませ、上記薗接種
済みの寒天培地上に曾き、30℃で一夜培養して形成さ
れた阻止円径を測定した。ビール酵母についても同様の
操作を行ない、形成された阻止円、径を測定した。結果
は表2の通りである。0.5 of the previously prepared soybean suspension was placed on the resulting agar plate.
d and applied it evenly using a glass rod. A filter paper disk (diameter 8 mm, thickness 0.7 mm) was immersed in a methylene chloride solution of cyclobentenone derivatives A and B, poured onto the agar medium inoculated with the above-mentioned soybean seed, and cultured overnight at 30°C. The diameter of the inhibition circle was measured. The same operation was performed for brewer's yeast, and the formed inhibition circle and diameter were measured. The results are shown in Table 2.
表2
−Ck−−−−−
実施例5
中
地)して得られた培養液0.5svt吟天培地(5WL
l)に40℃で混合し、これを暖めておいたシャーレ上
に手早く注入し、静胃、固化させた。Table 2 -Ck-----Example 5 Culture solution obtained by 0.5svt Ginten medium (5WL)
1) was mixed at 40°C, quickly injected onto a warmed Petri dish, and allowed to solidify.
シクロベンテノン誘導偉人およびBの塩化メチレン溶液
を円形濾紙(径8面−厚さ0.7mm)K浸ませ、上記
の菌畔種済みの寒天平板上に置い、1・□
た・30℃で一夜培竺し・形成された阻止円径を測定し
た。結果は表3の通りである。Circular filter paper (diameter 8 sides - thickness 0.7 mm) was immersed in a methylene chloride solution of cyclobentenone derivatives and B, placed on the above-mentioned agar plate and incubated at 30°C. The mixture was cultured overnight and the diameter of the inhibition circle formed was measured. The results are shown in Table 3.
表3
m−−3\ご一一一
実施例6
抗枯草菌及び抗ヒレウス菌活性試験
枯草菌及び七ノウス薗各々を30℃で1日液体振盪培1
1(液体培tjj’5シ、得られた菌を集菌し、生理食
塩水で洗浄した。各々の胞子形成用培地〔枯草11f=
ペプトン、59.肉エキス、31/ ;Pwln804
HnH20(n=4〜6 )t 10sv;寒天、15
p:H2O。Table 3 m--3\Go111 Example 6 Anti-Bacillus subtilis and anti-Hireus activity test Bacillus subtilis and Shichinousono each were cultured in liquid shaking culture 1 at 30°C for 1 day.
1 (liquid culture tjj'5), the obtained bacteria were collected and washed with physiological saline.
Peptone, 59. Meat extract, 31/; Pwln804
HnH20 (n=4-6)t 10sv; agar, 15
p: H2O.
1 / : pH7,0,セレウス薗:ペプトン、21
肉エキス、2g:食塩、11グルコース、29:寒天、
159 : H2O,L/:pH7,0)をシャーレ(
直径85mm )上に固化させ、得られた平板に上記の
菌を塗布し、枯草菌は30℃、セレウス菌は36℃で各
々4日間培養した。生成した胞子を滅菌水(25m)に
浮遊させて集め、この懸濁液と寒天培地とを50℃で混
合(胞子浮遊液2*l/培地1001I/)l、、この
うちの10m1をシャーレ上に注入し、静置、固化させ
た。シクロベンテノン誘導体A及びBの塩化メチレン溶
液を円形び紙(径8mm厚さ0.7mm)K浸ませ、上
記の菌接種済みの寒天平板上に置込て一夜培養し、形成
された阻1ト円径を測定した。結果は表4の通りである
。表中のpp哨シクロベンテノン誘導体人及びBの製産
である。1/: pH7.0, Cereus Sono: Peptone, 21
Meat extract, 2g: salt, 11 glucose, 29: agar,
159: H2O, L/: pH 7,0) in a petri dish (
The above-mentioned bacteria were applied to the obtained plate and cultured for 4 days at 30°C for Bacillus subtilis and 36°C for Bacillus cereus. Collect the generated spores by suspending them in sterile water (25 m), and mix this suspension with an agar medium at 50°C (2*l of spore suspension/1001 l of medium), and place 10 m1 of this on a petri dish. The solution was injected into the solution, left to stand, and allowed to solidify. A round paper (diameter 8 mm, thickness 0.7 mm) was immersed in a methylene chloride solution of cyclobentenone derivatives A and B, placed on an agar plate inoculated with the above bacteria, and cultured overnight. The diameter of the circle was measured. The results are shown in Table 4. This is the production of pp-cyclobentenone derivatives and B in the table.
表4Table 4
Claims (1)
を有する。)。(1) A cyclobentenone derivative represented by the general formula (in the formula, it has a double bond).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1628682A JPS58134073A (en) | 1982-02-05 | 1982-02-05 | Cyclopentenone derivative |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1628682A JPS58134073A (en) | 1982-02-05 | 1982-02-05 | Cyclopentenone derivative |
Publications (1)
Publication Number | Publication Date |
---|---|
JPS58134073A true JPS58134073A (en) | 1983-08-10 |
Family
ID=11912299
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1628682A Pending JPS58134073A (en) | 1982-02-05 | 1982-02-05 | Cyclopentenone derivative |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS58134073A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010149947A3 (en) * | 2009-06-23 | 2011-06-09 | Aston University | Antimicrobial agent |
-
1982
- 1982-02-05 JP JP1628682A patent/JPS58134073A/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010149947A3 (en) * | 2009-06-23 | 2011-06-09 | Aston University | Antimicrobial agent |
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