JPS5896079A - Homoserine lactone derivative - Google Patents
Homoserine lactone derivativeInfo
- Publication number
- JPS5896079A JPS5896079A JP19214981A JP19214981A JPS5896079A JP S5896079 A JPS5896079 A JP S5896079A JP 19214981 A JP19214981 A JP 19214981A JP 19214981 A JP19214981 A JP 19214981A JP S5896079 A JPS5896079 A JP S5896079A
- Authority
- JP
- Japan
- Prior art keywords
- methanol
- homoserine lactone
- acetone
- formula
- homoserine
- 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.)
- Granted
Links
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規なホモセリンラクトン誘導体に関し、さら
に詳細には構造式
で表わされる新規なホモ上１１ンラクトン誘導体に関す
るものであるー、
本発明の化合物は文献未載の新規化合物であり、酸アミ
ド糸除草剤および医薬品として使用される可能性がある
。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel homoserine lactone derivative, and more particularly to a novel homoserine lactone derivative represented by the structural formula. and has the potential to be used as an acid amide herbicide and medicine.
本発明は、メタノール資化性微生物菌体が本発明のホモ
セリンラクトン誘導体を含有するとの新知見に基づ〈発
明である。The present invention is based on the new finding that methanol-assimilating microbial cells contain the homoserine lactone derivative of the present invention.
本発明のホモセリンラクトン誘導体（以下、本発明化合
物と記す）は、前記のような構造式で表わされ、Ｎ−ヘ
キサデカノイル−２アミノ−４ブタノリドまたはＮ−ヘ
キサデカノイル−ホモセリンラクトンと称することがで
きる。The homoserine lactone derivative of the present invention (hereinafter referred to as the compound of the present invention) is represented by the above structural formula and is called N-hexadecanoyl-2-amino-4-butanolide or N-hexadecanoyl-homoserine lactone. be able to.
本発明化合物の理化学的性状はつぎの通りである。The physicochemical properties of the compound of the present invention are as follows.
１ 元素分析値（％） Ｃ２゜Ｈｓｔ Ｎ Ｏｓ計
算値 Ｃ７Ｏ−８Ｄ Ｈ１０，９１
Ｎ ４，１５ ０ １４．１６
実測値 Ｃ７０−８６Ｈ１ｌ−０６
Ｎ ４．Ｑ９ ０ １３６５
２分子量
３３９（質量スペクトルによる）
３、融点
１３７〜１３８℃
４、紫外線吸収スペクトル
λ ＣＨＡｏｌ（２０５ｍ４ （ε＝５８．ｎｏ）ａ
ｘ
５ 赤外線吸収スペクトル（ＫＢｒ法による）第１図
６ 核磁気共鳴吸収スペクトル
第２図 ”ＣＮＭＲスペクトル
第３図 ’ＨＮＭＲスペクトル
Ｚ 溶解度
メタノール、工〃／−ル、インプロパツール、フタノー
ル、ベンゼン、トルエン、アセトンに可溶
エーテル、ヘキサンには難溶、水には不溶
８、 結晶の色および性状
白色針状結晶（アセトンから再結晶したもの）
前記の理化学的性質特に１．２．４．５および６の性質
から本発明化合物の構造式を下記の如く確認したつ
すなわち、
ｚ
しかして本発明の化合物は有機化学的方法および生化学
的方法によって得られる。有機化学的方法としては、た
とえば、ホモ上１１ンを脱水閉環して得られるホモセリ
ンラクトンと、パルミチン酸とを反応させる方法がある
。また、生化学的方法としては、たとえばメタノール資
化性微生物の菌体から抽出して得られる。メタノール資
化性微生物には特に制限はないが、通常はたとえばメタ
ノモナス属、メチロモナス属、チオバチルス属、プロタ
ミノバクタ−属、パラコツカス属およびシユードモナス
属のそれぞれに属するメタノール資化性細菌が使用され
ろ。1 Elemental analysis value (%) C2°Hst N Os Calculated value C7O-8D H10,91 N 4,15 0 14.16 Actual value C70-86H1l-06 N 4. Q9 0 1365 2 Molecular weight 339 (according to mass spectrum) 3. Melting point 137-138°C 4. Ultraviolet absorption spectrum λ CHAol (205 m4 (ε=58.no) a
x 5 Infrared absorption spectrum (by KBr method) Figure 1 6 Nuclear magnetic resonance absorption spectrum Figure 2 CNMR spectrum Figure 3 'HNMR spectrum Z Solubility methanol, alcohol, impropatol, phthanol, benzene, toluene , ether soluble in acetone, sparingly soluble in hexane, insoluble in water 8, Color and properties of crystals White needle-like crystals (recrystallized from acetone) The above physical and chemical properties, especially 1.2.4.5 and From the properties of 6, the structural formula of the compound of the present invention was confirmed as follows: z The compound of the present invention can be obtained by organic chemical methods and biochemical methods. There is a method of reacting homoserine lactone obtained by dehydration and ring closure of Methanol with palmitic acid.Also, as a biochemical method, for example, methanol can be obtained by extraction from the cells of methanol-assimilating microorganisms. Although there are no particular restrictions on the assimilating microorganism, methanol assimilating bacteria belonging to the genus Methanomonas, Methylomonas, Thiobacillus, Protaminobacter, Paracoccus and Pseudomonas are usually used.
このメタノール資化性細菌の代表例として、たとえばメ
タノモナス メタノオキシダンス（Ｍｅｔｈａｎｏｍｏ
ｎａｓ ｍｅｔｈａｎｏｏｘｉｄａｎｃｅ）、メチロモ
ナス ルブラム（Ｍｅｔｈｙｌｏｍｏｎａｓ ｒｕｌ）
ｒｏｍ ）、チオバチルス ノベルス（Ｔｈ１ｏｂａｃ
ｉｌｌｕｓｎｏｖｅｌｌｕｓ ）、プロタミノバクタ−
ルバー（Ｐｒｏ ｔａｍｉｎｏｂａｃｔｅｒ ｒｕｂｅ
ｒ ）、バラフッカスプニド１）フイカンス（Ｐａｒａ
ｃｏｃｃｕｓ ｄｅｎｉｔｒｉｆｉ−ｃａｎｓ ）およ
びシュードモナス メタノリカ（Ｐｓｅｕｄｏｍｏｎａ
ｓ ｍｅｔｈａｎｏｌｉｃａ ） などがある口これ
らのメタノール資化性細菌は、メタノ−法により培養さ
れる。A typical example of this methanol-assimilating bacterium is Methanomonas methanooxidans.
nas methanooxidance), Methylomonas rubrum (Methylomonas rul)
rom), Thiobacillus novels (Th1obac
illus novellus), Protaminobacter
Pro taminobacter rube
r), Parafuccus spnido 1) Fucans (Para
coccus denitrifi-cans) and Pseudomonas methanolica (Pseudomonas
These methanol-assimilating bacteria are cultured by the methanol method.
またメタノール資化性微生物菌体からの本発明の化合物
の抽出には、たとえば、メタノール、エタノール、イン
プロパツールおよびブタメールなどの低級アルコール、
アセトン、ベンゼン５−
ならびにトルエンなどの有機溶媒が使用される。In addition, for the extraction of the compound of the present invention from methanol-assimilating microbial cells, for example, lower alcohols such as methanol, ethanol, impropatol and butamele,
Organic solvents such as acetone, benzene, and toluene are used.
本発明により、有用な物質である新規なホモセリンラク
トン誘導体が得られる、
実施例
純水１ノあたり （ＮＨａ）ｘ８０ａ ３１１ 、
ＫＨ２ｐｏ４１．４ 、ｌｉ’ 、 ＮａｔＨＰＯ４２
，１！！、ＰＪＩ Ｓｏ ４ ・７Ｈｘ ＯＯ，２、ｉ
ｉ’ ％ＣａＣ１ｔ−２Ｈ，０３Ｃ１’Ｎ？、ＦｅＣ＊
ＨｓＯｔ・ＸＨ，０３０１ｎ９、ＭｎＣｌ２・４Ｈｚ０
５ｍｇ、Ｚｎ ８０４ ・７１−１．０ ５Ｑ、Ｃｕ
ＳＯ４・５Ｈｔ０ ０ 、５ 、！ｉ’およびビタミン
混合液１ゴを溶解し、ｐＨが６．５に調整された液５Ｉ
！を１０Ｊ容培養槽に入れ、１２０℃で２０分間殺菌し
た後、メタノール ５０Ｉを無菌的に添加し、これを培
地とした。According to the present invention, a novel homoserine lactone derivative, which is a useful substance, can be obtained.
KH2po41.4, li', NatHPO42
,1! ! , PJI So 4 ・7Hx OO,2,i
i'%CaC1t-2H,03C1'N? , FeC*
HsOt・XH, 0301n9, MnCl2・4Hz0
5mg, Zn 804 ・71-1.0 5Q, Cu
SO4・5Ht0 0, 5,! Solution 5I in which pH i' and vitamin mixture 1 are dissolved and the pH is adjusted to 6.5.
! was placed in a 10 J culture tank and sterilized at 120°C for 20 minutes, then methanol 50I was added aseptically and this was used as a culture medium.
なお上記のビタミン混合液の組成は
ビオチン ２（１４
パントテン酸カルシウム ４■
葉 酸 ２０μｇイノシ
トール ２０卿
ニフ千ン酸 ４１ｎ９６−
ピリドキ８量酸塩 ４即
チアミン塩酸塩 ４■
ｐ−７ミノ安息香酸 ２ｍｇ
リボフラビ７ ２■
純 水 １０００ＷＩｌであ
る。The composition of the above vitamin mixture is: biotin 2 (14) calcium pantothenate 4 ■ folic acid 20 μg inositol 20 Niphthonic acid 41 n96-pyridoxyoctamate 4 immediate thiamine hydrochloride 4 ■ p-7 minobenzoic acid 2 mg riboflavin 7 2 ■ Pure water 1000 WIl.
これに前記と同様な培地を用いて６０℃で４８時間前培
養されたパラフッカス デニトリフィカンス（ＩＦＯ１
３３０１）の菌体な含む前培養液１．５容量％接種し、
培養期間中の培養液のｐＨが６．５に維持されるように
アンモニア水を補給しながら培養温度５０°Ｃ１攪拌回
転数７００ （ｐ−ｍ 、通気量１ ｖ、ｖ、ｍで通気
攪拌培養を行なった。１２時間の増殖誘導期間の後、対
数増殖期となり対数増殖期では世代時間３゜５時間で増
殖し、培養開始４８時間後に培養液のメタノール濃度は
０．００１ ｗｔ％以下となった。この培養液を遠心分
離して菌体を分離回収し、この菌体を１００℃で１０時
間乾燥して培養液１１あたり２．８ｇの乾燥菌体を得た
。Parafuccus denitrificans (IFO1) was precultured at 60°C for 48 hours using the same medium as above.
3301) was inoculated with 1.5% by volume of a preculture solution containing bacterial cells,
While supplementing ammonia water to maintain the pH of the culture solution at 6.5 during the culture period, culture with aeration at a culture temperature of 50°C and agitation rotation speed of 700 (p-m, aeration volume of 1 v, v, m). After a 12-hour growth induction period, the cells entered a logarithmic growth phase, and in the logarithmic growth phase, they proliferated with a generation time of 3.5 hours, and 48 hours after the start of culture, the methanol concentration of the culture solution was 0.001 wt% or less. This culture solution was centrifuged to separate and collect the bacterial cells, which were then dried at 100° C. for 10 hours to obtain 2.8 g of dry bacterial cells per 11 of the culture solution.
この菌体１４．９にアセトン２ｏｏｍｌを加え、４０°
Ｃ１５時間攪拌下で抽出し、フィルターにて除菌後、本
発明化合物であるホモセリンラクトン誘導体を含む抽出
液を得た。Add 2 ooml of acetone to this bacterial cell 14.9, and
After extraction under stirring for 15 hours and sterilization using a filter, an extract containing a homoserine lactone derivative, which is a compound of the present invention, was obtained.
次に抽出液を一２０°Ｃｌ２Ｏ時間冷却した、析出した
白色粗結晶を炉取し、ヘキサン １００ｍ１、エーテル
１００７で逐次洗浄後、アセトンより再結晶して白色
針状結晶品ホモセリンラクトン誘導体を得Ｔこう
菌体からの収量はＯ−５ｍｇ／ｇ−ｃｅｌＩ であっ
た、この物質はつぎの性質を示した。Next, the extract was cooled for 1-20°CCl2O hours, and the precipitated white crude crystals were collected in a furnace, washed successively with 100ml of hexane and ether 1007, and then recrystallized from acetone to obtain a white needle-shaped homoserine lactone derivative. The yield from the bacterial cells was O-5 mg/g-celI. This substance showed the following properties.
元素分析値 Ｃ，。）１．、 Ｎｏ。Elemental analysis value C. )1. , No.
Ｃ７Ｏ−Ｂ６ ＨＩＬ、０６
Ｎ ４．０９ ０ １ｊ６５
分 子 ｉ ３３９（質量スペクトルによる）融
点 １３７〜１３８℃
紫外線吸収スペクトル
λＣＨ３０Ｈ２０５ｍμ（ε＝５８．００）ａｘ
赤外線吸収スペクトル（ＫＢｒ法） 第１図核磁気共
鳴スペクトル 第２図および第６図C7O-B6 HIL, 06 N 4.09 0 1j65 molecule i 339 (by mass spectrum) fusion
Point 137-138℃ Ultraviolet absorption spectrum λCH30H205mμ (ε=58.00) ax Infrared absorption spectrum (KBr method) Figure 1 Nuclear magnetic resonance spectrum Figures 2 and 6
第１図は赤外線吸収スペクトル 第２図および第３図はそれぞれ核磁気共鳴スペクトル である。 特許出願人 三菱瓦斯化学株式会社 代表者長野和吉 ９− Figure 1 shows the infrared absorption spectrum. Figures 2 and 3 are nuclear magnetic resonance spectra, respectively. It is. Patent applicant: Mitsubishi Gas Chemical Co., Ltd. Representative Kazuyoshi Nagano 9-
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19214981A JPS5842869B2 (en) | 1981-11-30 | 1981-11-30 | Homoserine lactone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19214981A JPS5842869B2 (en) | 1981-11-30 | 1981-11-30 | Homoserine lactone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5896079A true JPS5896079A (en) | 1983-06-07 |
| JPS5842869B2 JPS5842869B2 (en) | 1983-09-22 |
Family
ID=16286508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19214981A Expired JPS5842869B2 (en) | 1981-11-30 | 1981-11-30 | Homoserine lactone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5842869B2 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999027786A1 (en) * | 1997-12-04 | 1999-06-10 | The University Of Nottingham | Control of biofilm formation |
| US6455031B1 (en) | 1997-06-18 | 2002-09-24 | David G Davies | Methods and compositions for controlling biofilm development |
| KR100424845B1 (en) * | 1997-09-09 | 2004-05-17 | 씨제이 주식회사 | Method for preparing lactone compounds using polystyrene resin |
| US6756404B2 (en) | 1998-06-18 | 2004-06-29 | The Research & Development Institute, Inc. | Autoinducer compounds |
| US7442798B2 (en) | 2000-08-31 | 2008-10-28 | The University Of Iowa Research Foundation | Autoinducer molecules and uses therefor |
| JP2014023489A (en) * | 2012-07-27 | 2014-02-06 | Sumitomo Heavy Ind Ltd | Paracoccus bacterium |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6011385U (en) * | 1983-07-04 | 1985-01-25 | 三菱電機株式会社 | Elevator position display device |
-
1981
- 1981-11-30 JP JP19214981A patent/JPS5842869B2/en not_active Expired
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6455031B1 (en) | 1997-06-18 | 2002-09-24 | David G Davies | Methods and compositions for controlling biofilm development |
| US7094394B2 (en) | 1997-06-18 | 2006-08-22 | Montana State University | Methods and compositions for controlling biofilm development |
| KR100424845B1 (en) * | 1997-09-09 | 2004-05-17 | 씨제이 주식회사 | Method for preparing lactone compounds using polystyrene resin |
| WO1999027786A1 (en) * | 1997-12-04 | 1999-06-10 | The University Of Nottingham | Control of biofilm formation |
| US6756404B2 (en) | 1998-06-18 | 2004-06-29 | The Research & Development Institute, Inc. | Autoinducer compounds |
| US7078435B2 (en) | 1998-06-18 | 2006-07-18 | Montana State University | Autoinducer compounds |
| US7442798B2 (en) | 2000-08-31 | 2008-10-28 | The University Of Iowa Research Foundation | Autoinducer molecules and uses therefor |
| JP2014023489A (en) * | 2012-07-27 | 2014-02-06 | Sumitomo Heavy Ind Ltd | Paracoccus bacterium |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5842869B2 (en) | 1983-09-22 |
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