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JPS58146289A - Novel physiologically active substance i-639b and its preparation - Google Patents

Novel physiologically active substance i-639b and its preparation

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Publication number
JPS58146289A
JPS58146289A JP2811582A JP2811582A JPS58146289A JP S58146289 A JPS58146289 A JP S58146289A JP 2811582 A JP2811582 A JP 2811582A JP 2811582 A JP2811582 A JP 2811582A JP S58146289 A JPS58146289 A JP S58146289A
Authority
JP
Japan
Prior art keywords
physiologically active
active substance
substance
novel physiologically
culture
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
Application number
JP2811582A
Other languages
Japanese (ja)
Inventor
Toshiaki Iwamoto
岩元 俊朗
Akira Hirota
広田 陽
Shoji Shima
島 昭二
Heiichi Sakai
酒井 平一
Akira Isogai
磯貝 彰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to JP2811582A priority Critical patent/JPS58146289A/en
Publication of JPS58146289A publication Critical patent/JPS58146289A/en
Pending legal-status Critical Current

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  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

PURPOSE:To prepare a novel physiologically active substance I-639B having activity to inhibit the growth of a root even with its small amount, by cultivating a fungus belonging to the genus Aspergillus. CONSTITUTION:A fungus such as Aspergillus niger I-639 (FERM-P 6322) belonging to the genus Aspergillus, capable of producing a novel physiologically active substance I-639B, is inoculated into a nutritive medium, cultivated at 10-40 deg.C, preferably at 20-30 deg.C for about 2-30 days, and the novel physiologically active substance I-639B shown by the formula is collected from the culture.

Description

【発明の詳細な説明】 本発明は新生理活性物質エーロ59Bおよびその製造法
に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new physiologically active substance Aero59B and a method for producing the same.

本発明の新生理活性物質エーロ59Bは下記の構造式で
示されるN−メチル−トランス−2,5−ジメチル−N
′−シンナモイルピペラジンであり、その理化学的性質
は次の通りである。
The new physiologically active substance Aero59B of the present invention is represented by the following structural formula: N-methyl-trans-2,5-dimethyl-N
'-cinnamoylpiperazine, and its physicochemical properties are as follows.

1) 分子量:25B(マススペクトル)2)分子式’
 016 H22N、0 5)旋光性:〔α)o −+1o 5.2°(0=1.
1.Mθ0H)4)  紫外部吸収スペクトル: 第1
図に示し7た通り。λmax280nrn(ε= 22
400) 5)  赤外部吸収スペクトル:第2図に示した通り。
1) Molecular weight: 25B (mass spectrum) 2) Molecular formula'
016 H22N, 0 5) Optical rotation: [α) o −+1o 5.2° (0=1.
1. Mθ0H) 4) Ultraviolet absorption spectrum: 1st
As shown in Figure 7. λmax280nrn(ε=22
400) 5) Infrared absorption spectrum: As shown in Figure 2.

6) 核謎翅膿スー9トル:第3図に示した通り。6) Nuclear mystery wing pus 9 tors: As shown in Figure 3.

(/ 7) 呈色反応; ドラー丁ソドル反応、0−)IJジ
ン−に工反応が陽性8)溶解性 、 メタノール、エタ
ノール、酢酸エチル、クロロホルム。
(/7) Color reaction; Doler-Ding-Sodol reaction, 0-) IJ-gin reaction is positive. 8) Solubility, methanol, ethanol, ethyl acetate, chloroform.

ベンゼンに易溶、n−へ午サン、11−へブタンに可溶
、水に錘溶である。
It is easily soluble in benzene, soluble in n-hebutane and 11-hebutane, and slightly soluble in water.

9)駿1質の色:無色、油状物質、空気中で次第に黄色
に着色する。
9) Color of Shun 1 substance: Colorless, oily substance, gradually turns yellow in the air.

10)  安定性:酸性では不安定、中性〜アルカリ性
で比較的安定である。
10) Stability: Unstable in acidic conditions, relatively stable in neutral to alkaline conditions.

本発明の新生理活性物質、T −659B (CF、、
アスペルギルス属に属する当該物pの生産能を有する糸
状菌を培地に培養し、培養物から当該物質を採1”yす
ることによって製造することができる。
The new physiologically active substance of the present invention, T-659B (CF,
It can be produced by culturing a filamentous fungus belonging to the genus Aspergillus and having the ability to produce the substance in a medium, and collecting the substance from the culture.

新生理活性物質ニー 639Bの生産能を有する糸状菌
としては、たとえば土壌から分離さオ]たアスペルギル
ス(Aspergillus )属に属する糸状菌、ア
スペルキルス、ニガーエーロ39(’AJ117105
)かある。本菌株の菌学的性質U K、 B、 Rap
θr andD、 L、 Fennell著「ザ・ジー
ナス・アスペルギルス」(1965)第293頁に従い
検索しまた結果、アスペルギルス・ニガーの同種とみな
されることからアスペルキルス・ニガーと同定1−た。
Examples of filamentous fungi capable of producing the new physiologically active substance Ni 639B include filamentous fungi belonging to the genus Aspergillus that were isolated from soil, Aspergillus niger, and Nigaero 39 ('AJ117105).
) or there is. Mycological properties of this strain UK, B, Rap
A search was conducted according to θr and D.L. Fennell, "The Genus Aspergillus" (1965), p. 293, and the result was that it was identified as Aspergillus niger since it was considered to be the same species as Aspergillus niger.

本菌株は倣工研に寄託さねており、その寄託番号はFE
BM P−6522号である。
This strain has not been deposited with the Institute of Imitation Technology, and its deposit number is FE.
It is BM P-6522.

新生理活性物質エーロ59Bは、上記糸状菌を原則的に
一般糸状菌の培養方法に準じて固体培養。
The new physiologically active substance Aero 59B is obtained by culturing the above filamentous fungus on a solid state in principle in accordance with the culture method for general filamentous fungi.

液体培養法のいずれかの方法で培養し、培養物から分離
、採取することにより得られる0、ここで培地の炭素源
としてシュクロース、グルコース、澱粉など、窒素源と
して硝酸ソーダ、フスマ、大豆粉などがあり、さらにリ
ン酸1カリウム、硝酸マグネシウム、塩化カルシウム、
硫酸第1鉄などの無機地類や酵母エキス、′:j−ン。
0 obtained by culturing by any of the liquid culture methods and separating and collecting from the culture. Here, the carbon source of the medium is sucrose, glucose, starch, etc., and the nitrogen source is sodium nitrate, bran, soybean flour. In addition, monopotassium phosphate, magnesium nitrate, calcium chloride,
Inorganic substances such as ferrous sulfate and yeast extract, ':j-n.

ステイープ・リカー、麦芽エキスなどの微生物の生育を
促進したり、目的とする物質の生産間の向上に資する成
分を添加することができる。
Components that promote the growth of microorganisms, such as staple liquor and malt extract, or that contribute to improving the production of the target substance, can be added.

十記糸状菌を10〜40°C1望ましl:l:20〜′
50°Cで2〜60日程度培養することにより目的とす
るエーロ59B物質が生成する。培養物から■−659
B物質を単離するには通常の培養生産物の単離に用いら
れる手法を適用することができ、たとえは培養物から常
法により菌体等のl1Iif形分を除いた液体区分また
は固体培養物に対し溶媒伸出、シリカゲルクロマトグラ
フィ、ゲル濾過などを血相する、。
Ten filamentous fungi at 10~40°C1 l:l:20~'
The desired Aero59B substance is produced by culturing at 50°C for about 2 to 60 days. ■-659 from culture
To isolate Substance B, methods used for the isolation of ordinary culture products can be applied, for example, liquid division or solid culture in which l1Iif components such as bacterial bodies are removed from the culture by a conventional method. We perform solvent elongation, silica gel chromatography, gel filtration, etc. on substances.

本発明の新生理活性物質エーロ59Bは以下に示す生理
活性を有している。
The new physiologically active substance Aero59B of the present invention has the following physiological activities.

a)抗菌性 スタフィロコッカス・アウレス、バチルス・ズブチリス
、エシェリヒア・コリ、シュードモナス・アエルギノー
サなどの細菌やギャンディダ・アルビカンス、ザッカロ
ミセス・セレビシェ、ペニシリウム・クリゾゲナムなど
の真菌に対して100μf/mlでは抗菌作用を示さな
かつプこ。なお、細菌に−)いては栄養寒天、真菌につ
いてはサブロー寒天を用い、寒天希釈法で測定し、た。
a) Antibacterial properties Shows antibacterial activity at 100 μf/ml against bacteria such as Staphylococcus aures, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa, and fungi such as Gandida albicans, Zaccharomyces cerevisiae, and Penicillium chrysogenum. Nakatsupuko. The measurements were carried out by the agar dilution method using nutrient agar for bacteria and Sabouraud agar for fungi.

b)植物生理活性 シャーレ中でレタス種子を発芽させ、(の供給水中にエ
ーロ59B物質を含ませ、根の伸長に対する阻害作用を
観察した。結果を第1表に示す。
b) Plant Physiological Activity Lettuce seeds were germinated in a petri dish, Aero 59B substance was included in the water supplied, and the inhibitory effect on root elongation was observed. The results are shown in Table 1.

第1表 08 026 100      40 200      70 表から明らかなように、I−(S−39B物質はh]成
りの1!(濃度で根の生長を阻害する活性を有している
。本物質はこのような活性を示すことから除草剤等への
用遼が期待できる。
Table 1 08 026 100 40 200 70 As is clear from the table, the substance S-39B has the activity of inhibiting root growth at a concentration of 1! Because it exhibits such activity, it can be expected to be used as a herbicide.

次に、本発明の実施例を示す。Next, examples of the present invention will be shown.

実施例 1tの平底三角フラスコに小麦フスマ5017’と水5
51を加え、120°Cで20分間2回オートクレーブ
殺菌した。
In the flat bottom Erlenmeyer flask of Example 1t, wheat bran 5017' and water 5
51 was added and sterilized by autoclaving twice for 20 minutes at 120°C.

一方、サブロー寒天斜面培地上で30°Cにて1週間培
養したアスペルギルス・ニガー エーロ59 (AJ1
17105) (rmRbrp−6s22)の胞子を上
記フスマ培地に接種し、時々攪拌しなから30°Cで1
3日間培養した。
On the other hand, Aspergillus niger aero 59 (AJ1) was cultured on Sabouraud agar slant medium at 30°C for one week.
17105) (rmRbrp-6s22) was inoculated into the above bran medium and incubated at 30°C for 1 hour without stirring occasionally.
It was cultured for 3 days.

この培養フラスコ2本を集め、酢酸エチル1.41で抽
出した。酢酸エチル層に0.lN−H0t水溶液1tを
加え、■−659B物質を水層に転溶した。この水層を
取り、アンモニアを添加してアルカリ性とした後、再び
酢酸エチル1tを加えてエーロ59B物質を抽出し、こ
の酢酸エチル層を濃縮して油状物質9511?を得た。
The two culture flasks were collected and extracted with 1.41 g of ethyl acetate. 0.0 to the ethyl acetate layer. 1 ton of 1N-H0t aqueous solution was added to transfer and dissolve the -659B substance into the aqueous layer. This aqueous layer is taken, ammonia is added to make it alkaline, 1 ton of ethyl acetate is added again to extract the Aero 59B substance, and this ethyl acetate layer is concentrated to make an oily substance 9511? I got it.

このようにして得た油状物質をシリカゲル(ワコーゲル
)カラムにかけ、クロロホルムーエタノール混液を10
0 : 1から10θ;6まで混合比を変えて溶出した
。溶出したニー669物質はドラーケンドルフ反応によ
って検出することができる。活性部分を集め、再度シリ
カゲルカラムにかけ、クロロホルム−エタノール混液(
1oo : 2)で溶出(7、得られた活性部分を濃M
LだのちセファデックスLl(−20にかけ、エーテル
−ヘプタン混1合溶媒で溶出し7た。次に、活性画分を
濃縮し、油状物質としてエーロ59B物質55譜を得だ
。本物質は前記した理化学的性質をイjしていることを
確かめた。
The oily substance thus obtained was applied to a silica gel (Wako gel) column, and a chloroform-ethanol mixture was added to
Elution was carried out by changing the mixing ratio from 0:1 to 10θ:6. The eluted Ni669 substance can be detected by Drakendorff reaction. The active parts were collected, applied to a silica gel column again, and added to a chloroform-ethanol mixture (
Elute with 1oo:2) (7, the obtained active part is concentrated
After that, it was applied to Sephadex Ll (-20) and eluted with a mixed solvent of ether and heptane.Next, the active fraction was concentrated to obtain Aero 59B substance 55 as an oily substance.This substance was described above. It was confirmed that the physical and chemical properties of

【図面の簡単な説明】[Brief explanation of the drawing]

第1図0エーロ59B物質の紫外部吸収スペクトル(メ
タノール)、第2図は当該物質の赤夕)線吸収スペクト
ル(CC4)+第5図は当該物質ノ核磁気共鳴スペクト
ル(aDcz3)である。 特許出願人  酒 井 平 − −7=
Figure 1 shows the ultraviolet absorption spectrum (methanol) of the 0Aero59B substance, Figure 2 shows the red light absorption spectrum (CC4) of the substance, and Figure 5 shows the nuclear magnetic resonance spectrum (aDcz3) of the substance. Patent applicant Hei Sakai − −7=

Claims (1)

【特許請求の範囲】 1)下記の構造を有する新生理活性物質エーロ59B。 H3 2) アスペルギルス属に属し新生理活性物質ニー 6
39Bの生産能を有すZ菌株を培養し、培養物から新生
理活性物質エーロ39Bを採取することを特徴とする新
生理活性物質1−639Bの製造法。
[Claims] 1) A new physiologically active substance Aero59B having the following structure. H3 2) A new physiologically active substance belonging to the genus Aspergillus 6
A method for producing a new physiologically active substance 1-639B, which comprises culturing a Z strain having the ability to produce 39B, and collecting the new physiologically active substance Aero 39B from the culture.
JP2811582A 1982-02-25 1982-02-25 Novel physiologically active substance i-639b and its preparation Pending JPS58146289A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2811582A JPS58146289A (en) 1982-02-25 1982-02-25 Novel physiologically active substance i-639b and its preparation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2811582A JPS58146289A (en) 1982-02-25 1982-02-25 Novel physiologically active substance i-639b and its preparation

Publications (1)

Publication Number Publication Date
JPS58146289A true JPS58146289A (en) 1983-08-31

Family

ID=12239808

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2811582A Pending JPS58146289A (en) 1982-02-25 1982-02-25 Novel physiologically active substance i-639b and its preparation

Country Status (1)

Country Link
JP (1) JPS58146289A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0633819U (en) * 1992-03-16 1994-05-06 車体工業株式会社 Part take-out mechanism in assembly parts quantitative feeder
US7637045B2 (en) 2004-07-06 2009-12-29 Asagicreate Co., Ltd. Surface light source and electrically illuminated signboard

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0633819U (en) * 1992-03-16 1994-05-06 車体工業株式会社 Part take-out mechanism in assembly parts quantitative feeder
US7637045B2 (en) 2004-07-06 2009-12-29 Asagicreate Co., Ltd. Surface light source and electrically illuminated signboard

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