JPH0374675B2 - - Google Patents
Info
- Publication number
- JPH0374675B2 JPH0374675B2 JP60102686A JP10268685A JPH0374675B2 JP H0374675 B2 JPH0374675 B2 JP H0374675B2 JP 60102686 A JP60102686 A JP 60102686A JP 10268685 A JP10268685 A JP 10268685A JP H0374675 B2 JPH0374675 B2 JP H0374675B2
- Authority
- JP
- Japan
- Prior art keywords
- substance
- antibiotic
- sodium salt
- agar
- antibiotics
- 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.)
- Expired - Lifetime
Links
- 239000000126 substance Substances 0.000 claims description 32
- 230000003115 biocidal effect Effects 0.000 claims description 11
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 4
- 238000012258 culturing Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 229940124536 anticoccidial agent Drugs 0.000 claims 1
- 239000003224 coccidiostatic agent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 7
- 229940088710 antibiotic agent Drugs 0.000 description 5
- QZVSDERYSHAHPU-LFEMCTADSA-N (2r)-2-[(2s,3r,4s,5s,6s)-2-hydroxy-6-[[(2r,3r,4r,5s,6r,7r,9s)-2-[(5s)-5-[(2r,5r)-5-[(3s,5r,6s)-6-hydroxy-3,5,6-trimethyloxan-2-yl]oxolan-2-yl]oxolan-2-yl]-3,7-dimethoxy-2,4,6-trimethyl-1,10-dioxaspiro[4.5]decan-9-yl]methyl]-4-methoxy-5-[(2s,5s,6r)-5-metho Chemical compound C1([C@H]2CC[C@@H](O2)[C@@H]2CCC(O2)[C@@]2(C)O[C@]3([C@H](C)[C@H]2OC)[C@@H]([C@H](OC)C[C@@H](C[C@H]2[C@]([C@@H](OC)[C@@H](C)[C@@](O)([C@@H](C)C(O)=O)O2)(C)O[C@@H]2O[C@H](C)[C@@H](OC)CC2)O3)C)O[C@](C)(O)[C@H](C)C[C@@H]1C QZVSDERYSHAHPU-LFEMCTADSA-N 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 4
- QZVSDERYSHAHPU-UHFFFAOYSA-N Septamycin Natural products COC1C(C)C2(C(C(OC)CC(CC3C(C(OC)C(C)C(O)(C(C)C(O)=O)O3)(C)OC3OC(C)C(OC)CC3)O2)C)OC1(C)C(O1)CCC1C(O1)CCC1C1OC(C)(O)C(C)CC1C QZVSDERYSHAHPU-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 2
- 239000002555 ionophore Substances 0.000 description 2
- 230000000236 ionophoric effect Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- UQZSVIGPZAULMV-DKWTVANSSA-N (2s)-2,4-diamino-4-oxobutanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OC(=O)[C@@H](N)CC(N)=O UQZSVIGPZAULMV-DKWTVANSSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000007613 bennett's agar Substances 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NLCVKZQQNSCDFU-UHFFFAOYSA-L potassium;sodium;dibromide Chemical compound [Na+].[K+].[Br-].[Br-] NLCVKZQQNSCDFU-UHFFFAOYSA-L 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compounds Of Unknown Constitution (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Description
発明の目的
産業上の利用分野
本発明は新規抗生物質SF−2361物質、その製
造法および用途に関する。
従来の技術
本発明に係わる抗生物質SF−2361物質に近似
する物質としてはセプタマイシン（Septamycin，
ジヤーナル・オブ・アンチビオチクス28巻、854
〜859頁、1975年）及び抗生物質38295物質（特開
昭51−125793、特開昭51−128495）が知られてい
る。
発明の構成
本発明者らはアクチノマデユラ属に属する特定
の菌株を培養することにより、各種細菌に対して
強い発育阻止作用を有する物質が培養物中に生
産、蓄積されることを見出だし、その有効物質を
採取することに成功した。
さらに本発明者らは、この有効物質を単離、精
製してその性質を検討した結果、既知の物質とは
異なる新規抗生物質であることを見い出し、この
有効物質をSF−2361物質と命名した。本発明の
SF−2361物質は下記の化学構造式および理化学
的性状を有する。
(1) 色および形状：
ナトリウム塩 無色針状結晶
(2) 元素分析値：
ナトリウム塩 C61.57％，H8.83％
(3) 分子式：
ナトリウム塩 C48H81O16Na
(4) 分子量：
ナトリウム塩 936（SIMS）
(5) 融点：
ナトリウム塩 178〜180℃（分解）
(6) 比旋光度：
ナトリウム塩［α］25 D−19.9゜（cl，メタノー
ル）
(7) 紫外線吸収スペクトル：
ナトリウム塩の100μｇ／mlメタノール溶液
は210nm〜360nmで特徴的な吸収を示さない。
(8) 赤外線吸収スペクトル：
ナトリウム塩の臭化カリウム錠による赤外線
吸収スペクトルを第１図に示す。
(9) 核磁気共鳴スペクトル：
ナトリウム塩の水素核核磁気共鳴スペクトル
を第２図に示し、炭素核核磁気共鳴スペクトル
を第３図及び第１表に示す。
(10) 呈色反応：
シリカゲル薄層上で硫酸およびエタノール性
バニリン硫酸試薬に陽性（青紫色）、ニンヒド
リン試薬に陰性
(11) 溶解性：
メタノール、クロロホルム、酢酸エチルおよ
びアセトンに易溶、水およびｎ−ヘキサンに難
溶。
(12) シリカゲル薄層クロマトグラフイーのRf値
酢酸エチル−クロロホルム（７：３） 0.66
アセトン−ベンゼン（１：５） 0.46
酢酸エチル−ヘキサン（１：１） 0.48
(13) 塩基性、酸性、中性の区分： 酸性
OBJECTS OF THE INVENTION INDUSTRIAL APPLICATION FIELD OF THE INVENTION The present invention relates to a novel antibiotic SF-2361 substance, its production method and uses. Prior Art A substance similar to the antibiotic SF-2361 substance according to the present invention is Septamycin (Septamycin).
Journal of Antibiotics Volume 28, 854
~859 pages, 1975) and 38295 antibiotic substances (Japanese Patent Application Laid-Open Nos. 51-125793 and 1975-128495) are known. Structure of the Invention The present inventors have discovered that by culturing a specific bacterial strain belonging to the genus Actinomadeula, a substance that has a strong growth-inhibiting effect on various bacteria is produced and accumulated in the culture, and has demonstrated its effectiveness. The material was successfully collected. Furthermore, as a result of isolating and purifying this effective substance and examining its properties, the present inventors discovered that it is a new antibiotic different from known substances, and named this active substance SF-2361 substance. . of the present invention
SF-2361 substance has the following chemical structural formula and physical and chemical properties. (1) Color and shape: Sodium salt Colorless needle crystals (2) Elemental analysis: Sodium salt C61.57%, H8.83% (3) Molecular formula: Sodium salt C 48 H 81 O 16 Na (4) Molecular weight: Sodium salt 936 (SIMS) (5) Melting point: Sodium salt 178-180℃ (decomposed) (6) Specific rotation: Sodium salt [α] 25 D −19.9° (cl, methanol) (7) Ultraviolet absorption spectrum: Sodium A 100 μg/ml methanol solution of the salt shows no characteristic absorption between 210 nm and 360 nm. (8) Infrared absorption spectrum: Figure 1 shows the infrared absorption spectrum of sodium salt potassium bromide tablets. (9) Nuclear magnetic resonance spectrum: The hydrogen nuclear magnetic resonance spectrum of the sodium salt is shown in FIG. 2, and the carbon nuclear magnetic resonance spectrum is shown in FIG. 3 and Table 1. (10) Color reaction: Positive for sulfuric acid and ethanolic vanillin sulfate reagent (blue-purple) on a thin layer of silica gel, negative for ninhydrin reagent (11) Solubility: Easily soluble in methanol, chloroform, ethyl acetate, and acetone, easily soluble in water and Slightly soluble in n-hexane. (12) Rf value of silica gel thin layer chromatography Ethyl acetate-chloroform (7:3) 0.66 Acetone-benzene (1:5) 0.46 Ethyl acetate-hexane (1:1) 0.48 (13) Basic, acidic, medium Sex classification: acidic
【表】【table】
【表】
SF−2361物質の寒天平板希釈法で測定した各
種微生物に対する最小発育阻止濃度を第２表に示
す。[Table] Table 2 shows the minimum inhibitory concentration of SF-2361 substance against various microorganisms measured by the agar plate dilution method.
【表】【table】
【表】
前記のSF−2361物質の化学構造式および理化
学的性状及び生物学的性状を既知抗生物質のそれ
と比較すると、いわゆるポリエーテル系イオノフ
オア抗生物質に分類される。
ポリエーテル系イオノフオア抗生物質の中で
SF−2361物質と同一の分子式（分子量）
C48H81O16Na（936）を有する物質としてセプタ
マイシン（Septamycin，ジヤーナル・オブ・ア
ンチビオチクス28巻、854−859頁、1975年）及び
抗生物質38295物質（特開昭51−125793、特開昭
51−128495）が知られている。セプタマイシンと
は比旋光度、シリカゲル薄層上の呈色反応その他
の理化学的性状が異なる。38295物質とは酢酸エ
チル−クロロホルム（７：３）を展開溶媒とする
シリカゲル薄層クロマトグラフイーでのRf値が
SF−2361物質0.66に対して38295物質は0.52を示
し、また比旋光度その他の理化学的性状も異なる
ことにより区別することができる。従つてSF−
2361物質は新規抗生物質であると判断された。
本発明の新規抗生物質SF−2361物質はアクチ
ノマデユラ類に属するSF−2361物質生産菌を培
養し、その培養物からSF−2361物質を採取する
ことによつて製造される。本発明に使用される
SF−2361物質の生産菌の一例としては、本発明
者らにより愛媛県津島の土壌より新たに分離され
たSF−2361株がある。SF−236株の菌学的性状
は次ぎの通りである。
形態
基生菌糸はよく伸長分岐し、通常の条件下で
は分断しない。気菌糸の着生は極めて貧弱であ
るが、スターチ寒天、グリセロール・アスパラ
ギン寒天およびオートミール寒天で僅かに気菌
糸着生が認められる。気菌糸の分岐は単純分岐
で車軸分岐は見られない。気菌糸先端の胞子連
鎖はループ状あるいはフツク状であり、また疑
似胞子のう様形態（主として直径1.5〜3.0μm）
も観察される。胞子の運動性は観察されない。
電子顕微鏡による観察では、胞子は卵形ないし
楕円形で、大きさは0.5〜0.8×0.7〜1.2μm、表
面構造は、平滑（Smooth）である。胞子は通
常２〜10個連鎖する。
各種培地上の生育状態
SF−2361株の各種寒天培地上での生育状態
は、第３表に示す通りである。培養は28℃で行
ない、観察は14〜21日培養に行なつた。[Table] Comparing the chemical structural formula, physicochemical properties, and biological properties of the substance SF-2361 with those of known antibiotics, it is classified as a so-called polyether ionophore antibiotic. Among polyether ionophore antibiotics
Same molecular formula (molecular weight) as SF-2361 substance
Septamycin (Journal of Antibiotics, Vol. 28 , pp. 854-859, 1975) and Antibiotic 38295 Substance (JP-A-51-125793 , JP-A Akira
51-128495) is known. It differs from septamycin in specific optical rotation, color reaction on a thin silica gel layer, and other physical and chemical properties. 38295 substance has an Rf value in silica gel thin layer chromatography using ethyl acetate-chloroform (7:3) as the developing solvent.
The SF-2361 substance shows a value of 0.66, while the 38295 substance shows a value of 0.52, and can be distinguished by their different specific rotations and other physical and chemical properties. Therefore, SF−
2361 substances were determined to be new antibiotics. The novel antibiotic SF-2361 substance of the present invention is produced by culturing SF-2361 substance-producing bacteria belonging to the Actinomadeula family and collecting the SF-2361 substance from the culture. used in the present invention
An example of a bacterium producing the SF-2361 substance is strain SF-2361, which was newly isolated by the present inventors from soil in Tsushima, Ehime Prefecture. The mycological properties of SF-236 strain are as follows. Morphology The basal hyphae are well elongated and branched, and do not divide under normal conditions. Aerial mycelial attachment is extremely poor, but slight aerial mycelial attachment is observed on starch agar, glycerol-asparagine agar, and oatmeal agar. The branching of aerial hyphae is simple, and no axle branching is observed. The spore chain at the tip of the aerial hyphae is loop-shaped or hook-shaped, and has a pseudosporangial shape (mainly 1.5 to 3.0 μm in diameter).
is also observed. No spore motility is observed.
When observed using an electron microscope, the spores are oval or oval in shape, the size is 0.5-0.8 x 0.7-1.2 μm, and the surface structure is smooth. Spores usually form chains of 2 to 10. Growth status on various media The growth status of SF-2361 strain on various agar media is as shown in Table 3. Cultivation was performed at 28°C, and observations were made after 14 to 21 days of cultivation.
【表】
ベネツト寒天 良好 橙色 なし なし
[Table] Bennett's agar Good Orange None None
Claims (1)
2361物質生産菌を培養し、その培養物から抗生物
質SF−2361物質を採取することを特徴とする抗
生物質SF−2361物質の製造法。 ３ 抗生物質SF−2361物質を有効成分とする抗
コクシジウム剤。[Claims] 1. SF-2361 substance having the following chemical structural formula. 2 Antibiotic SF- belonging to the genus Actinomadeula
1. A method for producing an antibiotic SF-2361 substance, which comprises culturing a 2361 substance-producing bacterium and collecting the antibiotic SF-2361 substance from the culture. 3. Anticoccidial agent containing antibiotic SF-2361 substance as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60102686A JPS61260888A (en) | 1985-05-16 | 1985-05-16 | Novel antibiotic substance sf-2361, production and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60102686A JPS61260888A (en) | 1985-05-16 | 1985-05-16 | Novel antibiotic substance sf-2361, production and use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61260888A JPS61260888A (en) | 1986-11-19 |
| JPH0374675B2 true JPH0374675B2 (en) | 1991-11-27 |
Family
ID=14334122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60102686A Granted JPS61260888A (en) | 1985-05-16 | 1985-05-16 | Novel antibiotic substance sf-2361, production and use thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61260888A (en) |
-
1985
- 1985-05-16 JP JP60102686A patent/JPS61260888A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61260888A (en) | 1986-11-19 |
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