JPH0374679B2 - - Google Patents
Info
- Publication number
- JPH0374679B2 JPH0374679B2 JP61301156A JP30115686A JPH0374679B2 JP H0374679 B2 JPH0374679 B2 JP H0374679B2 JP 61301156 A JP61301156 A JP 61301156A JP 30115686 A JP30115686 A JP 30115686A JP H0374679 B2 JPH0374679 B2 JP H0374679B2
- Authority
- JP
- Japan
- Prior art keywords
- substance
- antibiotic
- producing
- agar
- structural formula
- 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 22
- 230000003115 biocidal effect Effects 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 229940088710 antibiotic agent Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 241000187747 Streptomyces Species 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000004151 quinonyl group Chemical group 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000576755 Sclerotia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- VLAPMBHFAWRUQP-UHFFFAOYSA-L molybdic acid Chemical compound O[Mo](O)(=O)=O VLAPMBHFAWRUQP-UHFFFAOYSA-L 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000006877 oatmeal agar Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compounds Of Unknown Constitution (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
産業上の利用分野
本発明は新規抗生物質SF2446物質及びその製
造法に関するものである。
従来の技術及び発明が解決しようとする問題点
従来、数多くの抗生物質が発明、発見され、人
体用医薬品、動物用医薬品、農薬等の分野で実用
化されている。しかしながら、まだ有効な物質が
見出されていないため解決されていない医療或い
は産業の分野が数多く残されている。例えば、一
般細菌及びマイコプラズマにより発症する感染症
は単独感染のほか他の細菌と混合感染する極めて
厄介な病気であり、この分野では強力でしかも広
範囲な抗菌活性と抗マイコプラズマ活性を持つ新
規な抗生物質を提供することが常に要望されてい
る。
本発明者らは以上のような点に着目し、新規な
抗生物質を提供するとともに、その製造法を確立
することによつてこれを解決しようとするもので
ある。
問題点を解決するための手段
本発明者らは、ストレプトマイセス属に属する
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し、その有効物質を
採取することに成功した。更に、本発明者らは、
この有効物質をSF2446物質と命名した。
本発明のSF2446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) 色及び形状：赤褐色結晶
(2) 元素分析値：C58.28％，H5.19％，N1.97％
(3) 分子式：C34H35NO15
(4) マススペクトル（FD−MS）：ｍ／z698
（MH+）
(5) 融点：195〜200℃（分解）
(6) 紫外部及び可視部吸収スペクトル：第１図に
示す。
λMeOH naxnm（Ｅ１％
1cm）：218（554），230sh（368），
252（357），258（351），273sh（290），419（67），
472（70）
λ0.1N HCl-MeOH naxnm（Ｅ１％
1cm：218（556），230sh
（374），252（359），258（354），273sh（297），
418（72），472（75）
λ0.1N NaOH-MeOH naxnm（Ｅ１％
1cm）：215（586），244
（435），295sh（171），582（111）
(7) 赤外線吸収スペクトル：第２図に示す。
λKBr naxcm-1：3400，2940，2840，1730，1680，
1660，1620，1570，1510，1470，1420，
1380，1310，1270，1220，1170，1150，
1120，1090，1030，950，880，820
(8) 1H NMRスペクトル：重クロロホルム溶液
中，TMSを基準物質として測定した400M
Hz 1HNMRスペクトルを第３図に示す。
δ（ppm）：1.36（3H，ｄ），2.40（3H，ｓ），2.51
（1H，ｄ），3.13（1H，dd），3.33（1H，brd），
3.34（1H，dq），3.41（3H，ｓ），3.55（1H，
dd），3.61（3H，ｓ），3.69（1H，dd），3.72
（1H，ddd），3.80（3H，ｓ），3.85（3H，ｓ），
4.66（1H，ｄ），4.68（1H，dd），4.96（1H，
dd），5.22（1H，br ｓ），5.87（1H，br ｓ），
6.54（1H，br ｓ），6.86（1H，ｄ），8.21（1H，
ｓ），12.08（1H，ｓ），14.18（1H，ｓ）
δ（ppm）：2.51，4.66，5.22，6.86，12.08，14.18
のピークはD2Oを添加すると消失する。
(9) 13C NMRスペクトル：重クロロホルム溶液
中、TMSを基準物質として測定した100MHz
13C NMRスペクトルを第４図に示す。
δ（ppm）：195.7，189.6，188.2，178.9，171.6，
162.0，159.7，147.0，142.9，142.6，139.9，
133.7，124.1，123.8，119.7，118.5，116.1，
109.8，104.1，84.6，82.8，79.7，79.3，78.9，
75.2，73.4，62.8，62.5，61.2，52.7，52.4，
38.3，24.1，18.2
(10) 呈色反応：10％硫酸、モリブデン酸試薬に陽
性である。
(11) 溶解性：メタノール、クロロホルムに僅かに
溶け、酢酸エチル、アセトンに溶け難く、
水、ヘキサンに溶けない。
(12) 薄層クロマトグラフイー：
担 体：シリカゲルプレート（メルク社製）
展開溶媒系 RF値
アセトン−ヘキサン（２：１） 0.72
クロロホルム−メタノール（30：１）0.41
酢酸エチル ０・23
(13) 塩基性、酸性、中性の区別：弱酸性物質
以上述べた化学構造式および理化学的性状か
ら、本物質はキノン骨格を有する抗生物質であ
る。そこで上記の化学構造式および理化学的性状
とキノン骨格を有する既知抗生物質のそれとを比
較したところ、それらのいずれとも異なり明確に
区別される。従つて、SF2446物質は新規の抗生
物質であると判断された。
本発明に使用される新規抗生物質SF2446物質
の生産菌の一例としては、兵庫県の土壌から新た
に分離されたSF2446株がある。
SF2446株の菌学的性状は下記の通りである。
形態
基生菌糸は長く伸張し、よく分岐し、通常の
条件下では分断しない。気菌糸の着生は貧弱で
あるが、オートミール寒天、スターチ寒天、グ
リセロール・アスパラギン寒天、シユクロー
ス・硝酸塩寒天等で着生し、胞子形成も認めら
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波状、ルー
プ状、フツク状、あるいは不完全な螺旋状とな
る。電子顕微鏡による観察では、胞子は円筒型
ないし楕円型で、0.5〜1.1×0.6〜1.3μmの大き
さを有し、表面はしわ状（rugose）ないし刺
状（spiny）である。胞子は通常50個以上連鎖
する。胞子〓、運動性胞子、菌核等は観察され
ない。
各種培地上の生育状態
SF2446株の各種培地上の生育状態は第１表
に示す通りである。色の記載について〔〕内に
示す標準はコンテイーナー・コーポレーシヨ
ン・オブ・アメリカ（Container Corporation
of Amer ica）社製の「カラー・ハーモニー・
マニアル（Col or Harmony Maumal）」に記
載されているものを用いた。観察は28℃で14〜
21日間培養後に行なつた。
INDUSTRIAL APPLICATION FIELD The present invention relates to a novel antibiotic SF2446 substance and a method for producing the same. Background Art and Problems to be Solved by the Invention Conventionally, many antibiotics have been invented and discovered, and have been put to practical use in the fields of human medicine, veterinary medicine, agricultural chemicals, and the like. However, there are still many medical and industrial fields that remain unsolved because no effective substances have been found. For example, infectious diseases caused by common bacteria and mycoplasma are extremely troublesome diseases that can occur alone or in combination with other bacteria. It is always requested to provide The present inventors have focused on the above-mentioned points, and aim to solve the problems by providing a new antibiotic and establishing a method for producing the same. Means for Solving the Problems The present inventors have discovered that by culturing a specific strain belonging to the genus Streptomyces, a substance that has a strong growth-inhibiting effect on various bacteria is produced and accumulated in the culture. They discovered that the substance was effective and succeeded in collecting its effective substance. Furthermore, the present inventors
This effective substance was named SF2446 substance. The SF2446 substance of the present invention has the following chemical structural formula and physical and chemical properties. (1) Color and shape: Reddish brown crystal (2) Elemental analysis: C58.28%, H5.19%, N1.97% (3) Molecular formula: C 34 H 35 NO 15 (4) Mass spectrum (FD-MS ): m/z698
(MH + ) (5) Melting point: 195-200°C (decomposition) (6) Ultraviolet and visible absorption spectra: Shown in Figure 1. λ MeOH nax nm (E1% 1cm): 218 (554), 230sh (368),
252 (357), 258 (351), 273sh (290), 419 (67),
472 (70) λ 0.1N HCl-MeOH nax nm (E1% 1cm: 218 (556), 230sh
(374), 252 (359), 258 (354), 273sh (297),
418 (72), 472 (75) λ 0.1N NaOH-MeOH nax nm (E1% 1cm): 215 (586), 244
(435), 295sh (171), 582 (111) (7) Infrared absorption spectrum: Shown in Figure 2. λ KBr nax cm -1 : 3400, 2940, 2840, 1730, 1680,
1660, 1620, 1570, 1510, 1470, 1420,
1380, 1310, 1270, 1220, 1170, 1150,
1120, 1090, 1030, 950, 880, 820 (8) 1 H NMR spectrum: 400M measured in deuterated chloroform solution with TMS as reference material
The Hz 1 HNMR spectrum is shown in Figure 3. δ (ppm): 1.36 (3H, d), 2.40 (3H, s), 2.51
(1H, d), 3.13 (1H, dd), 3.33 (1H, brd),
3.34 (1H, dq), 3.41 (3H, s), 3.55 (1H,
dd), 3.61 (3H, s), 3.69 (1H, dd), 3.72
(1H, ddd), 3.80 (3H, s), 3.85 (3H, s),
4.66 (1H, d), 4.68 (1H, dd), 4.96 (1H,
dd), 5.22 (1H, br s), 5.87 (1H, br s),
6.54 (1H, br s), 6.86 (1H, d), 8.21 (1H,
s), 12.08 (1H, s), 14.18 (1H, s) δ (ppm): 2.51, 4.66, 5.22, 6.86, 12.08, 14.18
The peak disappears when D 2 O is added. (9) 13 C NMR spectrum: 100MHz measured in deuterated chloroform solution using TMS as a reference material
The 13 C NMR spectrum is shown in Figure 4. δ (ppm): 195.7, 189.6, 188.2, 178.9, 171.6,
162.0, 159.7, 147.0, 142.9, 142.6, 139.9,
133.7, 124.1, 123.8, 119.7, 118.5, 116.1,
109.8, 104.1, 84.6, 82.8, 79.7, 79.3, 78.9,
75.2, 73.4, 62.8, 62.5, 61.2, 52.7, 52.4,
38.3, 24.1, 18.2 (10) Color reaction: Positive for 10% sulfuric acid and molybdic acid reagents. (11) Solubility: Slightly soluble in methanol and chloroform, slightly soluble in ethyl acetate and acetone,
Insoluble in water and hexane. (12) Thin layer chromatography: Support: Silica gel plate (manufactured by Merck) Developing solvent system RF value Acetone-hexane (2:1) 0.72 Chloroform-methanol (30:1) 0.41 Ethyl acetate 0.23 (13) Distinction between basic, acidic, and neutral: weakly acidic substances Based on the chemical structural formula and physical and chemical properties described above, this substance is an antibiotic with a quinone skeleton. Therefore, when the above chemical structural formula and physical and chemical properties were compared with those of known antibiotics having a quinone skeleton, it was clearly distinguished from any of them. Therefore, SF2446 substance was determined to be a new antibiotic. An example of a bacterium producing the novel antibiotic SF2446 used in the present invention is strain SF2446, which was newly isolated from soil in Hyogo Prefecture. The mycological properties of SF2446 strain are as follows. Morphology The basal hyphae are elongated, well branched, and do not divide under normal conditions. Although the aerial mycelium is poorly attached, it grows on oatmeal agar, starch agar, glycerol/asparagine agar, sucrose/nitrate agar, etc., and spore formation is also observed. The branching of aerial hyphae is simple, and no axle branching is observed. The spore chain at the tip of the aerial hyphae is wavy, loop-like, hook-like, or incompletely spiral. When observed using an electron microscope, the spores are cylindrical or oval in shape, measuring 0.5 to 1.1 x 0.6 to 1.3 μm, and have a rugose or spiny surface. Spores usually form chains of 50 or more. Spores, motile spores, sclerotia, etc. were not observed. Growth status on various media The growth status of SF2446 strain on various media is as shown in Table 1. Regarding color descriptions: Standards shown in [ ] are those of Container Corporation of America.
Color Harmony
The material described in "Color Harmony Maumal" was used. Observation was performed at 28℃ for 14~
This was done after 21 days of culture.
【表】
パラギン寒天
[Table] Paragin agar
Claims (1)
SF2446物質生産菌を培養し、その培養物から抗
生物質SF2446物質を採取することを特徴とする
抗生物質SF2446物質の製造法。[Claims] 1. SF2446 substance having the following chemical structural formula. 2 Antibiotics belonging to the genus Streptomyces
A method for producing an antibiotic SF2446 substance, which comprises culturing SF2446 substance-producing bacteria and collecting the antibiotic SF2446 substance from the culture.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61301156A JPS63154695A (en) | 1986-12-19 | 1986-12-19 | Novel antibiotic substance sf2446 and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61301156A JPS63154695A (en) | 1986-12-19 | 1986-12-19 | Novel antibiotic substance sf2446 and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63154695A JPS63154695A (en) | 1988-06-27 |
| JPH0374679B2 true JPH0374679B2 (en) | 1991-11-27 |
Family
ID=17893453
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61301156A Granted JPS63154695A (en) | 1986-12-19 | 1986-12-19 | Novel antibiotic substance sf2446 and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63154695A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007520637A (en) * | 2003-08-08 | 2007-07-26 | ジュン ホ キム | Far-infrared irradiation heater, far-infrared dyeing apparatus, and dyeing method using far-infrared rays |
| US8754054B2 (en) | 2010-07-09 | 2014-06-17 | Albany Molecular Research, Inc. | Antibacterial compounds, methods of making them, and uses thereof |
| AU2016362540B2 (en) | 2015-12-02 | 2022-04-28 | Fondazione Istituto Insubrico Di Ricerca Per La Vita | Antibiotic FIIRV 104/18 complex and the isolated individual factors thereof |
-
1986
- 1986-12-19 JP JP61301156A patent/JPS63154695A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63154695A (en) | 1988-06-27 |
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