JPS61130250A - Antibiotic caf-0603 - Google Patents
Antibiotic caf-0603Info
- Publication number
- JPS61130250A JPS61130250A JP59253826A JP25382684A JPS61130250A JP S61130250 A JPS61130250 A JP S61130250A JP 59253826 A JP59253826 A JP 59253826A JP 25382684 A JP25382684 A JP 25382684A JP S61130250 A JPS61130250 A JP S61130250A
- Authority
- JP
- Japan
- Prior art keywords
- antibiotic
- caf
- medium
- culture
- methanol
- 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
Links
- 230000003115 biocidal effect Effects 0.000 title abstract description 18
- 239000000126 substance Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 241001149558 Trichoderma virens Species 0.000 abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 abstract description 4
- 241000233866 Fungi Species 0.000 abstract description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 3
- 239000008103 glucose Substances 0.000 abstract description 3
- 229920002472 Starch Polymers 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 239000008107 starch Substances 0.000 abstract description 2
- 235000019698 starch Nutrition 0.000 abstract description 2
- KINNMTBWIQCDPS-UHFFFAOYSA-N 1,1,3-trimethyl-2-[3,7,12,16-tetramethyl-18-(2,2,6-trimethylcyclohexyl)octadecyl]cyclohexane Chemical compound CC1CCCC(C)(C)C1CCC(C)CCCC(C)CCCCC(C)CCCC(C)CCC1C(C)CCCC1(C)C KINNMTBWIQCDPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 230000001580 bacterial effect Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009422 growth inhibiting effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 1
- CTIHYOZNWNAKHD-UHFFFAOYSA-N 4-methoxybenzaldehyde;sulfuric acid Chemical compound OS(O)(=O)=O.COC1=CC=C(C=O)C=C1 CTIHYOZNWNAKHD-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000896533 Gliocladium Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 239000006159 Sabouraud's agar Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000002518 antifoaming agent 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
- 229940041514 candida albicans extract Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004362 fungal culture Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000012449 sabouraud dextrose agar Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- -1 ucrose Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】 産業上の利用分野 本発明は新規の抗生物質に関する。[Detailed description of the invention] Industrial applications The present invention relates to new antibiotics.
従来の技術
本発明の抗生物質は、カロタン型セスキテルペンジオー
ルの新規の化合物であるが、その類似化金物の中には抗
真菌活性を有するものは知られていない。BACKGROUND OF THE INVENTION The antibiotic of the present invention is a novel carotane-type sesquiterpenediol compound, but none of its metal analogues are known to have antifungal activity.
発明が解決しようとする問題点
本発明の目的は、真菌類に対して増殖抑制作用を示す、
新規な抗生物質を提供するにある。Problems to be Solved by the Invention The object of the present invention is to provide a method that exhibits a growth inhibiting effect on fungi.
Our goal is to provide new antibiotics.
問題点を解決・・争・するための手段
本発明の目的物質を生産する菌種は、［グリオクラディ
ウム・ビレンス（Ｇｌｉｏｃｌａｄｉｌｌｍ Ｖｉｒｅ
ｎｓ ）工ＦＯ９１６６Ｊとして財団法人「発酵研究所
」に寄託されているものである。この菌種を培養して得
られる本発明の目的物質を［抗生物質ＣＡＦ−０６０３
Ｊと命名した。Means for solving/disputing problems The bacterial species that produces the target substance of the present invention is [Gliocladium virens].
ns) Engineering FO9166J has been deposited with the Fermentation Research Institute. The target substance of the present invention obtained by culturing this bacterial strain [Antibiotic CAF-0603
I named it J.
抗生物質ＣＡＦ−０６０３の生産は大略、一般の発酵生
産物を生産する場合に準じ、各種栄養物を含む培地でグ
リオクラディウム・ビレンスエＦＯ９１６６を好気的条
件で培養することにより行う。The production of antibiotic CAF-0603 is generally carried out by culturing Gliocladium virensae FO9166 under aerobic conditions in a medium containing various nutrients, as in the production of general fermentation products.
培地は主として液体培地を用い、炭素源としてグルコー
ス、／ユクロース、 糖ｔ スターチナトを単独かま
たは混合して用い、窒素源としては肉エキス、酵母エキ
ス、大豆粉、ポリペプトンなどを単独かまたは混合して
用いる。その他、グリオクラディウム・ビレンス １Ｆ
Ｏ９１６６の生育を助け、抗生物質ＣＡＦ−０６０３の
生産を促進する有機物および無機物を適当に添加するこ
とができる。消泡剤としてはアデカノール、／リコンな
どを用いることができる。The medium is mainly a liquid medium, and the carbon sources are glucose, ucrose, and starch, either singly or in combination, and the nitrogen sources are meat extract, yeast extract, soybean flour, polypeptone, etc., singly or in combination. use Others, Gliocladium virens 1F
Organic and inorganic substances that aid the growth of O9166 and promote the production of antibiotic CAF-0603 can be appropriately added. As the antifoaming agent, Adekanol, /Recon, etc. can be used.
培養方法は振盪培養７通気攪拌培養などの好気的培養が
適しており、ＰＨ４〜８，２５〜３０℃で２〜６日間、
望ましくはｐＨ４，５〜７．５．２８〜３０℃で４日間
培養する。For the culture method, aerobic culture such as shaking culture 7 aerated agitation culture is suitable, and the culture is carried out at pH 4-8, 25-30℃ for 2-6 days.
Desirably, the culture is carried out at pH 4.5 to 7.5 and 28 to 30°C for 4 days.
この培養により生産された抗生物質 Ｃ１ＡＦ−０６０
３を単離するには発酵生産物を採取する一般的な方法に
準じて行えばよい。抗生物質ｃｈＦ−０６０３は主に菌
体中に含有されるので、たとえば次の方法が効果的であ
る。Antibiotic C1AF-060 produced by this culture
3 can be isolated according to a general method for collecting fermentation products. Since the antibiotic chF-0603 is mainly contained in bacterial cells, the following method is effective, for example.
すなわち、培養終了後、遠心分離または濾過により分離
した菌体から活性物質を低級アルコール。That is, after culturing, the active substance is extracted from the bacterial cells separated by centrifugation or filtration with lower alcohol.
アセトノなどの有機溶媒で抽出し、この抽出ｉｔ濃縮後
、ｎ−ヘキサノ、酢酸エチル、ベンゼン。Extract with an organic solvent such as acetonate, and after concentrating this extraction, n-hexano, ethyl acetate, and benzene.
ゾロラフ状とし、ｎ−へキサン、ベンゼン、酢酸エチル
、アセトン、メタノールなどの有ｉｉ媒に溶解後、ノリ
力ゲル〔たとえばＥ、メルク社（西独）製、キーゼルゲ
ル６０（商品名）〕を用いたカラムクロマトグラフィー
および逆相分配カラム〔たとえば野村化学社製、ディベ
ロシル０ＤＳ（商品名）〕を用いた分取高速液体クロマ
トグラフィー（溶離液ニアセトニトリル−水系）によっ
て精製。After making it into a zololaf form and dissolving it in a medium such as n-hexane, benzene, ethyl acetate, acetone, or methanol, a glue gel (for example, E, manufactured by Merck & Co., Ltd. (West Germany), Kieselgel 60 (trade name)) was used. Purification by column chromatography and preparative high performance liquid chromatography (eluent: niacetonitrile-water system) using a reverse phase distribution column (for example, Nomura Chemical Co., Ltd., Diverosil 0DS (trade name)).
単離することができる。Can be isolated.
抗生物質ＣＡＦ−０６０３は、
構造式
で表される化合物であり、下記の理化学的性質を有する
。Antibiotic CAF-0603 is a compound represented by the structural formula and has the following physical and chemical properties.
理化学的性質
（１）元素分析（１ｊｌｌｌ定値２％）Ｃ： ７ ５
． ５ ４ ； Ｈ： １． ０ ８（２）分子
量
高分解能Ｅ工ＭＳ ｍ／ｚ ２３ａ１９０７ 実測
値ｍ／ｚ ２３ａｉ９０９ 計算値
（３）分子式
％式％
〔α〕−−２６．２°（ｃ＝０．５． メタノール中
）（６）紫外線吸収スペクトル
メタノール中（２５ｏｐｇ／ｙ）で測定した結果を第１
図に示す。Physical and chemical properties (1) Elemental analysis (1jllll fixed value 2%) C: 7 5
．． 5 4; H: 1. 0 8 (2) Molecular weight high resolution E-engineering MS m/z 23a1907 Actual value m/z 23ai909 Calculated value (3) Molecular formula % formula % [α]--26.2° (c=0.5. in methanol) ( 6) Ultraviolet absorption spectrum measured in methanol (25 opg/y)
As shown in the figure.
（７）赤外線吸収スペクトル ＫＢｒ錠で測定した結果を第２図に示す。(7) Infrared absorption spectrum Figure 2 shows the results measured using KBr tablets.
（８）’Ｈ−ＮＭＲスペクトル
重クロロホルム中、２０（：ＪＭＨｚで測定した結果全
第６図に示す。(8)'H-NMR spectrum Measured in deuterated chloroform at 20 (:JMHz) All results are shown in FIG.
（９）１３ｃ −Ｎ ＭＲスペクトル
重クりロホルム中、５０ＭＨ２で測定した結果を第４図
に示す。(9) 13c -N MR spectrum The results of measurement in chloroform at 50 MH2 are shown in FIG.
α０溶媒に対する溶解性 水に不溶。Solubility in α0 solvent Insoluble in water.
メタノール、エタノール、酢酸エチル、ぺ／ゼ／。Methanol, ethanol, ethyl acetate, p/ze/.
クロロホルム、ｎ−ヘキサ／にｑｇ。Chloroform, n-hex/qg.
ａη呈色反応
ニンヒドリン、塩化第二鉄、２，４−ジニトロフェニル
ヒドラジンに対して陰性を示すが、ヨード、バニリン−
硫酸、アニスアルデヒド−硫酸に対しては陽性を示す。aη Color reaction shows negative for ninhydrin, ferric chloride, and 2,4-dinitrophenylhydrazine, but for iodine, vanillin-
It shows positive for sulfuric acid and anisaldehyde-sulfuric acid.
（６）塩基性、中性、酸性の区別
中 性
α１物質の色と性状
無色針状結晶
作 用
抗生物質０ＡＦ−０６０３は真菌類に対し、優れた増殖
抑制作用を有する。(6) Distinction between basic, neutral, and acidic Color and properties of neutral α1 substance: colorless needle-shaped crystals Effect: Antibiotic 0AF-0603 has an excellent growth-inhibiting effect on fungi.
以下、試験例を挙げて抗生物質ＯＡＦ−０６０３の作用
を具体的に説明する。Hereinafter, the action of the antibiotic OAF-0603 will be specifically explained using test examples.
試験例
真菌の培地としては、各種ａ度の抗生物質０ＡＦ−０６
０５を含むサブロー寒天を用い、イノキュラムサイズ１
０５ｃＦＵ７−で抗生物質０ＡＦ−０６０３の各種菌に
対するＭＩＣｊ （最小発育阻止濃度）を測定し、その
抗菌作用を検討した。As a test example fungal culture medium, various A grade antibiotics 0AF-06 were used.
Inoculum size 1 using Sabouraud agar containing 05
The MICj (minimum inhibitory concentration) of the antibiotic 0AF-0603 against various bacteria was measured using 05cFU7-, and its antibacterial effect was investigated.
その結果を次表に示す。The results are shown in the table below.
抗菌作用
発明の効果
本発明の目的物である抗生物質ＣＡＦ−０６０３は、以
上の諸性質を有することから、優れた抗菌作用を有する
新規の抗生物質であり、真菌症などの治療薬として有用
である。Antibacterial action Effect of the invention The antibiotic CAF-0603, which is the object of the present invention, has the above-mentioned properties, and therefore is a new antibiotic with excellent antibacterial action, and is useful as a therapeutic agent for fungal diseases. be.
実施例 以下、実施例を挙げて本発明を具体的に説明する。Example The present invention will be specifically described below with reference to Examples.
実施例
１）５を容、ジャーファーメンタ−にグルコース４％、
ポリペプトン１％からなる培地５ｔｆいれ、オートクレ
ーブで滅菌した。これと同じ培地で３０℃、３日間振盪
培養したグリオクラディウム・ビレンス エＦＯ９１６
６菌液を前記滅菌培地に３％接種し、３０℃で４日間攪
拌通気培養した。培養終了後、ジャ−７ァーメンタ−２
基分。Example 1) 5, glucose 4% in jar fermenter,
A 5 tf medium containing 1% polypeptone was placed in the medium and sterilized in an autoclave. Gliocladium virens eFO916 was cultured with shaking in the same medium at 30°C for 3 days.
The sterilized medium was inoculated with 6 bacterial solutions at 3%, and cultured with stirring and aeration at 30° C. for 4 days. After completion of culture, jar 7 amenter 2
Base.
６ｔの培養液を合わせて濾過し、菌体を得た。得られた
菌体をメタノール６００−で２回抽出し、この抽出液を
合わせて減圧下メタノールを溜去して得られたシロップ
に２００−の水を加え、等量の酢酸エチルで２回抽出し
た。酢酸エチル画分を合わせ無水硫酸ナトリウムで乾燥
後、減圧下濃縮して褐色シロップを得た。6 tons of culture solution were combined and filtered to obtain bacterial cells. The resulting bacterial cells were extracted twice with 600 methanol, and the extracts were combined and the methanol was distilled off under reduced pressure. To the syrup obtained, 200 m water was added, and the mixture was extracted twice with an equal volume of ethyl acetate. did. The ethyl acetate fractions were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a brown syrup.
シロ、プにアセトン１７！およびベンゼン２〇−を加え
、ベンゼンで平衡化したシリカゲル〔キーゼルゲル６０
（商品名）、Ｅ、メルク社（西独）製〕カラム（１００
−）に吸着させた。ベンゼン−アセトン（９６：４）混
合溶媒で溶出し、１５０〜５００ｍに溶出してくる活性
区分を集め、これを減圧濃縮してシロップ１．５ｆｉ得
た。Shiro, acetone 17! and benzene 20- and equilibrated with benzene [Kieselgel 60
(Product name), E, manufactured by Merck & Co. (West Germany)] Column (100
-) was adsorbed. It was eluted with a benzene-acetone (96:4) mixed solvent, and the active fraction eluted from 150 to 500 m was collected and concentrated under reduced pressure to obtain 1.5 fi of syrup.
２）前項１）で得られたシロ、プを最少量のクロロホル
ムで希釈後、アセトニトリルを加え、６−の溶液とした
。次いで、分取高速液体クロマトグラフィー〔カラム：
ディベロシル０ＤＳ（商品名）。2) The mixture obtained in 1) above was diluted with the minimum amount of chloroform, and then acetonitrile was added to prepare a solution of 6-. Next, preparative high performance liquid chromatography [column:
Diverosil 0DS (product name).
野村化学社製、２０Ｘ２５０闇；溶媒：６３％アセトニ
トリル〕により、保持時間 ２３．８〜２１５分に溶出
される分画を繰り返し分取して、これを減圧下濃縮後、
活性物質をクロロホルムに転溶させた。無水硫酸マグネ
シウムで乾燥後、減圧濃縮して生じた抗生物質ＣＡＦ−
０６０３の無色針状結晶１４７■を単離した。Nomura Chemical Co., Ltd., 20X250 dark; solvent: 63% acetonitrile], the fraction eluted at a retention time of 23.8 to 215 minutes was repeatedly collected, and after concentrating it under reduced pressure,
The active substance was transferred into chloroform. Antibiotic CAF- produced by drying with anhydrous magnesium sulfate and concentration under reduced pressure.
147 cm of colorless needle-like crystals of 0603 were isolated.
融点 ８２〜８４℃Melting point: 82-84℃
第１図はメタノール中で測定した抗生物質０ＡＦ−０６
０３の紫外線吸収スペクトルを示し、第２図は同じ（Ｋ
Ｂｒ錠で測定した赤外線吸収スペクトルを示し、第３図
は同じく重クロロホルム中、２００ＭＨｚで測定した”
Ｈ−ＮＭＲスペクトルを示し、第４図は同じく重クロロ
ホルム中、５０ＭＨ２で測定した１３Ｃ−ＮＭＲスペク
トルを示す。
特許出願人 大正製薬株式会社
代理人 弁理士 北 川 富 造図面の浄；ｔ
（内′Ｇ（こ変更なし）
図面の浄：径（内容に変更なし）
★Ｓ繰
手続補正書（方式）
昭和６０年４月１１日Figure 1 shows antibiotic 0AF-06 measured in methanol.
Figure 2 shows the ultraviolet absorption spectrum of 03.
The infrared absorption spectrum measured with a Br tablet is shown in Figure 3, which was also measured in deuterated chloroform at 200MHz.
The H-NMR spectrum is shown, and FIG. 4 shows the 13C-NMR spectrum also measured at 50 MH2 in deuterated chloroform. Patent applicant Taisho Pharmaceutical Co., Ltd. Agent Patent attorney Tomi Kitagawa
(Inner G (no change) Drawing cleanliness: Diameter (no change in content) ★S procedure amendment (method) April 11, 1985
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59253826A JPS61130250A (en) | 1984-11-30 | 1984-11-30 | Antibiotic caf-0603 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59253826A JPS61130250A (en) | 1984-11-30 | 1984-11-30 | Antibiotic caf-0603 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS61130250A true JPS61130250A (en) | 1986-06-18 |
Family
ID=17256668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59253826A Pending JPS61130250A (en) | 1984-11-30 | 1984-11-30 | Antibiotic caf-0603 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61130250A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399587A (en) * | 1993-12-13 | 1995-03-21 | Merck & Co., Inc. | Biologically active compounds |
| CN108467337A (en) * | 2018-04-23 | 2018-08-31 | 中国科学院烟台海岸带研究所 | A kind of sesquiterpene alcohols compound and its preparation and application |
| CN108484363A (en) * | 2018-04-23 | 2018-09-04 | 中国科学院烟台海岸带研究所 | A kind of three alcohol compound of sequiterpene and its preparation and application |
-
1984
- 1984-11-30 JP JP59253826A patent/JPS61130250A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5399587A (en) * | 1993-12-13 | 1995-03-21 | Merck & Co., Inc. | Biologically active compounds |
| WO1995016442A1 (en) * | 1993-12-13 | 1995-06-22 | Merck & Co., Inc. | Novel potassium channel agonist produced from trichoderma virens |
| CN108467337A (en) * | 2018-04-23 | 2018-08-31 | 中国科学院烟台海岸带研究所 | A kind of sesquiterpene alcohols compound and its preparation and application |
| CN108484363A (en) * | 2018-04-23 | 2018-09-04 | 中国科学院烟台海岸带研究所 | A kind of three alcohol compound of sequiterpene and its preparation and application |
| CN108467337B (en) * | 2018-04-23 | 2020-12-15 | 中国科学院烟台海岸带研究所 | Sesquiterpene enol compound and preparation and application thereof |
| CN108484363B (en) * | 2018-04-23 | 2020-12-15 | 中国科学院烟台海岸带研究所 | Sesquiterpene triol compound and preparation and application thereof |
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