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El FIG. Uv ASORPTION OF June 25, 1974 SUMO UMEZAWA ET All 3,819,834 ESPINOMYCIN ANTIBIOTICS AND METHODS OF PREPARING SAMs Original Filled Aug. 7, 1970 3. Sheets-Sheet El% FIG. uv ASORPTION OF ESPNOMYCIN A (0.001 NHCP) 400 200 OO 20 220 230 240 250 26O 270 % WAVELENGTH, my Eicm 400 FIG. 2 UW ABSORPTION OF ESPNOMYCIN B (000 NHC) 300 200 OO 2O 220 230 240 250 260 270 WAVELENGTH, mp. NVENTORS SUMO UMEZAWA, SAMU MACHIDA, SUSUMU SHIOTSU, YAKU KAWAGUCH, SHIGEHIDE MAKINO, KIMIO YOKOTA, KAZUTOSH HONDA. ATTORNEYS June 25, 1974 SUMO UMEZAWA ET All- 3,819,834 ESPINOMYCIN ANTIBIOTICS AND METHODS OF PREPARING SAME Original Filed Aug. 7, 1970 3. Sheets-Sheet 2 3 S. Od S3 8 S. 3 C 3 ill o C Cd 2na co 3 s 95 st 3 a 5 - N St. Es - 2 E | 's c) S. d 2 gf c O > NO ac O S 3 : CO O d 3. 3 s - CN - O - d O d rol O Cd - ? LC2 3 CN 3 urC SS June 25, 1974 SUMO UMEZAWA ET All- 3,819,834 ESPINOMYCIN ANTIBIOTICS AND METHODS OF PREPARING SAME p Original Filed Aug. a 970 3 Sheets-Sheet 3 08H 09 0{7 03 0 00,7 03 || 009008000) 6 8 Ti‘H10NETBAWM 2.9 |_NO‘MONEMOGHA —————? G #7 008||.000X2009,2000€000€000+7 2 -0 08 09 OZ % 3,819,834 United States Patent Office Patented June 25, 1974 1. 2 strain has also been deposited with the American Type 3,819,834 Culture Collection in the United States, and has been ESPNOMYCIN ANTIBIOTICS AND METHODS OF given ATCC Acceptance No. 21574. PREPARNG SAME Sumio Umezawa, Tokyo, Isamu Machida, Hatogaya, It is an object of this invention to provide a new mem Susumu Shiotsu and Kimio Yokota, Urawa, Shigehide ber of antibiotics belonging to the macrollide antibiotics. Makino, Tokyo, Gaku Kawaguchi, Gyoda, and Kazu Another object of this invention is to provide a method toshi Honda, Tokyo, Japan, assignors to Meji Seika for producing Espinomycin antibiotics. Kaisha, Ltd., Tokyo, Japan A further object of the invention is to provide methods Continuation of abandoned application Ser. No. 62,055, of separating crude mixtures of Espinomycin into Espino Aug. 7, 1970. This application Apr. 18, 1972, Ser. No. mycin A and Espinomycin B. 245,178 10 Still another object of this invention is to provide a Int. Cl. A61k 21/00 new type of antibiotic which exhibits a high antibiotic U.S. C. 424-120 8 Claims activity against gram-positive bacteria. Another object of this invention is to provide an anti ABSTRACT OF THE DISCLOSURE biotic exhibiting high activity against gram-positive bac 5 teria which has a low toxicity to the host. A new group of antibiotics, the Espinomycins, are Yet an additional object of this invention is to provide described along with methods for obtaining them from a new antibiotic exhibiting a favorable absorption from Streptomyces fungicidicus varietus espinomyceticus. The the digestive tract, which is therefore suitable for oral antibiotics belong to the macrollide group of antibiotics, administration. and show a high activity against gram-positive organisms. 20 The foregoing and other objects are obtained in accord They are suitable for oral administration, and show a ance with the present invention which provides a unique low toxicity to the host. strain of Streptomyces fungicidicus, named Streptomyces fungicidicus var. espinomyceticus, and a method for ob This is a continuation of application Ser. No. 62,055 taining and purifying antibiotic substances produced by filed Aug. 7, 1970, now abandoned. 25 this organism. BACKGROUND OF THE INVENTION BRIEF DESCRIPTION OF THE DRAWINGS Field of the invention These and other objects, features, and advantages of The present invention relates generally to new anti 30 the invention will become more fully apparent to those biotics and methods of producing them. More particu skilled in the art from the following description of an larly, the present invention pertains to new and useful illustrative embodiment of the invention, as further illus antibiotics called Espinomycins, and methods of produc trated in the annexed Drawings, in which: ing them from a newly isolated organism, Streptomyces FIG. 1 is the ultraviolet absorption spectrum of Espino fungicidicus varietus espinomyceticus. mycin A in 0.001 NHCl; FIG. 2 is the ultraviolet absorption spectrum of Espino Description of the prior art mycin B in 0.001 NHCl; Many antibiotics have been reported belonging to the FIG. 3 is the infrared absorption spectrum of Espino macrollide group of antibiotics, such as Erythromycin, mycin A measured in KBr tablets; Carbomycin, Oleandomycin, Leucomycin, Spiramycin, 40 FIG. 4 is the infrared absorption spectrum of Espino Josamycin, etc. All of these antibiotics are characterized mycin B measured in KBr tablets; and by having a distinct absorption on infrared spectra at FIG. 5 is a silica gel thin layer chromatogram of around 1720 cm. based on the carbonyl group of a Espinomycin A and Josamycin, schematically illustrated. macro cyclic lactone ring. Those concerned with the de velopment of antibiotics effective against gram-positive DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS bacteria have long recognized the need for antibiotics The Espinomycins of this invention may be prepared which are capable of oral administration due to a high by the fermentation of Streptomyces N-18-90. While rate of transfer into the bloodstream, coupled with a low Espinomycin has the same maximum absorption by ultra toxicity. The present invention fills this need. violet spectroscopy at around 232 mu, as do some of the 50 known macrollide group of antibiotics, the physicochemi SUMMARY OF THE INVENTION cal and biological properties of Espinomycin are entirely The general purpose of this invention is to provide new different from those of the above antibiotics, as is dis and useful antibiotics called Espinomycins, and a method closed hereinafter. for preparing them. Espinomycin is the name given to the Mycological Characteristics of Streptomyces Fungicidicus new group of antibiotics manufactured by the method of Varietus Espinomyceticus this invention. Among them, at least two types of these antibiotics have been isolated which have been designated Morphological features Espinomycin A or Espinomycin B. As used in this specifi cation, the word "Espinomycin' is intended to mean According to microscopic - observation of the espino either Espinomycin A, Espinomycin B, or combinations 60 mycin-producing strain grown on starch ammonium phos thereof. The Espinomycins of this invention are prepared phate agar, an aerial mycelium is observed having a long by the fermentation of Streptomyces N-18-90. main axis. No whorl was observed, but one or two The Streptomyces N-18-90 strain was isolated for the branches were grown from several parts of the aerial first time from a soil sample collected in Ibaragi City, hyphae. The tip of the sporophore often forms an open Osaka Prefecture, Japan, by the present inventors. This 65 spiral, and the spore chain looks berry-like due to the organism strain was deposited with the Fermentation Re involute tight spiral. Typically, there are more than 10 search Institute, Agency of Industrial Science and Tech spores. According to electron microscopy, the size of the nology, Inage City, Chiba Prefecture, Japan, and given spore is irregular, the average being about 1 x 0.8 microns, Acceptance No. 351. The N-18-90 strain was classified and the shape of the spore being typically spherical to as a variant of Streptomyces fungicidicus and was named 70 oval. Many longer spines are observed on the surface of Streptomyces fungicidicus var. espinomyceticus. This the spore. 3,819,834 3 4 Culture Characteristics on Various Media 18. Potato plug 1. Glucose nitrate agar (glucose-Czapek's agar) Thick light brown growth. Aerial mycelium white, Colorless growth, white, dense aerial mycelium, Some sometimes becoming faintly purplish tinge. Plug color times becoming faintly purplish tinge. Reverse gradually unchanged. purplish shade, later dull purple to purplish brown. Light 19. Carrot plug purple to light brownish purple pigment diffuses into the Off-white to light brown, good growth. Aerial mycelium agar. powdery white. No darking of plug. The following physiological properties have been noted 2. Glycerine nitrate aga (glycerine Czapek's agar) which are characteristic of Streptomyces fungicidicus var. Similar to (1) above, but generally only a weak pig O espinomyceticus: mentation. 1. The organism is aerobic, showing good growth over 3. Glucose asparagine agar a pH range of from 5 to 9. No noticeable difference in Off-white to pale brown growth. Aerial mycelium growth was observed over the temperature range of 27 sparse, sometimes becoming white powdery. Pigment 15 C. to 37° C. mostly absent. 2. Liquefaction of gelatin: Weak or none. 3. Hydrolysis of starch: Positive. 4. Glycerine calcium malate agar 4. Tyrosinase reaction: Negative. Thin, colorless growth. Aerial mycelium scant. Pigment 5. Peptonization of milk: Positive. absent. 6. Nitrate reduction: Negative. 20 7. Cellulolytic reaction: Negative. 5. Glucose nitrate solution (glucose Czapek's solution) 8. Chromogenecity action: Negative. Colorless small colonies in bottom of tube, with Small 9. Hemolysis: Positive. colonies on liquid surface. Pigment absent. 10. Liquefaction of coagulated serum: Negative. The carbon utilization properties of Streptomyces 6. Starch agar (starch ammonium sulfate agar) 25 fungicidicus var. espinomyceticus are shown in Table 1 Off-white growth. Aerial mycelium abundant, white in tested on Pridham and Gottlieb's medium. initial stage, later grayish shade with various tones. (This shade is caused by dense sporulation.) Reverse, later pro TABLE 1. duces dull reddish insoluble pigment partially. 30 D-glucose - Maltose Raffinose - 7. Peptone meat extract agar (nutrient agar) D-mannitol -- D-sorbitol D-xylose -- Inositol -- Salicin : Sodium citrate - O-galactose -- L-arabinose Sucrose - Cream-colored growth. Aerial mycelium sparse, white. D-fructose -- Rhamnose - No pigment.
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