Novel antibiotics and process for preparing the same

Claim 2

An antibiotic substance produced by a microorganism belonging to the genus Streptomyces (FERM BP-2087) by culturing said microorganism in a medium suitable for growth thereof at 26 to 30°C for 2 to 7 days under aeration.

Claim 3

The antibiotic substance of Claim 1 which is selected from the group consisting of SF2582 A represented by the formula (A) SF2582 B represented by the formula (B) and SF2582 C represented by the formula (C)

Claim 4

The antibiotic substance of Claim 2, wherein SF2582 A represented by the formula (A) has the following physiochemical properties: 1) Appearance: yellowish orange amorphous powder 2) Melting Point: 235 - 237°C (decomp.) 3) Molecular Formula: C₂₆H₂₆N₃O₈Cℓ [determined by high resolution mass spectrometry of a monoacetyl derivative; found: 585.1492; calcd. for C₂₈H₂₈N₃O₉Cℓ: 585.1512] 4) Mass Spectrum:      SI-MS m/z 544 (M+1)⁺ FD-MS m/s 543 (M)⁺ 5) Specific Rotation: [α] 22 D -51° (c=0.2, methanol) 6) UV Spectrum; as shown in Fig. 1 λ max (nm) (E ) (in methanol solution): 208 (729), 245 shoulder (360), 298 (391), 337 (580), 432 (77) 7) IR Spectrum: as shown in Fig. 2 8) ¹H NMR Spectrum (400 MHz, CDCℓ₃): as shown in Fig. 3 9) ¹³C NMR Spectrum (100 MHz, CDCℓ₃): as shown in Fig. 4 δ (ppm): 196.6 (s), 169.5 (s), 160.5 (s), 150.2 (s), 150.1 (s), 144.1 (s), 140.7 (s), 138.6 (s), 137.6 (s), 129.0 (s), 125.9 (s), 123.4 (s), 119.5 (s), 115.5 (d), 112.4 (s), 107.8 (d), 97.7 (d), 71.1 (s), 61.5 (q), 61.2 (q), 56.3 (q), 54.9 (t), 53.3 (q), 46.3 (t), 42.2 (d), 21.9 (q) 10) Solubility: soluble in methanol, ethyl acetate, acetone, chloroform, or dimethyl sufoxide; insoluble in water or haxane 11) Thin Layer Chromatography (on silica gel plates produced by E. Merck, Darmstadt): Developing Solvent Rf chloroform-methanol (20:1) 0.52 benzene-acetone (2:1) 0.48 toluene-acetone (2:1) 0.45 12) Color Reaction: positive with 10% solfuric acid reagent, Lemieux reagent, Greig-Leaback reagent, and molybdate-sulfuric acid reagent; negative with ninhydrin reagent

Claim 5

The antibiotic substance of Claim 2, wherein SF2582 B represented by the formula (B) has the following physiochemical properties: 1) Appearance: yellowish orange amorphous powder 2) Melting Point: 173 - 175°C (decomp.) 3) Molecular Formula: C₂₆H₂₆N₃O₈Cℓ [determined by high resolution mass spectrometry of a monoacetyl derivative; found: 585.1519; calcd. for C₂₈H₂₈N₃O₉Cℓ: 585.1512] 4) Mass Spectrum:      SI-MS 544 (M+1)⁺ EI-MS 543 (M)⁺ 5) Specific Rotation: [α] 22 D -128° (c=0.2, methanol) 6) UV Spectrum: as shown in Fig. 5 λ max (nm) (E ) (in methanol solution): 210 (991), 320 (563), 400-410 (99) 7) IR Spectrum: as shown in Fig. 6 8) ¹H NMR Spectrum (400 MHz, CDCℓ₃): as shown in Fig. 7 9) ¹³C NMR Spectrum (100 MHz, CDCℓ₃): as shown in Fig. 8 δ (ppm): 196.8 (s), 169.6 (s), 164.7 (s), 151.6 (s), 150.0 (s), 141.6 (s), 140.2 (s), 138.8 (s), 129.1 (s), 128.8 (s), 125.9 (s), 123.0 (s), 118.0 (d), 116.7 (s), 116.6 (s), 108.1 (d), 97.6 (d), 71.0 (s), 61.4 (q), 61.1 (q), 56.2 (q), 53.6 (d), 53.4 (q), 52.5 (t), 33.1 (t), 21.8 (q) 10) Solubility: soluble in methanol, ethyl acetate, acetone, chloroform, or dimethyl sufoxide; insoluble in water or haxane 11) Thin Layer Chromatography (on silica gel plates produced by E. Merck, Darmstadt): Developing Solvent Rf chloroform-methanol (20:1) 0.50 benzene-acetone (2:1) 0.45 toluene-acetone (2:1) 0.44 12) Color Reaction: positive with 10% sulfuric acid reagent, Lemieux reagent, Greig-Leaback reagent, and molybdate-sulfuric acid reagent; negative with ninhydrin reagent

Claim 6

The antibiotic substance of Claim 2, wherein the SF2582 C represented by the formula (C) has the following physiochemical properties: 1) Appearance: orange crystalline powder 2) Melting Point: > 240°C 3) Elementary Analysis: C 59.24%, H 5.12%, N 7.98% 4) Molecular Formula: C₂₆H₂₇N₃O₉ 5) Mass Spectrum: EI-MS m/z 525 (M⁺) 6) Specific Rotation: [α] 22 D -54° (c=0.1, methanol) 7) UV Spectrum: as shown in Fig. 9 λ max (nm) (E ) (in methanol solution): 208 (845), 245 shoulder (450), 297 (473), 336 (690), 432 (93) 8) IR Spectrum: as shown in Fig. 10 9) ¹H NMR Spectrum (400 MHz, DMSO-d₆): as shown in Fig. 11 10) ¹³C NMR Spectrum (100 MHz, DMSO-d₆): as shown in Fig. 12 δ (ppm): 198.1 (s), 169.5 (s), 159.6 (s), 150.5 (s), 149.3 (s), 143.1 (s), 139.9 (s), 139.2 (s), 136.5 (s), 131.4 (s), 125.3 (s), 123.4 (s), 120.0 (s), 114.5 (s), 111.4 (d), 105.9 (d), 98.2 (d), 70.1 (s), 62.6 (t), 61.3 (q), 61.1 (q), 56.1 (q), 54.1 (t), 52.8 (q), 42.5 (d), 20.3 (q) 11) Solubility: easily soluble in pyridine or dimethyl sulfoxide; slightly soluble in methanol; sparingly soluble in chloroform, hexane, ethyl acetate, or water 12) Thin Layer Chromatography (on silica gel plates produced by E. Merck, Darmstadt): Developing Solvent Rf chloroform-methanol (10:1) 0.38 toluene-acetone (1:1) 0.62 13) Color Reaction: positive with 10% sulfuric acid reagent, Lemieux reagent, Greig-Leaback reagent, and molybdate-sulfuric acid reagent; negative with ninhydrin reagent

Claim 7

A process for producing an antibiotic substance of Claim 1 comprising culturing a microorganism belonging to the genus Streptomyces (FERM BP-2087) in a medium suitable for growth thereof at 26 to 30°C for 2 to 7 days under aeration and recovering said antibiotic substance obtained.

Claim 8

The process of Claim 6, wherein said antibiotic substance is recovered by the steps comprising filtering the culture medium to obtain the microbial cells, extracting said antibiotic substance with an organic solvent from said microbial cells and subjecting the extract to silica gel chromatography to recover said antibiotic substance.