Antibiotics saframycins A, B, C, D and E and process for producing the same

An antibiotic substance, saframycin B, having the following physico-chemical characteristics:

• Color and appearance:
• orange-yellow prisms;
• Melting point:
• 108.degree.-109.degree. C.;
• Elementary analysis:
• C:
• 62.36%, H:
• 5.71%, N:
• 7.66%;
• Molecular weight according to mass spectrum:
• 537;
• Empirical formula:
• C.sub.28 H.sub.31 N.sub.3 O.sub.8 ;
• Specific rotation:
• [.alpha]sub.D.sup.20 =-54.4 (C=1.0, methanol);
• Ultraviolet absorption spectrum as shown in FIG. 4:
• UV .lambda..sub.max.sup.methanol nm (log .epsilon.):
• 269 (4.35), 368 (3.13).
• .lambda..sub.min.sup.methanol nm (log .epsilon.):
• 232 (3.86), 330 (3.10);
• Infrared absorption spectrum as shown in FIG. 5:
• IR .nu..sub.max.sup.CHCl.sbsp.3 cm.sup.-1 :
• 3430, 1720, 1690, 1660, 1620;
• NMR spectrum (CDCl.sub.3) as shown in FIG. 6:
• .delta.:
• 1.90 (3H, S), 1.98 (3H, S), 2.23 (3H, S), 2.28 (3H, S), 4.00 (6H, S), 6.28 (1H, bs);
• Solubility:
• Easily soluble:
• Lower alcohols, chloroform, esters, acetone, benzene
• Sparingly soluble:
• Ethyl ether
• Insoluble:
• Water, n-hexane;
• and
• Color reaction:
• Positive in Dragendorff and Meyer reactions, negative in ninhydrin and Ehrlich reactions.

An antibiotic substance, saframycin C, having the following physico-chemical characteristics:

• Color and appearance:
• Orange-red needles;
• Melting point:
• 143.degree.-146.degree. C.;
• Elementary analysis:
• C:
• 61.61%, H:
• 5.96%, N:
• 7.39%;
• Molecular weight according to mass spectrum:
• 567;
• Empirical formula:
• C.sub.29 H.sub.33 N.sub.3 O.sub.9 ;
• Specific rotation:
• [.alpha]sub.D.sup.20 =-20.8.degree. (C=1.0, methanol);
• Ultraviolet absorption spectrum as shown in FIG. 7:
• UV .lambda..sub.max.sup.methanol nm (log .epsilon.):
• 266.5 (4.32), 368 (3.19). .lambda..sub.min.sup.methanol nm (log .epsilon.):
• 230 (3.86), 330 (3.16);
• Infrared absorption spectrum as shown in FIG. 8:
• IR .nu..sub.max.sup.CHCl.sbsp.3 cm.sup.-1 :
• 3400, 1720, 1685, 1655, 1615;
• NMR spectrum (CDCl.sub.3) as shown in FIG. 9:
• .delta.:
• 1.86 (3H, S), 2.00 (3H, S), 2.38 (3H, S),
• 2. 44 (3H, S), 3.46 (3H, S), 3.96 (3H, S), 6.60 (1H, bs);
• Solubility:
• Easily soluble:
• Lower alcohols, chloroform, esters, acetone, benzene
• Sparingly soluble:
• Ethyl ether
• Insoluble:
• Water, n-hexane;
• and
• Color reaction:
• Positive in Dragendorff and Meyer reactions, negative in ninhydrin and Ehrlich reactions.

An antibiotic substance, saframycin D, having the following physico-chemical characteristics:

• Color and appearance:
• Yellow needles;
• Melting point:
• 150.degree.-154.degree. C.;
• Elementary analysis:
• C:
• 60.48%, H:
• 5.68%, N:
• 7.59%;
• Molecular weight according to mass spectrum:
• 553;
• Empirical formula:
• C.sub.28 H.sub.31 N.sub.3 O.sub.9 ;
• Specific rotation:
• [.alpha]sub.D.sup.20 =+141.degree. (C=1.0, methanol);
• Ultraviolet absorption spectrum as seen in FIG. 10:
• UV .lambda..sub.max.sup.methanol nm (log .epsilon.):
• 243 (4.14), 274 (4.24), 369 (3.75).
• .lambda..sub.min.sup.methanol nm (log .epsilon.):
• 231 (4.08), 253 (4.06), 319 (3.30);
• Infrared absorption spectrum as seen in FIG. 11:
• IR .nu..sub.max.sup.CHCl.sbsp.3 cm.sup.-1 :
• 3560, 3400, 1720, 1685, 1660, 1630;
• NMR spectrum (CDCl.sub.3) as seen in FIG. 12:
• .delta.:
• 1.91 (3H, S), 2.17 (3H, S), 2.28 (3H, S), 2.45 (3H, S), 3.97 (3H, S), 4.06 (3H, S);
• Solubility:
• Easily soluble:
• Lower alcohols, chloroform, pyridine
• Sparingly soluble:
• esters, acetone, ethyl ether
• Insoluble:
• Water, n-hexane;
• and
• Color reaction:
• Positive in Dragendorff reaction.

An antibiotic substance, saframycin E, having the following physico-chemical characteristics:

• Color and appearance:
• Yellow powder;
• Melting point:
• 146.degree.-148.degree. C.;
• Elementary analysis:
• C:
• 58.52%, H:
• 5.89%, N:
• 7.36%;
• Molecular weight (converted upon mass spectrum of the corresponding triacetyl derivative):
• 555;
• Empirical formula:
• C.sub.28 H.sub.33 N.sub.3 O.sub.9. H.sub.2 O;
• Specific rotation:
• [.alpha]sub.D.sup.20 =-37.3.degree. (C=0.53;
• methanol);
• Ultraviolet absorption spectrum as seen in FIG. 13:
• UV .lambda..sub.max.sup.methanol nm (log .epsilon.):
• 272 (4.10), 368 (2.93).
• .lambda..sub.min.sup.methanol nm (log .epsilon.):
• 241 (3.84), 340 (2.96);
• Infrared absorption spectrum as seen in FIG. 14:
• IR .nu..sub.max.sup.KBr cm.sup.-1 :
• 3380, 1720, 1685, 1655, 1620;
• NMR spectrum (d-5 pyridine) as seen in FIG. 15:
• .delta.:
• 1.83 (3H, S), 2.17 (3H, S), 2.30 (3H, S), 2.48 (3H, S), 3.82 (3H, S), 3.95 (3H, S), 5.22 (1H, S);
• Solubility:
• Easily soluble:
• Lower alcohols, pyridine
• Sparingly soluble:
• Acetone, esters, chloroform
• Insoluble:
• Water, n-hexane;
• and
• Color reaction:
• Positive in Dragendorff reaction.