Substance DC114-A1

Details Substance DC114-A1 Substance DC114-A1

1995-03-01

1996-07-16

Trinh, Ba Kim

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549414, 549415, 549417, 549418, C07D31178, C07D31194

Patent

active

055368506

DESCRIPTION:

BRIEF SUMMARY
This application is filed under 35 USC 371 of PCT/JP94/00956 dated Jun. 14, 1994.


TECHNICAL FIELD

The present invention relates to a novel substance DC114-A1 which has antibacterial and anti-tumor activity and is useful as antibacterial and anti-tumor agents.


BACKGROUND ART

Compound DC114-C which has a skeleton related to the present compound and which is represented by the following formula (II): ##STR2## has been known (EP-A-0429209).


DISCLOSURE OF THE INVENTION

The present invention provides a novel substance DC114-A1 having antibacterial and anti-tumor activity which is represented by the following formula (I): ##STR3##
This compound can be produced by culturing a microorganism belonging to the genus Streptomyces.
The present invention is described in detail below.
The physicochemical properties of DC114-A1 are shown below.
(1) Molecular weight: 548
(2) Molecular formula: C.sub.29 H.sub.24 O.sub.11
(3) Mass spectrum: High resolution FAB mass spectrum (matrix: m-nitrobenzyl alcohol): m/z amu
Found: 549.1402 (M+H).sup.+
Calculated for C.sub.29 H.sub.25 O.sub.11 : 549.1397
(4) Specific rotation: [.alpha]sub.D.sup.26 =-53.8.degree. (c=0.03, acetone)
(5) UV absorption spectrum (measured in methanol) .lambda.max(.epsilon.); 224.5 (18,000), 275.0 (32,100), 408.0 (7,800)
(6) IR absorption spectrum (measured by the KBr method): .nu.max cm.sup.-1 ; 3469, 1726, 1697, 1653, 1396, 1294, 1271, 1117, 1093.
(7) .sup.13 C-NMR spectrum (100 MHz, DMSO-d.sub.6 solution): .delta. ppm (multiplicity); 206.0(s), 195.0(s), 189.2(s), 178.1(s), 164.3(s), 158.4(s), 154.2(s), 138.5(s), 128.2(s), 127.5(s), 125.0(s), 121.6(s), 120.8(d), 112.9(d), 110.8(d), 110.7(s), 75.3(d), 74.5(d), 64.2(d), 64.1(d), 63.9(s), 57.8(d), 57.1(s), 48.5(d), 43.7(t), 42.3(t), 22.9(q), 14.3(q), 12.5(q).
(8) .sup.1 H-NMR spectrum (400 MHz, DMSO-d.sub.6 solution): .delta. ppm [integration, multiplicity, coupling constant (Hz) ]; 12.34(1H, br.s), 8.18(1H, s), 7.83(1H, s ), 6.46(1H, s), 5.47(1H, m), 4.85 (1H, dd, 11.4, 3.1), 4.51(1H, dq, 6.7, 6.7), 4.43(1H, br.d, 6.7), 4.31(1H, s), 3.26(1H, ddd, 6.6, 4.1, 2.5), 3.19(1H, d, 6.6), 2.95(1H, t, 4.7), 2.88(1H, dd, 5.0, 2.5), 2.85(1H, dd, 14.0, 11.4), 2.80(3H, d, 0.8), 2.57(1H, dd, 14.0, 3.1), 1.88(3H, s), 1.15(3H, d, 6.7) .
(9) Solubility: Soluble in dimethylsulfoxide (DMSO), methanol and acetone; sparingly soluble in water, ethyl acetate, chloroform and n-hexane.
(10) Color reaction: Positive to the iodine test
(11) Color and property of the substance: Yellow powder
(12) Thin layer chromatography: silica gel thin layer (HPTLC plate Art. 15647, produced by Merck & Co., Inc.)
The Rf value obtained by using toluene:acetone solution (2:1 v/v) as a developing solvent was 0.4.
The Rf value obtained by using chloroform:methanol (20:1 v/v) as a developing solvent was 0.6.
After the development, the spot of DC114-A1 can be detected by bioassay using Bacillus subtilis, by using hot sulfuric acid, or by ultraviolet absorption.
The biological activities of DC114-A1 are described below. The compound DC114-C described above was used for comparison.
(A) Antibacterial activity against various bacteria
The minimum inhibitory concentration (MIC) against the growth of various bacteria is shown in Table 1. The antibacterial activity was determined by the agar dilution method using a medium (pH 7) which comprises 3 g/l Bacto-tryptone (produced by Difco Laboratories), 3 g/l meat extract, 1 g/l yeast extract, 1 g/l glucose and 16 g/l agar.


TABLE 1 ______________________________________ MIC (.mu.g/ml) Bacteria tested DC114-A1 DC114-C ______________________________________ Staphylococcus aureus ATCC 6538P 0.04 0.16 Enterococcus faecium ATCC 10541 0.16 0.16 Bacillus subtilis No. 10707 0.33 0.33 Klebsiella pneumoniae ATCC 10031 5.21 5.21 Escherichia coli ATCC 26 5.21 20.83 Pseudomonas aeruginosa Bin H No. 1 5.21 41.67 Salmonella typhi ATCC 9992 5.21 20.83 Proteus vulgaris ATCC 6897 2.60 5.21 Shigella sonnei ATCC 9290 5.21 20.83 Candida albicans ATCC 10231 5.21 >83.33 ___________

REFERENCES:
Chemical Abstracts, vol. 118, No. 17 (Apr. 26, 1993), 161044n.

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