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US 5,332,574 AGranted
Compounds produced by a strain of Streptomyces exfoliatus
AssigneeBristol-Myers Squibb Company
InventorsKoko Sugawara, Koji Tomita, Michael R. Kozlowski, Yosuke Sawada
Life of this patent
Estimating the term…
Abstract
Disclosed are active compounds BU-4726G-A and BU-4726G-B which contain a quinone chromophore and hydroquinone chromophore, respectively. The compounds are produced by fermentation of Streptomyces exfoliatus AA4510. The compounds possess antimicrobial, and K.sub.ATP channel blocking activities.
Claims7
Compound BU-4726G-A having the following characteristics:
- (1) readily soluble in chloroform, ethyl acetate, methanol, acetone and dimethyl sulfoxide;
- essentially insoluble in benzene, n-hexane, and water,
- (2) characteristic UV absorption maxima (UV .lambda..sub.max nm(E)) at 236 nm (524) and 445 nm (83) in neutral and acidic methanol,
- (3) a molecular formula of C.sub.52 H.sub.50 O.sub.20,
- (4) a dimer type structure containing a naphthoquinone chromophore,
- (5) molecular weight as determined by mass spectroscopy (FAB-MS (m/z)) of 995 (M+H).sup.+,
- (6) an optical rotation ([.alpha]sub.D) of 160.+-.10.degree. (concentration 0.5%, methanol),
- (7) infrared spectrum having absorption bands occurring at the following frequencies (IR.nu..sup.KBr.sub.max cm.sup.-1):
- 3450, 2980, 1780, 1760, 1700, 1670, 1640, and 1320,
- (8) positive responses to iodine vapor, ferric chloride, ammonium molybdate-sulfuric acid;
- negative responses to ninhydrin, Ehrlich and anthrone reagents,
- (9) melting point of greater than 200.degree. C. (decomposition), and
- (10) elemental analysis:
- Calculated for C.sub.52 H.sub.50 O.sub.20.H.sub.2 O:C;
- 61.66, H;
- 5.17,
- Found:
- C;
- 61.42, H;
- 5.10.
17 more elements
Compound BU-4726G-B having the following characteristics:
- (1) readily soluble in chloroform, ethyl acetate, methanol, acetone and dimethyl sulfoxide;
- essentially insoluble in benzene, n-hexane, and water,
- (2) characteristic UV absorption maxima (UV .lambda..sub.max nm(E)) at 279 nm (707) and 426 nm (304) in neutral and acidic methanol,
- (3) a molecular formula of C.sub.52 H.sub.54 O.sub.20,
- (4) a dimer type structure containing a naphtohydroquinone chromophore,
- (5) molecular weight as determined by mass spectroscopy (FAB-MS (m/z)) of 999 (M+H).sup.+,
- (6) an optical rotation ([.alpha]sub.D) of -39.degree..+-.5.degree. (concentration 0.25%, methanol),
- (7) infrared spectrum having absorption bands occurring at the following frequencies (IR .nu..sup.KBr.sub.max cm.sup.-1):
- 3400, 2980, 1740, 1630, 1400, and 1330,
- (8) positive responses to iodine vapor, ferric chloride, ammonium molybdate-sulfuric acid;
- negative responses to ninhydrin, Ehrlich and anthrone reagents,
- (9) melting point of greater than 200.degree. C. (decomposition), and
- (10) elemental analysis:
- Calculated for C.sub.52 H.sub.54 O.sub.20.H.sub.2 O:C;
- 61.41, H;
- 5.55.
- Found:
- C;
- 61.35, H;
- 5.27.
17 more elements
Dependencies are inferred from the claim text.