The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 42 , Issue 2
Showing 1-27 articles out of 27 articles from the selected issue
  • I. FERMENTATION AND ISOLATION
    ROBERT E. SCHWARTZ, ROBERT A. GIACOBBE, JUDITH A. BLAND, RICHARD L. MO ...
    1989 Volume 42 Issue 2 Pages 163-167
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    In screening for new antifungal agents from fungi, a new lipopeptide antifungal agent, L-671, 329, similar to echinocandin B, has been isolated from Zalerion arboricola. Studies indicate that L-671, 329 is produced under both solid and liquid fermentation conditions.
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  • II. STRUCTURE DETERMINATION
    CAROL F. WICHMANN, JERROLD M. LIESCH, ROBERT E. SCHWARTZ
    1989 Volume 42 Issue 2 Pages 168-173
    Published: February 25, 1989
    Released: April 19, 2006
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    Based on spectroscopic data L-671, 329, isolated from a filamentous fungus ATCC 20868, has been assigned the structure 1. The compound is a lipopeptide antifungal agent and a structural analog of echinocandin B.
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  • III. IN VITRO ACTIVITY, TOXICITY AND EFFICACY IN COMPARISON TO ACULEACIN
    ROBERT A. FROMTLING, GEORGE K. ABRUZZO
    1989 Volume 42 Issue 2 Pages 174-178
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    L-671, 329 is a novel, echinocandin-like natural product that possesses potent anti-Candida activity, including activity against Candida parapsilosis. The in vitro MICs of L-671, 329 were comparable to aculeacin against 18 yeasts and three filamentous fungi in an agar dilution assay. L-671, 329 lysed mouse red blood cells (RBCs) at a concentration of 400 μg/ml, but not at 50 or 12.5 μg/ml. Aculeacin lysed RBCs at 400 and 50 μg/ml.
    L-671, 329 significantly prolonged survival of mice infected with Candida albicans (ED50 3.38 mg/kg) following twice-daily intraperitoneal dosing for five consecutive days. The prolongation observed was greater than that seen with aculeacin therapy (ED50 6.44 mg/kg). No acute or chronic toxicities of L-671, 329 or aculeacin (as measured by mortality) were detected at a concentration of 100 mg/kg following intraperitoneal administration (TD50 > 100 mg/kg). Both L-671, 329 and aculeacin eradicated cells of C. albicans from the kidneys of infected mice. L-671, 329 eradicated the yeast at therapeutic concentrations of 12.5 to 100 mg/kg. Aculeacin eradicated yeast cells at therapy concentrations of 25 to 100 mg/kg. L-671, 329 has potential as an anti-Candida compound.
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  • I. TAXONOMY, PRODUCTION, ISOLATION AND BIOLOGICAL PROPERTIES
    MARTHA C. CONE, PAMELA J. SEATON, KAREN A. HALLEY, STEVEN J. GOULD
    1989 Volume 42 Issue 2 Pages 179-188
    Published: February 25, 1989
    Released: April 19, 2006
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    Six new products of Streptomyces murayamaensis sp. nov. Hata et Ohtani, the producer of the kinamycins, were isolated by silica gel column chromatography. The antibacterial activities of the new products, as well as that of dehydrorabelomycin and murayaquinone, previously isolated products of the same organism, were compared to the kinamycins. Three of the products had antibacterial activities similar to the kinamycins, while two others had activity only against Gram-positive bacteria. Dehydrorabelomycin and one other metabolite had no detectable antibacterial activity. The organism was found to be capable of aerial mycelium formation, with sporophores branched at regular intervals bearing square-ended spores with smooth surfaces. The culture contains L, L-diaminopimelic acid in the cell wall (Type I), is highly resistant to lysozyme, and lecithinase- and melanin-positive, suggesting a relationship with the genus Streptoverticillium and the lavendulae group of the genus Streptomyces.
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  • II. STRUCTURES OF PRE-KINAMYCIN, KETO-ANHYDROKINAMYCIN, AND KINAMYCINS E AND F
    PAMELA J. SEATON, STEVEN J. GOULD
    1989 Volume 42 Issue 2 Pages 189-197
    Published: February 25, 1989
    Released: April 19, 2006
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    Four new colored components of Streptomyces murayamaensis sp. nov, Hata et Ohtani, the producer of the kinamycins, have been isolated and their structures determined by a combination of mass spectral, high field NMR and biosynthetic techniques. The first compound with the benz[b]carbazole skeleton in the biosynthetic pathway of kinamycin D has been named "pre-kinamycin" (7). A keto-epoxide kinamycin intermediate has been labeled "keto-anhydrokinamycin" (9), and the 1'-monoacetate of kinamycin has been called kinamycin E (12). Natural production of deacetylkinamycin (13, now labeled kinamycin F) by S. murayamaensis has been confirmed by an isotope trapping experiment. The role of these new intermediates in kinamycin biosynthesis is discussed.
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  • MICHIKO TAKEUCHI, MUTSUO NAKAJIMA, TAKESHI OGITA, MASATOSHI INUKAI, KE ...
    1989 Volume 42 Issue 2 Pages 198-205
    Published: February 25, 1989
    Released: April 19, 2006
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    A new antibiotic, fosfonochlorin, was found in the culture filtrate of four strains of fungi freshly isolated from soil samples. These strains were identified as Fusarium avenaceum, Fusarium oxysporum, Fusarium tricinctum and Talaromyces flavus.
    Fosfonochlorin was a low molecular weight antibiotic (MW 158), soluble in water and methanol, but insoluble in acetone, ethyl acetate and chloroform. It was named after its possession of phosphorus and chlorine atoms, each one molar in its structure. The structure was determined as chloroacetylphosphonic acid mainly by the 1H NMR and mass spectrometric analyses.
    It was moderately active against some species of Gram-negative bacteria and its synergistic effect with glucose-6-phosphate was observed on Staphylococcus aureus and Escherichia coli.
    Spheroplast formation of the susceptible organisms with this antibiotic suggested that it might inhibit their cell wall synthesis.
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  • MICHAEL J. RANGE, JOHN C. RUDDOCK, MICHAEL S. PACEY, WALTER P. CULLEN, ...
    1989 Volume 42 Issue 2 Pages 206-217
    Published: February 25, 1989
    Released: April 19, 2006
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    UK-63, 052 complex, a new group of quinomycin-like antibiotics comprising UK-63, 052 (factor A), UK-63, 598 (factor C), UK-65, 662 (factor B) and several uncharacterised minor components, is produced by a new subspecies of the genus Streptomyces for which the name Streptomyces braegensis Dietz subsp. japonicus, is proposed. The strain, N617-29, is characterised by a negative melanin reaction, grey aerial mycelium, spiral spore chains and smooth or slightly warty spores. Structure determination has identified UK-63, 052, C56H68N10O14S2, UK-63, 598, C53H62N10O14S2 and UK-65, 662, C55H66N10O14S2 as quinaldic acid substituted quinomycins with unusual bridgehead sulfur substitution as shown in Fig. 3.
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  • I. TAXONOMY OF THE PRODUCING STRAIN, FERMENTATION, ISOLATION AND BIOLOGICAL PROPERTIES
    MASAHIRA NAKAGAWA, YUAN-HSUN HSU, AKIRA HIROTA, SHOJI SHIMA, MITSURU N ...
    1989 Volume 42 Issue 2 Pages 218-222
    Published: February 25, 1989
    Released: April 19, 2006
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    A new diterpene antitumor antibiotic, myrocin C, has been isolated from the culture filtrate of a soil fungus, Myrothecium verrucaria strain No. 55. The antibiotic was effective against Gram-positive bacteria, fungi and yeasts, and prolonged the life span of mice bearing Ehrlich ascites carcinoma.
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  • II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
    YUAN-HSUN HSU, AKIRA HIROTA, SHOJI SHIMA, MASAHIRA NAKAGAWA, TOMOHIRO ...
    1989 Volume 42 Issue 2 Pages 223-229
    Published: February 25, 1989
    Released: April 19, 2006
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    The structure of a new antitumor antibiotic, myrocin C, from a strain of Myrothecium vermcaria was characterized as a pentacyclic pimarane diterpene composed of a γ-lactol group and a unique cyclopropane ring on the basis of its physico-chemical properties and spectroscopic data as well as a single-crystal X-ray diffraction analysis of its monoacetyl derivative.
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  • HEINRICH DECKER, CHRISTIANS BORMANN, HANS-PETER FIEDLER, HANS ZÄH ...
    1989 Volume 42 Issue 2 Pages 230-235
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Two new nikkomycins were isolated from the culture broth of Streptomyces tendae Tü 901/PF 53+ -3. The new compounds are the dipeptide nikkomycin pseudo-Z (ψZ) and tripeptide nikkomycin pseudo-J (ψJ), which are analogues to nikkomycins Z and J. Nikkomycins pseudo-Z and pseudo-J have a C-glycosidic linkage between uracil and 5-amino-5-deoxy-D-allo-furanuronic acid, which is comparable to the C-glycosidic bond in pseudouridine. The new CC-nucleoside nikkomycins exhibit a lower biological activity than the CN-nucleoside nikkomycins.
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  • I. FERMENTATION, ISOLATION AND BIOLOGICAL CHARACTERIZATION
    ISAO KANEKO, KATUO KAMOSHIDA, SHUJI TAKAHASHI
    1989 Volume 42 Issue 2 Pages 236-241
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A new potent inhibitor of complement system, named complestatin, was isolated from the mycelium of Streptomyces lavendulae SANK 60477. Complestatin (C61H45N7O15Cl6, MW 1, 325) was a peptide compound having two unusual amino acids, D-(-)-4-hydroxyphenylglycine and D-(-)-3, 5-dichloro-4-hydroxyphenylglycine. This compound inhibited the hemolysis of sensitized sheep erythrocytes (EA) mediated by guinea pig and human complement 50% at concentrations of 0.4 and 0.7 μg/ml, respectively, but did not trypsin and α-chymotrypsin activities at 200 μg/ml. When complestatin was administered intravenously to the sensitized guinea pigs, it strongly inhibited the systemic anaphylactic shock elicited by the antigen probably by blocking generation of anaphylatoxins (C3a and C5a).
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  • SELECTION OF PRODUCER MUTANTS, FERMENTATION, ISOLATION, STRUCTURAL ELUCIDATION AND ANTIBACTERIAL ACTIVITY
    YOSUKE SAWADA, TAKASHI TSUNO, TAKEO MIYAKI, TAKAYUKI NAITO, TOSHIKAZU ...
    1989 Volume 42 Issue 2 Pages 242-253
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Two new 16-membered macrolides, cirramycins F-1 and F-2, were isolated from the culture filtrate of a mutant strain B-1425 of Streptomyces cirratus JTB-3. The antibiotics were also produced by bio-transformation of cirramycin A1 using a blocked mutant strain A-0033. Structures of F-1 and F-2 have been elucidated by spectral interpretation and analysis of acid degradation products. Both involved isomeric modification of a neutral sugar; F-1 contained L-rhodinose, and F-2 L-amicetose. Based on spectral data, cirramycin F-1 and antibiotic A6888C were found to be identical. Cirramycins F-1 and F-2 are active against Gram-positive bacteria, but less active than cirramycin A1.
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  • III. STRUCTURE ELUCIDATION
    R. CIABATTI, J. K. KETTENRING, G. WINTERS, G. TUAN, L. ZERILLI, B. CAV ...
    1989 Volume 42 Issue 2 Pages 254-267
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    By combination of chemical, 1H and 13C NMR, and mass spectrometric studies, the structures of the three components of the antibiotic ramoplanin (A-16686), produced by Actinoplanes sp. ATCC 33076, have been elucidated. All the components have structures formed by a common depsipeptide skeleton carrying a dimannosyl group and are differentiated by the presence of various acylamide moieties, derived from C8, C9 and C10 fatty acids.
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  • IV. COMPLETE SEQUENCE DETERMINATION BY HOMONUCLEAR 2D NMR SPECTROSCOPY
    J. K. KETTENRING, R. CIABATTI, G. WINTERS, G. TAMBORINI, B. CAVALLERI
    1989 Volume 42 Issue 2 Pages 268-275
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    Homonuclear 2D NMR spectroscopy double quantum filter correlation spectroscopy (DQF-COSY), relayed-COSY, nuclear Overhauser enhancement spectroscopy (NOESY), and DQF-relayed-NOESY) allowed the complete determination of the core depsipeptide of antibiotic ramoplanin (A-16686). In particular, the DQF-relayed-NOESY experiments were essential in assigning the single signals close to the diagonal.
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  • II. THE STRUCTURE OF NEOENACTINS NL1 AND NL2 AND STRUCTURE-ACTIVITY RELATIONSHIP
    HIROMASA OKADA, KATSUMI YAMAMOTO, SAYURI TSUTANO, YOSHIO INOUYE, SHOSH ...
    1989 Volume 42 Issue 2 Pages 276-282
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The structures of neoenactins (NEs) NL1 and NL2, novel antimycotic antibiotics produced by Streptoverticillium olivoreticuli in a precursor-oriented fashion, were elucidated by 1H and 13C NMR and mass spectroscopic studies. The structures of both antibiotics are closely related to that of NE-A, the major component of NE congeners, being classified in the group of hydroxamic acid antimycotic antibiotics in which L-serine and a diketo amine form a hydroxamic acid structure.
    To study the role of the carbonyl groups in the biological activities of the hydroxamic acid antimycotic antibiotics, NE-A was modified by reaction with various carbonyl reagents. In terms of antimycotic activity, the derivatives are classified into two distinct groups; the first ones are fairly comparable to but not exceeding and the second ones are less active than NE-A depending on their tendency to revert to NE-A by hydrolysis. In general, the biological activities of the derivatives are inversely proportional to their stabilities to hydrolysis.
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  • KENICHI MOCHIDA, TAKEHIRO OGASA, JUNICHI SHIMADA, TADASHI HIRATA, KIYO ...
    1989 Volume 42 Issue 2 Pages 283-292
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    A series of novel 3-heterocyclothio substituted carbacephems having phenylglycyl side chain have been prepared starting from 3-H carbacephem. The compounds exhibit better chemical stability than the corresponding cephalosporin and strong activity against Gramnegative and Gram-positive organisms including Enterococcus faecalis.
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  • ERIC HUNT, DAVID J. C. KNOWLES, CHRISTINE SHILLINGFORD, JENNIFER M. WI ...
    1989 Volume 42 Issue 2 Pages 293-298
    Published: February 25, 1989
    Released: April 19, 2006
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    A series of 9, 11-cyclic acetal derivatives of (9S)-9-dihydroerythromycin A (4) have been prepared and their antibacterial activities compared to those of erythromycin A and 9-dihydroerythromycin A. Many of the cyclic acetal derivatives showed better antibacterial activity than their parent 4. In particular, the acetaldehyde acetal (9-O, 11-O-ethylidene-9-dihydroerythromycin A) (8b) showed good antibacterial activity in comparison with erythromycin A but was not sufficiently improved in vivo to warrant progression.
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  • V. DERIVATIVES OF URDAMYCIN A
    THOMAS HENKEL, THOMAS CIESIOLKA, JÜRGEN ROHR, AXEL ZEECK
    1989 Volume 42 Issue 2 Pages 299-311
    Published: February 25, 1989
    Released: April 19, 2006
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    Derivatives of the angucycline urdamycin A (1) were prepared in order to study structureactivity relationships in this group of antitumor antibiotics. Derivatives of 1 formed by methanolysis, O-acylation, hydrogenation and treatment with diazomethane were isolated and characterized by their spectroscopic data. Urdamycin G (20) was isolated from Streptomyces fradiae by shortening the fermentation time. The different glycosidation pattern of the aglycone 14 did not lead to significant differences in the biological activity. O-Acylation was shown to enhance the in vitro activity of 1 against stem cells of murine LI210 leukemia depending on the lipophilicity of the molecules. The importance of the 5, 6-double bond of 1 with regard to the antitumor activities is discussed.
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  • KYUICHI NEMOTO, MICHIKO HAYASHI, YUMI SUGAWARA, FUMINORI ABE, TOMOHISA ...
    1989 Volume 42 Issue 2 Pages 312-316
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
    The effect of a novel immunosuppressive agent, deoxyspergualin (DSG), on hematopoiesis in mice was studied with measurements of peripheral blood counts and assays of granulocyte-monocyte colony-forming cells (cfu-C) and spleen colony-forming cells (cfu-S) in bone marrow, during and after successive intraperitoneal administration of DSG. When DSG was administered at a strong immunosuppressive dose of 6.25 mg/kg daily for 15 days, mice developed significantly decreased peripheral blood counts and decreased bone marrow cells (BMC) during administration. After the completion of DSG administration a marked rebound in leukocytosis was observed and BMC returned to normal. In contrast, total cfu-C in the femur significantly increased during the DSG administration, and subsequently returned to normal. Moreover, total cfu-S in the femur were normally sustained in contrast with a decrease of BMC during the DSG administration. These findings suggest that DSG does not show generalized overt cytotoxicity against hematopoietic stem cells and freezes the ability of the stem cell in the proliferation or the differentiation.
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  • II. TAXONOMY OF PRODUCING ORGANISM
    KOJI TOMITA, YUTAKA HOSHINO, YASUKAZU NAKAKITA, SACHIKO UMEZAWA, TAKEO ...
    1989 Volume 42 Issue 2 Pages 317-321
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • DUNCAN M. F. EDWARDS
    1989 Volume 42 Issue 2 Pages 322-324
    Published: February 25, 1989
    Released: April 19, 2006
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  • GABRIELLA H. KELEMEN, ISTVÁN FINANCSEK, MIKLÓS JÁ ...
    1989 Volume 42 Issue 2 Pages 325-328
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • MICHIKO TAKEUCHI, MASATOSHI INUKAI, RYUZO ENOKITA, TOSHIO TAKATSU, YAS ...
    1989 Volume 42 Issue 2 Pages 329-332
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • MITSUNOBU HARA, ISAMI TAKAHASHI, MAYUMI YOSHIDA, Kozo ASANO, ISAO KAWA ...
    1989 Volume 42 Issue 2 Pages 333-335
    Published: February 25, 1989
    Released: April 19, 2006
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  • RODNEY W. RICKARDS
    1989 Volume 42 Issue 2 Pages 336-339
    Published: February 25, 1989
    Released: April 19, 2006
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  • HIROSHI OGAWARA, TETSU AKIYAMA, SHUN-ICHI WATANABE, NORIKI ITO, MASATO ...
    1989 Volume 42 Issue 2 Pages 340-343
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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  • HIROO HOSHINO, JUN-ICHI SEKI, TOMIO TAKEUCHI
    1989 Volume 42 Issue 2 Pages 344-346
    Published: February 25, 1989
    Released: April 19, 2006
    JOURNALS FREE ACCESS
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