The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 56, Issue 3
Displaying 1-18 of 18 articles from this issue
  • I. Taxonomy, Fermentation, Isolation and Biological Activities
    HIROYUKI INOUE, HIROYUKI KUMAGAI, MICHIYO OSONO, MOTOKO MATSUFUJI, TOM ...
    2003 Volume 56 Issue 3 Pages 209-213
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    In the course of screening for inhibitors of osteoclastogenesis, a new substance designated as ICM0201 was isolated from a fermentation broth of Cunninghamella sp. F-1490. ICM0201 inhibited the formation of osteoclasts in mouse bone marrow cells with an IC50 value of 0.78μg/ml and showed weak cytotoxicity against bone marrow cells.
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  • II. Structure Determination and Synthesis
    TETSUYA SOMENO, HIROYUKI INOUE, HIROYUKI KUMAGAI, MASAAKI ISHIZUKA, TO ...
    2003 Volume 56 Issue 3 Pages 214-218
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    ICM0201 (1), a new inhibitor of murine osteoclastogenesis in culture was isolated from a fermentation broth of Cunninghamella sp. F-1490. The structure of ICM0201 was determined to be (3S, 10aR)-3, 4a-dihydroxy-2, 3, 4, 4a-tetrahydro-2H-pyrano[3, 2-b]benzo[e]morpholine-9-carboxylic acid by spectroscopic analyses and chemical studies. The structure of 1 is unique in that the tricycle ring system is composed of aminal and hemiacetal bonds.
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  • I. Isolation of the Strain, Taxonomy and Biological Activites
    LEYRE MALET-CASCÓN, FRANCISCO ROMERO, FERNANDO ESPLIEGO-V&Aacut ...
    2003 Volume 56 Issue 3 Pages 219-225
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    A new compound, IB-00208, has been isolated from the fermentation broth of an actinomycete isolated from a marine environment. The strain was identified as Actinomadura sp. by its chemical and phylogenetic characteristics. The compound shows cytotoxic activity on tumor cell lines and bactericidal activity against Gram-positive bacteria.
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  • I. Taxonomy, Fermentation and Biological Activities
    WENYING LI, JOHN E. LEET, HELEN A. AX, DONALD R. GUSTAVSON, DANIEL M. ...
    2003 Volume 56 Issue 3 Pages 226-231
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    Thiazolyl peptide antibiotics, nocathiacin I, II and III, were identified in a culture of Nocardia sp. WW-12651 (ATCC 202099). They exhibit potent in vitro activity (ng/ml) against a wide spectrum of Gram-positive bacteria, including multiple-drug resistant pathogens such as methicillin-resistant Staphylococcus aureus (MRSA), multi-drug resistant Enterococcus faecium (MREF) and fully penicillin-resistant Streptococcus pneumoniae (PRSP), and demonstrate excellent in vivo efficacy in a systemic Staphylococcus aureus infection mice model.
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  • II. Isolation, Characterization, and Structure Determination
    JOHN E. LEET, WENYING LI, HELEN A. AX, JAMES A. MATSON, STELLA HUANG, ...
    2003 Volume 56 Issue 3 Pages 232-242
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    A new group of thiazolyl peptide antibiotics, the nocathiacins, was isolated from cultured broth of Nocardia sp. The major analogs nocathiacins I-III (1-3) were purified using silica gel and Sephadex LH-20 chromatography techniques. The structures of nocathiacins I-III were determined by spectroscopic (2D-NMR, MSn) methods, and share structural similarities to glycothiohexide-α (4).
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  • I. Taxonomy, Fermentation, Isolation, Physico-chemical Properties and Structure Elucidation of A-500359 A, C, D and G
    YASUNORI MURAMATSU, AKIKO MURAMATSU, TAKASHI OHNUKI, MICHIKO MIYAZAWA ...
    2003 Volume 56 Issue 3 Pages 243-252
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    In the course of our screening for bacterial phospho-N-acetylmuramyl-pentapeptide-translocase (translocase I: EC 2.7.8.13) inhibitors, we found inhibitory activity in the cultured broth of the strain identified as Streptomyces griseus SANK 60196. The strain produced capuramycin and four novel capuramycin derivatives designated as A-500359 A, C, D and G. Purification and structural analysis were performed, and the structures of A-500359 A, C, D and G were elucidated as 6"'-methylcapuramycin, 3'-demethyl-6"'-methylcapuramycin, 2"-deoxy-6"'-methylcapuramycin and 3'-demethylcapuramycin, respectively.
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  • II. Biological Activities of A-500359 A, C, D and G
    YASUNORI MURAMATSU, MICHIKO MIYAZAWA ISHII, MASATOSHI INUKAI
    2003 Volume 56 Issue 3 Pages 253-258
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    A-500359 A, C, D, G and capuramycin inhibited bacterial phospho-N-acetylmuramyl-pentapeptide-translocase (translocase I: EC 2.7.8.13) with IC50 values of 0.017, 0.12, 0.53, 0.14 and 0.018μM, respectively. Consistently, A-500359 A, C and capuramycin inhibited in vitro peptidoglycan biosynthesis. A-500359 A exhibited reversible inhibition, which was mixed type and noncompetitive with respect to UDP-MurNAc-(Nε-Dns)pentapeptide (Ki=0.0079μM) and undecaprenyl-phosphate, respectively. A-500359 A, C, D and G showed antimicrobial activity against Mycobacterium smegmatis. As a single intravenous injection of A-500359 A at a dose of 500mg/kg showed no toxicity in mice, it was suggested that the capuramycin derivatives might become candidates as novel therapeutic agents for various diseases caused by Mycobacteria including tuberculosis.
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  • III. Deaminocaprolactam Derivatives of Capuramycin: A-500359 E, F, H, M-1 and M-2
    YASUNORI MURAMATSU, SHUNICHI MIYAKOSHI, YASUMASA OGAWA, TAKASHI OHNUKI ...
    2003 Volume 56 Issue 3 Pages 259-267
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    Novel derivatives of capuramycin were obtained when 10mM of 2-aminoethyl-L-cysteine (AEC), an inhibitor of aspartokinase, was added to the culture of Streptomyces griseus SANK 60196, the producer of A-500359. They were purified from the culture filtrate and their chemical structures were elucidated as a deaminocaprolactam derivative of capuramycin designated as A-500359 F, A-500359 E, a methyl ester of A-500359 F, and A-500359 H, a 3'-demethyl derivative of A-500359 F. Two other compounds, A-500359 M-1 and A-500359 M-2, were purified from the same medium and their structures were elucidated. A-500359 E, F, H, M-1 and M-2 inhibited bacterial translocase I with an IC50 of 0.027μM, 1.1μM, 0.008μM, 0.058μM and 0.010μM, respectively. A-500359 E, M-1 and M-2 inhibited the growth of mycobacteria as well.
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  • IV. Biosynthesis of A-500359s
    TAKASHI OHNUKI, YASUNORI MURAMATSU, SHUNICHI MIYAKOSHI, TOSHIO TAKATSU ...
    2003 Volume 56 Issue 3 Pages 268-279
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    This report describes the isolation of novel A-500359 analogues from the culture broth of Streptomyces griseus SANK 60196 and 13C-incorporation studies of A-500359 A to reveal the biosynthetic pathway of A-500359 derivatives. As a result, A-500359 M-3 and J were isolated as novel analogues. The former, isolated from a culture broth fed with unnatural amino acids, was a novel amino acid adduct of A-500359, and the latter was found to be a putative precursor of all A-500359 derivatives, on the basis of the structure. Moreover, 13C-incorporation studies revealed the origin of every carbon atom of A-500359 A.
    From these results, it was revealed that the core skeleton of A-500359 was biosynthesized from uridine and phosphoenolpyruvate in the same manner as for polyoxin, a nucleoside antibiotic. Moreover, the uronic acid and aminocaprolactam moiety was derived from hexose and lysine, respectively, and two methyl groups of A-500359 A were derived from methionine.
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  • ALEXANDRE CEVALLOS, ANTONIO GUERRIERO
    2003 Volume 56 Issue 3 Pages 280-288
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    The new naturally occurring erythromycin G (4), formally derived from erythromycin B by hydroxylation of the C-16 methyl group, and 3-O-mycarosylerythronolide B (5), an erythromycin biosynthetic intermediate previously obtained only from microorganisms blocked in erythromycin biosynthesis, were isolated from a concentrate of mother liquors derived from a culture of Saccharopolyspora erythraea. The structure of erythromycin G was defined by spectroscopic data and X-ray crystallographic analysis. Theoretical calculation of 4 has been performed at MM2 level, and the low-energy conformations have been compared with X-ray data: both theoretical and experimental approaches give similar three-dimensional shapes. Antibacterial activity of 4 against both Gram-positive and Gram-negative organisms has been evaluated. A simple method for the isolation of large amounts of erythromycins B (2) and D is provided as well.
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  • MARK J. ZWEIFEL, NANCY J. SNYDER, ROBIN D. G. COOPER, THALIA I. NICAS, ...
    2003 Volume 56 Issue 3 Pages 289-295
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    Glycopeptide antibiotics were synthesized via the PyBOP® mediated condensation of aliphatic, heterocyclic and aromatic amines with the C-terminus of vancomycin, LY264826 (A82846B) and semi-synthetic derivatives of these natural products. Amides of LY264826 and vancomycin demonstrated excellent activity against staphylococci and streptococci as compared to the parent natural product. However, the amides of N-alkylated LY264826 and N-alkylated vancomycin were active against vancomycin-resistant enterococci as well as other Grampositive pathogens such as Staphylococcus aureus, S. haemolyticus, S. epidermidis and Streptococcus pneumoniae.
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  • KARSTEN KROHN, BRIGITTA ELSÄSSER, SÁNDOR ANTUS, KRISZTINA ...
    2003 Volume 56 Issue 3 Pages 296-305
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
    The structure of the antifungal metabolite coniothyriomycin was systematically modified by changing the acids of the open chain imide, modification of the hydrophobicity, variation in the degree of saturation, replacement of carbons by nitrogen or oxygen, and incorporation of the open chain molecule into cyclic arrangements. Structure-activity studies showed that antifungal activity was retained by replacement of phenylacetic acids by benzoic acids in the imide structure but diminished by hydrogenation of the fumaric ester part.
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  • TOSHIO TAKATSU, NOBUO HORIUCHI, MIZUE ISHIKAWA, KYOUKO WANIBUCHI, TAKU ...
    2003 Volume 56 Issue 3 Pages 306-309
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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  • FABRIZIO BELTRAMETTI, AMERIGA LAZZARINI, CRISTINA BRUNATI, ENRICO SELV ...
    2003 Volume 56 Issue 3 Pages 310-313
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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  • VIII. Reactive Oxygen Species Generated by C9-UK-2A, a Derivative of UK-2A, in Rhodotorula mucilaginosa IFO 0001
    KAZUNORI TANI, YOSHINOSUKE USUKI, KEN-ICHI FUJITA, MAKOTO TANIGUCHI
    2003 Volume 56 Issue 3 Pages 314-317
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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  • II. Isolation, Physico-chemical Properties and Structure Determination
    JULIÁN CASTRO RODRÍGUEZ, JOSÉ L. FERNÁNDEZ ...
    2003 Volume 56 Issue 3 Pages 318-321
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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  • KAZUHIKO OTOGURO, HIDEAKI UI, AKI ISHIYAMA, NORIKO ARAI, MIYUKI KOBAYA ...
    2003 Volume 56 Issue 3 Pages 322-324
    Published: March 25, 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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  • 2003 Volume 56 Issue 3 Pages C1
    Published: 2003
    Released on J-STAGE: January 27, 2009
    JOURNAL FREE ACCESS
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