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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
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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 IC
50 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
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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 (3
S, 10a
R)-3, 4a-dihydroxy-2, 3, 4, 4a-tetrahydro-2
H-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
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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
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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
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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, MS
n) 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
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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
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A-500359 A, C, D, G and capuramycin inhibited bacterial phospho-
N-acetylmuramyl-pentapeptide-translocase (translocase I: EC 2.7.8.13) with IC
50 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
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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 IC
50 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
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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
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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
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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
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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
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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
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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
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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
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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
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2003 Volume 56 Issue 3 Pages
C1
Published: 2003
Released on J-STAGE: January 27, 2009
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