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I. TAXONOMY, PRODUCTION, ISOLATION AND PRELIMINARY CHARACTERIZATION
HAMAO UMEZAWA, TAKAAKI AOYAGI, TAKAAKI NISHIKIORI, AKIRA OKUYAMA, YUJI ...
1986 Volume 39 Issue 6 Pages
737-744
Published: 1986
Released on J-STAGE: April 19, 2006
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Plipastatins have been isolated as part of a program designed to find inhibitors of porcine pancreatic phospholipase A
2. They were purified from fermentation broth of
Bacillus cereus BMG3O2-fF67 and finally separated into four fractions by reverse phase HPLC. The respective fractions were designated as plipastatins A1, A2, B1 and B2. Plipastatins also inhibited phospholipases C and D.
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II. STRUCTURE OF FATTY ACID RESIDUE AND AMINO ACID SEQUENCE
TAKAAKI NISHIKIORI, HIROSHI NAGANAWA, YASUHIKO MURAOKA, TAKAAKI AOYAGI ...
1986 Volume 39 Issue 6 Pages
745-754
Published: 1986
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Plipastatins, new inhibitors of phospholipase A
2, were produced by a strain classified as
Bacillus cereus BMG302-fF67. The plipastatins are a family of acylated decapeptides which differ from each other by amino acid composition and the nature of the fatty acid side chain. The fatty acids have been shown to be 3(
R)-hydroxyhexadecanoic acid (
n-C
16h
3) and 14(
S)-methyl-3(
R)-hydroxyhexadecanoic acid (
a-C
16h
3) by mass, NMR and optical rotation. Amino acid sequence analysis by secondary ion mass spectrometry and additional physico-chemical evidence indicate that the structures of plipastatinic acids, the lactone-opened peptides are as follows:β-Hydroxy fatty acid→L→Glu→D-Orn→L→Tyr→D-allo→Thr→L-Glu→D-Ala(Val)→L-Pro→L-Gln→D-Tyr→L-Ile-OH.
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III. STRUCTURAL ELUCIDATION OF PLIPASTATINS
TAKAAKI NISHIKIORI, HIROSHI NAGANAWA, YASUHIKO MURAOKA, TAKAAKI AOYAGI ...
1986 Volume 39 Issue 6 Pages
755-761
Published: 1986
Released on J-STAGE: April 19, 2006
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Plipastatins are new inhibitors of phospholipase A2 produced by
Bacillus cereus BMG302-fF67. Structures of the plipastatins have been determined by UV, mass and NMR spectrometries and chemical degradation. The carboxyl group of the
C-terminal L-isoleucine of plipastatinic acid has been shown to form a lactone linkage with the hydroxyl group of Ltyrosine. The total structure of plipastatins has thus been established.
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SUMIO KIYOTO, YOSHIO KAWAI, TAKESHI KAWAKITA, EIKO KING, MASAKUNI OKUH ...
1986 Volume 39 Issue 6 Pages
762-772
Published: 1986
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A complex of the new antitumor antibiotics (WF-1360, WF-1360A, B, C, D, E and F) was produced by Rhizopus sp. No. F-1360. Structural studies of these compounds suggested that they were novel 16-membered-ring lactones having an oxazole ring in their structures. WF-1360 was found to be identical with rhizoxin (1) and WF-1360B, C, E and F were de-termined to be homologues of 1 with structures 2, 3, 4 and 5, respectively. These compounds were cytotoxic when tested on P388 leukemia cells in vitro. WF-1360 was highly active against leukemia L1210 and melanoma B16. They also exhibited potent antifungal activities, but weak antimicrobial activities against some Gram-positive or negative bacteria.
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I. TAXONOMY, ISOLATION AND CHARACTERIZATION
JIRO ITOH, TAKASHI SHOMURA, TADASHI TSUYUKI, JUNKO YOSHIDA, MITSUGU IT ...
1986 Volume 39 Issue 6 Pages
773-779
Published: 1986
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A new antibiotic SF-2330 active against Gram-positive bacteria has been isolated from the culture broth of
Streptomyces sp. SF-2330. The antibiotic was obtained as orange needle crystals and its molecular formula was C
22H
14O
7. This is a new member of the pluramycin group antibiotics.
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II. THE STRUCTURAL ELUCIDATION
JIRO ITOH, TADASHI TSUYUKI, KAYO FUJITA, MASAJI SEZAKI
1986 Volume 39 Issue 6 Pages
780-783
Published: 1986
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The structure of antibiotic SF-2330 has been elucidated to be 11-hydroxy-5-methyl-2-(2, 2'-bioxiran-2-yl)-4
H-anthra[1, 2-
b]pyran-4, 7, 12-trione by spectral analyses. The olefinic side chain at C-2 of α-indomycinone is replaced by a bioxiran-2-yl group in SF-2330.
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I. PRODUCTION, ISOLATION, CHARACTERIZATION AND ANTITUMOR ACTIVITY
MASATAKA KONISHI, KOKO SUGAWARA, FUMIO KOFU, YUJI NISHIYAMA, KOJI TOMI ...
1986 Volume 39 Issue 6 Pages
784-791
Published: 1986
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New antitumor antibiotics, elsamicins A and B, were isolated from the culture broth of an unidentified actinomycete strain J907-21 (ATCC 39417). They are structurally related to chartreusin, containing the common aglycone, chartarin, but contain different sugar moieties. Elsamicin A, the major component, has an amino sugar in the molecule which makes the antibiotic much more water-soluble than chartreusin. Elsamicin A exhibits strong inhibitory activity against various murine tumors including leukemia P388, leukemia L1210, and melanoma B16 but elsamicin B which lacks the amino sugar showed only marginal activity. The potency of elsamicin A was 10-30 times more potent than that of chartreusin in terms of minimum effective dose.
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APPLICATION OF THE MICHEL-MILLER HIGH PERFORMANCE LOW PRESSURE LIQUID CHROMATOGRAPHY SYSTEM
J. H. EGGERT, K. H. MICHEL
1986 Volume 39 Issue 6 Pages
792-799
Published: 1986
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A new antibiotic complex, designated A41030, has been isolated from the fermentation broth of
Streptomyces virginiae. Factors A, B, C, D, E, F and G were separated by an efficient preparative high performance low pressure liquid chromatography system. The apparatus offers economic reversed phase separations on glass columns. The A41030 factors are members of the general class of glycopeptide antibiotics and are active
in vitro and
in vivo vs. Gram-positive bacteria.
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STRUCTURE AND ANTITUMOR ACTIVITY
T. A. SMITKA, R. H. BUNGE, J. H. WILTON, G. C. HOKANSON, J. C. FRENCH, ...
1986 Volume 39 Issue 6 Pages
800-803
Published: 1986
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A new, highly substituted phenazine with antitumor activity was isolated from the culture broth of a
Streptomyces sp. This compound, whose structure was determined by spectroscopic methods and verified by X-ray diffraction analysis, was found to be methyl 6-formyl-4, 7, 9-trihydroxy-8-methyl-1-phenazinecarboxylate.
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E. EICH, C. BECKER, R. SIEBEN, A. MAIDHOF, W. E. G. MÜLLER
1986 Volume 39 Issue 6 Pages
804-812
Published: 1986
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The cytostatic potential of twenty antibiotic agroclavines has been examined in the L5178y mouse lymphoma cell system. Twelve of these compounds are described for the first time. It is shown that the substituent at N-1 of agroclavine is very important whereas the substituent at N-6 is of less influence if it is not hydrogen. Incorporation studies in the presence of 1-propylagroclavine suggest that DNA synthesis in the lymphoma cells is inhibited. The effect on the corresponding [
3H]thymidine incorporation in murine spleen lymphocytes is comparably low. Neither a significant change of mRNA efflux nor of DNA polymerase α and β activities was caused. The mechanism of action seems to be a fundamentally new one for ergoline compounds as interactions with α-adrenoceptors, dopamine and 5-hydroxytryptamine receptors are not involved.
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YOSHITAKE TANAKA, ARIHIRO TAKI, ROKURO MASUMA, SATOSHI OMURA
1986 Volume 39 Issue 6 Pages
813-821
Published: 1986
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A resting cell system was used to study the sites of inhibition by NH
4+ of protylonolide biosynthesis by a blocked mutant, strain 261, of
Streptomyces fradiae. With
14C-labeled succinate or valine as an exogenous substrate, labeled protylonolide formation by high-NH
4+ grown mycelia of strain 261 was lower than by low-NH
4+ grown mycelia. When
14C-labeled palmitate or acetate + labeled propionate + butyrate were used as the substrates, protylonolide production by mycelia grown under the two NH
4+ conditions was nearly at the same rates. It is suggested that the metabolism of succinate and valine to lower fatty acid precursors is subject to NH
4+ regulation, whereas condensation of acid precursors and related steps leading to protylonolide are insensitive to NH
4+ concentration.
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SUSAN E. JENSEN, DONALD W. S. WESTLAKE, RAYMOND J. BOWERS, LEAH LYUBEC ...
1986 Volume 39 Issue 6 Pages
822-826
Published: 1986
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Cell-free enzyme concentrates from
Streptomyces clavuligerus were found to convert phenylacetyl-L-cysteinyl-D-valine (PCV) directly into benzylpenicillin when incubated under reaction conditions which support the activity of isopenicillin N synthetase. The formation of benzylpenicillin was detected both by biological assay and by high performance liquid chromatography. Supplementation of PCV-containing reaction mixtures with cofactors required for ring expansion activity did not result in the production of cephalosporins. Incubation of phenoxyacetyl-L-cysteinyl-D-valine (PoCV) under the same reaction conditions did not result in the formation of penicillin V or any cephalosporin product.
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MASANORI SUGIYAMA, AKINORI TAKEDA, SOON-YOUNG PAIK, OSAMU NIMI, RYOSAK ...
1986 Volume 39 Issue 6 Pages
827-832
Published: 1986
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A blasticidin S-producing actinomycetes,
Streptoverticillium sp. JCM 4673 possesses an enzyme activity which acetylates the drug in the presence of acetyl coenzyme A. The modified drug was biologically inactive when tested against protein synthesis
in vivo and
in vitro. Production of the enzyme which acetylates blasticidin S increases with formation of the antibiotic during cell growth.
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S. ADAM, R. THEN, P. ANGEHRN
1986 Volume 39 Issue 6 Pages
833-838
Published: 1986
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The synthesis and biological activities of a series of non-classical penicillins are described. These compounds were synthesized by treating the pivaloyloxymethyl ester of 6-acetylmethylenepenicillanic acid (Ro 15-1903) with various nucleophiles. They were found to be less active against the β-lactamases from
Proteus vulgaris 1028,
Escherichia coli1024,
Klebsiella pneumoniaeNCTC 418 and
E. coliRTEM than the parent compound. Nevertheless, synergy with ampicillin against whole bacterial cells producing β-lactamases was evident, although the single compounds did not exhibit antibacterial properties. With the compounds
2a and
2b, synergistic interaction with ampicillin could also be demonstrated in mice.
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PIA VILLA, FABRIZIO CORTI, AMALIA GUAITANI, IVAN BARTOSEK, FRANCO CASA ...
1986 Volume 39 Issue 6 Pages
839-845
Published: 1986
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The hepatic clearance and the effects of a new fluorinated macrolide (P-0501A) on the functions of the isolated, perfused rat liver were compared with two known erythromycins-the base and the estolate-after 7 days of treatment (1.36 mmol/kg po daily). The
in vitro metabolism of the antibiotics was induced to different extent but only the base and P-0501A were cleared from the perfusate and the liver faster than in untreated animals. In untreated rats the therapeutically active form of P-0501A was excreted in the bile more than the base and the estolate; after pretreatment, biliary excretion of all erythromycins was nearly double. The content of inactive, complexed cytochrome P-450 was increased only by the base and estolate, with various effects on microsomal activities (some induced,
e.g. aminopyrine demethylation, other reduced,
e.g. pentobarbital clearance). The clearance and biliary excretion of sulphobromophthalein was not affected by treatment with P-0501A or the base, but was significantly reduced by estolate.
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A. VECCHIARELLI, G. VERDUCCI, S. PERITO, P. PUCCETTI, P. MARCONI, F. B ...
1986 Volume 39 Issue 6 Pages
846-855
Published: 1986
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We have recently reported the
in vivo augmentation of resistance to experimental
Candida albicans injection by amphotericin B in mice and have shown that this event is concurrent with the appearance in the spleen of a highly candidacidal cell population reactive
in vitroagainst
51Cr-labeled yeast cells. In the present study we characterize these
in vitro fungicidal effectors as macrophages and describe the conditions of amphotericin B treatment most suitable for inducing candidacidal activity. We also report that macrophages from intact mice can be activated
in vitro to become cytotoxic against
Candida. The possible mechanisms through which the amphotericin B activated macrophages exert their increased anti-
Candida activity are also investigated.
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HANS-PETER FIEDLER, JÜRGEN ROHR, AXEL ZEECK
1986 Volume 39 Issue 6 Pages
856-859
Published: 1986
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TAKAAKI NISHIKIORI, HIROSHI NAGANAWA, YASUHIKO MURAOKA, TAKAAKI AOYAGI ...
1986 Volume 39 Issue 6 Pages
860-863
Published: 1986
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ROSELLA CALVINO, ROBERTA FRUTTERO, ALBERTO GASCO, ANTONELLA MIGLIETTA, ...
1986 Volume 39 Issue 6 Pages
864-868
Published: 1986
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TETSURO SUZUKI, HIROFUMI OKA, AKIRA OKURA, KEN-ICHI ASAHI, NOBUTAKA TA ...
1986 Volume 39 Issue 6 Pages
869-871
Published: 1986
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KAZUNORI OHBA, HIROSHI NAKAYAMA, KAZUO FURIHATA, KEIKO FURIHATA, AKIRA ...
1986 Volume 39 Issue 6 Pages
872-875
Published: 1986
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