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TAXONOMY, FERMENTATION, ISOLATION, STRUCTURE ELUCIDATION AND BIOLOGICAL PROPERTIES
SHINICHIRO KATO, KAZUTOSHI SHINDO, YUJI YAMAGISHI, MICHIKO MATSUOKA, H ...
1993 Volume 46 Issue 10 Pages
1485-1493
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Phenazoviridin is a newly discovered free radical scavenger from microorganisms. It was isolated from the culture of
Streptomyces sp. HR04. The structure of phenazoviridin was determined as 6-(3-methyl-2-butenyl)phenazine-1-carboxylic acid 6-deoxy-α-L-talopyranose ester on the basis of its spectroscopic and physico-chemical properties. The novel substance showed strong inhibitory activity against lipid peroxidation in rat brain homogenate and exhibited antihypoxic activity in mice.
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TAKAFUMI KOHAMA, HIROKO MIYAOKA, AKIO TORIKATA, MASATOSHI INUKAI, ISAO ...
1993 Volume 46 Issue 10 Pages
1494-1502
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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A new screening method for inducers of colony-stimulating factors (CSFs) was established using KM-102, a human bone marrow stromal cell line as the producer. In this method, the assay system which uses CSF dependent cell lines is combined with the CSF production system. Interleukin-1 (IL-1), which is known to upregulate CSF production in many cell populations, was used as a positive control for production of granulocyte CSF (G-CSF) and granulocyte-macrophage CSF (GM-CSF). Induction in the positive controls was clearly detected within 24 hours. Activators of protein kinase C (PKC), protein phosphatase inhibitors and lipopolysaccharide (LPS) were positive in this assay system, but muramyl dipeptide (MDP) and Bestatin which are known macrophage activators, were negative.
Inducers of CSFs were successfully detected using this assay method. Among 1, 600 microbial strains tested, 2 actinomycete strains were found to produce active substances. One strain produces teleocidin-A, a strong activator of PKC, and the other strain produces a mixture of active compounds including three novel compounds. These three compounds do not induce terminal differentiation of HL-60 cells, suggesting that they are not teleocidin-like substances and form a new class of CSF inducers.
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I. TAXONOMY, FERMENTATION AND BIOLOGICAL PROPERTIES
TAKAFUMI KOHAMA, RYUZO ENOKITA, TAKAO OKAZAKI, HIROKO MIYAOKA, AKIO TO ...
1993 Volume 46 Issue 10 Pages
1503-1511
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Three metabolites were isolated from the culture broth of an actinomycete strain identified as
Streptomyces platensis SANK 60191, that induce the production of colony-stimulating factors (CSFs) by stromal cell line KM-102 at ED
50 concentrations from 40 to 200ng/ml. The compounds induced quantities of granulocyte CSF (G-CSF) and granulocyte-macrophage CSF (GM-CSF) comparable to those induced by interleukin-1, a strong CSF inducer. These metabolites were called leustroducsins (A, B and C) and were later found to be structurally related to phoslactomycins. This is the first report of CSF inducing activity by members of the phoslactomycin class.
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II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE DETERMINATION
TAKAFUMI KOHAMA, TAKEMICHI NAKAMURA, TAKESHI KINOSHITA, ISAO KANEKO, A ...
1993 Volume 46 Issue 10 Pages
1512-1519
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Leustroducsins (LSNs) A, B and C, novel inducers of colony-stimulating factors (CSFs), were isolated from culture broth of
Streptomyces platensis SANK 60191 mainly by ethyl acetate extraction and preparative reverse-phase HPLC. The molecular weights and molecular formulae of LSNs A, B and C are 641: C
32H
52O
10NP, 669: C
34H
56O
10NP and 669: C
34H
56O
10NP, respectively. The structure elucidation revealed that they belong to the phoslactomycin group antibiotics, and their structures contain an α, β-unsaturated δ-lactone, an amino group, a phosphate ester and a cyclohexane ring moiety. The structures differ only at the substituent bound to the cyclohexane ring.
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I. TAXONOMY, FERMENTATION, ISOLATION AND BIOLOGICAL CHARACTERISTICS
KANKI KOMIYAMA, SATOSHI TAKAMATSU, YOKO TAKAHASHI, MAYUMI SHINOSE, MAS ...
1993 Volume 46 Issue 10 Pages
1520-1525
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Melanogenesis inhibitors, OH-3984 K1 and K2 were isolated from fermentation broth of
Streptomyces sp. OH-3984. OH-3984 K1 and K2 inhibited the melanogenesis of B16 melanoma cells at concentrations of 7.5 and 3.8 μg/ml, respectively, whereas inhibition of tyrosinase activity has not been observed. The microbial metabolites showed no antimicrobiological activities against Gram-positive and Gram-negative bacteria, fungi or yeast at a concentration of 1, 000 μg/ml.
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II. PHYSICO-CHEMICAL PROPERTIES AND STRUCTURAL ELUCIDATION
SATOSHI TAKAMATSU, MUN-CHUAL RHO, MASAHIKO HAYASHI, KANKI KOMIYAMA, HA ...
1993 Volume 46 Issue 10 Pages
1526-1529
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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New melanin synthesis inhibitors, OH-3984 K1 and K2, were isolated from the fermentation broth of
Streptomyces sp. OH-3984, and their structures were elucidated by spectroscopic methods and by chemical transformations. OH-3984 K1 (M.W.: 306; C
18H
26O
4) and K2 (M.W.: 308; C
18H
28O
4) have unique γ-lactone rings, both of which correspond to oxidative products derived from C
1-O
14 cleavage of the 14-membered lactone group.
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I. TAXONOMY OF THE PRODUCING ORGANISM, FERMENTATION, HPLC ANALYSIS AND BIOLOGICAL ACTIVITIES
NAOKI ABE, YASUKAZU NAKAKITA, TAKEHIKO NAKAMURA, NOBUYASU ENOKI, HIDEA ...
1993 Volume 46 Issue 10 Pages
1530-1535
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Streptomyces sp. HP530 was found to produce novel antitumor antibiotics, saptomycins, closely related to the pluramycin-group and was further found to mutate frequently. The natural mutant produced several new saptomycins as determined by HPLC analyses. We isolated saptomycins A, B, C
1, C
2 and F from the parent strain and saptomycins D, E, G and H from the mutant. The saptomycins showed antimicrobial activities and potent antitumor activities against human or murine tumor cell lines
in vitro and against Meth A fibrosarcoma
in vivo. In particular, saptomycin D was most effective component
in vivo of all saptomycins.
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II. ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND STRUCTURE ELUCIDATION
NAOKI ABE, NOBUYASU ENOKI, YASUKAZU NAKAKITA, HIDEAKI UCHIDA, TAKEHIKO ...
1993 Volume 46 Issue 10 Pages
1536-1549
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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A complex of novel antitumor antibiotics related to the pluramycin-group was isolated from the fermentation of actinomycete, named
Streptomyces sp. HP530. The producing strain mutated frequently. The products isolated from the parent strain were designated saptomycins A, B, C
1, C
2 and F, while those of the mutant were named saptomycins D, E, G and H. These structures were elucidated by several NMR spectral analyses and other spectroscopic experiments.
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CORNEL MARTIN, LUKAS OBERER, TOMIO INO, WILFRIED A. KÖNIG, MICHAE ...
1993 Volume 46 Issue 10 Pages
1550-1556
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Four depsipeptides (peptide lactones), called cyanopeptolins A, B, C and D, have been isolated from the cyanobacterium
Microcystis sp. PCC 7806. They possess identical structures consisting of cyclic L-glutamic acid-γ-aldehyde, L-leucine,
N-methyl-phenylalanine, L-valine, L-threonine, L-aspartic acid, hexanoic acid and a variable basic amino acid. This variable amino acid can be L-arginine (cyanopeptolin A), L-lysine (cyanopeptolin B),
Nε-methyl-L-lysine (cyanopeptolin C) and
Nε,
Nε-dimethyl-L-lysine (cyanopeptolin D), respectively. The L-glutamic acid-γ-aldehyde and the amino group of L-leucine form an unusual 3-amino-6-hydroxy-2-oxo-1-piperidine system. L-Threonine is connected to L-valine
via its hydroxy-group forming an ester bonding. The hexanoic acid residue is attached to the
N-terminal aspartic acid residue which is not a part of the ring structure. The isolation procedure of the four cyanopeptolins as well as structure elucidation are described. Amino acid analysis, GC/MS analysis, FAB-MS and several NMR techniques were used to reveal the structures.
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I. TAXONOMY, FERMENTATION, ISOLATION, PHYSICO-CHEMICAL PROPERTIES AND BIOLOGICAL ACTIVITY
YOICHI HAYAKAWA, MICHIKO MATSUOKA, KAZUO SHIN-YA, HARUO SETO
1993 Volume 46 Issue 10 Pages
1557-1562
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Three novel macrolide antibiotics, quinolidomicins A
1, A
2 and B
1, were isolated from the fermentation broth of
Micromonospora sp. JY16. Quinolidomicin A
1 inhibited the growth of various tumor cells including multidrug-resistant cells. Quinolidomicin B
1 was similarly cytotoxic, while quinolidomicin A
2 was inactive against these tumor cells.
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II. STRUCTURE ELUCIDATION
YOICHI HAYAKAWA, KAZUO SHIN-YA, KAZUO FURIHATA, HARUO SETO
1993 Volume 46 Issue 10 Pages
1563-1569
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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The structures of novel macrolide antibiotics, quinolidomicins A
1, A
2 and B
1, were elucidated as shown in Fig. 1 by NMR spectral analysis including a variety of two-dimensional techniques. The quinolidomicins possess a novel 60-membered macrolide ring, which is to our knowledge the largest among natural products.
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JIN-ZHONG XIAO, SHIGENORI KUMAZAWA, HIROFUMI TOMITA, NOBUJI YOSHIKAWA, ...
1993 Volume 46 Issue 10 Pages
1570-1574
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Novel antibiotic, rousselianone A, was produced by fermentation of
Phaeosphaeria rousseliana L2144. Rousselianone A was characterized as a new derivative of phenalenone. The antibiotic showed no antimicrobial activity
in vitro, but exhibited
in vivo antifungal activity against plant diseases with a relatively broad spectrum.
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TATSUYA ITOH, KENJI ISHII, TOMOHIRO IRIKURA, YOSHIO UENO, ASATO KOJIMA ...
1993 Volume 46 Issue 10 Pages
1575-1581
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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A modified mixed lymphocyte reaction (MLR) assay was developed to screen immunosuppressive agents. In the MLR, irradiation of splenocytes with UV light was employed for the preparation of stimulator cells, and the highest response was observed with the combination of splenocytes of C3H/He mice as a stimulator and those of 57BL/6 as a responder. The blastogenesis of the responder cells was quantified by a colorimetric method using MTT in 96-well microculture plates. For screening immunosuppressive substances, the MLR in combination with a cytotoxicity test can distinguish immunosuppressors from cytotoxic agents. The applications of this assay system to extracts of fungal culture was also described.
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2. ISOLATION OF DIDEMETHYLALLOSAMIDIN, AND CONVERSION EXPERIMENTS OF 14C-LABELED DEMETHYLALLOSAMIDIN, DIDEMETHYLALLOSAMIDIN AND THEIR RELATED COMPOUNDS
ZE-YANG ZHOU, SHOHEI SAKUDA, MASAYOSHI KINOSHITA, YASUHIRO YAMADA
1993 Volume 46 Issue 10 Pages
1582-1588
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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A new allosamidin analog, termed didemethylallosamidin (
3), was isolated from the mycelia of
Streptomyces sp. AJ 9463 which is a producer of allosamidin (
1) and demethylallosamidin (
2).
14C-Labeled
1,
2 and
3 as well as their related compounds,
4,
5, and
6, were prepared to investigate the biosynthesis of
1. Conversion experiments with the labeled allosamidins revealed that
2 was a precursor of
1, but
3 was not incorporated. This suggests that the first
N-methyl group is introduced before the cyclization of the aminooxazoline ring during the biosynthesis of
1. Although none of the compounds
4,
5, and
6 were converted to
1, the production of
1 was inhibited by the addition of
4.
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TAMOTSU FURUMAI, HARUAKI YAMAMOTO, YUKIO NARITA, TOSHIFUMI HASEGAWA, S ...
1993 Volume 46 Issue 10 Pages
1589-1597
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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In a screen of pradimicin-nonproducing mutants derived from
Actinomadura verrucosospora subsp.
neohibisca R103-3, we found a strain capable of producing 11-hydroxyl analogs of pradimicins A and FA-1, designated pradimicins H and FH, respectively. Feeding of pradimicins H and FH to growing cultures of an actinomycete strain AA3798 produced 11-
O-L-xylosylpradimicins H and FH, respectively. These 11-
O-L-xylosylpradimicins had a broad spectrum of antifungal activity and demonstrated
in vivo efficacies against
Candida albicans in mice.
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JAN PAWLAK, PAWEL SOWINSKI, EDWARD BOROWSKI, PIERLUIGI GARIBOLDI
1993 Volume 46 Issue 10 Pages
1598-1604
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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The stereostructure of the heptaene macrolide antibiotic candidin was established on the basis of NMR studies:
13C, DQF-COSY, ROESY and C, H-COSY experiments. The absolute configuration of the candidin chiral centers were assigned as 3
R, 5
S, 10
R, 11
R, 13
R, 15
S, 16
R, 17
S, 19
S, 34
S, 35
R, 36
R and 37
S.
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NAOKO MORISAKI, SHIGEO IWASAKI, KATSUKIYO YAZAWA, YUZURU MIKAMI, AKIO ...
1993 Volume 46 Issue 10 Pages
1605-1610
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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Rifampicin (
1) was converted into four inactivated products by pathogenic
Nocardia, RIP-1 and RIP-2 by
N. brasiliensis and RIP-3 and RIP-4 by
N. otitidiscaviarum. MS and NMR analysis showed the compounds to be 3-formyl-23-[
O-(β-D-glucopyranosyl)]rifamycin SV (
2), 23-[
O-(β-Dglucopyranosyl)]rifampicin (
3), 21-(
O-phosphoryl)rifampicin (
4) and 3-formyl-21-(
0-phosphoryl)-rifamycin SV (
5), respectively.
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HIDEAKI UCHIDA, YASUKAZU NAKAKITA, NOBUYASU ENOKI, NAOKI ABE, TAKEHIKO ...
1993 Volume 46 Issue 10 Pages
1611-1615
Published: October 25, 1993
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KIMIE KOBINATA, HIROYUKI KOSHINO, TAKUJI KUDO, KIYOSHI ISONO, HIROYUKI ...
1993 Volume 46 Issue 10 Pages
1616-1618
Published: October 25, 1993
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HIROYUKI KOSHINO, KIMIE KOBINATA, KIYOSHI ISONO, HIROYUKI OSADA
1993 Volume 46 Issue 10 Pages
1619-1621
Published: October 25, 1993
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REI KANETO, HIROYUKI CHIBA, KAZUYUKI DOBASHI, IKUO KOJIMA, KAZUYA SAKA ...
1993 Volume 46 Issue 10 Pages
1622-1624
Published: October 25, 1993
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II. MINOR COMPONENTS BELONGING TO THE OBSCUROLIDE B TO D SERIES
MICHAEL RITZAU, SIEGRID PHILIPPS, AXEL ZEECK, HUBERT HOFF, HANS ZÄ ...
1993 Volume 46 Issue 10 Pages
1625-1628
Published: October 25, 1993
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YOSHIHIRO SUMITA, YOKO EGUCHI, MASATOMO FUKASAWA, TAKAO OKUDA, HIROSHI ...
1993 Volume 46 Issue 10 Pages
1629-1632
Published: October 25, 1993
Released on J-STAGE: April 19, 2006
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