KD16-U1, a new metabolite of Streptomyces: isolation and structural studies.
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Acetylation↗
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A new route to the synthesis of cyclitol derivatives.
Three cyclitol derivatives, 2,4/3-triacetoxycyclohexanone diethyl dithioketal (XVIII), and 2,3,4-tri-O-acetyl-1-O-ethyl-2,4/1,3-cyclohexanetetrol (XXA) and 2,3,4-tri-O-acetyl-1-O-ethyl-1,2,4/3-cyclohexanetetrol (XXB), have been synthesized via the cyclisation of 2,3,4-tri-O-acetyl-5,6-dideoxy-D-xylo-hex-5-enose diethyl dithioacetal (XIV) and the cyclisation of 2,3,4-tri-O-acetyl-5,6-dideoxy-D-xylo-hex-5-enose diethyl acetal (XV) under ultraviolet or direct sunlight, in aqueous acetone.
Anti-Bacterial Agents↗
Mechanism of action of 2-crotonyloxymethyl-4,5,6-trihydroxycyclohex-2-enone, a SH inhibitory antitumor antibiotic, and its effect on drug-resistant neoplastic cells.
An inhibitor of alkaline phosphodiesterase was isolated from a soil Streptomyces. The agent was identified with 2-crotonyloxymethyl-4,5,6-trihydroxycylohex-2-enone (COTC) by UV, IR, 1H HMR and 13C NMR spectrometry. The mechanism of tumor-inhibitory action of COTC was studied with murine lymphoblastma L5178Y cells. COTC blocked alkaline phosphodiesterase; IC 50 was 60 micrograms/ml by the method employed. The growth of L5178Y cells was inhibited by COTC; IC50 was 4.4 micrograms/ml. DNA biosynthesis was preferentially prevented by COTC over RNA and protein syntheses; IC50 of DNA synthesis was 7 or approximately 25 micrograms/ml. COTC significantly inhibited DNA polymerase alpha even in the presence of dithiothreitol. The mitosis was markedly blocked by COTC; complete inhibition was observed at a drug concentration of 20 microgram/ml. Adriamycin-, aclarubicin- and bleomycin-resisant cell subline showed collateral sensitivity to COTC. COTC and aclarubicin exhibited synergistic activity on aclarubicin-resistant cells, but not on the parental cells. COTC increased uptake of [3H]adriamycin or blocked the drug efflux in the resistance cells, but not in the parental cells. The effects of COTC on macromolecular syntheses, mitosis and membrane functions may be attributed to the interaction with the sulfhydryl group of various enzymes. Although COTC is multifunctional drug, the inhibition of DNA polymerase alpha and a certain mitotic process seems to be related to the lethal action.
Animals↗
SQ 30,957, a new antibiotic produced by Penicillium funiculosum. Taxonomy, fermentation, isolation, structure determination, synthesis and antibacterial activity.
A new antibiotic, SQ 30,957, 4-diazo-3-methoxy-2,5-cyclohexadien-1-one, has been isolated from fermentation broths of Penicillium funiculosum. The structure (1) was deduced from its spectroscopic properties and its degradation reaction. SQ 30,957 has excellent activity against anaerobic bacteria such as Clostridium and Bacteroides and has moderate activity against aerobic bacteria. The compound has an LD50 of less than 17 mg/kg in mice by intraperitoneal administration.
Animals↗
AB5046A and B, novel chlorosis-inducing substances from Nodulisporium sp.
Novel chlorosis-inducing substances, AB5046A and B, were isolated from the culture broth of a fungal strain. The producing organism, designated AB5046, was identified as a member of Nodulisporium. AB5046A and B were purified by extraction with EtOAc and silica gel chromatography. The structure of AB5046A and B were determined to be 2-butyryl-3,5-dihydroxy-cyclohex-2-ene-1-one and 2-acetyl-3,5-dihydroxy-cyclohex-2-ene-1-one, respectively, by spectroscopic analyses. AB5046A and B induced chlorosis against Japanese barnyard millet in vitro. The chlorosis activity of these compounds was stronger against monocotyledons than dicotyledons.
Animals↗
Lachnumon and lachnumol a, new metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. I. Producing organism, fermentation, isolation and biological activities.
Several chlorinated metabolites with nematicidal, antimicrobial, and cytotoxic activities were isolated from submerged cultures of the ascomycete Lachnum papyraceum. Three compounds were identified as (+)-mycorrhizin A (3), (+)-chloromycorrhizin A (4) and (+)-dechloromycorrhizin A (5). The occurrence of 5 as a natural product is new. Two compounds, lachnumon (1) and lachnumol A (2), were found to be new fungal metabolites with cytotoxic, nematicidal and antimicrobial activities.
Animals↗
Lachnumon and lachnumol a, new metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. II. Structural elucidation.
The structures of two new biologically active chlorinated metabolites isolated from submerged cultures of the ascomycete Lachnum papyraceum have been elucidated by NMR and mass spectroscopy. The compounds, lachnumon (1) and lachnumol A (2), which structurally are related with mycorrhizin A that also is produced by the fungus, contain an unusual chlorinated epoxide group.
Antifungal Agents↗
Metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. V. Production, isolation and biological activities of bromine-containing mycorrhizin and lachnumon derivatives and four additional new bioactive metabolites.
Eight novel bioactive metabolites were isolated from submerged cultures of the ascomycete Lachnum papyraceum (Karst.) Karst, when CaBr2 was added to the cultures after the onset of secondary metabolism. Four of these metabolites (16 to 19) are bromo analogues of mycorrhizin A and lachnumon, while (l'Z)-dechloromycorrhizin A (12) and the papyracons A (13), B (14), and C (15) are non-halogenated compounds structurally related to the mycorrhizins. All compounds exhibited antimicrobial, cytotoxic, nematicidal and phytotoxic activities. The brominated mycorrhizins and lachnumons were found to be slightly less active than the chlorine-containing compounds. All mycorrhizin derivatives were mutagenic in the Ames test, suggesting DNA-alkylating properties.
Animals↗
New metabolites with nematicidal and antimicrobial activities from the ascomycete Lachnum papyraceum (Karst.) Karst. VII. Structure determination of brominated lachnumon and mycorrhizin A derivatives.
The structure determination of lachnumon B1 (16) and lachnumon B2 (17), brominated derivatives of lachnumon (1), as well as mycorrhizin B1 (18) and mycorrhizin B2 (19), brominated derivatives of mycorrhizin A (3), is described. The compounds, which exhibit similar antimicrobial and nematicidal activity as their chlorinated analogues, were isolated from extracts of cultures of the ascomycete Lachnum papyraceum to which CaBr2 had been added. The structures were elucidated by spectroscopic methods.
Anti-Bacterial Agents↗
Darlucins A and B, new isocyanide antibiotics from Sphaerellopsis filum (Darluca filum).
Two new xanthocillin type antibiotics, darlucin A (1) and B (2), were isolated from fermentations of Sphaerellopsis filum (Darluca filum). Their structures were established by spectroscopic methods. The darlucins are the first known compounds with a 1,2-diisocyanoalkene moiety. Both compounds exhibited antibacterial, antifungal and weak cytotoxic activities.
Animals↗
Cremeomycin, a novel cytotoxic antibiotic from Streptomyces cremeus. Structure elucidation and biological activity.
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Animals↗
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. I. Taxonomy of producing strain, fermentation and isolation.
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme (ICE) inhibitors, were isolated from the culture broths of Streptomyces sp. E-1511 and E-1625. EI-1511-3, -5 and EI-1625-2 selectively inhibited the recombinant human ICE activity with IC50 values of 0.09, 0.38 and 0.2 microM, respectively. Taxonomy, fermentation of the producing strain and isolation of EI-1511-3, -5 and EI-1625-2 are described.
Amides↗
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. II. Structure determination.
The structures of three novel interleukin-1 beta converting enzyme inhibitors, EI-1511-3, -5 and EI-1625-2 were determined by spectroscopic methods. Their absolute configurations were also determined by analyses of the CD spectra of the inhibitors and their oxidation products with chromium trioxide.
Amides↗
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme inhibitors produced by Streptomyces sp. E-1511 and E-1625. III. Biochemical properties of EI-1511-3, -5 and EI-1625-2.
EI-1511-3, -5 and EI-1625-2, novel interleukin-1 beta converting enzyme (ICE) inhibitors from the culture broths of Streptomyces sp. selectively inhibited the recombinant human ICE activity with IC50 values of 0.09, 0.38 and 0.2 microM, respectively, without inhibiting elastase and cathepsin B. Manumycin G, ent-alisamycin, U-56,407, and manumycin A and B isolated simultaneously from the same strains also inhibited ICE. EI-1511-3, -5 and EI-1625-2 also inhibited mature interleukin-1 beta secretion from THP-1 cells with IC50 values of 5.4, 3.6 and 2.2 microM, respectively. In this article, biological properties of EI-1511-3, -5 and EI-1625-2 and, in addition, properties of manumycin-related compound are described.
Amides↗
TMC-1 A, B, C and D, new antibiotics of the manumycin group produced by Streptomyces sp. Taxonomy, production, isolation, physico-chemical properties, structure elucidation and biological properties.
Four new antitumor antibiotics, TMC-1 A, B, C and D were isolated from a fermentation broth of Streptomyces sp. A-230. Spectroscopic studies have shown that TMC-1 A to D were new members of the manumycin class of antibiotics. These antibiotics showed cytotoxic activities against various tumor cell lines in vitro.
Animals↗
Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. I. Taxonomy, fermentation, isolation and biological activities.
Selective growth inhibition against IL-6 dependent cells was detected in fermentation extracts of a fungal strain FO-4649 which was characterized as Sporothrix species. An active metabolite (1) termed chlovalicin was isolated together with ovalicin and two other ovalicin derivatives (compounds 3 and 4). Chlovalicin, a ovalicin derivative with a chlorinated methylene moiety at the C-1 position of the cyclohexane ring, dose-dependently inhibited the growth of IL-6 dependent MH60 cells (IC50, 7.5 microM) in the presence of 0.2 U/ml IL-6 and, to a lesser extent, the growth of B16 melanoma cells (IC50, 38 microM). Among the other three compounds, only ovalicin showed inhibitory activity (IC50, 27 microM) against MH60 cells. These four compounds did not show any antimicrobial activity at a concentration of 1000 micrograms/ml.
Animals↗
Chlovalicin, a new cytocidal antibiotic produced by Sporothrix sp. FO-4649. II. Physicochemical properties and structural elucidation.
A new growth inhibitor of IL-6 responsive MH60 cells, chlovalicin (MW; 332, C16H25O5Cl), was found in cultures of Sporothrix sp. FO-4649, together with a known sesquiterpene, ovalicin. The structure of chlovalicin was elucidated by spectroscopic methods. Chlovalicin possesses a chlorinated methylene moiety at the C-1 position, and it corresponds to halogenated products derived from the epoxide ring attached to the C-1 position of ovalicin. The absolute configuration of chlovalicin was clarified as 1S, 2R, 3S, 1'S, 2'R by chemical transformation from ovalicin.
Anti-Bacterial Agents↗
Mer-f3, 12-hydroxy-ovalicin, produced by Metarrhizium sp. f3.
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Antibiotics, Antineoplastic↗