Metabolic products of microorganisms. 244. Colabomycins, new antibiotics of the manumycin group from Streptomyces griseoflavus. I. Isolation, characterization and biological properties.

Grote, R.; Zeeck, Axel; Drautz, Hannelore; Zähner, Hans

doi:10.7164/antibiotics.41.1178

Cited by 33 publications

(13 citation statements)

References 10 publications

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“…9 All of these compounds have the same E,E,E-trienyl lower side chains terminating in a 2-amino-3-hydroxycyclopentenone derived amide. U-56407 (13) 10 is reported to possess a Z,Z,E-trienyl lower side chain (although this stereochemical assignment must be treated with caution 5b ) whereas colabomycin (14) 11 is a higher vinylogue, nisamycin (15) 12 lacks the terminal amide linkage, and U-62162 (16) 13 has a saturated lower side chain. The upper side chains of the family members are more distinctive but all of these compounds are based on the epoxyaminocyclohexenone nucleus which is also found in the anti-tumour antibiotic LL-C10037a (17), 14 and the broad spectrum antibiotic MM-14201 (18).…”

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confidence: 99%

The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

et al. 1998

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Versatile synthetic routes are described for the preparation of a range of epoxyquinol and epoxyquinone analogues of the antitumour antibiotic manumycin A lacking the lower side chain, and these procedures have also been applied to prepare the bioactive natural product LL-C10037a. The extension of this methodology to provide a general synthetic route to the manumycin family of antibiotics is discussed and exemplified by the first total synthesis of alisamycin and ent-alisamycin. This route includes the novel, stereoselective organometallic addition of the Corey-Wollenberg reagent (E-2-tributylstannylethenyllithium) to the manumycin nucleus and palladium catalysed Stille coupling technology for the introduction of the polyunsaturated 2-amino-3hydroxycyclopentenone derived amide. Similar methodology has also been employed to complete the first total synthesis of the antibiotic nisamycin.

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The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

et al. 1998

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“…The main compound produced by the strain was identified as a new manumycin‐type compound: colabomycin E. At least three other structurally related congeners, including the already known colabomycin A,23, 36 accompanied the major product. The lower carbon chains of colabomycin E and of all its congeners are tetraenes.…”

Section: Discussionmentioning

confidence: 99%

Biosynthesis of Colabomycin E, a New Manumycin‐Family Metabolite, Involves an Unusual Chain‐Length Factor

et al. 2014

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Colabomycin E is a new member of the manumycin-type metabolites produced by the strain Streptomyces aureus SOK1/5-04 and identified by genetic screening from a library of streptomycete strains. The structures of colabomycin E and accompanying congeners were resolved. The entire biosynthetic gene cluster was cloned and expressed in Streptomyces lividans. Bioinformatic analysis and mutagenic studies identified components of the biosynthetic pathway that are involved in the formation of both polyketide chains. Recombinant polyketide synthases (PKSs) assembled from the components of colabomycin E and asukamycin biosynthetic routes catalyzing the biosynthesis of "lower" carbon chains were constructed and expressed in S. aureus SOK1/5-04 ΔcolC11-14 deletion mutant. Analysis of the metabolites produced by recombinant strains provided evidence that in both biosynthetic pathways the length of the lower carbon chain is controlled by an unusual chain-length factor supporting biosynthesis either of a triketide in asukamycin or of a tetraketide in colabomycin E. Biological activity assays indicated that colabomycin E significantly inhibited IL-1β release from THP-1 cells and might thus potentially act as an anti-inflammatory agent.

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“…Mycothiazole is a polyketide derived heterocycle isolated from the sponge Spongiu my~ofi7iensis.l~ It showed antihelminthic activity (in v i m ) but was highly toxic to mice. It is suggested that although the disubstituted thiazole ring (21) is novel it is probably biosynthesized from latrunculin B (22).…”

Section: Oh Oh Hmentioning

confidence: 99%

Muscarine, oxazole, thiazole, imidazole, and peptide alkaloids, and other miscellaneous alkaloids

Lewis¹

1991

Nat. Prod. Rep.

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Metabolic products of microorganisms. 244. Colabomycins, new antibiotics of the manumycin group from Streptomyces griseoflavus. I. Isolation, characterization and biological properties.

Cited by 33 publications

References 10 publications

The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

The Synthesis of Alisamycin, Nisamycin, LL-C10037α and Novel Epoxyquinol and Epoxyquinone Analogues of Manumycin A

Biosynthesis of Colabomycin E, a New Manumycin‐Family Metabolite, Involves an Unusual Chain‐Length Factor

Muscarine, oxazole, thiazole, imidazole, and peptide alkaloids, and other miscellaneous alkaloids

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