Collinomycin
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| Category | Antibiotics |
| Catalog number | BBF-01040 |
| CAS | 27267-69-2 |
| Molecular Weight | 536.44 |
| Molecular Formula | C27H20O12 |
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Description
It is produced by the strain of Streptomyces collinus. It has anti-gram-positive bacterial activity and inhibits human immunodeficiency virus-1 (HIV-1) reverse transcriptase activity.
Specification
| Synonyms | alpha-Rubromycin; Rubromycin; Tuoromycin; Methyl 7,8-dihydroxy-6-[2-(8-hydroxy-5,7-dimethoxy-4,9-dioxo-4,9-dihydronaphtho[2,3-b]furan-2-yl)ethyl]-1-oxo-1H-2-benzopyran-3-carboxylate |
| IUPAC Name | methyl 7,8-dihydroxy-6-[2-(8-hydroxy-5,7-dimethoxy-4,9-dioxobenzo[f][1]benzofuran-2-yl)ethyl]-1-oxoisochromene-3-carboxylate |
| Canonical SMILES | COC1=CC(=C(C2=C1C(=O)C3=C(C2=O)OC(=C3)CCC4=C(C(=C5C(=C4)C=C(OC5=O)C(=O)OC)O)O)O)OC |
| InChI | InChI=1S/C27H20O12/c1-35-14-9-15(36-2)22(30)19-18(14)21(29)13-8-12(38-25(13)24(19)32)5-4-10-6-11-7-16(26(33)37-3)39-27(34)17(11)23(31)20(10)28/h6-9,28,30-31H,4-5H2,1-3H3 |
| InChI Key | LQNGOIZVRFNQLO-UHFFFAOYSA-N |
Properties
| Appearance | Red Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Viruses |
| Boiling Point | 833.9 °C at 760 mmHg |
| Melting Point | 278-281 °C |
| Density | 1.568 g/cm3 |
Reference Reading
1. Trait Differentiation within the Fungus-Feeding (Mycophagous) Bacterial Genus Collimonas
Max-Bernhard Ballhausen, Peter Vandamme, Wietse de Boer PLoS One. 2016 Jun 16;11(6):e0157552. doi: 10.1371/journal.pone.0157552. eCollection 2016.
The genus Collimonas consists of facultative, fungus-feeding (mycophagous) bacteria. To date, 3 species (C. fungivorans, C. pratensis and C. arenae) have been described and over 100 strains have been isolated from different habitats. Functional traits of Collimonas bacteria that are potentially involved in interactions with soil fungi mostly negatively (fungal inhibition e.g.), but also positively (mineral weathering e.g.), affect fungal fitness. We hypothesized that variation in such traits between Collimonas strains leads to different mycophagous bacterial feeding patterns. We investigated a) whether phylogenetically closely related Collimonas strains possess similar traits, b) how far phylogenetic resolution influences the detection of phylogenetic signal (possession of similar traits by related strains) and c) if there is a pattern of co-occurrence among the studied traits. We measured genetically encoded (nifH genes, antifungal collimomycin gene cluster e.g.) as well as phenotypically expressed traits (chitinase- and siderophore production, fungal inhibition and others) and related those to a high-resolution phylogeny (MLSA), constructed by sequencing the housekeeping genes gyrB and rpoB and concatenating those with partial 16S rDNA sequences. Additionally, high-resolution and 16S rDNA derived phylogenies were compared. We show that MLSA is superior to 16SrDNA phylogeny when analyzing trait distribution and relating it to phylogeny at fine taxonomic resolution (a single bacterial genus). We observe that several traits involved in the interaction of collimonads and their host fungus (fungal inhibition e.g.) carry phylogenetic signal. Furthermore, we compare Collimonas trait possession with sister genera like Herbaspirillum and Janthinobacterium.
2. Interruption of Aspergillus niger spore germination by the bacterially produced secondary metabolite collimomycin
Sandra Mosquera, Ioannis Stergiopoulos, Johan H J Leveau Environ Microbiol Rep. 2020 Jun;12(3):306-313. doi: 10.1111/1758-2229.12833. Epub 2020 Mar 21.
Collimonas fungivorans Ter331 (CfTer331) is a soil bacterium that produces collimomycin, a secondary metabolite that inhibits the vegetative growth of fungi. Here we show that CfTer331 can also interfere with fungal spore germination and that collimomycin biosynthesis is required for this activity. More specifically, in co-cultures of Aspergillus niger N402 (AnN402) co-nidiospores with CfTer331, the rate of transition from the isotropic to polarized stage of the germination process was reduced and the relatively few AnN402 conidiospores that completed the germination process were less likely to survive than those that were arrested in the isotropic phase. By contrast, a collimomycin-deficient mutant of CfTer331 had no effect on germination: in its presence, as in the absence or delayed presence of CfTer331, unhindered germination of conidiospores allowed rapid establishment of AnN402 mycelium and the subsequent acidification of the culture medium to the detriment of any bacteria present. However, when challenged early enough with CfTer331, the collimomycin-dependent arrest of the AnN402 germination process enabled CfTer331 to prevent AnN402 from forming mycelia and to gain dominance in the culture. We propose that the collimomycin-dependent arrest of spore germination represents an early intervention strategy used by CfTer331 to mitigate niche construction by fungi in nature.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
