Diolmycin A1
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| Category | Antibiotics |
| Catalog number | BBF-01155 |
| CAS | 150408-69-8 |
| Molecular Weight | 297.35 |
| Molecular Formula | C18H19NO3 |
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Description
It is produced by the strain of Streptomyces sp. WK-2955. It is an antibiotic with anticoccidial activity.
Specification
| IUPAC Name | (2R,3S)-1-(4-hydroxyphenyl)-4-(1H-indol-3-yl)butane-2,3-diol |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)CC(C(CC3=CC=C(C=C3)O)O)O |
| InChI | InChI=1S/C18H19NO3/c20-14-7-5-12(6-8-14)9-17(21)18(22)10-13-11-19-16-4-2-1-3-15(13)16/h1-8,11,17-22H,9-10H2/t17-,18+/m1/s1 |
| InChI Key | WSPKULGBZAOXCJ-MSOLQXFVSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Parasites |
| Solubility | Soluble in Methanol |
Reference Reading
1. Specialized Metabolism of Gordonia Genus: An Integrated Survey on Chemodiversity Combined with a Comparative Genomics-Based Analysis
Jeysson Sánchez-Suárez, Luis Díaz, Ericsson Coy-Barrera, Luisa Villamil BioTech (Basel). 2022 Nov 21;11(4):53. doi: 10.3390/biotech11040053.
Members of the phylum Actinomycetota (formerly Actinobacteria) have historically been the most prolific providers of small bioactive molecules. Although the genus Streptomyces is the best-known member for this issue, other genera, such as Gordonia, have shown interesting potential in their specialized metabolism. Thus, we combined herein the result of a comprehensive literature survey on metabolites derived from Gordonia strains with a comparative genomic analysis to examine the potential of the specialized metabolism of the genus Gordonia. Thirty Gordonia-derived compounds of different classes were gathered (i.e., alkaloids, amides, phenylpropanoids, and terpenoids), exhibiting antimicrobial and cytotoxic activities, and several were also isolated from Streptomyces (e.g., actinomycin, nocardamin, diolmycin A1). With the genome data, we estimated an open pan-genome of 57,901 genes, most of them being part of the cloud genome. Regarding the BGCs content, 531 clusters were found, including Terpenes, RiPP-like, and NRPS clusters as the most frequent clusters. Our findings demonstrated that Gordonia is a poorly studied genus in terms of its specialized metabolism production and potential applications. Nevertheless, given their BGCs content, Gordonia spp. are a valuable biological resource that could expand the chemical spectrum of the phylum Actinomycetota, involving novel BGCs for inspiring innovative outlines for synthetic biology and further use in biotechnological initiatives. Therefore, further studies and more efforts should be made to explore different environments and evaluate other bioactivities.
2. Diolmycins, new anticoccidial agents produced by Streptomyces sp. II. Structure elucidation of diolmycins A1, A2, B1 and B2, and synthesis of diolmycin A1
N Tabata, T Sunazuka, H Tomoda, T Nagamitsu, Y Iwai, S Omura J Antibiot (Tokyo). 1993 May;46(5):762-9. doi: 10.7164/antibiotics.46.762.
The structures of diolmycins A1, A2, B1 and B2, novel anticoccidial agents, were determined by spectroscopic analyses. Diolmycins A1 and A2 are stereoisomers with the structure of 1-(3-indolyl)-4-(p-hydroxyphenyl)-2,3-butanediol. From the chemical synthesis of the erythro-isomer, the relative configurations of diolmycins A1 and A2 were determined to be the erythro- and threo-isomers, respectively. The stereoisomers, diolmycins B1 and B2, were also deduced to be erythro- and threo-1,4-di-(p-hydroxyphenyl)-2,3-butanediol, respectively.
3. Diolmycins, new anticoccidial agents produced by Streptomyces sp. I. Production, isolation and physico-chemical and biological properties
N Tabata, H Tomoda, Y Takahashi, K Haneda, Y Iwai, H B Woodruff, S Omura J Antibiot (Tokyo). 1993 May;46(5):756-61. doi: 10.7164/antibiotics.46.756.
Streptomyces sp. WK-2955, a soil isolate, was found to produce a series of new anticoccidial compounds. Four active compounds, designated diolmycins A1, A2, B1 and B2, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography, gel filtration on Sephadex LH-20, and preparative HPLC. Diolmycins inhibited the growth of Eimeria tenella in an in vitro assay system using BHK-21 cells as a host. No schizont in the cells was observed at concentrations of 0.02-2.0 micrograms/ml for diolmycin A1, at 0.2-2.0 micrograms/ml for diolmycin A2, and at 20 micrograms/ml for diolmycins B1 and B2.
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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 ╳
