Rabelomycin
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| Category | Antibiotics |
| Catalog number | BBF-02167 |
| CAS | |
| Molecular Weight | 338.31 |
| Molecular Formula | C19H14O6 |
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Description
Rabelomycin is originally isolated from Str.olivaceus. Rabelomycin only works against gram-positive bacteria.
Specification
| Synonyms | ZINC4654730 |
| IUPAC Name | (3R)-3,6,8-trihydroxy-3-methyl-2,4-dihydrobenzo[a]anthracene-1,7,12-trione |
| Canonical SMILES | CC1(CC2=CC(=C3C(=C2C(=O)C1)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O |
| InChI | InChI=1S/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1 |
| InChI Key | JJOLHRYZQSDLSA-LJQANCHMSA-N |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 193°C |
Reference Reading
1. Enhancement of angucycline production by combined UV mutagenesis and ribosome engineering and fermentation optimization in Streptomyces dengpaensis XZHG99T
Yumei Li, Jiyu Li, Zhengmao Ye, Lingchao Lu Prep Biochem Biotechnol. 2021;51(2):173-182. doi: 10.1080/10826068.2020.1805754. Epub 2020 Aug 20.
Strain improvement of Streptomyces dengpaensis XZHG99T was performed by combined UV mutagenesis and ribosome engineering, as well as fermentation optimization for enhanced angucycline production (rabelomycin and saquayamycin B1). First, four streptomycin-resistant mutants were obtained after screening of UV mutagenesis and ribosome engineering. Then a rpsL mutant (HTT7) with higher productivity of rabelomycin and saquayamycin B1 was selected according to genetic screening and HPLC/LC-MS analyses, whose maximum titers of rabelomycin and saquayamycin B1 were 3.6 ± 0.02 mg/L and 7.5 ± 0.04 mg/L, respectively, about fourfold higher than those produced by XZHG99T. Next, fermentation optimization of HTT7 was successively carried out by single-factor experiments in shake flasks. The titers of rabelomycin and saquayamycin B1 were increased to 11.2 ± 0.04 mg/L and 20.5 ± 0.02 mg/L after optimization of shake flask fermentation conditions, respectively, which was increased about sixfold compared with those produced by XZHG99T. Finally, the titers of rabelomycin and saquayamycin B1 reached 15.7 ± 0.05 mg/L and 39.9 ± 0.05 mg/L after the scaled-up fermentation, which was 7.8-fold and 11.4-fold higher than those produced by XZHG99T, respectively. These data demonstrate that the combined empirical strain-breeding approaches are still an effective and convenient pathway to improve strain production ability.
2. An efficient system for stable markerless integration of large biosynthetic gene clusters into Streptomyces chromosomes
Dominika Csolleiova, Renata Knirschova, Bronislava Rezuchova, Dagmar Homerova, Beatrica Sevcikova, Maria Matulova, Luz Elena Núñez, Renata Novakova, Lubomira Feckova, Rachel Javorova, Jesús Cortés, Jan Kormanec Appl Microbiol Biotechnol. 2021 Mar;105(5):2123-2137. doi: 10.1007/s00253-021-11161-w. Epub 2021 Feb 10.
The bacteria of the genus Streptomyces are among the most important producers of biologically active secondary metabolites. Moreover, recent genomic sequence data have shown their enormous genetic potential for new natural products, although many new biosynthetic gene clusters (BGCs) are silent. Therefore, efficient and stable genome modification techniques are needed to activate their production or to manipulate their biosynthesis towards increased production or improved properties. We have recently developed an efficient markerless genome modification system for streptomycetes based on positive blue/white selection of double crossovers using the bpsA gene from indigoidine biosynthesis, which has been successfully applied for markerless deletions of genes and BGCs. In the present study, we optimized this system for markerless insertion of large BGCs. In a pilot test experiment, we successfully inserted a part of the landomycin BGC (lanFABCDL) under the control of the ermEp* promoter in place of the actinorhodin BGC (act) of Streptomyces lividans TK24 and RedStrep 1.3. The resulting strains correctly produced UWM6 and rabelomycin in twice the yield compared to S. lividans strains with the same construct inserted using the PhiBT1 phage-based integration vector system. Moreover, the system was more stable. Subsequently, using the same strategy, we effectively inserted the entire BGC for mithramycin (MTM) in place of the calcium-dependent antibiotic BGC (cda) of S. lividans RedStrep 1.3 without antibiotic-resistant markers. The resulting strain produced similar levels of MTM when compared to the previously described S. lividans RedStrep 1.3 strain with the VWB phage-based integration plasmid pMTMF. The system was also more stable. KEY POINTS: · Optimized genome editing system for markerless insertion of BGCs into Streptomyces genomes · Efficient heterologous production of MTM in the stable engineered S. lividans strain.
3. Purification and characterization of anti-phytopathogenic fungi angucyclinone from soil-derived Streptomyces cellulosae
Xindong Xu, Yang Zhao, Kang Bao, Cuiping Miao, Lixing Zhao, Youwei Chen, Shaohua Wu, Yiqing Li Folia Microbiol (Praha). 2022 Jun;67(3):517-522. doi: 10.1007/s12223-022-00957-6. Epub 2022 Feb 22.
Actinomycete strain YIM PH20352, isolated from the rhizosphere soil sample of Panax notoginseng collected in WenShang, Yunnan Province, China, exhibited antifungal activity against some phytopathogenic fungi. The structures of bioactive molecules, isolated from the ethyl acetate extract of the fermentation broth of the strain, were identified as rabelomycin (1) and dehydrorabelomycin (2) based on extensive spectroscopic analyses. Compound 1 exhibited antifungal activity against four tested root-rot pathogens of the Panax notoginseng including Plectosphaerella cucumerina, Alternaria panax, Fusarium oxysporum, and Fusarium solani with the MIC values at 32, 64, 128, and 128 μg/mL, respectively. Compound 2 exhibited antifungal activity against F. oxysporum, P. cucumerina, F. solani, and A. panax with the MIC values at 64, 64, 128, and 128 μg/mL, respectively. Based on the phylogenetic analyses, the closest phylogenetic relative of strain YIM PH20352 is Streptomyces cellulosae NBRC 13027 T (AB184265) (99.88%), so strain YIM PH20352 was identified as Streptomyces cellulosae. To the best of our knowledge, this is the first report of rabelomycin and rabelomycin-type antibiotics from Streptomyces cellulosae and their antifungal activity against root-rot pathogens of the Panax notoginseng.
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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 ╳
