Heliomycin
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| Category | Antibiotics |
| Catalog number | BBF-01812 |
| CAS | 11029-70-2 |
| Molecular Weight | 376.36 |
| Molecular Formula | C22H16O6 |
| Purity | >95% by HPLC |
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Description
It is produced by the strain of Actinomyces flavochromogenes var. heliomycini. It is a quinone antibiotic. It can inhibit RNA formation, has strong anti-gram-positive bacterial activity, and has vasoconstriction effect. It is used to treat burns and pyoderma and can also be added to cosmetics.
Specification
| Related CAS | 20004-62-0 |
| Synonyms | Geliomycin; Croceomycin; Heliomycin; Itamycin; Antibiotic A 3733A; 2H-Benzo(cd)pyrene-2,6(1H)-dione,3,5,7,10-tetrahydroxy-1,1,9-trimethyl- |
| Storage | -20 °C |
| IUPAC Name | 6,10,14,19-tetrahydroxy-4,9,9-trimethylpentacyclo[13.3.1.05,18.08,17.011,16]nonadeca-1(19),3,5,7,10,13,15,17-octaene-2,12-dione |
| Canonical SMILES | CC1=CC(=O)C2=C(C3=C4C5=C2C1=C(C=C5C(C(=C4C(=O)C=C3O)O)(C)C)O)O |
| InChI | InChI=1S/C22H16O6/c1-7-4-9(23)15-18-13(7)10(24)5-8-14(18)19-16(20(15)27)11(25)6-12(26)17(19)21(28)22(8,2)3/h4-6,24-25,27-28H,1-3H3 |
| InChI Key | MJKDGCARCYPVQG-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 765.3 °C at 760 mmHg |
| Melting Point | 315-325 °C (dec.) |
| Density | 1.60 g/cm3 |
| Solubility | Soluble in Pyridine, Acetone, Ethanol, DMF, DMSO; Insoluble in Water |
Reference Reading
1. Inhibitory and ameliorative effect of heliomycin derived from actinomycete on induced hepatocellular carcinoma in rats
Mohamed M Omran, Ehab A Essawy, Mohga S Abdalla, Mohamed S Abdelfattah, Abdulla A Mahmoud, Ahmed S Alazzouni Naunyn Schmiedebergs Arch Pharmacol . 2021 Jun;394(6):1091-1102. doi: 10.1007/s00210-020-02043-5.
The hepatoprotective activity of heliomycin obtained from the culture broth of actinomycete AB5 against diethylnitrosamine (DEN)-induced hepatic cancer in Wistar rats was estimated. Heliomycin exhibited a significant decrease in the levels of alanine transaminase (ALT), aspartate transaminase (AST), and alkaline phosphatase (ALP) compared to the positive control. For instance, the heliomycin group after 20 weeks showed a significant decline in ALT, AST, and ALP values (70.75 ± 5.12, 140.25 ± 11.75, and 163.25 ± 18.66, respectively) compared to the positive control group (170.00 ± 9.55, 252.75 ± 12.33, and 278.00 ± 21.32, respectively). Additionally, the isolated compound showed a highly significant decrease in serum alpha-fetoprotein (AFP) levels. After 8, 16, and 20 weeks, the mean values of AFP in the heliomycin group revealed a highly significant decrease (33.62 ± 2.46, 30.00 ± 4.05, and 28.50 ± 2.64, respectively) compared to the positive control group (49.45 ± 3.03, 81.90 ± 6.70, and 90.75 ± 5.12, respectively). The histopathological investigation of liver sections supported the results of biochemical analysis. It was demonstrated that heliomycin showed histological improvement of hepatocytes and marked increase of nuclear pyknotic with clear cytoplasm, which is a sign of improving the apoptotic pathway of malignant cells. It also displayed marked fibrosis at most of the malignant cells and the development of some regenerative nodules. Heliomycin showed moderate immunoreactivity with alpha-fetoprotein (AFP), and proliferation cell nuclear antigen (PCNA) compared to the positive control group. To the best of our knowledge, this is the first study to report the anticancer activity of heliomycin against hepatocellular carcinoma in vivo.
2. Heliomycin and tetracinomycin D: anthraquinone derivatives with histone deacetylase inhibitory activity from marine sponge-associated Streptomyces sp. SP9
Neama Hassan Ali, Mohammed Ismail Youssef Elmallah, Ahmed Hassan Ibrahim Faraag, Ali Mohamed Salah Hebishy, Mohamed Saleh Abdelfattah 3 Biotech . 2018 Jun;8(6):282. doi: 10.1007/s13205-018-1304-1.
Several actinomycetes strains were isolated from different marine sponges collected from the Red Sea shore in Egypt. The efficiency of their crude extracts to inhibit histone deacetylase (HDAC) enzyme was investigated in the nuclear extract of Hela cell line. The crude extract corresponding toStreptomycessp. SP9 isolated from the marine spongePseudoceratina arabicashowed a promising HDAC inhibitory activity with 64 and 81% at 50 and 100 µg/ml, respectively. The strain was identified asStreptomycessp. by phylogenetic analyses based on its 16S rRNA gene sequence. The major compounds ofStreptomycessp. SP9 were isolated and purified by different chromatographic methods. The chemical structure of the isolated compounds was identified on the basis of their spectroscopic data including mass,1H and13C NMR, and by comparison with those of authenticated samples. Structures of compounds1and2were established as heliomycin and tetracenomycin D, respectively. These compounds exhibited HDAC inhibitory activities with IC50values of 29.8 ± 0.04 µg/ml for heliomycin (1) and 10.9 ± 0.02 µg/ml for tetracenomycin D (2). A computational docking study for compounds1and2against HDAC1, HDAC2, and HDAC3 was performed to formulate a hypothetical mechanism by which the tested compounds inhibit HDAC. Tetracenomycin D (2) showed a good binding interactions with HDAC2 (- 5.230 kcal/mol) and HDAC3 (- 6.361 kcal/mol).
3. [Action of heliomycin on protein and mucleic acid synthesis in Staphylococcus aureus]
A N Polin, P N Korolev, V G Bulgakova, E I Melikhova, A B Silaev Antibiotiki . 1975 Apr;20(4):350-4.
Heliomycin inhibited synthesis of RNA in Staph. aureua which was clearly shown in the study of the antibiotic effect on RNA synthesis in the lag phase of the culture development: heliomycin markedly lowered the maximum RNA level in the biomass observed in the culture at the beginning of the exponential growth. On further growth of the culture heliomycin induced a significant retardness of the process of the natural decrease in the RNA biomass level resulting in increased content of RNA in the cells growing in the presence of heliomycin as compared to the control culture. Retarded natural decrease in the RNA biomass level in the presence of heliomycin was observed also on the antibiotic addition just at the beginning of the exponential growth, during the period of maximum RNA accumulation in the cells. Heliomycin had no effect on synthesis and biomass levels of DNA. Heliomycin inhibited the protein synthesis and was close to chloramphenicol by the level of inhibition of the summation protein synthesis in the biomass. However, comparison of the effect of the above antibiotics on synthesis of beta-galactosidase, an individual enzyme protein showed that heliomycin was much less active as an inhibitor of protein synthesis in comparison to chloramphenicol.
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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 ╳
