RS-22A
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| Category | Antibiotics |
| Catalog number | BBF-03389 |
| CAS | |
| Molecular Weight | 1054.3 |
| Molecular Formula | C54H91N3O17 |
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Description
RS-22A is a macrolide antibiotic produced by Streptomyces violaceusniger. It is active against gram-positive, gram-negative bacteria, yeast and filamentous fungi.
Specification
| Synonyms | RS-22 A |
| IUPAC Name | 3-[[(10E,12E,18E,20E)-15-[(E)-10-(diaminomethylideneamino)dec-6-en-2-yl]-5,7,9,23,25,27,31,33,34,35-decahydroxy-10,14,22,26,30-pentamethyl-17-oxo-16,37-dioxabicyclo[31.3.1]heptatriaconta-10,12,18,20-tetraen-3-yl]oxy]-3-oxopropanoic acid |
| Canonical SMILES | CC1CCC(C(C(CC(C(C=CC=CC(=O)OC(C(C=CC=C(C(CC(CC(CC(CC2CC(C(C(O2)(CC1O)O)O)O)OC(=O)CC(=O)O)O)O)O)C)C)C(C)CCCC=CCCCN=C(N)N)C)O)O)C)O |
| InChI | InChI=1S/C54H91N3O17/c1-32-16-12-13-20-49(68)73-51(35(4)17-11-9-7-8-10-14-23-57-53(55)56)36(5)19-15-18-33(2)43(61)26-39(59)24-38(58)25-40(72-50(69)30-48(66)67)27-41-28-46(64)52(70)54(71,74-41)31-47(65)34(3)21-22-42(60)37(6)45(63)29-44(32)62/h7-8,12-13,15-16,18-20,32,34-47,51-52,58-65,70-71H,9-11,14,17,21-31H2,1-6H3,(H,66,67)(H4,55,56,57)/b8-7+,16-12+,19-15+,20-13+,33-18+ |
| InChI Key | RMHABCFPUZPVNZ-ONKXNGKDSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; yeast; fungi |
| Melting Point | 132-137°C |
Reference Reading
1. A Potential Biocontrol Agent Streptomyces violaceusniger AC12AB for Managing Potato Common Scab
Arslan Sarwar, Zakia Latif, Songya Zhang, Jianjun Hao, Andreas Bechthold Front Microbiol. 2019 Feb 8;10:202. doi: 10.3389/fmicb.2019.00202. eCollection 2019.
Potato common scab (PCS) is an economically important disease worldwide. In this study we demonstrated the possible role of Streptomyces violaceusniger AC12AB in controlling PCS. Isolates of Streptomyces scabies were obtained from CS infected tubers collected from Maine United States, which were confirmed by morphological and molecular analysis including 16S rRNA sequencing and RFLP analysis of amplified 16S-23S ITS. Pathogenicity assays related genes including txtAB, nec1, and tomA were also identified in all S. scabies strains through PCR reaction. An antagonistic bacterial strain was isolated from soil in Punjab and identified as S. violaceusniger AC12AB based on 16S rRNA sequencing analysis. Methanolic extract of S. violaceusniger AC12AB contained azalomycin RS-22A which was confirmed by 1H and 13C-NMR, 1H/1H-COSY, HMBC and HMQC techniques. S. violaceusniger AC12AB exhibited plant growth promotion attributes including Indole-3-acetic acid production with 17 μgmL-1 titers, siderophores production, nitrogen fixation and phosphates solubilization potential. When tubers were inoculated with S. violaceusniger AC12AB, significant (P < 0.05) PCS disease reduction up to 90% was observed in greenhouse and field trials, respectively. Likewise, S. violaceusniger AC12AB significantly (P < 0.05) increased potato crop up to 26.8% in field trial. Therefore, plant growth promoting S. violaceusniger AC12AB could provide a dual benefit by decreasing PCS disease severity and increasing potato yield as an effective and inexpensive alternative strategy to manage this disease.
2. RS-22A, B and C: new macrolide antibiotics from Streptomyces violaceusniger. II. Physico-chemical properties and structure elucidation
M Ubukata, T Morita, H Osada J Antibiot (Tokyo). 1995 Apr;48(4):293-9. doi: 10.7164/antibiotics.48.293.
RS-22A, B and C are novel 36-membered macrolide antibiotics produced by Streptomyces violaceusniger. The structures of these antibiotics were unambiguously determined by 1D and 2D NMR and tandem-mass analysis of the oxidative derivative of RS-22C.
3. RS-22A, B and C: new macrolide antibiotics from Streptomyces violaceusniger. I. Taxonomy, fermentation, isolation and biological activities
M Ubukata, N Shiraishi, K Kobinata, T Kudo, I Yamaguchi, H Osada, Y C Shen, K Isono J Antibiot (Tokyo). 1995 Apr;48(4):289-92. doi: 10.7164/antibiotics.48.289.
Three novel 36-membered macrolide antibiotics, RS-22A, B and C produced by Streptomyces violaceusniger have been isolated. These antibiotics were purified from an acetone extract of the mycelia followed by butanol extraction, centrifugal partition chromatography and HPLC. RS-22A, B, C showed antimicrobial activity against fungi and Gram-positive bacteria.
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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 ╳
