Streptovitacin A
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| Category | Antibiotics |
| Catalog number | BBF-03075 |
| CAS | 523-86-4 |
| Molecular Weight | 297.35 |
| Molecular Formula | C15H23NO5 |
| Purity | >98% |
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Description
Streptovitacin A is an antibiotic produced by Str. griseus. It has antifungal and protozoan activity and can inhibit the effect of KB cells.
Specification
| Synonyms | Streptovitacin; Resactin A |
| Storage | Store at -20°C |
| IUPAC Name | 4-[2-hydroxy-2-(5-hydroxy-3,5-dimethyl-2-oxocyclohexyl)ethyl]piperidine-2,6-dione |
| Canonical SMILES | CC1CC(CC(C1=O)C(CC2CC(=O)NC(=O)C2)O)(C)O |
| InChI | InChI=1S/C15H23NO5/c1-8-6-15(2,21)7-10(14(8)20)11(17)3-9-4-12(18)16-13(19)5-9/h8-11,17,21H,3-7H2,1-2H3,(H,16,18,19) |
| InChI Key | NFDQYBUVHVRNNY-UHFFFAOYSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | fungi; parasites; neoplastics (Tumor) |
| Boiling Point | 535.1±35.0°C at 760 mmHg |
| Melting Point | 156-159°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Bioactive Streptoglutarimides A-J from the Marine-Derived Streptomyces sp. ZZ741
Di Zhang, Wenwen Yi, Hengju Ge, Zhizhen Zhang, Bin Wu J Nat Prod. 2019 Oct 25;82(10):2800-2808. doi: 10.1021/acs.jnatprod.9b00481. Epub 2019 Oct 4.
The new streptoglutarimides A-J (1-10) and the known streptovitacin A (11) were isolated from a marine-derived actinomycete, Streptomyces sp. ZZ741. Structures of the isolated compounds were elucidated based on their HRESIMS data, extensive NMR spectroscopic analyses, ECD calculations, Mosher's method, and a single-crystal X-ray diffraction experiment. Streptoglutarimide H (8) and streptovitacin A (11) showed potent antiproliferative activity against human glioma U87MG and U251 cells with IC50 values of 1.5-3.8 μM for 8 and 0.05-0.22 μM for 11. All isolated compounds exhibited antimicrobial activity with MIC values of 9-11 μg/mL against methicillin-resistant Staphylococcus aureus, 8-12 μg/mL against Escherichia coli, and 8-20 μg/mL against Candida albicans.
2. Structure-activity relationship of 9-methylstreptimidone, a compound that induces apoptosis selectively in adult T-cell leukemia cells
Masatoshi Takeiri, Eisuke Ota, Shigeru Nishiyama, Hiromasa Kiyota, Kazuo Umezawa Oncol Res. 2012;20(1):7-14. doi: 10.3727/096504012x13425470196056.
We previously reported that 9-methylstreptimidone, a piperidine compound isolated from a culture filtrate of Streptomyces, induces apoptosis selectively in adult T-cell leukemia cells. It was screened for a compound that inhibits LPS-induced NF-kappaB and NO production in mouse macrophages. However, 9-methystreptimidone is poorly obtained from the producing microorganism and difficult to synthesize. Therefore, in the present research, we studied the structure-activity relationship to look for new selective inhibitors. We found that the structure of the unsaturated hydrophobic portion of 9-methylstreptimidone was essential for the inhibition of LPS-induced NO production. Among the 9-methylstreptimidone-related compounds tested, (+/-)-4,alpha-diepi-streptovitacin A inhibited NO production in macrophage-like cells as potently as 9-methylstreptimidone and without cellular toxicity. Moreover, this compound selectively induced apoptosis in adult T-cell leukemia MT-1 cells.
3. Syntheses and biological activities of (+/-)-streptovitacin A and E-73
H Kondo, T Oritani, K Yamashita Agric Biol Chem. 1990 Jun;54(6):1531-6.
(+/-)-Streptovitacin A (1) and its stereoisomers were synthesized by an aldol reaction of (+/-)-2,4-dimethyl-4-trimethylsiloxy-1-cyclohexanones (4b and 9) with 4-(2-oxoethyl)-2,6-piperidinedione (5). E-72 (2) was derived from synthetic 1. (+/-)-1 showed moderate growth inhibition against fungi and lettuce seeds.
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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 ╳
