Benzastatin C
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| Category | Others |
| Catalog number | BBF-00289 |
| CAS | |
| Molecular Weight | 350.88 |
| Molecular Formula | C19H27ClN2O2 |
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Description
Benzastatin C is produced by the strain of Streptomyces nitrosporeas 30643. All the components can inhibit the lipid peroxidation activity of rat liver microsomes.
Specification
| Synonyms | CHEBI:65483; Q27133927 |
| IUPAC Name | (2R,3R)-3-chloro-2-(3,4-dimethylpent-3-enyl)-2-(methoxymethyl)-3,4-dihydro-1H-quinoline-6-carboxamide |
| Canonical SMILES | CC(=C(C)CCC1(C(CC2=C(N1)C=CC(=C2)C(=O)N)Cl)COC)C |
| InChI | InChI=1S/C19H27ClN2O2/c1-12(2)13(3)7-8-19(11-24-4)17(20)10-15-9-14(18(21)23)5-6-16(15)22-19/h5-6,9,17,22H,7-8,10-11H2,1-4H3,(H2,21,23)/t17-,19-/m1/s1 |
| InChI Key | AHGKSZXKDPGMQU-IEBWSBKVSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Benzastatins A, B, C, and D: new free radical scavengers from Streptomyces nitrosporeus 30643. II. Structural determination
W G Kim, J P Kim, I D Yoo J Antibiot (Tokyo). 1996 Jan;49(1):26-30. doi: 10.7164/antibiotics.49.26.
The structures of benzastatins A, B, C, and D, new free radical scavengers, were determined by spectroscopic studies. Benzastatins A and B incorporate the para-aminobenzamide unit which is rare in fungal metabolites. Benzastatins C and D are unique alkaloids related to virantmycin; they contain the tetrahydroquinoline unit in the molecules.
2. Benzastatins A, B, C, and D: new free radical scavengers from Streptomyces nitrosporeus 30643. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
W G Kim, J P Kim, C J Kim, K H Lee, I D Yoo J Antibiot (Tokyo). 1996 Jan;49(1):20-5. doi: 10.7164/antibiotics.49.20.
In the course of screening for free radical scavengers, rare metabolites, benzastatins A and B having aminobenzamide skeleton and benzastatins C and D having tetrahydroquinoline skeleton, were isolated from the culture broth of streptomyces nitrosporeus 30643. They showed inhibitory activity against lipid peroxidation in rat liver microsomes. In the cell assay, benzastatins C and D inhibited glutamate toxicity in N18-RE-105 cells with EC50 values of 2.0 and 5.4 microM, respectively.
3. Differential antiviral activity of benzastatin C and its dechlorinated derivative from Streptomyces nitrosporeus
Jong-Gyo Lee, Ick-Dong Yoo, Won-Gon Kim Biol Pharm Bull. 2007 Apr;30(4):795-7. doi: 10.1248/bpb.30.795.
Benzastatin C, a 3-chloro-tetrahydroquinolone alkaloid from Streptomyces nitrosporeus, showed antiviral activity in a dose-dependant manner with EC50 values of 1.92, 0.53, and 1.99 microg/ml against herpes simplex virus type 1 (HSV-1), herpes simplex virus type 2 (HSV-2), and vesicular stomatitis virus (VSV), respectively. In contrast, benzastatin D, the corresponding dechlorinated derivative, did not exhibit any antiviral activity. These results indicate that the antiviral activity of benzastatin C is mediated, in part, due to the chlorine moiety in its molecular structure.
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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 ╳
