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Benzastatin D

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Category Others
Catalog number BBF-00290
CAS
Molecular Weight 332.44
Molecular Formula C19H28N2O3

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Fermentation Lab

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Benzastatin D is produced by the strain of Streptomyces nitrosporeas 30643. All the components can inhibit the lipid peroxidation activity of rat liver microsomes.

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IUPAC Name (2R,3R)-2-(3,4-dimethylpent-3-enyl)-3-hydroxy-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)O)COC)C
InChI InChI=1S/C19H28N2O3/c1-12(2)13(3)7-8-19(11-24-4)17(22)10-15-9-14(18(20)23)5-6-16(15)21-19/h5-6,9,17,21-22H,7-8,10-11H2,1-4H3,(H2,20,23)/t17-,19-/m1/s1
InChI Key HUGKMANAUQJUGU-IEBWSBKVSA-N
Appearance White Powder
1. 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.
2. 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.
3. 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.

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