Benzanthrin A
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| Category | Antibiotics |
| Catalog number | BBF-00285 |
| CAS | 103523-24-6 |
| Molecular Weight | 634.71 |
| Molecular Formula | C35H42N2O9 |
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Description
Benzanthrin A is produced by the strain of Nocardia lurida. It mainly has the activity of anti-gram-positive bacteria. B is 10 times more toxic to 9ASK cells than A.
Specification
| IUPAC Name | 2-[(2R,4S,5S,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]-1-[(2S,4R,5R,6R)-4-(dimethylamino)-5-hydroxy-6-methyloxan-2-yl]oxy-6,8-dihydroxy-3-methylbenzo[a]anthracene-7,12-dione |
| Canonical SMILES | CC1C(C(CC(O1)C2=C(C3=C4C(=C(C=C3C=C2C)O)C(=O)C5=C(C4=O)C=CC=C5O)OC6CC(C(C(O6)C)O)N(C)C)N(C)C)O |
| InChI | InChI=1S/C35H42N2O9/c1-15-11-18-12-23(39)29-30(33(42)19-9-8-10-22(38)28(19)34(29)43)27(18)35(46-25-14-21(37(6)7)32(41)17(3)45-25)26(15)24-13-20(36(4)5)31(40)16(2)44-24/h8-12,16-17,20-21,24-25,31-32,38-41H,13-14H2,1-7H3/t16-,17-,20+,21-,24-,25+,31-,32+/m1/s1 |
| InChI Key | LEUWPSNVHJODDS-AWWGJPRGSA-N |
Properties
| Appearance | Dark Red Powder |
| Antibiotic Activity Spectrum | gram-positive bacteria |
Reference Reading
1. Benzanthrins A and B, a new class of quinone antibiotics. I. Discovery, fermentation and antibacterial activity
R J Theriault, R R Rasmussen, W L Kohl, J F Prokop, T B Hutch, G J Barlow J Antibiot (Tokyo). 1986 Nov;39(11):1509-14. doi: 10.7164/antibiotics.39.1509.
Nocardia lurida has been shown to produce two novel quinone antibiotics, benzanthrins A and B. The antibiotics were discovered in concentrated butanol extracts of fermentation broths and were separated by TLC and HPLC. Benzanthrins A and B were produced in a fermentation medium consisting of glucose, yeast, selected peptones and CaCO3. The antibiotics were present primarily at 66 hours in shake flask fermentations and from 66 to 162 hours in 14-liter fermentors. Benzanthrins A and B inhibited a number of Gram-positive pathogenic bacteria but were inactive against Gram-negative bacteria.
2. Benzanthrins A and B, a new class of quinone antibiotics. II. Isolation, elucidation of structure and potential antitumor activity
R R Rasmussen, M E Nuss, M H Scherr, S L Mueller, J B McAlpine, L A Mitscher J Antibiot (Tokyo). 1986 Nov;39(11):1515-26. doi: 10.7164/antibiotics.39.1515.
The benzanthrins, which were produced by Nocardia lurida, were extracted from the fermentation broth with CH2Cl2. Subsequent purification on Sephadex LH-20 and diolbonded silica gel, followed by countercurrent chromatography, afforded analytically pure benzanthrins A and B. FAB-MS revealed that benzanthrins A and B were isomeric. It was demonstrated through degradative and spectroscopic studies that the benzanthrins were di-glycosides of a trihydroxy benz[a]anthraquinone chromophore where one of the sugars was linked through carbon and the other through oxygen. Benzanthrins A and B differed in the stereochemistry of the O-glycosidic sugar. Both compounds inhibited the growth of Gram-positive bacteria and 9KB, 9PS and 9ASK tumor cells in tissue culture.
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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 ╳
