Nocardicyclin A
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| Category | Antibiotics |
| Catalog number | BBF-02132 |
| CAS | 199173-81-4 |
| Molecular Weight | 585.60 |
| Molecular Formula | C30H35NO11 |
| Purity | >98% by HPLC |
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Description
It is produced by the strain of Nocardia pseudobrasiliensis IFM 0624. Nocardicyclin A is resistant to gram-positive bacteria, mycobacterium and Nocardia and it is more active than B.
Specification
| Synonyms | 1,6,11(2H)-Naphthacenetrione, 3,4-dihydro-3,10-dimethoxy-2-methyl-4-((2,3,6-trideoxy-3-(dimethylamino-3-C-methyl-alpha-lyxo-hexopyranosyl)oxy)-2,5,7-trihydroxy-, (2R,3R,4R)-rel- |
| IUPAC Name | (2R,3R,4R)-4-[(2S,4S,5S,6S)-4-(dimethylamino)-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-2,5,7-trihydroxy-3,10-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(C(=O)C3=CC4=C(C(=C23)O)C(=O)C5=C(C=CC(=C5C4=O)OC)O)(C)O)OC)(C)N(C)C)O |
| InChI | InChI=1S/C30H35NO11/c1-12-26(36)29(2,31(4)5)11-17(41-12)42-25-19-14(27(37)30(3,38)28(25)40-7)10-13-18(23(19)34)24(35)20-15(32)8-9-16(39-6)21(20)22(13)33/h8-10,12,17,25-26,28,32,34,36,38H,11H2,1-7H3/t12-,17-,25+,26+,28+,29-,30-/m0/s1 |
| InChI Key | VOWLRGXRNLYFMV-BSDPKGMPSA-N |
Properties
| Appearance | Red MicroCrystalline |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycobacteria |
| Boiling Point | 785.3°C at 760 mmHg |
| Density | 1.47 g/cm3 |
Reference Reading
1. Mass spectrometric approaches for the identification of anthracycline analogs produced by actinobacteria
Anelize Bauermeister, Tiago Domingues Zucchi, Luiz Alberto Beraldo Moraes J Mass Spectrom. 2016 Jun;51(6):437-45. doi: 10.1002/jms.3772.
Anthracyclines are a well-known chemical class produced by actinobacteria used effectively in cancer treatment; however, these compounds are usually produced in few amounts because of being toxic against their producers. In this work, we successfully explored the mass spectrometry versatility to detect 18 anthracyclines in microbial crude extract. From collision-induced dissociation and nuclear magnetic resonance spectra, we proposed structures for five new and identified three more anthracyclines already described in the literature, nocardicyclins A and B and nothramicin. One new compound 8 (4-[4-(dimethylamino)-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-2,5,7,12-tetrahydroxy-3,10-dimethoxy-2-methyl-3,4-dihydrotetracene-1,6,11-trione) was isolated and had its structure confirmed by (1) H nuclear magnetic resonance. The anthracyclines identified in this work show an interesting aminoglycoside, poorly found in natural products, 3-methyl-rhodosamine and derivatives. This fact encouraged to develop a focused method to identify compounds with aminoglycosides (rhodosamine, m/z 158; 3-methyl-rhodosamine, m/z 172; 4'-O-acethyl-3-C-methyl-rhodosamine, m/z 214). This method allowed the detection of four more anthracyclines. This focused method can also be applied in the search of these aminoglycosides in other microbial crude extracts. Additionally, it was observed that nocardicyclin A, nothramicin and compound 8 were able to interact to DNA through a DNA-binding study by mass spectrometry, showing its potential as anticancer drugs. Copyright © 2016 John Wiley & Sons, Ltd.
2. Nocardicyclins A and B: new anthracycline antibiotics produced by Nocardia pseudobrasiliensis
Y Tanaka, U Gräfe, K Yazawa, Y Mikami, M Ritzau J Antibiot (Tokyo). 1997 Oct;50(10):822-7. doi: 10.7164/antibiotics.50.822.
Nocardicyclins A (1) and B (2), new anthracycline antibiotics have been isolated from the mycelial cake of Nocardia pseudobrasiliensis IFM 0624 (JCM 9894). The molecular formulae of 1 and 2 have been determined as C30H35NO11 and C32H37NO12, respectively, and the structures were characterized by 1- and 8-methoxyl groups, a 10-carbonyl group and a novel carbon-methylated aminosugar constituent. Nocardicyclin A (1) exerts cytotoxic activity against L1210 and P388 leukemia. Nocardicyclins A (1) and B (2) are active against Gram-positive bacteria including Mycobacterium spp. and Nocardia spp., but inactive against Gram-negative 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 ╳
