Nothramicin
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| Category | Antibiotics |
| Catalog number | BBF-02138 |
| CAS | 205752-47-2 |
| Molecular Weight | 587.61 |
| Molecular Formula | C30H37NO11 |
| Purity | >95% |
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Description
It is an anthracycline antibiotic with anti-mycobacterial activity produced by the strain of Nocardia sp. MJ 896-43F.
Specification
| Synonyms | 3,4,10,12-tetrahydroxy-2,7-dimethoxy-3-methyl-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-3-(dimethylamino)-3-methylhexopyranoside |
| IUPAC Name | 7-[4-(dimethylamino)-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,6,9,10-tetrahydroxy-1,8-dimethoxy-9-methyl-8,10-dihydro-7H-tetracene-5,12-dione |
| Canonical SMILES | CC1C(C(CC(O1)OC2C(C(C(C3=CC4=C(C(=C23)O)C(=O)C5=C(C=CC(=C5C4=O)OC)O)O)(C)O)OC)(C)N(C)C)O |
| InChI | InChI=1S/C30H37NO11/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/h8-10,12,17,25-28,32,34,36-38H,11H2,1-7H3 |
| InChI Key | XXHMZNPASHQZPM-UHFFFAOYSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | mycobacteria |
| Boiling Point | 756.5°C at 760 mmHg |
| Melting Point | 140-145°C |
| Density | 1.47 g/cm3 |
Reference Reading
1. Nothramicin, a new anthracycline antibiotic from Nocardia sp. MJ896-43F17
I Momose, N Kinoshita, R Sawa, H Naganawa, H Iinuma, M Hamada, T Takeuchi J Antibiot (Tokyo). 1998 Feb;51(2):130-5. doi: 10.7164/antibiotics.51.130.
A new antibiotic designated nothramicin was isolated from the culture broth of Nocardia sp. MJ896-43F17 which was closely related to Nocardia brasiliensis. It was isolated by the Diaion HP-20 column chromatography, butyl acetate extraction and purified by HPLC. It inhibited the growth of mycobacteria at the concentration of 1.56 approximately 25 microg/ml. Nothramicin was revealed to be a new member of anthracycline antibiotics by the various spectroscopies.
2. 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.
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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 ╳
