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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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