Bagremycin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00262 |
| CAS | |
| Molecular Weight | 255.27 |
| Molecular Formula | C15H13NO3 |
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Description
It is produced by the strain of Streptomyces sp. Tu 4128. Bagremycin A has weak activity against gram-positive bacteria, Saccharomyces cerevisiae and Candida albicans.
Specification
| Synonyms | CHEMBL4125959 |
| IUPAC Name | (4-ethenylphenyl) 3-amino-4-hydroxybenzoate |
| Canonical SMILES | C=CC1=CC=C(C=C1)OC(=O)C2=CC(=C(C=C2)O)N |
| InChI | InChI=1S/C15H13NO3/c1-2-10-3-6-12(7-4-10)19-15(18)11-5-8-14(17)13(16)9-11/h2-9,17H,1,16H2 |
| InChI Key | RWDKQKLCXJVELF-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | gram-positive bacteria; fungi |
| Melting Point | 176 °C |
Reference Reading
1. Rare actinomycetes Nocardia caishijiensis and Pseudonocardia carboxydivorans as endophytes, their bioactivity and metabolites evaluation
Rabia Tanvir, Imran Sajid, Shahida Hasnain, Andreas Kulik, Stephanie Grond Microbiol Res. 2016 Apr;185:22-35. doi: 10.1016/j.micres.2016.01.003. Epub 2016 Jan 23.
Two strains identified as Nocardia caishijiensis (SORS 64b) and Pseudonocardia carboxydivorans (AGLS 2) were isolated as endophytes from Sonchus oleraceus and Ageratum conyzoides respectively. The analysis of their extracts revealed them to be strongly bioactive. The N. caishijiensis extract gave an LC50 of 570 μg/ml(-1) in the brine shrimp cytotoxicity assay and an EC50 of 0.552 μg/ml(-1) in the DPPH antioxidant assay. Antimicrobial activity was observed against Methicillin resistant Staphlococcus aureus (MRSA) and Escherichia coli ATCC 25922 (14 mm), Klebsiella pneumoniae ATCC 706003 (13 mm), S. aureus ATCC 25923 (11 mm) and Candida tropicalis (20 mm). For the extract of P. carboxydivorans the EC50 was 0.670 μg/ml(-1) and it was observed to be more bioactive against Bacillus subtilis DSM 10 ATCC 6051 (21 mm), C. tropicalis (20 mm), S. aureus ATCC 25923 (17 mm), MRSA (17 mm), E. coli K12 (W1130) (16 mm) and Chlorella vulgaris (10 mm). The genotoxicity testing revealed a 20 mm zone of inhibition against the polA mutant strain E. coli K-12 AB 3027 suggesting damage to the DNA and polA genes. The TLC and bioautography screening revealed a diversity of active bands of medium polar and nonpolar compounds. Metabolite analysis by HPLC-DAD via UV/vis spectral screening suggested the possibility of stenothricin and bagremycin A in the mycelium extract of N. caishijiensis respectively. In the broth and mycelium extract of P. carboxydivorans borrelidin was suggested along with α-pyrone. The HPLC-MS revealed bioactive long chained amide derivatives such as 7-Octadecenamide, 9, 12 octadecandienamide. This study reports the rare actinomycetes N. caishijiensis and P. carboxydivorans as endophytes and evaluates their bioactive metabolites.
2. Cytotoxic Bagremycins from Mangrove-Derived Streptomyces sp. Q22
Lei Chen, Weiyun Chai, Wenling Wang, Tengfei Song, Xiao-Yuan Lian, Zhizhen Zhang J Nat Prod. 2017 May 26;80(5):1450-1456. doi: 10.1021/acs.jnatprod.6b01136. Epub 2017 May 15.
New bagremycins C-E (3-5) and bagrelactone A (6), together with known bagremycins A (1) and B (2), 4-hydroxystyrene (7), and 4-hydroxystyrene 4-O-α-d-galactopyranoside (8), were isolated from a mangrove-derived actinomycete, Streptomyces sp. Q22. Structures of these new compounds were elucidated based on their NMR and HRESIMS spectroscopic data as well as chemical degradation. Bagremycin C (3) is a unique analogue with an N-acetyl-(S)-cysteine moiety, while bagrelactone A (6) represents the first example of this type of bagremycin-derived macrolide. Bagremycin C (3) was active against four glioma cell lines, with IC50 values in the range from 2.2 to 6.4 μM, induced apoptosis in human glioma U87MG cells in a dose- and time-dependent manner, and arrested the U87MG cell cycle at the G0/G1 phase.
3. Characterization of the bagremycin biosynthetic gene cluster in Streptomyces sp. Tü 4128
Jiang Ye, Yunxia Zhu, Bingbing Hou, Haizhen Wu, Huizhan Zhang Biosci Biotechnol Biochem. 2019 Mar;83(3):482-489. doi: 10.1080/09168451.2018.1553605. Epub 2018 Dec 10.
Bagremycin A and bagremycin B isolated from Streptomyces sp. Tü 4128 have activities against Gram-positive bacteria, fungi and also have a weak antitumor activity, which make them have great potential for development of novel antibiotics. Here, we report a draft genome 8,424,112 bp in length of S. sp. Tü 4128 by Illumina Hiseq2000, and identify the bagremycins biosynthetic gene cluster (BGC) by bioinformatics analysis. The putative bagremycins BGC includes 16 open reading frames (ORFs) with the functions of biosynthesis, resistance and regulation. Disruptions of relative genes and HPLC analysis of bagremycins production demonstrated that not all the genes within the BGC are responsible for the biosynthesis of bagremycins. In addition, the biosynthetic pathways of bagremycins are proposed for deeper inquiries into their intriguing biosynthetic mechanism.
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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 ╳
