Bhimamycin A
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| Category | Antibiotics |
| Catalog number | BBF-00142 |
| CAS | |
| Molecular Weight | 272.25 |
| Molecular Formula | C15H12O5 |
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Description
Bhimamycin is an antibiotic produced by Streptomyces sp. GW32/698. Five components A to E are separated. Bhimamycin A has moderate activity against gram-positive and gram-negative bacteria.
Specification
| IUPAC Name | 5-hydroxy-1-(1-hydroxyethyl)-3-methylbenzo[f][2]benzofuran-4,9-dione |
| Canonical SMILES | CC1=C2C(=C(O1)C(C)O)C(=O)C3=C(C2=O)C(=CC=C3)O |
| InChI | InChI=1S/C15H12O5/c1-6(16)15-12-10(7(2)20-15)14(19)11-8(13(12)18)4-3-5-9(11)17/h3-6,16-17H,1-2H3 |
| InChI Key | VIBRJPNFOAVLAA-UHFFFAOYSA-N |
Properties
| Appearance | Brown Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
Reference Reading
1. New bhimamycins from Streptomyces sp. AK 671
Philipp Jetter, Claudia Steinert, Michael Knauer, Guoliang Zhang, Torsten Bruhn, Jutta Wiese, Johannes F Imhoff, Hans-Peter Fiedler, Gerhard Bringmann J Antibiot (Tokyo). 2013 Dec;66(12):719-26. doi: 10.1038/ja.2013.82. Epub 2013 Sep 18.
From the wild-type strain Steptomyces sp. AK 671, three nitrogen-containing octaketides were isolated, bhimamycins F, H and I, besides the known azaanthraquinone utahmycin A and polyketide shunt products SEK 4, SEK 4b, mutactin, dehydromutactin and EM18. The structures were characterized by MS and NMR experiments. The hitherto unknown absolute configuration of the two enantiomers of EM18 was determined by online-CD spectroscopy and quantum-chemical CD calculations. Bhimamycins H and I show weak antibacterial activities, whereas the enzyme phosphodiesterase 4 is strongly inhibited by bhimamycins H and I, which has never been reported for nitrogen-containing octaketides. In addition, bhimamycin H inhibits the enzyme glycogen synthase kinase-3β.
2. Bhimamycin A to approximately E and bhimanone: isolation, structure elucidation and biological activity of novel quinone antibiotics from a terrestrial Streptomycete
Serge Fotso, Rajendra P Maskey, Iris Grün-Wollny, Klaus-Peter Schulz, Morton Munk, Hartmut Laatsch J Antibiot (Tokyo). 2003 Nov;56(11):931-41. doi: 10.7164/antibiotics.56.931.
From the ethyl acetate extract of a terrestrial Streptomycete isolate, five new quinone antibiotics, bhimamycin A (2a), B (2b), C (3c), D (5a), E (7) and the new tetralone bhimanone (8) were isolated together with the known microbial products chrysophanol (1a), aloesaponarin II (1b), 3,8-dihydroxy-1-methylanthraquinone-2-carboxylic acid (1c), adenosine, 2'-deoxyadenosine, phenylacetamide, and 2-(p-hydroxyphenyl)ethanol. The structures of these natural products were deduced from the spectral data and confirmed by comparison with related compounds from the literature and by synthesis.
3. Bhimamycin J, a Rare Benzo[f]isoindole-dione Alkaloid from the Marine-Derived Actinomycete Streptomyces sp. MS180069
Fuhang Song, Na Yang, Zeinab G Khalil, Angela A Salim, Jiahui Han, Paul V Bernhardt, Rui Lin, Xiuli Xu, Robert J Capon Chem Biodivers. 2021 Nov;18(11):e2100674. doi: 10.1002/cbdv.202100674. Epub 2021 Oct 27.
Chemical investigation on a Streptomyces sp. strain MS180069 isolated from a sediment sample collected from the South China Sea, yielded the new benzo[f]isoindole-dione alkaloid, bhimamycin J (1). The structure was determined by extensive spectroscopic analysis, including HRMS, 1D, 2D NMR, and X-ray diffraction techniques. A molecular docking study revealed 1 as a new molecular motif that binds with human angiotensin converting enzyme2 (ACE2), recently described as the cell surface receptor responsible for uptake of 2019-CoV-2. Using enzyme assays we confirm that 1 inhibits human ACE2 79.7 % at 25 μg/mL.
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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 ╳
