Granatomycin B
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| Category | Antibiotics |
| Catalog number | BBF-01280 |
| CAS | 71203-18-4 |
| Molecular Weight | 476.43 |
| Molecular Formula | C23H24O11 |
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Description
It is produced by the strain of Streptomyces lateritius (ZIMET 43646). It's a quinone antibiotic. It has anti-gram positive bacteria and negative bacteria activity.
Specification
| Synonyms | Granaticin methyl ester; (1R,13R)-1,3,4,6,7,9,10,11-Octahydro-4α,5,10β,12,13-pentahydroxy-3α,7α-dimethyl-6,11-dioxo-1β,4-ethanonaphtho[2,3-c:6,7-c']dipyran-9β-acetic acid methyl ester; (1R,13R)-3,4,9,10-Tetrahydro-4α,5,10β,12,13-pentahydroxy-9β-(methoxycarbonylmethyl)-3α,7α-dimethyl-1β,4-ethanonaphtho[2,3-c:6,7-c']dipyran-6,11(1H,7H)-dione; 10-Hydroxygranatomycin methyl ester; Methylgranaticin |
| IUPAC Name | methyl 2-[(1S,7S,9S,10S,16R,18R,19R)-1,3,10,14,19-pentahydroxy-7,18-dimethyl-5,12-dioxo-8,17-dioxapentacyclo[14.2.2.02,15.04,13.06,11]icosa-2(15),3,6(11),13-tetraen-9-yl]acetate |
| Canonical SMILES | CC1C2=C(C(C(O1)CC(=O)OC)O)C(=O)C3=C(C4=C(C(=C3C2=O)O)C5(C(OC4CC5O)C)O)O |
| InChI | InChI=1S/C23H24O11/c1-6-12-14(18(26)9(33-6)5-11(25)32-3)21(29)15-16(19(12)27)22(30)17-13(20(15)28)8-4-10(24)23(17,31)7(2)34-8/h6-10,18,24,26,28,30-31H,4-5H2,1-3H3/t6-,7+,8+,9-,10+,18+,23+/m0/s1 |
| InChI Key | ZVIFBNVTKYPKQO-VDUSGPLOSA-N |
Properties
| Appearance | Red Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 717.2±60.0 °C (Predicted) |
| Density | 1.68±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Identification of secondary metabolites from Streptomyces violaceoruber TU22 by means of on-flow LC-NMR and LC-DAD-MS
L H Pham, J Vater, W Rotard, C Mügge Magn Reson Chem. 2005 Sep;43(9):710-23. doi: 10.1002/mrc.1633.
For rapid screening of natural products from Actinomycetes, a combination of on-line couplings LC-NMR, LC-DAD-MS and HPLC-PDA, as well as MALDI-TOF-MS is particularly suitable. Simultaneous use of these coupling techniques provides considerable advantages for the rapid identification of natural compounds in mixtures. The results of our present investigation on secondary metabolite products of Streptomyces violaceoruber TU 22 showed that more than 50% of the identified metabolites are new compounds. The structures of four new polyketides (granaticin C, metenaticin A, B and C) as well as four known ones (granaticin A, granatomycin E, daidzein and genistein) have been elucidated using LC-NMR, LC-MS/MS and -MS(n) techniques in combination with two-dimensional NMR spectroscopy.
2. Upregulation and Identification of Antibiotic Activity of a Marine-Derived Streptomyces sp. via Co-Cultures with Human Pathogens
Anne A Sung, Samantha M Gromek, Marcy J Balunas Mar Drugs. 2017 Aug 11;15(8):250. doi: 10.3390/md15080250.
Marine natural product drug discovery has begun to play an important role in the treatment of disease, with several recently approved drugs. In addition, numerous microbial natural products have been discovered from members of the order Actinomycetales, particularly in the genus Streptomyces, due to their metabolic diversity for production of biologically active secondary metabolites. However, many secondary metabolites cannot be produced under laboratory conditions because growth conditions in flask culture differ from conditions in the natural environment. Various experimental conditions (e.g., mixed fermentation) have been attempted to increase yields of previously described metabolites, cause production of previously undetected metabolites, and increase antibiotic activity. Adult ascidians-also known as tunicates-are sessile marine invertebrates, making them vulnerable to predation and therefore are hypothesized to use host-associated bacteria that produce biologically active secondary metabolites for chemical defense. A marine-derived Streptomyces sp. strain PTY087I2 was isolated from a Panamanian tunicate and subsequently co-cultured with human pathogens including Bacillus subtilis, methicillin-sensitive Staphylococcus aureus (MSSA), methicillin-resistant Staphylococcus aureus (MRSA), and Pseudomonas aeruginosa, followed by extraction. Co-culture of Streptomyces sp. PTY087I2 with each of these human pathogens resulted in increased production of three antibiotics: granaticin, granatomycin D, and dihydrogranaticin B, as well as several analogues seen via molecular networking. In addition, co-cultures resulted in strongly enhanced biological activity against the Gram positive human pathogens used in these experiments. Expanded utilization of co-culture experiments to allow for competitive interactions may enhance metabolite production and further our understanding of these microbial interactions.
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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 ╳
