γ-Rubromycin
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| Category | Antibiotics |
| Catalog number | BBF-02215 |
| CAS | 27267-71-6 |
| Molecular Weight | 522.41 |
| Molecular Formula | C26H18O12 |
| Purity | ≥98% |
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Description
γ-Rubromycin is a quinone antibiotic originally isolated from Streptomyces. It is effective against Gram-positive bacteria.
Specification
| Synonyms | (S)-4,4',9,9'-Tetrahydro-5',8',10-trihydroxy-7'-methoxy-4',9',9-trioxospiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid methyl ester |
| Storage | Store at -20°C |
| IUPAC Name | methyl (2S)-4',9',10-trihydroxy-7'-methoxy-5',8',9-trioxospiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-7-carboxylate; gamma-Rubromycin |
| Canonical SMILES | COC1=CC(=O)C2=C(C1=O)C(=C3C(=C2O)CC4(O3)CCC5=C(O4)C(=C6C(=C5)C=C(OC6=O)C(=O)OC)O)O |
| InChI | InChI=1S/C26H18O12/c1-34-13-7-12(27)16-17(19(13)29)21(31)23-11(18(16)28)8-26(38-23)4-3-9-5-10-6-14(24(32)35-2)36-25(33)15(10)20(30)22(9)37-26/h5-7,28,30-31H,3-4,8H2,1-2H3/t26-/m0/s1 |
| InChI Key | CKLKRRFSZZUFKT-SANMLTNESA-N |
Properties
| Appearance | Red Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 909.32°C at 760 mmHg |
| Melting Point | 235°C |
| Density | 1.77 g/cm3 |
| Solubility | Soluble in methanol, DMSO, and dichloromethane. |
Reference Reading
1. Isolation, biological activity, biosynthesis and synthetic studies towards the rubromycin family of natural products
Darcy J Atkinson, Margaret A Brimble Nat Prod Rep. 2015 Jun;32(6):811-40. doi: 10.1039/c4np00153b.
The rubromycins are an ever growing family of natural products isolated from various Actinomycetes over the last 60 years. Exhibiting a highly attractive array of antimicrobial and enzyme activity, this unique family of compounds have attracted significant attention from many synthetic chemists. Investigations into the synthesis of the densely functionalised hexacyclic ring system have revealed many hidden synthetic challenges. This review covers the isolation, the reported biological activity and the detailed synthetic studies towards these complex natural products.
2. Model Reactions for the Enantioselective Synthesis of γ-Rubromycin: Stereospecific Intramolecular Photoredox Cyclization of an ortho-Quinone Ether to a Spiroacetal
Fumihiro Wakita, Yoshio Ando, Ken Ohmori, Keisuke Suzuki Org Lett. 2018 Jul 6;20(13):3928-3932. doi: 10.1021/acs.orglett.8b01475. Epub 2018 Jun 22.
A model study for the enantioselective total synthesis of γ-rubromycin has revealed a promising approach for constructing the chiral, nonracemic bicyclic spiroacetal via the stereospecific photoredox reaction of 1,2-naphthoquinone ether.
3. Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces
Xiachang Wang, Sherif I Elshahawi, Larissa V Ponomareva, Qing Ye, Yang Liu, Gregory C Copley, James C Hower, Bruce E Hatcher, Madan K Kharel, Steven G Van Lanen, Qing-Bai She, S Randal Voss, Jon S Thorson, Khaled A Shaaban J Nat Prod. 2019 Dec 27;82(12):3469-3476. doi: 10.1021/acs.jnatprod.9b01015. Epub 2019 Dec 13.
We report the isolation and characterization of three new nybomycins (nybomycins B-D, 1-3) and six known compounds (nybomycin, 4; deoxynyboquinone, 5; α-rubromycin, 6; β-rubromycin, 7; γ-rubromycin, 8; and [2α(1E,3E),4β]-2-(1,3-pentadienyl)-4-piperidinol, 9) from the Rock Creek (McCreary County, KY) underground coal mine acid reclamation site isolate Streptomyces sp. AD-3-6. Nybomycin D (3) and deoxynyboquinone (5) displayed moderate (3) to potent (5) cancer cell line cytotoxicity and displayed weak to moderate anti-Gram-(+) bacterial activity, whereas rubromycins 6-8 displayed little to no cancer cell line cytotoxicity but moderate to potent anti-Gram-(+) bacterial and antifungal activity. Assessment of the impact of 3 or 5 cancer cell line treatment on 4E-BP1 phosphorylation, a predictive marker of ROS-mediated control of cap-dependent translation, also revealed deoxynyboquinone (5)-mediated downstream inhibition of 4E-BP1p. Evaluation of 1-9 in a recently established axolotl embryo tail regeneration assay also highlighted the prototypical telomerase inhibitor γ-rubromycin (8) as a new inhibitor of tail regeneration. Cumulatively, this work highlights an alternative nybomycin production strain, a small set of new nybomycin metabolites, and previously unknown functions of rubromycins (antifungal activity and inhibition of tail regeneration) and also provides a basis for revision of the previously proposed nybomycin biosynthetic pathway.
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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 ╳
