A bacterial metabolite
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β-Rubromycin

Item No. 27477

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(2S)-4,4',9,9'-tetrahydro-8',10-dihydroxy-5',7'-dimethoxy-4',9,9'-trioxo-spiro[benzo[1,2-b:5,4-c']dipyran-2(3H),2'(3'H)-naphtho[2,3-b]furan]-7-carboxylic acid, methyl ester
CAS Number
27267-70-5
Molecular Formula
C27H20O12
Formula Weight
536.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 1 mg/ml
SMILES
O=C(OC)C(O1)=CC(C=C(CC[C@@]2(OC(C(C(C(O)=C(OC)C=C3OC)=C3C4=O)=O)=C4C2)O5)C5=C6O)=C6C1=O
InChi Code
InChI=1S/C27H20O12/c1-34-13-8-14(35-2)20(29)18-17(13)19(28)12-9-27(39-24(12)22(18)31)5-4-10-6-11-7-15(25(32)36-3)37-26(33)16(11)21(30)23(10)38-27/h6-8,29-30H,4-5,9H2,1-3H3/t27-/m0/s1
InChi Key
FXCBZGHGMRSWJD-MHZLTWQESA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    β-Rubromycin is a bacterial metabolite originally isolated from Streptomyces that has diverse biological activities.1 It inhibits the growth of HMO2, KATO-III, and MCF-7 cells with GI50 values of 0.5, 0.84, and <0.1 μM, respectively. β-rubromycin inhibits HIV-1 reverse transcriptase activity by 39.7% when used at a concentration of 10 μM. It also has antibacterial activity against Gram-positive bacteria. The structure of β-rubromycin was originally described as containing an ortho-quinone group, but it was revised to a para-quinone group in 2000 using organic and biosynthetic methods, as well as spectroscopic analysis.1,2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ueno, T., Takahashi, H., Oda, M., et al. Inhibition of human telomerase by rubromycins: Implication of spiroketal system of the compounds as an active moiety. Biochemistry 39(20), 5995-6002 (2000).

    2. Puder, C., Loya, S., Hizi, A., et al. Structural and biosynthetic investigations of the rubromycins. Eur. J. Org. Chem. 2000(5), 729-735 (2000).

    3. Goldman, M.E., Salituro, G.S., Bowen, J.A., et al. Inhibition of human immunodeficiency virus-1 reverse transcriptase activity by rubromycins: Competitive interaction at the template.primer site. Mol. Pharmacol. 38(1), 20-25 (1990).