Griseorhodin C
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| Category | Antibiotics |
| Catalog number | BBF-01291 |
| CAS | |
| Molecular Weight | 526.40 |
| Molecular Formula | C25H18O13 |
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Description
It is produced by the strain of Streptomyces californicus JA-2640 and Str. griseus (FCRC-57). It is a quinone antibiotic. It mainly has anti-gram-positive bacteria and negative bacteria (individual) activity.
Specification
| IUPAC Name | 3,3',4,4',9',10-hexahydroxy-7'-methoxy-7-methylspiro[3,4-dihydropyrano[4,3-g]chromene-2,2'-3H-benzo[f][1]benzofuran]-5',8',9-trione |
| Canonical SMILES | CC1=CC2=CC3=C(C(=C2C(=O)O1)O)OC4(C(C3O)O)C(C5=C(C6=C(C(=C5O4)O)C(=O)C(=CC6=O)OC)O)O |
| InChI | InChI=1S/C25H18O13/c1-6-3-7-4-8-15(27)23(33)25(37-20(8)18(30)11(7)24(34)36-6)22(32)14-17(29)12-9(26)5-10(35-2)16(28)13(12)19(31)21(14)38-25/h3-5,15,22-23,27,29-33H,1-2H3 |
| InChI Key | DGMDECJODXVYFT-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Solubility | Soluble in DMF; Slightly soluble in Alcohol, Acetone, Chloroform, Benzene, sodium bicarbonate solution; Insoluble in Water, Ether |
Reference Reading
1. Inhibition of human telomerase by rubromycins: implication of spiroketal system of the compounds as an active moiety
T Ueno, H Takahashi, M Oda, M Mizunuma, A Yokoyama, Y Goto, Y Mizushina, K Sakaguchi, H Hayashi Biochemistry. 2000 May 23;39(20):5995-6002. doi: 10.1021/bi992661i.
We found that a group of rubromycins and their analogues, a class of quinone antibiotics that possesses benzofuran and benzodipyran rings to form a spiroketal system, strongly inhibited human telomerase as assessed with a modified telomeric repeat amplification protocol. beta- and gamma-Rubromycins and purpuromycin appeared to be the most potent telomerase inhibitors, with 50% inhibitory concentrations (IC(50)) of about 3 microM, and griseorhodins A and C also showed comparable potencies for the inhibition (IC(50) = 6-12 microM). In contrast, opening of the spiroketal system of beta-rubromycin, giving rise to alpha-rubromycin, substantially decreased its inhibitory potency toward telomerase (IC(50) > 200 microM), indicating the essential role of the spiroketal system in telomerase inhibition. A kinetic study of the inhibition by beta-rubromycin revealed a competitive interaction with respect to the telomerase substrate primer, with a K(i) of 0.74 microM, whereas a mixed type inhibition was observed with respect to the nucleotide substrate. beta-Rubromycin was also potent in inhibiting retroviral reverse transcriptases but had virtually no effect on other DNA/RNA-modifying enzymes including DNA and RNA polymerases, deoxyribonuclease, and topoisomerase. Although beta-rubromycin showed nonspecific cytotoxicities, reducing proliferation of cancer cells (IC(50) approximately 20 microM), we conclude that beta-rubromycin appears to be a lead structure for the development of more potent and selective inhibitors of human telomerase.
2. Absolute Configurations of Griseorhodins A and C
Humberto E Ortega, João M Batista Jr, Weilan G P Melo, Jon Clardy, Mônica T Pupo Tetrahedron Lett. 2017 Dec 13;58(50):4721-4723. doi: 10.1016/j.tetlet.2017.11.008. Epub 2017 Nov 7.
The known antibiotic and cytotoxic compounds griseorhodin A (1) and griseorhodin C (2) were produced in solid culture by Streptomyces puniceus AB10, which was isolated from the leaf-cutter ant Acromyrmex rugosus rugosus. Their absolute configurations were unambiguously established as 6S,6aR,7S,8S and 6R,6aR,7S,8R, respectively, using vibrational circular dichroism (VCD) and density functional theory (DFT) calculations.
3. Biosynthesis of pentangular polyphenols: deductions from the benastatin and griseorhodin pathways
Gerald Lackner, Angéla Schenk, Zhongli Xu, Kathrin Reinhardt, Zeynep S Yunt, Jörn Piel, Christian Hertweck J Am Chem Soc. 2007 Aug 1;129(30):9306-12. doi: 10.1021/ja0718624. Epub 2007 Jul 11.
The benastatins, pradimicins, fredericamycins, and members of the griseorhodin/rubromycin family represent a structurally and functionally diverse group of long-chain polyphenols from actinomycetes. Comparison of their biosynthetic gene clusters (ben, prm, fdm, grh, rub) revealed that all loci harbor genes coding for a similar, yet uncharacterized, type of ketoreductases. In a phylogenetic survey of representative KRs involved in type II PKS systems, we found that it is generally possible to deduce the KR regiospecificity (C-9, C-15, C17) from the amino acid sequence and thus to predict the nature of the aromatic polyketide (e.g., angucycline, anthracycline, benzoisochromanequinones). We hypothezised that the new clade of KRs is characteristic for biosynthesis of polyphenols with an extended angular architecture we termed "pentangular". To test this hypothesis, we demonstrated the biogenetic relationship between benastatin and the structurally unrelated spiro ketal griseorhodin by generating a mutant producing collinone, a pentangular pathway intermediate. The benastatin pathway served as a model to characterize the KR. Gene inactivation of benL resulted in the formation of a series of 19-hydroxy benastatin and bequinostatin derivatives (e.g., benastatin K and benastatin L). These results clearly showed that BenL functions as a C-19 KR in pentangular pathways.
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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 ╳
