Griseorhodin G
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| Category | Antibiotics |
| Catalog number | BBF-01292 |
| CAS | |
| Molecular Weight | 510.40 |
| Molecular Formula | C25H18O12 |
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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 has antitumor activity.
Specification
| Synonyms | NSC289645; FCRC57-G; FCRC-57-G |
| IUPAC Name | 3,3',4',9',10-pentahydroxy-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(C3)O)C(C5=C(C6=C(C(=C5O4)O)C(=O)C(=CC6=O)OC)O)O |
| InChI | InChI=1S/C25H18O12/c1-7-3-8-4-9-5-12(27)25(36-21(9)19(30)13(8)24(33)35-7)23(32)16-18(29)14-10(26)6-11(34-2)17(28)15(14)20(31)22(16)37-25/h3-4,6,12,23,27,29-32H,5H2,1-2H3 |
| InChI Key | NWVQGFXTZWXNGL-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Melting Point | 270 -274 °C (dec.) |
| Solubility | Soluble in DMF; Slightly soluble in Alcohol, Acetone, Chloroform, Benzene, sodium bicarbonate solution; Insoluble in Water, Ether |
Reference Reading
1. 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.
2. Isolation and structure elucidation of a novel griseorhodin
R M Stroshane, J A Chan, E A Rubalcaba, A L Garretson, A A Aszalos, P P Roller J Antibiot (Tokyo). 1979 Mar;32(3):197-204. doi: 10.7164/antibiotics.32.197.
Three antibiotics possessing cytotoxic properties were isolated from a strain of Streptomyces griseus (FCRC-57). One was found to be identical with griseorhodin A. A second, FCRC-57-U, was found to be identical to griseorhodin C. FCRC-57-G is a new antibiotic structurally related to griseorhodins A and C, and is active against KB cells in vitro. The structure of this new antibiotic was determined using mass spectrometry, proton and carbon nuclear magnetic resonance spectroscopy and synthesis.
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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 ╳
