Griseorhodin A
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| Category | Antibiotics |
| Catalog number | BBF-01290 |
| CAS | 11048-91-2 |
| Molecular Weight | 508.39 |
| Molecular Formula | C25H16O12 |
| Purity | 99% |
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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 bacterial activity.
Specification
| Synonyms | 1'a,9'b-Dihydro-3,4,4',9-tetrahydroxy-7-methoxy-7'-methylspiro[naphtho[2,3-b]furan-2(3H),2'(5'H)-oxireno[d]benzo[1,2-b:5,4-c']dipyran]-5,5',8-trione |
| IUPAC Name | 2',3,4,9-tetrahydroxy-7-methoxy-6'-methylspiro[3H-benzo[f][1]benzofuran-2,14'-5,12,15-trioxatetracyclo[8.5.0.03,8.011,13]pentadeca-1(10),2,6,8-tetraene]-4',5,8-trione |
| Canonical SMILES | CC1=CC2=CC3=C(C(=C2C(=O)O1)O)OC4(C5C3O5)C(C6=C(C7=C(C(=C6O4)O)C(=O)C(=CC7=O)OC)O)O |
| InChI | InChI=1S/C25H16O12/c1-6-3-7-4-8-19(17(29)11(7)24(32)34-6)36-25(23-20(8)35-23)22(31)14-16(28)12-9(26)5-10(33-2)15(27)13(12)18(30)21(14)37-25/h3-5,20,22-23,28-31H,1-2H3 |
| InChI Key | MRNNMFMPNANLHB-UHFFFAOYSA-N |
Properties
| Appearance | Red Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 803.0 °C at 760 mmHg |
| Melting Point | 282-283 °C |
| Density | 1.77 g/cm3 |
| Solubility | Soluble in DMF; Slightly soluble in Alcohol, Acetone, Chloroform, Benzene, sodium bicarbonate solution; Insoluble in Water, Ether |
Reference Reading
1. A comparative metabologenomic approach reveals mechanistic insights into Streptomyces antibiotic crypticity
Yunci Qi, Keshav K Nepal, Joshua A V Blodgett Proc Natl Acad Sci U S A. 2021 Aug 3;118(31):e2103515118. doi: 10.1073/pnas.2103515118.
Streptomyces genomes harbor numerous, biosynthetic gene clusters (BGCs) encoding for drug-like compounds. While some of these BGCs readily yield expected products, many do not. Biosynthetic crypticity represents a significant hurdle to drug discovery, and the biological mechanisms that underpin it remain poorly understood. Polycyclic tetramate macrolactam (PTM) antibiotic production is widespread within the Streptomyces genus, and examples of active and cryptic PTM BGCs are known. To reveal further insights into the causes of biosynthetic crypticity, we employed a PTM-targeted comparative metabologenomics approach to analyze a panel of S. griseus clade strains that included both poor and robust PTM producers. By comparing the genomes and PTM production profiles of these strains, we systematically mapped the PTM promoter architecture within the group, revealed that these promoters are directly activated via the global regulator AdpA, and discovered that small promoter insertion-deletion lesions (indels) differentiate weaker PTM producers from stronger ones. We also revealed an unexpected link between robust PTM expression and griseorhodin pigment coproduction, with weaker S. griseus-clade PTM producers being unable to produce the latter compound. This study highlights promoter indels and biosynthetic interactions as important, genetically encoded factors that impact BGC outputs, providing mechanistic insights that will undoubtedly extend to other Streptomyces BGCs. We highlight comparative metabologenomics as a powerful approach to expose genomic features that differentiate strong, antibiotic producers from weaker ones. This should prove useful for rational discovery efforts and is orthogonal to current engineering and molecular signaling approaches now standard in the field.
2. An acetyltransferase controls the metabolic flux in rubromycin polyketide biosynthesis by direct modulation of redox tailoring enzymes
Marina Toplak, Adelheid Nagel, Britta Frensch, Thorsten Lechtenberg, Robin Teufel Chem Sci. 2022 May 17;13(24):7157-7164. doi: 10.1039/d2sc01952c. eCollection 2022 Jun 22.
The often complex control of bacterial natural product biosynthesis typically involves global and pathway-specific transcriptional regulators of gene expression, which often limits the yield of bioactive compounds under laboratory conditions. However, little is known about regulation mechanisms on the enzymatic level. Here, we report a novel regulatory principle for natural products involving a dedicated acetyltransferase, which modifies a redox-tailoring enzyme and thereby enables pathway furcation and alternating pharmacophore assembly in rubromycin polyketide biosynthesis. The rubromycins such as griseorhodin (grh) A are complex bioactive aromatic polyketides from Actinobacteria with a hallmark bisbenzannulated [5,6]-spiroketal pharmacophore that is mainly installed by two flavoprotein monooxygenases. First, GrhO5 converts the advanced precursor collinone into the [6,6]-spiroketal containing dihydrolenticulone, before GrhO6 effectuates a ring contraction to afford the [5,6]-spiroketal. Our results show that pharmacophore assembly in addition involves the acetyl-CoA-dependent acetyltransferase GrhJ that activates GrhO6 to allow the rapid generation and release of its labile product, which is subsequently sequestered by ketoreductase GrhO10 and converted into a stable intermediate. Consequently, the biosynthesis is directed to the generation of canonical rubromycins, while the alternative spontaneous [5,6]-spiroketal hydrolysis to a ring-opened pathway product is thwarted. Presumably, this allows the bacteria to rapidly adjust the biosynthesis of functionally distinct secondary metabolites depending on nutrient and precursor (i.e. acetyl-CoA) availability. Our study thus illustrates how natural product biosynthesis can be enzymatically regulated and provides new perspectives for the improvement of in vitro enzyme activities and natural product titers via biotechnological approaches.
3. 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.
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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 ╳
