Fusarubin
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| Category | Others |
| Catalog number | BBF-01860 |
| CAS | 1702-77-8 |
| Molecular Weight | 306.27 |
| Molecular Formula | C15H14O7 |
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Description
Fusarubin is a metabolite of Fusarium solani.
Specification
| Synonyms | Oxyjavanicin; NSC106193; 1H-Naphtho[2,3-c]pyran-5,10-dione, 3,4-dihydro-3,6,9-trihydroxy-7-methoxy-3-methyl- |
| IUPAC Name | 3,5,10-trihydroxy-7-methoxy-3-methyl-1,4-dihydrobenzo[g]isochromene-6,9-dione |
| Canonical SMILES | CC1(CC2=C(CO1)C(=C3C(=O)C=C(C(=O)C3=C2O)OC)O)O |
| InChI | InChI=1S/C15H14O7/c1-15(20)4-6-7(5-22-15)13(18)10-8(16)3-9(21-2)14(19)11(10)12(6)17/h3,17-18,20H,4-5H2,1-2H3 |
| InChI Key | FKJXMYJPOKQPSS-UHFFFAOYSA-N |
Properties
| Appearance | Red Flake Crystalline |
| Boiling Point | 663.7°Cat760 mmHg |
| Melting Point | 218°C |
| Density | 1.61 g/cm3 |
| Solubility | Soluble in Acetone, Tetrahydrofuran, Dioxane, Pyridine |
Reference Reading
1. Heterologous Expression of the Core Genes in the Complex Fusarubin Gene Cluster of Fusarium Solani
Tobias Bruun Pedersen, Mikkel Rank Nielsen, Sebastian Birkedal Kristensen, Eva Mie Lang Spedtsberg, Wafaa Yasmine, Rikke Matthiesen, Samba Evelyne Kabemba Kaniki, Trine Sørensen, Celine Petersen, Jens Muff, Teis Esben Sondergaard, Kåre Lehmann Nielsen, Reinhard Wimmer, Jens Laurids Sørensen Int J Mol Sci. 2020 Oct 14;21(20):7601. doi: 10.3390/ijms21207601.
Through stepwise recreation of the biosynthetic gene cluster containing PKS3 from Fusarium solani, it was possible to produce the core scaffold compound of bostrycoidin, a red aza-anthraquinone pigment in Saccharomyces cerevisiae. This was achieved through sequential transformation associated recombination (TAR) cloning of FvPPT, fsr1, fsr2, and fsr3 into the pESC-vector system, utilizing the inducible bidirectional galactose promoter for heterologous expression in S. cerevisiae. The production of the core metabolite bostrycoidin was investigated through triplicate growth cultures for 1-4 days, where the maximum titer of bostrycoidin was achieved after 2 days of induction, yielding 2.2 mg/L.
2. Unified synthesis and cytotoxic activity of 8-O-methylfusarubin and its analogues
Pongsit Vijitphan, Vatcharin Rukachaisirikul, Chatchai Muanprasat, Panata Iawsipo, Jiraporn Panprasert, Kwanruthai Tadpetch Org Biomol Chem. 2019 Aug 7;17(29):7078-7087. doi: 10.1039/c9ob01221d. Epub 2019 Jul 12.
A simple and unified synthesis of four related pyranonaphthoquinone natural products, e.g. 8-O-methylfusarubin, 8-O-methylanhydrofusarubin, fusarubin and anhydrofusarubin, is reported. The key synthetic features include the precedented Diels-Alder cycloaddition to assemble the naphthalene skeleton, selective formylation and acetonylation and intramolecular acetalization to construct the pyran ring. Manipulation of the oxidation state of the naphthoquinone core was performed to construct the two analogues, fusarubin and anhydrofusarubin. This work also highlights an unprecedented directing effect of the hydroxymethylene group in the selective hypervalent iodine-mediated quinone oxidation. The four synthetic compounds were evaluated for their in vitro cytotoxic activities against six human cancer cells. 8-O-Methylfusarubin was the most potent analogue and displayed excellent cytotoxic activity against MCF-7 breast cancer cells with an IC50 value of 1.01 μM with no cytotoxic effect on noncancerous Vero cells, which could potentially be a promising lead compound for anti-breast cancer drug discovery.
3. Fusarubin and Anhydrofusarubin Isolated from A Cladosporium Species Inhibit Cell Growth in Human Cancer Cell Lines
Sabrina Adorisio, Alessandra Fierabracci, Isabella Muscari, Anna Marina Liberati, Lorenza Cannarile, Trinh Thi Thuy, Tran Van Sung, Hossain Sohrab, Choudhury Mahmood Hasan, Emira Ayroldi, Carlo Riccardi, Abdul Mazid, Domenico V Delfino Toxins (Basel). 2019 Aug 29;11(9):503. doi: 10.3390/toxins11090503.
Cladosporium species are endophytic fungi that grow on organic matter and are considered food contaminants. The anti-microbial and anti-tumor naphthoquinones fusarubin (FUS) and anhydrofusarubin (AFU) were isolated using column chromatography from a Cladosporium species residing inside Rauwolfia leaves. The impact of FUS and AFU on cell growth was assessed in acute myeloid leukemia (OCI-AML3) and other hematologic tumor cell lines (HL-60, U937, and Jurkat). Treatment with FUS or AFU reduced the number of OCI-AML3 cells as evaluated by a hemocytometer. Flow cytometry analyses showed that this effect was accompanied by diverse impairments in cell cycle progression. Specifically, FUS (20 or 10 μg/mL significantly decreased the percentage of cells in S phase and increased the percentage of cells in G2/M phase, whereas AFU increased the percentage of cells in G0/G1 phase (50 and 25 μg/mL) and decreased the percentage of cells in S (50 μg/mL) and G2/M (50 and 25 μg/mL) phases. Both substances significantly increased apoptosis at higher concentrations. The effects of FUS were more potent than those of AFU, with FUS up-regulating p21 expression in a p53-dependent manner, as detected by Western blot analyses, likely the consequence of decreased ERK phosphorylation and increased p38 expression (both of which increase p21 stability). FUS also decreased Akt phosphorylation and resulted in increased Fas ligand production and caspase-8/3-dependent apoptosis. These results suggest that FUS and AFU inhibit proliferation and increase apoptosis in cell lines derived from hematological cancers.
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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
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
