| Field | Specification |
|---|---|
| CAS no. | |
| Applications | |
| Source | Plant — Arecaceae Phoenix dactylifera L. |
| Molecular weight | |
| Molecular formula | C13H14O6 |
| Activity | |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Dihydrocitrinone is a polyketide secondary metabolite and the major urinary metabolite of citrinin, isolable from Aspergillus strains derived from the rhizosphere soil of date palms. It exerts toxic effects on its own in renal cell cultures and zebrafish embryo models, enhances the toxicity of Ochratoxin A through additive or synergistic action, and raises miR-731 levels in zebrafish embryos when combined with Ochratoxin A[1][2]. It has the molecular formula C13H14O6 and a molecular weight of 266.25 g/mol.
Physical & Chemical Properties
| CAS Number | 65718-85-6 |
|---|---|
| Molecular Formula | C13H14O6 |
| Molecular Weight | 266.25 g/mol |
| SMILES | OC1=C2C(=C(C)C(O)=C1C(O)=O)[C@H](C)[C@@H](C)OC2=O |
| Signaling Pathway | Metabolic Enzyme/Protease |
| Bioactivity Class | Fungal Metabolite |
| Initial Source | Plant — Arecaceae Phoenix dactylifera L. |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with your institution's chemical hygiene plan.
In Vitro
In 2D MDBK cells, Dihydrocitrinone (2.5-50 μM; 24 h) significantly enhances the ochratoxin A-induced reduction in cell viability[2]. At 50 μM for 24 h, Dihydrocitrinone significantly enhances ochratoxin A-induced loss of cell viability in 2D MDCK cells[2]. In 3D MDCK spheroid cells, 24 h treatment with Dihydrocitrinone (2.5-50 μM) significantly amplifies the ochratoxin A-induced reduction in cell viability[2].
Cell Viability Assay[2]
| Cell Line | 2D bovine kidney epithelial MDBK cells |
|---|---|
| Concentration | 2.5, 10, 25, 50 μM (co-incubation with 0.5 μM Ochratoxin A) |
| Incubation Time | 24 h |
| Result | Significantly enhanced Ochratoxin A-induced toxicity, causing greater reductions in cellular ATP levels compared to ochratoxin A alone. |
Cell Viability Assay[2]
| Cell Line | 2D canine kidney epithelial MDCK cells |
|---|---|
| Concentration | 50 μM (co-incubation with 1 μM Ochratoxin A) |
| Incubation Time | 24 h |
| Result | Significantly enhanced Ochratoxin A-induced toxicity, causing a greater reduction in cellular ATP levels compared to ochratoxin A alone. |
Cell Viability Assay[2]
| Cell Line | 3D canine kidney epithelial MDCK spheroid cells |
|---|---|
| Concentration | 2.5, 10, 25, 50 μM (co-incubation with 1.5 μM Ochratoxin A) |
| Incubation Time | 24 h |
| Result | Significantly enhanced Ochratoxin A-induced toxicity, causing major reductions in cellular ATP levels compared to ochratoxin A alone. |
In Vivo
In zebrafish embryos exposed by static immersion, continuously from the pre-eight-cell stage to 48 hpf or 120 hpf, Dihydrocitrinone (0.78-50 μM) alone causes no acute lethal or nephrotoxic effects at concentrations up to 50 μM; however, co-administration with Ochratoxin A significantly increases the mortality and nephrotoxicity that Ochratoxin A induces (characterized by upregulated miR-731 expression and pronephric duct malformations)[2].
| Animal Model | AB strain; Tg(wt1b:GFP) transgenic strain (newly fertilized embryos)[2] |
|---|---|
| Dosage | 0.78 μM, 1.56 μM, 3.125 μM, 6.25 μM, 12.5 μM, 25 μM, 50 μM (individual exposure); 3.125 μM, 12.5 μM, 25 μM (combined with 0.23 μM Ochratoxin A) |
| Administration | static immersion; continuous exposure; pre-eight-cell stage to 120 hpf or 48 hpf |
| Result | Did not cause mortality in zebrafish embryos at 120 hpf at concentrations up to 50 μM. Did not significantly alter miR-731 expression or pronephros morphology in 48 hpf transgenic embryos at 3.125 μM. Significantly increased embryo mortality at 120 hpf when combined with 0.23 μM Ochratoxin A at 12.5 μM and 25 μM. Significantly increased miR-731 expression (relative expression ~25-fold compared to control) and caused visible malformations to the pronephric duct section of the pronephros in 48 hpf transgenic embryos when combined with 0.23 μM Ochratoxin A at 3.125 μM. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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