| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Source | Plant — Rubiaceae Rubia tinctorum L. |
| Molecular weight | |
| Molecular formula | C25H26O13 |
| SMILES | |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Ruberythric acid is a natural product found in madder (Rubia tinctorum). Acid treatment hydrolyzes it into pentose-containing sugar residues and alizarin. It blocks stimulus-induced phosphorylation of IKK, IκBα, and p65 within the NF-κB pathway, preserves tight junction integrity, curbs stimulus-induced MLCK activation and lowers myosin light chain phosphorylation, limits cytoskeletal-contraction-related tight junction disruption, eases stimulus-induced increases in intestinal permeability, and prevents stimulus-induced redistribution of tight junction proteins. Dissolved in alkali, it forms red salts and can serve as a dye, and it is applied to inflammatory bowel disease research[1][2][3]. It has the molecular formula C25H26O13 and a molecular weight of 534.47 g/mol.
Physical & Chemical Properties
| CAS Number | 152-84-1 |
|---|---|
| Molecular Formula | C25H26O13 |
| Molecular Weight | 534.47 g/mol |
| Structure Classification | Saccharides Polysaccharides |
| SMILES | O=C1C2=C(O)C(O[C@@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO[C@H]4[C@@H]([C@H]([C@@H](CO4)O)O)O)=CC=C2C(C5=CC=CC=C51)=O |
| Target | IKK, MLCK, Claudin-2 |
| Signaling Pathway | NF-κB; Cytoskeleton |
| Initial Source | Plant — Rubiaceae Rubia tinctorum 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.
[2]. Jones E T. 275. Natural glycosides. Part V. Ruberythric acid. J. Chem. Soc., 1933, 136: 1167‑1169.
[3]. Wouters J, et al. A Comparative Investigation of Hydrolysis Methods to Analyze Natural Organic Dyes by HPLC‑PDA NINE METHODS, TWELVE BIOLOGICAL SOURCES, TEN DYE CLASSES, DYED YARNS, PIGMENTS AND PAINTS. Studies in Conservation, 2011, 56(3): 231‑249.
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
Ruberythric acid (RBA) (12.5-50 μM; 24 h) shows no cytotoxicity toward Caco-2 cells[1]. Ruberythric acid (12.5-50 μM; pretreated for 1 h, then 48 h of STI exposure) significantly alleviates the STI-induced decrease in transepithelial electrical resistance (TEER) and rise in FITC-dextran permeability across Caco-2 cell monolayers[1]. In Caco-2 cells, Ruberythric acid (25-50 μM; 1 h pretreatment before STI exposure) blocks STI-induced redistribution of the tight junction proteins ZO-1 and claudin-2 and keeps them at their normal membrane localization[1]. In Caco-2 cells, Ruberythric acid (50 μM; 1 h pretreatment before 0.75 h and 1 h of STI exposure) suppresses STI-induced MLCK activation and MLC phosphorylation[1]. Amygdalinase can hydrolyze Ruberythric acid, which contains a pentose residue, consistent with classifying it as a pentose-β-glucoside of the primveroside or vicianoside type[2]. Ruberythric acid is recoverable efficiently from madder pigment samples by combining 4-hour hydrofluoric acid hydrolysis, oxalic acid hydrolysis, plus conventional hydrochloric acid hydrolysis; from madder-dyed silk and wool textile samples, it can be recovered with high efficiency by combining oxalic acid hydrolysis with conventional hydrochloric acid hydrolysis[3]. In Caco-2 cells, Ruberythric acid (50 μM; 1 h pretreatment before 1 h of STI exposure) suppresses STI-induced phosphorylation of IKKα/β, IκBα and p65 in the NF-κB pathway[1].
Cell Viability Assay[1]
| Cell Line | human colorectal adenocarcinoma Caco-2 cells |
|---|---|
| Concentration | 12.5, 25, 50 μM |
| Incubation Time | 24 h |
| Result | Showed no cytotoxic effects on Caco-2 cells at all tested concentrations, with cell viability remaining comparable to the untreated control group. |
Immunofluorescence[1]
| Cell Line | differentiated human colorectal adenocarcinoma Caco-2 cells |
|---|---|
| Concentration | 25, 50 μM |
| Incubation Time | 1 h pretreatment prior to STI exposure |
| Result | Confirmed inhibition of STI-induced redistribution of ZO-1 (restaining at cell junctions) and claudin-2 (reducing its membrane localization to control-like levels). |
Western Blot Analysis[1]
| Cell Line | differentiated human colorectal adenocarcinoma Caco-2 cells |
|---|---|
| Concentration | 50 μM |
| Incubation Time | 1 h pretreatment prior to STI exposure |
| Result | Inhibited STI-induced delocalization of ZO-1 and claudin-2 from the cell membrane to the cytosol at 1 h post-stimulation. |
Western Blot Analysis[1]
| Cell Line | differentiated human colorectal adenocarcinoma Caco-2 cells |
|---|---|
| Concentration | 50 μM |
| Incubation Time | 1 h pretreatment prior to 1 h STI exposure |
| Result | Significantly inhibited STI-induced phosphorylation of IKKα/β, IκBα, and p65 in the NF-κB pathway at 1 h post-stimulation. |
Western Blot Analysis[1]
| Cell Line | differentiated human colorectal adenocarcinoma Caco-2 cells |
|---|---|
| Concentration | 50 μM |
| Incubation Time | 1 h pretreatment prior to 0.75 h and 1 h STI exposure |
| Result | Significantly alleviated STI-induced activation of MLCK at 0.75 h post-stimulation. Significantly alleviated STI-induced phosphorylation of MLC at 1 h post-stimulation. |
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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