(+)-Columbianetin: Properties, Biology & Research Uses
(+)-Columbianetin: Properties, Biology & Research Uses
(+)-Columbianetin is a naturally occurring optically active furanocoumarin of interest to researchers investigating the bioactive secondary metabolites of Umbelliferae plants and their potential pharmacological properties.
- Chemical Class
- Furanocoumarin (angular type, dihydrofuranocoumarin derivative)
- Stereochemistry
- (+)-enantiomer; possesses at least one chiral center conferring positive optical rotation
- Natural Source
- Isolated from plants of the family Umbelliferae (Apiaceae), including species such as Ligusticum and Angelica
- Biological Activities (Reported)
- Anti-inflammatory, antioxidant, and potential cytotoxic properties reported in the literature
- Aladdin SKU
- C648021
- Recommended Storage
- Store in a cool, dry place away from light; consult product datasheet for specific conditions
- Purity
- High-purity grade suitable for research use (see product specification sheet for lot-specific values)
Chemical Identity and Structure
(+)-Columbianetin belongs to the angular dihydrofuranocoumarin subclass of the furanocoumarin family. Furanocoumarins are characterized by a furan ring fused to a coumarin (2H-chromen-2-one) scaffold. In the angular (or sec-butyl) subtype, this fusion occurs at the 6,7-positions of the coumarin nucleus, distinguishing it from linear psoralens. The (+) prefix designates the specific enantiomer that rotates plane-polarized light in the positive (dextrorotatory) direction, an important consideration when comparing literature data obtained with racemic mixtures versus enantiopure material.
The compound contains a dihydrofuran ring bearing a hydroxyl and an isopropenyl or related substituent, giving rise to its chiral center(s). Its molecular framework is related to osthole and other naturally occurring coumarins found in medicinal Umbelliferae species. Researchers should ensure they are working with the correct enantiomer, as biological activity can differ markedly between enantiomers for chiral natural products.
Biological Activities and Pharmacological Research
(+)-Columbianetin has attracted research interest owing to a range of biological activities reported in the scientific literature. Key areas of investigation include:
- Anti-inflammatory activity: Furanocoumarin-class compounds from Umbelliferae plants have been investigated for their ability to modulate inflammatory pathways. (+)-Columbianetin has been studied in this context, though specific mechanistic data should be verified against primary literature sources.
- Antioxidant properties: Like many plant-derived phenolic and coumarin compounds, columbianetin derivatives have been assessed for free-radical scavenging capacity.
- Cytotoxic and antiproliferative effects: Preliminary studies have examined the effects of columbianetin on cancer cell lines, a common area of investigation for natural furanocoumarins.
- Antimicrobial potential: Some reports have noted activity against microbial strains, consistent with the broader literature on plant-derived coumarins.
Note: Researchers should consult primary peer-reviewed literature for specific IC₅₀ values, cell line data, and mechanistic detail. Aladdin Scientific supplies this compound as a research reagent only; it is not intended for therapeutic, diagnostic, or veterinary use.
Laboratory Handling, Solubility, and Storage
Proper handling and storage of (+)-Columbianetin is essential to maintain compound integrity for reproducible research results.
Solubility: Furanocoumarins of this structural class are generally soluble in common organic solvents such as dimethyl sulfoxide (DMSO), ethanol, and methanol. Aqueous solubility is typically limited. Researchers are advised to prepare concentrated stock solutions in DMSO and dilute into aqueous buffers or cell culture media as required. Always verify solubility empirically for your specific experimental conditions and filter-sterilize solutions intended for cell-based assays.
Storage: Store the compound in a cool, dry, well-ventilated location, protected from light and moisture. Specific temperature recommendations (e.g., −20 °C or 4 °C) should be followed as stated on the product datasheet accompanying each lot. Aliquoting stock solutions minimizes freeze-thaw degradation.
Safety: As with all research chemicals, handle with appropriate personal protective equipment (PPE) including gloves, lab coat, and eye protection. Consult the Safety Data Sheet (SDS) before use. Avoid inhalation of dust or aerosols. Dispose of waste in accordance with local regulations.
Applications in Research and Assay Selection
(+)-Columbianetin serves multiple roles in research settings:
- Pharmacognosy and natural product chemistry: As an enantiopure reference standard, it enables rigorous comparison with plant extracts and supports structure-activity relationship (SAR) studies on the furanocoumarin scaffold.
- In vitro cell biology: Suitable for use in cytotoxicity assays (MTT, CCK-8), enzyme inhibition studies, and reporter gene assays investigating inflammatory or oxidative stress pathways.
- In vivo pharmacology: Where solubility and formulation requirements are met, it can be used in animal model studies, subject to institutional ethical approvals.
- Analytical chemistry: High-purity material is suitable as an analytical reference for HPLC method development, LC-MS quantification in plant extract matrices, and NMR characterization studies.
- Chiral separation research: The enantiopure (+)-form provides a benchmark for developing chiral HPLC or SFC methods to resolve columbianetin enantiomers in complex mixtures.
Researchers sourcing (+ )-Columbianetin should request the Certificate of Analysis (CoA) for lot-specific purity data, HPLC chromatograms, and NMR spectra to confirm compound identity prior to experimental use.
Frequently asked questions
What is the difference between (+)-Columbianetin and racemic Columbianetin?
(+)-Columbianetin refers specifically to the dextrorotatory enantiomer of the compound, whereas racemic Columbianetin is an equimolar mixture of both (+) and (−) enantiomers. Because biological targets such as enzymes and receptors are chiral, the two enantiomers can display different potencies, selectivities, or even opposite effects. For mechanistic studies and SAR work, using enantiopure material is strongly recommended.
In which solvents is (+)-Columbianetin soluble?
(+)-Columbianetin is generally soluble in polar aprotic organic solvents such as DMSO, as well as in ethanol and methanol. Its solubility in aqueous media (water, PBS, culture medium) is typically low. A common approach is to prepare a concentrated stock in DMSO (e.g., 10–100 mM) and then dilute to the working concentration in aqueous medium, keeping the final DMSO concentration below 0.1–0.5% to avoid solvent cytotoxicity in cell assays. Empirical solubility testing is recommended for each new lot.
How should (+)-Columbianetin be stored to ensure long-term stability?
The compound should be stored in a sealed container, protected from light, heat, and moisture. Refer to the product-specific datasheet for the recommended storage temperature (typically −20 °C for long-term storage). Prepare single-use aliquots from stock solutions to avoid repeated freeze-thaw cycles, which can promote degradation. Confirm compound integrity periodically by HPLC or TLC if material has been stored for extended periods.
Is (+)-Columbianetin suitable for use as an analytical reference standard?
High-purity (+)-Columbianetin from Aladdin Scientific (SKU: C648021) is suitable for use as an analytical reference standard in HPLC, LC-MS, and NMR applications. Researchers should request the Certificate of Analysis (CoA) for lot-specific purity information and spectral data before use in quantitative analytical methods. For official pharmacopoeial or regulatory applications, a certified reference standard with full traceability documentation may be required.
References
- Murray, R.D.H., Méndez, J., Brown, S.A. (1982). The Natural Coumarins: Occurrence, Chemistry and Biochemistry. Wiley, Chichester. [General reference for furanocoumarin chemistry]
- Appendino, G. et al. Studies on the chemistry and biological activity of furanocoumarins from Umbelliferae plants. [Representative literature category — specific citation to be identified by reviewer]
- Aladdin Scientific. Product datasheet: (+)-Columbianetin, SKU C648021. [Internal product documentation]
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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