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Columbianetin

Cat No.:V30681 Purity: ≥98%
(+)-Columbianetin is an enantiomer of Columbianetin.
Columbianetin
Columbianetin Chemical Structure CAS No.: 3804-70-4
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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25mg
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Other Forms of Columbianetin:

  • Columbianetin acetate
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
(+)-Columbianetin is an enantiomer of Columbianetin. Columbianetin is a phytoalexin implicated in celery resistance to pathogens during storage. Columbianetin has good antifungal and anti~inflammatory activities.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
- Against celery pathogens (including Botrytis cinerea and Fusarium oxysporum), Columbianetin showed dose-dependent inhibitory activity on mycelial growth and spore germination. At a concentration of 20 μg/mL, it inhibited the mycelial growth of Botrytis cinerea by 68% and the spore germination rate by 72%; at the same concentration, it inhibited the mycelial growth of Fusarium oxysporum by 59% [1]
- In human mast cells (HMC-1 cell line) activated by phorbol 12-myristate 13-acetate (PMA, 10 nM) and calcium ionophore A23187 (1 μM), Columbianetin (1, 10, 30 μM) dose-dependently inhibited the release of pro-inflammatory mediators. At 30 μM, it reduced tumor necrosis factor-α (TNF-α) release by 62%, interleukin-6 (IL-6) release by 58%, and interleukin-8 (IL-8) release by 51% compared with the activated control group. It also inhibited histamine release by 45% at 30 μM [2]
- Columbianetin (10, 30 μM) suppressed the activation of nuclear factor-κB (NF-κB) and mitogen-activated protein kinase (MAPK) pathways in activated HMC-1 cells: it reduced the phosphorylation of IκBα (inhibitor of NF-κB) by 70% at 30 μM, and decreased the phosphorylation levels of extracellular signal-regulated kinase (ERK) and p38 MAPK by 65% and 60%, respectively, at the same concentration [2]
Cell Assay
- For human mast cell (HMC-1) experiment: HMC-1 cells were cultured in RPMI 1640 medium supplemented with 10% fetal bovine serum, 100 U/mL penicillin, and 100 μg/mL streptomycin, maintained at 37°C in a 5% CO₂ incubator. Cells were seeded in 24-well plates at a density of 5×10⁵ cells/well and preincubated with Columbianetin (1, 10, 30 μM) for 1 hour. Then, the cells were stimulated with a combination of PMA (10 nM) and A23187 (1 μM) for 24 hours. After stimulation, the cell supernatant was collected by centrifugation. The levels of TNF-α, IL-6, and IL-8 in the supernatant were detected using enzyme-linked immunosorbent assay (ELISA) kits, and the histamine level was measured by a fluorometric assay. For Western blot analysis, cells were lysed with RIPA buffer containing protease and phosphatase inhibitors, and the lysates were separated by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE), then transferred to polyvinylidene fluoride (PVDF) membranes. The membranes were probed with primary antibodies against phosphorylated IκBα (p-IκBα), phosphorylated ERK (p-ERK), phosphorylated p38 (p-p38), and β-actin (loading control), followed by incubation with secondary antibodies. The bands were visualized using an enhanced chemiluminescence (ECL) detection system [2]
Toxicity/Toxicokinetics
In HMC-1 cell viability assay (MTT assay), high concentrations of 30 μM of columbin did not show significant cytotoxicity after 24 hours of treatment; compared with the untreated control group, cell viability remained above 90% [2].
References

[1]. Columbianetin, a phytoalexin associated with celery resistance to pathogens during storage. 1995. Volume 39, Issue 6, August 1995, Pages 1347-1350.

[2]. Anti-inflammatory effect of Columbianetin on activated human mast cells. Biol Pharm Bull. 2009 Jun;32(6):1027-31.

Additional Infomation
(S)-Columbin is the (S)-(+)-enantiomer of columbin and also the enantiomer of (R)-Columbin.
Columbin has been reported to be present in Zanthoxylum bungeanum, Curvularia pubescens, and other organisms with relevant data.
- Columbin is a phytoalexin that is produced naturally during celery storage. Its accumulation in celery tissues is closely associated with celery’s resistance to postharvest pathogen infections, such as those caused by Botrytis cinerea and Fusarium oxysporum [1].
- Columbin’s anti-inflammatory effect on activated human mast cells is mainly achieved by inhibiting the NF-κB and MAPK signaling pathways, thereby reducing the release of pro-inflammatory cytokines and histamine. This suggests its potential application value in treating inflammatory diseases associated with mast cell activation, such as allergic diseases [2]
-Columbin is a coumarin compound whose molecular structure contains a coumarin core and a hydroxyl group at a specific position, which is considered to be related to its biological activities (antibacterial and anti-inflammatory) [1][2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H14O4
Molecular Weight
246.2586
Exact Mass
246.089
CAS #
3804-70-4
Related CAS #
(+)-Columbianetin acetate;23180-65-6
PubChem CID
92201
Appearance
Off-white to light yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
443.0±45.0 °C at 760 mmHg
Flash Point
171.9±22.2 °C
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.611
LogP
1.69
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
1
Heavy Atom Count
18
Complexity
387
Defined Atom Stereocenter Count
1
SMILES
CC(C)([C@@H]1CC2=C(O1)C=CC3=C2OC(=O)C=C3)O
InChi Key
YRAQEMCYCSSHJG-NSHDSACASA-N
InChi Code
InChI=1S/C14H14O4/c1-14(2,16)11-7-9-10(17-11)5-3-8-4-6-12(15)18-13(8)9/h3-6,11,16H,7H2,1-2H3/t11-/m0/s1
Chemical Name
(8S)-8-(2-hydroxypropan-2-yl)-8,9-dihydrofuro[2,3-h]chromen-2-one
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~406.07 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.15 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.0607 mL 20.3037 mL 40.6075 mL
5 mM 0.8121 mL 4.0607 mL 8.1215 mL
10 mM 0.4061 mL 2.0304 mL 4.0607 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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