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Deoxylapachol (Deoxylapaquinone)

Cat No.:V52184 Purity: ≥98%
Deoxylapachol is the main cytotoxic component of the New Zealand brown alga Landsburgia quercifolia.
Deoxylapachol (Deoxylapaquinone)
Deoxylapachol (Deoxylapaquinone) Chemical Structure CAS No.: 3568-90-9
Product category: Fungal
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
Deoxylapachol is the main cytotoxic component of the New Zealand brown alga Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer effect.
Deoxylapachol is a naturally occurring prenylated 1,4-naphthoquinone that is the primary cytotoxic compound found in the New Zealand brown alga Landsburgia quercifolia and is also isolated from the leaves of Catalpa ovata. It has potent antifungal and anticancer properties. The compound acts as an antifungal agent by inducing cell wall stress in fungi. Deoxylapachol has the molecular formula C15H14O2 and a molecular weight of 226.28.
Biological Activity I Assay Protocols (From Reference)
Targets
Deoxylapachol targets fungal cell walls, inducing cell wall stress in key wood-decay fungi including brown rot and white rot species. The compound is a 1,4-naphthoquinone that exhibits antifungal activity by disrupting fungal cell wall integrity. It also has anticancer properties, making it a promising candidate for antifungal and anticancer treatments. The compound's mechanism of action involves the induction of cell wall stress, leading to fungal cell death.
ln Vitro
Deoxylapachol has an IC50 of 0.6 microgm/ml against P-388 leukemia cells.
In vitro studies demonstrate that deoxylapachol exhibits potent antifungal activity against key wood-decay fungi, including brown rot and white rot species, by inducing cell wall stress. The compound is the primary cytotoxic compound found in the New Zealand brown alga Landsburgia quercifolia. It possesses potent antifungal and anticancer properties. The compound's ability to inhibit fungal growth makes it a promising candidate for antifungal treatments.
ln Vivo
No detailed in vivo activity data has been published for deoxylapachol. The compound has been primarily characterized in vitro as a natural product with antifungal and anticancer properties. Its ability to induce fungal cell wall stress suggests that it could have potential for in vivo applications in treating fungal infections. Further studies would be needed to evaluate its efficacy in animal models of fungal infections or cancer.
Enzyme Assay
The antifungal activity of deoxylapachol can be assessed using standard susceptibility testing methods. In a typical assay, fungal cultures are grown in appropriate media and treated with varying concentrations of deoxylapachol. The minimum inhibitory concentration (MIC) is determined using the broth microdilution method. The compound's ability to induce cell wall stress can be assessed by measuring changes in fungal cell wall integrity using microscopy or biochemical assays.
Cell Assay
The anticancer activity of deoxylapachol can be assessed using cancer cell lines. Cells are seeded in 96-well plates and treated with escalating concentrations of deoxylapachol. Cell viability is measured using MTT or CellTiter-Glo assays. Apoptosis is assessed by annexin V/propidium iodide staining or caspase activation assays. The compound's selectivity for cancer cells over normal cells can be assessed by comparing activity against cancer cell lines and normal cell lines.
Animal Protocol
No detailed in vivo animal model data has been published for deoxylapachol. The compound has been primarily characterized in vitro as a natural product with antifungal and anticancer properties. Future studies may involve the use of mouse models of fungal infections or cancer to assess the in vivo efficacy of deoxylapachol.
ADME/Pharmacokinetics
No detailed pharmacokinetic data has been published for deoxylapachol. The compound has a molecular weight of 226.28 and a molecular formula of C15H14O2. It has a purity of ≥98%. Further studies would be needed to characterize its absorption, distribution, metabolism, and excretion properties, including oral bioavailability, plasma protein binding, clearance, and half-life.
Toxicity/Toxicokinetics
No detailed toxicity data has been published for deoxylapachol. As a naphthoquinone, the compound may have redox-active properties that could contribute to both its antifungal/anticancer activity and its toxicity. Comprehensive toxicology studies would be required to evaluate its safety profile for potential therapeutic development. The compound is intended for research use only.
References

[1]. A cytotoxic and antifungal 1,4-naphthoquinone and related compounds from a New Zealand brown algae, Landsburgia quercifolia. J Nat Prod. Jul-Aug 1991;54(4):978-85.

Additional Infomation
2-Demethylnaphthoquinone is a naphthoquinone, belonging to the paraquinone class of compounds. It is a metabolite of Escherichia coli. Deoxylapalol has been reported to be present in teak, Quercus acutissima, and other organisms with relevant data.
Deoxylapachol (CAS# 3568-90-9) is a naturally occurring prenylated 1,4-naphthoquinone found in the New Zealand brown alga Landsburgia quercifolia and in the leaves of Catalpa ovata. It has potent antifungal activity against wood-decay fungi by inducing cell wall stress, and it also has anticancer properties. The molecular formula is C15H14O2 and molecular weight is 226.28. Deoxylapachol is a research compound for studying antifungal and anticancer mechanisms.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H14O2
Molecular Weight
226.27
Exact Mass
226.099
CAS #
3568-90-9
PubChem CID
97448
Appearance
White to yellow solid powder
Density
1.1±0.1 g/cm3
Boiling Point
359.2±42.0 °C at 760 mmHg
Flash Point
134.8±24.9 °C
Vapour Pressure
0.0±0.8 mmHg at 25°C
Index of Refraction
1.571
LogP
4.24
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
2
Heavy Atom Count
17
Complexity
397
Defined Atom Stereocenter Count
0
InChi Key
OSDFYZPKJKRCRR-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H14O2/c1-10(2)7-8-11-9-14(16)12-5-3-4-6-13(12)15(11)17/h3-7,9H,8H2,1-2H3
Chemical Name
2-(3-methylbut-2-enyl)naphthalene-1,4-dione
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

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 (441.95 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 2.5 mg/mL (11.05 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
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.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.4195 mL 22.0975 mL 44.1950 mL
5 mM 0.8839 mL 4.4195 mL 8.8390 mL
10 mM 0.4419 mL 2.2097 mL 4.4195 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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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

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.
             (2) Be sure to add the solvent(s) in order.

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