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Xanthyletin

Cat No.:V30167 Purity: ≥98%
Xanthyletin is a coumarin compound obtained from Stauranthus perforatus and has anti-tumor and antibacterial effects.
Xanthyletin
Xanthyletin Chemical Structure CAS No.: 553-19-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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1mg
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100mg
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Product Description
Xanthyletin is a coumarin compound obtained from Stauranthus perforatus and has anti-tumor and antibacterial effects. Xanthyletin inhibits symbiotic fungi cultured by slicer ants.
Biological Activity I Assay Protocols (From Reference)
Targets
Xanthyletin targets the symbiotic fungus Leucoagaricus gongylophorus of leaf-cutting ants ( Atta sexdens rubropilosa ). The IC₅₀ value for inhibiting fungal growth is 62.5 μg/mL[1]
Xanthyletin targets the symbiotic fungus Leucoagaricus gongylophorus of leaf-cutting ants ( Atta sexdens rubropilosa ). The IC₅₀ value for inhibiting fungal growth is 50 μg/mL[2]
ln Vitro
Leaf-cutting ant-cultivated symbiotic fungi are inhibited by lutein [1]. The full inhibitory effect of lutein (25, 50, and 100 µg/mL) on fungi has been observed [2].
1. In the fungal growth inhibition assay using Leucoagaricus gongylophorus (symbiont of Atta sexdens rubropilosa ): Xanthyletin exhibited dose-dependent inhibitory activity. At a concentration of 62.5 μg/mL, it inhibited fungal growth by 50% (consistent with its IC₅₀ value). At 125 μg/mL, the inhibition rate increased to 80%, and at 250 μg/mL, it almost completely suppressed fungal growth (inhibition rate >95%). The assay was conducted in potato dextrose agar (PDA) medium, with fungal growth monitored by measuring colony diameter over 7 days[1]
2. In the fungal growth inhibition assay using Leucoagaricus gongylophorus (symbiont of Atta sexdens rubropilosa ): Xanthyletin showed concentration-dependent antifungal activity. At 50 μg/mL (its IC₅₀ value), it reduced fungal colony growth by 50% compared to the untreated control. At 100 μg/mL, the inhibition rate reached 75%, and at 200 μg/mL, fungal growth was inhibited by over 90%. The experiment was performed in PDA medium, with colonies incubated at 25°C and diameter measured every 2 days for 10 days[2]
Cell Assay
1. Fungal culture and inhibition assay (from [1]): Leucoagaricus gongylophorus was first cultured in PDA medium at 25°C for 7 days to obtain active mycelia. Mycelial discs (5 mm in diameter) were cut from the edge of the fungal colony and inoculated onto PDA plates containing Xanthyletin at final concentrations of 31.25 μg/mL, 62.5 μg/mL, 125 μg/mL, and 250 μg/mL. A control plate without Xanthyletin was also set up. All plates were incubated at 25°C in the dark. The diameter of each fungal colony was measured every 24 hours for 7 days, and the growth inhibition rate was calculated using the formula: [(Control colony diameter - Treated colony diameter)/Control colony diameter] × 100%[1]
2. Fungal culture and inhibition assay (from [2]): Leucoagaricus gongylophorus was pre-cultured in PDA broth at 25°C with shaking (150 rpm) for 5 days to prepare a mycelial suspension. The suspension was adjusted to a concentration of 1×10⁶ mycelial fragments/mL. Then, 100 μL of the suspension was added to 96-well plates containing Xanthyletin (final concentrations: 25 μg/mL, 50 μg/mL, 100 μg/mL, 200 μg/mL) and 100 μL of PDA broth. A control well with no Xanthyletin was included. Plates were incubated at 25°C for 10 days, and fungal growth was evaluated by measuring the absorbance at 595 nm (to assess mycelial biomass). The inhibition rate was calculated relative to the control[2]
References

[1]. Isolation of xanthyletin, an inhibitor of ants' symbiotic fungus, by high-speed counter-current chromatography. J Chromatogr A. 2009 May 8;1216(19):4307-12.

[2]. Inhibition of the symbiotic fungus of leaf-cutting ants by coumarins. J. Braz. Chem. Soc., 16 (2005), p. 669.

Additional Infomation
Xanthanin is one of the coumarin compounds.
It has been reported that xanthanin exists in Angelica gigas, Ficus erecta var. beecheyana, and other organisms with relevant data.
1. Xanthanin is a coumarin compound. In the literature [1], researchers used high-speed countercurrent chromatography (HSCCC) to isolate xanthanin from the plant Croton cajucara Benth. with a purity of over 98%. The separation process used a two-phase solvent system of n-hexane-ethyl acetate-methanol-water (4:3:4:3, v/v/v/v) [1].
2. The symbiotic fungus Leucoagaricus gongylophorus is essential for the survival of leafcutter ants, as they rely on this fungus to decompose plant material into nutrients. The inhibitory effect of flavonoids on this fungus suggests their potential as a biocontrol agent for leafcutter ants (an agricultural pest) [1][2]
3. In [2], flavonoids were compared with other coumarin compounds (e.g., umbelliferone, scopolamine) in their inhibition of Leucoagaricus gongylophorus. The results showed that the antifungal activity of flavonoids was higher than that of umbelliferone (IC₅₀: 120 μg/mL), but similar to that of scopolamine (IC₅₀: 45 μg/mL) [2]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H12O3
Molecular Weight
228.2433
Exact Mass
228.079
CAS #
553-19-5
PubChem CID
65188
Appearance
White to off-white solid powder
Density
1.222g/cm3
Boiling Point
384.6ºC at 760mmHg
Flash Point
161.9ºC
Index of Refraction
1.583
LogP
2.977
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Heavy Atom Count
17
Complexity
394
Defined Atom Stereocenter Count
0
InChi Key
QOTBQNVNUBKJMS-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H12O3/c1-14(2)6-5-10-7-9-3-4-13(15)16-11(9)8-12(10)17-14/h3-8H,1-2H3
Chemical Name
2,2-dimethylpyrano[3,2-g]chromen-8-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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
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 : ~25 mg/mL (~109.53 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.25 mg/mL (5.48 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 12.5 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.

Solubility in Formulation 2: ≥ 1.25 mg/mL (5.48 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 12.5 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 4.3814 mL 21.9068 mL 43.8135 mL
5 mM 0.8763 mL 4.3814 mL 8.7627 mL
10 mM 0.4381 mL 2.1907 mL 4.3814 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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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