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Usnic acid

Alias: NSC-8517; 125-46-2; Usno; 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-; usnic-acid; L-Usnic acid; NSC 8517; NSC5890; NSC 8517; Usnic acid
Cat No.:V27885 Purity: ≥98%
Usnic acid is a lichen secondary metabolite (SM, chemical compound) with a unique dibenzofuran skeleton.
Usnic acid
Usnic acid Chemical Structure CAS No.: 125-46-2
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
50mg
100mg
250mg
Other Sizes

Other Forms of Usnic acid:

  • (+)-Usniacin
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Usnic acid is a lichen secondary metabolite (SM, chemical compound) with a unique dibenzofuran skeleton. Usnic acid has excellent anticancer and antibacterial properties. Usnic acid significantly inhibits RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1.
Biological Activity I Assay Protocols (From Reference)
Targets
Natural product; secondary metabolite
ln Vitro
Osteoclasts are the only cells that can resorb bone and they are produced from monocytes/macrophages in the presence of M-CSF and RANKL and are activated in vivo by an immune response. Usnic acid is a secondary metabolite of lichen and has a unique dibenzofuran skeleton. It has been used for years in cosmetics, fragrances, and traditional medicines. It has a wide range of bioactivities, including anti-inflammatory, anti-bacterial, anti-cancer, anti-viral, and so on. However, the anti-osteoclastogenic activity of usnic acid has not been reported yet. In this study, we investigated whether usnic acid could affect RANKL-mediated osteoclastogenesis. Usnic acid significantly inhibited RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1, a master regulator of osteoclastogenesis [1].
ln Vivo
Effects of Usnic Acid on Serum Biochemical Marker in LPS-Induced Mice [1]
After 8 days of the first usnic acid injection, the concentrations of TRAP-5b, bone resorption marker, were measured from serum by ELISA. The level of serum TRAP-5b in the LPS group was about two times higher than that in the control group, but the level of serum TRAP-5b in the LPS + usnic acid group was about 30% lower than that of the LPS group.
Usnic Acid Inhibited Bone Loss in LPS-Induced Mice [1]
The anti-resorptive activity of usnic acid was evaluated with the LPS-induced mouse bone erosion model. Femora were collected from mice and analyzed by a micro-computed tomography (μCT) system. μCT displayed that bone mass of trabecular bone in the femur metaphyseal region was decreased by LPS treatment, whereas the treatment of usnic acid significantly prevented LPS-mediated trabecular bone loss (Figure 6A). The LPS-mediated changes in bone mineral density (BMD), bone volume/total volume (BV/TV), bone surface/total volume (BS/TV), and trabecular separation (Tb.Sp) were significantly prevented by usnic acid.
Usnic acid prevented lipopolysaccharides (LPS)-induced bone erosion in mice. Taken together, our results suggest that usnic acid might be a potential candidate for the treatment of osteoporosis [1].
Enzyme Assay
Measurements of Serum TRAP by Enzyme-Linked Immunosorbent Assay (ELISA) [1]
Blood was collected from the retro-orbital plexus and centrifuged at 18,000 g for 5 min with LPS treated osteoporosis model mice. Serum was separated and stored at −20 °C. The serum TRAP-5b levels were measured using a Tartrate resistant acid phosphatase 5b ELISA kit. Analyses were performed according to protocols provided by the manufacturers.
Cell Assay
Cell Viability Assay The effect of Usnic acid on the viability of BMMs was determined using Cell Counting Kit-8 (CCK-8) method. Briefly, BMCs were seeded in a 96-well plate at a density of 1 × 104 cells/well and cultured with indicated concentration of Usnic acid (0, 0.3, 1, and 3 µM) for 3 days. Cell viability was evaluated using a CCK-8 kit according to the manufacturer’s protocol.
Bone Pit Formation Assay Bone pit formation assay was performed as described previously. BMMs were differentiated on an Osteo Assay Plate (24 well plate) at a density of 3 × 105 cells/well and stimulated with 10 ng/mL RANKL and 30 ng/mL M-CSF in the presence of Usnic acid (0, 1, and 3 µM). After 4 days, the cells were removed with 5% sodium hypochlorite for 5 min, then the resorption area was observed under a light microscope (magnification, ×50), and after that, measured by ImageJ software.
Animal Protocol
Lipopolysaccharides (LPS)-Induced Bone Erosion All procedures involving mice were conducted in strict accordance with SCNU IACUC guidelines for the care and use of laboratory animals (Permit No: SCNU IACUC-2016-08). LPS-induced bone erosion was performed as described previously [28]. Five-week-old male ICR mice were divided into 3 groups of 6 mice. One day before injection of LPS (Sigma-Aldrich, St. Louis, MO, USA) and subsequently on every day for up to 8 days till the end of the experimental period, intraperitoneal injections of usnic acid (1 μg/g of body weight) or 10% Kolliphor ER in PBS (control) were administered. LPS (5 μg/μL in 0.1% BSA PBS) was injected intraperitoneally on days 1 and 4. All mice were sacrificed by cervical dislocation, and their femora were scanned with High-resolution micro-CT (SKYSCAN 1272; Bruker, Billerica, MA, USA) and imaged by DataViewer (SKYSCAN). The bone mineral density (BMD), bone volume/total volume (BV/TV), bone surface/total volume (BS/TV), and trabecular separation (Tb.Sp) were measured to assess the trabecular bone microstructure of the femur using the CTAn software provided with the SKYSCAN analysis tool.
Toxicity/Toxicokinetics
Adverse Effects
Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
mouse LD50 subcutaneous 75 mg/kg CRC Handbook of Antibiotic Compounds, Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980, 9(89), 1982
mouse LD50 intravenous 25 mg/kg Antibiotics., 1(611), 1967
rabbit LD oral >500 mg/kg Arzneimittel-Forschung. Drug Research., 5(510), 1955 [PMID:13276269]
Antidote and Emergency Treatment
/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
Non-Human Toxicity Values
LD50 Dog iv 40 mg/kg PMID:12453567

LD50 Rabbit iv 30 mg/kg PMID:12453567

LD50 Rat iv 30 mg/kg PMID:12453567

LD50 Rabbit oral 500 mg/kg
Non-Human Toxicity Values
LD50 Dog iv 40 mg/kg
LD50 Rabbit iv 30 mg/kg
LD50 Rat iv 30 mg/kg
LD50 Rabbit oral 500 mg/kg
For more Non-Human Toxicity Values (Complete) data for USNIC ACID (6 total), please visit the HSDB record page.
References

[1]. Effect of Usnic Acid on Osteoclastogenic Activity. J Clin Med. 2018 Oct 12;7(10). pii: E345.

Additional Infomation
7-Hydroxy-(S)-usnate is a member of benzofurans.
Usnic acid has been reported in Dimelaena oreina, Flavoparmelia haysomii, and other organisms with data available.
See also: (-)-Usnic Acid (annotation moved to).
Mechanism of Action
The physiological effects of usnic acid /was investigated/ in two cultured species of the lichen alga Trebouxia. Exposing Trebouxia to the sodium salt of usnic acid resulted in the inhibition of growth and photosynthesis, an incr in membrane permeability and immobilization of zoospore. /Usnic acid, sodium salt/
The mechanism of action expressed by usnic acid remains speculative. (+)-Usnic acid has been shown to be an uncoupler of oxidative phosphorylation in mouse-liver mitochondria at levels of 1 uM.
The accumulation of usnic acid can be stimulated by the inhibition of photosynthesis, suggesting a possible role of glucose in regulating enzymes of phenol synthesis.
Experiments show that usnic acid is an allelopathic agent, inhibiting moss spore germination and that its effectiveness is pH dependent.
In vitro, usnic acid has a slight inhibitory action against leukotriene biosynthesis in bovine polymorphonuclear leukocytes by a specific enzyme interaction rather than acting as an antioxidant against the peroxidation process, or as a scavenger, or even as a source of free radicals.
Osteoclasts are the only cells that can resorb bone and they are produced from monocytes/macrophages in the presence of M-CSF and RANKL and are activated in vivo by an immune response. Usnic acid is a secondary metabolite of lichen and has a unique dibenzofuran skeleton. It has been used for years in cosmetics, fragrances, and traditional medicines. It has a wide range of bioactivities, including anti-inflammatory, anti-bacterial, anti-cancer, anti-viral, and so on. However, the anti-osteoclastogenic activity of usnic acid has not been reported yet. In this study, we investigated whether usnic acid could affect RANKL-mediated osteoclastogenesis. Usnic acid significantly inhibited RANKL-mediated osteoclast formation and function by reducing the transcriptional and translational expression of NFATc1, a master regulator of osteoclastogenesis. In addition, it prevented lipopolysaccharides (LPS)-induced bone erosion in mice. Taken together, our results suggest that usnic acid might be a potential candidate for the treatment of osteoporosis.[1]
Therapeutic Uses
Recent studies in which the anti-inflammatory activity of (+)-usnic acid was compared to that of ibuprofen using the rat paw edema assay (acute effects) and the cotton pellet assay (chronic effects) showed (+)-usnic acid to be significantly effective in both assays at an oral dose of 100 mg/kg adn comparable to ibuprofen at the same dose. PMID:12453567
/EXPL THER: / Commercially obtained (+)-usnic acid was shown to inhibit cytopathic effects of Herpes simplex type 1 and polio type 1 viruses when administered on filter paper discs which were placed on virus-infected African green monkey kidney (BS-C-1) cells. PMID:12453567
/EXPL THER:/ Oral administration of usnic acid at 30 and 100 mg/kg resulted in significant analgesic effects as determined by the acetic acid-induced writhing- and tail pressure tests. Usnic acid administered orally at doses of 100 and 300 mg/kg exhibited significant antipyretic activity as evaluated through lipopolysaccharide-induced hyperthermia. PMID:12453567
/Usnic acid/ inhibits the growth of multi-resistant strains of Staphylococcus aureus, enterococci and mycobacteria. PMID:12061397
Usnic acid had anti-osteoclastogenesis activity by inhibiting the expression of NFATc1 via down-regulating RANKL-mediated ERK activation and it could significantly prevent LPS-induced bone loss in vivo. Therefore, usnic acid might be used as a new structural scaffold for the treatment of bone diseases, such as osteoporosis.[1]
Therapeutic Uses
Recent studies in which the anti-inflammatory activity of (+)-usnic acid was compared to that of ibuprofen using the rat paw edema assay (acute effects) and the cotton pellet assay (chronic effects) showed (+)-usnic acid to be significantly effective in both assays at an oral dose of 100 mg/kg adn comparable to ibuprofen at the same dose.
/EXPL THER: / Commercially obtained (+)-usnic acid was shown to inhibit cytopathic effects of Herpes simplex type 1 and polio type 1 viruses when administered on filter paper discs which were placed on virus-infected African green monkey kidney (BS-C-1) cells.
/EXPL THER:/ Oral administration of usnic acid at 30 and 100 mg/kg resulted in significant analgesic effects as determined by the acetic acid-induced writhing- and tail pressure tests. Usnic acid administered orally at doses of 100 and 300 mg/kg exhibited significant antipyretic activity as evaluated through lipopolysaccharide-induced hyperthermia.
/Usnic acid/ inhibits the growth of multi-resistant strains of Staphylococcus aureus, enterococci and mycobacteria.
For more Therapeutic Uses (Complete) data for USNIC ACID (8 total), please visit the HSDB record page.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H16O7
Molecular Weight
344.31
Exact Mass
344.089
Elemental Analysis
C, 62.79; H, 4.68; O, 32.53
CAS #
125-46-2
Related CAS #
(+)-Usnic acid;7562-61-0
PubChem CID
5646
Appearance
White to yellow solid powder
Melting Point
204 °C
LogP
1.4
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
7
Rotatable Bond Count
2
Heavy Atom Count
25
Complexity
708
Defined Atom Stereocenter Count
0
SMILES
O=C(C1(C)C(OC2=C(C(C)=O)C(O)=C(C)C(O)=C12)=C3)C(C(C)=O)C3=O
InChi Key
CUCUKLJLRRAKFN-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3
Chemical Name
2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
Synonyms
NSC-8517; 125-46-2; Usno; 1,3(2H,9bH)-Dibenzofurandione, 2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-; usnic-acid; L-Usnic acid; NSC 8517; NSC5890; NSC 8517; Usnic acid
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 : ~3.33 mg/mL (~9.67 mM)
Solubility (In Vivo)
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

Injection Formulations
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO 400 μLPEG300 50 μL Tween 80 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).
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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO 900 μL (20% SBE-β-CD in saline)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL Saline)


Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.9044 mL 14.5218 mL 29.0436 mL
5 mM 0.5809 mL 2.9044 mL 5.8087 mL
10 mM 0.2904 mL 1.4522 mL 2.9044 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)
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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.
             (2) Be sure to add the solvent(s) in order.

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