Antibiotic lichen acid
2,6-diacetyl-1,2,3,9b-tetrahydro-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3-dione
CAS: 125-46-2;7562-61-0
Molecular Formula: C18H16O7
Antibiotic lichen acid - Names and Identifiers
Antibiotic lichen acid - Physico-chemical Properties
| Molecular Formula | C18H16O7 |
| Molar Mass | 344.32 |
| Density | 1.2869 (rough estimate) |
| Melting Point | 200°C |
| Boling Point | 399.43°C (rough estimate) |
| Specific Rotation(α) | D16 +509.4° (c = 0.697 in chloroform) |
| Flash Point | 223.3°C |
| Solubility | Solubility at 25°C (g/100ml water)<0.01, acetone 0.77, ethyl acetate 0.88, ethanol 0.02, sugar aldehyde 7.32, sugar alcohol 1.21. |
| Vapor Presure | 3E-15mmHg at 25°C |
| Appearance | Yellow oblique prism columnar crystal (acetone) |
| Merck | 9893 |
| pKa | 4.00±0.40(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
| Refractive Index | 495 ° (C=0.7, CHCl3) |
| MDL | MFCD00065294 |
Antibiotic lichen acid - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S60 - This material and its container must be disposed of as hazardous waste. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| RTECS | HP5270000 |
| Toxicity | LD50 i.v. in mice: 25 mg/kg (Gottlieb, Shaw) |
Antibiotic lichen acid - Reference
| Reference Show more | 1. Ye Jia, Zhang Hao, Zhang Ning. Determination of Eusnic Acid Content in Lichens of Huangmei at Different Altitudes [J]. Hubei Agricultural Science 2014 53(06):1415-1417. |
Antibiotic lichen acid - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Background and overview | Lichen (l ichen) is composed of symbiotic bacteria (ascomycetes or spore bacteria) and symbiotic algae (cyanobacteria or green algae) after a long biological evolution, A type of biological organism with high genetic stability, also known as lichen-type fungi. Lichen is a kind of important organism in natural ecosystem, which widely exists in nature, including plateau, grassland, forest, arid desert, rock surface, even equator and polar regions. In taxonomy, lichens are treated as an independent phylum. There are currently 522 genera and more than 13500 species known. China is very rich in lichen resources, involving 232 genera and 1766 species, of which more than 300 kinds of lichens are unique to China. The secondary metabolites produced by lichen have strong biological activity. Lichens have been widely used in antibacterial treatment in folk for a long time. Because many secondary metabolites produced by lichens have strong antibacterial effects, after penicillin, lichens were officially used as screening antibiotics between 1940 and 1950. An important research object. In fact, a large number of modern studies have further confirmed the antibacterial effect of lichens. usnic acid is currently one of the most important and most widely distributed lichen acids, also known as lichen acid, mainly found in Usnea (Usnea), Alectoria (Usnea), Arborea (Ramalina), Arborea (Evernia), Ce traria (Ce traria), Litmus (Cladonia), Plum Among many species of the genera (Parmelia), Tea (Lecanora), and Red Star (Haematomma), the content of lichen in Usnea, Placeaceae and Litmus family generally accounts for 0.1 ~ 4% of the dry weight of lichen, and 8% in golden hair (Alectoria ochroleuca). Isnic acid is a powerful furan antibiotic with optical rotation. There are two forms () and (-) found in lichen. According to reports, in the 1960s, the former Soviet Union made usnic acid into various dosage forms, which are widely used to treat wounds, burns, chapped and other diseases. Because of its strong antibacterial, anti-radiation, anti-corrosion and other effects, usnic acid has been used in medicine, perfume, cosmetics and other industries, and as a pure substance added to toothpaste, mouthwash, deodorant, sunscreen and weight loss products. In recent years, the research on usnic acid has focused on antibacterial, antiviral, insecticidal, antitumor and anti-inflammatory. |
| traits | light yellow silk needle crystal. The solubility in 100mL of the following solvents is 0.01g of water, 0.02g of ethanol and 0.77g of acetone respectively. Its sodium salt is highly water-soluble and is easy to combine with amine compounds. specific rotation [α] D16: 509.4(c = 0.697, chloroform), UV λnm(ε):282 (22800),233(30200). |
| pharmacological action | 1. antibacterial effect: usnic acid can effectively inhibit the growth of gram-positive bacteria such as staphylococcus aureus, MRSA, acne bacillus and corynebacterium, and can inhibit the growth of bran batch of spores, directly kill the cells of staphylococcus aureus, and hinder the signal transduction pathway of Pseudomonas aeruginosa, it is suggested that Usnea grandacea extract and usnic acid can be used to treat acne, rosacea, seborrheic dermatitis and other related skin diseases. In addition, usnic acid has an elimination effect on sa drug-resistant plasmids, and its elimination rate is 52% for 24 hours, prolonging the action time to 48 hours, and the elimination rate can reach 14.6%, which may be used for clinical treatment of drug-resistant sa infection. 2. Antiviral effect: Studies have proved that usnic acid has the potential to inhibit the proliferation of mouse polyomavirus. It mainly inhibits the formation of messenger RNA, thereby indirectly inhibiting DNA replication. Eusnic acid in the body of Usnea longus has the activity of inhibiting Epstein-Barr virus (Epstein-barrvirus,EBV), of which (+) -usnic acid shows the highest inhibitory activity (ED501.0μg/mL), and (-)-usnic acid The inhibitory activity is weak (ED505.0 μg/mL). 3. Insecticidal effect:(+)-usnic acid has the activity of killing preflagellates of Leishmania dovish (kala-azar protozoa), and the in vitro active concentration of (+)-usnic acid is 25 μg/mL. The minimum effective concentration of S-(-) usnic acid in vitro is 0.4 mg/mL, and there is no significant difference in the effect of 0.4 mg/mL and above between usnic acid and metronidazole with the same concentration. Within 5- 30 μg/mL, usnic acid has an inhibitory effect on the growth of trypanosoma larvae. usnic acid can also significantly reduce the amount of trypanosoma in the blood. Using 40 or 80 μg/mL usnic acid to infect macrophages can lead to the disintegration of trypanosoma mitochondria and Golgi apparatus, and the cytoplasm becomes vacuolated, but it has no effect on host cells. 4. anti-tumor effect: usnic acid has anti-wild-type P 53 breast cancer cell line MCF7, non-functional P53 breast cancer cell line MDA-MB-231, lung cancer cell line H1299 and various cancer cell lines L1210, 3LL, DU145, MCF7, K-562 and U251 activity, but it does not cause damage to DNA of normal cells, so it is expected to be developed into a new generation of anti-cancer drugs. To study the inhibitory effect of usnic acid extracted from fungal Usnea on the proliferation of prostate cancer PC-3M cells cultured in vitro, the results of cell growth inhibition experiments show that its maximum inhibition rate can reach more than 80%, and the biological effect is dose-dependent Inhibition relationship, indicating that usnic acid has inhibitory effect on cultured PC-3M cells in vitro, slows down the proliferation of tumor cells, and has obvious anti-tumor effect. However, usnic acid had no inhibitory effect on 12(S)-LOX cultured in vitro from human platelets. The water solubility of usnic acid was poor. The effects of 10% HP -β- CD as solubilizer on three human malignant cell lines were investigated at pH7.4. The results showed that the solubility of usnic acid in 10% HP -β- CD increased 70 times, and the EC50 for T-47D, Panc-1 and PC-3 cells were 2.9 μg/mL, 4.3 μg/mL and 8.2 μg/mL respectively. 5. Anti-inflammatory activity: The anti-inflammatory activity of usnic acid was studied by using rat foot swelling experiment (acute inflammation) and rat cotton ball granuloma experiment (chronic inflammation), and ibuprofen was used as a positive control drug. The results showed that for acute inflammation, ibuprofen had better anti-inflammatory effect than usnic acid at the same dose (100 mg/kg orally) as ibuprofen; for chronic inflammation, the anti-inflammatory effect of the two is equivalent, compared with the control group, there is a significant difference. It is speculated that the anti-inflammatory mechanism of pine acid is related to the inhibition of prostaglandin synthesis. 6. other activities: to study the effect of sodium usenate on skin wound healing. the overall experiment showed that sodium usenate had accelerated repair effect on experimental large skin injury, but had no promotion effect on L929 fibroblast proliferation at 0.5~8 μg/mL. In addition, the effect of sodium usenate on fibroblasts and its mechanism of promoting wound healing were also investigated. The results showed that sodium usenate can promote the secretion of TGF-1 and EGF by fibroblasts, and increase with the increase of drug concentration, produce chemotaxis on repair cells and inflammatory cells, promote the migration of repair cells and the deposition of extracellular matrix, and promote wound healing. In addition, experimental studies show that usnic acid has a better gastric protective effect on indomethacin-induced gastric ulcer model in rats. Compared with the model group, it can significantly increase the levels of SOD, GSH and GPx, reduce LPO level, increase cNOS and decrease iNOS in rats. In terms of radiation resistance, the absorption of secondary metabolites of lichen in UV region was studied. The results showed that usnic acid mainly absorbs in UV-B region and is relatively stable to light. Moreover, the photolysis products of usnic acid still have absorption effect on UV, suggesting that usnic acid is a very potential natural opacifier, which can be used in cosmetics such as sunscreen oil. |
| toxicity study | currently, the human toxicity experimental data of usnic acid are still lacking. Eusnic acid mainly causes hepatotoxicity. To observe the effects of usnic acid on isolated liver parenchymal cells and liver mitochondria in rats, it was shown that high dose of usnic acid can cause the destruction of membrane structure integrity, mitochondrial respiratory function and oxidative phosphorylation, and CCl4 has a synergistic effect. Studies have confirmed that usnic acid contained in the weight-loss drug Li pokinetix has obvious hepatotoxin effect, which can trigger oxidative stress and destroy the normal metabolism of cells. Addition to the product as a dietary supplement can easily cause hepatotoxicity and acute liver failure, which should be paid attention. |
| preparation process | 1. alkaline water extraction 50g of comminuted Usnea raw material is weighed, and single factor experiments are carried out in the following table. the ratio of solid to liquid is 1: 10 and 1: 8,90 ℃ hot water bath extraction is carried out twice for 2 hours each time, the filtrate is combined with acidification, and the content of usnic acid is determined by usnic acid product. the results are shown in the figure: with the increase of NaOH concentration, the yield of usnic acid product increases. when NaOH reaches 1.0%, the yield is the largest, which is 7.2%. The content of usnic acid also increases with the increase of NaOH concentration. when the concentration of NaOH is 1.5%, the content is the highest, which is 27.8. at the same time, its conversion rate [(I .e. product yield × usnic acid content)/the quality of usnic acid in the material] is also the highest, for 72.9%, 1.5% NaOH should be selected as extraction solvent when alkaline water is used for extraction. 2. alkali alcohol extraction 50g of comminuted ussnea raw material is weighed, the ratio of solid to liquid is 1: 10 and 1: 8, hot water bath extraction at 90 ℃ is carried out twice for 2h each time, the filtrate is combined with acidification, and the content of ussic acid is determined by ussic acid product. the results are shown in the figure: according to the same ethanol concentration (75%), the effect of different concentrations of Na2CO3 on the extraction of usnic acid can be seen. With the increase of Na2CO3 concentration, the yield of usnic acid product increases. The highest content of usnic acid in the product is treated with No.1, and the content has a downward trend with the increase of Na2CO3. The higher conversion rates are No. 4 and No. 3, 86.2% and 82.9% respectively. Considering comprehensively, treatment No. 3, I .e. 75% ethanol + 4% Na2CO3, should be selected. |
| pharmacokinetics | in 1992, Indian scholars studied the metabolic process of usnic acid in rabbits, using doses of 5 and 20 mg/kg body weight respectively through intravenous and oral administration, and using high performance liquid chromatography to determine the content of usnic acid in animal plasma samples at different time points. The experimental results showed that after intravenous administration, the biological half-life of usnic acid was 10.7±4.6 h, the average distribution volume of the central chamber was 43.9±21.3ml/kg, and the systematic clearance rate was 12.2±3.0ml /(h · kg). The above pharmacokinetic data were analyzed by three-compartment model and single-compartment model respectively, and the results were basically the same. The results of the two doses (5 and 20 mg/kg) were also similar. Data analysis of oral route using single-compartment model showed that the peak concentration of usnic acid in plasma appeared at 12.2±3.8 h, and the average oral bioavailability was 77.8%. So far, there is no detailed study on the distribution characteristics of usnic acid in animals. |
| use | usnic acid is a broad-spectrum antibiotic, which has a strong inhibitory effect on most gram-positive bacteria. the concentration of 50 μg/mL can completely inhibit the growth of bacteria and is used as a high-efficiency preservative in cosmetics. It has a selective inhibitory effect on the main bacterial streptococcus that causes oral diseases and dental caries. Eusnic acid is effective for a variety of skin diseases such as burns, infections, and psoriasis. 1. Clinical application: daily oral administration of 0.1-1.0g of sodium asperate can improve certain symptoms of human tuberculosis and intestinal tuberculosis, such as cough, loss of appetite, fever or intestinal tuberculosis diarrhea, and even make the microscopic examination of tuberculosis turn negative. It can also be used for purulent trauma, burns and skin infections. 2. Application in environmental monitoring: Paraquat (an extremely toxic herbicide) can transfer electrons to O2 from different transportation systems to produce superoxide free radicals. Two kinds of lichens were treated with paraquat, the small wrinkled plum coat and the smooth plum coat, and then the content of usnic acid in the two kinds of lichens was measured by HPLC. Results The content of usnic acid in smooth plum clothing increased by 36.3%, and that in small wrinkled plum clothing increased by 13.7%. They believe that the effect of usnic acid depends on different lichen species. This study provides a direction for the application of usnic acid in pharmaceutical, cosmetic and environmental biological monitoring. 3. Application in other aspects: In recent years, it has been found that usnic acid has the effect of analgesic and antipyretic agent, and its efficacy can be compared with aminopyrine (antipyretic analgesic), butazine (anti-inflammatory analgesic) and hydrocortisone semi-succinyl ester. At the same time, it has been found to have similar effects to antiviral drugs, anti-protozoa drugs, anti-proliferative active drugs and anti-inflammatory drugs. Intravenous injection of 10mg/kg sodium usenate can rapidly and significantly enhance the breathing of anesthetized cats, increase ventilation for a long time, increase oxygen consumption, and increase body temperature. These all indicate that its metabolism is enhanced, has a similar effect to dinitrophenol, and its toxicity is greater than dinitrophenol. Because of its antibacterial effect, usnic acid can be used as a preservative. |
| adverse reactions | the more significant side effects of usnic acid are mainly allergic reactions caused by contact dermatitis. In early studies, it was found that the people with allergic reactions were mainly factory workers, lichen pickers or horticulturists who were exposed to forest wood, lichen plants, etc.; in recent studies, it was found that the use or contact with lichen extract deodorant, lichen acid mixture, and d-usnic acid 4 patients with allergic dermatitis were subjected to a patch test, and the results showed that all 4 patients were positive, it is suggested that perfumes, cosmetics, deodorants, preservatives, etc. containing usnic acid and other lichen plant extracts may cause contact dermatitis, but usnic acid does not cause photosensitization. |
| main reference materials | [1] "daily chemical raw materials manual" compilation group. Handbook of daily chemical raw materials. Beijing: China Light Industry Press. [2] Zhao Ying et al. Research progress of usnic acid. Chinese patent medicine. 2010,32(2): 270-273. [3] Wei Linlin et al. Research progress on anti-pathogenic biological activity and drug action of usnic acid. Chinese Journal of Pathogenic Biology. 2009 ,4 (5):387-390. [4] Qian Hua et al. Study on extraction technology of usnic acid. Wild plant resources in China. 2012.31(1):26-29. [5] Wang Li et al. research progress of usnic acid. biotechnology communication. 2005,16(4):472-473. [6] Wang Li et al. research progress of usnic acid. Journal of Xinjiang University. 2004,21:104-106. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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