Name | WEDELOLACTONE |
Synonyms | WEDELOLACTONE Wedelolactone IKK Inhibitor II, Wedelolactone 5,11,12-Trihydroxy-7-MethoxycouMestan 7-methoxy-5,11,12-trihydroxycoumestan 1,8,9-trihydroxy-3-Methoxy-6H-benzofuro[3,2-c]chroMen-6-one 1,8,9-trihydroxy-3-methoxy-6H-[1]benzofuro[3,2-c]chromen-6-one 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one 6H-Benzofuro(3,2-C)(1)benzopyran-6-one, 1,8,9-trihydroxy-3-methoxy- |
CAS | 524-12-9 |
EINECS | 200-158-5 |
InChI | InChI=1/C16H10O7/c1-21-6-2-10(19)14-12(3-6)23-16(20)13-7-4-8(17)9(18)5-11(7)22-15(13)14/h2-5,17-19H,1H3 |
InChIKey | XQDCKJKKMFWXGB-UHFFFAOYSA-N |
Molecular Formula | C16H10O7 |
Molar Mass | 314.25 |
Density | 1.655±0.06 g/cm3(Predicted) |
Melting Point | 327~330℃ |
Boling Point | 498.4±45.0 °C(Predicted) |
Flash Point | 255.2°C |
Solubility | Soluble in methanol, DMSO and other solvents, insoluble in petroleum ether, dichloromethane, chloroform. |
Vapor Presure | 1.48E-10mmHg at 25°C |
Appearance | White crystal |
Color | brown-beige |
pKa | 6.90±0.20(Predicted) |
Storage Condition | 2-8°C |
Refractive Index | 1.758 |
MDL | MFCD07778564 |
Physical and Chemical Properties | Soluble in methanol, DMSO and other solvents, insoluble in petroleum ether, dichloromethane, chloroform. From the aerial part of the Compositae plant Eclipta Eclipta prostrasta L. |
Hazard Symbols | Xn - Harmful |
Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact |
Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
WGK Germany | 3 |
HS Code | 29322090 |
Reference Show more | 1. Li Bing, Feng Suxiang, Feng Zhiyi, Zhang Hao-jie, Sun Ying-na, Wang Pei-Yang, Shu Sheng-nan. Quality Evaluation of eclipta prostrata from different habitats based on HPLC-Q-HR/MS technology and multi-component content identification [J]. Shi Zhen, National Medicine, 2020,31(06):1329-1333. 2. Zhao, Yun, et al.. "Experimental gerontology 62 (2015): 37-44.https:// doi.org/10.1016/j. Exger.12/017, 2014 3. [IF = 4.411] Li Jia et al."Systematic Profiling of the Multicomponents and Authentication of Erzhi Pill by UHPLC/Q-Orbitrap-MS Oriented Rapid Polarity-Switching Data-Dependent Acquisition and Selective Monitoring of the Chemical Markers Deduced from Fingerprint Analys 4. [IF=4.032] Yun Zhao et al."Effect of Eclipta prostrata on lipid metabolism in hyperlipidemic animals."Exp Gerontol. 2015 Feb;62:37 |
overview | wedelolactone,WEL) is a small molecule active substance (molecular formula C16H10O7) of sweet bean grass ether isolated from Herba Ecliptae of Chinese herbal medicine. As an indicator ingredient, it has formulated the quality standard of Chinese herbal medicine, which is included in the 2010 edition of Chinese Pharmacopoeia. Wedelia plants are commonly used in Asia and South America to treat septic shock, liver diseases, viral infections and snake bites. Wedelia lactone may be one of the main compounds that exert hepatoprotective activity in Wedelia and upland. In recent years, many pharmacological studies have shown that WEL, as an inhibitor of Na -K-ATPase and isomerase type II, plays a role in protecting liver, anti-postmenstrual osteoporosis, immunosuppression, and anti-cancer. However, its pharmacokinetic studies have not been reported. |
basic information | physical properties: colorless flakes (methanol), index number: 2-W0002 chemical classification: coumarin Coumarin |
pharmacokinetics | plasma protein binding [1]: drug plasma protein binding rate (Binding Rate of Plasma protein,BRPP) is one of the important parameters of pharmacokinetics, which directly affects the intensity and half-life of drugs and has important guiding significance for clinical application of drugs. The experiment of WEL and rat plasma protein binding rate showed that the protein binding rate of WEL at three concentrations did not show concentration-dependent relationship, and when dialysis equilibrium was reached, the average binding rate of WEL and plasma protein was greater than 80%, belonging to high protein binding rate drugs. It is speculated that this component mainly exists in the plasma as a binding type with a longer half-life. Since free drugs are easy to achieve complete transport and exert their efficacy, it is recommended to use other drugs in clinical combination and carry out in vitro drug competition and combination experiments. Hepatocyte function [3]: Ischemia-reperfusion injury is one of the major complications such as partial hepatectomy, liver transplantation, trauma, and shock. To explore the mechanism of liver ischemia-reperfusion injury, and to find methods or drugs to protect ischemic liver cells and enhance the body's tolerance. Studies have found that weelolide can inhibit the production of Raw264.7 cell IL-6 and TNF-α inflammatory cytokines caused by LPS, and can inhibit liver fibrosis, showing a better liver protection effect. Lipopolysaccharide [4]: Lipopolysaccharide (lipopolysaccharide,LPS) is the main pathogenic factor leading to sepsis of gram-negative bacteria. Among them, LPS-induced activation of nuclear factor-κB (NF-κB) plays an important role in the occurrence and development of many critical diseases caused by sepsis. NF-κB, as a multidirectional and pleiotropic nuclear transcription regulator, plays an important role in the expression of inflammatory mediators such as IL-6, TNF-α, NO and PGE2. Wedelolide can inhibit the expression of NF-κB p65 protein in RAW264.7 cells induced by LPS, and inhibit the massive translocation of NF-κB into the nucleus, thus reducing the massive release of terminal inflammatory mediators. In a word, the anti-inflammatory mechanism of weelolide is related to inhibiting NF-κB activation induced by LPS, thus reducing the production of inflammatory cytokines IL-6 and TNF-α. |
plant source | 1. alba(L.)Hassk, Eclipta of Asteraceae (Compositae), aboveground part (yield: 0.02%); Snakehead intestinal Eclipta prostrata (L.)L. whole grass; Wedelia Wedelia calendulacea Less. Leaves; 2. Hypericaceae (Hypericaceae) Hypericum erectum Thunb. Whole grass (yield: 0.006%). |
activity and code | 1.A5B: anti-liver toxicity. It has inhibitory effect on rat hepatocyte poisoning caused by CCl4,GalN and toxicanin. At 31 μg/mL, the inhibitory rate on toxicanin is 98% and ED50 is 8 μg/mL, which is better than silymarin and can obviously stimulate hepatocyte regeneration. 2.E5: is a selective inhibitor of 5-lipoxygenase, and its IC50 is 2.5 μM. 3.V3D: anti-snake venom effect. Neutralizes the venom of South American rattlesnakes and is used as an antidote to snake bites. 4.B2B: hemostatic effect. ED50 is 0.3 mg/kg. At a dose of 0.5 mg/kg, the bleeding time was shortened by 3.9 minutes. |
patent status | 1. process patent: Wagner H,et al. DE 3525363 (1987,4pp); 2. pharmaceutical patent: Hokuriku Pharm Co Ltd. JP 60120879(1985,4pp). |
references | [1] Fang Yue, Huang Xuejuan, You Xinyi, Yin Zhiyong, Zhang Chaofeng, Zhang Mian. Determination of Plasma Protein Binding Rate of Wedelolide Rats [J]. Pharmacy and Clinical Research, 2015,03:246-248. [2] edited by Chen Huifang. Dictionary of Plant Active Ingredients, Volume 2. Beijing: China Medical Science and Technology Press. 2001. Page 1121-1122. [3] Chen Jie, Li Ruiming, Xu Jing, Guan Biqiong, Luo Ziling. Effects of Wedelia Lactone on COX-2, NO and TNF-α in RAW264.7 Cells Induced by Lipopolysaccharide [A]. Guangdong Pharmaceutical Association. Proceedings of Guangdong Pharmacist Week Conference 2013 [C]. Guangdong Pharmaceutical Association:,2013:6. [4] Xu Jing, Chen Jie, Sun Pingping, Yuan Fang. Study on Anti-hepatic Ischemia Reperfusion Injury of Rats with Wedelia Lactone [J]. Shi Zhen Guo Yi Guo Yao, 2014,09:2058-2059. |
use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: anti-liver toxicity, anti-liver toxicity, hemostatic effect. |