33570-04-6
(-)-bilobalide from ginkgo leaves
CAS: 33570-04-6
Molecular Formula: C15H18O8
33570-04-6 - Names and Identifiers
| Name | (-)-bilobalide from ginkgo leaves |
| Synonyms | BILOBALID Bilobalide BILOBALIDE (-)-BILOBALIDE Bilobalide 33570-04-6 (-)-bilobalide from ginkgo leaves 5,3'-DIHYDROXY-3,6,7,4'-TETRAMETHOXYFLAVONE |
| CAS | 33570-04-6 |
| EINECS | 608-892-9 |
| InChI | InChI=1/C15H18O8/c1-12(2,3)14(20)4-6-13(5-7(16)21-6)10(19)23-11-15(13,14)8(17)9(18)22-11/h6,8,11,17,20H,4-5H2,1-3H3/t6-,8?,11+,13-,14+,15?/m0/s1 |
33570-04-6 - Physico-chemical Properties
| Molecular Formula | C15H18O8 |
| Molar Mass | 326.3 |
| Density | 1.56±0.1 g/cm3(Predicted) |
| Melting Point | >300° |
| Boling Point | 651.7±55.0 °C(Predicted) |
| Specific Rotation(α) | 57820 -64.3° (c = 2 in acetone) |
| Flash Point | 247.5°C |
| Solubility | DMSO : ≥ 100 mg/mL (306.47 mM) |
| Vapor Presure | 9.57E-20mmHg at 25°C |
| Appearance | Colorless crystal (water) |
| Color | White to Off-White |
| Merck | 14,1220 |
| pKa | 11.74±0.40(Predicted) |
| Storage Condition | −20°C |
| Stability | Hygroscopic |
| Refractive Index | 1.605 |
| MDL | MFCD00132880 |
| Physical and Chemical Properties | Dried leaves from the Ginkgo family Ginkgo biloba Ginkgo bilba L. |
33570-04-6 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| RTECS | LV1665000 |
| FLUKA BRAND F CODES | 10 |
| HS Code | 29322090 |
33570-04-6 - Reference
| Reference Show more | 1. Li Zehong, Feng Ru, Yuan Hong-hui, Cheng Hua, Cheng Shui-yuan. Extraction process of terpene lactones from Ginkgo biloba tablets [J]. Northern horticulture, 2017, 36 (23):176-180. 2. Feng, such as Li Zehong, Yuan Honghui, etc. Effects of different stress treatments on terpene lactones content in ginkgo biloba leaves [J]. Journal of Wuhan Polytechnic University 2017 036(001):34-38 53. 3. Jiang Meifang, Gaoqi, Wang Dandan. Determination of integrated dissolution of terpene lactones and flavone glycosides in ginkgo biloba ketone ester tablets [J]. Chinese patent medicine, 2020,42(10):2716-2719. 4. Qiao, Hongzhi, et al. "Fabrication and in vitro/in vivo evaluation of atomus andrographolde nanosuspens stabilized by alpha-tocopheryl polyethlycol 1000 sucinate/sodium lauryl sulfate." International journal of nanomedic12 (2017): 1033.ht< br>5. [IF = 6.4] Hongzhi Qiao et al."Fabrication and in vitro/in vivo evaluation of amorphous andrographolide nanosuspensions stabilized by d-α-tocopheryl polyethylene glycol 1000 succinate/sodium lauryl sulfate."Int J Nanomed. 2017; 12: 1033-1046 6. [IF=3.935] Xingliang Niu et al."Hydrogen/deuterium exchange a unique and effective method for MS fragmentation behavior elucidation of ginkgolides and its application to systematic research in Ginkgo biloba."J Pharmaceut Biomed. 2017 Feb;134:181 7. [IF=6.558] Qingqing Song et al."Binary code, a flexible tool for diagnostic metabolite sequencing of medicinal plants."Anal Chim Acta. 2019 Dec;1088:89 8. [IF=5.645] Ying Guo et al."Spatial prediction and delineation of Ginkgo biloba production areas under current and future climatic conditions."Ind Crop Prod. 2021 Aug;166:113444 9. [IF=3.935] Yongyi Li et al."Integrated molecular networking strategy enhance the accuracy and visualization of components identification: A case study of Ginkgo biloba leaf extract."J Pharmaceut Biomed. 2022 Feb;209:114523 |
33570-04-6 - Reference Information
| Plant source: | Ginkgo biloba |
| overview | bilobalide is one of the main functional components of ginkgo biloba leaves, and also includes ginkgolide and ginkgolide a, B and c. Bilobalide is a neuropsychiatric drug, currently mainly used to treat neuropathy, encephalopathy and myelopathy, anti-aging. However, the solubility of flavonoids and colloidal substances in bilobalide and ginkgo biloba extract is very small. They are usually mixed into one body and are sticky and paste-like. Separation and purification are very difficult., In recent years, the separation of bilobalide in China is mostly based on Ginkgo biloba extract, using high performance liquid chromatography column small batch preparation, coordination chromatography separation and purification, or using macroporous adsorption resin for separation. Bilobalide is an important component in Ginkgo biloba extract. Bilobalide can reduce blood pressure, slow down heart rate and increase coronary flow in animals. Bilobalide also has a protective effect on myocardial ischemia-reperfusion injury. At the same time, it can antagonize abnormal platelet aggregation and thrombosis caused by platelet activating factor, thus reducing plasma viscosity and whole blood viscosity, and its protective effect on nerves. picture: ginkgo biloba |
| pharmacological action | bilobalide is the only sesquiterpene substance extracted from ginkgo biloba. bilobalide has good curative effect on cardiovascular and cerebrovascular diseases such as angina pectoris, myocardial infarction, coronary heart disease, hypertension and arrhythmia. Effect on lowering blood pressure and slowing down heart rate: bilobalide has the effect of lowering blood pressure. Its antihypertensive effect is to increase the activity of superoxide dismutase (SOD) in serum, reduce the concentration of malondialdehyde (MDA) in serum, relax blood vessels, reduce diastolic blood pressure and slow down heart rate; and inhibit myocardial cell contraction and reduce cardiac contraction. Secondly, systolic blood pressure can reflect the ejection capacity of the heart to a certain extent. A comparison of dimethyl sulfoxide and bilobalide shows that both can reduce systolic blood pressure, but bilobalide is more significant in reducing systolic blood pressure. It shows that bilobalide relaxes peripheral arterioles, reduces peripheral resistance, and decreases diastolic pressure. The relaxation effect of Ginkgo biloba extract and bilobalide on arterial rings in rats decreased with the increase of age. protection of myocardial ischemia-reperfusion injury: bilobalide has obvious protective effect on myocardial cells, and bilobalide has concentration-dependent protective effect on myocardial cells and endothelial cells, of which 5 ng/m L-1 bilobalide significantly reduces the mortality of myocardial cells and endothelial cells. effects on cardiac hemodynamics and coronary flow: bilobalide can change cardiac hemodynamics, such as hemodynamic changes in rats after intravenous injection of ginkgo biloba extract into normal anesthetized rats, as well as antagonizing cardiovascular function changes caused by PAF, so as to inhibit myocardial strength, slow down heart rate, reduce myocardial oxygen consumption, relax blood vessels and visceral smooth muscle, increase coronary flow and lower blood pressure. effects on platelets: ginkgo biloba extract can antagonize platelet activating factor, inhibit platelet aggregation and thrombosis, improve hemorheology, expand cerebral blood vessels, increase cerebral blood flow, resist free radicals, inhibit glutamine toxicity, improve energy metabolism disorder and acidosis caused by cerebral ischemia and hypoxia, reduce ischemic cerebral edema, reduce blood lipid and resist atherosclerosis. In the treatment of ischemic cerebrovascular disease, Ginkgo biloba preparation improves cerebral blood supply, protects brain cells, promotes the recovery of nerve function and improves clinical symptoms. Protective effect on the nervous system: bilobalide has a protective effect on the damage of the central nervous system. Bilobalide can shorten the learning reaction time, prolong the memory time and reduce the number of errors in model mice. It can increase SOD activity and reduce MDA content in brain tissue of mice, and reduce cholinesterase activity and NO content. |
| references | [1] pan Jian, Gao Xianglan, yang yi, et al. separation and purification of bilobalide from ginkgo biloba extract [J]. Chinese herbal medicine, 2009(s1):135-137. [2] Tang yuanpeng, Zeng Jing, huang Qiren. Study on pharmacological effects of bilobalide [J]. Journal of Gannan Medical College, 2015(1):153-155. [3] Xu Jing, Sun Changkai, Wang Dongmei, et al. Protective effect of bilobalide on nerve damage caused by glutamic acid excitotoxicity [J]. Chinese herbal medicine, 2009, 40(10):1593-1597. [4] Huang Huan, Cao Mingcheng, Zhu Zhengyi, et al. protective effect of bilobalide on vascular dementia mice [J]. Anhui medicine, 2013, 17(3):383-386. |
| Biological activity | Bilobalide is a biologically active terpene lactone found in Ginkgo biloba. |
| use | used for content determination/identification/pharmacological experiments, etc. Pharmacological effects: Bilobalide is a drug for the nervous system and psychosis. It has a strange effect on the silly phenomenon due to old age. It is also used to treat neuropathy, encephalopathy and myelopathy. Symptoms include: paresthesia, flaccid or paralytic dementia, abnormal nerve reflexes, muscle atrophy, muscle cramps, tremor, superficial or deep sensitivity disorders, headache and limb pain, language disorders, vision and hearing disorders, dark halos, nerve disorders and lack of concentration, memory loss and loss of orientation, etc. |
Last Update：2024-04-09 21:11:58
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Tel: 0714-3999186
Email: 2853786052@qq.com
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