Puerarin
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Puerarin
structure -
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CAS No:
3681-99-0
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Formula:
C21H20O9
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Chemical Name:
Puerarin
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Synonyms:
DAIDZEIN-8-C-GLUCOSIDE;8-GLUCOSYLDAIDZEIN;7-HYDROXY-3-[4-HYDROXYPHENYL]-1-BENZOPYRAN-4-ONE 8-[BETA-D-GLUCOPYRANOSIDE;PSYCHOSINE;PUERARIAROOT.P.E;PUERARIN EXTRACT;4H-1-Benzopyran-4-one,8-β-D-glucopyranosyl-;7-hydroxy-3-(4-hydroxyphenyl)-
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Categories:
Active Pharmaceutical Ingredients > Circulatory System Drugs
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CAS No:
Description
White powder
Puerarin, also known as pueraria flavonoids, is a kind of flavonoid glycoside extracted from the roots of Pueraria alba or Pueraria thomsonii and is also one of the main effective ingredients of Pueraria lobata. That Pueraria lobate was used to treat diseases has already been recorded in China’s ancient medical books such as Shen Nong’s Materia Medica, Treatise on Miscellaneous Diseases and Medical Dictionary.Kanzu root is widely distributed in our country and of rich resources. It has been reported that puerarin could be extracted from Pueraria lobata (Wild.) Ohwi, Radix Pueraria thomsonii, Pueraria omeiensiswanget Tang, Pueraria edulis Pamp and Pueraria phaseoloides, but the content of puerarin differs.Pueraria has a great value for nutrition and medicine and was considered the south ginseng of China. Puerarin has been widespread concerned over our country for its use of food and medicine in recent years.
In 1959, Japanese chemist Shibata Shoji first studied the chemical production of pueraria root, indicating that isoflavones are the main active ingredients of pueraria root, including puerarin, daidzin and daidzein . Then in 2003, David Lee first total synthesized analogical puerarin . And it was in 1974 that puerarin was first extracted by Fang Qicheng and other chemists in China . Due to its strong activity of anti-cardiovascular and anti-cerebrovascular ischemia and hypoxia, expanding the coronary artery and cerebrovascular, reducing myocardial oxygen consumption, and improving myocardial systolic and microcirculation function, puerarin was approved for clinical use by the Ministry of Health in 1993.In recent years, researchers have synthesized a series of puerarin derivatives, and active research showed that the part of the puerarin derivatives has a good biological activity and bioavailability. In a new dosage form research, researchers have developed several types of dosage forms such as quickrelease solid dispersions, solid from microemulsion preparation, etc., which greatly increase the solubility of puerarin, thus improving bioavailability. In recent years,the research on crystal drug has opened up new ways for the application of puerarin.
ChEBI: A hydroxyisoflavone that is isoflavone substituted by hydroxy groups at positions 7 and 4' and a beta-D-glucopyranosyl residue at position 8 via a C-glycosidic linkage.
Characteristics
303nm(MeOH)(lit.)
157
Appearance: White to light-yellow crystalline powder. Solubility: Soluble in methanol, freely soluble in ethanol, slightly soluble in water, insoluble in chloroform and ether. Melting point: 187–189°C.
0.38610
White to Off-white Powder
1.614±0.06 g/cm3(Predicted)
187-189°C
688.0±55.0 °C(Predicted)
281.5ºC
1.719
Soluble in DMSO or DMF. Slightly soluble in water or ethanol
2-8°C
6.46±0.20(Predicted)
2-8°C
Puerarin Use and Manufacturing
Add 10 mg of To achieve a solution of isoflavone 6 (53 mg, 67 lmol) in anhydrous CH2Cl2 (0.14 mL), a solution of BBr3 (81.6 mg, 0.33 mmol) in anhydrous CH2Cl2 (0.31 mL) was added dropwise at 78 C for 30 min under an Ar atmosphere. The cold bath was removed, and the mixture was stirred for 10 min. Methanol (3 mL) was added to the reaction mixture dropwise at 0 C within 5 min. The solvent was evaporated under reduced pressure to yield a brown syrup (70 mg), which was subjected to silica gel column chromatography (20:1, dichloromethane methanol) to obtain a colorless solid 7 (26.5 mg, 95.0percent). m.p.183'185 C. 1H-NMR (400 MHz, DMSO-d6):d 8.34 (s, 1H; H-2), 7.92 (d, J ¼ 8.8 Hz, 1H; H-5), 7.39 (d, J ¼ 8.6 Hz, 2H;H-20, H-60), 7.00 (d, J ¼ 8.8 Hz, 1H; H-6), 6.80 (d, J ¼ 8.6 Hz, 2H; H-3?, H-50), 4.80 (d, J ¼ 9.8 Hz, 1H; H-100), 4.04 (dd, J ¼ 9.8 Hz, 8.6 Hz; H-200), 3.71(d, J ¼ 10.9 Hz, 1H; H-400), 3.43 (dd, J ¼ 11.6, 5.4 Hz, 1H; H-6'a), 3.30'3.18(m, 3H; H-3, H-5, H-6'b). 13C-NMR (150 MHz, CD3OD): d 178.3 (C-4), 163.0 (C-7), 158.7 (C-40), 154.4, 131.3 (C-20, C-60), 128.1, 125.6, 124.2, 118.5, 116.2 (C-30, C-50), 113.2 (C-8), 82.8 (C-500), 80.0 (C-300), 75.7 (C-100), 73.0 (C-200), 71.7 (C-400), 62.8 (C-600). HRESI-MS (m/z): calcd for C21H19O9 [M - H]th 415.1035, found 415.1027.Fu
Puerarin is a natural isoflavone isolated from plants of the genus Pueraria used in traditional Chinese herbal medicine. It is biotransformed by intestinal bacteria to give the phytoestrogens daidzein and equol , resulting in antithrombotic, antiallergic, and other salutary effects. When given intraperitoneally, puerarin evokes diverse responses by modulating serotonin receptors. This compound also suppresses lipopolysaccharide-mediated activation of NF-κB in RAW 264.6 macrophages when given at 20-40 μM.
beta-adrenergic blocker
Puerarin is a naturally occuring isoflavonoid derived from Chinese medical herb kudzu root and has been used for the treatment of various cardiovascular diseases. Recent sutdies have shown the potenti al of puerarin treatment as a novel approach to lowering the risk of or improving function in ischemia-reperfusion brain injury-related disorders.
Drug Function and Efficacy
Unspecified
Registered Holders
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Shaanxi Likang Pharmaceutical Co., Ltd.
Active
China
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Reyoung Pharmaceutical Co., Ltd.
Active
China
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Guanghan Lusong Pharmaceutical Co., Ltd.
Active
China
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